Four new cembrane-type diterpenoids, sarcophyolides B–E ( 1– 4), along with 11 known analogues were isolated from the soft coral Sarcophyton elegans. The structures of new compounds 1– 4 were established on the basis of spectroscopic analysis and chemical conversion. The new cembranoids sarcophyolides B ( 1) and lobocrasol were found to exhibit potent inhibition against A2780 human ovarian tumor cells.
References
[1]
Roethle, P.A.; Trauner, D. The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products. Nat. Prod. Rep. 2008, 25, 298–317, doi:10.1039/b705660p.
[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, doi:10.1016/0040-4039(95)01867-H.
[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, doi:10.1007/s00227-005-0218-8.
[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, doi:10.1016/j.jembe.2003.11.006.
[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, doi:10.1016/0040-4039(91)85097-O.
[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, doi:10.1016/j.bmc.2010.01.036.
[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, doi:10.1021/np050499g.
[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, doi:10.1021/np0002381.
[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, doi:10.1021/np050527v.
[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, doi:10.1016/j.bmcl.2011.01.127.
[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, doi:10.1016/S0300-483X(98)00124-3.
[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, doi:10.1076/phbi.35.4.284.13307.
[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, doi:10.1271/bbb.64.858.
[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, doi:10.1021/np050114u.
[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, doi:10.1016/j.bmcl.2012.10.096.
[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, doi:10.1021/np0497393.
[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, doi:10.1021/jo001025j.
[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, doi:10.1016/S0040-4020(01)97451-4.
[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, doi:10.1021/jo951400l.
[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, doi:10.1021/jo9813134.
[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, doi:10.1248/cpb.36.2331.
[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, doi:10.1248/cpb.37.2053.
[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, doi:10.1021/ol901070e.
