Sarcophyolides B-E, New Cembranoids from the Soft Coral Sarcophyton elegans

Marine Drugs

Volumn 11, Issue 9, 2013, Pages 3186-3196

  Xi, Zhifang ^a   Bie, Wei ^a,b   Chen, Wei ^a   Liu, Dong ^a   Van Ofwegen, Leen ^c   Proksch, Peter ^d   Lin, Wenhan ^a  

^a PEKING UNIVERSITY   (China)

^b Beijing Entry Exit Inspection and Quarantine Bureau   (China)

^c NATURALIS BIODIVERSITY CENTER   (Netherlands)

^d HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Cembranoid; Cytotoxicity; Sarcophyolide; Sarcophyton elegans; Soft coral

Indexed keywords

ANTINEOPLASTIC AGENT; CEMBRANOID; LOBOCRASOL; SARCOPHYOLIDE B; SARCOPHYOLIDE C; SARCOPHYOLIDE D; SARCOPHYOLIDE E; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARCINOMA CELL; COLON CARCINOMA; CONTROLLED STUDY; CORAL; DRUG ISOLATION; DRUG STRUCTURE; FEMALE; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; LUNG ADENOCARCINOMA; OVARY CARCINOMA; SARCOPHYTON ELEGANS; STOMACH CARCINOMA;

ALCYONACEA; SARCOPHYTON;

ANIMALS; ANTHOZOA; CELL LINE, TUMOR; DITERPENES; HUMANS;

EID: 84885081623     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11093186     Document Type: Article

References (27)

