RESUMO
In situ C-C bond cleavage of vicinal diol following by the lactolisation resulted from separated treatment of Arjunolic acid (1), 24-hydroxytormentic acid (2) and 3-O-ß-D-glucopyranosylsitosterol (3) with sodium periodate and silica gel in dried THF according to the strategic position of hydroxyl functions in the molecule. The reaction led to a lactol pentacyclic triterpenes 1A, 2A and a bicyclotriacetal of ß-sitosterol 3A. These products were further acetylated and the cytotoxicity of all molecules was evaluated against human fibrosarcoma HT1080 cancer cells lines.
Assuntos
Antineoplásicos/síntese química , Triterpenos/síntese química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Ácido Periódico/química , Dióxido de Silício/química , Triterpenos/químicaRESUMO
In addition to benjaminamide (2), ß-amyrin, ß-amyrin acetate, lupeol, betulinic acid, ß-sitosterol glucoside, a new ceramide glycoside was isolated from the woods of Ficus lutea Vahl (Moraceae). Using mass fragmentation pattern, 1 and 2D NMR spectra and by comparison with published data, the new compound was characterized as 1-O-ß-D-glucopyranosyl-(2S,3R,5E,12E)-2N-[(2'R)-hydroxyhexadecanoyl]-octadecasphinga-5,12-dienine (1a) for which the trivial name lutaoside was proposed. Some isolated compounds were evaluated for their antimicrobial activities. Compounds 1a and 2 showed some antimicrobial activity.
RESUMO
Two new flavonoid glycosides, namely 3'-(2'',4''-dihydroxybenzyloxy)acanthophorin B (1b) and beta,2,3',4,4',6-hexahydroxy-alpha-(alpha-L-rhamnopyranosyl)dihydrochalcone (2) were isolated from the leaves of Psorospermum androsaemifolium together with quercetin (1), acanthophorin B (1a), alpha- (3) and beta-amyrine (3a), vismiaquinone (4), 12-hentriacontanol and hentriacontane. The structures of these secondary metabolites were established using detailed spectroscopic analysis and by comparison with published data. Compounds 1, 1a, 1b, 2, 3, 3a and 4 showed weak antifungal and antibacterial activities.
Assuntos
Chalconas/química , Clusiaceae/química , Flavonas/química , Flavonoides/química , Glicosídeos/química , Ramnose/análogos & derivados , Antibacterianos/farmacologia , Antifúngicos/farmacologia , Chalconas/isolamento & purificação , Chalconas/farmacologia , Flavonas/isolamento & purificação , Flavonas/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Hidrólise , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Folhas de Planta/química , Ramnose/química , Ramnose/isolamento & purificação , Ramnose/farmacologia , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Three new compounds, 15-acetoxy-12-hydroxy-16-methyl-labda-8(17),13E-diene (1), ent-labda-8(17),13-dien-15,16-olid-19-oic acid methyl ester (2), and 12-hydroxy-labda-8(17),13-dien-15,16-olide (3), together with two known compounds, 19-acetoxy-ent-labda-8(17),13-dien-15,16-olide (4), and 16-acetoxy-12,15-epoxy-15beta-hydroxy-labda-8(17),13(16)-diene (5) were isolated from the stem bark of Turraeanthus mannii (Meliaceae). The structures of compounds 1 - 3 were elucidated by analysis of the spectroscopic data. The crude methanol extract and compound 5 exhibited weak antibacterial and antifungal activity.
