Login Register Cart 0
Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Chemical Constituents and Bioactivities of Gorgonian Corals

Author(s): Hui Lei, Peng Jiang and Dan Zhang*

Volume 24, Issue 12, 2020

Page: [1315 - 1330] Pages: 16

DOI: 10.2174/1385272824999200608134516

Price: $65

Abstract

Gorgonian corals are considered as a rich source of secondary metabolites with unique structural features and biological activities. A large number of novel metabolites with potent pharmacological properties have been isolated from gorgonian corals. Some of these compounds have exhibited to possess new mechanisms of action, which hold great promises as potential lead compounds in future marine drug development. This review aims to provide an overview of chemical constituents and biological activities of gorgonian corals from 2015 to December, 2019. Some 145 metabolites, including 16 sesquiterpenoids, 62 diterpenoids, 62 steroids and 5 alkaloids were reported during this period and their pharmacological activities were investigated. Moreover, the peculiar structure and potential medicinal value of these new compounds are discussed in this review.

Keywords: Gorgonian corals, chemical constituents, bioactivity, marine natural products, secondary metabolites, peculiar structure, potential medicinal value.

« Previous Next »
Graphical Abstract

[1]
Rodríguez, A.D. The natural products chemistry of West Indian gorgonian octocorals. Tetrahedron, 1995, 51(16), 4571-4618.
[http://dx.doi.org/10.1016/0040-4020(95)00216-U] [PMID: 32287414]
[2]
Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep., 2017, 34(3), 235-294.
[http://dx.doi.org/10.1039/C6NP00124F] [PMID: 28290569]
[3]
Gutiérrez, M.; Santamaría, R.; Gómez-Reyes, J.F.; Guzmán, H.M.; Ávila-Román, J.; Motilva, V.; Talero, E. New eunicellin-type diterpenes from the panamanian octocoral Briareum asbestinum. Mar. Drugs, 2020, 18(2), 84.
[http://dx.doi.org/10.3390/md18020084] [PMID: 32012770]
[4]
Matulja, D.; Kolympadi Markovic, M.; Ambrožić, G.; Laclef, S.; Pavelić, S.K.; Marković, D. Secondary metabolites from gorgonian corals of the genus eunicella: structural characterizations, biological activities, and synthetic approaches. Molecules, 2019, 25(1), 129.
[http://dx.doi.org/10.3390/molecules25010129] [PMID: 31905691]
[5]
Blunt, J.W.; Carroll, A.R.; Copp, B.R.; Davis, R.A.; Keyzers, R.A.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep., 2018, 35(1), 8-53.
[http://dx.doi.org/10.1039/C7NP00052A] [PMID: 29335692]
[6]
Yin, F.Z.; Yang, M.; Li, S.W.; Wu, M.J.; Huan, X.J.; Miu, Z.H.; Wang, H.; Guo, Y.W. Two new hydroperoxy steroids from the South China Sea gorgonian Rumphella sp. Steroids, 2020, 155108558
[http://dx.doi.org/10.1016/j.steroids.2019.108558] [PMID: 31866544]
[7]
Carroll, A.R.; Copp, B.R.; Davis, R.A.; Keyzers, R.A.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep., 2019, 36(1), 122-173.
[http://dx.doi.org/10.1039/C8NP00092A] [PMID: 30663727]
[8]
Chung, H.M.; Wang, Y.C.; Tseng, C.C.; Chen, N.F.; Wen, Z.H.; Fang, L.S.; Hwang, T.L.; Wu, Y.C.; Sung, P.J. Natural product chemistry of gorgonian corals of genus Junceella-part III. Mar. Drugs, 2018, 16(9), 339.
[http://dx.doi.org/10.3390/md16090339] [PMID: 30227646]
[9]
Sun, J.F.; Huang, H.; Chai, X.Y.; Yang, X.W.; Meng, L.; Huang, C.G.; Zhou, X.F.; Yang, B.; Hu, J.; Chen, X.Q.; Lei, H.; Wang, L.; Liu, Y. Dichotellides A-E, five new iodine-containing briarane type diterpenoids from Dichotella gemmacea. Tetrahedron, 2011, 67, 1245-1250.
[http://dx.doi.org/10.1016/j.tet.2010.11.087]
[10]
Li, C.; La, M-P.; Li, L.; Li, X-B.; Tang, H.; Liu, B-S.; Krohn, K.; Sun, P.; Yi, Y-H.; Zhang, W. Bioactive 11,20-epoxy-3,5(16)-diene briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea. J. Nat. Prod., 2011, 74(7), 1658-1662.
[http://dx.doi.org/10.1021/np200330c] [PMID: 21721519]
[11]
Li, C.; La, M.P.; Tang, H.; Pan, W.H.; Sun, P.; Krohn, K.; Yi, Y.H.; Li, L.; Zhang, W. Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea. Bioorg. Med. Chem. Lett., 2012, 22(13), 4368-4372.
[http://dx.doi.org/10.1016/j.bmcl.2012.05.001] [PMID: 22647719]
[12]
Lei, H.; Sun, J.F.; Han, Z.; Zhou, X.F.; Yang, B.; Liu, Y.H. Fragilisinins A-L, new briarane-type diterpenoids from gorgonian Junceella fragilis. RSC Advances, 2014, 4, 5261.
[http://dx.doi.org/10.1039/c3ra46163g]
[13]
Hong, P.H.; Su, Y.D.; Lin, N.C.; Chen, Y.H.; Kuo, Y.H.; Hwang, T.L.; Wang, W.H.; Chen, J.J.; Sheu, J.H.; Sung, P-J. Briarenolide E: the first 2-ketobriarane diterpenoid from an octocoral Briareum sp. (Briareidae). Tetrahedron Lett., 2012, 53, 1710-1712.
