Nitric oxide scavenging lignans from Vitex negundo seeds.
A new phenyldihydronaphthalene-type lignan, vitexdoin A (1), a new phenylnaphthalene-type lignan alkaloid, vitedoamine B (2), four new phenylnaphthalene-type lignans, vitexdoins B-E (3-6), and four known lignan derivatives (7-10) were isolated from Vitex negundo seeds. Their structures were elucidated by detailed analyses of NMR, IR, and MS data. The ability of the isolates to prevent nitric oxide (NO) production by LPS-stimulated RAW 264.7 macrophages in a concentration-dependent manner was also studied. Compounds 5, 6, and 9 were among the most potent NO production inhibitors, with IC(50) values of 0.13, 0.15, and 0.11 microM, respectively. The introduction of free hydroxy groups plays a vital role in the potency of these compounds.
Zheng
Cheng-Jian
CJ
Department of Pharmacognosy, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai, People's Republic of China.
Huang
Bao-Kang
BK
Han
Ting
T
Zhang
Qiao-Yan
QY
Zhang
Hong
H
Rahman
Khalid
K
Qin
Lu-Ping
LP
D000818:Animals; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D012639:Seeds / Q000737:chemistry; D013329:Structure-Activity Relationship; D020950:Vitex / Q000737:chemistry*
D017705:Lignans; D008070:Lipopolysaccharides; C544282:vitedoamine B; C544281:vitexdoin A; D009569:Nitric Oxide