A spectrophotometric assay for total garlic thiosulfinates content. Kinetic aspects of reaction with chromogenic thiols

• Autorzy: Olech Z. , Zaborska W.
• Języki publikacji: EN

Abstrakty

EN

Garlic (Allium sativum) is a plant known for its antimicrobial, antithrombotic and antiatherosclerotic properties. Those features are attributed to thiosulfi nates, compounds formed in an enzymatic reaction occurring during garlic cloves crashing. A spectrophotometric method for the determination of thiosulfi nate concentration in garlic extracts and supplements was proposed. It is based on reactions between thiosulfi nates and selected chromogenic thiol compounds: 2-mercaptopyridine (2-MP), 4-mercaptopyridine (4-MP), 1-oxide-2-mercaptopyridine (MPO), 2-mercaptopyrimidine (MPM) and 2-nitro-5-thiobenzoic acid (NTB). Then kinetics of the reactions was studied. Rate constants and orders were determined. All reactions are fi rst order with respect to the thiol and fi rst order with respect to TS so the reactions of all tested thiols with garlic TS run in accordance with second order kinetics. Reaction rates vary among the thiol compounds: the constant rates differ from 6.7 (mol/L)-1.min-1 for 2-MP to 1129 (mol/L)-1.min-1 for NTB. Knowledge of the kinetic equation for the reactions and measurements of the initial rates allowed determining thiosulfi nate contents in garlic extracts and supplements.

• Wydawca: -
• Czasopismo: Polish Journal of Food and Nutrition Sciences
• Rocznik: 2012
• Tom: 62
• Numer: 1
• Opis fizyczny: p.23-29,fig.,ref.

Twórcy

autor

Olech Z.

• Faculty of Chemistry, Jagiellonian University, Gronostajowa 3, 30-387 Krakow, Poland

autor

Zaborska W.

Bibliografia

• 1. Arnault I., Christidès J.P., Mandon N., Haffner T., Kahane R., Auger J., High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipep-tide precursors in garlic products using multiple mass spectrometry and UV detection. J. Chromatogr. A, 2003, 991, 69–75.
• 2. Block E., The organosulfur chemistry of the genus Allium-implications for the organic chemistry of sulfur. Angew. Chemie, 1992, 31, 1135–1178.
• 3. Cavallito C.J., Bailey J.H., Allicin, the antibacterial principle of Allium sativum. I Isolation, physical properties and antimicrobial action. J. Am. Chem. Soc., 1944, 66, 1950–1951.
• 4. Degani Y., Patchornik A., Selective cyanylation of sulfhydryl groups. II Synthesis of 2-nitro-5-thiocyanatobenzoic acid. J. Org. Chem., 1971, 36, 2727–2728.
• 5. Egwim I.O., Gruber H.J., Spectrophotometric measurement of mercaptans with 4,4’-dithiodipyridine. Anal. Biochem., 2001, 288, 188–194.
• 6. Han J., Lawson L., Han G., Han P., Spectrophotometric method for quantitative determination of allicin and total garlic thiosulfi nates. Anal. Biochem., 1995, 225, 157–160.
• 7. Hiyasat B., Sabha D., Grotzinger K., Kempfert J., Rauwald J.W., Mohr F.W., Dhein S., Antiplatelet activity of Allium ursinum and Allium sativum. Pharmacology, 2009, 83, 197–204.
• 8. Ichikawa M., Ide N., Yoshida J., Yamaguchi H., Ono K., Determination of seven organosulfur compounds in garlic by highperformance liquid chromatography. J. Agric. Food Chem., 2006, 54, 1535–1540.
• 9. Juszkiewicz A., Zaborska A., Łaptaś A., Olech Z., A study of the inhibition of jack bean urease by garlic extract. Food Chem., 2004, 85, 553–558.
• 10. Keusgen M., Jünger M., Krest I., Schönning M.J., Development of a biosensor specifi c for cysteine sulphoxides. Biosensors & Bioelectronics, 2003, 18, 805–812.
• 11. Krest I., Keusgen M., Biosensoric fl ow–through method for the determination of cysteine sulfoxides. Anal. Chem. Acta, 2002, 469, 155–164.
• 12. Kyung K.H., Lee Y.C., Antimicrobial activities of sulfur compounds derived from S-alk(en)yl-L-cysteine sulfoxides in Allium and Brassica. Food Rev. Int., 2001, 17, 183–198.
• 13. Lawson L.D., Wang Z.J., Low allicin release from garlic supplements: major problem due to the sensitivities of alliinase activity. J. Agric. Food Chem., 2001, 49, 2592–2599.
• 14. Lawson L.D., Gardner C.D., Composition, stability, and bioavailability of garlic products used in a clinical trial. J. Agric. Food Chem., 2005, 53, 6254–6261.
• 15. Miron T., Rabinkov A., Mirelman D., Weiner L., Wilchek M., A spectrophotometric assay for allicin and alliinase (alliin lyase) activity: Reaction of 2-nitro-5-thiobenzoate with thiosufi nates. Anal. Biochem., 1998, 265, 317–325.
• 16. Miron T., Shin I., Feigenblat G., Weiner L., Mirelman D., Wilchek M., Rabinkov A., A spectrophotometric assay for allicin, alliin and alliinase (Alliin lyase) with chromogenic thiol: reaction of 4-mercaptopyridine with thiosulfi nates. Anal. Biochem., 2002, 307, 76–83.
• 17. Qi R., Wang Z., Pharmacological effects of garlic extract. Trends Pharmacol. Sci., 2003, 24, 62–63.
• 18. Riener C.K., Kada G., Gruber H.J., Quick measurement of protein sulfhydryls with Ellman’s reagent and with 4,4’-dithiodipyridine. Anal. Bioanal. Chem., 2002, 373, 266–276.
• 19. Rosen R.T., Hiserodt R.D., Fukuda E.K., Ruiz R.J., Zhou Z., Lech J., Rosen S.L., Hartman T.G., Determination of allicin, S-allylcysteine and volatile metabolites of garlic in breath, plasma or simulated gastric fl uids. J. Nutr. 2001, 131, 968S-971S.
• 20. Yoo K.S., Pike L.M., Hamilton B.K, Determination of background pyruvic acid concentrations in onions, Allium species and other vegetables. Sci. Hort., 2001, 89, 249- 256.

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