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Chemical diversity and biological activities of marine-derived sulphur containing alkaloids: A comprehensive update
⁎Corresponding author at: School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi Provance of China 712046. zhangnatprod@163.com (Dongdong Zhang)
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Received: ,
Accepted: ,
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Peer review under responsibility of King Saud University.
Abstract
Objectives
The ocean is a huge ecosystem with diverse marine life. Scientists have found a large number of natural products with unique structural features and excellent biological activity from these organisms. Marine-derived sulphur-containing alkaloids are a significant family of natural products with diverse structures and bioactivities. In this paper, the chemical and biological diversity of 972 sulfur-containing alkaloids derived from marine organisms reported from 1982 to 2022 were reviewed, and the structure–activity relationship was briefly analyzed, in order to provide reference for the discovery, synthesis, biological activity research and drug development of such compounds.
Key findings
A total of 972 marine-derived sulphur-containing alkaloids have been collected. Among them, 80.36% of sulphur-containing alkaloids are from marine sponges, fungi, tunicates and bacteria. Moreover, cytotoxicity is their most significant property, About 1/3 sulphur-containing organisms are reported to be cytotoxic. Aming them, discorhabdins, curacins, tanjungides, leptosins, and latrunculins exhibit better cytotoxicity. In addition, the structure–activity relationships of the cytotoxicity of these compounds have been summarized for further investigation.
Summary
In this paper, the chemical and bioactivity diversity of marine-derived sulphur-containing alkaloids were reviewed, which are a significant family of natural products with diverse structures and bioactivities. 972 sulphur-containing alkaloids were obtained from marine algae, sponges, cnidarians, tunicates, echinoderms, molluscs, bryozoans, dinoflagellates, cyanobacteria, bacteria and fungi, which possessed a wide spectrum of pharmacology including cytotoxicity, antibacterial, antifungal, antimitotic, antiviral, and other activities.
Keywords
Sulphur-containing alkaloids
Marine organisms
Chemical diversity
Bioactivity diversity
Cytotoxicity
1 Introduction
Natural medicines found from terrestrial plant and animal resources have been widely used in the clinical treatment of various diseases. However, with continuous exploitation, it has become increasingly difficult to develop drugs from terrestrial resources. Therefore, researchers have started to work on finding new sources of drugs from the ocean. (Lu et al., 2021).
The oceans are extremely rich in biological resources, including large numbers of fish, shrimps, crabs and many lower species such as molluscs, corals and seaweeds. Together, these organisms maintain the balance and stability of the marine ecosystem. (Seipp et al., 2021). It is worth noting that the marine environment has extreme living conditions such as high pressure, high salinity, hypoxia and low light. As a result, marine organisms often produce unique and active secondary metabolites, giving them an edge in the competition for limited resources. (Shang et al., 2018).
Pharmacological studies have shown that marine natural products (MNPs) have great potential in the treatment of various diseases. These results have stimulated research and development of marine organisms. After decades of in-depth studies, a large number of active ingredients have been found. (Lu et al., 2021). To date, 11 marine-derived drugs have successfully reached the market. For example, cytarabine (Cytosar-U®), ET-743 (Yondelis®), eribulin mesylate (Halaven®) and the antibody-drug conjugates (ADCs) brentuximab (Adcetris®) and polatumumab (Polivy®) have been used to treat cancer. Lovaza®, Vascepa® and Epanova® are used to treat hypertriglyceridemia. (Liang et al., 2019). In addition, 23 compounds are in various stages of clinical development. For example, the combination therapy of prambulin and docetaxel is currently in phase III clinical trials for the treatment of non-small cell lung cancer and the prevention of chemotherapy-induced neutropenia. lurbinectedin is in phase II/III clinical trials for the treatment of BRCA1/2-mutated breast cancer and small cell lung cancer. In addition, tetrodotoxin (Tectin), an alkaloid derived from the tetrodotoxin liver, is in phase III clinical trials for the treatment of severe pain. (Jiménez, 2018).
Among the many MNPs, sulphur-containing alkaloids are important natural marine products with good bioactivity. As shown in Fig. 1, about 972 sulphur-containing alkaloids have been isolated from marine organisms from 1982. (marine fungi have become an important source of sulphur-containing alkaloids in recent 10 years, Fig. 2). The sulphur-containing alkaloids displayed a variety of biological activities such as cytotoxicity, anti-proliferation, anti-virus, anti-inflammatory and antioxidant, as listed in Table 14 (Supporting material) (Berman et al., 1999; Du et al., 2012; Goey et al., 2016; Guzmán et al., 2009; Harris et al., 2018; Jeong et al., 2003; Johnson et al., 1999; Jun et al., 2007; Lam et al., 2020; Lee et al., 2016; Li et al., 2021; Machihara and Namba, 2020; Merrouche et al., 2020; Morgan et al., 2010, 2015; Oluwabusola et al., 2022; Reid et al., 1996; Salam et al., 2013; Susana and Salvador-Reyes, 2022; Wang et al., 2022; Zhao et al., 2019). Of them, ecteinascidin 743 (yondelis) has become the first modern marine drug to treat advanced soft tissue tumors (Menchaca et al., 2003). Thiomarinols have excellent antibacterial activity and can even be effective against methicillin-resistant Staphylococcus aureus (MRSA) (Shiozawa et al., 1995). Somocystinamide A (601) shows strong cytotoxicity to Jurkat and CEM cells with IC50 values of 3 and 14 nM, respectively (Wrasidlo et al., 2008).
In this study, we comprehensively summarized the chemistry and biological activity of sulphur-containing alkaloids in 459 publications and provided a brief analysis of the active conformational relationships between their structure and biological activity. This will help us to provide a reference for the discovery, synthesis and biological activity studies of this class of compounds and for drug discovery and development.
1.1 Search strategy
Comprehensive research and analysis of previously published literature were conducted for studies on the chemical and biological diversity of the marine-derived sulphur-containing alkaloids. The search was conducted using databases such as Sciencedirect, SciFinder, Medline PubMed, Google Scholar, Baidu Scholar, and CNKI by using the keywords such as marine alkaloids, marine-derived sulphur-containing alkaloids, sulphur-containing alkaloids. Furthermore, part of the analyzed studies was got by a manual search of articles in the reference lists of the included studies. The PRISMA template for determining the list of articles is displayed in Fig. 3. The chemical structures were drawn using ChemDraw Professional 20.0.
1.2 Chemical diversity of Marine-Derived Sulphur-containing alkaloids
1.2.1 Marine algae
The photosynthesis of algae is an extremely important source of oxygen. At the same time, the organic matter they produce and the energy they accumulate are the basis for the survival and development of the entire marine biosphere. Therefore, marine algae are considered to be an important marine biological resource. Human exploitation of marine algal resources has a long history. In the early days, some seaweeds such as roundworms, kelp and nori were used as food. Later, seaweed was used as medicine, animal feed and fertiliser. With the development of seaweed resources, one of the most important uses of seaweed is the extraction of various seaweed extracts. For example, agar is widely used as a bacterial culture medium and carrageenan is widely used in the food industry.
Although abundant compounds were isolated from the marine algae by natural product chemists, only 15 sulphur-containing alkaloids (1–15) were reported from red algae and brown algae (Fig. 4 and Table 1). Of them, sulphur-containing alkaloids reported from the red algae are all reported from Laurencia brongniartii (Tanaka et al., 1989). In addition, it’s worth noting that these alkaloids are all indole alkaloids and compounds 4, 8–14 are special indole alkaloid dimers (El-Gamal et al., 2005).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine algae | |||||
| Red algae | |||||
| 1. | itomanindole A | 1989 | Laurencia brongniartii | Okinawa, Japan | (Tanaka et al., 1989) |
| 2. | itomanindole B | 1989 | |||
| 3. | 4,6-dibromo-2-(methylthio)indole | 1989 | |||
| 4. | 3,3-bis(4,6-dibromo-t-methyIthio)indole | 1989 | |||
| 5. | 2-methylsulfinyl-3-methylthio-4,5,6-tribromoindole | 2005 | Ken-Ting National Park, South Taiwan | (El-Gamal et al., 2005) | |
| 6. | 3-methylsulfinyl-2,4,6-tribromoindole | 2005 | |||
| 7. | 4,6-dibromo-2,3-di(methylsulfinyl)indole | 2005 | |||
| 8. | 3,3′-bis(2′-methylsulfinyl-2-methylthio-4,6,4′,6′-tetrabromo)indole | 2005 | |||
| 9. | 3,3-bis(4,6-dibromo-2-methylsulfinyl)indole | 2005 | |||
| 10. | 2,4,4′.6.6′-pentabromo-2′,3-bis(methylthio)-1,3′-bi-1H-indole | 2005 | Kikai Island, Japan | (Natsuki et al., 2005) | |
| 11. | 2.4.4‘0.5′.6.6‘-hexabromo-2′,3-bis(methylthio)-1,3′-bi-1H-indole | 2005 | |||
| 12. | 2,4,4′,5,6,6′-hexabromno-2′,3-bis(methylthio)-1,3′-bi-1H-indole | 2005 | |||
| 13. | 2.4.4‘0.5.5′.6.6′-heptabromo-2′,3-bis(methylthio)-1,3′-bi-1H-indole | 2005 | |||
| 14. | 2.4.4′.6.6′-pentabromo-2′-methylthio-3,3′-bi-1H-indole | 2005 | |||
| Brown algae | |||||
| 15. | sargassulfamide A | 2020 | Sargassum naozhouense | Leizhou Peninsula, Guangdong, China | (Peng et al., 2020) |
1.2.2 Marine fauna
1.2.2.1 Marine sponges
Marine sponges are the most primitive multicellular animal, which have been living in the ocean since 600 million years ago. They have developed to more than 10,000 species, accounting for 1/15 of the marine animal species. Sponges have been developed very early by ancient humans. Now they are extensive used in technology, medicine and daily life and have become an important resource for marine drug development. A total of 316 (16–331) sulphur-containing alkaloids were reported from the marine sponges (Fig. 5 and Table 2). These compounds isolated from marine sponges have various bioactivities such as antitumor, antifungal, antibacterial and enzyme inhibitory activities.
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine fauna | |||||
| Marine sponges | |||||
| 16 | latrunculin A | 1982 | Latruncularia magnifica | Red Sea | (Spector et al., 1983) |
| 17 | latrunculin B | 1982 | |||
| 18 | latrunculin C | 1985 | (Kashman et al., 1985) | ||
| 19 | latrunculin D | 1985 | |||
| 20 | agelasidine B | 1984 | Agefas nakamurai | Okinawa, Japan | (Nakamura et al., 1985) |
| 21 | agelasidine C | 1984 | |||
| 22 | prianosin A | 1987 | Prianos melanos | (Kobayashi et al., 1987) | |
| 23 | psammaplin A | 1987 | Psammaplvsilla sp. | Tonga | (Quiñoà and Crews, 1987) |
| 24 | (E,Z)-isomer of psammaplin A | 1987 | unidentified sponge | Guam, U.S.A. | (Arabshahi and Schmitz, 1987) |
| 25 | bisaprasin | 1987 | Thorectopsamma xana | (Rodriguez et al., 1987) | |
| 26 | mycothiazole | 1988 | Spongia mycofijiensis | Vanuatu | (Crews et al., 1988),(Sugiyama et al., 2003) |
| 27 | dercitin | 1989 | Dercitus sp. | Bahamas | (Burres et al., 1989) |
| 28 | prianosin B | 1988 | Prianos melanos | Motobu Peninsula, Okinawa, Japan | (Cheng et al., 1988) |
| 29 | prianosin C | 1988 | |||
| 30 | prianosin D(discorhabdin D) | 1988 | |||
| 31 | discorhabdin A | 1988 | Latrunculia sp. | New Zealand | (Perry et al., 1988) |
| 32 | discorhabdin B | 1988 | |||
| 33 | adociaquinone A | 1987 | Adocia sp. | Truk Lagoon | (Schmitz and Bloor, 1988) |
| 34 | adociaquinone B | 1987 | |||
| 35 | 3-ketoadociaquinone A | 1987 | |||
| 36 | agelasidine A | 1983 | Agelas sp. | Okinawa, Japan | (Nakamura et al., 1983) |
| 37 | 6,7-epoxy-latrunculin A | 1989 | Latruncularia magnifica | Red Sea | (Blasberger et al., 1989) |
| 38 | latrunculin M | 1989 | |||
| 39 | corallistine | 1989 | Corallistes fulvodesmus | New Caledonia | (Debitus et al., 1989) |
| 40 | batzelline A | 1989 | Batzella sp. | Bahamas | (Sakemi et al., 1989) |
| 41 | batzelline B | 1989 | |||
| 42 | cyclodercitin | 1989 | Dercitus sp. | (Gunawardana et al., 1989) | |
| 43 | nordercitin | 1989 | Stelletta sp. | ||
| 44 | dercitamine | 1989 | |||
| 45 | dercitamide | 1989 | |||
| 46 | isobatzelline A | 1990 | Batzella sp. | Caribbean | (Sun et al., 1990) |
| 47 | isobatzelline B | 1990 | |||
| 48 | isobatzelline D | 1990 | |||
| 49 | neamphine | 1991 | Neamphius huxleyi | Papua New Guinea | (de Silva et al., 1991) |
| 50 | psammaplin B | 1991 | Psammaplysilla purpurea | – | (Jiménez and Crews, 1991) |
| 51 | psammaplin C | 1991 | |||
| 52 | psammaplin D | 1991 | |||
| 53 | prepsammaplin A | 1991 | |||
| 54 | phloeodictine B | 1992 | Phloeodictyon sp. | New Caledonian | (Kourany-Lefoll et al., 1992) |
| 55 | stellettamine | 1992 | Stelletta sp. | – | (Gunawardana et al., 1992) |
| 56 | (9E)-clathridine 9-N-(2-sulfoethyl)-imine | 1992 | Leucetta microraphis | pohnpei | (He et al., 1992) |
| 57 | melemeleone A | 1992 | Dysidea avara | Solomon Islands | (Alvi et al., 1992) |
| 58 | melemeleone B | 1992 | |||
| 59 | (−)-agelasidine C | 1992 | Agelas clathrodes | Puerto Rico | (Morales and Rodríguez, 1992) |
| 60 | (−)-agelasidine D | 1992 | |||
| 61 | dysideathiazole | 1993 | Dysidea herbacea | Pohnpei and Palau | (Unson et al., 1993) |
| 62 | N-methyldysideathiazole | 1993 | |||
| 63 | l0-dechloro-N-methyldysideathiazole | 1993 | |||
| 64 | 10-dechlorodysideathiazole | 1993 | |||
