Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

Dufossé, Laurent; Féron, Gilles; Latrasse, Alain; Guichard, Élisabeth; Spinnler, Henry-Éric

doi:10.1002/(sici)1520-636x(1997)9:7<667::aid-chir5>3.0.co;2-4

Cited by 16 publications

(12 citation statements)

References 27 publications

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“…S3 and S4 in the supplemental material). ␥-Dodecalactone production by baker's yeast (33), Sporidiobolus salmonicolor (34), and Sporobolomyces odorus (18) was performed at pH 7.0, 25°C, and 130 rpm in a 500-ml flask; pH 6.0, 25°C, and 250 rpm in a 500-ml flask; and 22°C and 80 rpm (pH was not described) in a 1-liter flask, respectively.…”

Section: Resultsmentioning

confidence: 83%

New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces lipofer Cells

Joo

2013

Appl Environ Microbiol

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A new biotransformation process for the production of the flavor lactone was developed by using permeabilized Waltomyces lipofer, which was selected as an efficient ␥-dodecalactone-producing yeast among 10 oleaginous yeast strains. The optimal reaction conditions for ␥-dodecalactone production by permeabilized W. lipofer cells were pH 6.5, 35°C, 200 rpm, 0.7 M Tris, 60 g/liter of 10-hydroxystearic acid, and 30 g/liter of cells. Under these conditions, nonpermeabilized cells produced 12 g/liter of ␥-dodecalactone after 30 h, with a conversion yield of 21% (wt/wt) and a productivity of 0.4 g/liter/h, whereas permeabilized cells obtained after sequential treatments with 50% ethanol and 0.5% Triton X-100 produced 46 g/liter of ␥-dodecalactone after 30 h, with a conversion yield of 76% (wt/wt) and a productivity of 1.5 g/liter/h. These values were 3.7-and 3.8-fold higher than those obtained using nonpermeabilized cells. These are the highest reported concentration, conversion yield, and productivity for the production of the bioflavor lactone.

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Section: Resultsmentioning

confidence: 83%

New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces lipofer Cells

Joo

2013

Appl Environ Microbiol

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“…Two years later, δ-decalactone and δ-jasmin lactone were also identified in cultures of this yeast [39]. Later on, γ-octalactone and γ-nonalactone were also detected in cultures of this yeast when the effect of media composition on the de novo biosynthesis of lactones by S. salmonicolor was investigated [40]. From the five γ-lactones detected in this study, the major lactones produced were cis-6-γ-dodecenolactone and γ-decalactone, while γ-octalactone and γ-nonalactone were reported for the first time [40] (Table 1).…”

Section: Sporidiobolus Salmonicolormentioning

confidence: 67%

“…The yeast S. salmonicolor, beyond its ability to produce a wide range of lactones, either through de novo biosynthesis and biotransformation, was the most important study model to this end due to its diverse fatty acid metabolism. The studies with S. salmonicolor gave important insights concerning the de novo biosynthesis process of lactones in this yeast, mainly regarding the origin of the oxygenated derivatives of fatty acids that are the reagents of β-oxidation [40]. Many studies demonstrated the biotransformation of fatty acids and hydroxy acids into lactones in this yeast.…”

Section: Sporidiobolus Salmonicolormentioning

confidence: 99%

Microbial Biosynthesis of Lactones: Gaps and Opportunities towards Sustainable Production

et al. 2021

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Lactones are volatile organic compounds widely present in foods. These chemicals are applied as flavors and fragrances in the food, cosmetics and pharmaceutical industries. Recently, the potential of lactones as green solvents and fuel precursors reinforced their role as platform compounds of future bio-based economies. However, their current mode of production needs to change. Lactones are mainly obtained through chemical synthesis or microbial biotransformation of hydroxy fatty acids. The latter approach is preferred but still needs to use more sustainable substrates. Hydroxy fatty acids are non-abundant and non-sustainable substrates from environmental, health and economic points of view. Therefore, it is urgent to identify and engineer microorganisms with the rare ability to biosynthesize lactones from carbohydrates or renewable lipids. Here, we firstly address the variety and importance of lactones. Then, the current understanding of the biosynthetic pathways involved in lactone biosynthesis is presented, making use of the knowledge acquired in microorganisms and fruits. From there, we present and make the distinction between biotransformation processes and de novo biosynthesis of lactones. Finally, the opportunities and challenges towards more sustainable production in addition to the relevance of two well-known industrial microbes, the filamentous fungus Ashbya gossypii and the yeast Yarrowia lipolytica, are discussed.

