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Titolo:
Chemoenzymatic preparation of silybin beta-glucuronides and their biological evaluation
Autore:
Kren, V; Ulrichova, J; Kosina, P; Stevenson, D; Sedmera, P; Prikrylova, V; Halada, P; Simanek, V;
Indirizzi:
Acad Sci Czech Republ, Inst Microbiol, Lab Biotransformat, CZ-14220 Prague4, Czech Republic Acad Sci Czech Republ Prague Czech Republic 4 20 Prague4, Czech Republic Palacky Univ, Fac Med, Inst Med Chem, CR-77147 Olomouc, Czech Republic Palacky Univ Olomouc Czech Republic CR-77147 147 Olomouc, Czech Republic Palacky Univ, Ctr Bioanalyt Res, CR-77147 Olomouc, Czech Republic Palacky Univ Olomouc Czech Republic CR-77147 147 Olomouc, Czech Republic Ind Res Ltd, Lower Hutt, New Zealand Ind Res Ltd Lower Hutt New ZealandInd Res Ltd, Lower Hutt, New Zealand
Titolo Testata:
DRUG METABOLISM AND DISPOSITION
fascicolo: 12, volume: 28, anno: 2000,
pagine: 1513 - 1517
SICI:
0090-9556(200012)28:12<1513:CPOSBA>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
SILIBININ DIASTEREOMERS; NEUTRAL PH; OXIDATION; SILYMARIN; PLASMA; HPLC;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
16
Recensione:
Indirizzi per estratti:
Indirizzo: Kren, V Acad Sci Czech Republ, Inst Microbiol, Lab Biotransformat, Videnska 1083, CZ-14220 Prague 4, Czech Republic Acad Sci Czech Republ Videnska 1083 Prague Czech Republic 4 ublic
Citazione:
V. Kren et al., "Chemoenzymatic preparation of silybin beta-glucuronides and their biological evaluation", DRUG META D, 28(12), 2000, pp. 1513-1517

Abstract

Chemoenzymatic glucuronidation of the optically pure silybin A (1) using ovine liver glucuronyl transferase afforded three beta -glucuronides of silybin, substituted at phenolic OH groups at the positions C-20 (2), C-7 (3), and C-5 (4) formed in the yields 27, 62.5, and 2.5%, respectively. Using these standards, it was shown that the main silybin conjugate in humans is its 20-beta -D-glucuronate (2), while the C-7 regioisomer (3) was formed in lower proportion. The rate of conjugation of (natural) silybin diastereomers10S, 11S and 10R, 11R, and therefore also their metabolism in humans is rather different. The radical scavenging activity of 2 is considerably lower than that of its aglycone (1); however, the activity of 3 is higher than inthe silybin. These findings corroborate the hypothesis that, at physiological pH, the exclusive target for one-electron oxidation of the silybin molecule is the o-methoxy-phenolic structure at C-19, C-20. This is first pharmacological study using optically pure silybin.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 00:54:26