1. Roethle, P.A.; Trauner, D. The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products. Nat. Prod. Rep. 2008, 25, 298-317.
2. Iguchi, K. Yonarolide: A new marine norditerpenoid possessing a novel tricyclic skeleton, from the Okinawan soft coral of the genus, Sinularia. Tetrahedron Lett. 1995, 36, 8807-8808.
3. Anjaneyulu, A.S.R.; Rao, G.V. Chemical constituents of the soft coral species of Sarcophyton genus: A review. J. Indian Chem. Soc. 1997, 74, 272-278.
4. Kelman, D.; Kashman, Y.; Rosenberg, E.; Kushmaro, A.; Loya, Y. Antimicrobial activity of Red Sea corals. Mar. Biol. 2006, 149, 357-363.
5. Fleury, B.G.; Coll, J.C.; Sammarco, P.W.; Tentori, E.; Duquesne, S. Complementary (secondary) metabolites in an octocoral competing with a scleractinian coral: Effects of varying nutrient regimes. J. Exp. Mar. Biol. Ecol. 2004, 303, 115-131.
6. Anthoni, U.; Bock, K.; Christophersen, C; Duus, J.O.; Kjaer, E.B.; Nielsen, P.H. Structure of a novel antifouling epoxy cembrenoid diterpene from a Sarcophyton sp. Tetrahedron Lett. 1991, 32, 2825-2826.
7. Lin, W.; Su, J.; Lu, Y.; Wen, Z.; Dai, C; Kuo, Y.; Sheu, J. Cytotoxic and anti-inflammatory cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Bioorg. Med. Chem. 2010, 18, 1936-1941.
8. Zhang, C; Li, J.; Su, J.; Liang, Y.; Yang, X.; Zheng, K.; Zeng, L. Cytotoxic diterpenoids from the soft coral Sarcophyton crassocaule. J. Nat. Prod. 2006, 69, 1476-1480.
9. Duh, C; Wang, S.; Chung, S.; Chou, G.; Dai, C. Cytotoxic cembrenolides and steroids from the Formosan soft coral Sarcophyton crassocaule. J. Nat. Prod. 2000, 63, 1634-1637.
10. Sawant, S.S.; Youssef, D.T.A.; Reiland, J.; Ferniz, M.; Marchetti, D.; El Sayed, K.A. Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine. J. Nat. Prod. 2006, 69, 1010-1013.
11. Grkovic, T.; Whitson, E.L.; Rabe, D.C.; Gardella, R.S.; Bottaro, D.P.; Linehan, W.M.; McMahon, J.B.; Gustafson, K.R.; McKee, T.C. Identification and evaluation of soft coral diterpenes as inhibitors of HIF-2α induced gene expression. Bioorg. Med. Chem. Lett. 2011, 21, 2113-2115.
12. Badria, F.A.; Guirguis, A.N.; Perovic, S.; Steffen, R.; Muller, W.E.G.; Schroder, H.C. Sarcophytolide: A new neuroprotective compound from the soft coral Sarcophyton glaucum. Toxicology 1998, 131, 133-143.
13. Badria, F.A.; Guirguis, A.N.; El-Naggar, W.A. Antibacterial and antifungal agents from Egyptian marine organisms. Int. J. Pharmacol. 1997, 35, 284-287.
14. Koh, M.; Iwanaga, T.; Hatanaka, M.; Nakano, A.; Morihara, K.; Takemura, K. Distribution of sarcophytol A in soft coral of the Sarcophyton genus. Biosci. Biotechnol. Biochem. 2000, 64, 858-861.
15. Ahmed, A.F.; Kuo, Y.H.; Dai, C; Sheu, J. Oxygenated terpenoids from a Formosan soft coral Sinularia gibberosa. J. Nat. Prod. 2005, 68, 1208-1212.
16. Ren, J.; Liu, D.; Tian, L.; Wei, Y.; Proksch, P.; Zeng, J.; Lin, W. Venezuelines A-G, new phenoxazine-based alkaloids and aminophenols from Streptomyces venezuelae and the regulation of gene target Nur77. Bioorg. Med. Chem. Lett. 2013, 23, 301-304.
17. Sawant, S.S.; Sylvester, P.W.; Avery, M.A.; Desai, P.; Youssef, D.T.A.; El Sayed, K.A. Bioactive rearranged and halogenated semisynthetic derivatives of the marine natural product sarcophine. J. Nat. Prod. 2004, 67, 2017-2023.
18. Rodriguez, A.D.; Pina, I.C.; Acosta, A.L.; Ramirez, C; Soto, J.J. Synthesis of analogues of eunicea γ-cembranolides containing cyclic ethers via saponification. J. Org. Chem. 2001, 66, 648-650.
19. Osabe, K.; Kobayashi, M. Marine terpenes and terpenoids. VIII. Transannular cyclization of 3,4-epoxy-1,7,11-cembratriene systems. Chem. Pharm. Bull. 1989, 37, 1192-1196.
20. Bie, W.; Deng, Z.; Xu, M.; Lin, W. Structural elucidation of a new cembranoid diterpene from the Chinese soft coral Sarcophyton sp. J. Chin. Pharm. Sci. 2008, 17, 221-224.
21. Bernstein, J.; Shmeuli, U.; Zadock, E.; Kashman, Y.; Néeman, I. Sarcophine, a new epoxy cembranolide from marine origin. Tetrahedron 1974, 30, 2817-2824.
22. Gawronski, J.K.; Oeveren, A.; Deen, H.; Leung, C.W.; Feringa, B. Simple circular dichroic method for the determination of absolute configuration of 5-substituted 2(5H)-furanones. J. Org. Chem. 1996, 61, 1513-1515.
23. Hegazya, M.E.; El-Beih, A.A.; Moustafad, A.Y.; Hamdy, A.A.; Alhammady, M.A.; Selim, R.M.; Abdel-Rehim, M.; Paré, P.W. Cytotoxic cembranoids from the red sea soft coral Sarcophyton glaucum. Nat. Prod. Commun. 2011, 6, 1809-1812.
24. Khalid, A.E.S.; Mark, T. Structurally novel bioconversion products of the marine natural product sarcophine effectively inhibit JB6 cell transformation. J. Org. Chem. 1998, 63, 7449-7455.
25. Kobayashi, M.; Kondo, K.; Osabe, K.; Mitsuhashi, H. Marine terpenes and terpenoids. V. Oxidation of sarcophytol A, a potent anti-tumor-promoter from the soft coral Sarcophyton glaucum. Chem. Pharm. Bull. 1988, 36, 2331-2341.
26. Kobayashi, M.; Iesaka, T.; Nakano, E. Marine terpenes and terpenoids. IX. Structures of six new cembranoids, sarcophytols F, K, P, Q, R and S, from the soft coral Sarcophyton glaucum. Chem. Pharm. Bull. 1989, 37, 2053-2057.
27. Lin, S.; Wang, S.; Cheng, S.; Duh, C. Lobocrasol, a new diterpenoid from the soft coral Lobophytum crassum. Org. Lett. 2009, 11, 3012-3014.