Academic Journal
Simultaneous Determination and Enantiomeric Separation of Five DL-Thiol Compounds Using UHPLC-HRMS With Chiral Derivatization in Sake: Dynamic Monitoring of Human Urine After Drinking.
| Title: | Simultaneous Determination and Enantiomeric Separation of Five DL-Thiol Compounds Using UHPLC-HRMS With Chiral Derivatization in Sake: Dynamic Monitoring of Human Urine After Drinking. |
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| Authors: | Xiao S; Tianjin Key Laboratory of Birth Defects for Prevention and Treatment, Department of Pharmacy of Tianjin Children's Hospital, Children's Hospital, Tianjin University, Tianjin, China., Shi H; Pharmaceutical Analysis, College of Pharmacy, Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, Yanbian University, Yanji, Jilin Province, China., Song S; Pharmaceutical Analysis, College of Pharmacy, Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, Yanbian University, Yanji, Jilin Province, China., Min JZ; Pharmaceutical Analysis, College of Pharmacy, Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, Yanbian University, Yanji, Jilin Province, China. |
| Source: | Chirality [Chirality] 2026 Jul; Vol. 38 (7), pp. e70112. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Wiley Country of Publication: United States NLM ID: 8914261 Publication Model: Print Cited Medium: Internet ISSN: 1520-636X (Electronic) Linking ISSN: 08990042 NLM ISO Abbreviation: Chirality Subsets: MEDLINE |
| Imprint Name(s): | Original Publication: New York, NY : Wiley |
| MeSH Terms: | Sulfhydryl Compounds*/urine , Sulfhydryl Compounds*/chemistry , Sulfhydryl Compounds*/isolation & purification , Liquid Chromatography-Mass Spectrometry*/methods , Alcoholic Beverages*/analysis, Chromatography, High Pressure Liquid/methods ; Mass Spectrometry/methods ; Cysteine/urine ; Stereoisomerism ; Humans |
| Abstract: | Sake, a fermented alcoholic beverage made from rice and Aspergillus oryzae through microbial fermentation, contains thiol compounds that are the primary source of its distinctive sweet aroma. However, to date, there has been no report on the detection of chiral thiol compounds in sake. This study introduces a novel UHPLC-HRMS method utilizing the (R)-(5-(3-isothiocyanatopyrrolidin-1-yl)-5-oxopentyl) triphenylphosphonium (NCS-OTPP) chiral mass spectrometry probe for the simultaneous detection of five DL-thiol compounds in sake. Separation was achieved using a YMC Triart C18 column (2.0 × 150 mm, 1.9 μm), employing an isocratic elution method to isolate DD/LL-GSH, γ-L-Glu-L-Cys, DL-Cys, DL-Hcy, and DL-Ac-Cys. The method demonstrated excellent linearity (R2 ≥ 0.9992), intraday precision (0.43%-13.18%), and an average recovery rate of 91.62%-110.40%. A comparative analysis of DL-thiol compound content in seven different types of sake from various countries and manufacturers revealed the presence of five chiral thiol compounds-LL-GSH, γ-L-Glu-L-Cys, DL-Cys, DL-Hcy, and L-Ac-Cys-across Japanese and Korean sake, with L-Cys being the most abundant and D-Ac-Cys the least. Notably, γ-L-Glu-L-Cys was detected only in two types of Korean sake and absent in Japanese sake. Additionally, the study investigated the metabolic kinetics of chiral thiol compounds in human urinary specimens after alcohol ingestion, constructing a metabolic fitting curve. The peak concentrations of DL-Cys, DL-Hcy, and LL-GSH were attained 15 min following consumption, with slow clearance, returning to baseline at 60 min. The metabolic fitting curve effectively captures the dynamic changes in urinary metabolism. This research presents a new method for detecting chiral thiol compounds in sake and monitoring urinary metabolism after alcohol consumption. (© 2026 Wiley Periodicals LLC.) |
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| Grant Information: | 32160234 National Natural Science Foundation of China; TJYXZDXK-3-016B Tianjin Key Medical Discipline Construction Project |
| Contributed Indexing: | Keywords: DL‐thiol compound; UHPLC–HRMS; chiral resolution; sake; urine |
| Substance Nomenclature: | 0 (Sulfhydryl Compounds) K848JZ4886 (Cysteine) |
| Entry Date(s): | Date Created: 20260617 Date Completed: 20260617 Latest Revision: 20260726 |
| Update Code: | 20260726 |
| PubMed Central ID: | PMC13357306 |
| DOI: | 10.1002/chir.70112 |
| PMID: | 42304807 |
| Database: | MEDLINE |
| ISSN: | 1520-636X |
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| DOI: | 10.1002/chir.70112 |