Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects

Biosci Biotechnol Biochem. 2004 Jan;68(1):85-90. doi: 10.1271/bbb.68.85.

Abstract

Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4-9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09-0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1-3, 5 and 9, with a potent inhibitory effect on EBV-EA induction (91-93% inhibition at 1x10(3) mol ratio/TPA). Furthermore, compound 5 exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • 9,10-Dimethyl-1,2-benzanthracene / adverse effects
  • Animals
  • Anti-Inflammatory Agents / pharmacology*
  • Antigens, Viral / drug effects
  • Antineoplastic Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical / methods
  • Female
  • Mice
  • Mice, Inbred ICR
  • Otitis / chemically induced
  • Otitis / drug therapy
  • Papilloma / chemically induced
  • Papilloma / drug therapy
  • Perilla frutescens / chemistry*
  • Plant Leaves / chemistry
  • Skin Neoplasms / chemically induced
  • Skin Neoplasms / drug therapy
  • Tetradecanoylphorbol Acetate / adverse effects
  • Tetradecanoylphorbol Acetate / pharmacology
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Anti-Inflammatory Agents
  • Antigens, Viral
  • Antineoplastic Agents
  • Epstein-Barr virus early antigen
  • Triterpenes
  • euscaphic acid
  • 9,10-Dimethyl-1,2-benzanthracene
  • Tetradecanoylphorbol Acetate