Triterpenoids from the leaves of Diospyros kaki (persimmon) and their inhibitory effects on protein tyrosine phosphatase 1B

J Nat Prod. 2008 Oct;71(10):1775-8. doi: 10.1021/np800298w. Epub 2008 Sep 18.

Abstract

Phytochemical study on a methanol-soluble extract of the leaves of persimmon (Diospyros kaki) resulted in the isolation of two new ursane-type triterpenoids, 3alpha,19alpha-dihydroxyurs-12,20(30)-dien-24,28-dioic acid (1) and 3alpha,19alpha-dihydroxyurs-12-en-24,28-dioic acid (2), together with 12 known ursane- and oleanane-type triterpenoids (3-14). Triterpenoids with a 3beta-hydroxy group were found to inhibit protein tyrosine phosphatase 1B (PTP1B) activity, with IC50 values ranging from 3.1+/-0.2 to 18.8+/-1.3 microM, whereas those with a 3alpha-hydroxy moiety were not active.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diospyros / chemistry*
  • Humans
  • Korea
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Triterpenes* / chemistry
  • Triterpenes* / isolation & purification
  • Triterpenes* / pharmacology

Substances

  • 3alpha,19alpha-dihydroxyurs-12,20(30)-dien-24,28-dioic acid
  • 3alpha,19alpha-dihydroxyurs-12-en-24,28-dioic acid
  • Triterpenes
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1