Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii

Planta Med. 2002 Aug;68(8):742-5. doi: 10.1055/s-2002-33787.

Abstract

The absolute stereostructure of a novel skeletal diterpene, standishinal (1), from the bark of Thuja standishii was confirmed by X-ray crystallographic analyses of 1 and its p-bromobenzoate derivative. Aromatase inhibitory activities of standishinal, eight known diterpenes, totarol, 12-methoxyabieta-8,11,13-trien-11-ol, 12-hydroxy-6,7-seco-abieta-8,11,13-triene-6,7-dial, trans-communic acid, labda-8(17),13-dien-12 R,15-olid-19-oic acid, 12 S-hydroxylabda-8(17),13(16),14-trien-19-oic acid, 13-oxo-15,16-dinorlabda-8(17),11 E-dien-19-oic acid and 14-oxo-15-norlabda-8 (17),12 E-dien-19-oic acid from the plant, and four synthetic analogs were evaluated using a recombinant human aromatase. Among them, standishinal and its diacetate derivative had significant inhibitory activities.

MeSH terms

  • Abietanes*
  • Aromatase / metabolism
  • Aromatase Inhibitors*
  • Crystallography, X-Ray
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Molecular Structure
  • Plant Bark / chemistry*
  • Structure-Activity Relationship
  • Thuja / chemistry*

Substances

  • 3,11-dihydroxy-12-methoxyabieta-8,11,13-triene-7-one
  • Abietanes
  • Aromatase Inhibitors
  • Diterpenes
  • Enzyme Inhibitors
  • Aromatase