[3H]Allicin: preparation and applications.
Allicin (diallylthiosulfinate), the active substance of garlic, has been shown to possess a variety of biological activities. Mechanistic and pharmacokinetic studies of allicin and its derivatives raise the need for a labeled compound. However, labeling of this volatile and unstable liquid requires delicate handling. Here, we describe a simple method for the preparation of (3)H-labeled allicin. This was achieved by applying synthetic [(3)H]alliin ([2,3-(3)H]allylcysteine sulfoxide) to a column containing immobilized alliinase [EC 4.1.1.4.] from garlic. Purification of [(3)H]allicin was done by differential adsorbtion of the reaction components on a neutral polystyrene resin, Porapak Q. Thiol-containing compounds are known to be the main target of allicin. In this work we demonstrated that [(3)H]allicin can be used for the synthesis of labeled [(3)H]allylmercapto derivatives of SH peptides and proteins. Thus, we prepared [(3)H]S-allylmercaptoglutathione which can be used in metabolic studies. Moreover, we showed that incubation of alliinase with [(3)H]allicin led to modification of 1.4 cysteine residues per subunit of the enzyme.
Miron
T
T
Department of Biological Chemistry, The Weizmann Institute of Science, Rehovot 76100, Israel.
Bercovici
T
T
Rabinkov
A
A
Wilchek
M
M
Mirelman
D
D
D000327:Adsorption; D002850:Chromatography, Gel; D004220:Disulfides; D013441:Sulfinic Acids / Q000138:chemical synthesis* / Q000302:isolation & purification; D014316:Tritium
D004220:Disulfides; D013441:Sulfinic Acids; D014316:Tritium; C006452:allicin