Abstract
Ascorbic acid 2-glucoside (AA-2G) is a stable ascorbic acid (AsA) derivative approved as a quasi-drug principal ingredient in skin care and a food additive in Japan and is widely used in cosmetics and health foods. AA-2G is a provitamin C agent that exhibits vitamin C activity after its enzymatic hydrolysis to AsA by α-glucosidase. We have synthesized a series of lipophilic stable AsA derivatives (6-Acyl-AA-2G) having straight-acyl chains of varying carbon chain lengths from C4 to C18 and branched-acyl chains of varying carbon chain lengths from C6 to C16 to improve the bioavailability of AA-2G and have indicated that 6-Acyl-AA-2G exerts usually known vitamin C functions efficiently in vitro and in vivo. Recently, we found that, unexpectedly, 6-Acyl-AA-2G having a straight-acyl chain per se had antiallergic activity based on its degranulation inhibitory action and that a 6-O-acyl AsA, an intermediate in the hydrolysis of 6-Acyl-AA-2G having a branched-acyl chain to AsA, showed a significant antitumor activity. More recently, we succeeded in creating AsA derivatives that exhibit a superior antiallergic effect. In this review, the author presents a possible drug development application for created AsA derivatives.
