Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity

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1. Verfasser: Ana Maria G.A. Tozzi
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Veröffentlicht: Academia Brasileira de Ciências 2007
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author Ana Maria G.A. Tozzi
author_facet Ana Maria G.A. Tozzi
contents Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity Ana Maria G.A. Tozzi Miriam Sannomiya Mary A.F. Perez Aderbal F. Magalhães Eva G. Magalhães Maria Del Pilar C. Soriano Multidisciplinaria (Ciencias Naturales y Exactas) Azevedo flavones flavonoids Leguminosae benzophenone The analysis of root extracts from Lonchocarpus montanus A.M.G. Azevedo resulted in the isolationof twenty three compounds chiefly flavonoids of which five (four flavonoids and one benzophenone)are described for the first time. The molecular structures of the new compounds (1-5) were determinedthrough spectral analysis (UV, IR, MS and NMR) as being: 2´-methoxy-8-(α,α-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3´,4´)-dibenzoylmethane (1), 2´-methoxy-8-(α, α-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3´,4´)-dibenzoylmethane (2), 4´-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-flavone (3), 2"-(1-hydroxy-1-methylethyl)-furano-(4",5":8,7)-flavone (4) and [2´-methoxy-furano-(4",5":3´,4´)-phenyl]-phenylmethanone (5). Additionally, fifteen fatty acids were detected through GC-MS analysis of thecorresponding methyl esters [(CH3)2CH(CH2)8COOH and CH3(CH2)nCOOH (n = 6, 12-24)]. QuantitativeRP-HPLC showed that the most abundant flavonoids in the petroleum ether and dichloromethaneextracts were pongamol (19%) and lanceolatine B (8.0%), respectively. In the bioautography assay, theextracts, pongamol (9), lanceolatine B (10), isolonchocarpin (14), derriobtusone A (17) and medicarpine(18) were active against Staphilococus aureus whereas 9 also against Bacillus subtilis and Cladosporiumcladosporioides. Compound 1, 2",2"-dimethylpyrano-(5",6":8,7)-flavone (11) and furano-(12",13":7,8)-4"-methoxy flavone (12) were active against Fusarium oxysporium whereas 11 also against Rhizopus orizae.The extracts, compounds 9, 10, 17 and (E)-7-O-methoxypongamol (23) displayed high toxicity in the brineshrimp lethality assay. 2007 artículo científico 0001-3765 https://www.redalyc.org/articulo.oa?id=32779301 en http://www.redalyc.org/revista.oa?id=327 Anais da Academia Brasileira de Ciências application/pdf Academia Brasileira de Ciências Anais da Academia Brasileira de Ciências (Brasil) Num.3 Vol.79
format Artículo científico
id redalyc_32779301
institution Redalyc
language en
publishDate 2007
publisher Academia Brasileira de Ciências
spellingShingle Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity
Ana Maria G.A. Tozzi
Multidisciplinaria (Ciencias Naturales y Exactas)
Azevedo
flavones
flavonoids
Leguminosae
benzophenone
Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity Ana Maria G.A. Tozzi Miriam Sannomiya Mary A.F. Perez Aderbal F. Magalhães Eva G. Magalhães Maria Del Pilar C. Soriano Multidisciplinaria (Ciencias Naturales y Exactas) Azevedo flavones flavonoids Leguminosae benzophenone The analysis of root extracts from Lonchocarpus montanus A.M.G. Azevedo resulted in the isolationof twenty three compounds chiefly flavonoids of which five (four flavonoids and one benzophenone)are described for the first time. The molecular structures of the new compounds (1-5) were determinedthrough spectral analysis (UV, IR, MS and NMR) as being: 2´-methoxy-8-(α,α-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3´,4´)-dibenzoylmethane (1), 2´-methoxy-8-(α, α-dimethylallyl)-2", 2"-dimethylpyrano-(5",6":3´,4´)-dibenzoylmethane (2), 4´-methoxy-2",2"-dimethylpyrano-(5",6":8,7)-flavone (3), 2"-(1-hydroxy-1-methylethyl)-furano-(4",5":8,7)-flavone (4) and [2´-methoxy-furano-(4",5":3´,4´)-phenyl]-phenylmethanone (5). Additionally, fifteen fatty acids were detected through GC-MS analysis of thecorresponding methyl esters [(CH3)2CH(CH2)8COOH and CH3(CH2)nCOOH (n = 6, 12-24)]. QuantitativeRP-HPLC showed that the most abundant flavonoids in the petroleum ether and dichloromethaneextracts were pongamol (19%) and lanceolatine B (8.0%), respectively. In the bioautography assay, theextracts, pongamol (9), lanceolatine B (10), isolonchocarpin (14), derriobtusone A (17) and medicarpine(18) were active against Staphilococus aureus whereas 9 also against Bacillus subtilis and Cladosporiumcladosporioides. Compound 1, 2",2"-dimethylpyrano-(5",6":8,7)-flavone (11) and furano-(12",13":7,8)-4"-methoxy flavone (12) were active against Fusarium oxysporium whereas 11 also against Rhizopus orizae.The extracts, compounds 9, 10, 17 and (E)-7-O-methoxypongamol (23) displayed high toxicity in the brineshrimp lethality assay. 2007 artículo científico 0001-3765 https://www.redalyc.org/articulo.oa?id=32779301 en http://www.redalyc.org/revista.oa?id=327 Anais da Academia Brasileira de Ciências application/pdf Academia Brasileira de Ciências Anais da Academia Brasileira de Ciências (Brasil) Num.3 Vol.79
title Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity
topic Multidisciplinaria (Ciencias Naturales y Exactas)
Azevedo
flavones
flavonoids
Leguminosae
benzophenone
url https://www.redalyc.org/articulo.oa?id=32779301