Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl.
Vatairea guianenis Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a V. guianensis leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (1-4 and 8) and six undescribed isoflavones, vatairenones C-H( 5-7 and 9-11). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (1-7) or ring-closed forms (8-11). The most bioactive compound (3) exhibited in vitro activity against clinically relevant bacteria and fungi with IC50 values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound 3 is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of V. guianensis in the treatment of dermatological disorders. 1H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations.
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2022-07-29
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| Subjects: | Planta Medicinal, Fabaceae, Medicinal plants, |
| Online Access: | http://www.alice.cnptia.embrapa.br/alice/handle/doc/1145058 https://doi.org/10.1021/acs.jnatprod.1c01035 |
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dig-alice-doc-11450582022-08-09T10:20:45Z Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. ÇIÇEK, S. S. PÉREZ, M. G WENZEL-STORJOHANN, A. BEZERRA, R. M. SEGOVIA, J. F. O. GIRRESER, U. KANZAKI, I. TASDEMIR, D. SERHAT S. ÇIÇEK, KIEL UNIVERSITY; MAYRA GALARZA PÉREZ, KIEL UNIVERSITY; ARLETTE WENZEL-STORJOHANN, GEOMAR; ROBERTO M. BEZERRA, UNIFAP; JORGE FEDERICO ORELLANA SEGOVIA, CPAF-AP; ULRICH GIRRESER, KIEL UNIVERSITY; ISAMU KANZAKI, UNB; DENIZ TASDEMIR, GEOMAR. Planta Medicinal Fabaceae Medicinal plants Vatairea guianenis Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a V. guianensis leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (1-4 and 8) and six undescribed isoflavones, vatairenones C-H( 5-7 and 9-11). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (1-7) or ring-closed forms (8-11). The most bioactive compound (3) exhibited in vitro activity against clinically relevant bacteria and fungi with IC50 values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound 3 is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of V. guianensis in the treatment of dermatological disorders. 1H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations. 2022-08-09T10:20:36Z 2022-08-09T10:20:36Z 2022-07-29 2022 Artigo de periódico Journal of Natural Products, v. 85, p. 927-935, 2022. http://www.alice.cnptia.embrapa.br/alice/handle/doc/1145058 https://doi.org/10.1021/acs.jnatprod.1c01035 Ingles en openAccess |
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Planta Medicinal Fabaceae Medicinal plants Planta Medicinal Fabaceae Medicinal plants ÇIÇEK, S. S. PÉREZ, M. G WENZEL-STORJOHANN, A. BEZERRA, R. M. SEGOVIA, J. F. O. GIRRESER, U. KANZAKI, I. TASDEMIR, D. Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| description |
Vatairea guianenis Aubl. (Fabaceae) is an Amazonian medicinal plant species traditionally used for treating skin diseases. In an initial screening, a V. guianensis leaf extract and its subextracts showed antibacterial and antifungal activities. The EtOAc subextract was selected for chemical workup and afforded five known (1-4 and 8) and six undescribed isoflavones, vatairenones C-H( 5-7 and 9-11). All isoflavones are prenylated in position C-8, displaying either chain-prenylated (1-7) or ring-closed forms (8-11). The most bioactive compound (3) exhibited in vitro activity against clinically relevant bacteria and fungi with IC50 values ranging from 6.8 to 26.9 μM. Due to its broad antimicrobial activity and low general toxicity, compound 3 is a potential lead compound for structural modifications. The results of the present study support the ethnomedicinal use of V. guianensis in the treatment of dermatological disorders. 1H NMR spectra of some of the isolated compounds showed intricate signal patterns, which might explain repeated errors in assigning the correct structure of the isoflavonoid B-ring in the literature and which we resolved by higher order spectra simulations. |
| author2 |
SERHAT S. ÇIÇEK, KIEL UNIVERSITY; MAYRA GALARZA PÉREZ, KIEL UNIVERSITY; ARLETTE WENZEL-STORJOHANN, GEOMAR; ROBERTO M. BEZERRA, UNIFAP; JORGE FEDERICO ORELLANA SEGOVIA, CPAF-AP; ULRICH GIRRESER, KIEL UNIVERSITY; ISAMU KANZAKI, UNB; DENIZ TASDEMIR, GEOMAR. |
| author_facet |
SERHAT S. ÇIÇEK, KIEL UNIVERSITY; MAYRA GALARZA PÉREZ, KIEL UNIVERSITY; ARLETTE WENZEL-STORJOHANN, GEOMAR; ROBERTO M. BEZERRA, UNIFAP; JORGE FEDERICO ORELLANA SEGOVIA, CPAF-AP; ULRICH GIRRESER, KIEL UNIVERSITY; ISAMU KANZAKI, UNB; DENIZ TASDEMIR, GEOMAR. ÇIÇEK, S. S. PÉREZ, M. G WENZEL-STORJOHANN, A. BEZERRA, R. M. SEGOVIA, J. F. O. GIRRESER, U. KANZAKI, I. TASDEMIR, D. |
| format |
Artigo de periódico |
| topic_facet |
Planta Medicinal Fabaceae Medicinal plants |
| author |
ÇIÇEK, S. S. PÉREZ, M. G WENZEL-STORJOHANN, A. BEZERRA, R. M. SEGOVIA, J. F. O. GIRRESER, U. KANZAKI, I. TASDEMIR, D. |
| author_sort |
ÇIÇEK, S. S. |
| title |
Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| title_short |
Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| title_full |
Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| title_fullStr |
Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| title_full_unstemmed |
Antimicrobial prenylated isoflavones from the leaves of the Amazonian medicinal plant vatairea guianensis Aubl. |
| title_sort |
antimicrobial prenylated isoflavones from the leaves of the amazonian medicinal plant vatairea guianensis aubl. |
| publishDate |
2022-07-29 |
| url |
http://www.alice.cnptia.embrapa.br/alice/handle/doc/1145058 https://doi.org/10.1021/acs.jnatprod.1c01035 |
| work_keys_str_mv |
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| _version_ |
1756028496558161920 |