conidendrin and 1-1-diphenyl-2-picrylhydrazyl

The lignan 7'-hydroxymatairesinol (1), extracted from the knotwoods of fir (Abies alba), spruce (Picea abies), and Douglas fir (Pseudotsuga menziesii), exhibited unexpected reactivity when esterification reactions were attempted on the hydroxy group at position C-7'. To circumvent the rapid intramolecular cyclization procedure, leading quantitatively to the lignan conidendrin (7), a simple strategy for 7'-esterification of 1 under mild conditions (three steps, up to 80% overall yield) was developed. Compared to hydroxymatairesinol (1) (log K'

Topics: alpha-Tocopherol; Antioxidants; Biphenyl Compounds; Lignans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Picea; Picrates; Pinus; Stereoisomerism; Tetrahydronaphthalenes

From the aqueous extract of the wood of Taxus yunnanensis, which showed cytochrome P450 3A4 (CYP3A4) inhibition, a new isoflavan [(3S,4R)-4'-hydroxy-6,3'-dimethoxyisoflavan-4-ol (1)], a new degraded lignan [2,3-bis(hydroxymethyl)-7-hydroxy-6-methoxy-1-tetralone (2)], and a new lignan [(7R)-7-hydroxytaxiresinol (3)] were isolated, together with nine known lignans. Among the isolates obtained, α-conidendrin (12) showed strong CYP3A4 inhibition with an IC(50) value of 0.2 μM.

Topics: Antineoplastic Agents, Phytogenic; Antioxidants; Biphenyl Compounds; Colletotrichum; Cytochrome P-450 CYP3A; Cytochrome P-450 CYP3A Inhibitors; Drug Screening Assays, Antitumor; Free Radical Scavengers; Furans; Hep G2 Cells; Humans; Isocoumarins; Isoflavones; Lignans; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Picrates; Taxus; Tetrahydronaphthalenes; Wood