[http://dx.doi.org/10.1016/j.tetlet.2012.01.077]
[14]
Su, Y.D.; Cheng, C.H.; Chen, W.F.; Chang, Y.C.; Chen, Y.H.; Hwang, T.L.; Wen, Z.H.; Wang, W.H.; Fang, L.S.; Chen, J.J.; Wu, Y.C.; Sheu, J.H.; Sung, P.J. Briarenolide J, the first 12-chlorobriarane diterpenoid from an octocoral Briareum sp. (Briareidae). Tetrahedron Lett., 2014, 55, 6065-6067.
[http://dx.doi.org/10.1016/j.tetlet.2014.09.032]
[15]
Gupta, P.; Sharma, U.; Schulz, T.C.; Sherrer, E.S.; McLean, A.B.; Robins, A.J.; West, L.M. Bioactive diterpenoid containing a reversible “spring-loaded” (E,Z)-dieneone Michael acceptor. Org. Lett., 2011, 13(15), 3920-3923.
[http://dx.doi.org/10.1021/ol201443k] [PMID: 21749084]
[16]
Tello, E.; Castellanos, L.; Ferro, C.A.; Duque, C. Disruption in quorum-sensing systems and bacterial biofilm inhibition by cembranoid diterpenes isolated from the octocoral Eunicea knighti. J. Nat. Prod., 2012, 75(9), 1637-1642.
[http://dx.doi.org/10.1021/np300313k] [PMID: 22905751]
[17]
Sang, V.T.; Dat, T.T.H.; Vinh, L.B.; Cuong, L.C.V.; Oanh, P.T.T.; Ha, H.; Kim, Y.H.; Anh, H.L.T.; Yang, S.Y. Coral and coral-associated microorganisms: a prolific source of potential bioactive natural products. Mar. Drugs, 2019, 17(8), 468.
[http://dx.doi.org/10.3390/md17080468] [PMID: 31405226]
[18]
Qi, S.H.; Zhang, S.; Qian, Y.Q.; Xu, H.H. Antifeedant and antifouling briaranes from the South China Sea gorgonian Junceella juncea. Chem. Nat. Compd., 2009, 45, 49-54.
[http://dx.doi.org/10.1007/s10600-009-9255-8]
[19]
Liaw, C.C.; Lin, Y.C.; Lin, Y.S.; Chen, C.H.; Hwang, T.L.; Shen, Y.C. Four new briarane diterpenoids from Taiwanese gorgonian Junceella fragilis. Mar. Drugs, 2013, 11(6), 2042-2053.
[http://dx.doi.org/10.3390/md11062042] [PMID: 23752357]
[20]
Kwan, J.C.; Donia, M.S.; Han, A.W.; Hirose, E.; Haygood, M.G.; Schmidt, E.W. Genome streamlining and chemical defense in a coral reef symbiosis. Proc. Natl. Acad. Sci. USA, 2012, 109(50), 20655-20660.
[http://dx.doi.org/10.1073/pnas.1213820109] [PMID: 23185008]
[21]
Lai, D.; Liu, D.; Deng, Z.; van Ofwegen, L.; Proksch, P.; Lin, W. Antifouling eunicellin-type diterpenoids from the gorgonian Astrogorgia sp. J. Nat. Prod., 2012, 75(9), 1595-1602.
[http://dx.doi.org/10.1021/np300404f] [PMID: 22905736]
[22]
Lei, H. Diterpenoids of gorgonian corals: chemistry and bioactivity. Chem. Biodivers., 2016, 13(4), 345-365.
[http://dx.doi.org/10.1002/cbdv.201500030] [PMID: 26919026]
[23]
Chen, M.; Han, L.; Wang, Y.; Zhang, X.L.; Wang, C.Y. A new sesquiterpene from the Hainan gorgonian Menella kanisa Grassoff. Nat. Prod. Res., 2014, 28(15), 1147-1151.
[http://dx.doi.org/10.1080/14786419.2014.918122] [PMID: 24854416]
[24]
Zheng, J.J.; Shao, C.L.; Chen, M.; Gan, L.S.; Fang, Y.C.; Wang, X.H.; Wang, C.Y. Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea. Mar. Drugs, 2014, 12(3), 1569-1579.
[http://dx.doi.org/10.3390/md12031569] [PMID: 24637960]
[25]
Chung, H.M.; Wang, W.H.; Hwang, T.L.; Chen, J.J.; Fang, L.S.; Wen, Z.H.; Wang, Y.B.; Wu, Y.C.; Sung, P.J. Rumphellols A and B, new caryophyllene sesquiterpenoids from a Formosan gorgonian coral, Rumphella antipathies. Int. J. Mol. Sci., 2014, 15(9), 15679-15688.
[http://dx.doi.org/10.3390/ijms150915679] [PMID: 25192289]
[26]
Diep, C.N.; Lyakhova, E.G.; Berdyshev, D.V.; Kalinovsky, A.I.; Tu, V.A.; Cuong, N.X.; Nam, N.H.; Minh, C.V.; Stonik, V.A. Structures and absolute stereochemistry of guaiane sesquiterpenoids from the gorgonian Menella woodin. Tetrahedron Lett., 2015, 56, 7001-7004.
[http://dx.doi.org/10.1016/j.tetlet.2015.10.102]
[27]
Yu, L.; Lin, L.; Long, B.; Chen, Y.N.; Lei, F.; Wen, L.J.; Sun, H.Y.; Gao, C.H.; Huang, R.M. Menverins H-L, new highly oxygenated guaiane lactones from the gorgonian coral Menella kanisa. Helv. Chim. Acta, 2015, 98, 710-718.
[http://dx.doi.org/10.1002/hlca.201400301]
[28]
Rodrıguez, A.D.; Boulanger, A. Americanolides A-C, new guaianolide sesquiterpenes from the Caribbean sea plume Pseudopterogorgia americana. J. Nat. Prod., 1996, 59, 653-657.
