lignans and kakoul

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.

Topics: Animals; Aristolochiaceae; Cell Line; Dioxoles; Dose-Response Relationship, Drug; Lignans; Lipopolysaccharides; Mice; Microglia; Molecular Structure; Nitric Oxide; Plant Roots; Polyunsaturated Alkamides; Propiophenones; Stereoisomerism; Structure-Activity Relationship; Toluene

Three compounds were isolated from the roots and stems of Asarum chinese Franch. f. fargesii (Franch.) C. Y. Cheng with column chromatography methods. Their structures were identified as kakuol (I), 2-methoxy-4,5-methylenedioxypropiophenone (II) and pluviatilol (III) on the basis of physicochemical and spectroscopic analysis. The compound II and III were isolated from the genus of Asarum for the first time.

Topics: Asarum; Lignans; Molecular Structure; Plants, Medicinal; Propiophenones; Rhizome; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet