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Use of Alkyl Gallates as Glyoxal and Methylglyoxal Inhibitors

A technology of alkyl gallate and methylglyoxal, which is applied in the fields of application, edible oil/fat, anti-toxic agent, etc., can solve the problem of undiscovered alkyl gallate, etc., and achieve the effect of preventing harm

Active Publication Date: 2019-09-20
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, research on alkyl gallate at home and abroad mainly focuses on antioxidant activity, antibacterial properties, and analysis and detection methods, and it has not been found that alkyl gallate can inhibit the harmful intermediate product 1,2-dicarbonyl compound of the Maillard reaction. Research

Method used

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  • Use of Alkyl Gallates as Glyoxal and Methylglyoxal Inhibitors
  • Use of Alkyl Gallates as Glyoxal and Methylglyoxal Inhibitors
  • Use of Alkyl Gallates as Glyoxal and Methylglyoxal Inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1PG / OG / DG and adduct product MG-PG / MG-OG / MG-DG are to the inhibitory activity of GO

[0029] 1) Experimental materials and instruments

[0030] MG-PG (the adduct product of PG and GO, HPLC, ≥90%), MG-OG (the adduct product of OG and GO, HPLC, ≥90%), (the adduct product of DG and GO, MG -DG, HPLC, ≥90%) are all self-made in the laboratory.

[0031] PG, OG, and DG were all purchased from Shanghai Sinopharm Chemical Reagent Co., Ltd.; GO (40% aqueous solution) was purchased from Sigma-Aldrich Company of the United States; 7820A gas chromatography (Agilent Company of the United States).

[0032] 2) Experimental steps

[0033]Add 2 mL of PG (or OG, DG, MG-PG, MG-OG, MG-DG) methanol solution with a concentration of 1 mmol / L, 2 mL of PBS with a concentration of 1 mmol / L (0.2 mol / L, pH7. 0) The prepared GO solution was vortex mixed, reacted in an oil bath at 100°C for 5, 10, 15, and 30 minutes, and then quickly took it out and placed it in an ice-water bath to coo...

Embodiment 2M

[0036] Example 2 Purification and structural research of MG-PG, MG-OG, MG-DG, MM-PG

[0037] 1) Experimental materials and instruments

[0038] AVANCE 400MHz nuclear magnetic resonance instrument (Bruker); 1290 / 6460 liquid chromatography-mass spectrometry (Agilent, USA).

[0039] 2) Experimental steps

[0040] The molar ratio of PG to GO is 1:10 for the reaction, and the C 18 The chromatographic column is purified to obtain MG-PG (MG-OG, MG-DG, MM-PG are prepared in the same way), and the molecular weight is analyzed by LC-MS; 1D-NMR 1 H, 13 C, 2D-NMR 1 H- 13 C HMQC and HMBC for structural analysis. The structural analysis of MG-OG, MG-DG, and MM-PG is the same as above.

[0041] 3) Experimental results

[0042] The prepared MG-PG was determined by liquid chromatography-mass spectrometry, and in negative ion mode, m / z was 269[M-H] - , than m / z211[M-H] of PG - More than 58 (MW GO is 58), and 269[M-H] in MS / MS - The main fragment ion peak is m / z 211, missing a GO mol...

Embodiment 3

[0047] Example 3 Determination of PG / OG / DG and the addition product MG-PG / MG-OG / MG-DG inhibiting the formation of GO in the amino acid-sugar system under high temperature conditions

[0048] 1) Experimental materials and instruments

[0049] Arginine (Arg, analytically pure) and glucose (analytical pure) were purchased from Shanghai Biological Biotechnology Co., Ltd.; 7820A gas chromatograph (Agilent, USA).

[0050] 2) Experimental steps

[0051] Add 2 mL of Arg solution and glucose solution prepared in PBS (0.2 mol / L, pH 7.0) with a concentration of 180 mmol / L to the explosion-proof vial in turn, and dilute the PBS to a final volume of 6 mL. After vortex mixing, place in an oil bath at 170°C, react for 0, 5, 15, 30, and 40 minutes respectively, then quickly take it out and place it in an ice-water bath to cool. A 1 mL sample was taken for derivatization treatment, and the GO content was detected by gas chromatography. Three sets of parallels were made for each sample.

[...

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PUM

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Abstract

The invention discloses applications of an alkyl gallate and an addition compound thereof as glyoxal (GO) and methylglyoxal (MGO) inhibitors. The problems in the prior art are solved, the alkyl gallate is capable of controlling the contents of GO and MGO effectively, avoiding induction of protein glycosylation by GO and MGO and generation of irreversible harmful substance advanced glycation end products (AGEs). The alkyl gallate can be taken as a GO and MGO inhibitor to inhibit generation of GO and MGO in vivo and in food processing process, so that harm caused by GO and MGO on human body is avoided.

Description

technical field [0001] The invention discloses the application of alkyl gallate as an inhibitor of glyoxal and methylglyoxal, and belongs to the technical field of new uses of antioxidants. Background technique [0002] Both glyoxal (GO) and methylglyoxal (MGO) are 1,2-dicarbonyl active compounds, which are highly active glycosylation factors, 200-50,000 times more reactive than glucose, and are responsible for the formation of advanced sugar groups. Precursors of chemical end products (AGEs). AGEs mainly refer to a class of stable polymers formed by glucose and protein or amino acid through the Maillard reaction pathway without the participation of enzymes. The research results prove that the formation and accumulation of AGEs in internal organs, tissues and plasma can lead to chronic diseases such as diabetes complications, cardiovascular and cerebrovascular diseases and senile dementia. Therefore, taking 1,2-dicarbonyl compounds as the target of protein glycosylation an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/235A61P3/10A61P35/00A61P25/28A61P9/10A61P29/00A61P39/00A23L33/10A23D9/04A23L13/10A23L13/40A23L13/70A21D2/14
Inventor 吕丽爽王佳琦侯玉崔恒清王茜
Owner NANJING NORMAL UNIVERSITY
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