RESUMO
Coptidis rhizome (CR) is a widely used herbal medicine that contains protoberberine-type alkaloids. CR extract exhibits various pharmacologic activities. A previous study reported the isolation of Rhodococcus sp. strain BD7100 as a berberine (BBR)-utilizing bacterium, and the BBR-degradation pathway has been investigated. When we incubated strain BD7100 cells with CR extract, the number of viable cells declined with the degradation of components in the CR extract, and the culture broth exhibited antibacterial activity against strain BD7100. These results suggest that CR extract cultured in the presence of strain BD7100 contains one or more antibacterial agents. In this study, we isolated coptirhoquinone A (1) from CR extract incubated with strain BD7100 in Luria-Bertani (LB) medium, and the structure was elucidated using NMR and MS analysis. We also report the total synthesis and antimicrobial activities of 1 against bacteria, fungi, and Pythium sp.
Assuntos
Antibacterianos/farmacologia , Medicamentos de Ervas Chinesas/farmacologia , Rhodococcus/crescimento & desenvolvimento , Rhodococcus/metabolismo , Antibacterianos/química , Antifúngicos/farmacologia , Antiprotozoários/farmacologia , Berberina/metabolismo , Coptis chinensis , Medicamentos de Ervas Chinesas/química , Fungos/efeitos dos fármacos , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Pythium/efeitos dos fármacos , Quinonas/química , Quinonas/isolamento & purificação , Quinonas/farmacologia , Rhodococcus/efeitos dos fármacosRESUMO
A new cinnamoylphenethylamine derivative, compound 1, was isolated as the main HPLC peak after partitioning the methanol extract of bulbs of a Mongolian onion species, Allium carolinianum DC. The chemical structure of this substance was determined by spectroscopic analysis including MS, and 1D and 2D NMR. Compound 1 showed weak cytotoxic activity in the murine leukemia cell line P388.
Assuntos
Allium/química , Fenetilaminas/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Mongólia , Fenetilaminas/química , Extratos Vegetais/química , Raízes de Plantas/químicaRESUMO
Protoberberine alkaloids, including berberine, palmatine, and berberrubine, are produced by medicinal plants and are known to have various pharmacological effects. We isolated two berberine-utilizing bacteria, Sphingobium sp. strain BD3100 and Rhodococcus sp. strain BD7100, from soil collected at a natural medicine factory. BD3100 had the unique ability to utilize berberine or palmatine as the sole carbon and energy source. BD3100 produced demethyleneberberine in berberine-supplemented medium. In a resting-cell incubation with berberine, BD3100 produced 11-hydroxyberberine; the structure of 11-hydroxyberberine was determined by detailed analysis of NMR and MS spectroscopic data. α-Naphthoflavone, miconazole, and ketoconazole, which are known inhibitors of cytochrome P450, interfered with BD3100 metabolism of berberine in resting cells. Inhibition by miconazole led to the production of a new compound, 11-hydroxydemethyleneberberine. In a resting-cell incubation with palmatine, BD3100 generated 11-hydroxypalmatine. This work represents the first report of the isolation and characterization of novel berberine-utilizing aerobic bacteria for the production of 11-hydroxylation derivatives of berberine and palmatine.