[http://dx.doi.org/10.1021/np960326e]
[29]
Rodrıguez, A.D.; Boulanger, A.; Martınez, J.R.; Huang, S.D. Sesquiterpene lactones from the caribbean sea plume Pseudopterogorgia Americana. J. Nat. Prod., 1998, 61, 451-455.
[http://dx.doi.org/10.1021/np970474k]
[30]
Zhang, W.; Guo, Y.W.; Mollo, E.; Cimino, G.; Menverins, A.D. New highly oxygenated guaiane lactones from Hainan gorgonian Menella verrucosa (Brundin). Helv. Chim. Acta, 2004, 87, 2919-2925.
[http://dx.doi.org/10.1002/hlca.200490263]
[31]
Li, L.; Wang, C.Y.; Huang, H.; Mollo, E.; Cimino, G.; Guo, Y.W. Further highly oxygenated guaiane lactones from the South China Sea gorgonian Menella sp. Helv. Chim. Acta, 2008, 91, 111-117.
[http://dx.doi.org/10.1002/hlca.200890000]
[32]
Reddy, N.S.; Reed, J.K.; Longley, R.E.; Wright, A.E. Two new cytotoxic linderazulenes from a deep-sea gorgonian of the genus Paramuricea. J. Nat. Prod., 2005, 68(2), 248-250.
[http://dx.doi.org/10.1021/np040147u] [PMID: 15730254]
[33]
Manzo, E.; Ciavatta, M.l.; Gresa, M.P.L.; Gavagnin, M.; Villani, G.; Naik, C.G.; Cimino, G. New bioactive hydrogenated linderazulene-derivatives from the gorgonian Echinogorgia complexa. Tetrahedron Lett., 2007, 48, 2569-2571.
[http://dx.doi.org/10.1016/j.tetlet.2007.02.020]
[34]
Shi, X.F.; He, W.H.; Li, G.Q. Sesquiterpenoids from gorgonian Muriceides collaris. Yao Xue Xue Bao, 2015, 50(9), 1156-1160.
[PMID: 26757553]
[35]
Bohlmann, F.; Jakupovic, J. Neue sesquiterpen-kohlenwasserstoffe mit anomalen kohlenstoffgerüst aus Silphium-arten. Phytochemistry, 1980, 19, 259-265.
[http://dx.doi.org/10.1016/S0031-9422(00)81970-6]
[36]
Huang, Q.X.; Cheng, W.; Long, H.L.; Liu, H.G.; Ofwegen, L.V.; Lin, W.H. Subergane-type sesquiterpenes from gorgonian coral Subergorgia suberosa with antibacterial activities. Helv. Chim. Acta, 2015, 98, 1202-1209.
[http://dx.doi.org/10.1002/hlca.201500086]
[37]
Groweiss, A.; Fenical, W.; He, C.h.; Clardy, J.; Wu, Z.; Yiao, Z.; Long, K. Subergorgic acid, a novel tricyclopentanoid cardiotoxin from the pacific gorgonian coral Subergorgia suberosa. Tetrahedron Lett., 1985, 26, 2379-2382.
[http://dx.doi.org/10.1016/S0040-4039(00)94832-9]
[38]
Chen, X.Q.; Xing, N.N.; Yang, B.; Zhou, X.F.; Gao, C.H.; Liu, Y.H. Two novel sesquiterpenes and a new pregnane derivative from the South China Sea gorgonian Subergorgia suberosa. Rec. Nat. Prod., 2019, 14(1), 57-64.
[http://dx.doi.org/10.25135/rnp.137.19.04.1257]
[39]
Peng, Q.; Liu, F.; Sun, H.; Liao, X.J.; Feng, M.R.; Liu, T.T.; Xu, Z.X.; Zhang, J.; Xu, S.H. A new sesquiterpene from the gorgonian coral Menella sp. Nat. Prod. Res., 2016, 30(20), 2299-2304.
[http://dx.doi.org/10.1080/14786419.2016.1166496] [PMID: 27043226]
[40]
Patiño Cano, L.P.; Quintana Manfredi, R.; Pérez, M.; García, M.; Blustein, G.; Cordeiro, R.; Pérez, C.D.; Schejter, L.; Palermo, J.A. Isolation and antifouling activity of azulene derivatives from the antarctic gorgonian Acanthogorgia laxa. Chem. Biodivers., 2018, 15(1), 1-8.
[http://dx.doi.org/10.1002/cbdv.201700425] [PMID: 29092092]
[41]
Kapustina, I.I.; Kalinovskii, A.I.; Dmitrenok, P.S.; Kuzmich, A.S.; Grebnev, B.B. Sesquiterpenoids from a vietnamese gorgonian Eunicea sp. Chem. Nat. Compd., 2016, 52, 534-535.
[http://dx.doi.org/10.1007/s10600-016-1701-9]
[42]
Li, P.; Liu, X.; Zhu, H.; Tang, X.; Shi, X.; Liu, Y.; Li, G. Unusual inner-salt guaiazulene alkaloids and bis-sesquiterpene from the South China Sea gorgonian Muriceides collaris. Sci. Rep., 2017, 7(1), 7697.
[http://dx.doi.org/10.1038/s41598-017-08100-z] [PMID: 28794492]
[43]
Sun, J.F.; Han, Z.; Zhou, X.F.; Yang, B.; Lin, X.; Liu, J.; Peng, Y.; Yang, X.W.; Liu, Y. Antifouling briarane type diterpenoids from South China Sea gorgonians Dichotella gemmacea. Tetrahedron, 2013, 69, 871.
