Changes in the Chemical Composition of Concord Grapes Grown in Ontario During Ripening in the 1970 Season

Fuleki, Tibor

doi:10.4141/cjps72-149

Cited by 12 publications

(5 citation statements)

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“…Methylanthranilate, found in grapes, is a volatile aromatic compound formed by esterification between anthranilate and methanol. 12 The formation of methylanthranilate is catalyzed by anthraniloyl-coenzyme A (CoA):methanol acyltransferase (AMAT). 13 Various esters have been synthesized using microorganisms; the enzymes for esterification use various compounds that are available in the environment.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli

Kim

Sim

et al. 2020

J. Agric. Food Chem.

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Hydroxybenzoic acids (HBAs) such as 4-hydroxybenzoic acid (4-HBA) and 3,4-dihydroxybenzoic acid (DHB; protocatechuic acid) and its ester with methanol (methylparaben [MP]) are known to have various functional biological properties, including antibacterial, anticancer, antidiabetic, antiaging, antiviral, and anti-inflammatory activities. Since these compounds are widely used in cosmetic, food, and pharmaceutical industries, the use of renewable feedstocks for the production of HBAs is an area of growing interest. In this study, we used Escherichia coli to synthesize these three hydroxybenzoic acid derivatives (4-HBA, DHB, and MP). We overexpressed ubiC in E. coli to synthesize 4-HBA from chorismate, a substrate that is produced by the shikimate pathway in E. coli. For the synthesis of DHB, an additional gene (pobA) was introduced, while hbad and EHT1 were co-expressed to synthesize MP. To supply more chorismate, we introduced the shikimate gene module construct and selected the best construct for increased yields. Using this approach, 723.5 mg/L 4-HBA, 942.0 mg/L DHB, and 347.7 mg/L MP were synthesized. Our study showed that the shikimate gene module constructs can be applicable to increase the yields of HBA derivatives in HBA-tolerant microorganisms.

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Section: ■ Introductionmentioning

confidence: 99%

“…In plants, some volatile aromatic compounds are esters. Methylanthranilate, found in grapes, is a volatile aromatic compound formed by esterification between anthranilate and methanol . The formation of methylanthranilate is catalyzed by anthraniloyl-coenzyme A (CoA):methanol acyltransferase (AMAT) .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli

Kim

Sim

et al. 2020

J. Agric. Food Chem.

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“…The genus Vitis comprises over 50 species that include the commercially important Vitis vinifera and Vitis labrusca (Concord grapes) that are widely grown for production of wine and grape juice, respectively. The aroma of different grape species consists of many volatile organic compounds, including methyl anthranilate that is responsible for the characteristic aroma of Concord grapes (Power and Chestnut, 1921; Fuleki, 1972) and is the main component giving character to the odor of the very popular Welch's grape juice. Several volatile odor‐active compounds (anthranilate and its methyl ester, furaneol and its methyl ester) implicated in the ‘foxy’ odor character of Concord grapes have been shown to accumulate at the onset of ripening (Shure and Acree, 1994, 1995).…”

Section: Introductionmentioning

confidence: 99%

The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including ‘foxy’ methylanthranilate

Wang

Luca²

2005

The Plant Journal

139

112

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SummaryThe biosynthesis of methyl anthranilate, the volatile compound responsible for the distinctive 'foxy' aroma and flavor of the Washington Concord grape (Vitis labrusca), involves an alcohol acyltransferase that catalyzes the formation of methyl anthranilate from anthraniloyl-coenzyme A (CoA) and methanol. Although methanol is a poor substrate in comparison with the co-substrate, high levels of this acyltransferase (0.5% of the total protein) combined with relatively high levels of this alcohol make this reaction possible in grapes. This 449 amino acid protein belongs to the BAHD family of acyltransferases, having 58% identity with the benzoyl CoA:benzyl alcohol benzoyl transferase from Clarkia. Both native and recombinant enzymes can use a broad range of acyl-CoAs and alcohols as substrates. The ability of Concord grape alcohol acyltransferase to accept a range of different CoA esters and alcohols suggests this to be a versatile ester-forming enzyme, similar to those of other fruits that than can produce a range of fruit esters based on the supply of appropriate substrates. Expression is coordinately regulated, with transcript, protein and enzyme activities coinciding with the accumulation of methyl anthranilate that occurs after the initiation of berry ripening. The majority of acyltransferase protein in grape tissues is localized to the outer fruit mesocarp, a result consistent with the fact that methyl anthranilate is released to the external environment throughout the ripening process. Wine grapes (Vitis vinifera) that accumulate neither anthranilate nor methyl anthranilate do not express this enzyme activity nor do they accumulate this protein.

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“…This biotechnological process involves the microbial production of anthranilate (ANT), which can be subsequently converted to aniline by chemical decarboxylation. Besides aniline, ANT is also the precursor of other aromatic compounds of biotechnological interest such as methyl anthranilate (MANT) conveying the typical scent and taste of the Concord grape ( Vitis labrusca ) (Chambers et al., 2013 ; Fuleki, 1972 ; Wang & De Luca, 2005 ). Another derivative is menthyl anthranilate, which serves as a UV‐A quencher in sunscreens (Beeby & Jones, 2000 ).…”

Section: Introductionmentioning

confidence: 99%

Metabolic engineering of Corynebacterium glutamicum for the production of anthranilate from glucose and xylose

Mutz,

Brüning,

Brüsseler

et al. 2024

Microbial Biotechnology

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Anthranilate and its derivatives are important basic chemicals for the synthesis of polyurethanes as well as various dyes and food additives. Today, anthranilate is mainly chemically produced from petroleum‐derived xylene, but this shikimate pathway intermediate could be also obtained biotechnologically. In this study, Corynebacterium glutamicum was engineered for the microbial production of anthranilate from a carbon source mixture of glucose and xylose. First, a feedback‐resistant 3‐deoxy‐arabinoheptulosonate‐7‐phosphate synthase from Escherichia coli, catalysing the first step of the shikimate pathway, was functionally introduced into C. glutamicum to enable anthranilate production. Modulation of the translation efficiency of the genes for the shikimate kinase (aroK) and the anthranilate phosphoribosyltransferase (trpD) improved product formation. Deletion of two genes, one for a putative phosphatase (nagD) and one for a quinate/shikimate dehydrogenase (qsuD), abolished by‐product formation of glycerol and quinate. However, the introduction of an engineered anthranilate synthase (TrpEG) unresponsive to feedback inhibition by tryptophan had the most pronounced effect on anthranilate production. Component I of this enzyme (TrpE) was engineered using a biosensor‐based in vivo screening strategy for identifying variants with increased feedback resistance in a semi‐rational library of TrpE muteins. The final strain accumulated up to 5.9 g/L (43 mM) anthranilate in a defined CGXII medium from a mixture of glucose and xylose in bioreactor cultivations. We believe that the constructed C. glutamicum variants are not only limited to anthranilate production but could also be suitable for the synthesis of other biotechnologically interesting shikimate pathway intermediates or any other aromatic compound derived thereof.

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Changes in the Chemical Composition of Concord Grapes Grown in Ontario During Ripening in the 1970 Season

Abstract: Methyl anthranilate, soluble solids, titratable thereafter. The maximum values for the other acidity, pH, and total anthocyanin content components examined were: total anthocyan-

Cited by 12 publications

References 3 publications

Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli

Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli

The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including ‘foxy’ methylanthranilate

Metabolic engineering of Corynebacterium glutamicum for the production of anthranilate from glucose and xylose

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