Isolation and Biomimetic Synthesis of Anti-inflammatory Stilbenolignans from Gnetum cleistostachyum

• Published in: Chemical & Pharmaceutical Bulletin Vol. 54; no. 7; pp. 1053 - 1057
• Main Authors: Yao, Chun-Suo, Lin, Mao, Wang, Lin
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 2006; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - isolation & purification; Anti-Inflammatory Agents - pharmacology; Gnetaceae; gnetucleistol F; Gnetum - chemistry; Gnetum cleistostachyum; Inhibitory Concentration 50; Lignans - chemical synthesis; Lignans - isolation & purification; Lignans - pharmacology; Magnetic Resonance Spectroscopy; Malondialdehyde - antagonists & inhibitors; Molecular Structure; Stilbenes - chemical synthesis; Stilbenes - isolation & purification; Stilbenes - pharmacology; stilbenolignan; TNF-α activity; Tumor Necrosis Factor-alpha - antagonists & inhibitors; Tumor Necrosis Factor-alpha - drug effects
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.54.1053

One new stilbenolignan, gnetucleistol F (1), and four known stilbenolignans, gnetofuran A (2), lehmbachol D (3), gnetifolin F (4) and gnetumontanin C (5) were isolated from the lianas of Gnetum cleistostachyum C. Y. CHENG (Gnetaceae). Their structures and relative configurations were determined by means of spectroscopic evidence. Compounds 1, 2, 3 and 4 were synthesized for the first time on the basis of their biogenetic pathway, and their possible biomimetical synthetic mechanisms were discussed. The pharmacological activities of all stilbenolignans have been tested. Among them, 1, 2, 3, 4 and 5 showed moderate inhibitory activities on TNF-α and 1 also showed potent inhibitory activity on malondialdehyde.