Correlation of Structure of Ascorbic Acid with Bactericidal Activity

Abstract

The bactericidal activity of L-ascorbic acid (AsA) is well known. To elucidate the correlation of structure of AsA with the bactericidal activity, 13 derivatives substituted at C2, C3, C5 and C6 of AsA were synthesized and examined for bactericidal activity using eight bacterial species. C2- and C2,6-substituted derivatives, in general, had lower activity than AsA. C6- and C5,6-substituted derivatives had the same activity as AsA. C3- and C2,3-substituted derivatives had no activity. The findings indicate that the bactericidal activity of AsA is based on the enediol system and OH-group at C3 in the enediol system is necessary for the activity. Another purpose of this study is to find out AsA derivatives with higher activity than AsA. 2-O-octanoyl-AsA and 2,6-di-O-octanoyl-AsA exhibited higher bactericidal activity against Lactobacillus casei and Staphylococcus aureus