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Molecules 2013, 18(2), 2029-2051; doi:10.3390/molecules18022029
Article

Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies

1, 2, 3,4, 3,4, 2,† and 1,†,*
1 Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina 2 Laboratorio de Ciencias Químicas y Recursos naturales, Facultad de Farmacia, Universidad de Valparaíso, Avenida Gran Bretaña 1111, Playa Ancha, 2340000 Valparaíso, Chile 3 Departamento de Química, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco 915, 5700 San Luis, Argentina 4 IMIBIO-SL (CONICET), Chacabuco 915, 5700 San Luis, Argentina These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 18 December 2012 / Revised: 22 January 2013 / Accepted: 31 January 2013 / Published: 5 February 2013
(This article belongs to the Section Natural Products)
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Abstract

Seventeen drimanes including polygodial (1), isopolygodial (2), drimenol (3) and confertifolin (4) obtained from natural sources and the semi-synthetic derivatives 5–17 obtained from 1–3, were evaluated in vitro for antifungal properties against a unique panel of fungi with standardized procedures by using two end-points, MIC100 and MIC50. A SAR analysis of the whole series, supported by conformational and electronic studies, allowed us to show that the Δ7,8 -double bond would be one of the key structural features related to the antifungal activity. The MEPs obtained for active compounds exhibit a clear negative minimum value (deep red zone) in the vicinity of the Δ7,8 -double bond, which is not present in the inactive ones. Apart of this negative zone, a positive region (deep blue) appears in 1, which is not observed either in its epimer 2 nor in the rest of the active compounds. The LogP of active compounds varies between 2.33 and 3.84, but differences in MICs are not correlated with concomitant variations in LogP values.
Keywords: antifungal agents; drimanes; structure-activity relationships; stereo-electronic studies antifungal agents; drimanes; structure-activity relationships; stereo-electronic studies
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Derita, M.; Montenegro, I.; Garibotto, F.; Enriz, R.D.; Fritis, M.C.; Zacchino, S.A. Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies. Molecules 2013, 18, 2029-2051.

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