Chemical and Biological Evaluation of Amazonian Medicinal Plant <i>Vouacapoua americana</i> Aubl
Serhat Sezai Çiçek,
Anna Laís Pfeifer Barbosa,
Arlette Wenzel-Storjohann,
Jorge Federico Orellana Segovia,
Roberto Messias Bezerra,
Frank Sönnichsen,
Christian Zidorn,
Isamu Kanzaki,
Deniz Tasdemir
Affiliations
Serhat Sezai Çiçek
Department of Pharmaceutical Biology, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany
Anna Laís Pfeifer Barbosa
Department of Pharmaceutical Biology, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany
Arlette Wenzel-Storjohann
Research Unit Marine Natural Products Chemistry, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
Jorge Federico Orellana Segovia
Ecoregional Research Unit, Brazilian Agricultural Research Corporation, Rod. JK, Km 5, Macapá 68903-419, AP, Brazil
Roberto Messias Bezerra
Laboratory of Bioprospection and Atomic Absorption, Federal University of Amapá, Rod. JK, Macapá 68903-419, AP, Brazil
Frank Sönnichsen
Otto Diels Institute for Organic Chemistry, Kiel University, Otto-Hahn-Platz 4, 24118 Kiel, Germany
Christian Zidorn
Department of Pharmaceutical Biology, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany
Isamu Kanzaki
Laboratory of Bioprospection, Darcy Ribeiro Campus, University of Brasilia, Brasilia 70910-900, DF, Brazil
Deniz Tasdemir
Research Unit Marine Natural Products Chemistry, GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
Vouacapoua americana (Fabaceae) is an economically important tree in the Amazon region and used for its highly resistant heartwood as well as for medicinal purposes. Despite its frequent use, phytochemical investigations have been limited and rather focused on ecological properties than on its pharmacological potential. In this study, we investigated the phytochemistry and bioactivity of V. americana stem bark extract and its constituents to identify eventual lead structures for further drug development. Applying hydrodistillation and subsequent GC-MS analysis, we investigated the composition of the essential oil and identified the 15 most abundant components. Moreover, the diterpenoids deacetylchagresnone (1), cassa-13(14),15-dien-oic acid (2), isoneocaesalpin H (3), (+)-vouacapenic acid (4), and (+)-methyl vouacapenate (5) were isolated from the stem bark, with compounds 2 and 4 showing pronounced effects on Methicillin-resistant Staphylococcus aureus and Enterococcus faecium, respectively. During the structure elucidation of deacetylchagresnone (1), which was isolated from a natural source for the first time, we detected inconsistencies regarding the configuration of the cyclopropane ring. Thus, the structure was revised for both deacetylchagresnone (1) and the previously isolated chagresnone. Following our works on Copaifera reticulata and Vatairea guianensis, the results of this study further contribute to the knowledge of Amazonian medicinal plants.
