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Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum).
J Agric Food Chem. 2016 Jul 27; 64(29):5845-54.JA

Abstract

In order to gain first insight into candidate Maillard reaction products formed upon thermal processing of garlic, mixtures of glucose and S-allyl-l-cysteine, the major sulfur-containing amino acid in garlic, were low-moisture heated, and nine major reaction products were isolated. LC-TOF-MS, 1D/2D NMR, and CD spectroscopy led to their identification as acortatarin A (1), pollenopyrroside A (2), epi-acortatarin A (3), xylapyrroside A (4), 5-hydroxymethyl-1-[(5-hydroxymethyl-2-furanyl)methyl]-1H-pyrrole-2-carbalde-hyde (5), 3-(allylthio)-2-(2-formyl-5-hydroxymethyl-1H-pyrrol-1-yl)propanoic acid (6), (4S)-4-(allylthiomethyl)-3,4-dihydro-3-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (7), (2R)-3-(allylthio)-2-[(4R)-4-(allylthiomethyl)-6-formyl-3-oxo-3,4-dihydropyrrolo-[1,2-a]pyrazin-2(1H)-yl]propanoic acid (8), and (2R)-3-(allylthio)-2-((4S)-4-(allylthiomethyl)-6-formyl-3-oxo-3,4-dihydropyrrolo-[1,2-a]pyrazin-2(1H)-yl)propanoic acid (9). Among the Maillard reaction products identified, compounds 5-9 have not previously been published. The thermal generation of the literature known spiroalkaloids 1-4 is reported for the first time. Sensory analysis revealed a bitter taste with thresholds between 0.5 and 785 μmol/kg for 1-5 and 7-9. Compound 6 did not show any intrinsic taste (water) but exhibited a strong mouthfullness (kokumi) enhancing activity above 186 μmol/kg. LC-MS/MS analysis showed 1-9 to be generated upon pan-frying of garlic with the highest concentration of 793.7 μmol/kg found for 6, thus exceeding its kokumi threshold by a factor of 4 and giving evidence for its potential taste modulation activity in processed garlic preparations.

Authors+Show Affiliations

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

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27381763

Citation

Wakamatsu, Junichiro, et al. "Taste-Active Maillard Reaction Products in Roasted Garlic (Allium Sativum)." Journal of Agricultural and Food Chemistry, vol. 64, no. 29, 2016, pp. 5845-54.
Wakamatsu J, Stark TD, Hofmann T. Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). J Agric Food Chem. 2016;64(29):5845-54.
Wakamatsu, J., Stark, T. D., & Hofmann, T. (2016). Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). Journal of Agricultural and Food Chemistry, 64(29), 5845-54. https://doi.org/10.1021/acs.jafc.6b02396
Wakamatsu J, Stark TD, Hofmann T. Taste-Active Maillard Reaction Products in Roasted Garlic (Allium Sativum). J Agric Food Chem. 2016 Jul 27;64(29):5845-54. PubMed PMID: 27381763.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). AU - Wakamatsu,Junichiro, AU - Stark,Timo D, AU - Hofmann,Thomas, Y1 - 2016/07/14/ PY - 2016/7/7/entrez PY - 2016/7/7/pubmed PY - 2017/4/15/medline KW - Maillard reaction KW - S-allyl-l-cysteine KW - garlic KW - kokumi KW - taste SP - 5845 EP - 54 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 64 IS - 29 N2 - In order to gain first insight into candidate Maillard reaction products formed upon thermal processing of garlic, mixtures of glucose and S-allyl-l-cysteine, the major sulfur-containing amino acid in garlic, were low-moisture heated, and nine major reaction products were isolated. LC-TOF-MS, 1D/2D NMR, and CD spectroscopy led to their identification as acortatarin A (1), pollenopyrroside A (2), epi-acortatarin A (3), xylapyrroside A (4), 5-hydroxymethyl-1-[(5-hydroxymethyl-2-furanyl)methyl]-1H-pyrrole-2-carbalde-hyde (5), 3-(allylthio)-2-(2-formyl-5-hydroxymethyl-1H-pyrrol-1-yl)propanoic acid (6), (4S)-4-(allylthiomethyl)-3,4-dihydro-3-oxo-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (7), (2R)-3-(allylthio)-2-[(4R)-4-(allylthiomethyl)-6-formyl-3-oxo-3,4-dihydropyrrolo-[1,2-a]pyrazin-2(1H)-yl]propanoic acid (8), and (2R)-3-(allylthio)-2-((4S)-4-(allylthiomethyl)-6-formyl-3-oxo-3,4-dihydropyrrolo-[1,2-a]pyrazin-2(1H)-yl)propanoic acid (9). Among the Maillard reaction products identified, compounds 5-9 have not previously been published. The thermal generation of the literature known spiroalkaloids 1-4 is reported for the first time. Sensory analysis revealed a bitter taste with thresholds between 0.5 and 785 μmol/kg for 1-5 and 7-9. Compound 6 did not show any intrinsic taste (water) but exhibited a strong mouthfullness (kokumi) enhancing activity above 186 μmol/kg. LC-MS/MS analysis showed 1-9 to be generated upon pan-frying of garlic with the highest concentration of 793.7 μmol/kg found for 6, thus exceeding its kokumi threshold by a factor of 4 and giving evidence for its potential taste modulation activity in processed garlic preparations. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/27381763/Taste_Active_Maillard_Reaction_Products_in_Roasted_Garlic__Allium_sativum__ L2 - https://doi.org/10.1021/acs.jafc.6b02396 DB - PRIME DP - Unbound Medicine ER -