Glyceroglycolipids from Citrus hystrix, a Traditional Herb in Thailand, Potently Inhibit the Tumor-Promoting Activity of 12-O-Tetradecanoylphorbol 13-Acetate in Mouse Skin

Akira Murakami, Yoshimasa Nakamura, Koichi Koshimizu, Hajime Ohigashi

Research output: Contribution to journalArticle

113 Citations (Scopus)

Abstract

Two glyceroglycolipids were isolated from the leaves of Citrus hystrix (bitter orange), a traditional herb in Thailand. They were identified as 1,2-di-O-α-linolenoyl-3-O-β-galactopyranosyl-sn-glycerol (DLGG, 1) and a mixture of two compounds, 1-O-α-linolenoyl-2-O-palmitoyl-3-O-β-galactopyranosyl-sn-glycerol (2a) and its counterpart (2b) (LPGG, 2). Both lipids were potent inhibitors of tumor promoter-induced Epstein–Barr virus (EBV) activation. The IC50 values of 1 and 2 were strikingly lower than those of representative cancer preventive agents such as α-linolenic acid, β-carotene, or (−)-epigallocatechin gallate. In a two-stage carcinogenesis experiment on ICR mouse skin with dimethylbenz[α]anthracene (DMBA) and 12-O-tetradecanoylphorbol 13-acetate (TPA), compound 1 exhibited anti-tumor-promoting activity even at a dose 10 times lower than that of α-linolenic acid. As some synthetic detergents or saponins were entirely inactive in the EBV activation inhibition test, detergency was suggested not to play a major role in the mode of inhibitory action in vivo. The inhibition of the arachidonic acid cascade may be involved in anti-tumor promotion since 1 inhibited TPA-induced edema formation in the anti-inflammation test using ICR mouse ears.

Original languageEnglish
Pages (from-to)2779-2783
Number of pages5
JournalJournal of agricultural and food chemistry
Volume43
Issue number10
DOIs
Publication statusPublished - Oct 1 1995
Externally publishedYes

Keywords

  • Cancer chemoprevention
  • Citrus hystrix
  • EB virus
  • Raji cells
  • anti-tumor promoter
  • glyceroglycolipid
  • herb
  • spice

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

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