| 65 | 9,l0-adechloro-N-methyldysideathiazo | 1993 | |||
| 66 | potent aldose reductase inhibitor la | 1993 | Dictyodendrilla sp. | Kagoshima, Japan | (Sato et al., 1993) |
| 67 | potent aldose reductase inhibitor lb | 1993 | |||
| 68 | potent aldose reductase inhibitor 2a | 1993 | |||
| 69 | makaluvamine F | 1993 | Zyzzya fuliginosa | Fijian | (Radisky et al., 1993) |
| 70 | 34-O-sulfatobastadin-13 | 1993 | Zanthella sp. | Great Barrier Reef | (Gulavita et al., 1993) |
| 71 | mauritamide A | 1994 | Agelas mauritiana | Fijian | (Jiménez and Crews, 1994) |
| 72 | 6-(p-hydroxyphenyl)–2H-3,4-dihydro-1,1-dioxo-1,4-thiazine | 1994 | Anchinoe tenacior | Mediterranean | (Casapullo et al., 1994) |
| 73 | herbamide A | 1995 | Dysidea herbacea | Papua New Guinea | (Clark and Crews, 1995) |
| 74 | latrunculin S | 1996 | Fasciospongia rimosa | Okinawa, Japan | (Tanaka et al., 1996) |
| 75 | hyrtiomanzamine | 1996 | Hyrtios erecta | Red Sea | (Bourguet-Kondracki et al., 1996) |
| 76 | sagitol | 1996 | Oceanapia sagittaria | Palau | (Salomon and Faulkner, 1996) |
| 77 | 5,5-dichloro-4-methyl-2-[methyl(4,4-dichloro-3-methyl-1-oxobutyl)amino]-N-(thiazol-2-ylmethyl)pentanamide | 1997 | Dysidea herbacea | southern Great Barrier Reef | (Dumdei et al., 1997) |
| 78 | tauroacidin A | 1997 | Hymeniacidon sp. | Okinawa, Japan | (Kobayashi et al., 1997) |
| 79 | tauroacidin B | 1997 | |||
| 80 | thiomycalolide A | 1998 | Mycale sp. | Japan | (Matsunaga et al., 1998) |
| 81 | thiomycalolide B | 1998 | |||
| 82 | kuanoniamine C | 1998 | Oceanapia sp. | Truk, Micronesia. | (Eder et al., 1998) |
| 83 | kuanoniamine D | 1998 | |||
| 84 | N-deacetylkuanoniamine C | 1998 | |||
| 85 | the methylthio derivative isobatzelline B | 1990 | Batzella sp. | Caribbean | (Sun et al., 1990) |
| 86 | discorhabdin Q | 1999 | Latrunculia purpurea, Zyzzya massalis, Zyzzya fuliginosa, and Zyzzya spp. | Assail Bank, between North Island and the Wallab Group, Australia, | (Dijoux et al., 1999) |
| 87 | echinosulfonic acid A | 1999 | Echinodictyum sp. | Great Australian Bight, Southern Australian | (Ovenden and Capon, 1999),(Neupane et al., 2020) |
| 88 | echinosulfonic acid B | 1999 | |||
| 89 | echinosulfonic acid C | 1999 | |||
| 90 | S1319 | 1999 | Dysidea sp. | Okinawa, Japan | (Suzuki et al., 1999) |
| 91 | penarolide sulfate A1 | 2000 | Penares sp. | Japan | (Nakao et al., 2000) |
| 92 | penarolide sulfate A2 | 2000 | |||
| 93 | pateamine | 1991 | Mycale sp. | New Zealand | (Northcote et al., 1991) |
| 94 | (−)-neodysidenin | 2000 | Dysidea herbacea | Great Barrier Reef | (MacMillan et al., 2000) |
| 95 | taurodispacamide A | 2000 | Agelas oroides | The Bay of Naples | (Fattorusso and Taglialatela-Scafati, 2000) |
| 96 | discorhabdin R | 2000 | Latrunculia sp. | the central Prydz channel of Prydz Bay, Antarctica | (Ford and Capon, 2000) |
| Negombata sp. | Victoria, Port Campbell | ||||
| 97 | ianthesine C | 2000 | Ianthella sp. | Australian | (Okamoto et al., 2000) |
| 98 | ianthesine D | 2000 | |||
| 99 | psammaplin A1 | 2000 | Aplysinella rhax | Pohnpei and Palau | (Shin et al., 2000) |
| 100 | psammaplin A2 | 2000 | |||
| 101 | aplysinellin A | 2000 | |||
| 102 | aplysinellin B | 2000 | |||
| 103 | psammaplin A 11′-sulfate | 2000 | Aplysinella rhax | Great Barrier Reef | (Pham et al., 2000) |
| 104 | bisaprasin 11′-sulfate | 2000 | |||
| 105 | wondonin A | 2001 | Poecillastra wondoensisand Japsis sp. | Keomun Island, Korea | (Shin et al., 2001) |
| 106 | wondonin B | 2001 | |||
| 107 | microxine | 2001 | Microxina sp. | Cape Jaffa, Australian | (Killday et al., 2001) |
| 108 | irciniamine | 2002 | Ircinia sp. | Ehime Prefecture, Japan | (Kuramoto et al., 2002) |
| 109 | ancorinolate A | 2002 | Ancorina sp. | Chatham Island,New Zealand | (Meragelman et al., 2002) |
| 110 | ancorinolate B | 2002 | |||
| 111 | bis-ancorinolate B | 2002 | |||
| 112 | ancorinazole | 2002 | |||
| 113 | psammaplin K | 2002 | Aplysinella rhax | Fijian | (Tabudravu et al., 2002) |
| 114 | psammaplin L | 2002 | |||
| 115 | cribronic acid | 2003 | Cribrochalina olemda | Palau | (Sakai et al., 2003) |
| 116 | (2S,4S)-4-sulfooxypiperidine-2-carboxylic acid | 2003 | Stylotella aurantium, andAxinella carteri | Yap State, Micronesia | |
| 117 | dictyodendrin A | 2003 | Dictyodendrilla verongiformis | Nagashima Island, Japan | (Warabi et al., 2003) |
| 118 | dictyodendrin B | 2003 | |||
| 119 | dictyodendrin C | 2003 | |||
| 120 | dictyodendrin D | 2003 | |||
| 121 | dictyodendrin E | 2003 | |||
| 122 | penasulfate A | 2004 | Penares sp. | Hachijo-jima Island,Tokyo, Japan | (Nakao et al., 2004) |
| 123 | spongiacysteine | 2004 | Spongia sp. | Tateyama beach,Chiba Prefecture, Japan | (Kobayashi et al., 2004) |
| 124 | dragmacidonamine A | 2004 | Dragmacidon sp. | Adaman Islands, India | (Pedpradab et al., 2004) |
| 125 | dragmacidonamine B | 2004 | |||
| 126 | 1-methoxydiscorhabdin D | 2004 | Latrunculia bellae | Thunderbolt Reef,Algoa Bay, South Africa | (Antunes et al., 2004) |
| 127 | 1-aminodiscorhabdin D | 2004 | |||
| 128 | discorhabdin G* | 2004 | |||
| 129 | discorhabdin N | 2004 | |||
| 130 | discorhabdin H | 2004 | Strongylodesma algoaensis | ||
| 131 | discorhabdin I | 2004 | Latrunculia brevis | Tierra del Fuego, Patagonia, Argentina | (Reyes et al., 2004) |
| 132 | discorhabdin L | 2004 | |||
| 133 | cribrostatin 7 | 2004 | Petrosia sp. PC00-11–149 | Kalampisauan Island, Philippines | (Sandoval et al., 2004) |
| 134 | bisdemethylaaptamine-9-O-sulfate | 2004 | Aaptos sp. | Bunaken Island, Indonesian | (Herlt et al., 2004) |
| 135 | nagelamide H | 2004 | Agelas sp. | Seragaki Beach, Okinawan | (Endo et al., 2004) |
| 136 | schulzeine A | 2004 | Penares schulzei | Hachijo-kojima Island, Japan | (Takada et al., 2004) |
| 137 | schulzeine B | 2004 | |||
| 138 | schulzeine C | 2004 | |||
| 139 | 1-O-sulfatohemibastadin-1 | 2004 | Ianthella basta | Mangilao, Guam, U.S.A. | (Masuno et al., 2004) |
| 140 | 1-O-sulfatohemibastadin-2 | 2004 | |||
| 141 | 34-O-sulfatobastadin-9 | 2004 | |||
| 142 | 32-O-sulfatobastadin-13 | 2004 | |||
| 143 | hamiguanosinol | 2004 | Mediterranean hamigera | Elba, Mediterranean Sea | (Hassan et al., 2004),(Jamison et al., 2014) |
| 144 | 3-ketoadociaquinone B | 2005 | Xestospongia sp. | Indonesia, Sulawesi | (Cao et al., 2005) |
| 145 | discorhabdin W | 2005 | Latrunculia sp. | New Zealand | (Lang et al., 2005) |
| 146 | discorhabdin G*/I | 2005 | |||
| 147 | echinosulfonic acid D | 2005 | Psammoclemma sp. | New Caledonia | (Rubnov et al., 2005), (Neupane et al., 2020) |
| 148 | gesashidine A | 2005 | An unidentified member of the Thorectidae family | Okinawan | (Iinuma et al., 2005) |
| 149 | halichondria sulfonic acid | 2006 | Halichondria rugosa | South China Sea | (Jin et al., 2006) |
| 150 | latrunculin T | 2006 | Negombata magnifica | Red Sea (near Egypt) | (El Sayed et al., 2006) |
| 151 | (−)-agelasidine A | 2006 | Agelas clathrodes | Curaçao, Caribbean sea | (Medeiros et al., 2006) |
| 152 | dysinosin A | 2002 | a New Genus and Species of Sponge of Dysideidae | Lizard Island, North Queensland, Australia | (Carroll et al., 2002) |
| 153 | mycothiazole-4,19-diol | 2006 | Cacospongia mycofijiensis | Vanuatu | (Sonnenschein et al., 2006) |
| 154 | ircinamine B | 2006 | Dactylia sp. | Cape Sada, Japan | (Sato et al., 2006) |
| 155 | discorhabdin S | 2003 | Batzella sp. | Bimini, Bahamas | (Gunasekera et al., 2003) |
| 156 | discorhabdin T | 2003 | |||
| 157 | discorhabdin U | 2003 | |||
| 158 | 2-debromotaurodispacamide A | 2006 | Axinella verrucosa | Corsica, France | (Aiello et al., 2006) |
| 159 | oxalatrunculin B | 2007 | Negombata corticata | Red Sea (near Egypt) | (Ahmed et al., 2007) |
| 160 | araplysillin-N9-sulfamate | 2007 | Aplysina fulva | Key Largo, Florida | (Rogers and Molinski, 2007) |
| 161 | siphonodictyals B1 | 2007 | Aka coralliphagum | San Salvador, Bahamas | (Grube et al., 2007) |
| 162 | exiguaquinol | 2008 | Neopetrosia exigua | Queensland, Australia | (de Almeida Leone et al., 2008) |
| 163 | CTP-431 | 2008 | Cacospongia mycofijiensis | Beqa Lagoon, Fiji | (Johnson et al., 2008) |
| 164 | latrunculol A | 2008 | (Amagata et al., 2008) | ||
| 165 | latrunculol B | 2008 | |||
| 166 | latrunculol C | 2008 | |||
| 167 | 18-epi-latrunculol A | 2008 | |||
| 168 | latrunculone A | 2008 | |||
| 169 | latrunculone B | 2008 | |||
| 170 | 16-epi-latrunculin B | 2004 | Latruncularia magnifica | Red Sea | |
| 171 | 15-methoxylatrunculin B | 2004 | |||
| 172 | nagelamide K | 2008 | Agelas sp. | Seragaki, Okinawa, Japan | (Araki et al., 2008) |
| 173 | nagelamide M | 2008 | (Kubota et al., 2008) | ||
| 174 | nagelamide N | 2008 | |||
| 175 | ianthesine E | 2008 | Pseudoceratina sp. | Swain Reefs, Australia | (Kalaitzis et al., 2008) |
| 176 | alisiaquinone C | 2008 | An unidentified sponge | New Caledonia | (Desoubzdanne et al., 2008) |
| 177 | phorbasin D | 2008 | Phorbas sp. | Great Australian Bight, South Australia | (Zhang and Capon, 2008) |
| 178 | phorbasin E | 2008 | |||
| 179 | phorbasin F | 2008 | |||
| 180 | (+)-debromodiscorhabdin A | 2009 | Higginsia sp. | South Australia | (El-Naggar and Capon, 2009) |
| 181 | (+)-discorhabdin X | 2009 | |||
| 182 | (−)-dihydrodiscorhabdin A | 2009 | |||
| 183 | (+)-Dihydrodiscorhabdin L | 2009 | Spongosorites sp. | ||
| 184 | (6R,8S)-1-thiomethyldiscorhabdin G*/I | 2009 | Latrunculia wellingtonesis | Wellington, New Zealand | (Grkovic and Copp, 2009) |
| 185 | 16a,17a-dehydrodiscorhabdin W | 2009 | |||
| 186 | nagelamide Q | 2009 | Agelas sp. | Okinawan, Japan | (Araki et al., 2009) |
| 187 | psammaplin I | 2003 | Pseudoceratina purpurea | Papua New Guinea | (Piña et al., 2003) |
| 188 | psammaplin E | 2003 | |||
| 189 | psammaplin F | 2003 | |||
| 190 | psammaplin G | 2003 | |||
| 191 | psammaplin H | 2003 | |||
| 192 | psammaplin J | 2003 | |||
| 193 | 19-oxofasciospongine A | 2009 | Fasciospongia sp. | Palau | (Yao et al., 2009) |
| 194 | fasciospongine C | 2009 | |||
| 195 | fasciospongine A | 2009 | |||
| 196 | fasciospongine B | 2009 | |||
| 197 | callyspongine | 2010 | Callyspongia sp. | South China Sea(Hainan island) | (Huang et al., 2010) |
| 198 | dysideanin A | 2010 | Dysidea sp. | Lingshui County, Hainan, China | (Ren et al., 2010) |
| 199 | (+)-discorhabdin H2 | 2010 | Latrunculia fiordensi | New Zealand | (Grkovic et al., 2010) |
| 200 | (−)-discorhabdin K2 | 2010 | |||
| 201 | (−)-discorhabdin N | 2010 | Latrunculia bellae | ||
| 202 | dihydrodiscorhabdin B | 2010 | Latrunculia sp. | Aleutian Islands, U.S.A. | (Na et al., 2010) |
| 203 | (−)-3-dihydrodiscorhabdin D | 2010 | Sceptrella sp. | Gageodo, Korea | (Jeon et al., 2010) |
| 204 | mauritamide B | 2010 | Agelas linnaei | Peniki East island, ThoU.S.A. nd Islands, Indonesia | (Hertiani et al., 2010) |
| 205 | mauritamide C | 2010 | |||
| 206 | mauritamide D | 2010 | |||
| 207 | baculiferin A | 2010 | Iotrochota baculifera | Hainan island,South China Sea | (Fan et al., 2010) |
| 208 | baculiferin B | 2010 | |||
| 209 | baculiferin C | 2010 | |||
| 210 | baculiferin D | 2010 | |||
| 211 | baculiferin E | 2010 | |||
| 212 | baculiferin F | 2010 | |||
| 213 | baculiferin G | 2010 | |||
| 214 | baculiferin H | 2010 | |||
| 215 | baculiferin I | 2010 | |||
| 216 | baculiferin J | 2010 | |||
| 217 | baculiferin M | 2010 | |||
| 218 | baculiferin O | 2010 | |||
| 219 | psammaplin N | 2010 | Aplysinella rhax | Inner Gneerings Reef, Queensland, Australia | (Graham et al., 2010) |
| 220 | 9-(5′-deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide | 2010 | Trachycladus laevispirulifer | Great Australian Bight, South Australian | (Peng et al., 2010) |
| 221 | amaranzole B | 2010 | Phorbas amaranthus | Dry Reef Rocks, Key Largo, Florida | (Morinaka et al., 2010) |
| 222 | amaranzole C | 2010 | |||
| 223 | amaranzole D | 2010 | |||
| 224 | amaranzole E | 2010 | |||
| 225 | amaranzole F | 2010 | |||
| 226 | nakijinamine C | 2011 | Suberites sp. | Unten Port, Okinawa, Japan | (Takahashi et al., 2011) |
| 227 | nakijinamine D | 2011 | |||
| 228 | xestosaprol N | 2012 | Xestospongia sp. | Weno island, Chuuk State, Federated States of Micronesia | (Lee et al., 2012) |
| 229 | 14-O-sulfate massadine | 2012 | Axinella sp. | Great Australian Bight | (Zhang et al., 2012) |
| 230 | (+)-2-oxo-agelasidine C | 2012 | Agelas mauritiana | Yongxing island,South China Sea | (Yang et al., 2012) |
| 231 | (−)-agelasidine E | 2012 | Agelas citrina | Bahamas | (Stout et al., 2012) |
| 232 | (−)-agelasidine F | 2012 | |||
| 233 | 2-heptadec-11-enamidoethanesulfonic acid | 2013 | Axinella sp. | Hainan island,South China Sea | (Huang et al., 2013) |
| 234 | 2-palmitamidoethanesulfonic acid | 2013 | |||
| 235 | 2-octadec-7-enamidoethanesulfonic | 2013 | |||
| 236 | ciliatamide D | 2013 | Stelletta sp. | Oshimashinsone, Japan | (Imae et al., 2013)，(Takada et al., 2017) |
| 237 | theonezolide A | 2013 | Theonella sp. | Okinawa, Japan | (Nozawa et al., 2013) |
| 238 | theonezolide B | 2013 | |||
| 239 | theonezolide C | 2013 | |||
| 240 | catechol sulfonate | 2013 | Asteropus sp. | Ocean Cay, Bahamas | (Russell et al., 2013) |
| 241 | hyrtimomine D | 2013 | Hyrtios sp. | Kerama island, Okinawa, Japan | (Tanaka et al., 2013c) |
| 242 | hyrtimomine E | 2013 | |||
| 243 | thiaplakortone A | 2013 | Plakortis lita | Tydeman Reef,Queensland, Australia | (Davis et al., 2013) |
| 244 | thiaplakortone B | 2013 | |||
| 245 | thiaplakortone C | 2013 | |||
| 246 | thiaplakortone D | 2013 | |||
| 247 | atkamine A | 2013 | Latrunculia sp. | Aleutian island, Alaska, U.S.A. | (Zou and Hamann, 2013) |
| 248 | nagelamide U | 2013 | Agelas sp. | Kerama islands,Okinawa, Japan | (Tanaka et al., 2013a) |
| 249 | nagelamide V | 2013 | |||
| 250 | nagelamide Y | 2013 | (Tanaka et al., 2013b) | ||
| 251 | nagelamide Z | 2013 | |||
| 252 | reticulatin A | 2013 | Hyrtios reticulatus | N. Sulawesi, Indonesia | (Imada et al., 2013) |
