Genus Chloranthus: A comprehensive review of its phytochemistry, pharmacology, and uses
⁎Corresponding author at: School of Pharmacy, Shaanxi University of Chinese Medicine, No.1, Middle Section of Century Avenue, Qindu District, Xianyang, Shaanxi Province 712046, PR China (D.D. Zhang). School of Pharmacy, Shaanxi University of Chinese Medicine, No.1, Middle Section of Century Avenue, Qindu District, Xianyang, Shaanxi Province 712046, PR China (W. Wang). zhangnatprod@163.com (Dong-dong Zhang), 2051003@sntcm.edu.cn (Wei Wang)
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This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Abstract
This paper is intended to review advances in the botanical, traditional uses, phytochemical, pharmacological and development and utilization studies of the genus Chloranthus. Chloranthus, a genus of the family Chloranthaceae, which is mainly distributed in the temperate and tropical regions of Asia, has been used as a folk remedy for swollen boils, snake bites and bruises. Up to now, 418 compounds have been reported from the genus Chloranthus, including 383 terpenoids, 4 coumarins, 6 lignans, 2 simple phenylpropanoids, 4 flavonoids, 6 amides, 5 organic acids and some other types of compounds. Among them, the main chemical constituents are sesquiterpenes and their diterpenoids. Modern pharmacological studies have shown that most of the Chloranthus plants possessed anti-cancer, anti-inflammatory, antibacterial, antiviral, and antimalarial activities. As one of the most important genera in China, Chloranthus should be paid further attention to gathering information about the pharmacological mechanism and value active compounds. This paper summarized the phytochemistry, pharmacology, and uses of genus Chloranthus in order to lay a foundation and provide reference for the follow-up research and wide application of the genus.
Keywords
Chloranthus
Traditional uses
Chemical constituents
Pharmacological
Development and utilization
Review
1 Introduction
The genus Chloranthus belongs to the family Chloranthaceae, and consists of 14 species in the world (Chloranthus Swartz in Flora of China @ efloras.org“ eFlora). They are mainly distributed in temperate and tropical Asia (Lu et al., 2020). Among them, 13 species are reported in southwestern, southern, eastern and central China (Chloranthus Swartz in Flora of China @ efloras.org eFlora). As the country with the abundant resources of the genus Chloranthus, China has a long history of application of the genus Chloranthus plants. In traditional Chinese medicine (TCM) theory, their effects are defined as dispersing cold, dispelling wind and relieving pain, removing blood stasis and detoxifying (Zhang, 2016). According to the Dictionary of Traditional Chinese Medicine, Fujian Folk Herbal Medicine, Jiangxi Herbal Medicine and other local herbal standards, most of this genus plants can be used as folk herbal medicine to treat wind-cold cough, bruises and injuries, rheumatism and lumbago.
Due to the novelty of the chemical structure and the richness of biological activities, a large number of scholars at home and abroad have conducted in-depth studies on genus Chloranthus. Modern pharmacology has shown that this genus has excellent pharmacological activities in anticancer, antibacterial, anti-inflammatory and neuroprotective effect (Chen et al., 2021c; Huang et al., 2020). Phytochemical studies discovered the presence of sesquiterpenes, coumarins, lignans, simple phenylpropanoids, flavonoids and amides from this genus. Especially sesquiterpenes dimer macrocyclic compounds possess significant antitumor activity. Such as the types of chloranthalactone and shizukanolide, studies have shown that this class of compounds showed significant activity against A549 cells, human glioma U87 cells, and hepatocellular carcinoma SMMC-7721 cells (Zhang et al., 2021). It has a broad prospect in developing drugs against breast cancer and liver cancer. Eudesmane sesquiterpenes isolated from the C. fortunei, such as fortunilide A (96), sarglabolide J (100), chlorahololide D (103), most of which exhibited antimalarial activity, which was comparable to the potency and selectivity index values of artemisinin (Zhou et al., 2017a).
This review summarized the research advancement of this genus in botanical, traditional uses, phytochemical, pharmacological and development and utilization studies at the past 30 years, in order to provide reference for further applications and research of the genus Chloranthus.
2 Search strategy
Comprehensive research and analysis of previously published literature were conducted for studies on the traditional use, distribution, chemistry, and pharmacological properties of the genus Chloranthus. The search was conducted using databases such as Sciencedirect, SciFinder, Medline PubMed, Google Scholar, Baidu Scholar, and CNKI by using the keywords such as Chloranthus, Chloranthus. japonicus, Chloranthus. henryi and Chloranthus multistachys. Part of the analyzed studies was got by a manual search of articles in the reference lists of the included studies. The chemical structures were drawn using ChemDraw Professional 20.0 software.
3 Botany, description and distribution
To date, about 13 species of the genus Chloranthus have been reported in China, inculding Chloranthus elatior Link, Chloranthus spicatus (Thunb.) Makino, Chloranthus angustifolius Oliv, Chloranthus japonicus Sieb, Chloranthus fortunei (A. Gray) Solms-Laub, Chloranthus holostegius (Hand.-Mazz.) Pei et Shan, Chloranthus anhuiensis K. F. Wu, Chloranthus tianmushanensis K. F. Wu, Chloranthus serratus (Thunb.) Roem. et Schult, Chloranthus multistachys Pei, Chloranthus henryi Hemsl, Chloranthus sessilifolius K. F. Wu and Chloranthus oldhamii Solms Laubach. Among them, about eight species of the genus are available for medicinal use in China. Among which C. japonicus, C. serratus, C. multistachys and C. henryi are extensively studied (Chloranthus in Flora of China @ efloras.org, 2020). Most of the plants in the genus commonly grow on mountain slopes in the forest understory and gully side grasses. They are subshrubs or perennial herbs. Leaves opposite or whorled, serrate; stipules tiny; petioles connected by a transverse ridge on stem. Inflorescences in spikes or branched, arranged in panicles, terminal or axillary. Flowers small, bisexual; perianth absent. Stamens usually 3, rarely 1, on 1 side of apical part of ovary; basal part of connective confluent, or free and connected or overlapped at base, ovoid or lanceolate, sometimes elongated to linear; anthers 1-or 2-loculed; if stamens 3, central anther 2-loculed or occasionally absent, lateral anthers 1-loculed, if stamen 1, anther 2-loculed. Ovary 1-loculed; ovule 1, pendulous, orthotropous; style usually absent, rarely present; stigma truncate or parted. Drupes globose, obovoid, or pyriform (Chloranthus in Flora of China @ efloras.org, 2020).
4 Traditional uses
Most of plants in the genus Chloranthus are used as folk herbal medicine and have a long history of medicinal use. It has the medicinal potencies of dispelling wind and cold, strengthening bones and tendons, activating blood circulation and dispersing blood stasis, removing swelling and relieving pain, and are commonly used to treat bruises, swelling and pain, rheumatic arthritis, boils, sores and swellings in the folk. Moreover, the resources of this genus are rich in species and reserves, and have a high value for development and utilization. In this paper, we have collected proprietary Chinese patent medicines or preparations on the genus Chloranthus, which include empirical prescriptions for folk use, in-hospital preparations and marketed drugs. (Table 3).
5 Phytochemistry and Pharmacology
Literature investigation revealed that Chloranthus include terpenoids, coumarins, amides and phenylpropanoids, among which sesquiterpenoids and diterpenoids are predominant structural types and active components. Up to now, 418 compounds have been reported from the genus Chloranthus, including 383 terpenoids, 4 coumarins, 6 lignans, 2 simple phenylpropanoids, 4 flavonoids, 5 organic acids, 6 amides, and 8 other compounds. Their specific compound names, structures and references are shown in Table 1 and Figs. 1–19.
No. | Name | Plant | Bioactivity | Part | References |
---|---|---|---|---|---|
Lindenane Sesquiterpenes and Their Polymers | |||||
1 | shizukanolide | E | Antitumor activity | Aerial | (Kawabata et al., 1981) |
2 | chloranthalactone A | E | Antitumor activity | Aerial | (Uchida et al., 1980) (Gong et al., 2021) |
3 | yinxiancaoside A | E | Antitumor activity | Whole | (Kuang et al., 2008) |
4 | chloranoside A | E | Whole | (Kuang et al., 2008) | |
5 | chloranthalactone B | E | Antitumor activity | Whole | (Uchida et al., 1980) (Gong et al., 2021) |
6 | chloranthalactone C | EF | Whole | (Uchida et al., 1980) | |
7 | chloranthalactone D | E | Whole | (Uchida et al., 1980) | |
8 | chloranthalactone E | E | Whole | (Uchida et al., 1980) | |
9 | 9-hydroxy heterogorgiolide | E | Aerial | (Uchida et al., 1980) | |
10 | chlojaponilactone B | E | Whole | (Yan et al., 2013) | |
11 | chlojaponilactone C | E | Whole | (Yan et al., 2013) | |
12 | chlojaponilactone D | E | Whole | (Yan et al., 2013) | |
13 | chlorajapolide C | E | Whole | (Yan et al., 2013) | |
14 | chlojaponilactones E | E | Whole | (Yan et al., 2013) | |
15 | chlorajapolides F | E | Aerial | (Zhang et al., 2012a) | |
16 | chlorajapolides G | E | Aerial | (Zhang et al., 2012a) | |
17 | chlorajapolides H | E | Aerial | (Zhang et al., 2012a) | |
18 | chlojaponilactones F | E | Whole | (Li et al., 2016) | |
19 | chlojaponilactones H | E | Whole | (Li et al., 2016) | |
20 | chlojaponilactones G | E | Whole | (Li et al., 2016) | |
21 | chlojaponilactones I | E | Whole | (Li et al., 2016) | |
22 | chlorajapolides A | E | Antitumor activity | Whole | (Wang et al., 2011) |
23 | chlorajapolides B | E | Antitumor activity | Whole | (Wang et al., 2011) |
24 | chlorajapolides C | E | Antitumor activity | Whole | (Wang et al., 2011) |
25 | chlorajapolides D | E | Antitumor activity | Whole | (Wang et al., 2011) |
26 | chlorajapolides E | E | Antitumor activity | Whole | (Wang et al., 2011) |
27 | chlorajaposide | E | Whole | (Wang et al., 2011) | |
28 | chloranthalactone A | E | Roots | (Uchida et al., 1980) | |
29 | shizukanolide C | F | Aerial | (Fang, 2011) | |
30 | shizukanolide H | EFH | Neuroprotective activity | Whole | (Fang, 2011) |
31 | shizukanolide G | F | Anti-inflammatory activity | Aerial | (Wang et al., 2009) (Gong et al., 2021) |
32 | shizukanolide F | F | Aerial | (Wang et al., 2009) | |
33 | lindenanolide H | G | Whole | (Kim et al., 2011) | |
34 | (1R,3S,5S,8S,10R)-14-Acetylshizukanolide | H | Whole | (Xu et al., 2018) | |
35 | isoshizukanolide | F | Whole | (Zhou et al., 2017b) | |
36 | spicachlorantins G | C | Antiinflammatory activity | Roots | (Kim et al., 2011) |
37 | spicachlorantins H | C | Roots | (Kim et al., 2011) | |
38 | spicachlorantins I | C | Roots | (Kim et al., 2011) | |
39 | spicachlorantins A | C | Roots | (Kim et al., 2011) | |
40 | spicachlorantins B | C | Antiinflammatory activity | Roots | (Kim et al., 2011) |
41 | spicachlorantins C | C | Roots | (Kim et al., 2011) | |
42 | spicachlorantins D | C | Roots | (Kim et al., 2011) | |
43 | chloramultilide A | CDF | Antineuroinflammatory activity Antimicrobial activity |
Roots | (Kim et al., 2011) (Yang et al., 2014) |
44 | spicachlorantins E | C | Roots | (Kim et al., 2011) | |
45 | spicachlorantins F | C | Roots | (Kim et al., 2011) | |
46 | chloramultilide B | C | Antimicrobial activity | Whole | (Xu et al., 2007) |
47 | chloramultilide C | C | Antimicrobial activity | Whole | (Xu et al., 2007) |
48 | chloramultilide D | C | Whole | (Xu et al., 2007) | |
49 | trichloranoids A | C | Antimalarial activity | Whole | (Zhou et al., 2021) |
50 | trichloranoids B | C | Whole | (Zhou et al., 2021) | |
51 | trichloranoids C | C | Whole | (Zhou et al., 2021) | |
52 | trichloranoids D | C | Antimalarial activity | Whole | (Zhou et al., 2021) |
53 | analogue | C | Antimalarial activity | Whole | (Zhou et al., 2021) |
54 | chlojapolides A | DE | Antiinflammatory activity | Whole | (Guo et al., 2016) |
55 | chlojapolides B | DE | Whole | (Guo et al., 2016) | |
56 | chlojapolides C | DE | Whole | (Guo et al., 2016) | |
57 | chlojapolides D | DE | Whole | (Guo et al., 2016) | |
58 | chlojapolides E | DE | Whole | (Guo et al., 2016) | |
59 | chlojapolides F | DE | Whole | (Guo et al., 2016) | |
60 | shizukaol A | DEF | Antiinflammatory activity | Whole | (Guo et al., 2016) (Gong et al., 2021) |
61 | shizukaol A acetate | E | Roots | (Kawabata et al., 1990) | |
62 | chlojapolides G | DE | Aerial | (Guo et al., 2016) | |
63 | chlojapolides H | DE | Aerial | (Guo et al., 2016) | |
64 | spicachlorantin H | DE | Aerial | (Guo et al., 2016) | |
65 | shizukaol B | CDEFJ | Antitumor activity Antinflammatory activity Anti-viral Activity |
Whole | (Zhang et al., 2012a) (Fang et al., 2011) |
66 | shizukaol F | DEFGJ | Antitumor activity HIV-1 RNase H inhibitor Anti-viral Activity |
Whole | (Guo et al., 2016) (Xu, 2016) (Fang et al., 2011) |
67 | shizukaol G | DEF | Anti-inflammatory Anti-tumor activity |
Aerial | (Guo et al., 2016) |
68 | shizukaol C | CDEFG | Anti-inflammatory activity Insecticidal activity Anti-tumor activity Anti-viral Activity |
Aerial | (Zhang et al., 2012a) (Guo et al., 2016) (Gong et al., 2021) (Shi et al., 2015) (Fang, 2011) |
69 | shizukaol D | DEFJ | Anti-inflammatory activity Anti-tumor activity Hypoglycemic Activity |
Aerial | (Guo et al., 2016) (Shi et al., 2015) (Zhang et al., 2012) (Hu et al., 2017) |