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“…When compared with other microorganisms, the chemical diversity of the γ-lactones biosynthesized by A. gossypii and the relative short time needed for their production (2 days) is noteworthy. Only three ( T. viride ; 12 days) [11], four ( S. salmonicolor ; 12 days) [12] and five ( F. poae ; 8 days) [9] γ-lactones were detected in the other reported lactone-producing fungi. Regarding the other predominant family of VOCs, the two major higher alcohols detected were 2-phenylethanol and isoamyl alcohol (Additional file 1: Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Given all of the above, the identification and engineering of microbial systems with the unusual natural ability for de novo biosynthesis of lactones from sustainable and highly accessible carbon sources, such as carbohydrates, constitutes a major challenge to this field. To the extent of our knowledge, only three microbial species were previously studied for the de novo biosynthesis of lactones: two filamentous fungi, Fusarium poae [9] and Trichoderma viride [10, 11]; and one yeast, Sporidiobolus salmonicolor [12, 13]. However, a comprehensive overview of this biosynthetic process is lacking and there is very little information regarding the genetic and enzymatic machinery involved.…”

Section: Introductionmentioning

confidence: 99%

Metabolic engineering of Ashbya gossypii for deciphering the de novo biosynthesis of γ-lactones

et al. 2019

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Background Lactones are highly valuable cyclic esters of hydroxy fatty acids that find application as pure fragrances or as building blocks of speciality chemicals. While chemical synthesis often leads to undesired racemic mixtures, microbial production allows obtaining optically pure lactones. The production of a specific lactone by biotransformation depends on the supply of the corresponding hydroxy fatty acid, which has economic and industrial value similar to γ-lactones. Hence, the identification and exploration of microorganisms with the rare natural ability for de novo biosynthesis of lactones will contribute to the long-term sustainability of microbial production. In this study, the innate ability of Ashbya gossypii for de novo production of γ-lactones from glucose was evaluated and improved. Results Characterization of the volatile organic compounds produced by nine strains of this industrial filamentous fungus in glucose-based medium revealed the noteworthy presence of seven chemically different γ-lactones. To decipher and understand the de novo biosynthesis of γ-lactones from glucose, we developed metabolic engineering strategies focused on the fatty acid biosynthesis and the β-oxidation pathways. Overexpression of AgDES589 , encoding a desaturase for the conversion of oleic acid (C18:1) into linoleic acid (C18:2), and deletion of AgELO624 , which encodes an elongase that catalyses the formation of C20:0 and C22:0 fatty acids, greatly increased the production of γ-lactones (up to 6.4-fold; (7.6 ± 0.8) × 10 3 µg/g Cell Dry Weight ). Further substitution of AgPOX1 , encoding the exclusive acyl-CoA oxidase in A. gossypii , by a codon-optimized POX2 gene from Yarrowia lipolytica , which encodes a specific long chain acyl-CoA oxidase, fine-tuned the biosynthesis of γ-decalactone to a relative production of more than 99%. Conclusions This study demonstrates the potential of A. gossypii as a model and future platform for de novo biosynthesis of γ-lactones. By means of metabolic engineering, key enzymatic steps involved in their production were elucidated. Moreover, the combinatorial metabolic engineering strategies developed resulted in improved de novo biosynthesis of γ-decalactone. In sum, these proof-of-concept data revealed yet unknown metabolic and genetic determinants important for the future exploration of the de novo production of γ-lactones as an alternative to biotransformation processes. Electronic supplementary material The online version of this article (10.1186/s12934-019-1113-1) contains supplementary material, which is available to authorized users.

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Chirality of the ?-lactones produced bySporidiobolus salmonicolor grown in two different media

Cited by 16 publications

References 27 publications

New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces lipofer Cells

New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces lipofer Cells

Microbial Biosynthesis of Lactones: Gaps and Opportunities towards Sustainable Production

Metabolic engineering of Ashbya gossypii for deciphering the de novo biosynthesis of γ-lactones

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