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Bioorg Med Chem Lett ; 13(24): 4345-50, 2003 Dec 15.
Article in English | MEDLINE | ID: mdl-14643323

ABSTRACT

The less polar fraction of the methanolic extract from the plant Euphorbia peplis L. exhibited interesting antifungal and antitubercular activity. A complex mixture of four glucocerebrosides was responsible for this activity. Two new cerebrosides were isolated for the first time from Euphorbiaceae, 4 was assigned as 1-O-(beta-D-glucopyranosyl)-(2S,3S,4E,8E)-2N-[(2'R)-2'-hydroxy-hexadecanoyl]-4 (E), 8 (E)-octadecadiene-1,3-diol and 3 as the 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R,8Z)-2N-[(2'R)-2'-hydroxytetracosanoyl]-8 (Z)-octadecene-1,3,4-triol. The structures were determined on the basis of chemical and spectroscopic evidences. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond positions in the long-chain bases.


Subject(s)
Anti-Infective Agents/pharmacology , Cerebrosides/pharmacology , Euphorbia/chemistry , Anti-Bacterial Agents/pharmacology , Anti-Infective Agents/isolation & purification , Antifungal Agents/pharmacology , Antitubercular Agents/pharmacology , Bacteria/drug effects , Cerebrosides/chemical synthesis , Cerebrosides/chemistry , Cerebrosides/isolation & purification , Euphorbiaceae/chemistry , Fungi/drug effects , Microbial Sensitivity Tests , Models, Molecular , Molecular Structure , Structure-Activity Relationship
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