Isolation and biomimetic synthesis of anti-inflammatory stilbenolignans from Gnetum cleistostachyum.
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-alpha and 1 also showed potent inhibitory activity on malondialdehyde.
Yao
Chun-Suo
CS
Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine (Ministry of Education), Peking Union Medical College; Beijing 100050, PR China.
Lin
Mao
M
Wang
Lin
L
D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D035684:Gnetum / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D017705:Lignans / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008315:Malondialdehyde / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D013267:Stilbenes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000187:drug effects
D000893:Anti-Inflammatory Agents; D017705:Lignans; D013267:Stilbenes; D014409:Tumor Necrosis Factor-alpha; D008315:Malondialdehyde