| 253 | reticulatin B | 2013 | |||
| 254 | N-methylmelemeleone-A | 2013 | Dysidea avara | Fethiye, Turkey | (Hamed et al., 2013) |
| 255 | deacyl irciniasulfonic acid C | 2014 | Coscinoderma sp. | Weno island, Chuuk State, Micronesia | (Kim et al., 2014a) |
| 256 | sodium deacyl irciniasulfonate D | 2014 | |||
| 257 | N,N-dimethylguanidium salt | 2014 | |||
| 258 | N,N-dimethyl-1,3-dimethylherbipoline salt | 2014 | |||
| 259 | coscinolactam C | 2014 | |||
| 260 | coscinolactam D | 2014 | |||
| 261 | coscinolactam E | 2014 | |||
| 262 | coscinolactam F | 2014 | |||
| 263 | coscinolactam G | 2014 | |||
| 264 | coscinolactam A | 2009 | Coscinoderma mathewsi | Vangunu Island,Solomon Islands | (De Marino et al., 2009) |
| 265 | coscinolactam B | 2009 | |||
| 266 | glassponsine | 2014 | Anoxycalyx joubini | Trawled, E. Weddell Sea, Antarctica | (Carbone et al., 2014) |
| 267 | hainanerectamine C | 2014 | Hyrtios erecta | Lingshui Bay, China | (He et al., 2014) |
| 268 | hyrtimomine H | 2014 | Hyrtios sp. | Kerama islands,Okinawa, Japan | (Tanaka et al., 2014) |
| 269 | hyrtimomine J | 2014 | |||
| 270 | hyrtimomine K | 2014 | |||
| 271 | callyspongisine A | 2014 | Callyspongia sp. | Great Australian Bight | (Plisson et al., 2014) |
| 272 | callyspongisine B | 2014 | |||
| 273 | tauroacidin C | 2014 | Agelas sp. | Kerama islands,Okinawa, Japan | (Kusama et al., 2014) |
| 274 | tauroacidin D | 2014 | |||
| 275 | 5-epi-nakijiquinone U | 2014 | Dactylospongia metachromia | Ambon, Indonesia | (Daletos et al., 2014) |
| 276 | xestosaprol O | 2014 | Xestospongia vansoesti | Palawan island,Philippines | (Centko et al., 2014) |
| 277 | 2-(3-methyl-dec-3-enamido)ethanesulfonic Acid | 2015 | Callyspongia sp. | Hainan island, China | (Huang et al., 2015) |
| 278 | tauroacidin E | 2015 | Agelas sp. | Kerama island, Okinawa, Japan | (Kusama et al., 2015) |
| 279 | 2-debromonagelamide U | 2015 | (Kenta Nakamura, 2015) | ||
| 280 | citrinamine B | 2015 | Agelas citrina | San Salvador, Bahamas | (Cychon et al., 2015) |
| 281 | melemeleone C | 2015 | Dysidea sp. | Chuuk island, Federated States of Micronesia | (Kim et al., 2015) |
| 282 | melemeleone D | 2015 | |||
| 283 | cycloaurenone A | 2015 | |||
| 284 | xestoadociaminal A | 2015 | Xestospongia sp. | Manado, N. Sulawesi, Indonesia | (He et al., 2015) |
| 285 | xestoadociaminal B | 2015 | |||
| 286 | xestoadociaminal C/D | 2015 | |||
| 287 | xestoadociaquinone A | 2015 | |||
| 288 | xestoadociaquinone B | 2015 | |||
| 289 | seadociaquinone A | 2015 | |||
| 290 | seadociaquinone B | 2015 | |||
| 291 | petroquinone I | 2016 | Petrosia alfiani | Ti Toi, N. Sulawesi, Indonesia | (Tanokashira et al., 2016) |
| 292 | petroquinone J | 2016 | |||
| 293 | petroquinone K | 2016 | |||
| 294 | petroquinone L | 2016 | |||
| 295 | conulothiazole A | 2016 | Smenospongia conulosa | Little Inagua island, Bahamas | (Esposito et al., 2016) |
| 296 | conulothiazole B | 2016 | |||
| 297 | smenothiazole A | 2016 | |||
| 298 | smenothiazole B | 2016 | |||
| 299 | (–)-isowondonin A | 2008 | Poecillastra wondoensis | Keomun Island, Korea | (Chang et al., 2008) |
| 300 | (–)-isowondonin B | 2008 | |||
| 301 | ishigadine A | 2018 | Hyrtios sp. | Ishigaki island, Okinawa, Japan | (Takahashi et al., 2018) |
| 302 | langcoquinone D | 2018 | Spongia sp. | Son Cha, Lang Co, Tha Thien-Hue City, Vietnam | (Ito et al., 2018) |
| 303 | langcoquinone E | 2018 | |||
| 304 | langcoquinone B | 2018 | |||
| 305 | dactylospongin A | 2018 | Dactylospongia sp. | Xisha island,South China Sea | (Li et al., 2018) |
| 306 | dactylospongin B | 2018 | |||
| 307 | ent-melemeleone B | 2018 | |||
| 308 | melemeleone E | 2018 | |||
| 309 | (−)-2-bromo-discorhabdin D | 2019 | Latrunculia biformis | Dredge,Southern Weddell Sea, Antarctica | (Li et al., 2019) |
| 310 | (−)-1-acetyl-discorhabdin L | 2019 | |||
| 311 | (+)-1-octacosatrienoyl-discorhabdin L | 2019 | |||
| 312 | aleutianamine | 2019 | Latrunculia austini | Aleutian Islands, Alaska, U.S.A. | (Zou et al., 2019) |
| 313 | tedanizaine A | 2020 | Tedania sp. | Zhanjiang, Guangdong, China | (Zhang et al., 2020b) |
| 314 | (−)-(1S,2R,6R,8S,6′S)-discorhabdin B dimer | 2020 | Latrunculia biformis | Dredge,Southern Weddell Sea, Antarctica | (Li et al., 2020b) |
| 315 | (−)-(1R,2R,6R,8S,6′S)-16′,17′-dehydrodiscorhabdin B dimer | 2020 | |||
| 316 | (−)-(1R,2R,6R,8S,6′S)-discorhabdin B dimer | 2020 | |||
| 317 | (−)-tridiscorhabdin | 2020 | Dredge,Southern Weddell Sea, Antarctica | (Li et al., 2020c) | |
| 318 | (−)-didiscorhabdin | 2020 | |||
| 319 | psammaplin O | 2020 | Aplysinella rhax | Wainunu, Bua, Fiji island | (Oluwabusola et al., 2020) |
| 320 | psammaplin P | 2020 | |||
| 321 | echinosulfone A | 1999 | Echinodictyum sp. | Great Australian Bight, Southern Australian | (Ovenden and Capon, 1999) |
| 322 | neopetrothiazide | 2021 | Neopetrosia sp. | Helen Reef, Southwest Islands, Palau | (Wang et al., 2021) |
| 323 | tedaniophorbasin A | 2021 | Tedaniophorbas ceratosis | northern New South Wales, Australia. | (Hiranrat et al., 2021) |
| 324 | tedaniophorbasin B | 2021 | |||
| 325 | agelasidine G | 2022 | Agelas nakamurai | Orchid Island, Taiwan | (Lin et al., 2022) |
| 326 | agelasidine H | 2022 | |||
| 327 | agelasidine I | 2022 | |||
| 328 | isoagelasidine B | 2022 | |||
| 329 | 24-methylsulfinyllancoquinone B | 2022 | Spongia pertusa | South China Sea | (Tang et al., 2022) |
| 330 | cyclohexylagelasidine A | 2022 | Agelas nakamurai | Orchid Island, Taiwan | (Fu et al., 2022) |
| 331 | (+)-12-hydroxyagelasidine C | 2022 | Agelas citrina | Cozumel Island, Mexico | (Pech-Puch et al., 2022) |
Among them, discorhabdins, psammaplins and latrunculins are the three noteworthy chemical components. (1) The discorhabdin alkaloids, which have a unique structure with azacarbocyclic spirocyclohexanone and pyrroloiminoquinone units, usually have cytotoxicity against a variety of tumor cells. And when they have a sulfur-containing six-membered ring, discorhabdin alkaloids often have good cytotoxicity (Antunes et al., 2004). Notably, dimers (Lang et al., 2005) and trimers (Li et al., 2020c) of discorhabdin alkaloids, which were reported in recent years, also have good cytotoxicity. (2) Psammaplins are bromotyrosine derivatives with oxime groups and carbon–sulfur bonds. Among them, psammaplin A (23) is the first identified symmetrical bromotyrosine-derived disulfide dimer, which has a broad bioactive spectrum, especially in terms of antimicrobial and antiproliferative activities (Quiñoà and Crews, 1987). (3) Latrunculins, toxins from the red sea sponge Latrunculia magnifica, are concerned as a kind of F-actin-severing compound. Of which, latrunculin A (16) is the most widely used reagent to depolymerize actin filaments in experiments on live cells (Spector et al., 1983).
1.2.2.2 Marine cnidarians
Cnidarians are the most primitive metazoan, which can be divided into three classes: Hydra, Aquarius and Corallus. And with growing bioprospecting efforts and the screening of previously unexplored marine habitats, the phylum cnidarians have been a large, diverse and ecologically important group of marine invertebrates that includes over 11,000 extant species (Rocha et al., 2011).
A total of 21 (332–352) sulphur-containing alkaloids were reported from the marine cnidarians (Fig. 6 and Table 3). Among them, tridentatols E-H are sodium sulfate salt of tridentatols A-D. When potential predators appear, Tridentata marginata will rapidly convert tridentatols E-H to tridentatols A-D, which are nonprotein venom produced by cnidarian nematocysts, and repel the potential predators (Lindquist, 2002).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine cnidarians | |||||
| 332 | tridentatol A | 1996 | Tridentata marginata | Morehead City,North Carolina, USA. | (Lindquist et al., 1996) |
| 333 | tridentatol B | 1996 | |||
| 334 | tridentatol C | 1996 | |||
| 335 | tridentatol D | 2002 | (Lindquist, 2002) | ||
| 336 | tridentatol E | 2002 | |||
| 337 | tridentatol F | 2002 | |||
| 338 | tridentatol G | 2002 | |||
| 339 | tridentatol H | 2002 | |||
| 340 | sinulasulfoxide | 2012 | Sinularia sp. | Manado, North Sulawesi, Indonesia | (Putra et al., 2012) |
| 341 | sinulasulfone | 2012 | |||
| 342 | palyosulfonoceramide A | 2012 | Palythoa caribaeorum andProtopalythoa variabilis | Paracuru beach,Fortaleza, Brazil | (Almeida et al., 2012) |
| 343 | palyosulfonoceramide B | 2012 | |||
| 344 | (+)-4β-N-methenetauryl-10β-methoxy1β,5α,6β,7β-aromadendrane | 2012 | Melitodes squamata | Sanya, Hainan,South China Sea | (Huang et al., 2012) |
| 345 | (−)-4β-N-methenetauryl-10β-methoxy-1β,5β,6α,7α-aromadendrane | 2012 | |||
| 346 | macrophilone B | 2018 | Macrorhynchia philippina | Northwestern Australia | (Yan et al., 2018) |
| 347 | macrophilone C | 2018 | |||
| 348 | macrophilone D | 2018 | |||
| 349 | macrophilone E | 2018 | |||
| 350 | macrophilone F | 2018 | |||
| 351 | macrophilone G | 2018 | |||
| 352 | macrophilone A | 2018 | |||
1.2.2.3 Marine tunicates
Tunicates, which distribute in the world's major seas, are soft-bodied solitary or colonial sessile small marine organisms belonging to the family Ascidiacea under the subphylum Urochordata, phylum Chordata. There’re more than 2,800 species of tunicate species, which are divided into three classes: Ascidiacea, Thaliacea and Appendicularia. Tunicates will lose the notochord and post-anal tail; thus, these organisms are often referred to as the “evolutionary connecting link” between invertebrates and chordates (Ramesh et al., 2021).
158 (353–510) sulphur-containing alkaloids were reported from the marine tunicates (Fig. 7 and Table 4). Among them, eudistomins and ecteinascidins are noteworthy chemical components. (1) Eudistomins attract the attention of scientists because of their good antiviral activity. Subsequent studies have found that eudistomins have the strongest anti-tumor activity when they contain a 1,3,7-oxathiazepine ring. For example, eudistomins C and E, which contain a 1,3,7-oxathiazepine ring, are potent antiviral against RNA viruses (Coxsackie A-21 virus and equine rhinovirus) as well as DNA viruses (HSV-1, HSV-2, and Vaccinia virus). Besides the substituents on the pyridine ring of the β-carboline, the substituents (Br and/or OH) and their positions on the benzenoid ring of the β-carboline may influence the antiviral activity of eudistomins; the order of antiviral activity observed is E (5-Br, 6-OH) > C (6-OH, 7-Br) > L (6-Br). But acetylation of the phenol and primary amine functions of eudistomin C affected a 100-fold reduction in activity (Blunt et al., 1987). (2) Ecteinascidins, a kind of sulphur-containing alkaloids, are marine natural products with potent antitumor activity. These compounds have been a lot of synthetic research and structural modification. Of them, ecteinascidin 743 (yondelis) has been approved by the European Union in October 2007 for the treatment of advanced soft tissue tumors, which became the first modern marine drug (Menchaca et al., 2003).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine tunicates | |||||
| 353 | dendrodoine | 1982 | Dendrodoa grossularia | – | (Heitz et al., 1980) |
| 354 | eudistomin C | 1987 | Eudistoma olivaceum | Caribbean | (Rinehart et al., 1987),(Blunt et al., 1987) |
| 355 | eudistomin E | 1987 | |||
| 356 | eudistomin K | 1987 | |||
| 357 | eudistomin L | 1987 | |||
| 358 | eudistomin F | 1987 | |||
| 359 | citorellamine | 1985 | Polycitorella mariae | Suva, Fiji | (Roll and Ireland, 1985),(Moriarty et al., 1987) |
| 360 | patellazole A | 1988 | Lissoclinum patella | Palau | (Zabriskie et al., 1988) |
| 361 | patellazole B | 1988 | |||
| 362 | patellazole C | 1988 | |||
| 363 | (4-hydroxy-3-methoxyphenyl)(thiazol-2-yl)methanone | 1988 | Aplydium pliciferum | Australian | (Arabshahi and Schmitz, 1988) |
| 364 | 4-(hydroxy(thiazol-2-yl)methyl)-2-methoxyphenol | 1988 | |||
| 365 | shermilamine A | 1988 | Trididemnum sp. | Pago Bay, Guam | (Cooray et al., 1988) |
| 366 | eudistomin K sulfoxide | 1988 | Ritterella sigillinoides | New Zealand | (Lake et al., 1988) |
| 367 | cis-5-hydroxy-4-(4′-hydroxy-3′-methoxyphenyl)-4-(2″-imidazolyl)-1,2,3-trithiane | 1989 | Aplidium sp. | (Copp et al., 1989) | |
| 368 | debromoeudistomin K | 1989 | Ritterella sigillinoides | (Lake et al., 1989) | |
| 369 | shermilamine B | 1989 | Trididemnum sp. | Pago Bay, Guam | (Carroll et al., 1989) |
| 370 | varamine A | 1989 | Lissoclinum vareau | Yasawa island chain, Fiji | (Molinski and Ireland, 1989) |
| 371 | varamine B | 1989 | |||
| 372 | diplamine | 1989 | Diplosomra sp. | Fiji | (Charyulu et al., 1989) |
| 373 | eudistomidin C | 1990 | Eudistoma glaucus | Ie Island, Okinawan,Japan | (Kobayashi et al., 1990) |
| 374 | 6-O-methyleudistomidin C | 1990 | |||
| 375 | ecteinascidin 729 | 1990 | Ecteinascidia turbinata | Caribbean | (Menchaca et al., 2003) |
| 376 | ecteinascidin 743 | 1990 | |||
| 377 | ecteinascidin 745 | 1990 | |||
| 378 | ecteinascidin 770 | 1990 | |||
| 379 | eudistomidin E | 1991 | Eudistoma glaucus | Ie Island, Okinawan,Japan | (Murata et al., 1991) |
| 380 | eudistomidin F | 1991 | |||
| 381 | kuanoniamine A | 1990 | an unidentified Micronesian tunicate | Mante Channel, Pohnpei,Micronesia | (Carroll and Scheuer, 1990) |
| 382 | kuanoniamine B | 1990 | |||
| 383 | lissoclinotoxin B | 1994 | Lissoclinum perforatum | Northern Brittany, France | (Litaudon et al., 1994) |
| 384 | lissoclin A | 1994 | Lissoclinum sp. | Great Barrier Reef | (Searle and Molinski, 1994) |
| 385 | lissoclin B | 1994 | |||
| 386 | benzo-1,3-oxathiazoline | 1994 | |||
| 387 | dehydrokuanoniamine B | 1994 | Cystodytes sp. | Fiji | (McDonald et al., 1994) |
| 388 | shermilamine C | 1994 | |||
| 389 | didemnoline A | 1995 | Didemnum sp. | Rota, Northern Mariana Islands | (Schumacher and Davidson, 1995) |
| 390 | didemnoline B | 1995 | |||
| 391 | didemnoline C | 1995 | |||
| 392 | didemnoline D | 1995 | |||