70 | shizukaol H | CE | Anti-viral Activity | Aerial | (Fang, 2011) (Fang et al., 2011) |
71 | chloramultilide B | DEF GJ | Anti-bacterial activity | Aerial | (Fang, 2011) |
72 | spicachlorantin B | DEF | Anti-neuroinflammatory activity | Aerial | (Zhou et al., 2017b) |
73 | chlorahololide C | DEF | Inhibiting K+ channels | Aerial | (Guo et al., 2016) (Yang et al., 2008) |
74 | spicachlorantins J | C | Roots | (Guo et al., 2016) | |
75 | henriol A | D | Antimicrobial activity | Aerial | (Xu, 2016) (Yang et al., 2014) |
76 | spicachlorantin A | DJ | Antimicrobial activity | Roots | (Yang et al., 2014) |
77 | tianmushanol | DJI | Inhibiting TYR activity Antimicrobial activity |
Roots | (Yang et al., 2014) |
78 | 8-O-methyltianmushanol | DIJ | Inhibiting TYR activity Antimicrobial activity |
Roots | (Yang et al., 2014) (Wu et al., 2008) |
79 | chlojapolactone A | E | Anti-inflamma tory activity | Whole | (Guo et al., 2015) |
80 | multistalide C | E | Insecticidal activity | Whole | (Shi et al., 2015) |
81 | chlorajaponilide I. | E | Whole | (Zhuo et al., 2017) | |
82 | spicachlorantin D | EF | Whole | (Zhuo et al., 2017) | |
83 | chlorajaponilide C | EF | Antimalarial activity | Whole | (Zhuo et al., 2017) (Zhou et al., 2017b) |
84 | japonicones A | E | Whole | (Yan et al., 2019) | |
85 | japonicones B | E | Whole | (Yan et al., 2019) | |
86 | japonicones C | E | Whole | (Yan et al., 2019) | |
87 | chlorajaponol | E | Whole | (Wang et al., 2011) | |
88 | chloranthadimeric acid acetate | E | Roots | (Uchida et al., 1980) | |
89 | chlorajaponilides A | E | Whole | (Fang, 2011) | |
90 | chlorajaponilides B | E | Whole | (Fang, 2011) | |
91 | chlorajaponilides D | E | Whole | (Fang, 2011) | |
92 | chlorajaponilides E | E | Whole | (Fang, 2011) | |
93 | cloramultilide C | E | Whole | (Fang, 2011) | |
94 | yinxiancaol | EFG | Whole | (Fang, 2011) | |
95 | chlorafortulide | F | Whole | (Zhang et al., 2012a) | |
96 | fortunilide A | F | Antimalarial activity | Whole | (Zhou et al., 2017b) |
97 | fortunilide B | F | Whole | (Zhou et al., 2017b) | |
98 | fortunilide C | F | Whole | (Zhou et al., 2017b) | |
99 | sarglabolide I | F | Whole | (Zhou et al., 2017b) | |
100 | sarglabolide J | F | Antimalarial activity | Whole | (Zhou et al., 2017b) |
101 | shizukaol K | F | Whole | (Zhou et al., 2017b) | |
102 | shizukaol M | F | Whole | (Zhou et al., 2017b) | |
103 | chlorahololide D | FGJ | Inhibiting K+ channels | Whole | (Zhou et al., 2017b) (Yang et al., 2008) |
104 | shizukaol N | F | Whole | (Zhou et al., 2017b) | |
105 | sarcandrolide B | F | Whole | (Zhou et al., 2017b) | |
106 | sarcandrolide A | F | Whole | (Zhou et al., 2017b) | |
107 | sarcandrolide J | F | Whole | (Zhou et al., 2017b) | |
108 | sarcandrolide E | F | Whole | (Zhou et al., 2017b) | |
109 | fortunilides D | F | Whole | (Zhou et al., 2017b) | |
110 | fortunilides E | F | Whole | (Zhou et al., 2017b) | |
111 | fortunilides F | F | Whole | (Zhou et al., 2017b) | |
112 | fortunilides G | F | Whole | (Zhou et al., 2017b) | |
113 | fortunilides H | F | Whole | (Zhou et al., 2017b) | |
114 | fortunilides I | F | Anti-inflammatory activity | Whole | (Zhou et al., 2017b) |
115 | fortunilides J | F | Whole | (Zhou et al., 2017b) | |
116 | fortunilides K | F | Whole | (Zhou et al., 2017b) | |
117 | fortunilides L | F | Whole | (Zhou et al., 2017b) | |
118 | fortunoid A | F | Antimalarial activities | Whole | (Zhou et al., 2017b) |
119 | fortunoid B | F | Antimalarial activities | Whole | (Zhou et al., 2017b) |
120 | fortunoid C | F | Aerial | (Zhou et al., 2017b) | |
121 | shizukaol P | F | Aerial | (Zhou et al., 2017b) | |
122 | 9-O-β-glucopyranosylcycloshizukaol A | F | Aerial | (Wang et al., 2009) | |
123 | cycloshizulkaol A | F | Anti-tumor activity | Aerial | (Wang et al., 2009) |
124 | shizukaol L | F | Roots | (Gong et al., 2021) | |
125 | shizukaol O | F | Anti-inflammatory activity Anti-tumor activity |
Roots | (Gong et al., 2021) (Zhang et al., 2012a) |
126 | cihoranhtaol A | F | Whole | (Luo et al., 2009) | |
127 | chioranthaol B | F | Whole | (Luo et al., 2009) | |
128 | chioranthaol C | F | Whole | (Luo et al., 2009) | |
129 | chlorahololide G | G | Whole | (Xu, 2016) | |
130 | chlorahololide B | G | Inhibiting K+ channels | Whole | (Xu, 2016) |
131 | chloramultiol D | G | Whole | (Xu, 2016) | |
132 | chlorahololide F | G | Inhibiting K+ channels | Whole | (Xu, 2016) (Yang et al., 2008) |
133 | sarcandrolide D | G | Whole | (Xu, 2016) | |
134 | henriol C | GJ | Roots | (Xu, 2016) | |
135 | chlotrichenes A | G | Roots | (Chi et al., 2019) | |
136 | chlotrichenes B | G | Anti-tumor activity | Roots | (Chi et al., 2019) |
137 | chololactone A | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
138 | chololactone B | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
139 | chololactone C | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
140 | chololactone D | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
141 | chololactone E | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
142 | chololactone F | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
143 | chololactone G | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
144 | chololactone H | G | Anti-inflammatory activity | Roots | (Shen et al., 2017) |
145 | multistalides A | G | Whole | (Zhang et al., 2010) | |
146 | multistalides B | G | Whole | (Zhang et al., 2010) | |
147 | chloraserrtone A | J | Roots | (Bai et al., 2019) | |
148 | chlorahololide A | F | Inhibiting K+ channels | Whole | (Zhou et al., 2017b) |
149 | chlorahololide E | F | Inhibiting K+ channels | Whole | (Zhou et al., 2017b) (Yang et al., 2008) |
150 | shizukaol | F | Whole | (Wang et al., 2009) | |
151 | 13′-acetylshizukaol C | F | Whole | (Gong et al., 2021) | |
152 | chloramuhilide B | F | Whole | (Gong et al., 2021) | |
153 | chlorahupetone A | L | Antitumor activity | Whole | (Zhang et al., 2021) |
154 | chlorahupetone B | L | Whole | (Zhang et al., 2021) | |
155 | chlorahupetone C | L | Whole | (Zhang et al., 2021) | |
156 | chlorahupetone D | L | Whole | (Zhang et al., 2021) | |
157 | chlorahupetone E | L | Whole | (Zhang et al., 2021) | |
158 | chlorahupetone F | L | Whole | (Zhang et al., 2021) | |
159 | chlorahupetone G | L | Antitumor activity | Whole | (Zhang et al., 2021) |
160 | chlorahupetone H | L | Antitumor activity | Whole | (Zhang et al., 2021) |
161 | chlorahupetone I | L | Antitumor activity | Whole | (Zhang et al., 2021) |
Eudesmane Sesquiterpenes | |||||
162 | serralactones A | J | Whole | (Teng et al., 2010) | |
163 | serralactones B | J | Whole | (Teng et al., 2010) | |
164 | serralactones C | J | Whole | (Teng et al., 2010) | |
165 | serralactones D | J | Whole | (Teng et al., 2010) | |
166 | neolitacumone B | J | Whole | (Teng et al., 2010) | |
167 | 1β,4β-dihydroxy-5α,8β(H)-eudesm-7(11)Z-en-8,12-olide | C | Aerial | (Yang et al., 2007a) | |
168 | 1β,4α-dihydroxy-5α,8β(H)-eudesm-7(11)Z-en-8,12-olide | C | Aerial | (Yang et al., 2007a) | |
169 | homalomenol A | C | Aerial | (Yang et al., 2007a) | |
170 | oplodiol | C | Aerial | (Yang et al., 2007a) | |
171 | chlospicates A | C | Whole | (Yang et al., 2007a) | |
172 | chlospicates B | C | Whole | (Yang et al., 2007a) | |
173 | codonolactone | L | Whole | (Wang et al., 2014a) | |
174 | 5-eudesmene-1β,4α-diol | C | Whole | (Yang et al., 2007a) | |
175 | 4α,8β-dihydroxyeudesm-7(11)-en-8,12-olide | D | Antimicrobial activity | Roots | (Wang et al., 2014a) |
176 | 4β,7β,11-enantioeudesmantriol | D | Roots | (Xu, 2016) | |
177 | 9α-hydroxycurcolonol | D | Antimicrobial activity | Roots | (Yang et al., 2014) (Wang et al., 2014a) |
178 | 3α-hydroxy-4-deoxy-5-dehydrocurcolonol | D | Antimicrobial activity | Roots | (Yang et al., 2014) (Wang et al., 2014a) |
179 | 9α-curcolonol | DFJ | Antimicrobial activity | Roots | (Yang et al., 2014) (Wang et al., 2014a) |
180 | 4α-hydroxy5α,8β(H)-eudesm-7(11)-en-8,12-olide monohydrate | E | Whole | (Lu et al., 2015) | |
181 | shizukafuranol | E | Whole | (Kawabata et al., 1984) | |
182 | shizukolidol | E | Whole | (Kawabata et al., 1984) | |
183 | 1β,10β-dihydroxy-eremophil-7(11),8-dien-12,8-olide | E | Whole | (Lu et al., 2016) | |
184 | 8,12-epoxy-1β-hydroxyeudesm-3,7,11-trien-9-one | E | Whole | (Lu et al., 2016) | |
185 | 4α-hydroxy-5α(H)-8β-methoxy-eudesm-7(11)-en-12,8-olide | E | Whole | (Lu et al., 2016) | |
186 | CJ-01 | E | Antimicrobial activity | Whole | (Yim et al., 2008) |
187 | chlojaponilactone A | E | Whole | (Fang, 2011) | |
188 | tsoongianolide D | E | Whole | (Yan et al., 2013) | |
189 | tsoongianolide E | E | Whole | (Yan et al., 2013) | |
190 | (10α)-10-hydroxy-1-oxoeremophila-7(11),8-dien-12,8-olide | E | Whole | (Yan et al., 2013) | |
191 | chlorajapolides I | E | Aerial | (Zhang et al., 2012a) | |
192 | chlojaponols A | E | Whole | (Li et al., 2016) | |
193 | chlojaponols B | E | Antimicrobial activity | Whole | (Li et al., 2016) |
194 | chlorajapotriol | E | Whole | (Zhuo et al., 2017) | |
195 | chloraeudolide | E | Antitumor activity | Whole | (Wang et al., 2011) |
196 | chlorantene B | E J | Whole | (Yuan et al., 2008) | |
197 | chlorantene C | EJ | Neuroprotective activity | Whole | (Yuan et al., 2008) (Chen et al., 2021a) |
198 | chlorantene D | EJ | Antibacterial activity | Whole | (Yuan et al., 2008) |
199 | chlorantene G | E | Antibacterial activity | Whole | (Yuan et al., 2008) |
200 | atractylenolactam | F | Whole | (Wang et al., 2008) | |
201 | curcodione | F | Neuroprotective activity | Whole | (Chen et al., 2021a) |
202 | 1β,8β-dihydroxyeudesman −3,7(11)-dien-8α,12-olide | G | Whole | (Xu, 2016) | |
203 | 4(15)-eudesmene-1β,7α,11-triol | G | Whole | (Xu, 2016) | |
204 | 3,4,8α-trimethyl-4α,7,8,8α-tetrahydro-4α-naphto[2,3-b]furan-9-one | G | Whole | (Zhan et al., 2021) | |
205 | (5S,10S)-9-Oxo-atractylon | H | Whole | (Xu et al., 2018) | |
206 | chlorantene J | H | Whole | (Xu et al., 2018) | |
207 | (7R,10S)-7-hydroxyeudesm-4-en-3,6-dione | H | Whole | (Xu et al., 2018) | |
208 | 1α-hydroxy-4αH,5αH-eudesma-7,11-diene-6,9-dione | H | Whole | (Xu et al., 2018) | |
209 | 4α-hydroxy-8,12-epoxyeudesma-7,11-diene-1,6-dione | H | Whole | (Xu et al., 2018) | |
210 | (3R)-3-hydroxyatractylenolide III | H | Roots | (Xu et al., 2010) | |
211 | 8β-hydroxy-1-oxoeudesma-3,7(11)-dien-12,8α-olide | H | Roots | (Xu et al., 2010) | |
212 | chlorantene M | J | Whole | (Huang et al., 2021) | |
213 | 5α,7α(H)-6,8-cycloeudesma-1β,4β-diol | C | Aerial | (Yang et al., 2007a) | |
214 | 5α-(cinnamoyloxy)-8,12-epoxy-3-methoxy-7βH,8αH-eudesma-3,11-dien-6-one | E | Aerial | (Fang, 2011) | |
215 | 8β-(cinnamoyloxy)eudesma-4(14),7(11)-dien-12,8-olide | E | Aerial | (Fang, 2011) | |
216 | 8,12-epoxy-1α-hydroxy-4αH,5αH-eudesma-7,11-diene-6,9-dione | E | Aerial | (Fang, 2011) | |
217 | 8,12-epoxy-1α-methoxy-4αH,5αH-eudesma-7,11-diene-6,9-dione | E | Aerial | (Fang, 2011) | |
218 | sarcaglaboside A | E | Hepatoprotective activity | Aerial | (Fang, 2011) (Li et al., 2006) |
219 | chlorajapodiolide | E | Whole | (Fang, 2011) | |
220 | chloranholide A | G | Whole | (Zhan et al., 2021) | |
221 | 1α-methoxy-8,12-epoxyeudesma-4,7,11-trien-6-one | L | Steem | (Wu et al., 2008) | |
222 | 11,12,13-trihydroxyeudesma-4(15),8-dien-9-one | L | Steem | (Wu et al., 2008) | |
223 | 1α-hydroxy-8,12-epoxyeudesma-4,7,11-triene-3,6-dione | L | Roots | (Gan et al., 2009) | |
224 | curcolone | L | Roots | (Gan et al., 2009) | |
225 | endesm-4(15)-en-7α,11-diol | L | Roots | (Gan et al., 2009) | |
226 | 1α-hydroxy-8,12-epoxyeudesma-4,7,11-triene-6,9-dione | L | Antitumor activity | Whole | (Wu et al., 2006) |
Germacrane Sesquiterpenes | |||||
227 | germacra-5E,10(14)-dien-1β,4β-diol | C | Whole | (Yang et al., 2012) | |
228 | 4α,5α-epoxy1(10),7(11)-dienegermacr-8α,12-olide | C | Whole | (Yang et al., 2012) | |
229 | furanodienone | DE | Roots | (Yang et al., 2014) | |
230 | glechomanolid | E | Aerial | (Kawabata et al., 1981) | |
231 | isofuranodiene | E | Aerial | (Kawabata et al., 1981) | |
232 | chlorantene E | EJ | Anti-bacterial activity | Whole | (Yuan et al., 2008) |
233 | chloranthatone | F | Roots | (Wang et al., 2008) | |
234 | zederone | F | Neuroprotective activity | Whole | (Chen et al., 2021a) |
235 | (1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone | F | Neuroprotective activity | Whole | (Wu et al., 2008) (Chen et al., 2021a) |
236 | 8-methoxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone | L | Steem | (Wu et al., 2008) | |
237 | zederone epoxide | F | Antitumor activity Anti-neuroinflammatory activity Neuroprotective activity |
Whole | (Wang et al., 2014a) (Chen et al., 2021a) |
238 | 4β,5α-dihydroxy-10(β)H-8,12-epoxygermacra-7,11-diene-9-one | G | Whole | (Xu, 2016) | |
239 | curcuzederone | H | Whole | (Xu et al., 2018) | |
240 | 15-hydroxy-11βH-8-oxogermacra-1(10),4-dieno-12,6α-lactone | L | Steem | (Wu et al., 2008) | |
241 | (1S,4S,5S,10S)-1,10:4,5-diepoxygermacrone | L | Whole | (Wang et al., 2014a) | |
242 | chlogermacrone A | L | Roots | (Chen et al., 2020) | |
243 | chlogermacrone C | L | Neuroprotective effects activity | Roots | (Chen et al., 2020) |
Cadinane Sesquiterpenes | |||||
244 | (7R,9S,10R)-3,9-di-hidroxicalameneno | G | Whole | (Xu, 2016) | |
245 | chloranholide B | G | Whole | (Zhan et al., 2021) | |
246 | chloranholide C | G | Whole | (Zhan et al., 2021) | |
247 | chloranholide D | G | Anti-inflammatory activity | Whole | (Zhan et al., 2021) |
248 | phacadinane E | H | Whole | (Xu et al., 2018) | |
249 | chlomultin C | H | Whole | (Xu et al., 2018) | |
250 | chlorantene N | K | Whole | (Huang et al., 2021) | |
251 | (4α)-8-hydroxy-12-norcardina-6,8,10-trien-11-one | L | Whole | (Wang et al., 2014a) | |
252 | (4α,11β)-8,11-dihydroxycadina-6,8,10-trien-12-oic acid g-lactone | L | Whole | (Wang et al., 2014a) | |
