Structure-activity relationship of polyisoprenyl benzophenones from Garcinia pyrifera on the tubulin/microtubule system

J Nat Prod. 2000 Aug;63(8):1070-6. doi: 10.1021/np0000872.

Abstract

Microtubule disassembly inhibitory properties have been established for the known polyisoprenylated benzophenones xanthochymol (1a) and guttiferone E (1b). The compounds were isolated from the fruits of Garcinia pyrifera collected in Malaysia. A structure-activity relationship study, including natural and semisynthetic derivatives, delineated some structural features necessary for the interaction with tubulin within this compound class.

MeSH terms

  • Benzophenones / chemistry
  • Benzophenones / pharmacology*
  • Butadienes / chemistry
  • Butadienes / pharmacology*
  • Chromatography, Gel
  • Chromatography, High Pressure Liquid
  • Fruit / chemistry*
  • Gas Chromatography-Mass Spectrometry
  • Hemiterpenes*
  • Humans
  • KB Cells / drug effects
  • Magnetic Resonance Spectroscopy
  • Malaysia
  • Microtubules / drug effects*
  • Optical Rotation
  • Pentanes*
  • Plants, Medicinal / chemistry*
  • Rosales / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship
  • Tubulin / analysis
  • Tubulin / biosynthesis

Substances

  • Benzophenones
  • Butadienes
  • Hemiterpenes
  • Pentanes
  • Tubulin
  • isoprene
  • xanthochymol
  • guttiferone E