Studies on the Chemical Constituents from the Formosan Corals Rumphella antipathies and Echionmuricea sp.

• Main Authors: Hsu-Ming Chung, 鍾旭銘
• Other Authors: Ping-Jyun Sung
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/56312975102944612955

博士 === 國立中山大學 === 海洋生物科技暨資源學系研究所 === 100 === In the interest of identifying natural substances from marine invertebrates collected off the waters of Taiwan, we have searched the bioactive metabolites from the organic extracts of gorgonian corals Rumphella antipathies and Echinomuricea sp. This study had led to the isolation of thirty compounds (1–30), including nine new caryophyllane-related metabolites, rumphellaones A (1), B (2) and C (3), rumphelloic acids A (4) B (5) and C (6), rumphellolides J (7), K (8) and L (9), five new clovane-related metabolites, rumphellclovanes A (12), B (13), C (14), D (15) and E (16), two new disesquiterpenoid dimers, rumphelladimers A (24) and B (25), eight new natural products, (8R,9R)-isocaryolane-8,9-diol (10), 4β,8β-epoxycaryophyllan-5-ol (11), 9α-hydroxyclovan-2-one (17), 2β-hydroxyclovan-9-one (18), clovan-2,9-dione (19), 2β-acetoxyclovan-9α-ol (20), 9α-acetoxyclovan-2β-ol (21) and 2β,9β-dihydroxyclovane (22), along with a known compound, clovan-2β,9α-diol (23) from Rumphella antipathies. In addition, three new labdane-, halimane-, and clerodane-related metabolites, echinolids A (26), B (27) and C (28), a new sesquiterpenoid natural product, (7S,10R)-(+)-10,11-epoxycurcuphenol (29), along with a known compound, (+)-curcuphenol (30) were also found in Echinomuricea sp. The structures of metabolites 1–30 were established by spectroscopic methods and by comparison of the spectral data with those of related known compounds. The absolute configurations of clovane-type compounds were determined using a modified Mosher’s method for 23. The biosyntheses of compounds 1–5 and 12 were proposed. In the biological activity experiments, compounds 5 and 19 displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB. Compounds 24 and 27 displayed significant inhibitory effects on elastase release by human neutrophils. Compound 27 was found to exhibit inhibition against the growth of DLD-1 (human colon adenocarcinoma) and Lovo (human colorectal adenocarcinoma) tumor cells.