| 393 | ecteinascidin 597 | 1996 | Ecteinascidia turbinata | Caribbean | (Sakai et al., 1996) |
| 394 | ecteinascidin 583 | 1996 | |||
| 395 | ecteinascidin 594 | 1996 | |||
| 396 | ecteinascidin 596 | 1996 | |||
| 397 | polycarpine | 1996 | Polycarpa clavataPolycarpa aurata | Western AustraliaChuuk, Federated States of Micronesia | (Kang and Fenical, 1996),(Abas et al., 1996) |
| 398 | 4-methoxy-4-(4-methoxyphenyl)-1-methyl-5-thioxoimidazolidin-2-one | 1996 | |||
| 399 | 4-hydroxy-4-(4-methoxyphenyl)-1-methyl-5-thioxoimidazolidin-2-one | 1996 | Polycarpa clavata | Western Australia | (Kang and Fenical, 1996) |
| 400 | N-methyl-(4-methoxyphenyl)-2-oxothioacetamide | 1996 | Polycarpa aurata | Chuuk, Federated States of Micronesia | (Abas et al., 1996) |
| 401 | polycarpine dihydrochloride | 1996 | |||
| 402 | the 20-sulfate of lamellarins T | 1997 | An unidentified ascidian | Arabian Sea (near India) | (Reddy et al., 1997) |
| 403 | the 20-sulfate of lamellarins U | 1997 | |||
| 404 | the 20-sulfate of lamellarins V | 1997 | |||
| 405 | the 20-sulfate of lamellarins Y | 1997 | |||
| 406 | shermilamine D | 1998 | Cystodytes violatinctus | Mayotte lagoon, ComorosIslands, Madagascar | (Koren-Goldshlager et al., 1998) |
| 407 | shermilamine E | 1998 | |||
| 408 | tintamine | 1998 | |||
| 409 | the 20-sulfates of lamellarin B | 1999 | Didemnum chartaceum | Great Barrier Reef | (Davis et al., 1999) |
| 410 | the 20-sulfates of lamellarin C | 1999 | |||
| 411 | the 20-sulfates of lamellarin L | 1999 | |||
| 412 | the 20-sulfates of lamellarin G | 1999 | |||
| 413 | lamellarin α 20-sulfate | 1999 | an unidentified ascidian | Arabian Sea(near Trivandrum, India) | (Reddy et al., 1999) |
| 414 | cycloshermilamine D | 2000 | Cystodytes violatinctus | Mayotte lagoon, ComorosIslands, Madagascar | (Koren-Goldshlager et al., 2000) |
| 415 | (−)-enantiomer | 2001 | Hypsistozoa fasmeriana | New Zealand | (Pearce et al., 2001) |
| 416 | fasmerianamine A | 2001 | |||
| 417 | fasmerianamine B | 2001 | |||
| 418 | 14-methyleudistomidin C | 2001 | Eudistoma gilboverde | Sias Tunnel, Palau | (Rashid et al., 2001) |
| 419 | (2E,4′R,5′S,6′R,7′R,8′S,2′'''E)-3-{8′-hydroxy-4′,6′-dimethyl-4′-(3′'-methylenepent-4′'-enyl)-7′-(-L-mannopyranosyloxy)-[1′,2′,3′]-trithiocan-5′-yl}-N-[4′''-(3′'''-methylsulfanylacryloylamino)-butyl]aerylamide | 2002 | Perophora viridis | Atlantic coast (near North Carolina) | (Řezanka and Dembitsky, 2002) |
| 420 | isodiplamine | 2002 | Lissoclinum notti | Leigh Harbour, Northland, New Zealand | (Appleton et al., 2002) |
| 421 | lissoclinidine | 2002 | |||
| 422 | varacin | 2002 | |||
| 423 | kuanoniamine E | 2002 | an unidentified Singaporean ascidian | Pulau Subar Laut,Singapore | (Nilar et al., 2002) |
| 424 | kuanoniamine F | 2002 | |||
| 425 | ecteinascidin 770 | 2002 | Ecteinascidia thurstoni | Phuket Island, Thai | (Suwanborirux et al., 2002) |
| 426 | ecteinascidin 786 | 2002 | |||
| 427 | ecteinascidin 759B | 2002 | |||
| 428 | conicaquinone A | 2003 | Aplidium conicum | Capo Caccia, Alghero, Italy | (Aiello et al., 2003) |
| 429 | conicaquinone B | 2003 | |||
| 430 | kottamide E | 2003 | Pycnoclavella kottae | New Zealand | (Appleton and Copp, 2003) |
| 431 | shishijimicin A | 2003 | Didemnum proliferum | South Japan | (Oku et al., 2003) |
| 432 | shishijimicin B | 2003 | |||
| 433 | shishijimicin C | 2003 | |||
| 434 | namenamicin | 2003 | |||
| 435 | methylthioadenosine | 2004 | Atriolum robustum | Heron Islands, Wistari Reef, Great Barrier Reef | (Kehraus et al., 2004) |
| 436 | methylsulfinyladenosine | 2004 | |||
| 437 | violatinctamine | 2004 | Cystodytes cf. violatinctus | Kenya | (Chill et al., 2004) |
| 438 | ecteinascidin 731 | 2004 | Ecteinascidia turbinata | Caribbean | (Blunt et al., 2006) |
| 439 | ecteinascidin 745b | 2004 | |||
| 440 | ecteinascidin 808 | 2004 | |||
| 441 | ecteinascidin 815 | 2004 | |||
| 442 | ascidiathiazone A | 2007 | Aplidium sp. | Tom Bowling Bay,Northland, New Zealand | (Pearce et al., 2007) |
| 443 | ascidiathiazone B | 2007 | |||
| 444 | polycarpaurine A | 2007 | Polycarpa aurata | Lembeh Strait, Indonesia | (Wang et al., 2007) |
| 445 | polycarpaurine B | 2007 | |||
| 446 | polycarpaurine C | 2007 | |||
| 447 | nordehydrocyclodercitin | 2007 | Aplidium sp. | Arab Reef, Australia | (Agrawal and Bowden, 2007) |
| 448 | diplamine B | 2008 | Lissoclinum cf. badium | Port Moresby,Papua New Guinea | (Clement et al., 2008) |
| 449 | lissoclinidine B | 2008 | |||
| 450 | isolissoclinotoxin B | 2008 | |||
| 451 | N,N-dimethyl-5-methylvaracin | 2008 | |||
| 452 | leptoclinidamine C | 2009 | Leptoclinides durus | Heron island, Queensland, Australia | (Carroll and Avery, 2009) |
| 453 | N-deacetylshermilamine B | 2010 | Cystodytes dellechiajei | Catalonia, Spain | (Bontemps et al., 2010) |
| 454 | N-deacetylkuanoniamine D | 2010 | |||
| 455 | eudistomidin J | 2011 | Eudistoma glaucus | Ie island, Okinawa, Japan | (Suzuki et al., 2011) |
| 456 | 13-didemethylaminoshermilamine D | 2011 | Cystodytes dellechiajei | Catalonia, Spain | (Bry et al., 2011) |
| 457 | polycarpathiamine A | 2013 | Polycarpa aurata | Ambon, Indonesia | (Pham et al., 2013) |
| 458 | polycarpathiamine B | 2013 | |||
| 459 | duramidine A | 2013 | Leptoclinides durus | Swains Reef, Great Barrier Reef | (Rudolph et al., 2013) |
| 460 | duramidine C | 2013 | |||
| 461 | leptoclinidamine D | 2013 | |||
| 462 | leptoclinidamine E | 2013 | |||
| 463 | leptoclinidamine F | 2013 | |||
| 464 | momusine A | 2013 | Herdmania momus | Jeju island, Korea | (Li et al., 2013) |
| 465 | momusine B | 2013 | |||
| 466 | momusine C | 2013 | |||
| 467 | momusine D | 2013 | |||
| 468 | conthiaquinone A | 2013 | Aplidium conicum | Porto Cesareo, Lecce, Italy | (Menna et al., 2013) |
| 469 | conthiaquinone B | 2013 | |||
| 470 | shermilamine F | 2013 | Cystodytes violatinctus | Solomon islands | (Bontemps et al., 2013) |
| 471 | dehydrokuanoniamine F | 2013 | |||
| 472 | salvadenosine | 2014 | Didemnum sp. | Little San Salvador island, Bahamas | (Jamison et al., 2014) |
| 473 | tanjungide A | 2014 | Diazona cf formosa | East Timor | (Murcia et al., 2014) |
| 474 | tanjungide B | 2014 | |||
| 475 | stolonine A | 2015 | Cnemidocarpa stolonifera | Peel island, Australia | (Tran et al., 2015) |
| 476 | stolonine B | 2015 | |||
| 477 | stolonine C | 2015 | |||
| 478 | sagitol D | 2015 | an unidentified Vietnamese ascidian | PhuQuok, Vietnam | (Utkina, 2015) |
| 479 | lepadin I | 2018 | Didemnum sp. | Stirrup Cay, Bahamas | (Ómarsdóttir et al., 2018) |
| 480 | lepadin J | 2018 | |||
| 481 | lepadin K | 2018 | |||
| 482 | siladenoserinol M | 2018 | Didemnum sp. | Siladen, North Sulawesi, Indonesia | (Torii et al., 2018) |
| 483 | siladenoserinol N | 2018 | |||
| 484 | siladenoserinol O | 2018 | |||
| 485 | siladenoserinol P | 2018 | |||
| 486 | polyaurine B | 2019 | Polycarpa aurata | (Casertano et al., 2019) | |
| 487 | lamellarin K-20-sulfate | 2019 | Didemnum ternerratum | Eua, Kingdom of Tonga | (Bracegirdle et al., 2019) |
| 488 | lamellarin E-20-sulfate | 2019 | |||
| 489 | lamellarin A3-20-sulfate | 2019 | |||
| 490 | lamellarin B1-20-sulfate | 2019 | |||
| 491 | lamellarin D-8-sulfate | 2019 | |||
| 492 | lamellarin B2-20-sulfate | 2019 | |||
| 493 | ireneamide A | 2020 | Cnemidocarpa irene | Oshima-Kojima Islet off the Oshima Peninsula, Hokkaido, Japan | (Miyako et al., 2020) |
| 494 | ireneamide B | 2020 | |||
| 495 | ireneamide C | 2020 | |||
| 496 | 6-biopterin-2′-sulfate | 2020 | |||
| 497 | 6-biopterin-1′-2′-disulfate | 2020 | |||
| 498 | 3-methyl-6-biopterin-2′-sulfate | 2020 | |||
| 499 | siladenoserinol A | 2013 | a tunicate of the family Didemnidae | NorthSulawesi, Indonesia | (Nakamura et al., 2013) |
| 500 | siladenoserinol B | 2013 | |||
| 501 | siladenoserinol C | 2013 | |||
| 502 | siladenoserinol D | 2013 | |||
| 503 | siladenoserinol E | 2013 | |||
| 504 | siladenoserinol F | 2013 | |||
| 505 | siladenoserinol G | 2013 | |||
| 506 | siladenoserinol H | 2013 | |||
| 507 | siladenoserinol I | 2013 | |||
| 508 | siladenoserinol J | 2013 | |||
| 509 | siladenoserinol K | 2013 | |||
| 510 | siladenoserinol L | 2013 | |||
1.2.2.4 Marine echinoderms
Echinoderms are a kind of deuterostomes, which account for up to 90% of benthic biomass in the abyssal seafloor. The common sea stars, sea urchins, sea cucumbers, and sea snake tails all are echinoderms. At present, about 6000 species of echinoderms were widely distributed from shallow sea to thousands of meters deep sea, which can be divided into five classes including Crinoidea, Holothurioidea, Asteroidea, Echinoidea and Ophiuroidea.
22 (511–532) sulphur-containing alkaloids were reported from the marine cnidarians (Fig. 8 and Table 5). Ovothiols are histidine-derived thiols that are receiving great interest for their biological activities in human model systems. Among them, ovothiol A (514) is one of the strongest natural antioxidants (Osik et al., 2021). It’s worth noting that hypalocrinins are the first naturally occurring anthraquinones and anthraquinone biaryls conjugated with taurine. Hypalocrinins A-E (520–524) are five new water-soluble amido- and aminoanthraquinone pigments and hypalocrinin F-G (525–526) are two new amidoanthraquinone biaryls, which all are quite unusual among natural products (Wolkenstein et al., 2019). Likewise, microdiscusols A-F (527–532), six new polyhydroxylated steroids conjugated with taurine, are rare new polyhydroxylated steroids conjugated with taurine (Kicha et al., 2019).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine echinoderms | |||||
| 511 | bis(l-methyl-L-histidin-5-yl)disulphide | 1986 | unfertilized echinoderm eggs | – | (Faulkner, 1986) |
| 512 | bis(Nα.Nα,l-trimethyI-L-histidin-5-yl)disulphide | 1986 | unfertilized echinoderm eggs | ||
| 513 | imbricatine | 1986 | Dermasterias imbricata | – | (Pathirana and Andersen, 1986) |
| 514 | ovothiol A | 1986 | Evasterias troschelii | – | (Turner et al., 1987) |
| 515 | ovothiol C | 1986 | Strongylocentrotus purpuratus | – | |
| 516 | pucherrimine | 2000 | Hemicentrotus pulcherrimus | Japanese sea | (Murata and Sata, 2000) |
| 517 | fisherioside A | 2012 | Leptasterias fisheri | Sakhalin island, Sea of Okhotsk | (Kicha et al., 2012) |
| 518 | curacin E | 2016 | Ophiocoma scolopendrina | Kabira Reef, Ishigaki island, Okinawa, Japan | (Ueoka et al., 2016) |
| 519 | curacin A | 2016 | |||
| 520 | hypalocrinin A | 2019 | Hypalocrinus naresianus | Shima Spur, Kumano-nada Sea, Japan | (Wolkenstein et al., 2019) |
| 521 | hypalocrinin B | 2019 | |||
| 522 | hypalocrinin C | 2019 | |||
| 523 | hypalocrinin D | 2019 | |||
| 524 | hypalocrinin E | 2019 | |||
| 525 | hypalocrinin F | 2019 | |||
| 526 | hypalocrinin G | 2019 | |||
| 527 | microdiscusol A | 2019 | Asterias microdiscus | Eastern part of the Chukchi Sea,Arctic Ocean | (Kicha et al., 2019) |
| 528 | microdiscusol B | 2019 | |||
| 529 | microdiscusol C | 2019 | |||
| 530 | microdiscusol D | 2019 | |||
| 531 | microdiscusol E | 2019 | |||
| 532 | microdiscusol F | 2019 | |||
1.2.2.5 Marine molluscs
Molluscs, a kind of soft marine animal usually with a calcareous shell, are the largest group of animals in the ocean, with more than 100,000 species, more than half of which live in the ocean. Mollusks have 7 classes, including Aplacophora, Bivalvia, Monoplacophora, Polyplacophora, Scaphopoda, Gastropoda and Cephalopoda. These mollusks are widely distributed, from the cold, temperate to tropical, from the highest point of the intertidal zone to 10,000 m deep at the bottom of the ocean.
16 (533–543, 82–83, 369, 381–382) sulphur-containing alkaloids were reported from the marine molluscs (Fig. 9 and Table 6). Notably, pteriatoxins A-C (535–537) are a group of cyclic imine toxins only isolated from Japanese shellfish, which can cause rapid death in mouse (Selwood et al., 2010). Now pteriatoxins have been considered emerging toxins in the European Union and a scientific opinion has been published by the European Food Safety Authority in which an assessment of the risks to human health related to their consumption has been carried out (Moreiras et al., 2020).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine Molluscs | |||||
| 533 | 9-(5-deoxy-5-methylthio-β-D-xylofuranosyl)adenine | 1986 | Extracts of the digestive gland of the dorid nudibranchDoris verrucosa | – | (Faulkner, 1988) |
| 534 | ovothiol B | 1986 | Chlamys hastata | – | (Turner et al., 1987) |
| 369 | shermilamine B | 1990 | Chelynotus semperi | Mante Channel, Pohnpei,Federated States of Micronesia | (Carroll and Scheuer, 1990) |
| 381 | kuanoniamine A | 1990 | |||
| 382 | kuanoniamine B | 1990 | |||
| 82 | kuanoniamine C | 1990 | |||
| 83 | kuanoniamine D | 1990 | |||
| 535 | pteriatoxin A | 2001 | Pteria penguin | Okinawa, Japan | (Takada et al., 2001) |
| 536 | pteriatoxin B | 2001 | |||
| 537 | pteriatoxin C | 2001 | |||
| 538 | the disulfide-linked dimer of 6-bromo-2-mercaptotryptamine | 2003 | Calliostoma canaliculatum | Monterey Bay, California | (Kelley et al., 2003) |
| 539 | iejimalide C | 2006 | Eudistoma cf. rigida | Okinawa, Japan | (Kikuchi et al., 1991) |
| 540 | Iejimalide D | 2006 | |||
| 541 | 11β-hydroxy-N-sulfocarbamoylsaxitoxin | 2008 | Wild mussels (Mytilus edulis andMytilus trossulus) | Eastern Canada coasts | (Dell’Aversano et al., 2008) |
| 542 | 11,11-dihydroxy-N-sulfocarbamoylsaxitoxin | 2008 | |||
| 543 | orbicularisine | 2017 | Codakia orbicularis | Guadeloupe | (Goudou et al., 2017) |
1.2.2.6 Marine bryozoans
Bryozoans are bryophyte-like animals, which had complete digestive apparatus, including the mouth, esophagus, stomach, intestines and anus. The individual bryozoans are small and undivided, with a body cavity. Their bones are formed by a layer of colloid which was secreted in vitro. They can devour microorganisms and organic impurities in water and have a positive effect on water purification.
