Volatile Antioxidants Formed from an L-Cysteine/D-Glucose Maillard Model System

Jason P. Eiserich; Carlos Macku; Takayuki Shibamoto

doi:10.1021/jf00022a050

Volatile Antioxidants Formed from an L-Cysteine/D-Glucose Maillard Model System

Jason P. Eiserich, Carlos Macku, Takayuki Shibamoto

Nephrology

Research output: Contribution to journal › Article

34 Scopus citations

Abstract

The microwave-induced volatile compounds formed from an l-cysteine/d-glucose Maillard model system at different pHs were evaluated for antioxidative activity using a newly developed method. The dichloromethane extracts of pH 9 and 5 showed the strongest antioxidative effects. Fractionation of the pH 9 extract by column chromatography revealed three fractions possessing antioxidative activity. 2,4,5-Trimethyloxazole, 2,4,5-trimethylthiazole, 4,5-dimethylthiazole, oxazole, thiazole, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) were identified in these fractions as volatile antioxidants. The strongest antioxidative activity was displayed by DMHF, followed by the oxazoles, whereas the thiazoles showed only slight activity. Trimethylpyrazine, another major volatile compound produced in the Maillard reaction, did not show any antioxidative activity. The antioxidative activities of these heterocyclic volatiles were directly dependent upon their concentrations.

Original language	English (US)
Pages (from-to)	1982-1988
Number of pages	7
Journal	Journal of Agricultural and Food Chemistry
Volume	40
Issue number	10
DOIs	https://doi.org/10.1021/jf00022a050
State	Published - Oct 1 1992

Fingerprint

ASJC Scopus subject areas

Chemistry(all)
Agricultural and Biological Sciences(all)

Cite this

Eiserich, J. P., Macku, C., & Shibamoto, T. (1992). Volatile Antioxidants Formed from an L-Cysteine/D-Glucose Maillard Model System. Journal of Agricultural and Food Chemistry, 40(10), 1982-1988. https://doi.org/10.1021/jf00022a050

@article{e470924a02464d6db5a6f5d5dde40854,

title = "Volatile Antioxidants Formed from an L-Cysteine/D-Glucose Maillard Model System",

abstract = "The microwave-induced volatile compounds formed from an l-cysteine/d-glucose Maillard model system at different pHs were evaluated for antioxidative activity using a newly developed method. The dichloromethane extracts of pH 9 and 5 showed the strongest antioxidative effects. Fractionation of the pH 9 extract by column chromatography revealed three fractions possessing antioxidative activity. 2,4,5-Trimethyloxazole, 2,4,5-trimethylthiazole, 4,5-dimethylthiazole, oxazole, thiazole, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) were identified in these fractions as volatile antioxidants. The strongest antioxidative activity was displayed by DMHF, followed by the oxazoles, whereas the thiazoles showed only slight activity. Trimethylpyrazine, another major volatile compound produced in the Maillard reaction, did not show any antioxidative activity. The antioxidative activities of these heterocyclic volatiles were directly dependent upon their concentrations.",

author = "Eiserich, {Jason P.} and Carlos Macku and Takayuki Shibamoto",

year = "1992",

month = oct

day = "1",

doi = "10.1021/jf00022a050",

language = "English (US)",

volume = "40",

pages = "1982--1988",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - Volatile Antioxidants Formed from an L-Cysteine/D-Glucose Maillard Model System

AU - Eiserich, Jason P.

AU - Macku, Carlos

AU - Shibamoto, Takayuki

PY - 1992/10/1

Y1 - 1992/10/1

N2 - The microwave-induced volatile compounds formed from an l-cysteine/d-glucose Maillard model system at different pHs were evaluated for antioxidative activity using a newly developed method. The dichloromethane extracts of pH 9 and 5 showed the strongest antioxidative effects. Fractionation of the pH 9 extract by column chromatography revealed three fractions possessing antioxidative activity. 2,4,5-Trimethyloxazole, 2,4,5-trimethylthiazole, 4,5-dimethylthiazole, oxazole, thiazole, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) were identified in these fractions as volatile antioxidants. The strongest antioxidative activity was displayed by DMHF, followed by the oxazoles, whereas the thiazoles showed only slight activity. Trimethylpyrazine, another major volatile compound produced in the Maillard reaction, did not show any antioxidative activity. The antioxidative activities of these heterocyclic volatiles were directly dependent upon their concentrations.

AB - The microwave-induced volatile compounds formed from an l-cysteine/d-glucose Maillard model system at different pHs were evaluated for antioxidative activity using a newly developed method. The dichloromethane extracts of pH 9 and 5 showed the strongest antioxidative effects. Fractionation of the pH 9 extract by column chromatography revealed three fractions possessing antioxidative activity. 2,4,5-Trimethyloxazole, 2,4,5-trimethylthiazole, 4,5-dimethylthiazole, oxazole, thiazole, and 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) were identified in these fractions as volatile antioxidants. The strongest antioxidative activity was displayed by DMHF, followed by the oxazoles, whereas the thiazoles showed only slight activity. Trimethylpyrazine, another major volatile compound produced in the Maillard reaction, did not show any antioxidative activity. The antioxidative activities of these heterocyclic volatiles were directly dependent upon their concentrations.

UR - http://www.scopus.com/inward/record.url?scp=0000649299&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000649299&partnerID=8YFLogxK

U2 - 10.1021/jf00022a050

DO - 10.1021/jf00022a050

M3 - Article

AN - SCOPUS:0000649299

VL - 40

SP - 1982

EP - 1988

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 10

ER -

Access to Document

10.1021/jf00022a050