Metabolism of ricinoleic acid into Î³-decalactone: Î²-oxidation and long chain acyl intermediates of ricinoleic acid in the genus<i>Sporidiobolus</i>sp.

Blin-Perrin, Caroline; Mollé, Daniel; Dufossé, Laurent; Le-Quere, Jean-Luc; Viel, Christophe VielC.; Mauvais, GeneviÃ ̈ve; Féron, Gilles

doi:10.1111/j.1574-6968.2000.tb09170.x

Cited by 21 publications

(9 citation statements)

References 19 publications

(24 reference statements)

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“…The synthesis of γ-D is not well-understood in plants. However, several microorganisms can generate γ-D from fatty-acid substrates [30] and are used as bioreactors to produce this flavor compound.…”

Section: Discussionmentioning

confidence: 99%

Identification of a strawberry flavor gene candidate using an integrated genetic-genomic-analytical chemistry approach

et al. 2014

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BackgroundThere is interest in improving the flavor of commercial strawberry (Fragaria × ananassa) varieties. Fruit flavor is shaped by combinations of sugars, acids and volatile compounds. Many efforts seek to use genomics-based strategies to identify genes controlling flavor, and then designing durable molecular markers to follow these genes in breeding populations. In this report, fruit from two cultivars, varying for presence-absence of volatile compounds, along with segregating progeny, were analyzed using GC/MS and RNAseq. Expression data were bulked in silico according to presence/absence of a given volatile compound, in this case γ-decalactone, a compound conferring a peach flavor note to fruits.ResultsComputationally sorting reads in segregating progeny based on γ-decalactone presence eliminated transcripts not directly relevant to the volatile, revealing transcripts possibly imparting quantitative contributions. One candidate encodes an omega-6 fatty acid desaturase, an enzyme known to participate in lactone production in fungi, noted here as FaFAD1. This candidate was induced by ripening, was detected in certain harvests, and correlated with γ-decalactone presence. The FaFAD1 gene is present in every genotype where γ-decalactone has been detected, and it was invariably missing in non-producers. A functional, PCR-based molecular marker was developed that cosegregates with the phenotype in F1 and BC1 populations, as well as in many other cultivars and wild Fragaria accessions.ConclusionsGenetic, genomic and analytical chemistry techniques were combined to identify FaFAD1, a gene likely controlling a key flavor volatile in strawberry. The same data may now be re-sorted based on presence/absence of any other volatile to identify other flavor-affecting candidates, leading to rapid generation of gene-specific markers.

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Section: Discussionmentioning

confidence: 99%

Identification of a strawberry flavor gene candidate using an integrated genetic-genomic-analytical chemistry approach

et al. 2014

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“…Lactones are important food additives to increase the aroma of beverages, cosmetics, chemicals, and pharmaceutical products, and are derived from the cyclization of hydroxy acids including one carbon atom and one oxygen atom . γ-Decalactone is famous for its peach and apricot flavors, which is derived from ricinoleic acid to 4-hydroxydecanoic acid through four rounds of β-oxidation, followed by spontaneous lactonization . Expression of the POX2 gene and disruption of the POX3 gene in Y. lipolytica can interrupt the degradation of ricinoleic acid to the C10 level through the β-oxidation pathway, favoring the synthesis of γ-decalactone.…”

Section: Chain-length Regulation For Even Medium-chain Acyl-coas/acps...mentioning

confidence: 99%

“…52 γ-Decalactone is famous for its peach and apricot flavors, which is derived from ricinoleic acid to 4-hydroxydecanoic acid through four rounds of β-oxidation, followed by spontaneous lactonization. 53 Expression of the POX2 gene and disruption of the POX3 gene in Y. lipolytica can interrupt the degradation of ricinoleic acid to the C10 level through the β-oxidation pathway, favoring the synthesis of γ-decalactone. Initially, Y. lipolytica was able to produce γ-decalactone using either ricinoleic acid or methyl ricinoleate, but rapid degradation of the product was observed.…”

Section: Engineering the β-Oxidationmentioning

confidence: 99%

Engineering Yarrowia lipolytica to Produce Tailored Chain-Length Fatty Acids and Their Derivatives

et al. 2022

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Microbial production of value-added chemicals derived from fatty acids is a sustainable alternative to petroleum-derived chemicals and unsustainable lipids from animals and plants. Fatty acids with different carbon chain lengths including short- (C20), with either even or odd number of carbons, have significantly different characteristics and wide applications in energy, material, medicine, and nutrition. Tailoring chain-length specificity of these compounds using metabolic engineering would be of high interest. Yarrowia lipolytica, as an oleaginous yeast, is a superior industrial chassis for the production of tailored chain-length fatty acids and their derivatives due to its hyper-oil-producing capability. In this Review, we cover metabolic engineering approaches that can lead to fatty acid chain length control in this microorganism. These approaches involve the manipulation of the fatty acid synthase, the thioesterase, the β-oxidation pathway, the elongation and desaturation pathway, the polyketide synthase-like polyunsaturated fatty acid synthase pathway, and the odd-chain fatty acids synthesis pathway. Finally, we also discuss alternative strategies that can be used in the future to tailored chain-length control.

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“…Indeed, peroxysomal β-oxidation enzymes were shown to be responsible for γ-decalactone production in other yeast strains [7,21,[27][28][29].…”

Section: Discussionmentioning

confidence: 99%

Production of γ-Decalactone by a Psychrophilic and a Mesophilic Strain of the Yeast Rhodotorula aurantiaca

Alchihab

Destain

Aguedo

et al. 2008

Appl Biochem Biotechnol

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Among 18 psychrophilic strains isolated near the Antarctic Station, the psychrophilic strain Rhodotorula aurantiaca A19 was selected for its ability of growth and gamma-decalactone production at low temperatures. The effects of temperature, initial pH, and castor oil concentration on the growth and gamma-decalactone production by a psychrophilic and a mesophilic strain of R. aurantiaca were investigated. The highest gamma-decalactone production in flasks (5.8 g/l) was obtained with the strain A19 at 14 degrees C and initial pH 7.0 in medium containing 20 g/l castor oil. On the other hand, these factors did not affect the production of gamma-decalactone by the mesophilic strain. In fermentor, a gamma-decalactone concentration of 6.6 g/l was reached with the strain A19, whereas a maximum of 0.1 g/l was obtained with the mesophilic strain. Our results suggest that the ability to synthesize gamma-decalactone is a particularity of the strain A19, since the mesophilic strain (no. 30645) produced small amounts, and the other (no. 31354) did not exhibit this property. It is, to our knowledge, the first report of gamma-decalactone production by R. aurantiaca and furthermore by a psychrophilic yeast strain. Moreover, the amount of gamma-decalactone obtained in fermentor with the strain 19 was on the order of concentrations usually described in patents.

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Metabolism of ricinoleic acid into Î³-decalactone: Î²-oxidation and long chain acyl intermediates of ricinoleic acid in the genusSporidiobolussp.

Cited by 21 publications

References 19 publications

Identification of a strawberry flavor gene candidate using an integrated genetic-genomic-analytical chemistry approach

Identification of a strawberry flavor gene candidate using an integrated genetic-genomic-analytical chemistry approach

Engineering Yarrowia lipolytica to Produce Tailored Chain-Length Fatty Acids and Their Derivatives

Production of γ-Decalactone by a Psychrophilic and a Mesophilic Strain of the Yeast Rhodotorula aurantiaca

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