Purification of S -Alk(en)yl alka/enethiosulfinates of garlic ( Allium sativum L.) by using recycling preparative HPLC

S -Alk(en)yl alka/enethiosulfinates formed in crushed garlic were purified by using recycling preparative HPLC. Allyl 2-propenethiosulfinate and methyl methanethiosulfinate were effective separated because no other thiosulfinates were coeluted with them. Allyl methanethiosulfinate and methyl 2-propenethiosulfinate, trans -1-propenyl methanethiosulfinate and methyl trans -1-propenethiosulfinate, ( cis )- and ( trans )-1-propenyl 2-propenethiosulfinate were eluted as 1 peak, respectively, and further separated by using additional kinds of column. Since the quantity of trans -1-propenyl trans -1-propenethiosulfinate (PPTHS) was small in garlic, PPTHS was isolated from a mixture of blanched onion homogenate and garlic alliinase and purified. Purified thiosulfinates can be employed for the study of antimicrobial activity, flavor, and greening of garlic.