10 (544–553) sulphur-containing alkaloids were reported from the marine bryozoans (Fig. 10 and Table 7). Perfragilin A (547) and B (545) were isolated from Membranipora perfragilis. As cytotoxic isoquinolines quinone, they contain a relatively uncommon thiomethyl ether functionality. And Both perfragilin A and B were toxic to murine leukemia cells (P388), with perfragilin B being considerably more potent: ED50= 0.8 and 0.07 μg/ml, respectively (Choi et al., 1993).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine Bryozoans | |||||
| 544 | 1-ethyl-4-methylsulfone-β-carboline | 1991 | Cribricellina cribraria | New Zealand | (Prinsep et al., 1991) |
| 545 | perfragilin B | 1993 | Membranipora perfragilis | Rapid Bay, South Australia | (Choi et al., 1993) |
| 546 | 2-methyl-6-methylthioisoquinoline-3,5,8(2H)trione | 1993 | Blflustra perfragilis | Bass Strait | (Blackman et al., 1993) |
| 547 | perfragilin A | 1993 | Membranipora perfragilis | Rapid Bay, South Australia | (Choi et al., 1993) |
| 548 | euthyroideone A | 1998 | Euthyroides episcopalis | Fiordland, New Zealand | (Morris and Prinsep, 1998) |
| 549 | euthyroideone B | 1998 | |||
| 550 | euthyroideone C | 1998 | |||
| 551 | N-(2-[6-bromo-2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]ethyl)-N-methy-lmethanesulfonamide | 2002 | Flustra foliacea | “Steingrund”, North Sea, Helgoland, Germany | (Peters et al., 2002) |
| 552 | flustramine R | 2020 | Flustra foliacea | Iceland | (Di et al., 2020) |
| 553 | orthoscuticelline E | 2020 | Orthoscuticella ventricosa | Korora beach, Coffs Harbour, NSW, Australia | (Kleks et al., 2020) |
1.2.2.7 Other marine animals
22 (554–575) sulphur-containing alkaloids were reported from other marine animals (Fig. 11 and Table 8). Of them, nebulosins A-P (560–575) were reported from the northeastern Atlantic marine terebellid Eupolymnia nebulosa. It’s worth noting that nebulosins feature an unprecedented highly substituted thiolane ring leading to up to four contiguous chiral centers (Calabro et al., 2020).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Other marine animals | |||||
| 554 | L-ovithiol A | 1999 | Platynereis dumerilii | – | (Röhl et al., 1999) |
| 555 | 2-n-octylpyrrole sulfamate | 2003 | Cirriformia tentaculata | Florida | (Barsby et al., 2003) |
| 556 | 2-n-heptylpyrrole sulfamate | 2003 | |||
| 557 | 2-n-hexylpyrrole sulfamate | 2003 | |||
| 558 | thelepamide | 2014 | Thelepus crispus | Friday Harbor, WA, U.S.A. | (Rodríguez et al., 2014) |
| 559 | cypridina luciferyl sulfate | 2014 | Vargula hilgendorfii | Chita, Aichi, Japan | (Nakamura et al., 2014) |
| 560 | nebulosin A | 2020 | Eupolymnia nebulosa | Intertidal area of Corranroo, West coast of Ireland | (Calabro et al., 2020) |
| 561 | nebulosin B | 2020 | |||
| 562 | nebulosin C | 2020 | |||
| 563 | nebulosin D | 2020 | |||
| 564 | nebulosin E | 2020 | |||
| 565 | nebulosin F | 2020 | |||
| 566 | nebulosin G | 2020 | |||
| 567 | nebulosin H | 2020 | |||
| 568 | nebulosin I | 2020 | |||
| 569 | nebulosin J | 2020 | |||
| 570 | nebulosin K | 2020 | |||
| 571 | nebulosin L | 2020 | |||
| 572 | nebulosin M | 2020 | |||
| 573 | nebulosin N | 2020 | |||
| 574 | nebulosin O | 2020 | |||
| 575 | nebulosin P | 2020 | |||
1.3 Marine microorganism
1.3.1 Dinoflagellates
Dinoflagellates are a group of single cells with double flagella, whose shape is variable. They have both plant and animal characteristics, which could perform photosynthesis and move by the rotation of two flagella. Dinoflagellates are widely distributed, especially in tropical oceans. When the light and water temperature are appropriate, dinoflagellates can multiply in a short period of time to become the main feed of marine animals.
13 (576–588) sulphur-containing alkaloids were reported from dinoflagellates (Fig. 12 and Table 9). Among them, compounds 576–585 are thought as the carbamoyl-N-sulfo derivatives of saxitoxin and neosaxitoxin (Hall et al., 1984). In addition, it’s worth noting that symbioimine (586) and neosymbioimine (587) both have a characteristic 6,6,6-tricyclic iminium ring structure and an aryl sulfate moiety. And the plausible biogenetic pathway of them can be explained by an intramolecular Diels-Alder reaction followed by imine cyclization (Kita et al., 2005).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Dinoflagellates | |||||
| 576 | toxin B1 | 1984 | Protugonyaulax catenella | Northeast Pacific | (Hall et al., 1984) |
| 577 | toxin B2 | 1984 | |||
| 578 | toxin C1 | 1984 | |||
| 579 | toxin C2 | 1984 | |||
| 580 | toxin C3 | 1984 | |||
| 581 | toxin C4 | 1984 | |||
| 582 | GTX-1 | 1984 | |||
| 583 | GTX-2 | 1984 | |||
| 584 | GTX-3 | 1984 | |||
| 585 | GTX-4 | 1984 | |||
| 586 | symbioimine | 2004 | Symbiodinium sp. | Sesoko Island, Okinawa, Japan. | (Kita et al., 2004) |
| 587 | neosymbioimine | 2005 | (Kita et al., 2005) | ||
| 588 | ovataline | 2022 | Ostreopsis cf. ovata | Kimyong, Jeju island | (Lee et al., 2022) |
1.3.2 Cyanobacteria
Cyanobacteria, also known as blue-green algae, are large, single-celled prokaryotes with a long evolutionary history. They have chlorophyll which enabled them to perform oxygen-producing photosynthesis. The photosynthesis of cyanobacteria is also thought as the reason why the earth's atmosphere develops from an anaerobic state to an aerobic state. At present, there are about 2000 species of cyanobacteria, which are mainly divided into two classes: Chroococcus and Phytoplankton. As highly adaptable organisms, they are widely distributed in all kinds of natural water bodies, soil and some organisms, even in the rock surface and other harsh environments.
41 (589–627, 61, 519) sulphur-containing alkaloids were reported from cyanobacteria (Fig. 13 and Table 10). Curacins A-D (519, 591–592 and 594) are toxic metabolites isolated from the cyanobacteria, which are thought of as antimitotic agents. In addition, lyngbyabellins are a kind of depsipeptide derivatives, whose typical structural features are two thiazole rings and a chlorinated 2-methyloctanoate residue (Choi et al., 2012). They generally display various activities such as cytotoxicity, antimalarial, and antifouling activities (Fathoni et al., 2020). Lyngbyabellins O (613) and P (614) both exhibit strong antifouling activity, which may be related to the fact that compounds don’t have a side chain (Petitbois et al., 2017). Notably, aulosirazoles A-C (623–625) are the structurally unique isothiazolonaphthoquinone aulosirazole, which possess selective antitumor cytotoxicity. Although its mechanism of action is unknown, biological evaluation of them identified one potential target as the immunoregulatory enzyme indoleamine-2,3-dioxygenase (IDO) (Blunt et al., 2015).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Cyanobacteria | |||||
| 589 | cylindrospermopsin | 1992 | Cylindrospermopsis raciborskii | Palm Island, Queensland, Australia | (Ohtani et al., 1992) |
| 590 | 13-demethylisodysidenin | 1993 | Oscillatoria spongeliae | – | (Faulkner, 1995) |
| 591 | curacin B | 1995 | Lyngbya majuscula | Curaçao, Caribbean sea | (Yoo and Gerwick, 1995) |
| 592 | curacin C | 1995 | |||
| 593 | barbamide | 1996 | (Orjala and Gerwick, 1996) | ||
| 519. | curacin A 519 | 1998 | Virgin Islands, British | (Márquez et al., 1998) | |
| 594 | curacin D | 1998 | |||
| 595 | kalkitoxin | 2000 | Curaçao, Caribbean sea | (Yokokawa et al., 2004) | |
| 596 | dechlorobarbamide | 2000 | (Sitachitta et al., 2000) | ||
| 597 | pseudodysidenin | 2001 | Lyngbya majuscula | Boca del Drago Beach, Bocas del Toro, Panama | (Jiménez and Scheuer, 2001) |
| 598 | nordysidenin | 2001 | |||
| 599 | dysidenin | 2001 | |||
| 600 | isodysidenin | 2001 | |||
| 61. | dysideathiazole 61 | 2001 | |||
| 601 | somocystinamide A | 2002 | Lyngbya majuscula andSchizothrix sp. | Fijian | (Nogle and Gerwick, 2002) |
| 602 | lyngbyabellin D | 2003 | Lyngbya sp. | Guam, U.S.A. | (Williams et al., 2003) |
| 603 | lyngbyabellin E | 2005 | Lyngbya majuscula | Alotau Bay, Papua New Guinea | (Han et al., 2005) |
| 604 | lyngbyabellin F | 2005 | |||
| 605 | lyngbyabellin G | 2005 | |||
| 606 | lyngbyabellin H | 2005 | |||
| 607 | lyngbyabellin I | 2005 | |||
| 608 | dolabellin | 2005 | |||
| 609 | herbamide B | 2010 | Bocas del Toro, Panama | (Balunas et al., 2010) | |
| 610 | hectochlorin B | 2015 | Moorea producens | – | (Paul and Boudreau, 2015) |
| 611 | hectochlorin C | 2015 | |||
| 612 | hectochlorin D | 2015 | |||
| 613 | lyngbyabellin O | 2017 | Okeania sp. | Algetah Alkabira reef, Jeddah, Saudi Arabia | (Petitbois et al., 2017) |
| 614 | lyngbyabellin P | 2017 | |||
| 615 | trichothiazole A | 2017 | Trichodesmium sp. | Gulf of Mexico | (Belisle et al., 2017) |
| 616 | laucysteinamide A | 2017 | Caldora penicillata | Lau Lau Bay, Saipan | (Zhang et al., 2017a) |
| 617 | aranazole A | 2018 | Fischerella sp. PCC 9339 | – | (Moosmann et al., 2018) |
| 618 | aranazole B | 2018 | |||
| 619 | aranazole C | 2018 | |||
| 620 | aranazole D | 2018 | |||
| 621 | isoconulothiazole B | 2019 | Trichodesmium sp. | Mayaguana Island, Bahamas | (Teta et al., 2019) |
| 622 | conulothiazole C | 2019 | |||
| 623 | aulosirazole A | 2022 | Nostoc sp. UIC 10771 | Reykjavık, Iceland | (Davis et al., 2022) |
| 624 | aulosirazole B | 2022 | |||
| 625 | aulosirazole C | 2022 | |||
| 626 | caldorazole | 2022 | Caldora sp. | Ishigaki Island, Okinawa, Japan | (Ohno et al., 2022) |
| 627 | iezoside | 2022 | Leptochromothrix valpauliae | Ie Island, Okinawa, Japan, | (Kurisawa et al., 2022) |
1.3.3 Marine bacteria
Marine bacteria are the most important members of marine microorganisms, which are widely distributed and abundant in the ocean. The common bacteria include Pseudomonas, Vibrio, Achromobacter, Nocardia and Streptomyces. Almost all known bacteria can be found in the marine environment. Meanwhile, most marine bacteria are decomposers, which play an important role in the whole process of marine material decomposition and transformation. Moreover, because the deep-sea environment has the characteristics of high salt, high pressure, low temperature and low nutrition, the physiological and ecological characteristics of deep-sea bacteria are very different from those of terrestrial bacteria. This is also the reason why scientists are paying more attention to deep-sea bacteria.
110 (628–737) sulphur-containing alkaloids were reported from marine bacteria (Fig. 14 and Table 11). Notably, thiomarinols are a kind of naturally occurring double‐headed antibiotic, whose structure comprises two antimicrobial subcomponents, pseudomonic acid analogue and holothin, linked by an amide bond (Dunn et al., 2015). Such ingredients usually have excellent antibacterial activity and can even be effective against MRSA (Shiozawa et al., 1995). And sulfadixiamycins A-C (685–687), sulfonyl‐bridged alkaloid dimers, are isolated from recombinant Streptomyces species. They have both aromatic sulfonamide and diarylsulfone substructures. In addition, sungeidines A-H (724–731), a class of microbial secondary metabolites with unique structural features, are likely to be assembled from two octaketide chains following processing by oxygenases/oxidases and cyclases.