[http://dx.doi.org/10.1016/j.tet.2012.10.102]
[44]
Zhou, W. Li, J.; e, H.C.; Liu, B.S.; Tang, H.; Gerwick, W.H.; Hua, H.M.; Zhang, W. Briarane diterpenes from the South China Sea gorgonian coral, Junceella gemmacea. Mar. Drugs, 2014, 12(2), 589-600.
[http://dx.doi.org/10.3390/md12020589] [PMID: 24473165]
[45]
Sung, P-J.; Lin, M.R.; Hwang, T.L.; Fan, T.Y.; Su, W.C.; Ho, C.C.; Fang, L.S.; Wang, W.H. Briaexcavatins M-P, four new briarane-related diterpenoids from cultured octocoral Briareum excavatum (Briareidae). Chem. Pharm. Bull. (Tokyo), 2008, 56(7), 930-935.
[http://dx.doi.org/10.1248/cpb.56.930] [PMID: 18591804]
[46]
Sung, P.J.; Su, Y.D.; Li, G.Y.; Chiang, M.Y.; Lin, M.R.; Huang, I.C.; Li, J.J.; Fang, L.S.; Wang, W.H. Excavatoids A-D, new polyoxygenated briaranes from the octocoral Briareum excavatum. Tetrahedron, 2009, 65, 6918-6924.
[http://dx.doi.org/10.1016/j.tet.2009.06.064]
[47]
Su, J.H.; Chen, B.Y.; Hwang, T.L.; Chen, Y.H.; Huang, I.C.; Lin, M.R.; Chen, J.J.; Fang, L.S.; Wang, W.H.; Li, J.J.; Sheu, J.H.; Sung, P.J. Excavatoids L-N, new 12-hydroxybriaranes from the cultured octocoral Briareum excavatum (Briareidae). Chem. Pharm. Bull. (Tokyo), 2010, 58(5), 662-665.
[http://dx.doi.org/10.1248/cpb.58.662] [PMID: 20460793]
[48]
Marchbank, D.H.; Berrue, F.; Kerr, R.G. Eunicidiol, an anti-inflammatory dilophol diterpene from Eunicea fusca. J. Nat. Prod., 2012, 75(7), 1289-1293.
[http://dx.doi.org/10.1021/np300149y] [PMID: 22734800]
[49]
Ishigami, S.T.; Goto, Y.; Inoue, N.; Kawazu, S.; Matsumoto, Y.; Imahara, Y.; Tarumi, M.; Nakai, H.; Fusetani, N.; Nakao, Y. Cristaxenicin A, an antiprotozoal xenicane diterpenoid from the deep sea gorgonian Acanthoprimnoa cristata. J. Org. Chem., 2012, 77(23), 10962-10966.
[http://dx.doi.org/10.1021/jo302109g] [PMID: 23057655]
[50]
Sung, P.J.; Lin, M.R.; Su, Y.D.; Chiang, M.Y.; Hu, W.P.; Su, J.H.; Cheng, M.C.; Hwang, T.L.; Sheu, J.H. New briaranes from the octocorals Briareum excavatum (Briareidae) and Junceella fragilis (Ellisellidae). Tetrahedron, 2008, 64, 2596-2604.
[http://dx.doi.org/10.1016/j.tet.2008.01.023]
[51]
Sung, P.J.; Su, J.H.; Wang, W.H.; Sheu, J.H.; Fang, L.S.; Wu, Y.C.; Chen, Y.H.; Chung, H.M.; Su, Y.D.; Chang, Y.C. Survey of briarane-type diterpenoids - Part IV. Heterocycles, 2011, 83, 1241-1258.
[http://dx.doi.org/10.3987/REV-11-695]
[52]
Burks, J.E.; van der Helm, D.; Chang, C.Y.; Ciereszko, L.S. The crystal and molecular structure of briarein A, a diterpenoid from the gorgonian Briareum abestinum. Acta Crystallogr., 1977, B33, 704-709.
[http://dx.doi.org/10.1107/S0567740877004518]
[53]
Su, Y.D.; Su, J.H.; Hwang, T.L.; Wen, Z.H.; Sheu, J.H.; Wu, Y.C.; Sung, P.J. Briarane diterpenoids isolated from octocorals between 2014 and 2016. Mar. Drugs, 2017, 15(2), 44.
[http://dx.doi.org/10.3390/md15020044] [PMID: 28218675]
[54]
Zheng, L.G.; Chang, Y.C.; Hu, C.C.; Wen, Z.H.; Wu, Y.C.; Sung, P.J. Fragilides K and L, new briaranes from the gorgonian coral Junceella fragilis. Molecules, 2018, 23(7), 1510.
[http://dx.doi.org/10.3390/molecules23071510] [PMID: 29932137]
[55]
Lin, C.C.; Chen, W.F.; Lee, G.H.; Wen, Z.H.; Fang, L.S.; Kuo, Y.H.; Lee, C.Y.; Sung, P.J. Fragilides M-O, new triacetoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae). Heterocycles, 2019, 98, 1-10.
[56]
Lin, C.C.; Su, J.H.; Chen, W.F.; Wen, Z.H.; Peng, B.R.; Huang, L.C.; Hwang, T.L.; Sung, P.J. New 11,20-epoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae). Molecules, 2019, 24(13), 2487.
[http://dx.doi.org/10.3390/molecules24132487] [PMID: 31284657]
[57]
Chen, Y.Y.; Fang, L.S.; Chen, Y.H.; Peng, B.R.; Su, T.P.; Huynh, T.H.; Lin, F.Y.; Hu, C.C.; Lin, N.C.; Wen, Z.H.; Chen, J.J.; Lee, C.Y.; Wang, J.W.; Sung, P.J. New 8-hydroxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae). Mar. Drugs, 2019, 17(9), 534.