253 | 4-epimer | L | Whole | (Wang et al., 2014b) | |
254 | (8α)-6,8-dihydroxycadina-7(11),10(15)-dien-12-oic acid g-lactone1) | L | Anti-tumor activity | Steem | (Wu et al., 2007) |
255 | tanapraetenolide | L | Steem | (Wu et al., 2007) | |
256 | dayejijiol | L | Anti-tumor activitity | Whole | (Wu et al., 2006) |
Guaiane Sesquiterpenes | |||||
257 | (1R,4S,5R,8S,10S)-Zedoalactone A | K | Whole | (Liu et al., 2013) | |
258 | multistalactone D | K | Whole | (Liu et al., 2013) | |
259 | multistalactone E | K | Whole | (Liu et al., 2013) | |
260 | multistalactone F | K | Whole | (Liu et al., 2013) | |
261 | chlospicate D | C | Whole | (Yang et al., 2012) | |
262 | chloraniolide A | H | Whole | (Xu et al., 2010) | |
263 | chlospicates C | C | Whole | (Yang et al., 2012) | |
264 | chlohenriol A | L | Neuroprotective activitity | Roots | (Chen et al., 2021c) |
265 | chlohenriol B | L | Neuroprotective activitity | Roots | (Chen et al., 2021c) |
266 | chlohenriol C | L | Neuroprotective activitity | Roots | (Chen et al., 2021c) |
Acorane Sesquiterpenes | |||||
267 | shizuka-acoradienol | EF | Roots | (Kawabata et al., 1984) | |
268 | spiro[4.5]dec-6-ene-8α,9β,15α-triol,4β-methyl-1α-isopropyl | G | Whole | (Xu, 2016) | |
269 | Spiro[4.5]dec-6-ene-8β,9β,15α-triol,4β-methyl-1α-isopropyl | G | Whole | (Xu, 2016) | |
270 | 8-desmethylacor-6,9-dien-8-one-3α-ol | G | Whole | (Xu, 2016) | |
Eremophilane Sesquiterpenes | |||||
271 | (3R,4S,5R,10S,11S)-3-hydroxy-8-oxo-6-eremophilen-12-oic acid | H | Leaves | (Wu et al., 2010) | |
272 | Anhuienol | H | Leaves | (Wu et al., 2010) | |
273 | (3R,4S,5R,6R,8R,10S)-3,6,8-trihydroxy-7(11)-eremophilen-12,8-olide | H | Leaves | (Wu et al., 2010) | |
274 | 3R,6R-dihydroxy-8αH-7(11)-eremophilen-12,8-olide | H | Leaves | (Wu et al., 2010) | |
275 | anhuienoside A | H | Leaves | (Wu et al., 2010) | |
276 | 6αH,8αH-7(11)-eremophilen-12,8:15,6-diolide | H | Leaves | (Wu et al., 2010) | |
277 | (7α)-8-oxoeudesm-4(14)-en-12-oic acid | L | Leaves | (Wu et al., 2010) | |
Oplopanone Sesquiterpenes | |||||
278 | oplopanone | C | Aerial | (Yang et al., 2007a) | |
Drimane Sesquiterpene | |||||
279 | 11- hydroxydrim-8,12-en-14-oic acid | L | Whole | (Gan et al., 2009) | |
Elemene Sesquiterpene | |||||
280 | curzerenone | F | Neuroprotective activity | Whole | (Chen et al., 2021a) |
281 | isogermafurenolide | H | Whole | (Xu et al., 2018) | |
Brasilane Sesquiterpene | |||||
282 | chlospicates E | C | Whole | (Yang et al., 2012) | |
Others Sesquiterpene | |||||
283 | chloranholides E | G | Whole | (Zhan et al., 2021) | |
284 | chlorantolide A | H | Whole | (Xu et al., 2018) | |
285 | (7S,1(10)Z)-4,5-secoguaia-1(10),11-diene-4,5-dione | L | Whole | (Wang et al., 2014b) | |
286 | chlogermacrone B | L | Roots | (Chen et al., 2020) | |
Monoterpenes | |||||
287 | pressafonin | D | Roots | (Wang et al., 2014a) | |
288 | (3R,4S,6R)- p-menth-1-en-3,6-diol | E | Whole | (Lu et al., 2016) | |
289 | (R)-p-menth-1-en-4,7-diol | E | Whole | (Lu et al., 2016) | |
290 | (–) loliolide | F | Whole | (Chen et al., 2021a) | |
Diterpenoids | |||||
291 | 13-epitorulosol | FJ | Whole | (Chen et al., 2019) | |
292 | (12R,13E)-15-(acetoxy)-12-hydroxylabda-8(20),13-dien-19-oic acid | H | Roots | (Xu et al., 2010) | |
293 | (12S,13E)-15-(acetoxy)-12-dihydroxylabda-8(20),13-dien-19-oic acid | H | Roots | (Xu et al., 2010) | |
294 | 12R,13S-dihydroxylabda-8(17),14-dien-19-oic acid | J | Roots | (Chen et al., 2019) | |
295 | henrilabdane A | J | Roots | (Chen et al., 2019) | |
296 | henrilabdane C | J | Roots | (Chen et al., 2019) | |
297 | 12S,15-dihydroxylabda-8(17),13E-dien-19-oic acid | J | Roots | (Chen et al., 2019) | |
298 | henrilabdane B | J | Roots | (Chen et al., 2019) | |
299 | 12,15-expoxylabda-8(17),13-dien-19-oic acid | J | Roots | (Chen et al., 2019) | |
300 | serralabdanes A | J | Anti-inflammatory activity | Whole | (Zhang et al., 2013) |
301 | serralabdanes B | J | Anti-inflammatory activity | Whole | (Zhang et al., 2013) |
302 | serralabdanes C | J | Anti-inflammatory activity | Whole | (Zhang et al., 2013) |
303 | serralabdanes D | J | Anti-inflammatory activity | Whole | (Zhang et al., 2013) |
304 | serralabdanes E | J | Anti-inflammatory activity | Whole | (Zhang et al., 2013) |
305 | ent-17-hydroxyl-16-methoxyl-kauran-3-one | K | Whole | (Luo et al., 2014) | |
306 | ent-17-acetoxyl-16-methoxyl-kauran-3-one | K | Whole | (Luo et al., 2014) | |
307 | ent-17-hydroxylkaur-15-en-3-one | K | Whole | (Luo et al., 2014) | |
308 | ent-3-acetoxyl-kaur-15-en-16, 17-diol | K | Whole | (Luo et al., 2014) | |
309 | ent-kauran-3, 16, 17-triol | K | Whole | (Luo et al., 2014) | |
310 | ent-3-acetoxyl-kauran-16, 17-diol | K | Whole | (Luo et al., 2014) | |
311 | ent-kauran-16, 17-diol | K | Whole | (Luo et al., 2014) | |
312 | abbeokutone | K | Whole | (Luo et al., 2014) | |
313 | ent-17α-acetyl-16β-hydroxyl- kauran-3-one | K | Anti-tumor activity | Whole | (Luo et al., 2014) |
314 | 15-norlabda-8(20),12E-diene-14-carboxalde-19-oic acid | C | Whole | (Yang et al., 2012) | |
315 | 12R,15-dihydroxy-8(17),13E-labdadien-19-oic acid | D | Roots | (Wang et al., 2014a) | |
316 | chloranhenryin A | L | Whole | (Xie et al., 2015) | |
317 | oryzalexin A | L | Whole | (Xie et al., 2015) | |
318 | 15-hydroxysessilifol F | L | Whole | (Xie et al., 2015) | |
319 | decandrin B | L | Whole | (Xie et al., 2015) | |
320 | sessilifol F | L | Anti-inflammatory activity | Whole | (Xie et al., 2015) |
321 | 13-O-methylsessilifol D | L | Whole | (Xie et al., 2015) | |
322 | sessilifol D | L | Whole | (Xie et al., 2015) | |
323 | chloranhenryin B | L | Antibacterial activity | Whole | (Xie et al., 2015) |
324 | chloranhenryin C | L | Whole | (Xie et al., 2015) | |
325 | 15-O-methylsessilifol J | L | Whole | (Xie et al., 2015) | |
326 | chloranhenryin D | L | Whole | (Xie et al., 2015) | |
327 | chloranhenryin E | L | Whole | (Xie et al., 2015) | |
328 | chloranhenryin F | L | Whole | (Xie et al., 2015) | |
329 | 15-ene-3α,8α-diol | L | Whole | (Xie et al., 2015) | |
330 | ent-pimara-8(14),15-diene-3α,7β-diol | L | Antibacterial activity | Whole | (Xie et al., 2015) |
331 | 3β-hydroxyabieta-8,11,13-trien-7-one | L | Antibacterial activity | Whole | (Xie et al., 2015) |
332 | 3β,7α-dihydroxyabieta-8,11,13-triene | L | Antibacterial activity | Whole | (Xie et al., 2015) |
333 | sessilifol O | L | Whole | (Xie et al., 2015) | |
334 | henrilabdanes A | L | Hepatoprotective activity | Roots | (Li et al., 2008) |
335 | henrilabdanes C | L | Hepatoprotective activity | Roots | (Li et al., 2008) |
336 | henrilabdanes B | L | Hepatoprotective activity | Roots | (Li et al., 2008) |
337 | (13S)-13-hydroxy-19-methoxy-5αH-8(17),14-labdadien | L | Whole | (Wu et al., 2006) | |
338 | 7β,12α-Dihydroxy-13-epi-manoyl oxide | L | Roots | (Gan et al., 2009) | |
339 | 7β,12α-Dihydroxymanoyl oxide | L | Roots | (Gan et al., 2009) | |
340 | (12R)-Labda-8(17),13E-dien-12,15,19-triol | L | Roots | (Gan et al., 2009) | |
341 | 15-Nor-14-oxolabda-8(17),12E-dien-19-ol | L | Roots | (Gan et al., 2009) | |
342 | 12(R)-12,15-dihydroxylabda-8(17),13E-dien-19-oic acid | L | Roots | (Gan et al., 2009) | |
343 | 15-hydroxy-12-oxolabda-8(17),13E-dien-19-oic acid | L | Roots | (Gan et al., 2009) | |
344 | 15-nor-14-oxolabda-8(17),12E-dien-19-oic acid | L | Roots | (Gan et al., 2009) | |
345 | (12R),(13S)-12,13-dihydroxylabda-8(17),14-dien-19-oic acid | L | Roots | (Gan et al., 2009) | |
346 | (12S)-12,15-dihydroxylabda-8(17),13E-dien-19-oic acid | L | Roots | (Gan et al., 2009) | |
347 | 12,15-Epoxy-5αH,9βH-labda-8(17),13-dien-19-oic acid | L | Whole | (Wu et al., 2006) | |
348 | 14-methoxy-15,16-dinor-5αH,9αH-labda-13(E),8(17)-dien-12-one | L | Antitumor activity | Whole | (Wu et al., 2006) |
349 | (3R,5S,9R,10S)-3-hydroxy-ent-podocarpa-8(14)-ene-13-one | M | Whole | (Wang et al., 2015b) | |
350 | 3α-hydroxy-ent-torara-8-en-7,13-dione | M | Whole | (Wang et al., 2015b) | |
351 | decandrin G | M | Whole | (Wang et al., 2015b) | |
352 | 3α,7β-dihydroxyabieta-8,11,13-triene | M | Anti-inflammatory activity | Whole | (Wang et al., 2015b) |
353 | decandrin B | M | Whole | (Wang et al., 2015b) | |
354 | sessilifol A | M | Whole | (Wang et al., 2015b) | |
355 | sessilifol B | M | Whole | (Wang et al., 2015b) | |
356 | sessilifol C | M | Whole | (Wang et al., 2015b) | |
357 | sessilifol G | M | Whole | (Wang et al., 2015b) | |
358 | sessilifol H | M | Whole | (Wang et al., 2015b) | |
359 | sessilifol I | M | Anti-inflammatory activity | Whole | (Wang et al., 2015b) |
360 | sessilifol J | M | Whole | (Wang et al., 2015b) | |
361 | sessilifol K | M | Whole | (Wang et al., 2015b) | |
362 | sessilifol M | M | Whole | (Wang et al., 2015b) | |
363 | sessilifol N | M | Whole | (Wang et al., 2015b) | |
364 | sessilifol P | M | Whole | (Wang et al., 2015b) | |
365 | sessilifol Q | M | Whole | (Wang et al., 2015b) | |
366 | chlorabietol A | N | Inhibition of PTP1B activity Hypoglycemic Activity |
Roots | (Xiong et al., 2015) (Xiong et al., 2015) |
367 | chlorabietol B | N | Inhibition of PTP1B activity Hypoglycemic Activity |
Roots | (Xiong et al., 2015) (Xiong et al., 2016) |
368 | chlorabietol C | N | Inhibition of PTP1B activity Hypoglycemic Activity |
Roots | (Xiong et al., 2015) (Xiong et al., 2016) |
369 | 19-Hydroxy-ent-abieta-7,13-diene | N | Roots | (Xiong et al., 2015) | |
370 | chlorabietin A | N | Roots | (Xiong et al., 2016) | |
371 | chlorabietin B | N | Anti-inflammatory activity | Roots | (Xiong et al., 2016) |
372 | chlorabietin C | N | Anti-inflammatory activity | Roots | (Xiong et al., 2016) |
373 | chlorabietin D | N | Roots | (Xiong et al., 2016) | |
374 | chlorabietin E | N | Roots | (Xiong et al., 2016) | |
375 | chlorabietin F | N | Anti-inflammatory activity | Roots | (Xiong et al., 2016) |
376 | chlorabietin G | N | Anti-inflammatory activity | Roots | (Xiong et al., 2016) |
377 | chlorabietin H | N | Roots | (Xiong et al., 2016) | |
378 | chlorabietin I | N | Roots | (Xiong et al., 2016) | |
379 | chlorabietin K | N | Roots | (Xiong et al., 2016) | |
Triterpenoids | |||||
380 | 2β,9α-dihydroxy-5α-methoxyergosta-7,22-diene | JK | Whole | (Shen et al., 2016) | |
381 | 2β,6β-dihydroxy-5α-methoxyergosta-7,22-diene | JK | Whole | (Shen et al., 2016) | |
C25 Terpenoids | |||||
382 | hitorins A | E | Aerial | (Kim et al., 2016) | |
383 | hitorins B | E | Aerial | (Kim et al., 2016) | |
Coumarins | |||||
384 | isofraxidin | DEH | choleretic activity | Whole | (Zhu et al., 2018) |
385 | scopoletin | E | Whole | (Kawabata et al., 1984) (Kawabata et al., 1984) | |
386 | isoscopoletin | E | Whole | (Kawabata et al., 1984) | |
387 | isofraxidin-7-O-β-d-glucopyranoside | E | Whole | (Heo et al., 2005) | |
Lignans | |||||
388 | (7S,8R)-dihydrodehydrodiconiferyl alcohol | E | Roots | (Kuang et al., 2009) | |
389 | (7S, 8R)-urolignoside | E | Roots | (Kuang et al., 2009) | |
390 | (7S,8R)-dihydrodehydrodiconiferyl alcohol-9-β-d-glucopyranoside | E | Roots | (Kuang et al., 2009) | |
391 | (7S,8R)-dihydrodehydrodiconiferyl alcohol-9′- O-β-d-glucopyranoside | E | Roots | (Kuang et al., 2009) | |
392 | (7S,8R)-5-methoxydihydrodehydrodiconiferyl alcohol-4-O-β-d-glucopyranoside | E | Roots | (Kuang et al., 2009) | |
393 | (±)-erythro-guaiacyl-glycerol-β-O-4′-dihydroconiferylether | D | Aerial | (Du et al., 2017) | |
Simple phenylpropanoids | |||||
394 | (E)-cinnamic acid | D | Roots | (Wang et al., 2014a) | |
395 | p-coumaric acid | F | Whole | (Chen et al., 2021a) | |
Flavonoids | |||||
396 | 7,4′-dimethylnaringenin | F | Whole | (Chen et al., 2021a) | |
397 | quercetin-3-O-α-l-rhamnopyranoside | F | Whole | (Chen et al., 2021a) | |
398 | quercetin-3-O-β-d-glucopyranoside | F | Whole | (Chen et al., 2021a) | |
399 | catechin | F | Whole | (Chen et al., 2021a) | |
Organic acids | |||||
400 | stearic acid | D | Roots | (Wang et al., 2014a) | |
401 | vanillic acid | D | Roots | (Wang et al., 2014a) | |
402 | 4-Hydroxybenzoic acid | G | Whole | (Xu, 2016) | |
403 | trans-4-Hydroxy-2-nonenoic acid | G | Whole | (Xu, 2016) | |
404 | 3,4,5-trimethoxybenzaldehyde | H | Leaves | (Wu et al., 2010) | |
Amide | |||||
405 | N-p-trans-coumaroyltyramine | D | Aerial | (Xu, 2016) | |
406 | N-p-trans-feruloyltyramine | D | Aerial | (Xu, 2016) | |
407 | cannabisin G | D | Aerial | (Xu, 2016) | |
408 | thoreliamide A | D | Aerial | (Xu, 2016) | |
409 | cannabisin F | D | Aerial | (Xu, 2016) | |
410 | aurantiamide acetate | D | Aerial | (Xu, 2016) | |
Others compounds | |||||
411 | (E)-5-(4-methoxyphenyl)-4-ene-1,2,3-trihydroxyamyl | D | Aerial | (Du et al., 2017) | |
412 | 1-acetoxy-2,3,4,5-tetrahydroxy-5-p-metoxyphenylpentane | D | Aerial | (Du et al., 2017) | |
413 | (−)-rosiridol | D | Aerial | (Du et al., 2017) | |
414 | (4S)-p-menth-1-ene-4,7-diol | D | Aerial | (Du et al., 2017) | |
415 | pisumionoside | E | Whole | (Kuang et al., 2008) | |
416 | yinxiancaoside B | E | Antitumor activity | Whole | (Kuang et al., 2008) |
417 | yinxiancaoside C | E | Antitumor activity | Roots | (Kuang et al., 2008) |
418 | vomifoliol | F | Whole | (Chen et al., 2021a) |
Note: B: Chloranthus elatior Link. C: Chloranthus spicatus (Thunb.) Makino.
D: Chloranthus angustifolius Oliv. E: Chloranthus japonicus Sieb.
F: Chloranthus fortunei (A. Gray) Solms-Laub. G: Chloranthus holostegius (Hand. -Mazz.) Pei et Shan.
H: Chloranthus anhuiensis K. F. Wu. I: Chloranthus tianmushanensis K. F. Wu.
J: Chloranthus serratus (Thunb.) Roem. et Schult. K: Chloranthus multistachys Pei.
L: Chloranthus henryi Hemsl. M: Chloranthus sessilifolius K. F. Wu.
N: Chloranthus oldhamii Solms Laubach.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of lindenane sesquiterpenes and their polymers in genus Chloranthus.