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine bacteria | |||||
| 628 | thiomarinol A(Thiomarinol) | 1993 | Alteromonas raw sp. nov. SANK 73390 | – | (Shiozawa et al., 1993) |
| 629 | thiomarinol B | 1995 | (Shiozawa et al., 1995) | ||
| 630 | thiomarinol C | 1995 | |||
| 631 | 1,2-diacyl-3-α-d-glucuronopyranosyl-sn-glycerol taurineamide | 1996 | Hyphomonas jannaschiana | – | (Batrakov et al., 1996) |
| 632 | cyclo(L-Pro-L-Met) | 1996 | Pseudomonas aeruginosa | Ross Island, Antarctica | (Jayatilake et al., 1996) |
| 633 | thiomarinol D | 1997 | Alteromonas raw sp. nov. SANK 73390 | – | (Shiozawa et al., 1997) |
| 634 | thiomarinol E | 1997 | |||
| 635 | thiomarinol F | 1997 | |||
| 636 | thiomarinol G | 1997 | |||
| 637 | B-90063 | 1998 | Blastobacter sp. SANK 71894 | Japan | (Sachiko Takaishi et al., 1998) |
| 638 | agrochelin | 1999 | Agrobacterium sp. | – | (Cañedo et al., 1999) |
| 639 | bacillamide A | 2011 | Bacillus sp. | Masan Bay, Korea. | (Zou et al., 2011) |
| 640 | petrobactin sulfonate | 2004 | Marinobacter hydrocarbonoclasticus | – | (Hickford et al., 2004) |
| 641 | gliocladin A | 2004 | Gliocladium sp. | Coast of Kata, Wakayama Prefecture, Japan | (Yoshihide Usami, 2004) |
| 642 | gliocladin B | 2004 | |||
| 643 | glioperazine | 2004 | |||
| 644 | 2,5-dimethyl-3-(methylsulfanyl) pyrazine | 2005 | Alphaproteobacteria Loktanella sp. | North Sea | (Dickschat et al., 2005) |
| 645 | N-propionyl-desacetyl-mycothiol | 2008 | MAR2 strain CNQ703 | Guam | (Newton et al., 2008) |
| 646 | lodopyridone | 2009 | Saccharomonospora sp. | La Jolla, California | (Maloney et al., 2009) |
| 647 | neobacillamide A | 2009 | Bacillus vallismortis | Sanya island, South China Sea | (Yu et al., 2009) |
| 648 | bacillamide C | 2009 | |||
| 649 | ammosamide A | 2009 | Streptomyces sp. | Bahamas | (Hughes et al., 2009) |
| 650 | pulicatin A | 2010 | Streptomyces sp. | Mactan island, Cebu, Philippines | (Lin et al., 2010) |
| 651 | pulicatin B | 2010 | |||
| 652 | pulicatin C | 2010 | |||
| 653 | pulicatin D | 2010 | |||
| 654 | pulicatin E | 2010 | |||
| 655 | aerugine | 2010 | |||
| 656 | pulicatin F | 2010 | |||
| 657 | pulicatin G | 2010 | |||
| 658 | watasemycin A | 2010 | |||
| 659 | watasemycin B | 2010 | |||
| 660 | bacillamide B | 2009 | Bacillus endophyticus | Sanya island, South China Sea | (Yu et al., 2009),(Sun et al., 2015) |
| 661 | benzoxacystol | 2011 | Streptomyces griseus | deep sea sediment, Canary Basin | (Nachtigall et al., 2011) |
| 662 | erythrazole A | 2011 | Erythrobacter sp. | Trinity Bay, Galveston, Texas, U.S.A. | (Hu and MacMillan, 2011) |
| 663 | erythrazole B | 2011 | |||
| 664 | heronamycin A | 2012 | Streptomyces sp. | Heron island, Queensland, Australia | (Raju et al., 2012) |
| 665 | cyanosporaside F | 2013 | Streptomyces sp. | Bahamas | (Lane et al., 2013) |
| 666 | (−)-homoseongomycin | 2013 | Salinispora pacifica DPJ-0019 | – | (Woo et al., 2013) |
| 667 | nitrosporeusine A | 2013 | Streptomyces nitrosporeus | Arctic Chukchi Sea | (Yang et al., 2013) |
| 668 | nitrosporeusine B | 2013 | |||
| 669 | tetroazolemycin A | 2013 | Streptomyces olivaceus | southwest Indian Ocean | (Liu et al., 2013) |
| 670 | tetroazolemycin B | 2013 | |||
| 671 | forazoline A | 2014 | Actinomadura sp. WMMB-499 | Florida, U.S.A. | (Wyche et al., 2014) |
| 672 | forazoline B | 2014 | |||
| 673 | dermacozine J | 2014 | Dermacoccus abyssi | Challenger Deep, Mariana Trench | (Wagner et al., 2014) |
| 674 | echoside D | 2014 | Streptomyces sp. | Jimei, China | (Deng et al., 2014) |
| 675 | echoside E | 2014 | |||
| 676 | anithiactin A | 2014 | Streptomyces sp. | Jaebu island, South Korea | (Kim et al., 2014b) |
| 677 | anithiactin B | 2014 | |||
| 678 | anithiactin C | 2014 | |||
| 679 | streptcytosine B | 2014 | Streptomyces sp. | Iriomote island, Japan | (Bu et al., 2014) |
| 680 | collismycin B | 2014 | |||
| 681 | SF2738 C | 2014 | |||
| 682 | spithioneine A | 2015 | Streptomyces spinoverrucosus | Bahamas | (Fu and MacMillan, 2015a) |
| 683 | spithioneine B | 2015 | |||
| 684 | N-acetyl-S-(((1R,2S,3S,4aS,8aS)-2,3-dihydroxy-5,5,8a-trimethyl-1-((E)-3-methylpenta-2,4-dien-1-yl)decahydronaphthalen-2-yl)methyl)-L-cysteine | 2015 | Streptomyces sp. | Parangipettai, India | (Shanthi et al., 2015) |
| 685 | sulfadixiamycin A | 2015 | Streptomyces sp. | – | (Baunach et al., 2015) |
| 686 | sulfadixiamycin B | 2015 | |||
| 687 | sulfadixiamycin C | 2015 | |||
| 688 | thiasporine A | 2015 | Actinomycetospora chlora | Vava’u, Tonga | (Fu and MacMillan, 2015b),(Seitz et al., 2016) |
| 689 | thiasporine B | 2015 | |||
| 690 | thiasporine C | 2015 | |||
| 691 | ulbactin F | 2016 | Brevibacillus sp. | Ohtsuchi, Iwate, Japan | (Igarashi et al., 2016) |
| 692 | ulbactin G | 2016 | |||
| 693 | 4-(1H-indol-3-yl-sulfanyl)phenol | 2016 | Vibrio splendidus | S. Orkney island | (Nair et al., 2016) |
| 694 | N-isobutylmethanesulfinamide | 2017 | Salinispora pacifica | Fiji | (Harig et al., 2017) |
| 695 | N-isopentylmethanesulfinamide | 2017 | |||
| 696 | 3-acetylamino-N-2-thienyl-propanamide | 2017 | Streptomyces sp. Q24 | Zhuhai, Guangdong, China | (Ye et al., 2017) |
| 697 | holomycin | 2017 | Streptomyces sp. DT-A37 | Dongtou, Wenzhou, Zhejiang Province, P. R. China | (Ding et al., 2017) |
| 698 | (1Z)-S,S'-dimethyldihydroholomycin | 2017 | |||
| 699 | holomycin A | 2017 | |||
| 700 | streptopertusacin A | 2017 | Streptomyces sp. HZP-2216E | Turtle Islet located,South China Sea | (Zhang et al., 2017b) |
| 701 | lodopyridone B | 2017 | Saccharomonospora sp. | La Jolla Submarine Canyon, California | (Le et al., 2017) |
| 702 | lodopyridone C | 2017 | |||
| 703 | 8-hydroxythiomarinol C | 2017 | Pseudoalteromonas sp. | – | (Gao et al., 2017) |
| 704 | 6,7-diketothiomarinol C | 2017 | |||
| 705 | 6,7-diketothiomarinol A | 2017 | |||
| 706 | 7-ketothiomarinol C | 2017 | |||
| 707 | 7-ketothiomarinol A | 2017 | |||
| 708 | 8-epi-7-ketothiomarinol C | 2017 | |||
| 709 | 8-epi-7-ketothiomarinol A | 2017 | |||
| 710 | 8-epi-7-epi-6-ketothiomarinol A | 2017 | |||
| 711 | 1-methyl-4-methylthio-β-carboline | 2017 | Pseudomonas benzenivorans | California State Beaches | (Lorig-Roach et al., 2017) |
| 712 | (2-(3-hydroxyquinolin-2-yl)oxazole-4-carbonyl)-L-cysteine | 2018 | Streptomyces cyaneofuscatus M−157 | Avilés Canyon, Cantabrian Sea | (Ortiz-López et al., 2018) |
| 713 | (2R,2′R)-3,3′-disulfanediylbis(2-(2-(3-hydroxyquinolin-2-yl)oxazole-4-carboxamido)propanoic acid) | 2018 | |||
| 714 | thymidine-3-mercaptocarbamic acid | 2019 | Streptomyces sp. | Red Sea | (Shaala et al., 2019) |
| 715 | thymidine-3-thioamine | 2019 | |||
| 716 | nocarterphenyl A | 2019 | Nocardiopsis sp. OUCMDZ-4936 | Dongzhaigang Mangrove Reserve, China | (Wang et al., 2019) |
| 717 | nocarterphenyl B | 2019 | |||
| 718 | nocarterphenyl D | 2021 | Nocardiopsis sp. HDN154086 | South China Sea | (Chang et al., 2021) |
| 719 | 2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene | 2019 | Streptomyces sp. G278 | Cu Lao Cham - Quang Nam, Vietnam | (Cao et al., 2019a) |
| 720 | questiomycin C | 2019 | Alteromonas sp. D | Hiroshima-bay, Hiroshima, Japan | (Umetsu et al., 2019) |
| 721 | questiomycin D | 2019 | |||
| 722 | mindapyrrole B | 2019 | Pseudomonas aeruginosa | Sultan Kudarat, Mindanao, Philippines | (Lacerna et al., 2019) |
| 723 | mindapyrrole C | 2019 | |||
| 671 | forazoline A | 2020 | Actinomadura sp. WMMB-499 | – | (Zhang et al., 2020a) |
| 724 | sungeidine A | 2020 | Micromonospora sp. | Sungei Buloh Wetland Reserve, Singapore | (Low et al., 2020) |
| 725 | sungeidine B | 2020 | |||
| 726 | sungeidine C | 2020 | |||
| 727 | sungeidine D | 2020 | |||
| 728 | sungeidine E | 2020 | |||
| 729 | sungeidine F | 2020 | |||
| 730 | sungeidine G | 2020 | |||
| 731 | sungeidine H | 2020 | |||
| 732 | monathioamide A | 2020 | Pseudomonas sp. ZZ820R | Zhoushan Archipelago, Zhejiang, China | (Yi et al., 2020a) |
| 733 | levesquamide | 2020 | Streptomyces sp. RKND-216 | Burnt Point, PE, Canada | (Liang et al., 2020) |
| 734 | streptothiazomycin A | 2020 | Streptomyces sp. SY1965 | Mariana Trench | (Yi et al., 2020b) |
| 735 | thiolopyrrolone A | 2022 | Streptomyces sp. BTBU20198885 | Xiamen, China | (Song et al., 2022) |
| 736 | 2,2-dioxidothiolutin | 2022 | |||
| 737 | thiolutin | 2022 | |||
1.3.4 Marine fungi
The distribution of fungi in the ocean mainly depended on the distribution of hosts. According to their habitat habits, marine fungi could be divided into four basic ecological types: (1) woody fungi. The largest number and most widely distributed higher fungi in marine waters is saprophytic life. (2) Parasitic algae fungi. It accounted for about 1/3 of the number of marine fungal species, most of which were ascomycetes. (3) Seaweed fungi. The number of seaweed fungi was small and mostly inhabited the leaves. (4) Parasitic animal fungi. Only parasitic in the exoskeleton and shell. Marine fungi participate in the decomposition of marine organic matter and the regeneration of inorganic nutrients and continuously provide effective nutrition for marine plants.
197 (738–934) sulphur-containing alkaloids were reported from marine fungi (Fig. 15 and Table 12). It’s worth noting that leptosins, amphiepicoccins (912–921), penicisulfuranols (869–874), gliotoxins and chetracins E, F, C (875, 876, 877) all are epipolythiodioxopiperazines (ETPs) which are a class of biologically active fungi secondary metabolites characterized by a unique bridged disulfide or polysulfide dioxopiperazine six-membered ring (Gardiner et al., 2005). These compounds occur in many fungi. And due to their broad spectra of bioactivities, ETPs have drawn wide attention in recent years (Jiang and Guo, 2011). Moreover, graphiumins A-J (814–823), rostratins A-D (767–770), aranotins (777, 781–783, 904) and eutypellazines A-S (849–866) all are thiodiketopiperazine alkaloids. Among them, eutypellazines N-P (861–863) are characteristic of unique spirocyclic skeletons. Meanwhile, eutypellazines N-O bearing a spirocyclic tetrahydro- benzothiophene motif is found in wide-type fungus for the first time (Niu et al., 2017b). In summary, thiodioxopiperazines are the main type of sulphur-containing alkaloids in fungi.
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Marine fungi | |||||
| 738 | leptosin A | 1994 | Leptosphueriu sp. | Tanabe Bay, Japan | (Takahashi et al., 1994) |
| 739 | leptosin B | 1994 | |||
| 740 | leptosin C | 1994 | |||
| 741 | leptosin D | 1994 | |||
| 742 | leptosin E | 1994 | |||
| 743 | leptosin F | 1994 | |||
| 744 | leptosin G | 1995 | (Takahashi et al., 1995b) | ||
| 745 | leptosin G1 | 1995 | |||
| 746 | leptosin G2 | 1995 | |||
| 747 | leptosin H | 1995 | |||
| 748 | leptosin K | 1995 | (Takahashi et al., 1995a) | ||
| 749 | leptosin K1 | 1995 | |||
| 750 | leptosin K2 | 1995 | |||
| 751 | 11,11′-dideoxyverticillin A | 1999 | Penicillium sp. CNC-350 | – | (John, 1999) |
| 752 | 11′-deoxyverticillin A | 1999 | |||
| 753 | flavochristamide A | 2000 | Flavobacterium sp. | lshikari Bay, Hokkaido | (Kohayashi et al., 1995) |
| 754 | flavochristamide B | 2000 | |||
| 755 | leptosin M | 2002 | Leptosphaeria sp. | Tanabe Bay, Japan | (Yamada et al., 2002) |
| 756 | leptosin M1 | 2002 | |||
| 757 | leptosin N | 2002 | |||
| 758 | leptosin N1 | 2002 | |||
| 759 | fusaperazine A | 2002 | Fusarium chlamydosporum | – | (Blunt et al., 2004) |
| 760 | fusaperazine B | 2002 | |||
| 761 | Sch 54,794 | 1993 | (Chu et al., 1993) | ||
| 762 | Sch 54,796 | 1993 | |||
| 763 | leptosin O | 2004 | Leptosphaeria sp. | Tanabe Bay, Japan | (Takeshi Yamada, 2004) |
| 764 | leptosin P | 2004 | |||
| 765 | leptosin Q | 2004 | |||
| 766 | leptosin R | 2004 | |||
| 767 | rostratin A | 2004 | Exserohilum rostratum | Lanai Island, Hawaii | (Tan et al., 2004) |
| 768 | rostratin B | 2004 | |||
| 769 | rostratin C | 2004 | |||
| 770 | rostratin D | 2004 | |||
| 771 | dehydroxybisdethiobis(methylthio)gliotoxin | 2006 | Pseudallescheria sp. | Uljin, Gyeongbuk, Korea | (Li et al., 2006) |
| 772 | bilain A | 2007 | Penicillium bilaii | Huon estuary, Tasmania | (Capon et al., 2007) |
| 773 | bilain B | 2007 | |||
| 774 | bilain C | 2007 | |||
| 775 | (Z)-6-benzylidene-3-hydroxymethyl-1,4-dimethyl-3-methylsulfanylpiperazine-2,5-dione | 2008 | Order Pleosporales CRIF2 | Surin Island | (Prachyawarakorn et al., 2008) |
| 776 | alternarosin A | 2009 | Alternaria raphani | Qingdao, China | (Wang et al., 2009) |
| 777 | bisdethiobis(methylthio)acetylaranotin | 2009 | |||
| 778 | plectosphaeroic acid A | 2009 | Plectosphaerella cucumerina | Barkley Sound, British Columbia | (Carr et al., 2009) |
| 779 | plectosphaeroic acid B | 2009 | |||
| 780 | plectosphaeroic acid C | 2009 | |||
| 781 | deoxyapoaranotin | 2011 | Arthrinium versicolor | East Sea, Korea | (Choi et al., 2011) |
| 782 | acetylaranotin | 2011 | |||
| 783 | acetylapoaranotin | 2011 | |||
| 784 | luteoalbusin A | 2012 | Acrostalagmus luteoalbus | South China Sea | (Wang et al., 2012a) |
| 785 | luteoalbusin B | 2012 | |||
| 786 | T988A | 2012 | |||
| 787 | gliocladines C | 2012 | |||
| 788 | gliocladines D | 2012 | |||
| 789 | chetoseminudin B | 2012 | |||
| 790 | chetoseminudin C | 2012 | |||
| 791 | spirogliotoxin | 2012 | Aspergillus fumigatus YK-7 | Yingkou, China | (Wang et al., 2012b) |
| 792 | gliotoxin | ||||
| 793 | bisdethiobis(methylthio)gliotoxin | ||||
| 794 | didehydrobisdethiobis(methylthio)gliotoxin | ||||
| 795 | bis(dethio)-10a-methylthio-3a-deoxy-3,3a-didehydrogliotoxin | 2012 | Penicillium sp. | Suruga Bay, Japan | (Sun et al., 2012) |
| 796 | 6-deoxy-5a,6-didehydrogliotoxin | 2012 | |||
| 797 | bis(dethio)bis(methylthio)-5a,6-didehydrogliotoxin | 2012 | |||
| 798 | 5a,6-didehydrogliotoxin | 2012 | |||
| 799 | gliotoxin G | 2012 | |||
| 800 | penilumamide | 2014 | Aspergillus sp. | Xisha islands,South China Sea | (Reddy et al., 2017) |
| 801 | penilumamide B | 2014 | |||
| 802 | penilumamide C | 2014 | |||
| 803 | reduced gliotoxin | 2014 | Neosartorya pseudofischeri | Hainan Sanya National Coral Reef Reserve, China | (Liang et al., 2014) |
| 804 | acetylgliotoxin | ||||
| 805 | bis-N-norgliovictin | ||||
| 806 | 6-acetylbis(methylthio)gliotoxin | ||||
| 807 | chartarutine C | 2014 | Stachybotrys chartarum | Beibuwan Bay, China | (Li et al., 2014) |
| 808 | chartarutine D | 2014 | |||
| 809 | cladosporin A | 2015 | Cladosporium sp. | Yangshashan Bay, Ningbo, Zhejiang, China | (Gu et al., 2015) |
| 810 | cladosporin B | 2015 | |||
| 811 | 6-acetylmonodethiogliotoxin | 2015 | Dichotomomyces cejpii | Bare island, Sydney, Australia | (Harms et al., 2015) |
| 812 | 6-acetylbisdethiobis(methylthio)gliotoxin | 2015 | |||
| 813 | 5a,6-anhydrobisdethiobis(methylthio)-gliotoxin | 2015 | |||
| 814 | graphiumin A | 2015 | Graphium sp. | Ishigaki island, Okinawa, Japan | (Fukuda et al., 2015) |
| 815 | graphiumin B | 2015 | |||
| 816 | graphiumin C | 2015 | |||
