Vitamin C activity in guinea pigs of 6-O-acyl-2-O-alpha-D-glucopyranosyl-L- ascorbic acids with a branched-acyl chain.
A series of novel acylated ascorbic acid derivatives, 6-O-acyl-2-O-alpha-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-alpha-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.
Tai
Akihiro
A
Department of Immunochemistry, Faculty of Pharmaceutical Sciences, Okayama University, Okayama 700-8530, Japan.
Kawasaki
Daisuke
D
Goto
Satomi
S
Gohda
Eiichi
E
Yamamoto
Itaru
I
D000215:Acylation; D000469:Alkaline Phosphatase / Q000378:metabolism; D000818:Animals; D001205:Ascorbic Acid / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors / Q000493:pharmacokinetics* / Q000494:pharmacology; D001206:Ascorbic Acid Deficiency / Q000188:drug therapy / Q000378:metabolism / Q000473:pathology; D001682:Biological Availability; D001921:Brain / Q000378:metabolism; D004950:Esterases / Q000378:metabolism; D006168:Guinea Pigs; D006868:Hydrolysis; D007421:Intestine, Small / Q000378:metabolism; D007668:Kidney / Q000378:metabolism; D008099:Liver / Q000378:metabolism; D012614:Scurvy / Q000188:drug therapy / Q000378:metabolism / Q000473:pathology; D015431:Weight Loss / Q000187:drug effects; D000520:alpha-Glucosidases / Q000378:metabolism
D004950:Esterases; D000469:Alkaline Phosphatase; D000520:alpha-Glucosidases; D001205:Ascorbic Acid