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Zeitschrift für Naturforschung C

A Journal of Biosciences

Editor-in-Chief: Seibel, Jürgen

Editorial Board: Aigner , Achim / Boland, Wilhelm / Bornscheuer, Uwe / Hoffmann, Klaus


IMPACT FACTOR 2018: 1.000

CiteScore 2018: 0.99

SCImago Journal Rank (SJR) 2018: 0.246
Source Normalized Impact per Paper (SNIP) 2018: 0.437

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1865-7125
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Volume 63, Issue 11-12

Issues

Structure and Spasmolytic Activity Relationships of Monoterpene Analogues Found in Many Aromatic Plants

Damião P. de Sousa
  • Corresponding author
  • Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-900, São Cristóvão, Sergipe, Brazil.
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/ Genival A. S. Júnior
  • Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-900, São Cristóvão, Sergipe, Brazil.
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  • De Gruyter OnlineGoogle Scholar
/ Luciana N. Andrade
  • Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-900, São Cristóvão, Sergipe, Brazil.
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/ Flávia R. Calasans
  • Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-900, São Cristóvão, Sergipe, Brazil.
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/ Xirley P. Nunes
  • Laboratório de Tecnologia Farmacê utica, Universidade Federal da Paraíba, Caixa Postal 5009, CEP 58051-970, João Pessoa, Paraíba, Brazil
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/ José M. Barbosa-Filho
  • Laboratório de Tecnologia Farmacê utica, Universidade Federal da Paraíba, Caixa Postal 5009, CEP 58051-970, João Pessoa, Paraíba, Brazil
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/ Josemar S. Batista
  • Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-900, São Cristóvão, Sergipe, Brazil.
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Published Online: 2014-06-02 | DOI: https://doi.org/10.1515/znc-2008-11-1205

Abstract

Rotundifolone, a monoterpene isolated from the essential oil of the leaves of Mentha x villosa, is a constituent of several essential oils and known to have spasmolytic activity. The present study aimed to investigate the correlation between structure and spasmolytic activity of rotundifolone and its analogues in ileum isolated from guinea-pig. Five of the seven tested analogues were found to have a spasmolytic effect more potent than rotundifolone itself, except for pulegone and (+)-limonene. The comparison between rotundifolone and limonene oxide showed that the absence of the keto group did not decrease the relaxant effect. Comparison of the spasmolytic activity between rotundifolone and (+)-pulegone showed that the absence of the epoxy group did not decrease the relaxation of the ileum. Carvone epoxide was found to be significantly more potent than rotundifolone. The monoterpene (-)-carvone produced ileum relaxation and was more potent than its enantiomer (+)-carvone. (+)-Limonene and pulegone oxide showed a similar effect. The study showed that the functional groups and their position at the ring of rotundifolone contributed to the relaxation activity of the ileum. The absence of the oxygenated molecular structure is not a critical requirement for the molecule to be bioactive.

Keywords: Terpenes; Essential Oils; Smooth Muscle

About the article

Received: 2008-03-10

Revised: 2008-05-23

Published Online: 2014-06-02

Published in Print: 2008-12-01


Citation Information: Zeitschrift für Naturforschung C, Volume 63, Issue 11-12, Pages 808–812, ISSN (Online) 1865-7125, ISSN (Print) 0939-5075, DOI: https://doi.org/10.1515/znc-2008-11-1205.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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