Chemical constituents of the bark of Machilus wangchiana and their biological activities

J Nat Prod. 2009 Dec;72(12):2145-52. doi: 10.1021/np900504a.

Abstract

Eleven new metabolites, butanolides 1-6, lignan derivatives 7-9, sesquiterpene 10, and 3',4'-seco-flavane derivative 11, have been isolated from an ethanol extract of Machilus wangchiana. Twenty known compounds, including ginkgolides A and B (16 and 17), were also isolated. Their structures and absolute configurations were determined by spectroscopic and chemical methods. Compounds 7, 8a, 8b, 9, 11, (+)-guaiacin (12), meso-dihydroguaiaretic acid (13), and hamabiwalactone A (15) showed potent in vitro activities against the release of beta-glucuronidase in rat polymorphonuclear leukocytes (PMNs) induced by platelet-activating factor (PAF), with 42.5-75.6% inhibition at 10(-5) M. Compounds 8, 8a, 8b, 9, and 11 reduced dl-galactosamine (GalN)-induced hepatocyte (WB-F344 cells) damage with 39.4 +/- 6.3% to 53.6 +/- 3.5% inhibition at 10(-4) M. Isomahubannolide-23 (14) was cytotoxic against human stomach cancer (BGC-823) and ovarian cancer (A2780) cell lines, with IC(50) values of 0.13 and 2.66 muM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification*
  • 4-Butyrolactone / pharmacology
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Drugs, Chinese Herbal / pharmacology
  • Female
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Ginkgolides / isolation & purification
  • Glucuronidase / blood
  • Glucuronidase / drug effects
  • Humans
  • Lactones / isolation & purification
  • Lauraceae / chemistry*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Molecular Structure
  • Neutrophils / drug effects
  • Plant Bark / chemistry
  • Rats
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Stereoisomerism

Substances

  • Antineoplastic Agents, Phytogenic
  • Drugs, Chinese Herbal
  • Flavonoids
  • Ginkgolides
  • Lactones
  • Lignans
  • Sesquiterpenes
  • ginkgolide B
  • Glucuronidase
  • 4-Butyrolactone
  • ginkgolide A