Identification and quantification of the fatty acids and isolation of (+)-pinitol, liriodenine, and (-)-N-acetyl-anonaine from empty capsules of Michelia champaca fruits. Crystal structure of (-)-N-acetylanonaine

Jacqueline A. Takahashi*, Mônica B. Floreano, Mariana S. Oliveira, Thais S. Oliveira, Jioji N. Tabudravu, James L. Wardell, Solange M S V Wardell

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The identity of fatty acids, as their methyl esters, present in the empty seed pods of Michelia champaca is reported as well as the characterisation of three compounds, namely (+)-pinitol, liriodenine, and (-)-N-acetylanonaine. The identification of these compounds was generally obtained by spectroscopic methods, and additionally by X-ray crystallography for N-acetylanonaine. The antimicrobial activity of the isolated compounds against the Gram-positive test strains Bacillus cereus ATCC 11778, Listeria monocitogenes ATCC 15313, and Staphylococcus aureus ATCC 29213 is described. In general (-)-N-acetylanonaine was the most active compound. However, the selectivity of liriodenine towards S. aureus suggests that further study would be worthwhile. (-)-N-Acetylanonaine crystallizes in the orthorhombic space group P2<inf>1</inf>2<inf>1</inf>2<inf>1</inf> with a = 6.0773(2) Å, b = 11.6053(5) Å, c = 20.9906(9) (11) Å, and Z = 4. Graphical abstract: (Figure Presented).

Original languageEnglish
Pages (from-to)1763-1770
Number of pages8
JournalMonatshefte fur Chemie
Volume146
Issue number10
Early online date27 Aug 2015
DOIs
Publication statusPublished - Oct 2015

Keywords

  • (+) Pinitol
  • (-)-N-Acetylanonaine
  • Liriodenine
  • Michelia champaca
  • X-ray crystallography

ASJC Scopus subject areas

  • Chemistry(all)

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