Abstract

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 13,4,5-trimethoxytoluene3 (=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 IC₅₀ 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. © 2008 Verlag Helvetica Chimica Acta AG, Zürich.

Indexed keywords

EMTREE drug terms: 3,4,5 trimethoxytoluene; asaricin; asarinin; Asarum sieboldii extract; elemicin; herbaceous agent; kakuol; lipopolysaccharide; methyleugenol; methylkakuol; n (2 methylpropyl)dodeca 2,4,8,10 tetraenamide; natural product; nitric oxide; safrole; sesamin; unclassified drug; (2E,4E,8Z,10E) N (2 methylpropyl)dodeca 2,4,8,10 tetraenamide; (2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide; 1,3 dioxolane derivative; 3,4,5 trimethoxytoluene; 3,4,5-trimethoxytoluene; amide; drug derivative; kakoul; lignan; lipopolysaccharide; nitric oxide; propiophenone derivative; sesamin; toluene

EMTREE medical terms: animal cell; article; Asarum; Asarum sieboldii; controlled study; drug identification; drug isolation; drug potency; drug structure; IC 50; microglia; mouse; nonhuman; animal; Aristolochiaceae; biosynthesis; cell line; chemical structure; chemistry; cytology; dose response; drug antagonism; drug effect; isolation and purification; metabolism; microglia; plant root; stereoisomerism; structure activity relation

Species Index: Asarum sieboldii

MeSH: 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
Medline is the source for the MeSH terms of this document.

Chemicals and CAS Registry Numbers: asarinin, 133-04-0, 133-05-1; elemicin, 4179-19-5, 487-11-6; methyleugenol, 93-15-2; nitric oxide, 10102-43-9; safrole, 94-59-7; sesamin, 607-80-7, 7076-24-6; amide, 17655-31-1; toluene, 108-88-3;(2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide; 3,4,5-trimethoxytoluene, 6443-69-2; Dioxoles; kakoul, 18607-90-4; Lignans; Lipopolysaccharides; Nitric Oxide, 10102-43-9; Polyunsaturated Alkamides; Propiophenones; sesamin, 607-80-7; Toluene, 108-88-3