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Marine Drugs  2012 

Sarcocrassocolides M–O, Bioactive Cembranoids from the Dongsha Atoll Soft Coral Sarcophyton crassocaule

DOI: 10.3390/md10030617

Keywords: soft coral, Sarcophyton crassocaule, cytotoxic activity, anti-inflammatory activity

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Abstract:

Three new cembranoids, sarcocrassocolides M–O (1–3), have been isolated from the soft coral Sarcophyton crassocaule. The structures of the metabolites were determined by extensive spectroscopic analysis. Compounds 1–3 were shown to exhibit moderate cytotoxicity toward a limited panel of cancer cell lines and display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein.

References

[1]  Bishara, A.; Rudi, A.; Benayahu, Y.; Kashman, Y. Three biscembranoids and their monomeric counterpart cembranoid, a biogenetic diels-alder precursor, from the soft coral Sarcophyton elegans. J. Nat. Prod. 2007, 70, 1951–1954, doi:10.1021/np070129n.
[2]  Bensemhoun, J.; Rudi, A.; Bombarda, I.; Gaydou, E.M.; Kashman, Y.; Aknin, M. Flexusines A and B and epimukulol from the soft coral Sarcophyton flexuosum. J. Nat. Prod. 2008, 71, 1262–1264, doi:10.1021/np070691d.
[3]  Marrero, J.; Benítez, J.; Rodríguez, A.D.; Zhao, H.; Raptis, R.G. Bipinnatins K-Q, Minor cembrane-type diterpenes from the west Indian gorgonian Pseudopterogorgia kallos: Isolation, structure assignment, and evaluation of biological activities. J. Nat. Prod. 2008, 71, 381–389, doi:10.1021/np0705561.
[4]  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, 1232–1241, doi:10.1021/np0200820.
[5]  Rashid, M.A.; Gustafson, K.R.; Boyd, M.R. HIV-inhibitory cembrane derivatives from a Philippines collection of the soft coral Lobophytum species. J. Nat. Prod. 2000, 63, 531–533, doi:10.1021/np990372p.
[6]  K?nig, G.M.; Wright, A.D. New cembranoidditerpenes from the soft coral Sarcophyton ehrenbergi. J. Nat. Prod. 1998, 61, 494–496, doi:10.1021/np9704112.
[7]  Iwashima, M.; Matsumoto, Y.; Takahashi, H.; Iguchi, K. New marine cembrane-type diterpenoids from the Okinawan soft coral Clavularia koellikeri. J. Nat. Prod. 2000, 63, 1647–1652, doi:10.1021/np000309w.
[8]  Iguchi, K.; Fukaya, T.; Takahashi, H.; Watanabe, K. Stolonilactone, a novel terpenoid-related compound, isolated from the Okinawan soft coral Clavularia koellikeri. J. Org. Chem. 2004, 69, 4351–4355, doi:10.1021/jo030335+.
[9]  Su, J.-H.; Ahmed, A.F.; Sung, P.-J.; Chao, C.-H.; Kuo, Y.-H.; Sheu, J.-H. ManaarenolidesA-I, new diterpenoids from the soft coral Sinularia manaarensis. J. Nat. Prod. 2006, 69, 1134–1139, doi:10.1021/np050483q.
[10]  Lu, Y.; Huang, C.-Y.; Lin, Y.-F.; Wen, Z.-H.; Su, J.-H.; Kuo, Y.-H.; Chiang, M. Y.; Sheu, J.-H. Anti-inflammatory cembranoids from the soft corals Sinularia querciformis and Sinularia granosa. J. Nat. Prod. 2008, 71, 1754–1759, doi:10.1021/np8003563.
[11]  Ahmed, A.F.; Tai, S.-H.; Wen, Z.-H.; Su, J.-H.; Wu, Y.-C.; Hu, W.-P.; Sheu, J.-H. A C-3 methylatedisocembranoid and 10-oxocembranoids from a Formosan soft coral Sinularia grandilobata. J. Nat. Prod. 2008, 71, 946–951, doi:10.1021/np7007335.
[12]  Chen, B.-W.; Chao, C.-H.; Su, J.-H.; Huang, C.-Y.; Dai, C.-F.; Wen, Z.-H.; Sheu, J.-H. A novel symmetric sulfur-containing biscembranoid from the Formosan soft coral Sinularia flexibilis. Tetrahedron Lett. 2010, 44, 5764–5766.
