Anti-inflammatory diterpenes from the seeds of Vitex negundo.
Phytochemical investigation of a dichloromethane-soluble extract of Vitexnegundo seeds led to the isolation of five labdane diterpenes, negundoins A-E (1-5), a 9,10-seco-abietane diterpene, negundoin F (6), a sandaracopimara-7,15-diene diterpene, negundoin G (7), and two known diterpene derivatives (8, 9). Their chemical structures were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. The anti-inflammatory effects of metabolites 1-7 were also evaluated in vitro. Compounds 3 and 5 were among the most potent inhibitors on nitric oxide production by LPS-stimulated RAW 264.7 macrophages, with IC(50) values of 0.12 and 0.23 microM, respectively. Further studies revealed that compounds 3 and 5 (5 microM) significantly reduced the levels of the iNOS protein to 0.40+/-0.13% and 41.02+/-6.02%, respectively, and COX-2 protein to 2.06+/-0.53% and 26.40+/-7.43%, respectively.
Zheng
Cheng-Jian
CJ
Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, PR China.
Huang
Bao-Kang
BK
Wang
Yang
Y
Ye
Qi
Q
Han
Ting
T
Zhang
Qiao-Yan
QY
Zhang
Hong
H
Qin
Lu-Ping
LP
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004224:Diterpenes / Q000032:analysis* / Q000302:isolation & purification / Q000494:pharmacology*; D008264:Macrophages / Q000187:drug effects / Q000276:immunology; D015394:Molecular Structure; D009569:Nitric Oxide / Q000276:immunology; D012639:Seeds / Q000737:chemistry; D020950:Vitex / Q000737:chemistry*
D000893:Anti-Inflammatory Agents; D004224:Diterpenes; C588178:negundoin A; D009569:Nitric Oxide