Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation

Kohei Kamiya, Yohei Tanaka, Endang Hanani, Umar Mansur, Toshiko Satake

Research output: Contribution to journalArticle

116 Citations (Scopus)

Abstract

The oxidative modification of low-density lipoprotein (LDL) plays an important role in the genesis of arteriosclerosis. The present study focused on the effects of the fruits of Morinda citrifolia on preventing arteriosclerosis. The MeOH extract and CHCl3-, EtOAc-, n-BuOH-, and H 2O-soluble phases derived from the fruits of M. citrifolia were evaluated for their inhibitory activity on copper-induced LDL oxidation by the thiobarbituric acid-reactive substances (TBARS) method. The MeOH extract and EtOAc-soluble phase showed 88 and 96% inhibition, respectively. Six lignans were isolated by repeated column chromatography from the EtOAc-soluble phase. These compounds were determined by spectroscopic analysis to be 3,3′- bisdemethylpinoresinol (1), americanol A (2), americanin A (3), americanoic acid A (4), morindolin (5), and isoprincepin (6), of which 4 and 5 are novel compounds. These compounds inhibited copper-induced LDL oxidation in a dose-dependent manner, 1, 2, 5, and 6 exhibited remarkably strong activities, which were the same or better than that of the known antioxidant 2,6-di-tert-butyl-p-cresol. The IC50 values for 1, 2, 5, and 6 were 1.057, 2.447, 2.020, and 1.362 μM, respectively. The activity of these compounds is mainly due to their number of phenolic hydroxyl groups.

Original languageEnglish
Pages (from-to)5843-5848
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume52
Issue number19
DOIs
Publication statusPublished - 22 Sep 2004

Keywords

  • Arteriosclerosis
  • Lignan
  • Low-density lipoprotein
  • Morinda citrifolia
  • Noni
  • Rubiaceae
  • Spectroscopic analysis

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