[http://dx.doi.org/10.3390/md17090534] [PMID: 31540107]
[58]
Su, T.P.; Yuan, C.H.; Jhu, Y.M.; Peng, B.R.; Wen, Z.H.; Wu, Y.J.; Wu, T.Y.; Liu, H.W.; Sung, P.J. Fragilides U-W: new 11,20-epoxybriaranes from the sea whip gorgonian coral Junceella fragilis. Mar. Drugs, 2019, 17(12), 706.
[http://dx.doi.org/10.3390/md17120706] [PMID: 31847481]
[59]
Thi, N.N.; Hong, H.T.T.; Van, T.N.; Xuan, C.N.; Hoai, N.N.; Cong, T.D.; Van, K.P.; Van, M.C. Briarane-type diterpenoids from the vietnamese gorgonian Junceella fragilis. Nat. Prod. Res., 2020, 34, 385-389.
[http://dx.doi.org/10.1080/14786419.2018.1534850]
[60]
Cheng, W.; Li, X.; Yin, F.; van Ofwegen, L.; Lin, W. Halogenated briarane diterpenes with acetyl migration from the gorgonian coral Junceella fragilis. Chem. Biodivers., 2017, 14(5), 1-8.
[http://dx.doi.org/10.1002/cbdv.201700053] [PMID: 28337842]
[61]
Cheng, W.; Ji, M.; Li, X.D.; Ren, J.W.; Yin, F.L.; Ofwegen, L.V.; Yu, S.W.; Chen, X.G.; Lin, W.H. Fragilolides A-Q, norditerpenoid and briarane diterpenoids from the gorgonian coral Junceella fragilis. Tetrahedron, 2017, 73(17), 2518-2528.
[http://dx.doi.org/10.1016/j.tet.2017.03.037]
[62]
Su, Y.D.; Wen, Z.H.; Wu, Y.C.; Fang, L.S.; Chen, Y.H.; Chang, Y.C.; Sheu, J.H.; Sung, P.J. Briarenolides M-T, new briarane diterpenoids from a Formosan octocoral Briareum sp. Tetrahedron, 2016, 72, 944-951.
[http://dx.doi.org/10.1016/j.tet.2015.12.058]
[63]
Su, Y.D.; Sung, C.S.; Wen, Z.H.; Chen, Y.H.; Chang, Y.C.; Chen, J.J.; Fang, L.S.; Wu, Y.C.; Sheu, J.H.; Sung, P.J. New 9-hydroxybriarane diterpenoids from a gorgonian coral Briareum sp. (Briareidae). Int. J. Mol. Sci., 2016, 17(1), 79.
[http://dx.doi.org/10.3390/ijms17010079] [PMID: 26761004]
[64]
Li, C.; La, M.P.; Tang, H.; Sun, P.; Liu, B.S.; Zhuang, C.L.; Yi, Y.H.; Zhang, W. Chemistry and bioactivity of briaranes from the South China Sea gorgonian Dichotella gemmacea. Mar. Drugs, 2016, 14(11), 201.
[http://dx.doi.org/10.3390/md14110201] [PMID: 27801821]
[65]
Yang, B.; Zhou, X.F.; Lin, X.P.; Liu, J.; Peng, Y.; Yang, X.W.; Liu, Y.H. Cembrane diterpenes chemistry and biological properties. Curr. Org. Chem., 2012, 16, 1512-1539.
[http://dx.doi.org/10.2174/138527212800672583]
[66]
Mendoza, D.T. González, Y.; Reyes, J.F.G.; Guzmán, H.M.; Perez, J.L.L.; Gerwick, W.H.; Fernandez, P.L.; Gutiérrez, M.; Uprolides, N. O and P from the panamanian octocoral Eunicea succinea. Molecules, 2016, 21(6), 819.
[http://dx.doi.org/10.3390/molecules21060819] [PMID: 27338338]
[67]
Shi, Y.P.; Rodríguez, A.D.; Barnes, C.L.; Sánchez, J.A.; Raptis, R.G.; Baran, P. New terpenoid constituents from Eunicea pinta. J. Nat. Prod., 2002, 65(9), 1232-1241.
[http://dx.doi.org/10.1021/np0200820] [PMID: 12350138]
[68]
Shi, Y-P.; Wei, X.M.; Rodríguez, I.I.; Rodríguez, A.D.; Mayer, A.M.S. New terpenoid constituents of the Southwestern Caribbean Sea whip Pseudopterogorgia elisabethae (Bayer), including a unique pentanorditerpene. Eur. J. Org. Chem., 2009, 493-502.
[http://dx.doi.org/10.1002/ejoc.200800795]
[69]
Cao, F.; Shao, C.L.; Liu, Y.F.; Zhu, H.J.; Wang, C.Y. Cytotoxic serrulatane-type diterpenoids from the gorgonian Euplexaura sp. and their absolute confgurations by vibrational circular dichroism. Sci. Rep., 2017, 7, 1-8.
[http://dx.doi.org/10.1038/s41598-017-12841-2]
[70]
Chen, D.W.; Liu, D.; Shen, S.; Cheng, W.; Lin, W.H. Terpenoids from a Chinese gorgonian Anthogorgia sp. and their antifouling activities. Chin. J. Chem., 2012, 30, 1459-1463.
[http://dx.doi.org/10.1002/cjoc.201200412]
[71]
Cóbar, O.M. Survey of 2,11-cyclized cembranoids from Caribbean sources. Nat. Prod. Res., 2009, 23(1), 26-43.
[http://dx.doi.org/10.1080/14786410701760797] [PMID: 19140070]
[72]
Zhang, X.W.; Tang, X.L.; Yuan, H.R.; Feng, D.Q.; Su, P.; Li, P.L.; Li, G.Q. Two new eunicellin diterpenoids from the South China Sea gorgonian Muricella sibogae and their bioactivities. Nat. Prod. Res., 2015, 29(21), 2018-2023.
