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DDMP
FOOD CONTROL · 2022 · IF 6.652

Rapid and sensitive quantitation of DDMP (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) in baked red jujubes by HS-SPME-GC-MS/MS

Yening Qiao,Jinfeng Bi,Qinqin Chen,Xinye Wu,Xinwen Jin,Min Gou,Xinrui Yang,Giorgia Purcaro

Baked red jujube is a common food ingredient used to enrich the nutritional value and enhance the aroma. DDMP (2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one) with intense bitterness and potential toxicity may be present in several baked red jujube-based products but there are no well-defined methods to measure it quickly, sensitively, and accurately. Headspace solid-phase microextraction with gas chromatography-tandem mass spectrometry (HS-SPME-GC-MS/MS) was applied for the analysis of DDMP. The standard curve was linear between the concentrations of 0.01 and 100 μg/mL, with a limit of detection at 0.1 ng/g that below the sensory threshold of DDMP (2.06 μg/g). Five cultivars of baked red jujubes from China were evaluated with the method for DDMP content (4.55–46.50 μg/g). The results indicated that jujube cultivars with a higher molar ratio of proline to glucose, lower moisture content, and stronger ability to resist water stress should be avoided from baking to modulate the formation of DDMP.

CAS / MDL: 110-54-3
研究领域: 食品科学 · 分析化学 · 植物学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2019 · IF 3.714

Formation of 2,3-dihydro-3,5-Dihydroxy-6-Methyl-4(H)-Pyran-4-One (DDMP) in glucose-amino acids Maillard reaction by dry-heating in comparison to wet-heating

He Li,Xiang-Yi Tang,Chun-Jian Wu,Shu-Juan Yu

The 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) is one of the Mallard reaction product with intense bitter and strong antioxidant activity . Insight into DDMP formation pathways is important to manage Maillard reaction products quality. In this work, wet- and dry-heating glucose-amino acid model reactions were investigated to understand the DDMP formation pathways. Lysine and proline facilitated the DDMP generation in wet- and dry-heating system, respectively, suggesting the reaction intensity and amino acid properties are primary factors mediating DDMP generation. Fundamental mechanism on DDMP formation or inhibition was evaluated via quantitatively monitoring enolization products, which suggested that the formation of DDMP was facilitated at lower moisture content condition caused by more 1-deoxyglucosone (1-DG) generation via 2,3-enolization. However, increasing moisture content resulted in the decay of DDMP because of the transformation of 2,3-enolization to 1,2-enolization, which inhibited DDMP generation but transformed to form 5-hydroxymethylfurfural (HMF).

CAS / MDL: 393-75-9 67-47-0
研究领域: 食品科学 · 生物化学
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FLAVOUR AND FRAGRANCE JOURNAL · 2021 ·Vol. 36 ·期 3 ·404-411 · IF 2.576

Identification of bitter-taste compounds in class-III caramel colours

He Li,Wen-Chao Zhang,Xiang-Yi Tang,Chun-Jian Wu,Shu-Juan Yu,Zi-Qing Zhao

Caramel colours become one of the most widely used colorings in various foods and beverages due to their total miscibility with water and great coloring properties by containing colloidal aggregates. Bitterness in caramel colours can negatively influence their acceptability. The sequential solvent extraction (SSE) and semi-preparative liquid chromatography (SP-LC) combined with the taste dilution analysis were applied to identify the most intense bitter-tasting compounds in class-III caramel colours. Four main compounds with the highest bitterness intensity were isolated and structurally elucidated based on high resolution-electrospray ionization-mass spectrum (HR-ESI-MS), nuclear magnetic resonance (NMR) spectroscopy and gas chromatography-mass spectrum (GC-MS): 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP), 5-(hydroxymethyl) furfural (HMF), furfural and 5-methylfurfural (MF). The threshold concentrations of DDMP, HMF, furfural and MF were 14.3, 30.0, 4.4 and 17.5μmol L −1 , respectively. Furthermore, two volatile bitter compounds were identified: [5-(di-methoxymethyl) furan-2-yl] methanol (DMFM) and 2,3,4,4-tetramethyl-pentane-1,3-diol (TMP). Based on the composition of the caramel colours and the structures of these compounds, Maillard reaction was supported to generate these bitter compounds in caramel colour-III.

CAS / MDL: 98-01-1 67-47-0
研究领域: 食品科学 · 化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

Insights into the Regulation Effects of Certain Phenolic Acids on 2,3-Dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one Formation in a Microaqueous Glucose–Proline System

He Li,Chun-Jian Wu,Xiang-Yi Tang,Shu-Juan Yu

The control of 2,3-dihydro-3,5-dihydroxy-6-methyl-4(H)-pyran-4-one (DDMP) formation in the Maillard reaction is important to improve the thermally treated food quality as a result of its intense bitterness and potential toxicity. In this work, phenolic acids, such as gallic, protocatechuic, caffeic, and ferulic acids, were applied to modulate DDMP formation in a microaqueous glucose–proline model. The formation of DDMP was inhibited at low concentrations (from 0.1 to 5.0 mM) while enhanced at 10.0 mM gallic, protocatechuic, and caffeic acids. Ferulic acid always inhibited DDMP formation as a result of the absence of catechol groups on its benzene ring. The result indicated that the control of DDMP formation depended upon the concentration and chemical structures of phenolic acids, such as the number of hydroxyl groups. Further studies indicated that the hydroxyl distribution of phenolic acids regulated the peroxide formation in the model reaction system and further changed the development of the oxidation reaction, which affected the degradation of glucose via caramel or Maillard reaction, Amadori rearrangement product oxidation, and 1-deoxyglucosone degradation to form the intermediates.

CAS / MDL: 393-75-9
研究领域: 食品科学 · 生物化学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2022 ·Vol. 102 ·期 15 ·7249-7258 · IF 4.125

Effects of moisture content on the enolization products formation in glucose–proline Maillard reaction models

He Li,Fu-Han Yang,Wen-Chao Zhang,Zhi-Jun Zhang,Shu-Juan Yu

BACKGROUND 2,3-Dihydro-3,5-dihydroxy-6-methyl-4( H )-pyran-4-one (DDMP) and 5-hydroxymethylfurfural (HMF) are two main enolization products in the Maillard reaction and found in some foodstuffs. For many years, whether they are functional or noxious to human health has been a matter of debate. Thus, insight into their formation pathways is important to manage Maillard reaction products. In this study, DDMP and HMF were quantified and compared with regard to their formation and degradation in the d -glucose and l -proline Maillard reaction models using different moisture contents (0, 0.1, 0.5, 1.0, and 4.0 mL) at 150 °C for various heating times. RESULTS DDMP was predominantly generated in dry or low water-content heating models along with n increased 1-deoxyglucosone (1-DG) generation via 2,3-enolization. However, increasing moisture content resulted in a decay of reaction intensity, 1-DG, and DDMP due to a change in the reaction mechanism from 2,3-enolization to 1,2-enolization, which facilitated 3-deoxyglucosone (3-DG) and HMF formation. CONCLUSION Increased moisture content in glucose–proline models reduced reaction intensity and also inhibited DDMP and facilitated HMF formation by promoting the pathway change from 2,3-enolization to 1,2-enolization to generate more 3-DG. A water content of 1.0 mL was identified as a critical value, from which the 1,2-enolization became a primary pathway occurring in the Maillard reaction. © 2022 Society of Chemical Industry.

研究领域: 食品科学 · 生物化学
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