RESUMO
The fungal culture, Mucor ramannianus (ATCC 2628) transformed hesperitin (1) to four metabolites: 4'-methoxy-5,7,8,3'-tetrahydroxyflavanone (8-hydroxyhesperetin) (2), 5,7,3',4'-tetrahydroxyflavanone (eriodictyol) (3), 4'-methoxy-5,3'-dihydroxyflavanone 7-sulfate (hesperetin 7-sulfate) (4) and 5,7,3'-trihydroxyflavanone 4'-O-α-quinovopyranoside (eriodictyol 4'-O-α-quinovopyranoside) (5). The structures were established by spectroscopic methods.
Assuntos
Antineoplásicos/metabolismo , Antioxidantes/metabolismo , Hesperidina/metabolismo , Mucor/metabolismo , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Fermentação , Flavanonas/química , Flavanonas/metabolismo , Hesperidina/química , Hesperidina/isolamento & purificação , Hesperidina/farmacologia , Estrutura Molecular , Mucor/químicaRESUMO
The yeast culture, Rhodotorula mucilaginosa (ATCC 20129) transformed flutamide (1) to three metabolites: 4-nitro-3-(trifluoromethyl)aniline (2), 2-methyl-N-[4-amino-3-(trifloromethyl)phenyl]propanamide (3) and N-[4-amino-3-(trifluoromethyl)phenyl]acetamide (4). The structures were established by spectroscopic methods.
Assuntos
Antineoplásicos Hormonais/metabolismo , Flutamida/metabolismo , Rhodotorula/metabolismo , Antineoplásicos Hormonais/química , Flutamida/química , Humanos , Estrutura Molecular , Rhodotorula/químicaRESUMO
Nine new tetranorditerpenoid dilactones (2-10), together with two previously reported norditerpenoids dilactones (1, 11), and two known putative biosynthetic intermediates, oidiolactone-E (12) and 13, were isolated from an ethyl acetate extract of a culture medium of Sclerotinia homoeocarpa. Structures and absolute configurations of these compounds were determined by spectroscopic methods and confirmed by X-ray crystallographic analysis of representative compounds. Compounds were evaluated for herbicidal, antiplasmodial, and cytotoxic activities. Compounds 1, 2, 6, 7, and 11 were more active as growth inhibitors in a duckweed bioassay (I(50) values of 0.39-0.95 microM) than more than half of 26 commercial herbicides previously evaluated using the same bioassay. Some of these compounds exhibited strong antiplasmodial activities as well, but they also had cytotoxic activity, thus precluding them as potential antimalarial agents.
Assuntos
Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Ascomicetos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Plasmodium falciparum/efeitos dos fármacos , Poaceae/microbiologia , Antimaláricos/química , Antimaláricos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Cristalografia por Raios X , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Mississippi , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
Microbial transformation of the cancer chemopreventive agent, decursin (1) with Sepedonium chrysospermem (ATCC 13378) yielded two metabolites, (+)-decursinol (2) and (-)-cis-decursidinol (3). The structures were established by spectroscopic data.
Assuntos
Anticarcinógenos/farmacologia , Benzopiranos/farmacologia , Butiratos/farmacologia , Hypocreales/efeitos dos fármacos , Redes e Vias Metabólicas/efeitos dos fármacos , Piranocumarinas/farmacologia , Células Cultivadas , Hypocreales/metabolismo , Redes e Vias Metabólicas/fisiologia , Análise Espectral , EstereoisomerismoRESUMO
Microbial metabolism of the cancer chemopreventive agent, curcumin [(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione] (1) with Pichia anomala (ATCC 20170) yielded four major metabolites, 5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3-one (2), 5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)heptan-3-one (3), 1,7-bis(4-hydroxy-3-methoxyphenyl)heptan-3,5-diol (4), 5-hydroxy-1,7-bis(4-hydroxyphenyl)heptane-3-one (5) and two minor products, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptane-3,5-diol (6) and 1,7-bis(4-hydroxyphenyl)heptane-3,5-diol (7). The structures of compounds 2-5 were established on the basis of spectroscopic data. Compounds 6 and 7 were assigned tentative structures.
Assuntos
Curcumina/metabolismo , Pichia/metabolismo , Curcumina/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
Microbial transformation of xanthohumol using the culture broth of Cunninghamella echinulata NRRL 3655 afforded (2S)-8-[4"-hydroxy-3"-methyl-(2"-Z)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (5) and (2S)-8-[5"-hydroxy-3"-methyl-(2"-E)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (6). Xanthohumol (1) and flavanone 6 as well as (E)-2"-(2"'-hydroxyisopropyl)-dihydrofurano[2",3":4',3']-2',4-dihydroxy-6'-methoxychalcone (2), (2S)-2"-(2"'-hydroxyisopropyl)-dihydrofurano[2",3":7,8]-4'-hydroxy-5-methoxyflavanone (3) obtained with Pichia membranifaciens showed antimalarial activity against Plasmodium falciparum.