Formation of Reducing Substances in the Maillard Reaction between D-Glucose and γ-Aminobutyric Acid

Ninomiya, Masaki; Matsuzaki, Toshiake; Shigematsu, Hitoshi

doi:10.1271/bbb.56.806

Cited by 23 publications

(15 citation statements)

References 3 publications

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“…In comparison to 27 , the 1 H NMR spectrum of compound 28 showed an additional signal of a hydroxymethyl group (H 2 –C(6)) at 4.64 ppm, while the pyrrole proton at C(5) was lacking. Although isolated earlier as a Maillard reaction product from carbohydrate/aminobutyric acid model reactions, , 4-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]butyric acid ( 28 ), isolated from fraction IIA-8-10, has not been previously reported as a constituent of beer (Figure ).…”

Section: Resultssupporting

confidence: 73%

Activity-Guided Identification of in Vitro Antioxidants in Beer

Spreng

Hofmann

2018

J. Agric. Food Chem.

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In order to locate the key antioxidants contributing to oxidative stability of beer, activity-guided fractionation in combination with the oxygen radical absorbance capacity (ORAC) assay, hydrogen peroxide scavenging (HPS) assay, and linoleic acid (LA) assay was applied to a pilsner-type beer. LC-MS and 1D/2D NMR experiments led to the identification of a total of 31 antioxidants, among which 3-methoxy-4-hydroxyphenyl-β-d-glucopyranoside (tachioside), 4-(2-formylpyrrol-1-yl)butyric acid, 4-[2-formyl-5-(hydroxymethyl)pyrrol-1-yl]butyric acid, n-multifidol-3-O-β-d-glucoside, quercetin-3-O-(6″-malonyl)-glucoside, 4-feruloylquinic acid, syringaresinol, saponarin, and hordatines A-C have been isolated from beer for the first time. On a molar comparison, the hordatines A-C, saponarin, and quercetin-3-O-β-d-(6″-malonyl)glucoside were evaluated with the highest antioxidant activities of all identified beer constituents, reaching values of 10-17.5 (ORAC), 2.0-4.1 (HPS), and 1.1-6.1 μmol TE/μmol (LA) for hordatines A-C.

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Section: Resultssupporting

confidence: 73%

Activity-Guided Identification of in Vitro Antioxidants in Beer

Spreng

Hofmann

2018

J. Agric. Food Chem.

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“…Since the formyl pyrrole structure is formed from d-glucose and γ-aminobutyric acid via the Maillard reaction [10,15], there is some discussion on whether these attractive ingredients are produced chemically or by a biosynthetic route. The present study further supported that the formyl pyrrole ingredients are generally found in a variety of natural resources and, thus, further studies on the biosynthetic mechanisms are needed for clarification.…”

Section: Discussionmentioning

confidence: 99%

Identification of a Novel Pyrrole Alkaloid from the Edible Mushroom Basidiomycetes-X (Echigoshirayukidake)

et al. 2020

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Three pyrrole alkaloid derivatives were isolated from the edible mushroom Basidiomycetes-X (Echigoshirayukidake) by water extraction followed by ethyl acetate fractionation. The chemical structures determined by MS and NMR were 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanoic acid (compound I), 4-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] butanamide (compound II), and 5-(hydroxymethyl)-1H-pyrrole-2-carboxaldehyde (compound III). Compound I was found to be the major component, followed by compound II, and compound III was the minor component. The dry powder of Basidiomycetes-X contained approximately 825 μg g−1 compound I and 484 μg g−1 compound II. Compound II was found to be a novel pyrrole aldehyde homologue not previously reported and thus is a specific component of this mushroom.

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“…This indicates that these melanoidins prepared without pH control were unstable during a long period of storage, even if frozen. While the reducing activity of melanoidin depends on reductones (Kato, 1991;Hayase, 1997), pyrrole compounds also have reducing activity (Ninomiya, Matsuzaki, & Shigematsu, 1992), and may have been involved in the melanoidin stability. The greater stability of the melanoidins prepared with pH control might therefore have been due to more pyrrole compounds like P2 and P3 as well as reductone.…”

Section: Discussionmentioning

confidence: 99%