A Novel Cyclopentene Derivative and a Polyhydroxylated Steroid from a South China Sea Gorgonian Menella sp

• Published in: Chemical & Pharmaceutical Bulletin Vol. 58; no. 10; pp. 1391 - 1394
• Main Authors: Xing-Yun CHAIa, Jian-Fan SUNa, Li-Ying TANGb, Xian-Wen YANGa, Yun-Qiu LIa, Hui HUANGa, c, Xue-Feng ZHOUa, Bin YANGa, Yonghong LIUa
• Format: Journal Article
• Language: Japanese
• Published: Pharmaceutical Society of Japan 2010
• ISSN: 0009-2363; 1347-5223

A chemical investigation on a South China Sea gorgonian, Menella sp. resulted in the isolation and elucidation of menellin A (1), a highly oxygenated racemate with C8 skeleton, and a polyhydroxylated steroid, menellsteroid C (2), along with eight known compounds (3-10). The structures of the new compounds were elucidated by means of MS, 1D and 2D NMR spectra, and the relative stereochemistry of 1 was determined by X-ray single-crystal diffraction analysis. In addition, compound 7 was isolated as a new natural product. Compounds 1-3 and 7 were selected to test the anti-inflammatory inhibition against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 macrophages. 1 and 3 exhibited modest inhibitory effects with IC50 of 71.3, 33.9μM, respectively, compared to the positive control aminoguanidine (IC50 25.0μM). Gorgonians, with trivial names of Sea Fan or Sea Whip etc., are one of the important sources recognized the new and significant biological activity of metabolites and are arousing the interest of chemists all over the world. There are a large number of papers every year on secondary metabolite research of the gorgonians1-4). However, one of the prolific gorgonian in the South China Sea, the Menella sp., has been given comparatively less attention, with the exception of four papers that described the guaiane sesquiterpenoids, polyhydroxylated steroids and other known compounds5-8).