Phytochemical analysis of leguminosas : Harleyodendron Unifoliolatum Cowan e Holocalyx Balansae Micheli. Isolation, structural elucidation and biological activities

Abstract

O estudo fitoquímico dos extratos das raízes de Harleyodendron unifoliolatum e de Holocalyx balansae, ambas pertencentes à família Leguminosae, resultou no isolamento de 9 isoflavonóides (4 pterocarpanos, 2 isoflavanas e 3 isoflavanonas) e um fitoesteróide sendo que 7 isoflavonóides são descritos pela primeira vez. As estruturas moleculares foram elucidadas através de análises espectrais (UV, IV, RMN e EMAR) na qual a espectroscopia RMN foi explorada através de RMN H, RMN C (incluindo DEPT 90° e 135°), RMN-2D (gCOSY, HSQC, gHMBC) e experimentos NOESY-1D. A atividade antimicrobiana dos isoflavonóides (1-9) foi examinada através de bioautografia contra oito espécies de fungos (Alternaria alternata, Aspergillus fumigatus, Aspergillus niger, Candida albicans, Cladosporium cladosporioides, Fusarium oxysporum, Penicillium funiculosum e Rhizopus oryzae) e seis espécies de bactérias (Bacillus subtilis, Escherichia coli, Micrococcus luteus, Salmonella tiphymurium, Staphilococcus aureus e Streptococcus mutans), em que encontrou-se que 1 foi ativo contra os fungos Alternaria alternata e Penicillium funiculosum; 2 foi ativo contra a bactéria Escherichia coli e contra o fungo Aspergillus niger; 3 e 6 foram ativos contra a bactéria Bacillus subtilis e os fungos Aspergillus fumigatus e Rizophus orizae; 5 e 7 foram ativos contra as bactérias Bacillus subtilis e Staphilococcus aureus e o fungo Penicillium funiculosum. O perfil flavonoídico fornecido pelas espécies analisadas neste trabalho corrobora com sua alocação na tribo Swartzieae, como foi recentemente proposto por A.M.G.A. Tozzi baseado em morfologia.The phytochemical study of roots extracts from Harleyodendron unifoliolatum and Holocalyx balansae, both belonging to the family Leguminosae, resulted in the isolation of nine isoflavonoids (four pterocarpans, two isoflavans and three isoflavanones) and one phytosteroid being that seven isoflavonoids are now described for the first time. The molecular structures were elucidated through spectra analysis (UV, IV, NMR and HREIMS) when NMR spectroscopy was explored trough H NMR, C NMR (including DEPT 90° and 135°), 2D-NMR (gCOSY, HSQC, gHMBC) and NOESY-1D experiments. The antimicrobial activity of the isoflavonoids (1-9) was screened through bioautography against eight species of fungi (Alternaria alternata, Aspergillus fumigatus, Aspergillus niger, Candida albicans, Cladosporium cladosporioides, Fusarium oxysporum, Penicillium funiculosum and Rhizopus orizae) and six species of bacteria (Bacillus subtilis, Escherichia coli, Micrococcus Iuteus, SalmoneIla tiphymurium, Staphilococcus aureus and Streptococcus mutans), when it was found that 1 was active against fungi Alternaria alternata and Penicillium funiculosum; 2 was active against bacteria Escherichia coli and fungus Aspergillus niger; 3 and 6 were active against bacteria Bacillus subtilis and fungi Aspergillus fumigatus and Rizophus orizae, 5 and 7 was active against bacteria Bacillus subtilis and Staphilococcus aureus and fungus Penicillium funiculosum. The flavonoid profile furnished by the plant species analysed in this work corroborate with their allocation in the tribe Swartizieae as it has been recently propose by A.M.G.A. Tozzi based on morphology