Karina Fraige1, Alessandra Cristina Dametto1, Maria Luiza Zeraik1,2, Larissa de Freitas1, Amanda Correia Saraiva3, Alexandra Ivo Medeiros3, Ian Castro-Gamboa1, Alberto José Cavalheiro1, Dulce Helena S Silva1, Norberto Peporine Lopes4, Vanderlan S Bolzani1. 1. Departamento de Química Orgânica, Instituto de Química de Araraquara, Núcleo de Bioensaios, Biossíntese e Ecofisiologia de Produtos Naturais (NUBBE), Universidade Estadual Paulista Júlio de Mesquita Filho (UNESP), 14800-900, Araraquara, SP, Brazil. 2. Departamento de Química, Universidade Estadual de Londrina (UEL), 86051-990, Londrina, PR, Brazil. 3. Departamento de Ciências Biológicas, Universidade Estadual Paulista (UNESP), Faculdade de Ciências Farmacêuticas, Araraquara, 14800-903, Araraquara, SP, Brazil. 4. Departamento de Física e Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Núcleo de Pesquisa em Produtos Naturais e Sintéticos (NPPNS), Universidade de São Paulo (USP), 14040-903, Ribeirão Preto, Brazil.
Abstract
INTRODUCTION: Byrsonima species have been used in the treatment of gastrointestinal and gynecological inflammations, skin infections and snakebites. Based on their biological activities, it is important to study other organisms from this genus and to identify their metabolites. OBJECTIVES: To determine the metabolic fingerprinting of methanol and ethyl acetate extracts of four Byrsonima species (B. intermedia, B. coccolobifolia, B. verbascifolia and B. sericea) by HPLC-DAD-ESI-MS/MS and evaluate their in vitro antioxidant, anti-glycation, anti-inflammatory and cytotoxic activities. MATERIALS AND METHODS: Antioxidant activity was determined by DPPH˙, ABTS˙+ and ROO˙ scavenging assays. Anti-glycation activity was evaluated by the ability to inhibit the formation of advanced glycation endproducts (AGEs). Anti-inflammatory activity was evaluated using a murine macrophage cell line (RAW 264-7) in the presence of lipopolysaccharide (LPS). Tumour necrosis factor alpha (TNF-α) and nitrite (NO2- ) production were measured by ELISA and the Griess reaction, respectively. The compounds present in the extracts were tentatively identified by HPLC-DAD-ESI-MS/MS. RESULTS: The evaluation of the biological activities showed the potential of the extracts. The activities were assigned to the presence of glycoside flavonoids mainly derived from quercetin, quinic acid derivatives, gallic acid derivatives, galloylquinic acids and proanthocyanidins. Two isomers of sinapic acid-O-hexoside were described for the first time in a Byrsonima species. CONCLUSION: This research contributes to the study of the genus, it is the first report of the chemical composition of B. sericea and demonstrates the importance of the dereplication process, allowing the identification of known compounds without time-consuming procedures.
INTRODUCTION: Byrsonima species have been used in the treatment of gastrointestinal and gynecological inflammations, skin infections and snakebites. Based on their biological activities, it is important to study other organisms from this genus and to identify their metabolites. OBJECTIVES: To determine the metabolic fingerprinting of methanol and ethyl acetate extracts of four Byrsonima species (B. intermedia, B. coccolobifolia, B. verbascifolia and B. sericea) by HPLC-DAD-ESI-MS/MS and evaluate their in vitro antioxidant, anti-glycation, anti-inflammatory and cytotoxic activities. MATERIALS AND METHODS: Antioxidant activity was determined by DPPH˙, ABTS˙+ and ROO˙ scavenging assays. Anti-glycation activity was evaluated by the ability to inhibit the formation of advanced glycation endproducts (AGEs). Anti-inflammatory activity was evaluated using a murine macrophage cell line (RAW 264-7) in the presence of lipopolysaccharide (LPS). Tumour necrosis factor alpha (TNF-α) and nitrite (NO2- ) production were measured by ELISA and the Griess reaction, respectively. The compounds present in the extracts were tentatively identified by HPLC-DAD-ESI-MS/MS. RESULTS: The evaluation of the biological activities showed the potential of the extracts. The activities were assigned to the presence of glycosideflavonoids mainly derived from quercetin, quinic acid derivatives, gallic acid derivatives, galloylquinic acids and proanthocyanidins. Two isomers of sinapic acid-O-hexoside were described for the first time in a Byrsonima species. CONCLUSION: This research contributes to the study of the genus, it is the first report of the chemical composition of B. sericea and demonstrates the importance of the dereplication process, allowing the identification of known compounds without time-consuming procedures.
Authors: Helena Mannochio-Russo; Rafael F de Almeida; Wilhan D G Nunes; Paula C P Bueno; Andrés M Caraballo-Rodríguez; Anelize Bauermeister; Pieter C Dorrestein; Vanderlan S Bolzani Journal: Front Plant Sci Date: 2022-04-14 Impact factor: 5.753
Authors: Lucas Silva Abreu; Iura Muniz Alves; Renan Fernandes do Espírito Santo; Yuri Mangueira do Nascimento; César Augusto Gonçalves Dantas; Gisele Graça Leite Dos Santos; Mireille Le Hyaric; Maria Lenise Silva Guedes; Marcelo Sobral da Silva; Cristiane Flora Villarreal; Eudes da Silva Velozo; Josean Fechine Tavares Journal: PLoS One Date: 2019-10-29 Impact factor: 3.240