- Structures of eudesmane sesquiterpenes in genus Chloranthus.

- Structures of eudesmane sesquiterpenes in genus Chloranthus.

- Structures of germacrane sesquiterpenes in genus Chloranthus.

- Structures of cadinane sesquiterpenes in genus Chloranthus.

- Structures of guaiane sesquiterpenes in genus Chloranthus.

- Structures of acorane sesquiterpenes in genus Chloranthus.

- Structures of eremophilane sesquiterpenes in genus Chloranthus.

- Structures of oplopanone sesquiterpenes, drimane sesquiterpene, elemene sesquiterpene and brasilane sesquiterpene in genus Chloranthus.

- Structures of others sesquiterpene in genus Chloranthus.

- Structures of monoterpenes in genus Chloranthus.

- Structures of diterpenoids in genus Chloranthus.

- Structures of diterpenoids in genus Chloranthus.

- Structures of diterpenoids in genus Chloranthus.

- Structures of triterpenoids in genus Chloranthus.

- Structures of C25 terpenoids in genus Chloranthus.

- Structures of coumarins in genus Chloranthus.

- Structures of lignans and simple phenylpropanoids in genus Chloranthu.

- Structures of flavonoids in genus Chloranthus.

- Structures of Organic acids in genus Chloranthus.

- Structures of amides in genus Chloranthus.

