A New Homoisoflavonoid from Caesalpinia bahamensis
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A New Homoisoflavonoid from Caesalpinia bahamensis Alejandro Felipe González 1 & Yamilet I. Gutiérrez Gaitén 1 Luc Pieters 2 & René Delgado Hernández 3,4
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Ramón Scull Lizama 1
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Kenn Foubert 2
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Received: 4 August 2020 / Accepted: 24 September 2020 / Published online: 6 October 2020 # Sociedade Brasileira de Farmacognosia 2020
Abstract Homoisoflavonoids constitute a rare subclass of flavonoids restricted to only some plant species, including members of the genus Caesalpinia. This research focused on homoisoflavonoids from Caesalpinia bahamensis Lam., Fabaceae, a medicinal plant used in Cuban traditional medicine and known as “brasilete.” An hydroalcoholic extract was prepared from the stem, followed by liquid-liquid partition and further chromatographic separations, resulting in the isolation and structure elucidation by nuclear magnetic resonance spectroscopy and mass spectrometry of an undescribed 3-(2-hydroxy-4-methoxybenzyl)chromane-4,7-diol, for which the name metasappanin was proposed. Keywords Fabaceae . Isolation . NMR . Sappanin . Structural elucidation
Introduction Homoisoflavonoids are a rare subclass of flavonoids characterized by the presence of sixteen carbons in their general structure containing two phenyl rings and one heterocyclic ring. They are restricted only to some plant species including those from Fabaceae and Asparagaceae. These compounds have been isolated of several species of the genus Caesalpinia, such as, C. pulcherrima, C. echinata, C. bonduc, C. sappan, C. japonica, and C. milletti (Baldim et al. 2017). Biological properties such as antimicrobial, antioxidant, anti-inflammatory, antitumoral,
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s43450-020-00108-3) contains supplementary material, which is available to authorized users. * Luc Pieters [email protected] 1
Departamento de Farmacia, Instituto de Farmacia y Alimentos, Universidad de la Habana, Havana, Cuba
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Natural Products & Food Research and Analysis, Department of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
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Centro de Investigaciones y Evaluaciones Biológicas, Instituto de Farmacia y Alimentos, Universidad de la Habana, Havana, Cuba
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Facultad de Ciencias Exactas, Naturales y Agrarias, Universidad de Santander, Santander, Colombia
hypoglycemic, and hemostatic have been associated with the presence of homoisoflavonoids in the genus Caesalpinia (Zanin et al. 2012). Caesalpinia bahamensis Lam., Fabaceae, is a medicinal plant traditionally used in Cuba to treat renal and hepatic problems, diabetes mellitus, and peptic ulcers (Roig 2012). The diuretic, antioxidant, cytotoxic, and poor antimicrobial activities have been reported previously for this species (Felipe et al. 2011, 2019; Setzer et al. 2015; Abreu et al. 2017). Chemically, seventy-four compounds associated with fatty acids, terpenoids, and phytosterols have been identified for this plant (Felipe et al. 2017). The presence of homoisoflavonoids in C. bahamensis
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