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

Received: 18 December 2012; in revised form: 22 January 2013 / Accepted: 31 January 2013 / Published: 5 February 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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
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MDPI and ACS Style

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.

AMA Style

Derita M, Montenegro I, Garibotto F, Enriz RD, Fritis MC, Zacchino SA. Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies. Molecules. 2013; 18(2):2029-2051.

Chicago/Turabian Style

Derita, Marcos; Montenegro, Iván; Garibotto, Francisco; Enriz, Ricardo D.; Fritis, Mauricio C.; Zacchino, Susana A. 2013. "Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies." Molecules 18, no. 2: 2029-2051.

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