[http://dx.doi.org/10.1080/14786419.2015.1027893] [PMID: 25836046]
[73]
Zhao, C.; Wang, J.; Jin, D.J.; Duan, H.Q.; Xing, G.S.; Tang, S.A. Two new eunicellin diterpenoids from the East China Sea gorgonian Muricella sp. J. Asian Nat. Prod. Res., 2016, 18(9), 848-853.
[http://dx.doi.org/10.1080/10286020.2016.1164143] [PMID: 27004724]
[74]
Cheng, Y.; Ahmed, A.F.; Orfali, R.S.; Dai, C.F.; Sheu, J.H.; Briarenones, A-C. new briarellin diterpenoids from the gorgonian Briareum violaceum. Mar. Drugs, 2019, 17(2), 120.
[http://dx.doi.org/10.3390/md17020120] [PMID: 30781569]
[75]
Zhang, J.; Liang, Y.; Wang, K.L.; Liao, X.J.; Deng, Z.; Xu, S.H. Antifouling steroids from the South China Sea gorgonian coral Subergorgia suberosa. Steroids, 2014, 79, 1-6.
[http://dx.doi.org/10.1016/j.steroids.2013.10.007] [PMID: 24184487]
[76]
Chao, C.H.; Huang, L.F.; Yang, Y.L.; Su, J.H.; Wang, G.H.; Chiang, M.Y.; Wu, Y.C.; Dai, C.F.; Sheu, J.H. Polyoxygenated steroids from the gorgonian Isis hippuris. J. Nat. Prod., 2005, 68(6), 880-885.
[http://dx.doi.org/10.1021/np050033y] [PMID: 15974612]
[77]
Liu, M.; Shao, C.L.; Chen, M.; Qi, J.; Wang, Y.; Fang, Y.C.; Wang, C.Y. Bioactive 9,11-secosteroids from Gorgonian Subergorgia suberosa collected from the South China sea. Chem. Biodivers., 2014, 11(7), 1109-1120.
[http://dx.doi.org/10.1002/cbdv.201400021] [PMID: 25044596]
[78]
Cao, F.; Liu, H.Y.; Zhao, J.; Fang, Y.C.; Wang, C.Y. New 19-oxygenated steroid from the South China Sea gorgonian Dichotella gemmacea. Nat. Prod. Res., 2015, 29(2), 169-173.
[http://dx.doi.org/10.1080/14786419.2014.971321] [PMID: 25350498]
[79]
Sun, X.P.; Cao, F.; Shao, C.L.; Wang, M.; Zhang, X.L.; Wang, C.Y. Antibacterial Δ(1) -3-ketosteroids from the South China Sea gorgonian coral Subergorgia rubra. Chem. Biodivers., 2015, 12(7), 1068-1074.
[http://dx.doi.org/10.1002/cbdv.201400217] [PMID: 26172327]
[80]
Chen, M.; Han, L.; Zhang, X.L.; Wang, C.Y. Cytotoxic 19-oxygenated steroids from the South China Sea gorgonian, Pacifigorgia senta. Nat. Prod. Res., 2016, 30, 1431-1435.
[http://dx.doi.org/10.1080/14786419.2015.1063055] [PMID: 26230370]
[81]
Chang, Y.C.; Hwang, T.L.; Chao, C.H.; Sung, P.J. New marine sterols from a gorgonian Pinnigorgia sp. Molecules, 2017, 22(3), 393.
[http://dx.doi.org/10.3390/molecules22030393] [PMID: 28273821]
[82]
Subrahmanyam, C.; Kumar, S.R. A new polyoxygenated steroid from the gorgonian gorgonella umbraculum. J. Chem. Res., 2000, 2000(4), 182-183.
[http://dx.doi.org/10.3184/030823400103166878]
[83]
Nam, N.H.; Ngoc, N.T.; Hanh, T.T.H.; Cuong, N.X.; Thanh, N.V.; Thao, D.T.; Thung, D.C.; Kiem, P.V.; Minh, C.V. Cytotoxic steroids from the Vietnamese gorgonian Verrucella corona. Steroids, 2018, 138, 57-63.
[http://dx.doi.org/10.1016/j.steroids.2018.06.006] [PMID: 30018002]
[84]
Sun, L.L.; Shao, C.L.; Mei, W.L.; Huang, H.; Wang, C.Y.; Dai, H.F. Chemical constituents of gorgonian Verrucella umbraculum from the South China Sea. Biochem. Syst. Ecol., 2010, 38, 1085-1087.
[http://dx.doi.org/10.1016/j.bse.2010.11.001]
[85]
Anjaneyulu, A.S.R.; Rao, V.L.; Sastry, V.G. A new spiroketal steroid from Gorgonella umbraculum. Nat. Prod. Res., 2003, 17(3), 149-152.
[http://dx.doi.org/10.1080/14786410310000104091] [PMID: 12737396]
[86]
Zhang, W.; Guo, Y.W.; Gavagnin, M.; Mollo, E.; Cimion, G. Suberoretisteroids A-E, five new uncommon polyoxygenated steroid 24-ketals from the Hainan gorgonian Suberogorgia reticulate. Helv. Chim. Acta, 2005, 88, 87-94.
[http://dx.doi.org/10.1002/hlca.200490299]
[87]
Sica, D.; Musumeci, D. Secosteroids of marine origin. Steroids, 2004, 69(11-12), 743-756.
[http://dx.doi.org/10.1016/j.steroids.2004.09.001] [PMID: 15579326]
[88]
Sala, G.D.; Izzo, I.; Riccardis, F.D.; Sodano, G. Synthesis of calicoferol E and astrogorgiadiol, two marine 9, 10-secosteroids. Tetrahedron Lett., 1998, 39, 4741-4744.
