Chemical diversity and biological activities of marine-derived sulphur containing alkaloids: A comprehensive update

Zilong Zhang; Yuze Li; Yu Sun; Wei Wang; Xiaomei Song; Dongdong Zhang

doi:10.1016/j.arabjc.2023.105011

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Review article

09 2023

:16;

105011

doi:

10.1016/j.arabjc.2023.105011

Chemical diversity and biological activities of marine-derived sulphur containing alkaloids: A comprehensive update

Zilong Zhang^{^a}, Yuze Li^{^a}, Yu Sun^{^b}, Wei Wang^{^a}, Xiaomei Song^{^a}, Dongdong Zhang^{^a,⁎}

a School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi 712046, PR China

b The Second Affiliated Hospital of Shaanxi University of Chinese Medicine, Xianyang, Shaanxi 712000, PR China

⁎Corresponding author at: School of Pharmacy, Shaanxi University of Chinese Medicine, Xianyang, Shaanxi Provance of China 712046. zhangnatprod@163.com (Dongdong Zhang)

Received: 2022-12-30, Accepted: 2023-5-14,

Disclaimer:
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

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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).

The percentage of sulphur-containing alkaloids from diverse marine organisms.

All sulphur-containing alkaloids by source/year, n = 972.

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

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

1.2 Chemical diversity of Marine-Derived Sulphur-containing alkaloids

1.2.1

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).

Table 1 Sulphur-containing alkaloids from marine algae.

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

1.2.2 Marine fauna

1.2.2.1

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.

Table 2 Sulphur-containing alkaloids from marine sponges.

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			(Spector et al., 1983)
18	latrunculin C	1985			(Kashman et al., 1985)
19	latrunculin D	1985			(Kashman et al., 1985)
20	agelasidine B	1984	Agefas nakamurai	Okinawa, Japan	(Nakamura et al., 1985)
21	agelasidine C	1984	Agefas nakamurai		(Nakamura et al., 1985)
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	Guam, U.S.A.	(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	Latrunculia sp.	New Zealand	(Perry et al., 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	Latruncularia magnifica	Red Sea	(Blasberger et al., 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	Batzella sp.		(Sakemi et al., 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	Dysidea avara	Solomon Islands	(Alvi et al., 1992)
59	(−)-agelasidine C	1992	Agelas clathrodes	Puerto Rico	(Morales and Rodríguez, 1992)
60	(−)-agelasidine D	1992	Agelas clathrodes	Puerto Rico	(Morales and Rodríguez, 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	Hymeniacidon sp.	Okinawa, Japan	(Kobayashi et al., 1997)
80	thiomycalolide A	1998	Mycale sp.	Japan	(Matsunaga et al., 1998)
81	thiomycalolide B	1998	Mycale sp.	Japan	(Matsunaga et al., 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	Penares sp.	Japan	(Nakao et al., 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)
96	discorhabdin R	2000	Negombata sp.	Victoria, Port Campbell	(Ford and Capon, 2000)
97	ianthesine C	2000	Ianthella sp.	Australian	(Okamoto et al., 2000)
98	ianthesine D	2000	Ianthella sp.	Australian	(Okamoto et al., 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	Aplysinella rhax	Great Barrier Reef	(Pham et al., 2000)
105	wondonin A	2001	Poecillastra wondoensisand Japsis sp.	Keomun Island, Korea	(Shin et al., 2001)
106	wondonin B	2001	Poecillastra wondoensisand Japsis sp.	Keomun Island, Korea	(Shin et al., 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	Aplysinella rhax	Fijian	(Tabudravu et al., 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	(Sakai et al., 2003)
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	Dragmacidon sp.	Adaman Islands, India	(Pedpradab et al., 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	Latrunculia brevis	Tierra del Fuego, Patagonia, Argentina	(Reyes et al., 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	Latrunculia sp.	New Zealand	(Lang et al., 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	Latruncularia magnifica	Red Sea
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			(Kubota et al., 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	Latrunculia wellingtonesis	Wellington, New Zealand	(Grkovic and Copp, 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	Latrunculia fiordensi
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	Suberites sp.	Unten Port, Okinawa, Japan	(Takahashi et al., 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	Agelas citrina	Bahamas	(Stout et al., 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	Hyrtios sp.	Kerama island, Okinawa, Japan	(Tanaka et al., 2013c)
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			(Tanaka et al., 2013a)
250	nagelamide Y	2013			(Tanaka et al., 2013b)
251	nagelamide Z	2013			(Tanaka et al., 2013b)
252	reticulatin A	2013	Hyrtios reticulatus	N. Sulawesi, Indonesia	(Imada et al., 2013)
253	reticulatin B	2013	Hyrtios reticulatus	N. Sulawesi, Indonesia	(Imada et al., 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	Coscinoderma mathewsi	Vangunu Island,Solomon Islands	(De Marino et al., 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	Callyspongia sp.	Great Australian Bight	(Plisson et al., 2014)
273	tauroacidin C	2014	Agelas sp.	Kerama islands,Okinawa, Japan	(Kusama et al., 2014)
274	tauroacidin D	2014	Agelas sp.	Kerama islands,Okinawa, Japan	(Kusama et al., 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	Agelas sp.	Kerama island, Okinawa, Japan	(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	Poecillastra wondoensis	Keomun Island, Korea	(Chang et al., 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		Dredge,Southern Weddell Sea, Antarctica	(Li et al., 2020c)
319	psammaplin O	2020	Aplysinella rhax	Wainunu, Bua, Fiji island	(Oluwabusola et al., 2020)
320	psammaplin P	2020	Aplysinella rhax	Wainunu, Bua, Fiji island	(Oluwabusola et al., 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	Tedaniophorbas ceratosis	northern New South Wales, Australia.	(Hiranrat et al., 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