- Structures of others compounds in genus Chloranthus.
5.1 Sesquiterpenes
Sesquiterpenoids are the main types of chemical constituents in the genus Chloranthus, as well as its main active ingredients. At present, 286 sesquiterpenes were isolated from this genus, mainly distributed in C. japonicus, C. fortunei, C. holostegius and C. spicatus plants, and the structural types include lindenane sesquiterpenes and their polymers (1–161), eudesmane sesquiterpenes (162–226), germacrane sesquiterpenes (227–243), cadinane sesquiterpenes (244–256), guaiane sesquiterpenes (257–266), acorane sesquiterpenes (267–270), eremophilane sesquiterpenes (271–277), oplopanone sesquiterpenes (278), drimane sesquiterpene (279), elemene sesquiterpene (280–281), brasilane sesquiterpene (282) and others sesquiterpene (Wang et al., 2015a; Xu, 2013).
Among them, lindenane sesquiterpenes, sesquiterpenes dimers and eudesmane sesquiterpenes are the most abundant. In particular, sesquiterpene dimers, as indicator components of this genus, which have diverse structural types and significant pharmacological activities (Ma et al., 2020). The specific compound names and structures are shown in Table 1 and Figs. 1–9.
5.2 Monoterpenes
Monoterpenes are less abundant in the genus Chloranthus, and four compounds (287–290) were reported. Wang et al. isolated a monoterpene lactone (287) pressafonin from C. angustifoliu (Wang et al., 2014a). Lu et al. obtained two monoterpenes (3R,4S,6R)-p-menth-1-en-3,6-diol and (R)-p-menth-1-en-4,7-diol from C. japonicus (Lu et al., 2016). (–) loliolide was first isolated from C. fortunei (Chen et al., 2021a). The specific compound names and structures are shown in Table 1 and Fig. 10.
5.3 Diterpenoids
Diterpenoids are abundant in the genus Chloranthus and they are an important source of activity in this genus. So far, a total of 88 compounds (291–379) were isolated from this genus, and the main structural types include abietane diterpenes, pimarane diterpenes, totarane diterpenes, labdane diterpenes and ring-opened chinane diterpenes (Chen et al., 2021b). Among them, the norditerpenoids are new diterpenoid structure types in this genus, and their carbon skeletons are mostly C18 and C19. Xie et al. (2015). reported that chloranhenryin D (326) from C. henryi was a abietane-type diterpenoid at the absence of C-14 position. Wang et al. (2015c). isolated a new ent-podocarpane-type C17 norditerpenoid compound (3R,5S,9R,10S)-3-hydroxy-ent-podocarpa-8(14)-ene-13-one from C. sessilifolius. Furthermore, three new norditerpenoid compounds sessilifol O (333), sessilifol P (364)and sessilifol Q (365), were also isolated from C. serratus (Wang et al., 2015b). The specific compound names and structures are shown in Table 1 and Fig. 11.
5.4 Triterpenoids
Shen et al. identified two new triterpenoids, 2β, 9α-dihydroxy-5α-me-thoxyergosta-7,22-diene (380) and 2β, 6β-dihydroxy-5α-methoxyergosta-7, 22-diene (381)from the leaves of C. multistachys (Shen et al., 2016). The specific compound names and structures are shown in Table 1 and Fig. 12.
5.5 C25 terpenoids
Two new C25 Terpenoids, hitorins A (3 8 2) and hitorins B (3 8 3), were identified from C. japonicus, which has a 6/5/5/5/5/3 hexacyclic skeleton including one γ-lactone ring and two tetrahydrofuran rings (Kim et al., 2016). The specific compound names and structures are shown in Table 1 and Fig. 13.
5.6 Coumarins
A total of four coumarins isofraxidin (384), scopoletin (385), isoscopoletin (386) and isofraxidin-7-O-β-d-glucopyranoside (387) were isolated from the genus Chloranthus, and most of them were distributed in C. japonicus (Zhu et al., 2018; Kawabata et al., 1984; Heo et al., 2005). The specific compound names and structures are shown in Table 1 and Fig. 14.
5.7 Lignans
Kuang et al. and Du et al. isolated six new lignans (388–393) from the root parts of C. japonicus and aboveground parts of C. angustifolius, respectively (Kuang et al., 2009; Du et al., 2017). The specific compound names and structures are shown in Table 1 and Fig. 15.
5.8 Simple phenylpropanoids
At present, only two simple phenylpropanes, (E)-cinnamic acid (394) and p-coumaric acid (395), have been isolated from C. angustifolius and C. fortunei (Wang, 2014; Chen et al., 2021a). The specific compound names and structures are shown in Table 1 and Fig. 15.
5.9 Flavonoids
In recent years, there are relatively few reports on flavonoids in the genus Chloranthus. Chen et al. isolated four flavonoids (396–399) from C. fortunei for the first time (Chen et al., 2021a). The specific compound names and structures are shown in Table 1 and Fig. 16.
5.10 Organic acids
The content of organic acids in the genus Chloranthus is low, and five organic acids compounds (400–404) were found in C. angustifolius and C. Holostegius (Wang et al., 2014a; Xu, 2016; Wu et al., 2010). The specific compound names and structures are shown in Table 1 and Fig. 17.
5.11 Amides
Liu et al. isolated six amides (405–410) from C. angustifolius, all of which were found and reported for the first time in the genus Chloranthus (Liu et al., 2015). The specific compound names and structures are shown in Table 1 and Fig. 18.
5.12 Others compounds
Besides, eight other types of compounds were discovered in this genus. The specific compound names and structures are shown in Table 1 and Fig. 18.
5.13 Pharmacological activity
Modern pharmacological experiments indicated that most species of the genus Chloranthus have anti-cancer, antibacterial, antiviral, hypoglycemic anti-inflammatory, and antimalarial activities (Cao et al., 2008). The bioactivities of monomeric compounds in Chloranthus are listed in Table 2.
Pharmacological Action |
Effective Fraction/ Compounds | Model | Responses along with Critical Assessment |
Target or Possible Mechanism |
References |
---|---|---|---|---|---|
Anti-inflammatory activity | shizukaol B | In vitro / BV-2 microglial cells | At the concentrations ≥ 25 μM Excellent activity |
TNF-a and IL-1b | (Pan et al., 2017) |
chlorabietin B | BV-2 microglial cells | IC50 = 16.4 ∼ 33.8 μM Excellent activity |
Inhibiting NO | (Xiong et al., 2016) | |
chlorabietin C | |||||
chlorabietin F | |||||
chlorabietin G | |||||
sessilifol F | BV-2 microglial cells | IC50 = 8.3, 7.4 μM, respectively Moderate activity |
Inhibiting NO | (Wang et al., 2015b) | |
sessilifol I | |||||
3α,7β-dihydroxyabieta-8,11,13-triene | In vitro /BV-2 microglial cells | IC50 = 4.3 μM Significant activityCell viability (%) : 94.6 ± 7.9 |
Inhibiting NO | (Wang et al., 2015c) | |
shizukaolA | RAW 264.7 cells | IC50 = 7.22 μM, 3.68 μM, 0.15 μM, respectively Overall good activity |
Inhibiting NO | (Gong et al., 2021) | |
fortunilide I | |||||
shizukanolide G | |||||
chloramultilide A | BV-2 microglial cells | IC50 = 31.1 ∼ 79.4 μΜ Significant activity |
Inhibiting NO | (Wang et al., 2014b) | |
spicachlorantin G | |||||
shizukaol B | |||||
spicachlorantin B | |||||
chlorajaponol B | RAW 264.7 cells | IC50 = 9.56 ± 0.71 μMpositive control amino guanidine (IC50 = 8.50 ± 0.35 μM) Good activity |
Inhibiting NO | (Zhuo et al., 2017) | |
fortunilide K | RAW 264.7 cells | Not mentioned | Inhibiting NO | (Huang et al., 2020) | |
chlojaponilactone B | (TPA)-stimulated mice | Not mentioned | iNOS, TNF-α, IL-6, NF-κB | (Sun et al., 2020) | |
shizukaol D | RAW 264.7 cells | IC50 = 3.7 μM (cell activity (%) at an initial concentration of 50 μM) positive control l-NIL (IC50 = 7.0 μM) Good activity |
Inhibiting NO | (Bai et al., 2019) | |
henriol D | RAW 264.7 cells | IC50 = 1.90, 3.68, 1.95, 7.01, 1.95 μM, respectively Significant activity |
Inhibiting NO | (Zhang et al., 2012c) | |
shizukaol E | |||||
shizukaol G | |||||
shizukaol M | |||||
shizukaol O | |||||
chololactone A | RAW 264.7 cells | IC50 = 4.4 ∼ 35.4 μM dexamethasone as a positive control (IC50 = 0.45 ± 0.5 μM) Moderate activity |
Inhibiting NO | (Shen et al., 2017) | |
chololactone B | |||||
chololactone E | |||||
chololactone F | |||||
chololactone G | |||||
chololactone H | |||||
serralabdanes A | RAW 264.7 cells | IC50 = 38.45 ± 1.02, 29.78 ± 0.92, 44.37 ± 0.58, 53.68 ± 1.52, 47.31 ± 1.26 μM, respectivelypositive control dexamethasone (IC50 = 1.08 ± 0.15 μM) Overall good activity |
Inhibiting NO | (Zhang et al., 2013) | |
serralabdanes B | |||||
serralabdanes C | |||||
serralabdanes D | |||||
serralabdanes E | |||||
Anti-tumor activity | shizukaol D | liver cancer cells | At the concentrations ≥ 6.25 μM Excellent activity |
Wnt, β-catenin | (Tang et al., 2016) |
serralactone A | breast cancer cells | Against MDA-MB-23, MDA-MB-468 cells IC50 = 3.14 μM, 4.64 μM Excellent activity |
LIM kinase 1 | (Fu et al., 2018) | |
codonolactone | breast cancer cells | Not mentioned | Runx2 | (Wang et al., 2014b) | |
yinxiancaoside A | Hepg-2, OV420 and MCF-7 cells | Against Hepg-2, OV420, MCF-7 cell lines Marginal activity |
Not mentioned | (Kuang et al., 2009) (Kuang et al., 2008) | |
yinxiancaoside B | |||||
yinxiancaoside C | |||||
chloranoside A | |||||
pisumionoside | |||||
sarcaglaboside A | |||||
chlotrichenes B | U2 OS | Synergetic cytotoxicity with DOX on U2 OS cells (CI: 0.94 ± 0.03) |
Not mentioned | (Chi et al., 2019) | |
henriols C | BEL7402, BGC-823, HCT-8 cells | Against BEL-7402, BGC823 cells IC50 = 1.4, 3.2 μM Good activity |
Not mentioned | (Li et al., 2008) | |
henrilabdanes A | Against BEL-7402, HCT-8, BGC-823 cells IC50 = 1.7, 0.54, 5.76 μM Moderate activity |
||||
chlorahupetones A | A549, U87, SMMC-7721 cells | Against A549 cells, U87 cells, SMMC-7721 cells IC50 = 9.82 ± 1.21, 0.43 ± 0.12, 0.94 ± 0.28, 3.15 ± 1.25 μMPaclitaxel (IC50 = 1.62 ± 0.13 μM) Excellent activity |
Not mentioned | (Zhang et al., 2021) | |
chlorahupetones G | |||||
chlorahupetones H | |||||
chlorahupetones I | |||||
1α-hydroxy-8,12-epoxyeudesma-4,7,11-triene-6,9-dione |
Hela, K562 human tumor cells | Against Hela, K562 human cells IC50 = 22.2, 21.8 μM Moderate activity |
Not mentioned | (Wu et al., 2006) | |
14-methoxy-15,16-dinor-5αH,9αH-labda-13(E),8(17)-dien-12-one | Against Hela, K562 human cells IC50 = 5.6, 5.9 μM Strong activity |
||||
shizukaol B | C8166 cells | Against C8166 cells IC50 = 0.020, 0.089, 0.047, 0.022 μM, respectively Significant activity |
Not mentioned | (Fang et al., 2011) | |
shizukaol C | |||||
shizukaol F | |||||
shizukaol H | |||||
chloranthalactone A | MDA- MB-231, MDA-MB- 468 cells | ID50 = 2.5 μM, 1 ∼ 2.5 μM, respectively Moderate activity |
Snail、Slug and p53 protein | (Gong et al., 2021) | |
chloranthalactone B | |||||
Neuroprotective activity |
chlohenriol A |
PC12 cells | Increased cell viability from 55.4 ± 3.1 % to 66.2 ± 9.8, 58.2 ± 2.8, 78.5 ± 4.8 % at 10 μM, respectively, Moderate activity |
Not mentioned |
(Chen et al., 2021c) |
chlohenriol B |
|||||
chlohenriol C | |||||
shizukanolide H | PC12 cells | EC50 = 3.3 ± 0.9 μM Strong activity |
caspase-3, Akt | (Xu et al., 2018) | |
chlogermacrone C | PC12 cells | Increased cell viability from 43.4 ± 1.3 % to 99.6 ± 8.7, 68.1 ± 4.8 at 10 μM, respectively Excellent activity |
Not mentioned | (Chen et al., 2020) | |
zederone epoxide | |||||
curzerenone | PC12 cells | Increased cell viability from 43.41 % ± 1.59 % to 62.61 % ± 5.23 %, 64.87 % ± 8.42 %, 56.06 % ± 6.65 %, 65.87 % ± 5.34 %, 60.54 % ± 3.32 %, 68.11 % ± 4.76 % at 10 μM, respectively Moderate activity |
Not mentioned |
(Chen et al., 2021a) | |
zederone | |||||
curcodione | |||||
chlorantene C | |||||
(1E,4Z)-8-hydroxy-6-oxogermacra-1(10),4,7(11)-trieno-12,8-lactone | |||||
zederone epoxide | |||||
Regulation of glucose metabolism | shizukaol D | C3H10T1/2 cells | Not mentioned | Wnt3a, β-catenin, AMP-activated protein kinase | (Hu et al., 2017) (Yun et al., 2021) |
Antimalarial activity | fortunoid A | P. falciparum strain Dd2 | IC50 = 10.2 ± 0.37 μM, 0.5 ± 0.01 μM, respectively Moderate activity |
Not mentioned | (Zhou et al., 2017b) |
fortunoid B | |||||
fortunilide A | P. falciparum strain Dd2 | IC50 = 5.2 ± 0.6, 7.2 ± 1.3, 1.1 ± 0.2 μM, respectively Excellent activity |
Not mentioned | (Zhou et al., 2017b) | |
sarglabolide J | |||||
chlorajaponilide C | |||||
trichloranoids A | P. falciparum strain Dd2 | IC50 = 2.50 ∼ 5.00, 10.0 ∼ 15.0, 1.25 ∼ 2.50 μM, respectively Moderate activity |
Not mentioned | (Zhou et al., 2021) | |
trichloranoids D | |||||
analogue | |||||
Potassium channel blocker | chlorahololides A | rat dissociated hippocampal neurons | IC50 = 10.9, 18.6 μM, respectively tetraethylammonium chloride as the positive control Strong activity |
Potassium (K + ) channels | (Yang et al., 2007b) |
chlorahololides B | |||||
chlorahololide C | rat hippocampal neurons | IC50 = 3.6 ± 10.1, 2.7 ± 0.3, 27.5 ± 5.1,57.5 ± 6.1 μM, respectively tetraethylammonium chloride as the positive control Strong activity |
delayed rectifier Kþ current (IK) | (Yang et al., 2008) | |
chlorahololide D | |||||
chlorahololide E | |||||
chlorahololide F | |||||
Hepatoprotective activity | henriols A | WB-F344 rat cells | IC50 = 0.19, 0.66, 0.09, 0.18 μM, respectively Moderate activity |
Not mentioned | (Li et al., 2008) |
henrilabdanes A | |||||
henrilabdanes B | |||||
henrilabdanes C | |||||
sarcaglaboside A | WB-F344 rat hepatic epithelial stem-like cells | Against d-galactosamine-induced toxicity Cell survival rate = 47.5 ± 5.4, 74.9 ± 9.8, 53.0 ± 7.3, 46.3 ± 4.1, 45.5 ± 1.6, 42.4 ± 4.2, 54.5 ± 3.4 μM, respectively bicyclol = 46.6 (Positive control substance) Pronounced activity |
d-Galactosamine | (Li et al., 2006) | |
sarcaglaboside B | |||||
sarcaglaboside C | |||||
sarcaglaboside D | |||||
sarcaglaboside E | |||||
Cell adhesion inhibitors | shizukaol B | THP-1 cells | MIC = 34.1 nM, 0.9 nM, 27.3 nM, respectively IC50 = 54.6, 1.2, 34.1 μM Overall good activity |
TNF-alpha | (Kwon et al., 2006) |
cycloshizukaol A | |||||
shizukaol F | |||||
Antiviral activity | shizukaol B | HIVwt, HIVRT-K103N, HIVRT-K103N | Against HIVwt, HIVRT-K103N, HIVRT-K103N EC50 = 0.22, 0.47, 0.50 μM EC50 = 0.98, 1.36, 1.00 μM EC50 = 0.11, 3.39, 4.05 μM EC50 = 0.83, 2.35, 0.86 μM respectively, Best activity |
Not mentioned | (Fang et al., 2011) |
shizukaol C | |||||
shizukaol F | |||||
shizukaol H |
Species | Local name | Parts | Distribution | Dosage forms | Traditioanal uses |
---|---|---|---|---|---|
Chloranthus multistachys | Siyexixin Dasiyedui Dasikuaiwa Sidatianwang Sidajingang Siyexixin |
Whole herb Roots |
China (Shaanxi, Jiangxi, Chongqing, Hubei, Hunan, Guangdong, Guangxi and Guizhou) | Decoction, vinum, pill, powder (taken orally); External application |
Itchy skin, bruises and injuries, whole body pain, snakebite, nameless swelling poison and fracture |
Chloranthus serratus | Siyedui Sidatianwang Sikuaiwa Zhangerxixin Siyexixin |
Whole herb Roots Stems and Leaves |
China (Jiangsu, Hubei, Hunan, Guangdong, Guangxi, Anhui, Zhejiang, Jiangxi, Sichuan and Fujian), Japan | Liniment; External application |
