Vitamin C Activity in Guinea Pigs of 6-O-Acyl-2-O-α-D-glucopyranosyl-L- ascorbic Acids with a Branched-acyl Chain

• Published in: Bioscience, biotechnology, and biochemistry Vol. 67; no. 8; pp. 1675 - 1682
• Main Authors: TAI, Akihiro, KAWASAKI, Daisuke, GOTO, Satomi, GOHDA, Eiichi, YAMAMOTO, Itaru
• Format: Journal Article
• Language: English
• Published: Tokyo Japan Society for Bioscience, Biotechnology, and Agrochemistry 01.01.2003; Japan Society for Bioscience Biotechnology and Agrochemistry
• Subjects: 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G); Acylation; Alkaline Phosphatase - metabolism; alpha-Glucosidases - metabolism; Animals; antiscorbutic activity; Ascorbic Acid - analogs & derivatives; Ascorbic Acid - antagonists & inhibitors; Ascorbic Acid - pharmacokinetics; Ascorbic Acid - pharmacology; Ascorbic Acid Deficiency - drug therapy; Ascorbic Acid Deficiency - metabolism; Ascorbic Acid Deficiency - pathology; Biological and medical sciences; Biological Availability; Brain - metabolism; Esterases - metabolism; Fundamental and applied biological sciences. Psychology; Guinea Pigs; Hydrolysis; Intestine, Small - metabolism; Kidney - metabolism; lipophilic ascorbate; Liver - metabolism; metabolism; Scurvy - drug therapy; Scurvy - metabolism; Scurvy - pathology; stable ascorbate; Weight Loss - drug effects; Ascorbic acid; stable ascorbate; Rodentia; Vitamin; antiscorbutic activity; Acyl; 6-O-acyl-2-O-a-D-glucopyranosyl-L-ascorbic acids (6-Acyl-AA-2G); Branched chain; Vertebrata; Mammalia; Guinea pig; metabolism; lipophilic ascorbate
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.67.1675

A series of novel acylated ascorbic acid derivatives, 6-O-acyl-2-O-α-D-glucopyranosyl-L-ascorbic acids with a branched-acyl chain (6-bAcyl-AA-2G) were recently developed in our laboratory as stable and lipophilic ascorbate derivatives. In this study, the bioavailability of 6-bAcyl-AA-2G was investigated in guinea pigs. Various tissue homogenates from guinea pigs hydrolyzed 6-bAcyl-AA-2G to give ascorbic acid (AA), 2-O-α-D-glucopyranosyl-L-ascorbic acid (AA-2G), and 6-O-acyl AA. The releasing pattern of the three hydrolysates suggested that 6-bAcyl-AA-2G was hydrolyzed via 6-O-acyl AA to AA as a main pathway and via AA-2G to AA as a minor pathway. The former pathway seems to be of advantage, because 6-O-acyl AA, as well as AA, can have vitamin C activity. In addition, we found that a derivative with an acyl chain of C 12 , 6-bDode-AA-2G, had a pronounced therapeutic effect in scorbutic guinea pigs by its repeated oral administrations. These results indicate that 6-bAcyl-AA-2G is a readily available source of AA in vivo, and may be a promising antioxidant for skin care and treatment of diseases associated with oxidative stress.