Occurrence, Formation, Stability, and Interaction of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone

Xiao, Qing; Huang, Qingrong; Ho, Chi‐Tang

doi:10.1021/acsfoodscitech.1c00011

Cited by 12 publications

(12 citation statements)

References 99 publications

(211 reference statements)

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“…This corresponded to an increase of 500% of which only 1% could be explained by a direct transfer of HDMF from the LME. Thus, 99% of the additional HDMF in the crumb of the bread with LME addition must have been formed from LME-derived precursors, presumably reducing sugars or reactive C 3 intermediates of the Maillard reaction formed during LME production. , Similar to the crust, about half of the odorants ( 5a and below in Table , crumb) were characterized by rather small differences between the reference bread and the bread with LME addition in combination with negligible amounts added with the LME.…”

Section: Resultsmentioning

confidence: 97%

Impact of Malt Extract Addition on Odorants in Wheat Bread Crust and Crumb

Rögner

Steinhaus

2021

J. Agric. Food Chem.

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Application of gas chromatography–olfactometry and aroma extract dilution analysis to the volatiles isolated from (1) crust and (2) crumb of a wheat bread made with the addition of a dark liquid malt extract (LME) to the dough and (3) crust and (4) crumb of a reference bread made without addition resulted in the identification of 23 major odorants. Their quantitation followed by the calculation of odor activity values (OAV = ratio of concentration to odor threshold value) suggested that LME addition influenced the aroma of the bread predominantly by increasing seasoning-like smelling sotolon in crust and crumb, and caramel-like smelling compounds maltol and 4-hydroxy-2,5-dimethylfuran-3(2H)-one (HDMF) in the crumb. The increase in sotolon and maltol was explainable by direct transfer from the LME to the bread, whereas HDMF must have been formed from LME-derived precursors. This difference needs to be considered in the targeted optimization of LMEs for bread making.

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Section: Resultsmentioning

confidence: 97%

Impact of Malt Extract Addition on Odorants in Wheat Bread Crust and Crumb

Rögner

Steinhaus

2021

J. Agric. Food Chem.

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“…Although being found in many teas such as Japanese roasted barley tea ( Mugi-cha ), Chinese raw pu-erh tea, and Indian Darjeeling black tea, 4-hydroxy-2,5-dimethyl-3(2 H )-furanone was previously reported as a key odorant in Chinese Jingshan and Laoshan green tea based on high OAVs. , Very recently, we decoded 4-hydroxy-2,5-dimethyl-3(2 H )-furanone as the specific caramel-like aroma compound in Dahongpao , a famous Chinese Wuyi rock tea . Maillard reaction and β- d -glucopyranoside hydrolysis are suggested as two generation mechanisms of 4-hydroxy-2,5-dimethyl-3(2 H )-furanone in many heat-processed foodstuffs (e.g., wheat bread crust, and popcorn) and berries, respectively. , Further, many thermally induced alkylpyrazines including 2,3-diethyl-5-methylpyrazine (OAV 110), 2-ethyl-3,5-dimethylpyrazine (30), 2-ethyl-5-methylpyrazine (4.4), 2-ethyl-6-methylpyrazine (2.4), and trimethylpyrazine (1.8) were found to contribute a roasty/nutty odor impression to the overall aroma quality of the LYT infusion because their amounts in the tea infusion were higher than the respective odor threshold in water. Although the aforementioned alkylpyrazines have been reported several times in LYT, ,, it is the first time their real contribution to the overall aroma characteristic was evaluated by GC-O and quantitation, as well as aroma recombination experiment.…”

Section: Resultsmentioning

confidence: 99%

Insights into the Key Odorants in Large-Leaf Yellow Tea (Camellia sinensis) by Application of the Sensomics Approach

Zhai

Pei

et al. 2022

J. Agric. Food Chem.

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Large-leaf yellow tea (LYT) is a yellow tea product with a specific aroma characteristic and is enjoyed with increasing enthusiasm in China. However, its key odorants are still unknown. In this study, 46 odorants in the headspace and vacuum-distillate of the tea infusion were identified via aroma extract dilution analysis. Sixteen compounds were newly found in LYT infusion. They were present in the highest flavor dilution factors together with 2-ethyl-3,5-dimethylpyrazine. All odorants were quantitated to evaluate their own odor activity values (OAVs). High OAVs were found for 2-methylbutanal (malty, 210), (E,E)-2,4-heptandienal (fatty/flowery, 170), 2-methylpropanal (malty, 120) and 2,3-diethyl-5-methylpyrazine (earthy/roasty, 110). An aroma recombinate consisting of 17 odorants (all OAVs ≥ 1) in an odorless nonvolatile LYT matrix mimicked the overall aroma of the original infusion, verifying the successful characterization of key aroma components in a LYT beverage. The knowledge of key odorants obtained showed potential for simplifying industrial flavor optimization of the LYT product.

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“…The 3(2 H )-furanone structure is widely distributed in nature and known to be synthesized in several different manners. Examples include modifications of sugar molecules and P450-mediated oxidative heterocyclization, as seen in the biosynthesis of griseofulvin and gregatin A. , Unlike the SetF-catalyzed reaction, most of the known mechanisms for 3(2 H )-furanone formation do not involve a complicated rearrangement reaction. The furanone synthesis in the scopranone pathway, for which the detailed reaction mechanism has yet to be established, is somewhat similar to the reaction by SetF, as the furanone moiety is formed via the rearrangement of a pyrone provided by PKS .…”

Section: Resultsmentioning

confidence: 99%

Molecular and Computational Bases for Spirofuranone Formation in Setosusin Biosynthesis

et al. 2021

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The 3(2H)-furanone unit is observed in many biologically active natural products, as represented by the antifungal medication griseofulvin. Setosusin (1) is a fungal meroditerpenoid featuring a unique spiro-fused 3(2H)-furanone moiety; however, the biosynthetic basis for spirofuranone formation has not been investigated since its isolation. Therefore, in this study we identified the biosynthetic gene cluster of 1 in the fungus Aspergillus duricaulis CBS 481.65 and elucidated its biosynthetic pathway by heterologous reconstitution of related enzyme activities in Aspergillus oryzae. To understand the reaction mechanism to afford spirofuranone, we subsequently performed a series of in vivo and in vitro isotope-incorporation experiments and theoretical calculations. The results indicated that SetF, the cytochrome P450 enzyme that is critical for spirofuranone synthesis, not only performs the epoxidation of the polyketide portion of the substrate but also facilitates the protonation-initiated structural rearrangement to yield 1. Finally, a mutagenesis experiment using SetF identified Lys303 as one of the potential catalytic residues that are important for spirofuranone synthesis.

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Occurrence, Formation, Stability, and Interaction of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone

Cited by 12 publications

References 99 publications

Impact of Malt Extract Addition on Odorants in Wheat Bread Crust and Crumb

Impact of Malt Extract Addition on Odorants in Wheat Bread Crust and Crumb

Insights into the Key Odorants in Large-Leaf Yellow Tea (Camellia sinensis) by Application of the Sensomics Approach

Molecular and Computational Bases for Spirofuranone Formation in Setosusin Biosynthesis

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