Bruises and injuries, rheumatism, back and leg pain, furuncle and swelling poison, poisonous snake bite, dysmenorrhea, head sores and white baldness |
Chloranthus spicatus | Zhulan Yuzilan Chalan Zhenzhulan Jizhualan Mizilan |
Whole herb Roots Leaves |
China (Yunnan, Sichuan, Guizhou, Fujian and Guangdong), Japan | Decoction, vinum(orally) ; External application |
Rheumatic pain, bruises and injuries, dermatitis and moss, strain and back pain epilepsy, insecticide, indigestion |
Chloranthus henryi | Dayejiji Sidatianwang Siyedui Siyexixin Sidatianwang |
Whole herb Roots |
China (Zhangjiang, Jiangxi, Guangdong, Chongqing, Sichuan, Guizhou, Fujian, Hubei and Shaanxi) | Decoction, vinum(orally) ; External application |
Snakebite, boils and sores, psoriasis wind-cold cough and asthma bone fracture, bruises and injuries |
Chloranthus holostegius | Sikuaiwa Siyejin Heixixin Tuxixin |
Whole herb Roots |
China (Sichuan, Guangxi, Guizhou and Yunnan) | Decoction, vinum, pill(orally) ; External application |
Paralysis, bone bruises and injuries, functional uterine bleeding, moss, rubella, furuncle, poisonous snake bite, liver wind headache, toothache |
Chloranthus fortunei | Shuijinghua Foshijiinsulan Yinxianjinsulan Sizilian Sidajingang |
Whole herb |
China (Guangxi, Shandong, Jiangsu, Anhui, Zhejiang, Taiwan, Jiangxi, Hubei, Hunan, Guangdong and Sichuan) | Decoction (orally); External application |
Rheumatism and cold paralysis, rheumatism and numbness, menstrual disorders, urticaria, bruises and injuries, wind-cold cough, canker sore and swelling poison |
Chloranthus sessilifolius | Sikuaiwa Hongmaoqi Sidatianwang |
Whole herb Roots |
China (Guangxi, Guizhou, Sichuan and Hunan) | External application | Dispersing cold and relieving cough, promoting blood circulation and relieving pain |
Chloranthus oldhamii | Dongnanjinsulan Luanbaojinsulan |
Whole herb |
China (Fujian, Taiwan and Guangdong) | Decoction, vinum(orally) ; External application |
Stomach pain, poisonous snake bite, painful traumatic bruising to the chest, oral ulceration, dysmenorrhea, bruises and injuries |
Chloranthus angustifolius | Siyexixin | Whole herb |
China (Hubei, Chonhqing and Sichuan) | Decoction (taken orally) | Dispel wind-dampness, promoting menstruation |
Chloranthus japonicus | Siyecao Sikuaiwa Siyeqi Sidatianwang Baimaoqi Jingangqi Maweiqi Guiduyou Duyaocao |
Whole herb Roots Stems Leaves |
China (Jilin, Liaoning, Hebei, Shaanxi, Shanxi, Gansu, Shandong and Hunan), Korea and Japan | Decoction, vinum(orally) ; External application |
Traumatic bruises, sores and boils, breast Knot, itchy skin, menorrhagia, snake bite |
Chloranthus elatior | Zhulan Yezhilan Xiaogeda Jiujiefeng Jiejiecha Shijiefeng |
Whole herb Leaves Branches Flowers |
China (Yunnan, Guangxi, Sichuan and Guizhou), Malaysia, Indonesia, Philippines and India | Decoction, pill, powder(orally) ; External application |
Cold and flu, epilepsy, rheumatic soup bucket, bruises and injuries, postpartum bleeding |
5.14 Antitumor activity
More and more research revealed that the genus Chloranthus exhibited strong toxicity against cancer cells. Tang et al. (2016). reported that shizukaol D (69) isolated from C. serratus could inhibit the growth of hepatocellular carcinoma cells by regulating the Wnt pathway. Many studies demonstrated that serralactones A (162) in C. serratus showed significant inhibition activity on LIM domain kinase 1 (LIMK1) by regulating the structure of the actin cytoskeleton of tumor cells in the invasion and metastasis, which may be a potential value in preventing the distant spread of cancer cells. Additionly, its IC50 values on MDA-MB-231 and MDA-MB-468 cells were 3.14 μM and 4.64 μM, respectively (Fu et al., 2018). Wang et al. (2014b) found that codonolactone (1 7 3) obtained from C. henryi exhibited potential antimetastatic properties against breast cancer cells using bioactivity-guided fractionation. Its mechanism may be associated with inhibiting the binding of Runx2 to the mmp-13 promoter through downregulation of invasion and migration of MDA-MB-231 and MDA-MB-157 cells. Zhu Huilin (Zhu et al., 2018) discovered that compound 313 in C. anhuiensis exhibited moderate cytotoxicity on MDA-MB-231, 4 T1, and HepG2 cells with an IC50 value of 39.7 μM. Besides, the compounds yinxiancaoside A (3), yinxiancaoside B (416), chloranoside A (4), pisumionoside (4 1 5) and sarcaglaboside A (2 1 8) separated from C. japonicus exhibited antagonistic effects on HepG-2, OV420 and MCF-7 cells (Kuang et al., 2008).
5.15 Antiinflammatory activity
The genus Chloranthus showed strong effect in anti-inflammatory activity, which are used to treat arthritis and bruises. Pan et al. demonstrated that the sesquiterpene dimer shizukaol B (65) exerted stronger anti-inflammatory activity in LPS-induced BV2 microglia model by modulating the JNK-AP-1 signaling pathway (Pan et al., 2017). Similarly, Wang lijun's group (Wang et al., 2014b) found that the compounds zederone epoxide (2 3 7), chloramultilide A (43), shizukaol B (65) and spicachlorantin B (72) isolated from C. henryi also showed significant anti-inflammatory effects through inhibiting the release of NO. Zhuo et al. (2017) reported that chlorajaponol B (10) identified from C. japonicus significantly inhibited lipopolysaccharide-induced NO release by RAW 264.7 cells. Furthermore, fortunilides K (1 1 6) isolated from C. multistachys whole herb showed the most significant anti-inflammatory activity in LPS-induced RAW 264.7 cell model. By comparison, the sesquiterpene lactones were significantly more active than the other sesquiterpenes (Huang et al., 2020). Besides, chlojaponilactones B (10) from C. japonicus exerted anti-inflammatory activity by inhibiting inflammatory mediators such as iNOS, TNF-α and IL-6, whose mechanism is related to the inhibition of NF-κB signaling pathway (Zhao et al., 2016). Zhang et al. (2012b) found active components shizukaol B (65) and D (69) isolated from C. serratus exhibited significant anti-inflammatory activity in LPS-induced RAW 264.7 inflammation model with IC50 values of 0.22 and 0.15 μM, respectively. Similarly, shizukaol G (67), M (1 0 2), and O (1 2 5) isolated from C. fortunei also showed strong anti-inflammatory activity with IC50 values of 1.90, 3.68, 1.95, 7.01 and 1.95 μM, respectively (Zhang et al., 2012c). Moreover, the compounds chololactones A-H (137–144) from C. holostegius roots showed moderate anti-inflammatory activity by inhibiting NO production against LPS-induced RAW 264.7 (Shen et al., 2017). Sun et al. found that the ethanolic extract of the roots of C. serratus showed the strongest anti-arthritic activity (Sun et al., 2020). In addition, TNF-α and PDE4 were also important signaling molecules involved in the inflammatory response. It was reported that sesquiterpene dimer chlojapolactone B (10) identifed from C. japonicus could exert anti-inflammatory effects by inhibiting the release of TNF-α (IC50 of 76.16 μM) (Li et al., 2019).
5.16 Antibacterial activity
In recent years, it has been confirmed that Chloranthus has antibacterial effects. Li (2011). found that ethyl acetate extracts of C. japonicus and C. multistachys showed a better antibacterial activity against Garcinia octococci. Furthermore, Xu et al. (2007) reported that chloramultilide B (71) isolated from C. spicatus showed inhibitory activity against both Candida albicans and Clostridium parvum with an MIC value of 0.068 µM through antifungal assays. Additionally, the monomeric shizukaol C (68) and F (66) obtained from C. japonicus showed more than 85 % inhibitory activity against Puccinia recondita (wheat leaf rust) and Phytophthora infestans (tomato late blight) (Kang et al., 2017). At the same time, the sesquiterpene dimers shizukaol C and F reported from C. japonicus whole herb showed good inhibitory activity against phytopathogenic fungi (MICs of 4 to 16 μM).
5.17 Neuroprotective activity
Alzheimer's disease (AD) is one of the most common chronic diseases in old age, which has become a major threat to human life and health. The search for natural active drugs from Chinese medicine to treat AD has attracted a lot of attention from researchers. Chen et al (Chen et al., 2021c). demonstrated that chlohenriol A-C (264–266) isolated from C. henryi showed significant neuroprotective activity against H2O2-induced PC12 cell injury model. Furthermore, shizukanolide H (30) isolated from C. anhuiensis exhibited significant neuroprotective activity against glutamate-induced apoptosis in PC12 cells. The active ingredients could reduce PC12 apoptosis by suppressing caspase-3 activity (Xu et al., 2018).
5.18 Antimalarial activity
In recent years, the antimalarial activity of the gens Chloranthus has also been widely studied. Zhou et al. (2017b) demonstrated that 16 lindenane-type sesquiterpenoids dimers isolated from C. fortunei showed antimalarial activity. Among which, fortunilide A (96), sarglabolide J (1 0 0) and chlorahololide D (1 0 3) showed the strongest antimalarial activity, which was comparable to the potency and selectivity index values of artemisinin. Meanwhile, fortunoid A (1 1 8) and B (1 1 9) isolated from C. fortunei also showed moderate antimalarial activity (Zhou et al., 2017a).
5.19 Anti-viral activity
It was reported that shizukaol B (65), shizukaol C (68), shizukaol F (66) and shizukaol H (70) isolated from C. japonilides exhibited anti-HIV activity. However, Fang et al. (2011). found that the compound shizukaol B showed more stronger inhibition.
5.20 Hypoglycemic activity
Few studies have been reported on the hypoglycemic activity of the genus Chloranthus. Hu et al. (2017) discovered that shizukaol D (69) isolated from C. japonicus could activate AMP-activated protein kinase and regulate glucose metabolism. In addition, chlorabietols A-C (366–368) isolated from the roots of C.oldhamii plants exhibited some complexinase inhibitory effects (Xiong et al., 2015).
5.21 Other activities
In addition, the genus Chloranthus also exert other pharmacological effects. Li et al. (2008) found that henriol A (75) and henrilabdanes A-C (334–336) isolated from C. henryi exhibited moderate hepatoprotective activity with IC50 values of 0.19, 0.66, 0.09 and 0.18 μM. Besides, the researchers reported that hexane extract of C. japonicus play a significant role in promoting adipogenesis. The extract activated the Wnt/β-catenin signaling pathway by promoting adipocyte differentiation (Yun et al., 2021). Moreover, three sesquiterpenoids shizukaol B (65), cycloshizukaol A (1 2 3) and shizukaol F (66), isolated from C. japonicus whole herb, also prevented monocyte adhesion to HUVEC by inhibiting TNF-α-stimulated cell adhesion molecule expression (Kwon et al., 2006). And it was reported that chlorahololide A (1 4 8) and B (1 3 0) identified from C. holostegius were two stronger potassium channel blockers (Yang et al., 2007b). In addition, Sun et al. conducted toxicity experiments on rat hearts by taking alcoholic extracts of C. serratus roots, stems and leaves, the results showed that the extracts of the alcoholic parts of C. serratus stems were the most cardiotoxic, followed by the alcoholic extracts of the leaves (Sun et al., 2019).
6 Development and utilization
6.1 Indoleamine 2, 3-dioxygenase 1(IDO1)
IDO1 inhibitors, as drugs with new targets and mechanisms, can be applied to the treatment of tumors, Alzheimer's disease, depression and other diseases, and are potential targets for tumor immunotherapy. It has been found that chloranthalactone A (2), chloranthalactones C-E (6–8) can be effective inhibitors of IDO1, and their inhibition rate has reached about 80 % (5 μM), so inhibition of IDO1 is expected to be a novel tumor treatment strategy (Tan, 2018a; Tan, 2018b; Tan, 2018c; Tan, 2018d; Tan, 2018e).
6.2 Antitumor drugs
In recent years, several components with antitumor activity have been reported from the genus Chloranthus. Researchers found that the application of shizukaol D (69) in the preparation of anti-liver cancer drugs, the addition of shizukaol D to cultures of liver cancer cells can significantly slow down the scratch healing and migration of liver cancer cells (Yu and Tang, 2016), and the component also has the effect of increasing the sensitivity of tumor multidrug-resistant cells to anti-tumor drugs, which can be used as a chemotherapy sensitizer (Yu and Jie, 2017). In addition, chloranthalactone C (6) can significantly inhibit the proliferation of tumor cells, such as blood, cervical, breast or pancreatic cancers. It can be developed as a new anti-tumor drug or its adjuvant component with significant tumor suppression effect (Yu et al., 2013). Yinxiancaoside A (3), yinxiancaoside B (4 1 6), and yinxiancaoside C (4 1 7) were shown to have significant anti-tumor activity in vitro, which can be used to develop into new, low-toxicity antitumor drugs from natural Chinese medicine (Kuang et al., 2010).
6.3 Others
The whole herb of C. fortunei and Chinese patent medicine snakebite detoxification tablet powder or Liushenwan can be mixed to make a kind of detoxification powder which has the function of local detoxification, dispersing blood stasis and reducing swelling. This product provides an effective treatment medicine for people working in the field after preventing poisonous insect bites, and several inventions have disclosed its preparation method (Zhang et al., 2018a; Zhang et al., 2018b). C. spicatus combined with other herbs can be made into a medicinal wine with health effects and treatment of migraine (Cheng & Cheng, 2015; Liang, 2015). In addition, C. japonicus herb of the genus Chloranthus has a very broad development prospect in the treatment of psoriasis (Mao, 2017).
7 Conclusions and discussion
Many species of the genus Chloranthus have been used in TCM or folk medicines to treat various diseases. Among which the most widely studies are C. japonicus, C. serratus, C. multistachys and C. henryi (Fig. 20.). This article updates the references of this genus for the last three decades and summarized all the compounds of genus Chloranthus. To date, 418 compounds have been reported from the genus Chloranthus, which include 383 terpenoids, 4 coumarins, 6 lignans, 2 simple phenylpropanoids, 4 flavonoids, 5 organic acids, 6 amides, and 8 other compounds. Among them, sesquiterpenes were generally considered as major bioactive ingredients in Chloranthus which exhibited various qualities. Furthermore, pharmacological studies showed that Chloranthus plants possessed a wide range of pharmacological activities, such as anti-cancer, antibacterial, antiviral, hypoglycemic anti-inflammatory and antimalarial. Regardless, there are still several aspects that need to be concerned about the further development of genus Chloranthus.

