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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

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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.

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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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Authors and Affiliations

  1. Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Av. Antônio Carlos, 6627, Belo Horizonte, MG, CEP 31270-901, Brazil

    Jacqueline A. Takahashi, Mônica B. Floreano, Mariana S. Oliveira & Thais S. Oliveira

  2. Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK

    Jioji N. Tabudravu & James L. Wardell

  3. FioCruz-Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio De Janeiro, RJ, Brazil

    James L. Wardell

  4. CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland, UK

    Solange M. S. V. Wardell

Authors
  1. Jacqueline A. Takahashi
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  2. Mônica B. Floreano
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  3. Mariana S. Oliveira
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  4. Thais S. Oliveira
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  5. Jioji N. Tabudravu
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Correspondence to Jacqueline A. Takahashi.

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Takahashi, J.A., Floreano, M.B., Oliveira, M.S. et al. 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. Monatsh Chem 146, 1763–1770 (2015). https://doi.org/10.1007/s00706-015-1554-0

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  • DOI: https://doi.org/10.1007/s00706-015-1554-0

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