[http://dx.doi.org/10.1016/S0040-4039(98)00932-0]
[89]
Fusetani, N.; Nagata, H.; Hirota, H.; Tsuyuki, T. Astrogorgiadiol and astrogorgin, inhibitors of cell division in fertilized starfish eggs, from a gorgonian Astrogorgia sp. Tetrahedron Lett., 1989, 30, 7079-7082.
[http://dx.doi.org/10.1016/S0040-4039(01)93428-8]
[90]
Sun, X.P.; Cao, F.; Shao, C.L.; Chen, M.; Liu, H.J.; Zheng, C.J.; Wang, C.Y. Subergorgiaols A-L, 9,10-secosteroids from the South China Sea gorgonian Subergorgia rubra. Steroids, 2015, 94, 7-14.
[http://dx.doi.org/10.1016/j.steroids.2014.12.001] [PMID: 25528195]
[91]
Mahato, S.B.; Banerjee, S.; Podder, S. Steroid transformations by microorganisms-III. Phytochemistry, 1989, 28, 7-40.
[http://dx.doi.org/10.1016/0031-9422(89)85002-2]
[92]
Li, T.T.; Tang, X.L.; Chen, C.L.; Zhang, X.W.; Wu, R.C.; Zhu, H.Y.; Li, P.L.; Li, G.Q. New eunicellin diterpenes and 9,10-secosteroids from the Gorgonian Muricella sibogae. Helv. Chim. Acta, 2013, 96, 1-6.
[http://dx.doi.org/10.1002/hlca.201200489]
[93]
Seo, Y.; Shin, J.; Song, J.I. New secosteroids from an undescribed gorgonian of the genus Muricella. J. Nat. Prod., 1995, 58(8), 1291-1295.
[http://dx.doi.org/10.1021/np50122a024] [PMID: 7595595]
[94]
Zhou, Y.M.; Chen, M.; Fu, X.M.; Fang, Y.C.; Wang, C.Y. Two new eunicellin-based diterpenoids from the South China Sea gorgonian Muricella sibogae Nutting. Nat. Prod. Res., 2014, 28(15), 1176-1181.
[http://dx.doi.org/10.1080/14786419.2014.923423] [PMID: 24896373]
[95]
Costa, S.; Giovannini, P.P.; Fantin, G.; Medici, A.; Pedrini, P. New 9,10-Secosteroids from biotransformations of bile acids with Rhodococcus ruber. Helv. Chim. Acta, 2013, 96, 2124-2133.
[http://dx.doi.org/10.1002/hlca.201300114]
[96]
Lai, D.; Yu, S.; van Ofwegen, L.; Totzke, F.; Proksch, P.; Lin, W. 9,10-secosteroids, protein kinase inhibitors from the Chinese gorgonian Astrogorgia sp. Bioorg. Med. Chem., 2011, 19(22), 6873-6880.
[http://dx.doi.org/10.1016/j.bmc.2011.09.028] [PMID: 21982797]
[97]
Naz, S.; Kerra, R.G.; Narayananb, R. New antiproliferative epoxysecosterols from Pseudopterogorgia americana. Tetrahedron Lett., 2000, 41, 6035-6040.
[http://dx.doi.org/10.1016/S0040-4039(00)01015-7]
[98]
Miller, S.L.; Tinto, W.F.; Yang, J.P.; Mclean, S.; Reynolds, W.F. 9,11-Seco-24-hydroxydinosterol from Pseudopterogorigia americana. Tetrahedron Lett., 1995, 36, 1227-1228.
[http://dx.doi.org/10.1016/0040-4039(95)00040-J]
[99]
Enwall, E.L.; Helm, D.V.D.; Hsu, I.N.; Pattabhiraman, T.; Schmitz, F.J.; Spraggins, R.L.; Weinheime, A.J. Crystal structure and absolute configuration of two cyclopropane containing marine steroids. J. Chem. Soc. Chem. Commun., 1972, 4, 215-216.
[http://dx.doi.org/10.1039/c39720000215]
[100]
He, Y.Q.; Lee Caplan, S.; Scesa, P.; West, L.M. Cyclized 9,11-secosterol enol-ethers from the gorgonian Pseudopterogorgia americana. Steroids, 2017, 125, 47-53.
[http://dx.doi.org/10.1016/j.steroids.2017.06.008] [PMID: 28648587]
[101]
Zhang, J.; Liu, L.L.; Zhong, B.L.; Liao, X.J.; Xu, S.H. 9,11-Secosteroids with cytotoxic activity from the South China Sea gorgonian coral Subergorgia suberosa. Steroids, 2015, 98, 100-106.
[http://dx.doi.org/10.1016/j.steroids.2015.03.004] [PMID: 25796549]
[102]
Chang, Y.C.; Kuo, L.M.; Su, J.H.; Hwang, T.L.; Kuo, Y.H.; Lin, C.S.; Wu, Y.C.; Sheu, J.H.; Sung, P.J. Pinnigorgiols A-C, 9,11-secosterols with a rare ring arrangement from a gorgonian coral Pinnigorgia sp. Tetrahedron, 2016, 72, 999-1004.
[http://dx.doi.org/10.1016/j.tet.2015.12.072]
[103]
Chang, Y.C.; Hwang, T.L.; Sheu, J.H.; Wu, Y.C.; Sung, P.J. New anti-inflammatory 9, 11-secosterols with a rare tricycle [5,2,1,1] decane ring from a formosan gorgonian Pinnigorgia sp. Mar. Drugs, 2016, 14, 218.
[http://dx.doi.org/10.3390/md14120218]
[104]
Kawamura, A.; Kita, M.; Kigoshi, H. Aplysiasecosterol A: a 9, 11-secosteroid with an unprecedented tricyclicγ-diketone structure from the sea hare Aplysia kurodai. Angew. Chem. Int. Ed. Engl., 2015, 54(24), 7073-7076.
