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Chemical Diversity and Biological Activity of Secondary Metabolites from Soft Coral Genus Sinularia Since 2013

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Chemical Diversity and Biological Activity of Secondary Metabolites from Soft Coral Genus Sinularia Since 2013 Review Chemical Diversity and Biological Activity of Secondary marine drugs Metabolites from Soft Coral Genus Sinularia since 2013 Xia YanReview 1, Jing Liu 1, Xue Leng 1 and Han Ouyang 2,* Chemical Diversity and Biological Activity of Secondary Metabolites from1 Li Dak Soft Sum Yip Coral Yio Chin Kenneth Genus Li MarineSinularia Biopharmaceuticalsince Research 2013 Center, Department of Marine Pharmacy, College of Food and Pharmaceutical Sciences, Ningbo University, Xia Yan 1, Jing Liu 1, Xue LengNingbo1 and 315800 Han Ouyang, China; [email protected],* (X.Y.); [email protected] (J.L.); [email protected] (X.L.) 2 Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, China * Correspondence: [email protected]; Tel.: +86-574-87609771 1 Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharmaceutical Research Center, Department of Marine Pharmacy, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315800, China; Abstract:[email protected] Sinularia is (X.Y.);one of [email protected] the conspicuous (J.L.); soft [email protected] coral species (X.L.) widely distributed in the world’s 2 oceansInstitute at a depth of Drug of Discovery about 12 Technology, m. Secondary Ningbo University,metabolites Ningbo from 315211, the Chinagenus Sinularia show great chem- * Correspondence: [email protected]; Tel.: +86-574-87609771 ical diversity. More than 700 secondary metabolites have been reported to date, including terpe- noids,Abstract: norterpenoids,Sinularia is steroids/steroidal one of the conspicuous glycosides, soft coral and species other widely types distributed. They showed in the world’sa broad range of potentoceans biological at a depth activities. of about 12 There m. Secondary were detail metabolitesed reviews from the on genus the Sinulariaterpenoidsshow from great chemicalSinularia in 2013, anddiversity. now, it still More play thans 700a vital secondary role in metabolites the innovatio haven been of lead reported compounds to date, including for drug terpenoids, development. The structures,norterpenoids, names, steroids/steroidal and pharmacological glycosides, activities and other of types. compounds They showed isolated a broad from range the of potentgenus Sinularia frombiological 2013 to activities.March 2021 There are were summarized detailed reviews in this on thereview. terpenoids from Sinularia in 2013, and now, it still plays a vital role in the innovation of lead compounds for drug development. The structures, names, and pharmacological activities of compounds isolated from the genus Sinularia from 2013 to Keywords: soft coral; Sinularia; secondary metabolites; bioactivity March 2021 are summarized in this review. Keywords: soft coral; Sinularia; secondary metabolites; bioactivity Citation: Yan, X.; Liu, J.; Leng, X.; Ouyang, H. Chemical Diversity and 1. Introduction Biological Activity of Secondary Citation: Yan, X.; Liu, J.; Leng, X.; Metabolites from Soft Coral Genus Secondary metabolites from marine organisms represented a plentiful source of Ouyang, H. Chemical Diversity and 1. Introduction Sinularia sinceBiological 2013 Activity. Mar. Drugs of Secondary 2021, structurallySecondary diverse metabolites and natural from marine bioactive organisms products. represented The asoft plentiful corals source of ofgenus struc- Sinularia 19, x. https://Metabolitesdoi.org/10.3390/xxxxx from Soft Coral Genus (phylumturally diverseCnidaria, and class natural Anthozoa, bioactive products.subclass TheOctocorallia, soft corals of order genus Alcyonacea,Sinularia (phylum family Alcy- Sinularia since 2013. Mar. Drugs 2021, oniidae)Cnidaria, inhabiting class Anthozoa, the coral subclass reefs Octocorallia,or rocks in ordershallow Alcyonacea, water constitutes family Alcyoniidae) a dominant por- Academic19 Editor, 335. :https://doi.org/10.3390/ Marialuisa Menna tioninhabiting of the biomass the coral in reefs the tropical or rocks incoral shallow reef systems water constitutes in the world. a dominant There portion are more of than 90 md19060335 speciesthe biomass of Sinularia in the, and tropical more coral than reef 50 systems species in have the world.been chemically There are moreevaluated than 90from 1975 species of Sinularia, and more than 50 species have been chemically evaluated from 1975 Received: 20 May 2021 to 2013 [1]. As reported, Sinularia is well-known to produce a wealth of diverse and com- Academic Editor: Marialuisa Menna to 2013 [1]. As reported, Sinularia is well-known to produce a wealth of diverse and com- Accepted: 10 June 2021 plexplex secondary secondary metabolites metabolites, such, such as as sesquiterpenes sesquiterpenes (10%), (10%) diterpenes, dite (46%),rpenes norsesquiter- (46%), norsesquit- Published: 11 June 2021 Received: 20 May 2021 erpenespenes (2%),(2%) norditerpenes, norditerpenes (9%), (9%) steroids/steroidal, steroids/steroidal glycosides glycosides (22%), and other(22%) types, and (11%) other types Accepted: 10 June 2021 (11%)(Figure (Figure1)[ 1 –1)3]. [1 These–3]. These metabolites metabolites exhibit exhibit a wide rangea wide of range biological of biological activities, such activities, as such Publisher’sPublished: Note: 11MDP JuneI 2021stays neu- as cytotocytotoxic,xic, anti-inflammatory, anti-inflammatory, antifouling, antifouling and anti-microbials, and anti-microbials [4–14]. [4–14]. tral with regard to jurisdictional Publisher’s Note: claims in published maps andMDPI institu- stays neutral with regard to jurisdictional claims in 11% 10% tional affiliations. published maps and institutional affil- iations. Sesquiterpene Diterpene 22% Norsesquiterpene Copyright: © 2021 by the authors. Norditerpene Steroid/steroidal glycoside SubmittedCopyright: for possible© 2021 open by access the authors. publicationLicensee under MDPI,the terms Basel, and Switzerland. con- Others 46% ditions ofThis the Creative article is anCommons open access At- article 9% tribution (CCdistributed BY) license under (http://crea- the terms and 2% conditions of the Creative Commons tivecommons.org/licenses/by/4.0/). Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ FigureFigure 1. Compounds 1. Compounds from from genusgenusSinularia Sinulariawith with different different ratios ratio of structurals of structural types. types. 4.0/). Mar. Drugs 2021, 19, 335. https://doi.org/10.3390/md19060335 https://www.mdpi.com/journal/marinedrugs Mar. Drugs 2021, 19, x. https://doi.org/10.3390/xxxxx www.mdpi.com/journal/marinedrugs Mar. Drugs 2021, 19, 335 2 of 25 There are some published literature reviews on the genus Sinularia. For example, Liang et al. [15] reviewed the secondary metabolites obtained from Sinularia and summarized the different types of chemical structures and/or biological investigations within a literature survey from 1975 to April 2013. Chen et al. [1] reviewed the terpenes from the soft coral of the genus Sinularia, highlighting their novel chemistry and pharmacological activities. Sheu et al. [16] reviewed the structures, names, and bioactivities of 75 marine diterpenoids from octocorals possessing a hydroperoxy group, of which 41 compounds exhibited potential biomedical activities. Lakshmi et al. [17] summarized the chemical constituents of ≈40 S. sp. covering a period of 1975–2004. Rodrigues et al. [18] reviewed the new isolated cembranoid derivatives from species of genera Sarcophyton, Sinularia, and Lobophytum as well as their biological properties during 2016–2018. Especially, the current review focuses on the chemical structures and the biological activities of secondary metabolites obtained from soft coral genus S. since 2013; the Scifinder and Web of Science databases were used for research (Table1). Table 1. Chemically studied Sinularia soft coral from 2013 to March 2021. Species Sampling Locations Authors Ref. S. humilis Ximao Island, Hainan Province, China Li-Li Sun; Xu-Wen Li * [4] S. variabilis the Persian Gulf Pardis Mohammadi Pour; Mustafa Ghanadian * [19] S. scabra Pingtung, southern Taiwan Yu-Hung Lu; Mohamed El-Shazly * [20] S. polydactyla Xisha Islands, Hainan Province, China Fei Ye; Xu-wen Li * [21] S. sp. Yalong bay, Sanya, China Min Yang; Yue-Wei Guo * [22] S. depressa Ximao Island, Hainan Province, China Min Yang; Yue-Wei Guo * [5] S. polydactyla Hurghada, Egypt Mohamed A. Tammam; Vassilios Roussis * [6] S. erecta Ximao Island, Hainan Province, China Jiao Liu; Yue-Wei Guo * [2] S. erecta Ximao Island, Hainan Province, China Jiao Liu; Yue-Wei Guo * [7] S. humilis Ximao Island, Hainan Province, China Jie Li; Xu-wen Li * [23] S. scabra Xigu Island, Hainan Province, China Wan-Xiang Cui; Yue-Wei Guo * [24] S. polydactyla Ximao Island, Hainan Province, China Wan-Xiang Cui; Yue-Wei Guo * [24] S. leptoclados Pingtung, Taiwan Yu-Chia Chang; Tsong-Long Hwang * [25] S. tumulosa Ximao Island, Hainan Province, China You-Sheng Cai; Yue-Wei Guo * [8] S. scabra Grand Island, NY, USA Min Yang; Xu-wen Li * [26] S. flexibilis Xidao Island, Hainan Qihao Wu; Yue-Wei Guo * [27] S. multiflora Xisha Islands of the South China Sea Zheng Wang; Guo-Qiang Li * [28] S. flexibilis Mantanani Island, Sabah, Malaysia Chin-Soon Phan; Takashi Kamada * [29] S. hirta Yalong Bay, Hainan, China Si-Qi Lu; Guan-Ying Han * [30] S. sp. Zhanjiang, Guangdong Province, China Wei Lai; Shi-Hai Xu * [31] S. sp. Xisha Island, South China Sea, China Cheng-Shi Jiang; Yue-Wei Guo * [32] S. sp. Xisha Island, South China Sea, China Cheng-Shi Jiang; Yue-Wei Guo * [9] S. digitata Tho Chu island, Phu Quoc, Kien Giang, Vietnam Nguyen Thi Huong; Nguyen Hoai Nam *
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