Metabolism and Recovery of Epithionitriles from Glucosinolates—A Human Intervention Study

Abstract

Scope: Epithionitriles can be main glucosinolate hydrolysis products inBrassica vegetables such as cabbage or pak choi. Here, for the first time, the bioavailability and metabolism of longer-chain epithionitriles (C4-C5) is studied in a human intervention study. Methods and results: After consumption of a white cabbage or pak choi sprouts beverage, rich in either 1-cyano-2,3-epithiopropane (CETP) or 1-cyano-3,4-epithiobutane (CETB) and 1-cyano-4,5-epithiopentane (CETPent), blood and urine samples of nine participants are taken and the metabolites are analyzed. The corresponding N-acetyl-S-(cyano-(methylthio)alkyl)-l-cysteine metabolites are identified and quantified by isotope dilution method using UHPLC-TOF-MS. The standards for N-acetyl-S-(cyano-(methylthio)alkyl)-l-cysteine metabolites from CETB andCETPent are synthesized for the first time and their structure confirmed by NMR spectroscopy. In contrast to the metabolites of CETP and CETPent, the expected metabolite of CETB is not detectable. The recoveries of the CETP and CETPent metabolites are 28 ± 9% for CETP and 12 ± 3% for CETPent in urine within 24 h. Conclusion: CETP and CETPent are quickly uptaken, metabolized via the mercapturic acid pathway, and excreted via urine, while for CETB the corresponding metabolite is not detectable. Therefore, an additional metabolization pathway seems to exist.