[http://dx.doi.org/10.1002/anie.201501749] [PMID: 25925956]
[105]
Chang, Y.C.; Kuo, L.M.; Hwang, T.L.; Yeh, J.; Wen, Z.H.; Fang, L.S.; Wu, Y.C.; Lin, C.S.; Sheu, J.H.; Sung, P.J. Pinnisterols A-C, new 9,11-secosterols from a gorgonian Pinnigorgia sp. Mar. Drugs, 2016, 14(1), 12.
[http://dx.doi.org/10.3390/md14010012] [PMID: 26751457]
[106]
Chang, Y.C.; Hwang, T.L.; Kuo, L.M.; Sung, P.J. Pinnisterols D-J, new 11-acetoxy-9,11-secosterols with a 1,4-quinone moiety from formosan gorgonian coral Pinnigorgia sp. (Gorgoniidae). Mar. Drugs, 2017, 15(1), 11.
[http://dx.doi.org/10.3390/md15010011] [PMID: 28067822]
[107]
Yang, I.; Choi, H.; Won, D.H.; Nam, S.J.; Kang, H. An antibacterial 9, 11-secosterol from a marine sponge Ircinia sp. Bull. Korean Chem. Soc., 2014, 35(11), 3360-3362.
[http://dx.doi.org/10.5012/bkcs.2014.35.11.3360]
[108]
Mahato, S.B.; Ganguly, A.N.; Sahu, N.P. Steroid saponins. Phytochemistry, 1982, 21, 959-978.
[http://dx.doi.org/10.1016/S0031-9422(00)82400-0]
[109]
Ivanchina, N.V.; Kicha, A.A.; Stonik, V.A. Steroid glycosides from marine organisms. Steroids, 2011, 76(5), 425-454.
[http://dx.doi.org/10.1016/j.steroids.2010.12.011] [PMID: 21194537]
[110]
Lu, Y.N.; Cui, P.; Tian, X.Q.; Lou, L.G.; Fan, C.Q. Unusual cytotoxic steroidal saponins from the gorgonian Astrogorgia dumbea. Planta Med., 2016, 82(9-10), 882-887.
[http://dx.doi.org/10.1055/s-0042-106168] [PMID: 27352300]
[111]
Cheng, W.; Ren, J.W.; Huang, Q.X.; Long, H.L.; Jin, H.W.; Zhang, L.R.; Liu, H.G. Pregnane steroids from a gorgonian coral Subergorgia suberosa with anti-flu virus effects. Steroids, 2016, 108, 99-104.
[http://dx.doi.org/10.1016/j.steroids.2016.02.003] [PMID: 26853156]
[112]
Liu, F.; Li, S.; Ju, Z.R.; Liu, T.T.; Liang, R.Y.; Liao, X.J.; Xu, S.H.N.N. -(3-aminopropyl)subergorgamide, a new alkaloid from the gorgonian Paraplexaura sp. J. Asian Nat. Prod. Res., 2015, 17(8), 851-855.
[http://dx.doi.org/10.1080/10286020.2015.1009049] [PMID: 25732799]
[113]
Yang, H.; Yu, L.; Li, F.; Yi, X.X.; Li, J.Y.; Gao, C.H. A new antifouling naphthalene derivative form gorgonian coral Menella kanisa. Chem. Nat. Compd., 2018, 54(2), 368-369.
[http://dx.doi.org/10.1007/s10600-018-2349-4]
[114]
Chang, Y.C.; Sheu, J.H.; Wu, Y.C.; Sung, P.J. Terpenoids from octocorals of the genus Pachyclavularia. Mar. Drugs, 2017, 15(12), 382.
[http://dx.doi.org/10.3390/md15120382] [PMID: 29206207]
[115]
Sheu, J.H.; Chen, Y.H.; Chen, Y.H.; Su, Y.D.; Chang, Y.C.; Su, J.H.; Weng, C.F.; Lee, C.H.; Fang, L.S.; Wang, W.H.; Wen, Z.H.; Wu, Y.C.; Sung, P.J. Briarane diterpenoids isolated from gorgonian corals between 2011 and 2013. Mar. Drugs, 2014, 12(4), 2164-2181.
[http://dx.doi.org/10.3390/md12042164] [PMID: 24727390]
[116]
Qi, S.H. Bioactive compounds from marine gorgonian corals. Stud. Nat. Prod. Chem., 2012, 38, 325-351.
[http://dx.doi.org/10.1016/B978-0-444-59530-0.00012-5]
[117]
Berrue, F.; Kerr, R.G. Diterpenes from gorgonian corals. Nat. Prod. Rep., 2009, 26(5), 681-710.
[http://dx.doi.org/10.1039/b821918b] [PMID: 19387501]
[118]
Chang, J.Y.; Liaw, C.C.; Fazary, A.E.; Hwang, T.L.; Shen, Y.C. New Briarane diterpenoids from the gorgonian coral Junceella juncea. Mar. Drugs, 2012, 10(6), 1321-1330.
[http://dx.doi.org/10.3390/md10061321] [PMID: 22822375]
[119]
Zhang, Y.Y.; Liu, J.H.; Shi, D.Y.; Zheng, L. Halogenated compounds from corals: chemical diversity and biological activities. Mini Rev. Med. Chem., 2019, 19(15), 1204-1218.
[http://dx.doi.org/10.2174/1389557518666181113124015]
[120]
Wang, K.W. Terpenoids form the sea: chemical diversity and bioactivity. Curr. Org. Chem., 2014, 18, 840-866.
[http://dx.doi.org/10.2174/138527281807140515150806]

Rights & Permissions Print Cite
Article Metrics
24
© 2024 Bentham Science Publishers | Privacy Policy