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

doi:10.1007/s00706-015-1554-0

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

Chemistry

Research output: Contribution to journal › Article › peer-review

6 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 language	English
Pages (from-to)	1763-1770
Number of pages	8
Journal	Monatshefte fur Chemie
Volume	146
Issue number	10
Early online date	27 Aug 2015
DOIs	https://doi.org/10.1007/s00706-015-1554-0
Publication status	Published - Oct 2015

Bibliographical note

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.

Keywords

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

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Takahashi, J. A., Floreano, M. B., Oliveira, M. S., Oliveira, T. S., Tabudravu, J. N., Wardell, J. L., & Wardell, S. M. S. V. (2015). 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. Monatshefte fur Chemie, 146(10), 1763-1770. https://doi.org/10.1007/s00706-015-1554-0

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

Research output: Contribution to journal › Article › peer-review

Takahashi, JA, Floreano, MB, Oliveira, MS, Oliveira, TS, Tabudravu, JN, Wardell, JL & Wardell, SMSV 2015, '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', Monatshefte fur Chemie, vol. 146, no. 10, pp. 1763-1770. https://doi.org/10.1007/s00706-015-1554-0

Takahashi JA, Floreano MB, Oliveira MS, Oliveira TS, Tabudravu JN, Wardell JL 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. Monatshefte fur Chemie. 2015 Oct;146(10):1763-1770. Epub 2015 Aug 27. doi: 10.1007/s00706-015-1554-0

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title = "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",

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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author = "Takahashi, {Jacqueline A.} and Floreano, {M{\^o}nica B.} and Oliveira, {Mariana S.} and Oliveira, {Thais S.} and Tabudravu, {Jioji N.} and Wardell, {James L.} and Wardell, {Solange M S V}",

note = "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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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.

PY - 2015/10

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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).

KW - (+) Pinitol

KW - (-)-N-Acetylanonaine

KW - Liriodenine

KW - Michelia champaca

KW - X-ray crystallography

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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

Abstract

Bibliographical note

Keywords

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