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Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract.
J Agric Food Chem. 2019 Feb 27; 67(8):2190-2200.JA

Abstract

A powder formulation of aged garlic extract was heated at 100 °C for 1 day to obtain higher antioxidant activity determined with 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging (ARS) and oxygen radical absorbance capacity (ORAC) assays. Activity-guided fractionation afforded 12 new in vitro antioxidative Maillard-type products, α-[(2-formyl-5-hydroxymethyl)pyrrol-1-yl]arginine (3), 4-[7-hydroxy-6-(hydroxymethyl)-7,8-dihydro-6 H-pyrano[2,3- b] pyrazine-3-yl]butane-1,2,3-triol (4), 4-[6-(1,2-dihydroxyethyl)-6,7-dihydro-furo[2,3- b]pyrazin-3-yl]-butane-1,2,3-triol (5), α-[(2-formyl-5-hydroxymethyl)-pyrrol-1-yl] aspartic acid (12), 1-[5-(1,2-dihydroxyethyl)-2-oxotetrahydrofuran-3-yl]-5-(hydroxymethyl)-1 H-pyrrole-2-carbaldehyde (14), 4-(6-ethyl-2-pyrazinyl)-1,2,3-butanetriol (17), α-[(2-formyl-5-hydroxymethyl)pyrrol-1-yl] glutamic acid (19), (S)-1-[(5-hydroxymethyl)furan-2-yl]methyl]-5-oxopyrrolidine-2-carboxylic acid (20), 3-hydroxy-1 H-[{5-(hydroxymethyl)furan-2-yl}methyl]-2,5-dioxo-3-pyrrolidine acetic acid (21), (E)-4-(5-methylpyrazin-2-yl)but-3-ene-7,2-diol (23), 4-acetyl-6-(hydroxymethyl)picolinic acid (24), (E)-4-(6-methylpyrazin-2-yl)but-3-ene-1,2-diol (26) and 14 known compounds, 1, 2, 6-11, 13, 15, 16, 18, 22 and 25, which were characterized via 1D/2D-NMR, CD spectroscopy, and mass spectrometry. ARS and ORAC activities of these antioxidants ranged from 0.01 to 0.49 μmol TE/μmol and from 0.01 to 3.50 μmol TE/μmol, respectively. Additionally, plausible formation pathways for the new organic acid-type products (15, 20, and 21) were proposed based on proving their generation in model reactions detected via liquid chromatography-mass spectrometry (LC-MS/MS).

Authors+Show Affiliations

Food Chemistry and Molecular Sensory Science , Technische Universität München , Lise-Meitner-Straβe 34 , 85354 Freising , Germany.Food Chemistry and Molecular Sensory Science , Technische Universität München , Lise-Meitner-Straβe 34 , 85354 Freising , Germany.Food Chemistry and Molecular Sensory Science , Technische Universität München , Lise-Meitner-Straβe 34 , 85354 Freising , Germany.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30715866

Citation

Wakamatsu, Junichiro, et al. "Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract." Journal of Agricultural and Food Chemistry, vol. 67, no. 8, 2019, pp. 2190-2200.
Wakamatsu J, Stark TD, Hofmann T. Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract. J Agric Food Chem. 2019;67(8):2190-2200.
Wakamatsu, J., Stark, T. D., & Hofmann, T. (2019). Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract. Journal of Agricultural and Food Chemistry, 67(8), 2190-2200. https://doi.org/10.1021/acs.jafc.8b06907
Wakamatsu J, Stark TD, Hofmann T. Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract. J Agric Food Chem. 2019 Feb 27;67(8):2190-2200. PubMed PMID: 30715866.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antioxidative Maillard Reaction Products Generated in Processed Aged Garlic Extract. AU - Wakamatsu,Junichiro, AU - Stark,Timo D, AU - Hofmann,Thomas, Y1 - 2019/02/15/ PY - 2019/2/5/pubmed PY - 2019/3/9/medline PY - 2019/2/5/entrez KW - Maillard reaction KW - aged garlic extract KW - antioxidant KW - citric acid KW - glutamic acid SP - 2190 EP - 2200 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 67 IS - 8 N2 - A powder formulation of aged garlic extract was heated at 100 °C for 1 day to obtain higher antioxidant activity determined with 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging (ARS) and oxygen radical absorbance capacity (ORAC) assays. Activity-guided fractionation afforded 12 new in vitro antioxidative Maillard-type products, α-[(2-formyl-5-hydroxymethyl)pyrrol-1-yl]arginine (3), 4-[7-hydroxy-6-(hydroxymethyl)-7,8-dihydro-6 H-pyrano[2,3- b] pyrazine-3-yl]butane-1,2,3-triol (4), 4-[6-(1,2-dihydroxyethyl)-6,7-dihydro-furo[2,3- b]pyrazin-3-yl]-butane-1,2,3-triol (5), α-[(2-formyl-5-hydroxymethyl)-pyrrol-1-yl] aspartic acid (12), 1-[5-(1,2-dihydroxyethyl)-2-oxotetrahydrofuran-3-yl]-5-(hydroxymethyl)-1 H-pyrrole-2-carbaldehyde (14), 4-(6-ethyl-2-pyrazinyl)-1,2,3-butanetriol (17), α-[(2-formyl-5-hydroxymethyl)pyrrol-1-yl] glutamic acid (19), (S)-1-[(5-hydroxymethyl)furan-2-yl]methyl]-5-oxopyrrolidine-2-carboxylic acid (20), 3-hydroxy-1 H-[{5-(hydroxymethyl)furan-2-yl}methyl]-2,5-dioxo-3-pyrrolidine acetic acid (21), (E)-4-(5-methylpyrazin-2-yl)but-3-ene-7,2-diol (23), 4-acetyl-6-(hydroxymethyl)picolinic acid (24), (E)-4-(6-methylpyrazin-2-yl)but-3-ene-1,2-diol (26) and 14 known compounds, 1, 2, 6-11, 13, 15, 16, 18, 22 and 25, which were characterized via 1D/2D-NMR, CD spectroscopy, and mass spectrometry. ARS and ORAC activities of these antioxidants ranged from 0.01 to 0.49 μmol TE/μmol and from 0.01 to 3.50 μmol TE/μmol, respectively. Additionally, plausible formation pathways for the new organic acid-type products (15, 20, and 21) were proposed based on proving their generation in model reactions detected via liquid chromatography-mass spectrometry (LC-MS/MS). SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/30715866/Antioxidative_Maillard_Reaction_Products_Generated_in_Processed_Aged_Garlic_Extract_ L2 - https://doi.org/10.1021/acs.jafc.8b06907 DB - PRIME DP - Unbound Medicine ER -