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: Chai, Xing-Yun, Sun, Jian-Fan, Tang, Li-Ying, Yang, Xian-Wen, Li, Yun-Qiu, Huang, Hui, Zhou, Xue-Feng, Yang, Bin, Liu, Yonghong
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.10.2010; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Animals; Anthozoa - chemistry; Anti-Inflammatory Agents - chemistry; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; anti-inflammatory inhibition; Cell Line; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; China; Crystallography, X-Ray; Cyclopentanes - chemistry; Cyclopentanes - isolation & purification; Cyclopentanes - pharmacology; Gorgonacea; gorgonian; Life Sciences & Biomedicine; Lipopolysaccharides - pharmacology; Magnetic Resonance Spectroscopy; Menella sp; menellin A; menellsteroid C; Mice; Molecular Conformation; Nitric Oxide - metabolism; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Steroids - chemistry; Steroids - isolation & purification; Steroids - pharmacology; X-ray diffraction; China; ISEW, South China Sea; anti-inflammatory inhibition; OXYGENATED GUAIANE LACTONES; POLYOXYGENATED STEROIDS; VERRUCOSA BRUNDIN; menellsteroid C; X-ray diffraction; Menella sp; gorgonian; menell in A; MARINE NATURAL-PRODUCTS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.58.1391

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, 33.9 μM, respectively, compared to the positive control aminoguanidine (IC50 25.0 μM).