Constituents of Asarum sieboldii with inhibitory activity on lipopolysaccharide (LPS)-induced NO production in BV-2 microglial cells.
Bioassay-guided fractionation of the root extract of Asarum sieboldii led to the isolation of the four active compounds (-)-sesamin (1), (2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide (2), kakuol (3), and '3,4,5-trimethoxytoluene' (=1,2,3-trimethoxy-5-methylbenzene; 4), in terms of inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production. Compounds 1-4 showed potent inhibition of NO production, with IC(50) values in the low nanomolar-to-micromolar range. Also isolated were the known compounds methylkakuol (5), '3,5-dimethoxytoluene', safrole, asaricin, methyleugenol, and (-)-asarinin, which were found to be inactive in the above assay. Among the ten known isolates, compounds 1, 2, and 5 were found for the first time in this plant.
Han
Ah-Reum
AR
BK21 Oriental Medical Science Center, College of Oriental Medicine, Kyung Hee University, 1 Hoeki-dong, Dongdaemun-gu, Seoul 130-701, Korea.
Kim
Hye Jeoung
HJ
Shin
Minkyu
M
Hong
Moochang
M
Kim
Yang Seok
YS
Bae
Hyunsu
H
D000818:Animals; D029065:Aristolochiaceae / Q000737:chemistry; D002460:Cell Line; D004149:Dioxoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors* / Q000494:pharmacology; D051379:Mice; D017628:Microglia / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D018517:Plant Roots / Q000737:chemistry; D053284:Polyunsaturated Alkamides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D011427:Propiophenones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
C532089:(2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide; D004149:Dioxoles; D017705:Lignans; D008070:Lipopolysaccharides; D053284:Polyunsaturated Alkamides; D011427:Propiophenones; C049775:kakoul; D009569:Nitric Oxide; D014050:Toluene; C017776:3,4,5-trimethoxytoluene; C054125:sesamin