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).

Table 3 Sulphur-containing alkaloids from marine cnidarians.

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	Sinularia sp.	Manado, North Sulawesi, Indonesia	(Putra et al., 2012)
342	palyosulfonoceramide A	2012	Palythoa caribaeorum andProtopalythoa variabilis	Paracuru beach,Fortaleza, Brazil	(Almeida et al., 2012)
343	palyosulfonoceramide B	2012	Palythoa caribaeorum andProtopalythoa variabilis	Paracuru beach,Fortaleza, Brazil	(Almeida et al., 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	Melitodes squamata	Sanya, Hainan,South China Sea	(Huang et al., 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

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).

Table 4 Sulphur-containing alkaloids from marine tunicates.

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	Aplydium pliciferum	Australian	(Arabshahi and Schmitz, 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	Lissoclinum vareau	Yasawa island chain, Fiji	(Molinski and Ireland, 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	Eudistoma glaucus	Ie Island, Okinawan,Japan	(Kobayashi et al., 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	Eudistoma glaucus	Ie Island, Okinawan,Japan	(Murata et al., 1991)
381	kuanoniamine A	1990	an unidentified Micronesian tunicate	Mante Channel, Pohnpei,Micronesia	(Carroll and Scheuer, 1990)
382	kuanoniamine B	1990	an unidentified Micronesian tunicate	Mante Channel, Pohnpei,Micronesia	(Carroll and Scheuer, 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	Cystodytes sp.	Fiji	(McDonald et al., 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	Polycarpa clavataPolycarpa aurata	Western AustraliaChuuk, Federated States of Micronesia	(Kang and Fenical, 1996),(Abas et al., 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	Polycarpa aurata	Chuuk, Federated States of Micronesia	(Abas et al., 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	an unidentified Singaporean ascidian	Pulau Subar Laut,Singapore	(Nilar et al., 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	Aplidium conicum	Capo Caccia, Alghero, Italy	(Aiello et al., 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	Atriolum robustum	Heron Islands, Wistari Reef, Great Barrier Reef	(Kehraus et al., 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	Aplidium sp.	Tom Bowling Bay,Northland, New Zealand	(Pearce et al., 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	Cystodytes dellechiajei	Catalonia, Spain	(Bontemps et al., 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	Polycarpa aurata	Ambon, Indonesia	(Pham et al., 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	Aplidium conicum	Porto Cesareo, Lecce, Italy	(Menna et al., 2013)
470	shermilamine F	2013	Cystodytes violatinctus	Solomon islands	(Bontemps et al., 2013)
471	dehydrokuanoniamine F	2013	Cystodytes violatinctus	Solomon islands	(Bontemps et al., 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	Diazona cf formosa	East Timor	(Murcia et al., 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

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).

Table 5 Sulphur-containing alkaloids from marine echinoderms.

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(N^α.N^α,l-trimethyI-L-histidin-5-yl)disulphide	1986	unfertilized echinoderm eggs	–	(Faulkner, 1986)
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	–	(Turner et al., 1987)
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	Ophiocoma scolopendrina	Kabira Reef, Ishigaki island, Okinawa, Japan	(Ueoka et al., 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

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).

