Dicarbonyls, Reductones, and Heterocyclics Produced by Reactions of Reducing Sugars with Secondary Amine Salts

Hodge, John E.; Fisher, Benjamin E.; Nelson, Earl C.

doi:10.1080/00960845.1963.12006704

Cited by 47 publications

(26 citation statements)

References 19 publications

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“…HDMF was first reported as a product of the Maillard reaction (Hodge et al, 1963) and was subsequently isolated from different fruits, including pineapple, strawberry, and tomato (Rodin et al, 1965;Buttery et al, 2001;Ubeda et al, 2012;Schwab, 2013). HDMF exhibits a caramel-like aroma similar to that of its structural homologs HMF and EHMF, which were identified in tomato and melon fruits (Lignou et al, 2014), respectively; however, the biogenetic pathways of these compounds remain unknown.…”

Section: Glucosylation Of Volatile Metabolites In Strawberrymentioning

confidence: 99%

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

et al. 2016

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ORCID IDs: 0000-0002-7852-1194 (C.S.); 0000-0002-9753-3967 (W.S.).Strawberries emit hundreds of different volatiles, but only a dozen, including the key compound HDMF [4-hydroxy-2,5-dimethyl-3(2H)-furanone] contribute to the flavor of the fruit. However, during ripening, a considerable amount of HDMF is metabolized to the flavorless HDMF b-D-glucoside. Here, we functionally characterize nine ripening-related UGTs (UDPglucosyltransferases) in Fragaria that function in the glucosylation of volatile metabolites by comprehensive biochemical analyses. Some UGTs showed a rather broad substrate tolerance and glucosylated a range of aroma compounds in vitro, whereas others had a more limited substrate spectrum. The allelic UGT71K3a and b proteins and to a lesser extent UGT73B24, UGT71W2, and UGT73B23 catalyzed the glucosylation of HDMF and its structural homolog 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone. Site-directed mutagenesis to introduce single K458R, D445E, D343E, and V383A mutations and a double G433A/I434V mutation led to enhanced HDMF glucosylation activity compared to the wild-type enzymes. In contrast, a single mutation in the center of the plant secondary product glycosyltransferase box (A389V) reduced the enzymatic activity. Down-regulation of UGT71K3 transcript expression in strawberry receptacles led to a significant reduction in the level of HDMF-glucoside and a smaller decline in HDMF-glucoside-malonate compared with the level in control fruits. These results provide the foundation for improvement of strawberry flavor and the biotechnological production of HDMF-glucoside.

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Section: Glucosylation Of Volatile Metabolites In Strawberrymentioning

confidence: 99%

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

et al. 2016

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“…Were identified already known substances, arising from Maillard reactions, such as: 2-hydroxy-3-methyl-2-cyclopenten-1-one (cyclotene) formed from the less basic Amadori intermediates [14]; 3-hydroxy-2-methyl-4H-pyran-4-one (maltol) from thermal degradation of substituted glucose-4-O structures [15]; 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP); 4,5-dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone (pantolactone) formed during alcoholic fermentation due to the action of a reductase [16]; 3,5-dihydroxy-2-methyl-4H-pyran-4-one (DMP) byproduct of heating maltose in the presence of glycine; as compounds which contribute to the "toasty" and "caramel" aroma. Fig.…”

Section: Enolic Compoundsmentioning

confidence: 99%

Changes in volatile composition of Madeira wines during their oxidative ageing

Câmara

Alves²,

Marques

2006

Analytica Chimica Acta

165

145

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The influence of the age in the volatile composition of Madeira wines made with Boal, Malvazia, Sercial and Verdelho varieties and aged in oak barrel during 1, 11 and 25 years old was been studied. For this purpose, the evolution of volatile compounds: higher alcohols, ethyl esters, fatty acids, furan compounds, enolic compounds, γ-lactones, dioxanes and dioxolanes, of the four most utilised varieties were determined using liquid-liquid extraction with dichloromeihane. Octan-3-ol was used as internal standard. The wines made with these varieties showed great differences in sugar content and small variations on pH and alcoholic degree.The results show that during ageing, the concentration of fatty acids ethyl esters, acetates and fatty acids decrease significantly contrarily to the great increase of ethyl esters of diprotic acids. There is a strong correlation between sotolon, 2-furfural, 5-methyl-2-furfural, 5-hydroxymethyl-2-furfural and 5-ethoxymethyl-2-furfural with wine ageing. These findings indicate that these compounds can be used as ageing wine markers. Among the molecules studied, sotolon [3-hydroxy-4,5-dimethyl-2(5H)-furanone] was one of the few molecules present in concentrations above the perception threshold in Madeira wines. 5-Eihoxymethyl-2-furfural formed from 5-hydroxymethyl-2-furfural and 2-furfural, derived from sugars, are also involved in the aroma of sweet fortified white wines aged in oxidative conditions. The sensory properties change significantly after long periods of conservation.

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“…HDMF was first reported as a product of the Maillard reaction (Hodge et al, 1963), and it was then isolated from pineapple (Ananas comosus) (Rodin et al, 1965), strawberry (Ohloff, 1969), and a number of different fruits . The methyl ether DMMF, first detected in pineapple (Willhalm et al, 1965), was also identified as an aroma component of a multitude of fruits, such as overripe strawberry, mango (Mangifera indica), and arctic bramble (Rubus arcticus) Schwab and Roscher, 1997).…”

Section: Introductionmentioning

confidence: 99%

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

Raab

López‐Ráez

Klein³

et al. 2006

Plant Cell

161

159

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The flavor of strawberry (Fragaria 3 ananassa) fruit is dominated by an uncommon group of aroma compounds with a 2,5-dimethyl-3(H)-furanone structure. We report the characterization of an enzyme involved in the biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol), the key flavor compound in strawberries. Protein extracts were partially purified, and the observed distribution of enzymatic activity correlated with the presence of a single polypeptide of ;37 kD. Sequence analysis of two peptide fragments showed total identity with the protein sequence of a strongly ripeninginduced, auxin-dependent putative quinone oxidoreductase, Fragaria 3 ananassa quinone oxidoreductase (FaQR). The open reading frame of the FaQR cDNA consists of 969 bp encoding a 322-amino acid protein with a calculated molecular mass of 34.3 kD. Laser capture microdissection followed by RNA extraction and amplification demonstrated the presence of FaQR mRNA in parenchyma tissue of the strawberry fruit. The FaQR protein was functionally expressed in Escherichia coli, and the monomer catalyzed the formation of HDMF. After chemical synthesis and liquid chromatography-tandem mass spectrometry analysis, 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone was confirmed as a substrate of FaQR and the natural precursor of HDMF. This study demonstrates the function of the FaQR enzyme in the biosynthesis of HDMF as enone oxidoreductase and provides a foundation for the improvement of strawberry flavor and the biotechnological production of HDMF.

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Dicarbonyls, Reductones, and Heterocyclics Produced by Reactions of Reducing Sugars with Secondary Amine Salts

Cited by 47 publications

References 19 publications

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

Glucosylation of 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, the Key Strawberry Flavor Compound in Strawberry Fruit

Changes in volatile composition of Madeira wines during their oxidative ageing

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

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