Optimisation of <i>α</i>‐terpineol production by limonene biotransformation using <i>Penicillium digitatum</i><scp>DSM</scp> 62840

Tai, Ya-Nan; Xu, Min; Ren, Jianmin; Dong, Man; Yang, Ziyu; Pan, Siyi; Fan, Gang

doi:10.1002/jsfa.7171

Cited by 28 publications

(21 citation statements)

References 34 publications

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“…The researches on the biotransformation of limonene have been reported for decades, including the isolation of microorganisms (Rottava et al, 2010a,b;Badee et al, 2011;Bier et al, 2017), the optimization of bio-transformation process (Bicas et al, 2008;Bicas et al, 2010;Molina et al, 2019) and the factors affecting the biotransformation (Prieto et al, 2011;Tai et al, 2016). Nevertheless, industrial applications of the limonene bioconversion are still limited because of the substrate inhibition in the liquid medium and the difficulty of the product isolation.…”

Section: Introductionmentioning

confidence: 99%

“…Penicillium digitatum is a major fungal pathogen of citrus fruits, and it is reported that this fungal had the potential application in detoxifying monoterpenes (Molina et al, 2013). In our previous study, it is observed that P. digitatum strain DSM 62840 could convert limonene into α-terpineol with high regioselectivity (Tai et al, 2016). And the differentially expressed proteins at different periods of limonene biotransformation were explored using the isobaric tag for relative and absolute quantitation (iTRAQ) (Zhang et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

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Genomic and Transcriptomic Study for Screening Genes Involved in the Limonene Biotransformation of Penicillium digitatum DSM 62840

et al. 2020

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α-Terpineol has been widely used in daily chemical, pharmaceutical, food, and flavor industries due to its pleasant odor with high economic value and pharmacological action. Our previous study showed that Penicillium digitatum DSM 62840 was an efficient biocatalyst for the transformation of limonene to α-terpineol. Thus, it was meaningful to explore the genome features and the gene expression differences of strain DSM 62840 during limonene biotransformation, and the detailed bioconversion pathways. In this study, the functional genes related to limonene bioconversion were investigated using genome and transcriptome sequences analysis. The results showed that the P. digitatum DSM 62840 genome was estimated to be 29.09 Mb and it encoded 9,086 protein-encoding genes. The most annotated genes were associated to some protein metabolism and energy metabolism functions. When the threshold for differentially expressed genes (DEGs) was set at twofold ratio, a total of 4,128, and 4,148 DEGs were identified in P_L_12h (limonene-treated condition) compared with P_0h (blank) and P_12h (limonene-untreated blank), respectively. Among them, the expression levels of genes involved in the biosynthesis of secondary metabolites, energy metabolism and ATP-binding cassette (ABC) transporters were significantly altered during the biotransformation. And the reliability of these results was further confirmed by quantitative real-time polymerase chain reaction (RT-qPCR). Moreover, we found that the enzyme participated in limonene biotransformation was inducible. This enzyme was located in the microsome, and it was inhibited by cytochrome P450 inhibitors. This indicated that the cytochrome P450 may be responsible for the limonene bioconversion. Several differentially expressed cytochrome P450 genes were further identified, such as PDIDSM_85260 and PDIDSM_67430, which were significantly upregulated with limonene treatment. These genes may be responsible for converting limonene to α-terpineol. Totally, the genomic and transcriptomic data could provide valuable information in the discovery of related-genes which was involved in limonene biotransformation, pathogenicity of fungi, and investigation of metabolites and biological pathways of strain DSM 62840.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Genomic and Transcriptomic Study for Screening Genes Involved in the Limonene Biotransformation of Penicillium digitatum DSM 62840

et al. 2020

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“…Cosolvent can be used for three different biotransformation of single‐phase, biphasic, and reversed micelle systems (Tai et al., 2016). Substrates without any cosolvent were converted into control and the conversion rate was set at 100%.…”

Section: Resultsmentioning

confidence: 99%

Catalytic condition optimization in the conversion of nootkatone from valencene byYarrowia lipolytica

