2. Academic Validation
  3. Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl

Antimicrobial Prenylated Isoflavones from the Leaves of the Amazonian Medicinal Plant Vatairea guianensis Aubl

  • J Nat Prod. 2022 Apr 22;85(4):927-935. doi: 10.1021/acs.jnatprod.1c01035.
Serhat S Çiçek 1,  Mayra Galarza Pérez 1,  Arlette Wenzel-Storjohann 2,  Roberto M Bezerra 3,  Jorge F O Segovia 4,  Ulrich Girreser 5,  Isamu Kanzaki 6,  Deniz Tasdemir 2 7
Affiliations

Affiliations

  • 1 Department of Pharmaceutical Biology, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany.
  • 2 GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany.
  • 3 Laboratory of Bioprospection and Atomic Absorption, Federal University of Amapá, Rod. JK, Macapá, 68903-419 Amapá, Brazil.
  • 4 Brazilian Agricultural Research Corporation, Ecoregional Research Unit, Rod. JK, Km 5, Macapá, 68903-419 Amapá, Brazil.
  • 5 Department of Pharmaceutical and Medicinal Chemistry, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany.
  • 6 Laboratory of Bioprospection, University of Brasilia, Darcy Ribeiro Campus, 70910-900 Brasilia, DF, Brazil.
  • 7 Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany.
PMID: 35271771 DOI: 10.1021/acs.jnatprod.1c01035
Abstract

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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