New isoflavones from the leaves of Vatairea guianensis Aublé

SOUZA, Ronilson Freitas de; MARINHO, Victor Hugo de Souza; SILVA, Geilson Alcantara da; COSTA JUNIOR, Livio Martins; SILVA, Joyce Kelly do Rosário da; BASTOS, Gilmara de Nazareth Tavares; ARRUDA, Alberto Cardoso; SILVA, Milton Nascimento da; ARRUDA, Mara Silvia Pinheiro

Artigo

New isoflavones from the leaves of Vatairea guianensis Aublé

Four isoflavones were isolated from Vatairea guianensis Aublé leaves and identified as 5,3'-dihydroxy-4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-isoflavone ( 1: ), 5,7-dihydroxy-3',4'-methylenedioxy-8-prenyl-isoflavone ( 2: ), 5,3'-dihydroxy-4'-methoxy-7-O-β-glucopyranoside-8-prenyl-isoflavone ( 3:...

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Autor principal:	SOUZA, Ronilson Freitas de
Outros Autores:	MARINHO, Victor Hugo de Souza, SILVA, Geilson Alcantara da, COSTA JUNIOR, Livio Martins, SILVA, Joyce Kelly do Rosário da, BASTOS, Gilmara de Nazareth Tavares, ARRUDA, Alberto Cardoso, SILVA, Milton Nascimento da, ARRUDA, Mara Silvia Pinheiro
Grau:	Artigo
Idioma:	eng
Publicado em:	2015
Assuntos:	Atividade antioxidante Vatairea guianensis Isoflavonas DPPH• Fabaceae Fava bolacha Belém - PA Pará - Estado Amazônia brasileira
Acesso em linha:	http://repositorio.ufpa.br/jspui/handle/2011/6293

