title: [Biotransformation of phenolglycosides leiocarposide and salicin].
abstract: Leiocarposide (1; 3-beta-D-glucopyranosyloxy-2-methoxy-6-hydroxy-benzoic acid -2'-beta-D-glucopyranosyloxybenzyl ester) is a phenolic glycoside from Solidago virgaurea L. After oral administration to rats it will be only poorly absorbed and mostly unchanged fecaly excreted. In the urine were found less than 10% as metabolites: leiocarpic acid (3; 3,6-dihydroxy-2-methoxy-benzoic acid, 2% of the administered dose), 3-conjugates (2%), salicylic acid (5; 0.5%), 5-conjugates (0.1%) and salicyluric acid (6; 0.5%). On the other hand salicin (2), structural part of 1, is good absorbed. In the urine were excreted 15% of the unchanged drug and the following metabolites: 0.1% saligenin (4), 30% 5, 5% 5-conjugates, 0.1% 6, 2% gentisic acid (7) and 0.1% 2,3-dihydroxy-benzoic acid (8). The different metabolic rates are explicable by the high stability of the ester bond of 1. It is hydrolyzed in artificial intestinal fluid only very slowly (t1/2 = 41.7 h).
authors.affiliation: Sektion Chemie, Wissenschaftsbereich Pharmazie, Humboldt-Universität zu Berlin.
authors.forename: G
authors.initials: G
authors.lastname: Fötsch
authors.forename: S
authors.initials: S
authors.lastname: Pfeifer
authors.forename: M
authors.initials: M
authors.lastname: Bartoszek
authors.forename: P
authors.initials: P
authors.lastname: Franke
authors.forename: K
authors.initials: K
authors.lastname: Hiller
mesh_terms: D000818:Animals; D001592:Benzyl Alcohols / Q000378:metabolism*; D001593:Benzyl Compounds / Q000378:metabolism*; D001711:Biotransformation; D002849:Chromatography, Gas; D004355:Drug Stability; D005243:Feces / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D005960:Glucosides / Q000378:metabolism*; D006027:Glycosides / Q000378:metabolism*; D008297:Male; D010636:Phenols; D051381:Rats; D011919:Rats, Inbred Strains
chemical_list: D001592:Benzyl Alcohols; D001593:Benzyl Compounds; D005960:Glucosides; D006027:Glycosides; D010636:Phenols; C005696:salicin; C045024:leiocarposide
vernacular_title: Biotransformation der Phenolglycoside Leiocarposid und Salicin.