Bioactive Dimeric Abietanoid Peroxides from the Bark of Cryptomeria japonica

Molecules. 2019 Jun 10;24(11):2178. doi: 10.3390/molecules24112178.

Abstract

Three new dimeric abietane-type diterpenoids, abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7α-yl peroxide (1), abieta-6,8,11,13-tetraen-12-yl 12-hydroxyabieta-8,11,13-trien-7β-yl peroxide (2), and 12-hydroxyabieta-8,11,13-trien-7β-yl 7-oxoabieta-5,8,11,13-tetraen-12-yl peroxide (3), together with four known abietane-type diterpenoids (4-7) were isolated from the methanol extract of the bark of Cryptomeria japonica. Their structures were elucidated on the basis of spectroscopic analysis and comparison of NMR data with those of known analogues. At a concentration of 50 μM, compounds 1, 2, and 3 showed 26.2%, 23.6%, and 35.7% inhibition towards xanthine oxidase enzyme, respectively. In addition, compound 3 also showed 24.9% inhibition toward angiotensin-converting enzyme (ACE).

Keywords: Cryptomeria japonica; Cupressaceae; dimeric abietane; diterpenoid.

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification
  • Abietanes / pharmacology*
  • Angiotensin-Converting Enzyme Inhibitors
  • Animals
  • Cryptomeria / chemistry*
  • Dimerization*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Peptidyl-Dipeptidase A / metabolism
  • Peroxides / chemistry
  • Peroxides / isolation & purification
  • Peroxides / pharmacology*
  • Plant Bark / chemistry*
  • Rabbits
  • Xanthine Oxidase / antagonists & inhibitors

Substances

  • Abietanes
  • Angiotensin-Converting Enzyme Inhibitors
  • Enzyme Inhibitors
  • Peroxides
  • Xanthine Oxidase
  • Peptidyl-Dipeptidase A