Changes in organosulfur compounds in garlic cloves during storage.

We determined the changes in the contents of three gamma-glutamyl peptides and four sulfoxides in garlic cloves during storage at -3, 4, and 23 degrees C for 150 days using a validated high-performance liquid chromatography method that we reported recently. When garlic was stored at 4 degrees C for 150 days, marked conversion of the gamma-glutamyl peptides, gamma-L-glutamyl-S-allyl-L-cysteine and gamma-L-glutamyl-S-(trans-1-propenyl)-L-cysteine (GSPC), to sulfoxides, alliin and isoalliin, was observed. Interestingly, however, when garlic was stored at 23 degrees C, a decrease in GSPC and a marked increase in cycloalliin, rather than isoalliin, occurred. To elucidate in detail the mechanism involved, the conversion of isoalliin to cycloalliin in both buffer solutions (pH 4.6, 5.5, and 6.5) and garlic cloves at 25 and 35 degrees C was examined. Decreases in the concentration of isoalliin in both the solutions and the garlic cloves during storage followed first-order kinetics and coincided with the conversion of cycloalliin. Our data indicated that isoalliin produced enzymatically from GSPC is chemically converted to cycloalliin and that the cycloalliin content of garlic cloves increases during storage at higher temperature. These data may be useful for controlling the quality and biological activities of garlic and its preparations.