Formation of the thiocyanate conjugate of chlorogenic acid in coffee under acidic conditions in the presence of thiocyanate and nitrite: possible occurrence in the stomach.
The objective of the present study was to elucidate how chlorogenic acid in coffee was transformed under acidic conditions simulating the mixture of saliva and gastric juice. When coffee was incubated in acidified saliva that contained nitrite and SCN-, in addition to nitric oxide (NO), four major components were detected. Two of the four components (components 3 and 4) were generated when chlorogenic acid was incubated in acidified saliva and when incubated in an acidic buffer solution in the presence of both nitrite and SCN-. By the incubation of chlorogenic acid in acidic nitrite in the absence of SCN-, components 3 and 4 were not formed but the quinone of chlorogenic acid and nitrated chlorogenic acid were formed. The result indicates that SCN- was indispensable for nitrous acid induced formation of components 3 and 4. Component 4 was isolated and its structure was determined to be (E)-5'-(3-(7-hydroxy-2-oxobenzo[d] [1,3]oxathiol-4-yl)acryloyloxy)quinic acid. Component 3, which was suggested to be 2-thiocyanatochlorogenic acid, seemed to be formed by the reaction between SCN- and the quinone of chlorogenic acid. As it has been reported that the quinone of chlorogenic acid can react with thiols and can decompose producing H2O2, the formation of component 4 can reduce the toxic effects of the quinone of chlorogenic acid.
Takahama
Umeo
U
Department of Bioscience, Kyushu Dental College, Kitakyushu 803-8580 Japan. takahama@kyu-dent.ac.jp
Tanaka
Mariko
M
Oniki
Takayuki
T
Hirota
Sachiko
S
Yamauchi
Ryo
R
D002726:Chlorogenic Acid / Q000032:analysis / Q000737:chemistry* / Q000378:metabolism; D003069:Coffee / Q000737:chemistry*; D004847:Epithelial Cells / Q000378:metabolism; D005750:Gastric Juice / Q000737:chemistry; D006801:Humans; D006863:Hydrogen-Ion Concentration; D009573:Nitrites / Q000032:analysis / Q000494:pharmacology*; D012463:Saliva / Q000737:chemistry / Q000166:cytology; D013861:Thiocyanates / Q000737:chemistry* / Q000494:pharmacology*
D003069:Coffee; D009573:Nitrites; D013861:Thiocyanates; D002726:Chlorogenic Acid