title: A tissue homogenate method to prepare gram-scale Allium thiosulfinates and their disulfide conjugates with cysteine and glutathione.
abstract: The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).
authors: Department of Food Science, Babcock Hall, University of Wisconsin-Madison, 1605 Linden Drive, Madison, Wisconsin 53706, USA. gdzhang@ucdavis.edu
authors: Guodong
authors: G
authors: Zhang
authors: Kirk L
authors: KL
authors: Parkin
mesh_terms: D000490:Allium / Q000737:chemistry* / Q000201:enzymology; D000818:Animals; D002460:Cell Line; D045744:Cell Line, Tumor; D003545:Cysteine / Q000378:metabolism; D004790:Enzyme Induction / Q000187:drug effects; D005978:Glutathione / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008114:Liver Neoplasms, Experimental; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D013441:Sulfinic Acids / Q000378:metabolism* / Q000494:pharmacology
chemical_list: D008070:Lipopolysaccharides; C584655:S-1-propenylmercaptoglutathione; D013441:Sulfinic Acids; C100040:thiosulfinic acids; D009569:Nitric Oxide; D016660:NAD(P)H Dehydrogenase (Quinone); D005978:Glutathione; D003545:Cysteine