- The relative percentage of all published chemical and biological reports regarding Genus Chloranthus species.
In terms of chemical composition, sesquiterpenes are the most important active components of the genus Chloranthus (Fig. 21), which mainly distributed in C. japonicus and C. fortunei (Fig. 22). For further in-depth phytochemical scanning, Fig. 23 is performed to illustrate the type and the relative percentage of each chemical class isolated from Chloranthus species. These notifications are as the following: (1) Terpenoids are its main chemical components, mostly in the form of rings, with great structural variation. Some compounds open part of the ring structure on the original basis or form new rings on the original basis to form new compounds. In addition, the current research hot spot is the large ring structure of sesquiterpene dimer class, especially compounds shizukaol B (65), shizukaol F (66), shizukaol C (68) and chloramultilide B (71) were the most widely distributed and most frequently reported in the literature. (2): Diterpenes are the second major active constituents of the genus, in which more new bioactive monomers are continuously found. And they are mainly discovered in the C. henryi, C. oldhamii, C. sessilifolius and C. serratus, which are also the focus studying of the genus Chloranthus. (3): Fig. 23 is performed to illustrate that the chemical composition of C. japonicus is the most abundant, such as sesquiterpenes, monoterpenes, diterpenoids, C25 terpenoids, coumarins and lignans.

