Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies
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 b...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2013-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/18/2/2029 |
| _version_ | 1819150855273709568 |
|---|---|
| author | Susana A. Zacchino Mauricio Cuellar Fritis Ricardo D. Enriz Francisco Garibotto Marcos Derita Iván Montenegro |
| author_facet | Susana A. Zacchino Mauricio Cuellar Fritis Ricardo D. Enriz Francisco Garibotto Marcos Derita Iván Montenegro |
| author_sort | Susana A. Zacchino |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T14:24:08Z |
| format | Article |
| id | doaj.art-da94cbcfb38e4d4992554508410cd0be |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T14:24:08Z |
| publishDate | 2013-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-da94cbcfb38e4d4992554508410cd0be2022-12-21T18:22:55ZengMDPI AGMolecules1420-30492013-02-011822029205110.3390/molecules18022029Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic StudiesSusana A. ZacchinoMauricio Cuellar FritisRicardo D. EnrizFrancisco GaribottoMarcos DeritaIván MontenegroSeventeen 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.http://www.mdpi.com/1420-3049/18/2/2029antifungal agentsdrimanesstructure-activity relationshipsstereo-electronic studies |
| spellingShingle | Susana A. Zacchino Mauricio Cuellar Fritis Ricardo D. Enriz Francisco Garibotto Marcos Derita Iván Montenegro Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies Molecules antifungal agents drimanes structure-activity relationships stereo-electronic studies |
| title | Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies |
| title_full | Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies |
| title_fullStr | Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies |
| title_full_unstemmed | Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies |
| title_short | Structural Requirements for the Antifungal Activities of Natural Drimane Sesquiterpenes and Analogues, Supported by Conformational and Electronic Studies |
| title_sort | structural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues supported by conformational and electronic studies |
| topic | antifungal agents drimanes structure-activity relationships stereo-electronic studies |
| url | http://www.mdpi.com/1420-3049/18/2/2029 |
| work_keys_str_mv | AT susanaazacchino structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies AT mauriciocuellarfritis structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies AT ricardodenriz structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies AT franciscogaribotto structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies AT marcosderita structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies AT ivanmontenegro structuralrequirementsfortheantifungalactivitiesofnaturaldrimanesesquiterpenesandanaloguessupportedbyconformationalandelectronicstudies |