New cerebrosides from Euphorbia peplis L.: antimicrobial activity evaluation.
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.
Cateni
Francesca
F
Department of Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy. cateni@univ.trieste.it
Zilic
Jelena
J
Falsone
Gioacchino
G
Scialino
Giuditta
G
Banfi
Elena
E
D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000302:isolation & purification / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology; D000995:Antitubercular Agents / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002554:Cerebrosides / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D028481:Euphorbia / Q000737:chemistry*; D019665:Euphorbiaceae / Q000737:chemistry; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000995:Antitubercular Agents; D002554:Cerebrosides