Table 6 Sulphur-containing alkaloids from marine molluscs.

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	Eudistoma cf. rigida	Okinawa, Japan	(Kikuchi et al., 1991)
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	Wild mussels (Mytilus edulis andMytilus trossulus)	Eastern Canada coasts	(Dell’Aversano et al., 2008)
543	orbicularisine	2017	Codakia orbicularis	Guadeloupe	(Goudou et al., 2017)

1.2.2.6

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).

Table 7 Sulphur-containing alkaloids from marine bryozoans.

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

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).

Table 8 Sulphur-containing alkaloids from other marine animals.

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

1.3 Marine microorganism

1.3.1

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).

Table 9 Sulphur-containing alkaloids from dinoflagellates.

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	Symbiodinium sp.	Sesoko Island, Okinawa, Japan.	(Kita et al., 2005)
588	ovataline	2022	Ostreopsis cf. ovata	Kimyong, Jeju island	(Lee et al., 2022)

1.3.2

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).

Table 10 Sulphur-containing alkaloids from cyanobacteria.

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			(Yoo and Gerwick, 1995)
593	barbamide	1996			(Orjala and Gerwick, 1996)
519.	curacin A 519	1998		Virgin Islands, British	(Márquez et al., 1998)
594	curacin D	1998		Virgin Islands, British	(Márquez et al., 1998)
595	kalkitoxin	2000		Curaçao, Caribbean sea	(Yokokawa et al., 2004)
596	dechlorobarbamide	2000		Curaçao, Caribbean sea	(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	Okeania sp.	Algetah Alkabira reef, Jeddah, Saudi Arabia	(Petitbois et al., 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	Trichodesmium sp.	Mayaguana Island, Bahamas	(Teta et al., 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

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.

Table 11 Sulphur-containing alkaloids from marine bacteria.

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			(Shiozawa et al., 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	Bacillus vallismortis	Sanya island, South China Sea	(Yu et al., 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	Erythrobacter sp.	Trinity Bay, Galveston, Texas, U.S.A.	(Hu and MacMillan, 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	Streptomyces nitrosporeus	Arctic Chukchi Sea	(Yang et al., 2013)
669	tetroazolemycin A	2013	Streptomyces olivaceus	southwest Indian Ocean	(Liu et al., 2013)
670	tetroazolemycin B	2013	Streptomyces olivaceus	southwest Indian Ocean	(Liu et al., 2013)
671	forazoline A	2014	Actinomadura sp. WMMB-499	Florida, U.S.A.	(Wyche et al., 2014)
672	forazoline B	2014	Actinomadura sp. WMMB-499	Florida, U.S.A.	(Wyche et al., 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	Streptomyces sp.	Jimei, China	(Deng et al., 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	Streptomyces spinoverrucosus	Bahamas	(Fu and MacMillan, 2015a)
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	Brevibacillus sp.	Ohtsuchi, Iwate, Japan	(Igarashi et al., 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	Salinispora pacifica	Fiji	(Harig et al., 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	Saccharomonospora sp.	La Jolla Submarine Canyon, California	(Le et al., 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	Streptomyces cyaneofuscatus M−157	Avilés Canyon, Cantabrian Sea	(Ortiz-López et al., 2018)
714	thymidine-3-mercaptocarbamic acid	2019	Streptomyces sp.	Red Sea	(Shaala et al., 2019)
715	thymidine-3-thioamine	2019	Streptomyces sp.		(Shaala et al., 2019)
716	nocarterphenyl A	2019	Nocardiopsis sp. OUCMDZ-4936	Dongzhaigang Mangrove Reserve, China	(Wang et al., 2019)
717	nocarterphenyl B	2019	Nocardiopsis sp. OUCMDZ-4936	Dongzhaigang Mangrove Reserve, China	(Wang et al., 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	Alteromonas sp. D	Hiroshima-bay, Hiroshima, Japan	(Umetsu et al., 2019)
722	mindapyrrole B	2019	Pseudomonas aeruginosa	Sultan Kudarat, Mindanao, Philippines	(Lacerna et al., 2019)
723	mindapyrrole C	2019	Pseudomonas aeruginosa	Sultan Kudarat, Mindanao, Philippines	(Lacerna et al., 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

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.

