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

Fingerprint

Fruits
Capsules
Fatty Acids
Crystal structure
Bacillus cereus
Listeria
X ray crystallography
Seed
Esters
anonaine
liriodenine
pinitol

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

In: Monatshefte fur Chemie, Vol. 146, No. 10, 10.2015, p. 1763-1770.

Research output: Contribution to journalArticle

Takahashi, Jacqueline A. ; Floreano, Mônica B. ; Oliveira, Mariana S. ; Oliveira, Thais S. ; Tabudravu, Jioji N. ; Wardell, James L. ; Wardell, Solange M S V. / 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. In: Monatshefte fur Chemie. 2015 ; Vol. 146, No. 10. pp. 1763-1770.
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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) {\AA}, b = 11.6053(5) {\AA}, c = 20.9906(9) (11) {\AA}, and Z = 4. Graphical abstract: (Figure Presented).",
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T1 - 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

AU - Takahashi, Jacqueline A.

AU - Floreano, Mônica B.

AU - Oliveira, Mariana S.

AU - Oliveira, Thais S.

AU - Tabudravu, Jioji N.

AU - Wardell, James L.

AU - Wardell, Solange M S V

N1 - 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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N2 - 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: (Figure Presented).

AB - 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: (Figure Presented).

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KW - (-)-N-Acetylanonaine

KW - Liriodenine

KW - Michelia champaca

KW - X-ray crystallography

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