[13]  Cheng, S.-Y.; Wen, Z.-H.; Wang, S.-K.; Chiou, S.-F.; Hsu, C.-H.; Dai, C.-F.; Chiang, M.Y.; Duh, C.-Y. Unprecedented hemiketalcembranolides with anti-inflammatory activity from the soft coral Lobophytum durum. J. Nat. Prod. 2009, 72, 152–155, doi:10.1021/np800686k.
[14]  Chao, C.-H.; Wen, Z.-H.; Wu, Y.-C.; Yeh, H.-C.; Sheu, J.-H. Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum. J. Nat. Prod. 2008, 71, 1819–1824, doi:10.1021/np8004584.
[15]  Huang, H.-C.; Ahmed, A.F.; Su, J.-H.; Wu, Y.-C.; Chiang, M.Y.; Sheu, J.-H. Crassocolides A–F, new cembranoids with a trans-fused lactone from the soft coral Sarcophyton crassocaule. J. Nat. Prod. 2006, 69, 1554–1559, doi:10.1021/np060182w.
[16]  Huang, H.-C.; Chao, C.-H.; Kuo, Y.-H.; Sheu, J.-H. Crassocolides G-M, cembranoids from a Formosan soft coral Sarcophyton crassocaule. Chem. Biodivers. 2009, 6, 1232–1242, doi:10.1002/cbdv.200800142.
[17]  Cheng, Y.-B.; Shen, Y.-C.; Kuo, Y.-H.; Khalil, A.T. Cembranediterpenoids from the Taiwanese soft coral Sarcophyton stolidotum. J. Nat. Prod. 2008, 71, 1141–1145, doi:10.1021/np0706668.
[18]  Cheng, S.-Y.; Wang, S.-K.; Chiou, S.-F.; Hsu, C.-H.; Dai, C.-F.; Chiang, M.Y.; Duh, C.-Y. Cembranoids from the octocoral Sarcophyton ehrenbergi. J. Nat. Prod. 2010, 73, 197–203, doi:10.1021/np900693r.
[19]  Su, J.-H.; Lu, Y.; Lin, W.-Y.; Wang, W.-H.; Sung, P.-J.; Sheu, J.-H. A cembranoid, trocheliophorol, from the cultured soft coral Sarcophyton trocheliophorum. Chem. Lett. 2010, 39, 172–173, doi:10.1246/cl.2010.172.
[20]  Wang, G.-H.; Huang, H.-C.; Su, J.-H.; Huang, C.-Y.; Hsu, C.-H.; Kuo, Y.-H.; Sheu, J.-H. Crassocolides N–P, three cembranoids from the Formosan soft coral Sarcophyton crassocaule Bioorg. Med. Chem. Lett. 2011, 21, 7201–7204.
[21]  Sheu, J.-H.; Wang, G.-H.; Duh, C.-Y.; Soong, K. Pachyclavulariolides M-R, six novel diterpenoids from a Taiwanese soft coral Pachyclavulariaviolacea. J. Nat. Prod. 2003, 66, 662–666, doi:10.1021/np020603j.
[22]  Lin, W.-Y.; Lu, Y.; Su, J.-H.; Wen, Z.-H.; Dai, C.-F.; Kuo, Y.-H.; Sheu, J.-H. Bioactive cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Mar. Drugs 2011, 9, 994–1006, doi:10.3390/md9060994.
[23]  Lin, W.-Y.; Su, J.-H.; Lu, Y.; Wen, Z.-H.; Dai, C.-F.; Kuo, Y.-H.; Sheu, J.-H. Cytotoxic and anti-inflammatory cembranoids from the Dongsha Atoll soft coral Sarcophyton crassocaule. Bioorg. Med. Chem. 2010, 18, 1936–1941.
[24]  Duh, C.-Y.; Wang, S.-K.; Chung, S.-G.; Chou, G.-C.; Dai, C.-F. Cytotoxiccembrenolides and steroids from the Formosan soft coral Sarcophyton crassocaule. J. Nat. Prod. 2000, 63, 1634–1637, doi:10.1021/np0002381.
[25]  Li, G.; Zhang, Y.; Deng, Z.; Ofwegen, L. V.; Proksch, P.; Lin, W. Cytotoxic cembranoid diterpenes from a soft coral Sinularia gibberosa. J. Nat. Prod. 2005, 68, 649–652, doi:10.1021/np040197z.
[26]  Scudiero, D.A.; Shoemaker, R.H.; Paull, K.D.; Monks, A.; Tierney, S.; Nofziger, T.H.; Currens, M.J.; Seniff, D.; Boyd, M.R. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 1988, 48, 4827–4833.
[27]  Jean, Y.-H.; Chen, W.-F.; Duh, C.-Y.; Huang, S.-Y.; Hsu, C.-H.; Lin, C.-S.; Sung, C.-S.; Chen, I.-M.; Wen, Z.-H. Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory and analgesic effects of the natural marine compound lemnalol from Formosan soft coral Lemnalia cervicorni. Eur. J. Pharmacol. 2008, 578, 323–331, doi:10.1016/j.ejphar.2007.08.048.

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