| 817 | graphiumin D | 2015 | |||
| 818 | graphiumin E | 2015 | |||
| 819 | graphiumin F | 2015 | |||
| 820 | graphiumin G | 2015 | |||
| 821 | graphiumin H | 2015 | |||
| 822 | graphiumin I | 2015 | |||
| 823 | graphiumin J | 2015 | |||
| 824 | adametizine A | 2015 | Penicillium adametzioides | Hainan island, China | (Liu et al., 2015b) |
| 825 | adametizine B | 2015 | |||
| 826 | peniciadametizine A | 2015 | Penicillium adametzioides | Wenchang, Hainan, China | (Liu et al., 2015c) |
| 827 | peniciadametizine B | 2015 | |||
| 828 | pseudellone A | 2015 | Pseudallescheria ellipsoidea F42 − 3 | National Coral Reef Reserve, Hainan, China | (Liu et al., 2015a) |
| 829 | pseudellone B | 2015 | |||
| 830 | stachybotrin G | 2015 | Stachybotrys chartarum MXH-X73 | Xisha island, China | (Ma et al., 2015) |
| 831 | DC1149B | 2015 | Trichoderma cf. brevicompactum | Palau | (Yamazaki et al., 2015a) |
| 832 | iododithiobrevamide | 2015 | |||
| 833 | DC1149R | 2015 | |||
| 834 | chlorotrithiobrevamide | 2015 | (Yamazaki et al., 2015b) | ||
| 835 | acetylgliotoxin G | 2015 | Dichotomomyces cejpii | Pecém’s offshore port, Ceará, Brazil | (Rodrigues et al., 2015) |
| 836 | acaromyester A | 2016 | Acaromyces ingoldii | South China Sea | (Gao et al., 2016) |
| 837 | dichotocejpin A | 2016 | Dichotomomyces cejpii FS110 | South China Sea | (Fan et al., 2016) |
| 838 | pretrichodermamide D | 2016 | Penicillium sp. KMM 4672 | Vietnam, South China Sea | (Yurchenko et al., 2016) |
| 839 | pretrichodermamide E | 2016 | |||
| 840 | pretrichodermamide F | 2016 | |||
| 841 | pseuboydone C | 2016 | Pseudallescheria boydii | Hainan Sanya National Coral Reef Reserve, China | (Lan et al., 2016) |
| 842 | pseuboydone D | 2016 | |||
| 843 | lasiodipline F | 2016 | Pseudallescheria ellipsoidea F42-3 | (Wang et al., 2016) | |
| 844 | pseudellone D | 2016 | |||
| 845 | dithioaspergillazine A | 2016 | Trichoderma cf. brevicompactum | Palau | (Yamazaki et al., 2016) |
| 846 | dichocerazine A | 2017 | Dichotomomyces cejpii F31-1 | Hainan Sanya National Coral Reef Reserve, China | (Chen et al., 2017b) |
| 847 | dichocerazine B | 2017 | |||
| 848 | haematocin | 2017 | |||
| 849 | eutypellazine A | 2017 | Eutypella sp. MCCC 3A00281 | South Atlantic Ocean | (Niu et al., 2017a) |
| 850 | eutypellazine B | 2017 | |||
| 851 | eutypellazine C | 2017 | |||
| 852 | eutypellazine D | 2017 | |||
| 853 | eutypellazine E | 2017 | |||
| 854 | eutypellazine F | 2017 | |||
| 855 | eutypellazine G | 2017 | |||
| 856 | eutypellazine H | 2017 | |||
| 857 | eutypellazine I | 2017 | |||
| 858 | eutypellazine J | 2017 | |||
| 859 | eutypellazine K | 2017 | |||
| 860 | eutypellazine L | 2017 | |||
| 861 | eutypellazine N | 2017 | (Niu et al., 2017b) | ||
| 862 | eutypellazine O | 2017 | |||
| 863 | eutypellazine P | 2017 | |||
| 864 | eutypellazine Q | 2017 | |||
| 865 | eutypellazine R | 2017 | |||
| 866 | eutypellazine S | 2017 | |||
| 867 | gliomastin B | 2017 | Gliomastix sp. | Ain El-Sokhna, Eygpt | (Elnaggar et al., 2017) |
| 868 | scedapin C | 2017 | Scedosporium apiospermum | Hainan Sanya National Coral Reef Reserve, China | (Huang et al., 2017) |
| 869 | penicisulfuranol A | 2017 | Penicillium janthinellum HDN13-309 | Hainan, China | (Zhu et al., 2017) |
| 870 | penicisulfuranol B | 2017 | |||
| 871 | penicisulfuranol C | 2017 | |||
| 872 | penicisulfuranol D | 2017 | |||
| 873 | penicisulfuranol E | 2017 | |||
| 874 | penicisulfuranol F | 2017 | |||
| 875 | chetracin E | 2018 | Acrostalagmus luteoalbus HDN13-530 | Liaodong Bay, China | (Yu et al., 2018) |
| 876 | chetracin F | 2018 | |||
| 877 | chetracin C | 2018 | |||
| 878 | altenusinoide A | 2018 | Alternaria sp. SCSIOS02F49 | Xuwen County, Guangdong, China | |
| 879 | altenusinoide B | 2018 | |||
| 880 | methyl 2-(6-hydroxybenzothiazol-4-yl) acetate | 2018 | |||
| 881 | violaceimide A | 2018 | Aspergillus violaceus | South China Sea | (Yin et al., 2018) |
| 882 | violaceimide B | 2018 | |||
| 883 | violaceimide C | 2018 | |||
| 884 | violaceimide D | 2018 | |||
| 885 | violaceimide E | 2018 | |||
| 886 | geospallin A | 2018 | Geosmithia pallida FS140 | (Sun et al., 2018) | |
| 887 | geospallin B | 2018 | |||
| 888 | geospallin C | 2018 | |||
| 889 | (+)-acrozine A | 2019 | Acrostalagmus luteoalbus TK-43 | Sinop, Turkey | (Cao et al., 2019b) |
| 890 | (–)-acrozine A | 2019 | |||
| 891 | (+)-acrozine B | 2019 | |||
| 892 | (–)-acrozine B | 2019 | |||
| 893 | acrozine F | 2021 | (Cao et al., 2021) | ||
| 894 | acrozine G | 2021 | |||
| 895 | dechdigliotoxin A | 2019 | Dichotomomyces cejpii | South China Sea | (Liu et al., 2019b) |
| 896 | dechdigliotoxin B | 2019 | |||
| 897 | dechdigliotoxin C | 2019 | |||
| 898 | fusaperazine F | 2019 | Penicillium crustosum HDN153086 | Prydz Bay, Antarctica | (Liu et al., 2019a) |
| 899 | pseudboindole B | 2019 | Pseudallescheria boydii F44-1 | Hainan Sanya National Coral Reef Reserve, China | (Yuan et al., 2019) |
| 900 | emestrin L | 2020 | Aspergillus terreus | Weizhou coral reefs, South China Sea | (Wu et al., 2020) |
| 901 | emestrin M | 2020 | |||
| 902 | emethacin C | 2020 | |||
| 903 | emethacin B | 2020 | |||
| 904 | bisdethiobis(methylsulfanyl)acetylapoaranotin | 2020 | |||
| 905 | spiroepicoccin A | 2020 | Epicoccum nigrum | – | (Li et al., 2020d) |
| 906 | 7-dehydroxyepicoccin H | 2020 | Epicoccum nigrum SD-388 | Western Pacific | (Chi et al., 2020b) |
| 907 | 7-hydroxyeutypellazine F | 2020 | |||
| 908 | 5′-hydroxy-6′-ene-epicoccin G | 2020 | (Chi et al., 2020a) | ||
| 909 | 7-methoxy-7′-hydroxyepicoccin G | 2020 | |||
| 910 | 8′-acetoxyepicoccin D | 2020 | |||
| 911 | 7′-demethoxyrostratin C | 2020 | |||
| 912 | amphiepicoccin A | 2020 | Epicoccum nigrum HDN17-88 | Western Pacific | (Wang et al., 2020) |
| 913 | amphiepicoccin B | 2020 | |||
| 914 | amphiepicoccin C | 2020 | |||
| 915 | amphiepicoccin D | 2020 | |||
| 916 | amphiepicoccin E | 2020 | |||
| 917 | amphiepicoccin F | 2020 | |||
| 918 | amphiepicoccin G | 2020 | |||
| 919 | amphiepicoccin H | 2020 | |||
| 920 | amphiepicoccin I | 2020 | |||
| 921 | amphiepicoccin J | 2020 | |||
| 922 | citriperazine A | 2020 | Penicillium sp. KMM 4672 | South China Sea | (Yurchenko et al., 2020) |
| 923 | citriperazine B | 2020 | |||
| 924 | citriperazine C | 2020 | |||
| 925 | scetryptoquivaline A | 2020 | Scedosporium apiospermum F41-1 | Hainan Sanya National Coral Reef Reserve, China | (Li et al., 2020a) |
| 926 | 5-epi-pretrichodermamide A | 2020 | Trichoderma cf. brevicompactum | Palau | (Yamazaki et al., 2020) |
| 927 | 5-epi-trithiopretrichodermamide A | 2020 | |||
| 928 | pensulfonamide | 2021 | Penicillium aculeatum | Red Sea (Egypt) | (Hawas et al., 2022) |
| 929 | secoemestrin C | 2021 | Aspergillus quadrilineatus FJJ093 | Jeju Island, Republic of Korea | (Hwang et al., 2021) |
| 930 | emestrin | 2021 | |||
| 931 | emestrin B | 2021 | |||
| 932 | talaromanloid A | 2022 | Talaromyces mangshanicus BTBU20191089 | – | (Zhang et al., 2022) |
| 933 | ochraceopetalin | 2021 | Aspergillus ochraceopetaliformis | – | (Park et al., 2021b) |
| 934 | aspergillazine A | 2005 | Spicaria elegans | Jiaozhou Bay, China | (Liu et al., 2005) |
1.3.5 Mangroves bacteria, fungi and other marine microorganism
Mangrove is a special ecosystem for the transition from land to sea. In recent years, mangrove bacteria and fungi have gradually become the focus of research. 2 (935–936) and 34 (937–968, 767, 909) sulphur-containing alkaloids were reported from mangroves bacteria and fungi, respectively. Brocazines A-F (937–942), phomazines A-C (943–945), epicorazines A-C (946–948), penicibrocazines A-E (955–959) and penispirozines A-D (964–967) all are thiodiketopiperazines alkaloids. Moreover, epicoccins A-E (949–953) are epipolythiodioxopiperazines. This shows that thiodioxopiperazines are the main type of sulphur-containing alkaloids in fungi again. Notably, spirobrocazines A-B (961–962) are characteristic of a unique spirocyclic skeleton (Meng et al., 2016) and penispirozine B (965) possesses a 6/5/6/5/6 pentacyclic ring system with two rare spirocyclic centers (Zhu et al., 2020). In addition, penispirozine A (964) has an unusual pyrazino[1,2]oxazadecaline coupled with a thiophane ring system and trichodermamide G (968) has a similar cyclic system. In addition, 4 (969–972) sulphur-containing alkaloids, new pigments with an unprecedented skeleton, were reported from marine ciliates Pseudokeronopsis riccii (Fig. 16 and Table 13).
| No. | Compounds | Time | From | Location | Ref. |
|---|---|---|---|---|---|
| Mangroves bacteria | |||||
| 935 | 9-((2R,3R,4S,5S)-3,4-dihydroxy-5-((methylthio)methyl)tetrahydrofuran-2-yl)-6-hydroxy-9H-purin-3-ium | 2014 | Micromonospora sp. K310 | Butre river, Ghana | (Kyeremeh et al., 2014) |
| 936 | bagremycin C | 2017 | Streptomyces sp. Q22 | Qiao Mangrove Forest, Zhuhai City, Guangdong, China | (Chen et al., 2017a) |
| Mangroves fungi | |||||
| 937 | brocazine A | 2014 | Penicillium brocae MA-231 | Hainan island, China | (Meng et al., 2014) |
| 938 | brocazine B | 2014 | |||
| 939 | brocazine C | 2014 | |||
| 940 | brocazine D | 2014 | |||
| 941 | brocazine E | 2014 | |||
| 942 | brocazine F | 2014 | |||
| 943 | phomazine A | 2014 | Phoma sp. OUCMDZ-1847 | Wenchang, China | (Kong et al., 2014) |
| 944 | phomazine B | 2014 | |||
| 945 | phomazine C | 2014 | |||
| 946 | epicorazine A | 2014 | |||
| 947 | epicorazine B | 2014 | |||
| 948 | epicorazine C | 2014 | |||
| 949 | epicoccin A | 2014 | |||
| 950 | epicoccin B | 2014 | |||
| 951 | epicoccin C | 2014 | |||
| 952 | epicoccin D | 2014 | |||
| 953 | epicoccin E | 2014 | |||
| 954 | exserohilone A | 2014 | |||
| 767. | rostratin A | 2014 | |||
| 955 | penicibrocazine A | 2015 | Penicillium brocae | Hainan island, China | (Meng et al., 2015) |
| 956 | penicibrocazine B | 2015 | |||
| 957 | penicibrocazine C | 2015 | |||
| 958 | penicibrocazine D | 2015 | |||
| 959 | penicibrocazine E | 2015 | |||
| 960 | analog | 2015 | |||
| 961 | spirobrocazine A | 2016 | Penicillium brocae MA-231 | (Meng et al., 2016) | |
| 962 | spirobrocazine B | 2016 | |||
| 963 | brocazine G | 2016 | |||
| 964 | penispirozine A | 2020 | Penicillium janthinellum HDN13-309 | (Zhu et al., 2020) | |
| 965 | penispirozine B | 2020 | |||
| 966 | penispirozine C | 2020 | |||
| 967 | penispirozine D | 2020 | |||
| 968 | trichodermamide G | 2020 | Trichoderma harzianum D13 | (Zhao et al., 2020) | |
| 909. | aspergillazine A | 2020 | |||
| Other marine microorganism | |||||
| 969 | keronopsamide B | 2010 | Pseudokeronopsis riccii | Tyrrhenian Coast, Sardinia, Italy | (Guella et al., 2010) |
| 970 | keronopsamide C | 2010 | |||
| 971 | keronopsin A1 | 2010 | |||
| 972 | keronopsin A2 | 2010 | |||
1.4 Bioactivities of Marine-Derived Sulphur-containing alkaloids
The biological activities of marine-derived sulphur-containing alkaloids have been studied extensively. As listed in Table 14, marine-derived sulphur-containing alkaloids had a broad range of bioactive properties including cytotoxicity, antibacteria, antifungi, antimitotic, antiviral, and other activities.
In summary, while research on the biological activity of marine sulphur-containing alkaloids has explored a wide range of directions, the primary focus remains on their cytotoxicity against tumour cells. Over the past four decades, numerous compounds with potent cytotoxic properties have been discovered, displaying strong efficacy against various types of tumour cells. Here, we have summarized the compounds with superior activity according to the type of tumour they target.
1.5 Cytotoxicity
1.5.1 Leukemia
Leukemia is a collection of malignant tumours that affect the blood system. Clonal leukemia cells undergo uncontrolled proliferation and accumulate in the bone marrow and other haematopoietic tissues due to impaired differentiation, apoptosis, and other mechanisms, ultimately inhibiting normal haematopoietic function. (Whiteley et al., 2021). Several marine sulphur-containing alkaloids have demonstrated cytotoxicity against different types of leukemia cells. For instance, prianosin A (22), C (29), D (30), varamine A (370), B (371), diplamine (372), and eudistomidin J (455) exhibited IC50 values of 0.037, 0.15, 0.18, 0.03, 0.05, 0.02, and 0.047 μg/ml, respectively, against L1210 cells. (Kobayashi et al., 1987; Cheng et al., 1988; Molinski and Ireland, 1989; Charyulu et al., 1989; Suzuki et al., 2011). Similarly, compounds such as discorhabdin B (32), discorhabdin W (145), (6R,8S)-1-thiomethyldiscorhabdin G*/I (184), 16a,17a-dehydrodiscorhabdin W (185), discorhabdin G*/I (146), discorhabdin A (31), dercitin (27), curacin E (518), agrochelin (638), eudistomidin J (455), pateamine (93) have been reported to inhibit P388 cells with IC50 values of 0.084, 0.087, 0.28, 0.45, 0.6, 0.13, 0.11, 0.081, 0.02, 0.053 µM and 43, 0.15 ng/ml, respectively. (Lang et al., 2005; Grkovic and Copp, 2009; Burres et al., 1989; Suzuki et al., 2011; Northcote et al., 1991; Ueoka et al., 2016; Cañedo et al., 1999). Meanwhile, compounds such as perfragilins B (545), leptosin A (738), B (739), C (740), D (741), E (742), F (743), G (744), G1 (745), G2 (746), H (747), K (748), K1 (749) and K2 (750), N (757), N1 (758) and P (764) exhibited EC50 values of 70, 1.85, 2.40, 1.75, 86, 46, 56, 4.6, 4.3, 4.4, 3.0, 3.8, 2.2, 2.1 180, 190 and 100 ng/ml, respectively, against P388 cells. (Choi et al., 1993; Takahashi et al., 1994; Takahashi et al., 1995b; Takahashi et al., 1995a; Yamada et al., 2002; Takeshi Yamada, 2004). Among them, shishijimicin A (431), B (432), C (433) and namenamicin (434) have shown excellent cytotoxicity against P388 cells with IC50 values of 0.47, 2.0, 1.7 and 3.3 pg/ml, respectively. (Oku et al., 2003).
Moreover, chetracin E (875) exhibited IC50 values of 0.4 μM against K562 cells. (Yu et al., 2018). Moreover, somocystinamide A (601) and 14-methyleudistomidin C (418) exhibited IC50 values of 60 nM and 0.57 μg/ml against Molt4 cells, and compound 601 also inhibited CEM cells with an IC50 of 14 nM. (Wrasidlo et al., 2008; Rashid et al., 2001). It is worth noting that dercitin (27) demonstrated cytotoxicity against HL-60 and HL-60/AR cells by reducing DNA replication, with IC50 values of 0.15 and 0.24 μM, respectively. (Burres et al., 1989). Meanwhile, somocystinamide A (601) exhibited cytotoxicity against Jurkat cells with an IC50 value of only 3 nM. (Wrasidlo et al., 2008).
1.5.2 Lymphomas
Lymphomas are a heterogeneous group of malignant tumors that originate from the lymphatic hematopoietic system. Although these tumors typically arise in the lymph nodes, the distribution of the lymphatic system allows them to spread throughout the body and invade nearly any tissue or organ. (Jiang et al., 2017). Prianosin A (22), C (29), and D (30) exhibited strong cytotoxicity against L5178Y cells with IC50 values of 0.014, 0.024, and 0.048 μg/mL, respectively. (Kobayashi et al., 1987; Cheng et al., 1988).
