Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum.
Five new cembranoids, namely, crassumolides A and B and D-F (1 and 2 and 4-6), along with four known metabolites, 7-10, were isolated from the soft coral Lobophytum crassum. Crassumolide C (3) was isolated for the first time from a natural source. The structures of these compounds were elucidated by extensive spectroscopic analysis and comparison of the NMR data with those of known analogues. The absolute stereochemistry of 1 was determined using the modified Mosher's method. Chemical transformation of 7 into the corresponding methyl ester 3 revealed the absolute stereochemistry of 3. Compounds 1, 3, and 7 were cytotoxic toward Ca9-22 cancer cells, and 10 was broadly cytotoxic toward all six test cancer cell lines used. Compounds 1, 3, 7, and 10 were found to inhibit the accumulation of the pro-inflammatory proteins iNOS and COX-2 at 10 μM.
Chao
Chih-Hua
CH
Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 804, Taiwan, Republic of China.
Wen
Zhi-Hong
ZH
Wu
Yang-Chang
YC
Yeh
Hsiao-Chien
HC
Sheu
Jyh-Horng
JH
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D015394:Molecular Structure; D052247:Nitric Oxide Synthase Type II / Q000037:antagonists & inhibitors
D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D052246:Cyclooxygenase 2 Inhibitors; D004224:Diterpenes; D008070:Lipopolysaccharides; D052247:Nitric Oxide Synthase Type II