Variation in the Methylation of Caffeoylquinic Acids and Urinary Excretion of 3'-methoxycinnamic acid-4'-Sulfate After Apple Consumption by Volunteers

Abstract

Introduction: It has been reported that the phenolic metabolite 3'-methoxycinnamic acid-4'-sulfate generated from 5-O-caffeoylquinic acid may have potential benefits in human health. However, the variation in 3'- and 4'-methylation of 3',4'-dihydroxycinnamic acid and its impact on the yield of this sulfate metabolite is unclear and has been poorly studied.

Methods and results: To address this aim, the excreted 3'-methoxy and 4'-methoxy metabolites in urine samples (24-h) are determined in 14 volunteers after an acute intake of 80 g of red-fleshed apple (RFA) or white-fleshed apple (WFA). These methoxy metabolites are also determined in the same volunteers in a second acute intake after a 6-week sustained consumption of the same products.

Conclusion: Seven 3'-methoxy and seven 4'-methoxy metabolites are determined, i.e., the free cinnamic and corresponding phenylpropanoic acid, plus their sulfate, glucuronide, and glycine conjugates. In only six volunteers, five females and one male, is 4'-methylation preferred over 3'-methylation, but it is observed that an individual's 3'- : 4'-methylation ratio can change over time, and that the yield of 3'-methoxycinnamic acid-4'-sulfate is extremely variable, ranging from undetectable to 71% of the total C₆ -C₃ metabolites excreted, and any benefit accruing from this metabolite will not necessarily be available to all consumers.

Keywords: 3′- / 4′-methylation ratio; 3′-methoxycinnamic acid-4′sulfate; apples; caffeoylquinic acids; catechol-O-methyl transferase.