1.5.3 Colorectal cancer
Colorectal cancer is a prevalent malignant tumor that includes colon and rectal cancers. Tumor cells can metastasize to lymph nodes through lymphatic vessels or to the liver, lungs, and bones through the bloodstream. The primary treatment regimen is currently a combination of chemotherapy, with chemotherapeutic agents such as 5-fluorouracil, oxaliplatin, irinotecan, and other drugs. (Biller et al., 2021). HCT116 cells are a commonly used in vitro model of colorectal cancer. Discorhabdin A (31), (-)-(1R,2R,6R,8S,6′S)-discorhabdin B dimer (316), latrunculone A (168), patellazole A (360), B (361), C (362), acetylgliotoxin (804), reduced gliotoxin (803), chetracin E (875), C (877), epicorazine A (946) and rostratin C (769) have been reported to inhibit HCT116 cells with IC50 values of 7, 160, 480, 0.62, 0.39, 4.7, 0.66, 0.62, 5.6, 890, 430, 400, 300, 330 nM and 0.76 μg/ml, respectively. (Antunes et al., 2004; Li et al., 2020b; Amagata et al., 2008; Richardson et al., 2005; Liang et al., 2014; Liang et al., 2014; Yu et al., 2018; Tan et al., 2004). In addition, compound 360, 361 and 362 also exhibited IC50 values of 0.66, 0.62 and 5.6 nM against HCT 116 cells p53–/–. Meanwhile, discorhabdin I (131), L (132), tanjungide A (473), agrochelin (638), dercitin (27), latrunculin A (16), ecteinascidin 743 (376), 729 (375), 597 (393), 583 (394) and 594 (395) exhibited cytotoxicity against HT-29 cells with GI50 values of 0.35, 0.12 and 0.19 µM and IC50 values of 0.268, 0.063 µM, 60, 0.5, 0.5, 2.0, 10 and 25 ng/ml, respectively. (Reyes et al., 2004; Murcia et al., 2014; Cañedo et al., 1999; Burres et al., 1989; Longley et al., 1993; Sakai et al., 1996).
RKO cells and COLO-205 cells are two other in vitro cellular models of colon cancer. A study showed that gliotoxin (792) and reduced gliotoxin (803) were cytotoxic to RKO cells (IC50 values of 0.8 and 0.41 µM, respectively), while 14-methyleudistomidin C (418) was cytotoxic to COLO-205 cells (IC50= 0.42μg/ml). (Liang et al., 2014; Rashid et al., 2001).
1.5.4 Pancreatic cancer
Pancreatic cancer is a highly prevalent malignant disease of the gastrointestinal tract with a very low survival rate. Patients with untreated pancreatic cancer typically have a survival time of approximately four months. (Park et al., 2021a). In vitro studies have shown that discorhabdin T (156), U (157), and DC1149B (831) are effective inhibitors of PANC-1 cells, with IC50 values of 0.7, 0.069 and 0.02 µM, respectively. (Gunasekera et al., 2003; Tang et al., 2020).
1.5.5 Breast cancer
Breast cancer is a common malignant tumor that affects women. It occurs due to the uncontrolled proliferation of epithelial cells in the breast, influenced by various carcinogenic factors. Common early symptoms include breast lumps, nipple discharge, and swollen lymph nodes in the armpits, while in advanced stages, cancer cells can metastasize to distant organs, leading to life-threatening multi-organ lesions. (Harbeck et al., 2019). Kuanoniamine C (82) and A (381) have demonstrated cytotoxicity against MCF-7 cells with GI50 values of 0.81 and 0.12 nM, respectively, as well as against MDA-MB-231 cells with GI50 values of 10.23 and 0.73 nM, respectively. (Kijjoa et al., 2007). Curacin A (519), B (591), D (594), Luteoalbusin A (784), B (785), T988A (786), Gliocladine C (787) and D (788) were reported to inhibit MCF-7 cells with IC50 values of 0.038, 0.32, 0.34, 0.23, 0.25, 0.91, 0.23, and 0.65 µM, respectively. (Verdier-Pinard et al., 1998; Márquez et al., 1998; Wang et al., 2012a).
1.5.6 Lung cancer
Lung cancer is a malignant tumor that originates in the lining or glands of the bronchi in the lungs. It is one of the fastest-growing malignancies in terms of morbidity and mortality and poses a serious threat to public health. Currently, there are two main classifications of lung cancer: small cell lung cancer and non-small cell lung cancer, which can be further divided into adenocarcinoma, squamous cell carcinoma, large cell carcinoma, bronchoalveolar carcinoma, and others depending on the pathology. (Hirsch et al., 2017). Several compounds have been reported to inhibit lung cancer cell growth. Dercitin (27), somocystinamide A (601), ecteinascidin 743 (376), latrunculin A (16), ecteinascidin 729 (375), 597 (393), 583 (394), 594 (395), agrochelin (638), chetracin E (875), and C (877) have been reported to inhibit A549 cells with IC50 of 7, 160, 480, 0.62, 0.39, 4.7, 0.66, 0.62, 5.6, 890, 430, 400, 300, 330 nM and 0.76 μg/ml, respectively. (Burres et al., 1989; Wrasidlo et al., 2008; Simoens et al., 2003; Longley et al., 1993; Sakai et al., 1996; Cañedo et al., 1999; Yu et al., 2018). Lyngbyabellin E-I (603–607) have also been shown to inhibit NCI-H460 cells, with IC50 values ranging from 0.2 to 2.2 µM. (Williams et al., 2003). Meanwhile, kuanoniamine C (82) and A (381) demonstrated cytotoxicity against MCF-7 cells, with GI50 values of 0.81 and 0.12 nM, respectively. (Kijjoa et al., 2007). Additionally, Chetracin E (875) and C (877) exhibited IC50 values of 0.2 and 0.8 μM, respectively, against NCI-H1975 cells. (Yu et al., 2018). Notably, compound 376 showed significant inhibition of NCI-H292 cells with an IC50 value of 1.1 nM. (Simoens et al., 2003).
1.5.7 Cervical cancer
Cervical cancer is a prevalent malignancy in women, and persistent high-risk HPV infection is a well-established major risk factor for the disease. More than 90% of cervical cancers are associated with high-risk HPV infection. (Cohen et al., 2019). In vitro, Hela cells are widely used as a model for cervical cancer. Among tested compounds, iejimalide C (539), caldorazole (626), and iezoside (627) exhibited IC50 values of 2.7, 23, and 6.8 nM, respectively, against HeLa cells. Compound 626 also inhibited HeLa S3 and HeLa S3Mer- cells, with IC50 values of 44 and 48 nM, respectively. (Kazami et al., 2014; Ohno et al., 2022; Kurisawa et al., 2022). Notably, shishijimicin A (431), B (432), C (433), and namenamicin (434) showed excellent cytotoxicity against HeLa cells, with IC50 values of 1.8, 3.3, 6.3, and 43 pg/ml, respectively. (Oku et al., 2003).
1.5.8 Melanoma
Melanoma is a highly malignant tumor that develops from melanocytes commonly found in the skin. Due to its aggressive nature, melanoma is prone to infiltrative growth and metastasis, making it one of the deadliest types of skin cancer. (Schadendorf et al., 2018). Agrochelin (638), ecteinascidin 743 (376), 729 (375), 597 (393), 583 (394), and 594 (395) have been reported to inhibit MEL-28 cells with IC50 values of 0.268 µM, 5.0, 5.0, 2.0, 5.0, and 25 ng/ml, respectively (Cañedo et al., 1999; Sakai et al., 1996).
1.5.9 Ovarian cancer
Ovarian cancer is a malignant tumor that grows on the ovary, with 90% to 95% of cases being primary ovarian cancers. Despite having a lower incidence rate than cervical and endometrial cancers, ovarian cancer has the highest mortality rate among gynecological cancers, ranking first. (Matulonis et al., 2016). 14-methyleudistomidin C (418) and aulosirazole A-B (623–624) demonstrated IC50 values of 0.98 μg/ml, 0.301, and 0.6 µM, respectively, against OVCAR-3 cells (Davis et al., 2022; Rashid et al., 2001). Additionally, brocazine G (963) exhibited inhibition of A2780 and A2780 CisR cells with IC50 values of 664 and 661 nM, respectively (Meng et al., 2016).
1.5.10 Others
In addition to their activity against the aforementioned tumour cells, sulphur-containing marine alkaloids have demonstrated promising cytotoxic properties against other types of cancer cells. For instance, luteoalbusin A (784), B (785), T988A (786), gliocladine C (787) and D (788) were reported to inhibit the growth of SF-268 and HepG-2 cells, with IC50 values ranging from 0.46 to 2.49 µM. Moreover, kuanoniamine C (82) and A (381) exhibited excellent cytotoxicity against SF-268 cells, with IC50 values of 33.16 and 4.67 nM, respectively. (Kijjoa et al., 2007). Of particular note, shishijimicin A (431), B (432), C (433) and namenamicin (434) displayed potent cytotoxicity against 3Y1 cells, with IC50 values of 2.0, 3.1, 4.8 and 13 pg/ml. (Oku et al., 2003).
1.5.11 Structure-activity relationships of the cytotoxicity
It is noteworthy that discorhabdins, curacins, tanjungides, leptosins, and latrunculins exhibit better cytotoxicity than any other reported compounds. Thus, the structure–activity relationships of the cytotoxicity of these compounds have been summarized for further investigation.
As depicted in Fig. 17a, the cytotoxicity of discorhabdins is decreased when there is a double bond between C-4 and C-5 of discorhabdins, which is also confirmed in Fig. 17b. When there is a hydroxyl substitution at C-3′, the cytotoxicity of the compound is increased. Fig. 17c reveals that the presence of substituents at C-2′ affects the cytotoxicity of the compound, and the degree of influence is related to the nature of the substituents, as confirmed in Fig. 17d. Simultaneously, Fig. 17c also shows that replacing the carbonyl group at C4′ with more hydroxyl groups does not affect the cytotoxicity, indicating that the presence of a carbonyl group does not affect cytotoxicity. Fig. 17d shows that the cytotoxicity of the compound is reduced when there is a double bond between C-5′ and C-6′, and converting the N atom at the C-6 position to NH+ also reduces the cytotoxicity. The cytotoxicity of latrunculins is strongly related to the configuration at C-18. When C-18 has an R-configuration, the cytotoxicity of the compounds increases, and when it has an S-configuration, the cytotoxicity decreases (Fig. 17e). When the hydroxyl group at C-17 is replaced by methoxy, the toxicity of the compound is also weakened. In addition, we found that as the lactone ring of these compounds becomes larger, their cytotoxicity increases, which may be related to the increase in the number of hydroxyl groups on the lactone ring.
The cytotoxicity of curacins and tanjungides is related to the configuration of the double bond in their structures. When the double bond is of the E-type, the cytotoxicity of the compounds increases, and when it is of the Z-type, it decreases. If there is a methyl group at C-9 of curacins, the cytotoxicity of the compound also increases (Fig. 17f). The cytotoxicity of leptosins is related to the number of sulfur atoms in the sulfur bridge. As the number of sulfur atoms increases, the cytotoxicity is attenuated, but if the sulfur bridge is missing, the cytotoxicity of leptosins is greatly reduced. It can be seen that the sulfur bridge is an important cytotoxic basis of leptosins. Cytotoxicity is reduced in the presence of methyl group at C-7, and increased in the presence of hydroxymethyl groups. Cytotoxicity is similarly reduced in the presence of hydroxyl groups in C-3. (Fig. 17g). In addition, the configuration of the hydroxyl groups at the C-3 and C-3′ positions will affect the cytotoxicity. The cytotoxicity will decrease when both are S-configurations, and it will increase when both are R-configurations. (Fig. 17h).
2 Conclusions and outlook
This review summarized current research regarding the chemical and bioactivity diversity of marine-derived sulphur-containing alkaloids from 1992 to 2022. More than 972 sulphur-containing alkaloids have been isolated and identified from the marine. Meanwhile, modern pharmacological research revealed that the sulphur-containing alkaloids have significant pharmacological properties including cytotoxicity, anti-proliferation, anti-virus, anti-inflammatory, antioxidant, antibacteria, antifungal, anti-malarial, antiparasitic and enzyme inhibitory activity. Regardless, there are still several aspects that need to be concerned in the further development of marine-derived sulphur-containing alkaloids.
Firstly, as shown in Fig. 1, sponges are the dominant producer of marine-derived sulphur-containing alkaloids, yielding 316 of these 972 compounds (32.51%). Marine animal tunicates also produce massive sulphur-containing alkaloids with a combined percentage of 16.26%. In addition, marine fungi and bacteria are also important sources, producing 20.27% and 11.32%, respectively, of the alkaloids reviewed. It can be seen that almost 80.36% of marine-derived sulphur-containing alkaloids are from marine sponges, fungi, tunicates and bacteria. This suggests that we can focus more on marine sponges, fungi, tunicates and bacteria in the search for more marine-derived sulphur-containing alkaloids.
Secondly, sulphur-containing alkaloids obtained from sponges have fallen since 2010, while microbes, especially fungi, have grown to be important producers (Fig. 2). There may be two reasons for this. (1) with the increasing demand for new bioactive substances, the attraction of terrestrial fungi in drug screening has gradually decreased. Scientists began to pay attention to marine fungi living in complex environments such as high pressure, high salt and low temperature. Meanwhile, the complex environment makes the secondary metabolites of marine fungi have diverse structures and unique biological activities, which attracts scientists to increase the research and development of marine fungi. (2) Biochemists have begun to generally acknowledge that sampling slow-growing sessile organisms to identify natural products is not an economical and environmentally friendly approach. Fungi can reproduce indefinitely under suitable conditions, and their genomes can be easily mined for targeted metabolites. This also makes fungi get more attention.
Thirdly, sulphur-containing alkaloids have been shown to have a variety of biological activities such as cytotoxicity, anti-proliferation, anti-virus, anti-inflammatory, antioxidant, antibacteria, antifungal, anti-malarial, antiparasitic and enzyme inhibitory activity. Of them, ecteinascidin 743 (yondelis) has been approved by the European Union in October 2007 for the treatment of advanced soft tissue tumors, which became the first modern marine drug (Menchaca et al., 2003). Thiomarinols, a kind of naturally occurring double-headed antibiotic, usually have excellent antibacterial activity and can even be effective against MRSA (Shiozawa et al., 1995). But more sulphur-containing alkaloids with various activities also need to be found in the marine. Of course, it can not be ignored that monomeric compounds with outstanding pharmacological activities can be considered the source of new drugs with excellent therapeutic effects. For example, shishijimicin A (431), B (432), C (433) and namenamicin (434) exhibited extremely cytotoxic to 3Y1, HeLa and P388 cells with IC50 values from 0.47 to 43 pg/ml. Gliotoxin (792), acetylgliotoxin (804) and reduced gliotoxin (803) have been reported to inhibit HCT-116 and RKO cells with IC50 values from 0.41 to 4.49 µM. Chetracin E (875), F (876) and C (877) also have cytotoxicity against A549, HCT116, K562, H1975 cells with GI50 from 0.2 to 3.6 μM.
Fourth, although many compounds with excellent activity have been found in sulphur-containing alkaloids, only a few components have been fully and deeply studied, and a large number of active components have only been tested for simple biological activity. This may be related to active compounds being too few to support a more in-depth study of the mechanism. Such problems usually need to be solved by chemical synthesis, but it is not realistic to synthesize each compound without purpose. At present, it is proposed to simulate the combination of active components and target receptors by molecular docking technology to achieve preliminary screening of active compounds, which may be a method to reduce the workload (Chen et al., 2020). All in all, it is still necessary to further study the mechanism of active sulphur-containing alkaloids to provide a scientific basis for the development of new drugs.
Fifth, the remarkable chemical diversity and biological activities of marine-derived sulphur-containing alkaloids make them attractive candidates for drug discovery and development. With the continued development of advanced techniques for marine natural product isolation, structure elucidation, and biosynthesis studies, we can expect to discover even more diverse and potent sulphur-containing alkaloids.The future impact of marine-derived sulphur-containing alkaloids in the drug discovery avenue will be more significant too.
Finally, the ocean is a huge treasure house of medicine awaiting human exploration. Among the natural marine products, sulphur-containing alkaloids are important potential drugs that deserve further research and development. This review could be a useful tool in assisting researchers in the selection of interesting species or isolated compounds for further studies, as well as expand the research of marine-derived sulphur-containing alkaloids.
Author contributions
Z.L. Zhang, Y.Z. Li, W. Wang and Y. Sun searched and collected literature; Z.L. Zhang and Y.Z. Li carried out the writing work; X.M. Song and D.D. Zhang designed this review. All authors have read and agreed to the published version of the manuscript.
Acknowledgements
We thank the foundations of the National Natural Science Foundation of China (82104368) and Shaanxi Provincial Science and Technology Department Project (2021JQ-744) for financial support of this study.
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Appendix A
Supplementary material
Supplementary data to this article can be found online at https://doi.org/10.1016/j.arabjc.2023.105011.
Appendix A
Supplementary material
The following are the Supplementary data to this article:Supplementary data 1
Supplementary data 1