Xiao

Ren

Fan

et al. 2021

J. Food Process. Preserv.

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Yarrowia lipolytica was a widespread and promising object in biotechnology, which was used to increase the biotransformation of valencene into nootkatone in shake flasks in this study. The main objective of this work is to determine the optimum combination of transformation conditions in shake flasks on the basis of single factor process optimization experiment. The results showed that Y. lipolytica was cultured in medium for 36 hr (exponential phase) and the amount of added Y. lipolytica was 5% (v/v). The concentration of substrate valencene was 920 mg·L−1, and the transformation time was 36 hr after adding substrates. Dimethyl sulfoxide, a water‐soluble organic solvent, was used as a co‐solvent with a concentration of 0.8% (v/v). The maximum production of nootkatone was 628.41 ± 18.60 mg·L−1 and the conversion rate was 68.30 ± 2.02% at cultivation conditions of 32°C, 150 rpm, and PH 5.30. The results showed that optimizing the catalytic conditions can significantly increase the yield of nootkatone by Y. lipolytica. Practical applications Recently, natural nootkatone is increasingly important due to its flavoring and physiological effects, but the amount of nootkatone in plants is low and cannot meet the demand. Also, there were few studies about microbial transformation of valencene by Yarrowia lipolytica under certain catalytic conditions. We demonstrated that optimizing the catalytic conditions can significantly increase the yield of nootkatone. Therefore, it provides a basis for the subsequent use of genetic engineering to transform Y. lipolytica to produce nootkatone.

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“…Fungal bioconversion of R‐(+)‐limonene was analysed in 100 ml Erlenmeyers flasks containing 40 ml of liquid media modified from Tai et al . (2016), with malt extract (10 g l −1 ), yeast extract (0·5 g l −1 ), bacteriological peptone (0·5 g l −1 ), glucose (10 g l −1 ), Tween 80 (0·1 g l −1 ), R‐(+)‐limonene (20 g l −1 ) and KH 2 PO 4 buffer pH 6·2. Inoculum consisted of 1 ml of spore suspension at concentration of 2 × 10 7 spores per ml re‐suspended in 0·1% Tween 80 solution, obtained from a pre‐inoculum medium of 5‐ to 7‐day‐old fungal colony.…”

Section: Methodsmentioning

confidence: 99%

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

Velázquez

Sadañoski

Zapata

et al. 2020

J. Appl. Microbiol.

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Aims: The aims of this article were to select fungal species with high tolerance and high growth rate in mediums supplemented with limonene and citrus essential oils (CEOs), and to test the bioconversion capability of the chosen isolates for the bioproduction of aroma compounds. Methods and Results: Based on the use of predictive mycology, 21 of 29 isolates were selected after assaying R-(+)-limonene and CEO tolerance (10 g l −1). With a dendrogram divisive coefficient of 0Á937, the subcluster two with isolates Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 gathered the highest tolerance and mycelia growth speed. Ultrastructural analysis indicated that culture media containing limonene had no visible toxic activity that could promote morphological changes in the fungal cell wall. The biomass of A. niger LBM055 was distinctive in liquid media supplemented with R-(+)-limonene (0Á57 AE 0Á07 g) and it was selected to prove bioconversion capacity, under static and agitated conditions, and converted up to 98% of limonene, yielding a wide variety of products that were quantified by GC-FID. It was obtained at molecular weights less than limonene (64-100%), between limonene and αterpineol (12-72%) and greater than α-terpineol (2-48%). Conclusions: Aspergillus niger LBM 055, Penicillium sp. LBM 150, Penicillium sp. LBM 151 and Penicillium sp. LBM 154 showed to the highest tolerance and growth rate in mediums supplemented with R-(+)-limonene and orange and lemon essential oils. Particularly, A. niger LBM055, showed limonene bioconversion capability and produced different molecular weights compounds such us α-terpineol. Significance and Impact of the Study: Different bioproducts can be obtained by changing operative condition with the same fungus, and this bioprocess aspect is a significant approach to be adopted on industrial scale leading to the creation of new natural flavours and fragrance compositions.

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Optimisation of α‐terpineol production by limonene biotransformation using Penicillium digitatumDSM 62840

Cited by 28 publications

References 34 publications

Genomic and Transcriptomic Study for Screening Genes Involved in the Limonene Biotransformation of Penicillium digitatum DSM 62840

Genomic and Transcriptomic Study for Screening Genes Involved in the Limonene Biotransformation of Penicillium digitatum DSM 62840

Catalytic condition optimization in the conversion of nootkatone from valencene byYarrowia lipolytica

Bioproduction of α‐terpineol and R‐(+)‐limonene derivatives by terpene‐tolerant ascomycete fungus as a potential contribution to the citrus value chain

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