Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity

• Published in: Journal of ethnopharmacology Vol. 297; p. 115534
• Main Authors: Sannomiya, Miriam, Rodrigues, Clenilson Martins, Oliveira, Giovanna Castro Araújo, Carvalho, Juliana Cajado Souza, da Costa, Letícia Serafim, Spadari, Cristina de Castro, Ferreira, Marcelo José Pena, Vilegas, Wagner, Ishida, Kelly
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 28.10.2022
• Subjects: Antifungal; Cryptococcosis; Cryptococcus; Gallotannins; Galloylquinic acids; Malpighiaceae; Murici; Quercetin derivatives; Antifungal; Galloylquinic acids; Cryptococcosis; Gallotannins; Cryptococcus; Malpighiaceae; Quercetin derivatives; Murici
• ISSN: 0378-8741; 1872-7573
• DOI: 10.1016/j.jep.2022.115534

Byrsonima fagifolia Niedenzu (Malpighiaceae) and other Byrsonima species are popularly employed in Brazilian traditional medicine in the form of preparations as cicatrizing, anti-inflammatory, and antimicrobial. To characterize the phytochemical profile of the hydromethanolic extract obtained from B. fagifolia leaves (BF extract) and to evaluate the toxicity and the antifungal activity. The compounds from BF extract were isolated by HPLC and the structures were elucidated based on extensive analyses of 1D and 2D NMR spectra (HMQC, HMBC and COSY) data. The antifungal effect was determined by the broth microdilution method and the toxicity was evaluated on erythrocytes from sheep’s blood and Galleria mellonella larvae. Phytochemical investigation of the BF extract led to the isolation and characterization of pyrogallol, n-butyl gallate, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, and 1,3,4,5-tetra-O-galloylquinic acid. The BF extract showed high content of galloylquinic acid derivatives reaching more than twenty-times the quercetin derivatives content, according to the quantification by HPLC. These galloylquinic acid derivatives, obtained during this study, and quercetin derivatives, previously isolated, were submitted to the antifungal assays. The BF extract inhibited yeast growth mainly against Cryptococcus spp., at concentrations of 1–16 μg/mL, comparable to isolated compounds galloylquinic acid derivatives. However, the quercetin derivatives as well as quinic acid, gallic acid, and methyl gallate showed lower antifungal effect compared with galloylquinic derivatives. In addition, the BF extract had no hemolytic effect and no toxicity on G. mellonella. The phytochemical analysis revealed that galloylquinic acid derivatives are the major compounds in the leaves of B. fagifolia and they are associated to anti-cryptococcal activity and presented reduced toxicity. [Display omitted] •Pyrogallol, n-butyl gallate, and 4 galloylquinic acid derivatives were isolated from Byrsonima fagifolia (BF extract).•High content of galloylquinic acid derivatives was determined in the BF extract.•The galloylquinic acid derivatives were associated with the antifungal activity against Cryptococcus spp.