id	ir-2011-6293
recordtype	dspace
spelling	ir-2011-62932019-05-23T13:25:55Z New isoflavones from the leaves of Vatairea guianensis Aublé SOUZA, Ronilson Freitas de MARINHO, Victor Hugo de Souza SILVA, Geilson Alcantara da COSTA JUNIOR, Livio Martins SILVA, Joyce Kelly do Rosário da BASTOS, Gilmara de Nazareth Tavares ARRUDA, Alberto Cardoso SILVA, Milton Nascimento da ARRUDA, Mara Silvia Pinheiro Atividade antioxidante Vatairea guianensis Isoflavonas DPPH• Fabaceae Fava bolacha Belém - PA Pará - Estado Amazônia brasileira Four isoflavones were isolated from Vatairea guianensis Aublé leaves and identified as 5,3'-dihydroxy-4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-isoflavone ( 1: ), 5,7-dihydroxy-3',4'-methylenedioxy-8-prenyl-isoflavone ( 2: ), 5,3'-dihydroxy-4'-methoxy-7-O-β-glucopyranoside-8-prenyl-isoflavone ( 3: ) and derrone ( 4: ) together with five triterpenes identified in mixture, lupeol, α-amyrin, β-amyrin, germanicol and betulinic acid. Substances 1: 3: are novel natural products, although 1: and 2: have been cited as synthetic products. However, all these compounds are first reported from this species. Their chemical structures were elucidated based on their 1D and 2D nuclear magnetic resonance (NMR) data and high resolution mass spectrometry. The ethanol extract from the leaves and 1: 3: were evaluated for their potential in scavenging DPPH• (2,2-diphenyl-1-picrylhydrazylradical) and the results showed that the extract presented high activity (IC50 = 6.2 ± 0.4 µg mL-1), while the isolated compounds showed low antioxidant power (IC50 ≥ 29.5 ± 2.5 µg mL-1) when compared to Trolox (IC50 = 4.5 ± 0.4 µg mL-1). Das folhas de Vatairea guianensis Aublé foram isoladas quatro isoflavonas identificadas como, 5,3',-diidroxi-4'-metoxi-2",2"-dimetilpirano-(5",6":8,7)-isoflavona ( 1: ), 5,7-diidroxi-3',4'-metilenodioxi-8-prenil-isoflavona ( 2: ) e 5,3'-diidroxi-4'-metoxi-7-O-β-glicopiranosídeo-8-prenil-isoflavona ( 3: ) e derrona ( 4: ), juntamente com cinco triterpenos identificados em mistura de lupeol, α-amirina, β-amirina, germanicol e ácido betulínico. As substâncias 1: 3: são novos produtos naturais, porém 1: e 2: já foram citados como produtos de síntese. No entanto, todas essas substâncias são relatadas pela primeira vez para essa espécie. Suas estruturas químicas foram elucidadas com base nos seus dados de ressonância magnética nuclear (RMN) 1D e 2D e por espectrometria de massas de alta resolução. O extrato etanólico das folhas e os compostos 1-3: foram avaliados quanto ao seu potencial sequestrador do radical DPPH• (2,2-difenil-1-picril-hidrazila) e os resultados mostram que o extrato apresentou alta atividade (CI50 = 6,2 ± 0,4 µg mL-1), enquanto as substâncias testadas apresentaram baixo poder antioxidante (CI50 ≥ 29,5 ± 2,5 µg mL-1) quando comparadas com TROLOX (CI50 = 4,5 ± 0,4 µg mL-1). 2015-02-09T13:25:06Z 2015-02-09T13:25:06Z 2013-11 Artigo de Periódico SOUZA, Ronilson Freitas de et al. New isoflavones from the leaves of Vatairea guianensis Aublé. Journal of the Brazilian Chemical Society, São Paulo, v. 24, n. 11, p. 1857-863, nov. 2013. Disponível em: <http://www.scielo.br/pdf/jbchs/v24n11/18.pdf>. Acesso em: 06 fev. 2015. <http://dx.doi.org/10.5935/0103-53.20130231>. 0103-5053 http://repositorio.ufpa.br/jspui/handle/2011/6293 eng Acesso Aberto application/pdf
institution	Repositório Institucional - Universidade Federal do Pará
collection	RI-UFPA
language	eng
topic	Atividade antioxidante Vatairea guianensis Isoflavonas DPPH• Fabaceae Fava bolacha Belém - PA Pará - Estado Amazônia brasileira
spellingShingle	Atividade antioxidante Vatairea guianensis Isoflavonas DPPH• Fabaceae Fava bolacha Belém - PA Pará - Estado Amazônia brasileira SOUZA, Ronilson Freitas de New isoflavones from the leaves of Vatairea guianensis Aublé
topic_facet	Atividade antioxidante Vatairea guianensis Isoflavonas DPPH• Fabaceae Fava bolacha Belém - PA Pará - Estado Amazônia brasileira
description	Four isoflavones were isolated from Vatairea guianensis Aublé leaves and identified as 5,3'-dihydroxy-4'-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-isoflavone ( 1: ), 5,7-dihydroxy-3',4'-methylenedioxy-8-prenyl-isoflavone ( 2: ), 5,3'-dihydroxy-4'-methoxy-7-O-β-glucopyranoside-8-prenyl-isoflavone ( 3: ) and derrone ( 4: ) together with five triterpenes identified in mixture, lupeol, α-amyrin, β-amyrin, germanicol and betulinic acid. Substances 1: 3: are novel natural products, although 1: and 2: have been cited as synthetic products. However, all these compounds are first reported from this species. Their chemical structures were elucidated based on their 1D and 2D nuclear magnetic resonance (NMR) data and high resolution mass spectrometry. The ethanol extract from the leaves and 1: 3: were evaluated for their potential in scavenging DPPH• (2,2-diphenyl-1-picrylhydrazylradical) and the results showed that the extract presented high activity (IC50 = 6.2 ± 0.4 µg mL-1), while the isolated compounds showed low antioxidant power (IC50 ≥ 29.5 ± 2.5 µg mL-1) when compared to Trolox (IC50 = 4.5 ± 0.4 µg mL-1).
format	Artigo
author	SOUZA, Ronilson Freitas de
author2	MARINHO, Victor Hugo de Souza SILVA, Geilson Alcantara da COSTA JUNIOR, Livio Martins SILVA, Joyce Kelly do Rosário da BASTOS, Gilmara de Nazareth Tavares ARRUDA, Alberto Cardoso SILVA, Milton Nascimento da ARRUDA, Mara Silvia Pinheiro
author2Str	MARINHO, Victor Hugo de Souza SILVA, Geilson Alcantara da COSTA JUNIOR, Livio Martins SILVA, Joyce Kelly do Rosário da BASTOS, Gilmara de Nazareth Tavares ARRUDA, Alberto Cardoso SILVA, Milton Nascimento da ARRUDA, Mara Silvia Pinheiro
title	New isoflavones from the leaves of Vatairea guianensis Aublé
title_short	New isoflavones from the leaves of Vatairea guianensis Aublé
title_full	New isoflavones from the leaves of Vatairea guianensis Aublé
title_fullStr	New isoflavones from the leaves of Vatairea guianensis Aublé
title_full_unstemmed	New isoflavones from the leaves of Vatairea guianensis Aublé
title_sort	new isoflavones from the leaves of vatairea guianensis aublé
publishDate	2015
url	http://repositorio.ufpa.br/jspui/handle/2011/6293
_version_	1832605192502116352
score	11.755432

New isoflavones from the leaves of Vatairea guianensis Aublé

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