Biosynthesis of 2-Methylbutyl, 2-Methyl-2-butenyl, and 2-Methylbutanoate Esters in Red Delicious and Granny Smith Apples Using Deuterium-Labeled Substrates

Rowan, Daryl D.; Lane, Heather; Allen, John M.; Fielder, Simon; Hunt, Martin

doi:10.1021/jf9508209

Cited by 127 publications

(152 citation statements)

References 24 publications

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“…They can also derive from branched-chain amino acids such as isoleucine, leucine and valine (17,18). There are reports of more than 25 aldehydes in apple (6), mostly hexanal, trans-2-hexenal and butanal.…”

Section: Volatile Aroma Compounds In Applementioning

confidence: 99%

“…Volatile compounds are synthesized from fatt y acid metabolism, amino acid metabolism, and carbohydrate metabolism (5,63,64), through the following pathways (40): (i) straight-chain aldehydes, alcohols and esters are synthesized from lipids, mainly linolenic and linoleic acids, through β-oxidation and lipoxygenase activity (8,16), (ii) branched-chain aldehydes, alcohols and esters are derived from isoleucine (17,(65)(66)(67), (iii) terpenoids are synthesized via the mevalonate pathway (63,68) and deoxyxylulose phosphate pathway (69), and (iv) phenylpropanoids are synthesized from the phenylpropanoid pathway (70).…”

Section: Biosynthesis Of Volatile Compounds In Applesmentioning

confidence: 99%

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Biochemistry of apple aroma: A review

Espino-Díaz¹,

Sepúlveda²,

González‐Aguilar

et al. 2016

Food Technol. Biotechnol.

151

134

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SummaryFlavour is a key quality att ribute of apples defi ned by volatile aroma compounds. Biosynthesis of aroma compounds involves metabolic pathways in which the main precursors are fatt y and amino acids, and the main products are aldehydes, alcohols and esters. Some enzymes are crucial in the production of volatile compounds, such as lipoxygenase, alcohol dehydrogenase, and alcohol acyltransferase. Composition and concentration of volatiles in apples may be altered by pre-and postharvest factors that cause a decline in apple fl avour. Addition of biosynthetic precursors of volatile compounds may be a strategy to promote aroma production in apples. The present manuscript compiles information regarding the biosynthesis of volatile aroma compounds, including metabolic pathways, enzymes and substrates involved, factors that may aff ect their production and also includes a wide number of studies focused on the addition of biosynthetic precursors in their production.

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Section: Volatile Aroma Compounds In Applementioning

confidence: 99%

Section: Biosynthesis Of Volatile Compounds In Applesmentioning

confidence: 99%

Biochemistry of apple aroma: A review

Espino-Díaz¹,

Sepúlveda²,

González‐Aguilar

et al. 2016

Food Technol. Biotechnol.

151

134

View full text Add to dashboard Cite

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“…The major group of compounds produced from ripe fruit of apple cultivars, such as Royal Gala, is esters (Young et al, 1996(Young et al, , 2004, including straight-chain esters derived from fatty acids (Rowan et al, 1999) and branched-chain esters derived from branchedchain amino acids (Rowan et al, 1996). Of the straightchain esters, C-6 constituents are thought to be derived via the lipoxygenase pathway from linoleic acid (Fig.…”

Section: Flavor Biosynthesismentioning

confidence: 99%

“…Branched-chain esters are characteristic of many cultivars of apple, including Royal Gala (Young et al, 1996(Young et al, , 2004. These are produced from Ile (Rowan et al, 1996), which increases in quantity in apple fruit skin during ripening (Defilippi et al, 2005a). Ile is synthesized from the amino acid Thr via five enzymatic steps.…”

Section: Flavor Biosynthesismentioning

confidence: 99%

“…In addition to contributing to the pool of alcohols, branched hydrocarbons derived from Ile can also form CoA acids. For example, in addition to the branched-chain ester 2-methyl butyl acetate, the same branched chain can form ethyl-2-methyl butanoate, the predominant branched-chain ester found in Granny Smith apples (Rowan et al, 1996). Once produced, esters are available to be hydrolyzed by esterases (EC 3.1.1.1; two NR sequences).…”

