Isolation of Three New Diterpenes from Dodonaea viscosa

Chem Pharm Bull (Tokyo). 2021;69(1):40-47. doi: 10.1248/cpb.c20-00327.

Abstract

An investigation into the methanol extracts obtained from the stems of Dodonaea viscosa led to the isolation of one nor-clerodane diterpene (1) and two labdane diterpenes (2, 3), as well as 17 known compounds (4-20). The structures of these compounds were elucidated based on chemical and spectral evidence. The stereochemical structure of the nor-clerodane diterpene was confirmed via its circular dichroism spectrum and calculated electronic circular dichroism spectrum. Isolated compounds were evaluated for their inhibitory effects on collagenase and tyrosinase. Since 5,7,4'-trihydroxy-3'-(4-hydroxy-3-methylbutyl)-5'-(3-methylbut-2-enyl)-3,6-dimethoxyflavone (9) showed collagenase inhibitory activity and scopoletin (12) had significant tyrosinase inhibitory activity, they were considered to be good candidates for cosmetic agents.

Keywords: Dodonaea viscosa; Sapindaceae; circular dichroism; collagenase inhibitor; diterpene; tyrosinase inhibitor.

MeSH terms

  • Agaricales / enzymology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Gelatinases / antagonists & inhibitors
  • Gelatinases / metabolism
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Monophenol Monooxygenase / metabolism
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Sapindaceae / chemistry*
  • Stereoisomerism

Substances

  • Diterpenes
  • Plant Extracts
  • Monophenol Monooxygenase
  • Gelatinases