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Monatshefte für Chemie - Chemical Monthly

, Volume 146, Issue 10, pp 1763–1770 | Cite as

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. TakahashiEmail author
  • Mônica B. Floreano
  • Mariana S. Oliveira
  • Thais S. Oliveira
  • Jioji N. Tabudravu
  • James L. Wardell
  • Solange M. S. V. Wardell
Original Paper

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 P212121 with a = 6.0773(2) Å, b = 11.6053(5) Å, c = 20.9906(9) (11) Å, and Z = 4.

Graphical abstract

Keywords

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

Notes

Acknowledgments

The use of the NCS crystallographic service at Southampton and the valuable assistance of the staff there are gratefully acknowledged. JAT thanks FAPEMIG and CNPq for support: JLW thanks FAPERJ and CNPq, Brazil for support.

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Copyright information

© Springer-Verlag Wien 2015

Authors and Affiliations

  • Jacqueline A. Takahashi
    • 1
    Email author
  • Mônica B. Floreano
    • 1
  • Mariana S. Oliveira
    • 1
  • Thais S. Oliveira
    • 1
  • Jioji N. Tabudravu
    • 2
  • James L. Wardell
    • 2
    • 3
  • Solange M. S. V. Wardell
    • 4
  1. 1.Departamento de Química, ICExUniversidade Federal de Minas GeraisBelo HorizonteBrazil
  2. 2.Department of ChemistryUniversity of AberdeenOld AberdeenScotland, UK
  3. 3.FioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-ManguinhosRua Sizenando NabucoRio De JaneiroBrazil
  4. 4.CHEMSOLAberdeenScotland, UK

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