Table 12 Sulphur-containing alkaloids from marine 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	Penicillium sp. CNC-350	–	(John, 1999)
753	flavochristamide A	2000	Flavobacterium sp.	lshikari Bay, Hokkaido	(Kohayashi et al., 1995)
754	flavochristamide B	2000	Flavobacterium sp.	lshikari Bay, Hokkaido	(Kohayashi et al., 1995)
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			(Blunt et al., 2004)
761	Sch 54,794	1993			(Chu et al., 1993)
762	Sch 54,796	1993			(Chu et al., 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	Alternaria raphani	Qingdao, China	(Wang et al., 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	Penicillium sp.	Suruga Bay, Japan	(Sun et al., 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	Stachybotrys chartarum	Beibuwan Bay, China	(Li et al., 2014)
809	cladosporin A	2015	Cladosporium sp.	Yangshashan Bay, Ningbo, Zhejiang, China	(Gu et al., 2015)
810	cladosporin B	2015	Cladosporium sp.	Yangshashan Bay, Ningbo, Zhejiang, China	(Gu et al., 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	Penicillium adametzioides	Hainan island, China	(Liu et al., 2015b)
826	peniciadametizine A	2015	Penicillium adametzioides	Wenchang, Hainan, China	(Liu et al., 2015c)
827	peniciadametizine B	2015	Penicillium adametzioides	Wenchang, Hainan, China	(Liu et al., 2015c)
828	pseudellone A	2015	Pseudallescheria ellipsoidea F42 − 3	National Coral Reef Reserve, Hainan, China	(Liu et al., 2015a)
829	pseudellone B	2015	Pseudallescheria ellipsoidea F42 − 3	National Coral Reef Reserve, Hainan, China	(Liu et al., 2015a)
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	Pseudallescheria boydii		(Lan et al., 2016)
843	lasiodipline F	2016	Pseudallescheria ellipsoidea F42-3		(Wang et al., 2016)
844	pseudellone D	2016	Pseudallescheria ellipsoidea F42-3		(Wang et al., 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			(Cao et al., 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			(Wu et al., 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			(Chi et al., 2020b)
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	Trichoderma cf. brevicompactum	Palau	(Yamazaki et al., 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

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).

Sulphur-containing alkaloids from mangroves bacteria, fungi, other marine microorganism.

Table 13 Sulphur-containing alkaloids from mangroves bacteria, fungi and other marine microorganism.

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	Trichoderma harzianum D13		(Zhao et al., 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

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

1.5 Cytotoxicity

1.5.1

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

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

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

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

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

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

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

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

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

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

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.

Structure-activity relationships of the cytotoxicity.

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:

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Introduction

Search strategy
Chemical diversity of Marine-Derived Sulphur-containing alkaloids
Marine microorganism
Bioactivities of Marine-Derived Sulphur-containing alkaloids
Cytotoxicity

Conclusions and outlook

Author contributions

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Chemical diversity and biological activities of marine-derived sulphur containing alkaloids: A comprehensive update

Abstract

Objectives

Key findings

Summary

Keywords

Sulphur-containing alkaloids

Marine organisms

Chemical diversity

Bioactivity diversity

Cytotoxicity

1 Introduction

1.1 Search strategy

1.2 Chemical diversity of Marine-Derived Sulphur-containing alkaloids

1.2.1 Marine algae

1.2.2 Marine fauna

1.2.2.1 Marine sponges

1.2.2.2 Marine cnidarians

1.2.2.3 Marine tunicates

1.2.2.4 Marine echinoderms

1.2.2.5 Marine molluscs

1.2.2.6 Marine bryozoans

1.2.2.7 Other marine animals

1.3 Marine microorganism

1.3.1 Dinoflagellates

1.3.2 Cyanobacteria

1.3.3 Marine bacteria

1.3.4 Marine fungi

1.3.5 Mangroves bacteria, fungi and other marine microorganism

1.4 Bioactivities of Marine-Derived Sulphur-containing alkaloids

1.5 Cytotoxicity

1.5.1 Leukemia

1.5.2 Lymphomas

1.5.3 Colorectal cancer

1.5.4 Pancreatic cancer

1.5.5 Breast cancer

1.5.6 Lung cancer

1.5.7 Cervical cancer

1.5.8 Melanoma

1.5.9 Ovarian cancer

1.5.10 Others

1.5.11 Structure-activity relationships of the cytotoxicity

2 Conclusions and outlook

Author contributions

Acknowledgements

References

Appendix A

Supplementary material

Appendix A

Supplementary material

Supplementary data 1

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