- The distribution of the secondary metabolites among Genus Chloranthus species.

- The relative percentage of secondary metabolites isolated from Genus Chloranthus species.

- The relative percentage of each chemical classes among different Genus Chloranthus.
As a group of plants possess multiple biological activities, the genus Chloranthus is particularly well studied in terms of pharmacological mechanisms of action (Fig. 24), which include antitumor, anti-inflammatory, hypoglycemic and antimalarial. Among them, shizukanolide C (29) and chloranthalactone A-E (2, 5, 6–8) are the main active compounds, which have varieties of pharmacology activities. Meanwhile, chlorahupetones G, isolated from C. henryi, exhibited the most potent cytotoxicity against A549 cells, even about 4 times than paclitaxel (Zhang et al., 2021). Of course, it cannot be ignored that monomeric compounds with outstanding pharmacological activities can be considered the source of new drugs with excellent therapeutic effects. Furthermore, the characteristic components of aconite-type sesquiterpenes and their dimers in the genus Chloranthus are novel, complex and variable in structure and rich in pharmacological activities, which deserve attention in the subsequent research and development.

- The pharmacological activities of different Genus Chloranthus species.
As a genus with a complete distribution and the presence of endemic species in China, the research and development were still incomplete. Only a bit species has been studied so far, therefore, a systematic and in-depth study and development of the genus Chloranthus is critical.
Author contributions
All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Funding
his work is supported by program project for Shaanxi Province (grant No 2019ZDLSF04-03-02); Subject Innovation Team of Shaanxi University of Chinese Medicine (grant number 2019-YL12) and the Natural Science Basic Research Project of Department of science and technology of Shaanxi Province (grant number: 2021JQ-744).
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