Section: Flavor Biosynthesismentioning

confidence: 99%

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Analyses of Expressed Sequence Tags from Apple

et al. 2006

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The domestic apple (Malus domestica; also known as Malus pumila Mill.) has become a model fruit crop in which to study commercial traits such as disease and pest resistance, grafting, and flavor and health compound biosynthesis. To speed the discovery of genes involved in these traits, develop markers to map genes, and breed new cultivars, we have produced a substantial expressed sequence tag collection from various tissues of apple, focusing on fruit tissues of the cultivar Royal Gala. Over 150,000 expressed sequence tags have been collected from 43 different cDNA libraries representing 34 different tissues and treatments. Clustering of these sequences results in a set of 42,938 nonredundant sequences comprising 17,460 tentative contigs and 25,478 singletons, together representing what we predict are approximately one-half the expressed genes from apple. Many potential molecular markers are abundant in the apple transcripts. Dinucleotide repeats are found in 4,018 nonredundant sequences, mainly in the 5#-untranslated region of the gene, with a bias toward one repeat type (containing AG, 88%) and against another (repeats containing CG, 0.1%). Trinucleotide repeats are most common in the predicted coding regions and do not show a similar degree of sequence bias in their representation. Bi-allelic single-nucleotide polymorphisms are highly abundant with one found, on average, every 706 bp of transcribed DNA. Predictions of the numbers of representatives from protein families indicate the presence of many genes involved in disease resistance and the biosynthesis of flavor and health-associated compounds. Comparisons of some of these gene families with Arabidopsis (Arabidopsis thaliana) suggest instances where there have been duplications in the lineages leading to apple of biosynthetic and regulatory genes that are expressed in fruit. This resource paves the way for a concerted functional genomics effort in this important temperate fruit crop.

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Plant Volatiles

Qualley

Dudareva

2010

Encyclopedia of Life Sciences

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Plants produce an amazing number of chemical compounds that can disperse in the air at ambient temperature. These plant volatiles have served mankind, perhaps since pre‐Neolithic times, as perfumes and flavour compounds. In nature, these compounds attract pollinators and seed dispersers, protect plants through repulsion or intoxication of attacking herbivores, entice predator or parasitoid insects that prey on herbivores, prime defences of neighbouring plants against imminent attack, confer antimicrobial properties critical to defence against pathogens, and mitigate oxidative stresses. Plant volatiles are typically classified into four major categories: terpenoids, fatty acid derivatives, amino acid derivatives and phenylpropanoid/benzenoid compounds, though a number of species‐ or genus‐specific volatile compounds, such as those found in select species of Alliaceae and Brassicaceae, fall outside these categories. This enormous variety is represented by more than 1700 compounds from 90 species. Key Concepts: Plant volatiles are critical in the attraction of pollinators and seed dispersers. Plants use volatiles to protect themselves from pests and pathogens. Plants under herbivore attack can alert neighbouring plant species, priming their chemical defences. Plant volatiles are classified according to their metabolic origins as terpenoids, phenylpropanoids/benzenoids, fatty acid derivatives and amino acid derivatives. Biosynthesis of plant volatiles is spatially, developmentally and temporally regulated. Modern techniques for the collection and trapping of plant volatiles (SPME, dynamic headspace sampling) provide sensitive and representative samples for analysis. Plant volatiles serve humankind as perfumes and aroma compounds, natural flavour constituents, food additives/preservatives, and chemotherapeutics and anaesthetics.

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Biosynthesis of 2-Methylbutyl, 2-Methyl-2-butenyl, and 2-Methylbutanoate Esters in Red Delicious and Granny Smith Apples Using Deuterium-Labeled Substrates

Cited by 127 publications

References 24 publications

Biochemistry of apple aroma: A review

Biochemistry of apple aroma: A review

Analyses of Expressed Sequence Tags from Apple

Plant Volatiles

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