Establishment of culture conditions for bio-transformation of R-(+)-limonene to limonene-1,2-diol by Colletotrichum nymphaeae CBMAI 0864

Sales, Adones; Moreira, Rafael Chelala; Pastore, Gláucia Maria; Bicas, Juliano Lemos

doi:10.1016/j.procbio.2019.01.022

Cited by 14 publications

(12 citation statements)

References 37 publications

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“…Similarities to Grosmannia claviger strain were observed. In both these strains FAD-binding monooxygenase (Acc No F0 × 7A8) is responsible for the process of epoxy formation, whereas epoxide hydrolyase (Acc No F0 × 7A7) is responsible for opening the epoxide ring to form the diol [ 23 , 31 ]. Scheme 3 , Table 1 .…”

Section: Limonenementioning

confidence: 99%

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

et al. 2020

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The main objective of this article was to present the possibilities of using the enzymatic system of microorganisms and insects to transform small molecules, such as monoterpenes. The most important advantage of this type of reaction is the possibility of obtaining derivatives that are not possible to obtain with standard methods of organic synthesis or are very expensive to obtain. The interest of industrial centers focuses mainly on obtaining particles of high optical purity, which have the desired biological properties. The cost of obtaining such a compound and the elimination of toxic or undesirable chemical waste is important. Enzymatic reactions based on enzymes alone or whole microorganisms enable obtaining products with a specific structure and purity in accordance with the rules of Green Chemistry.

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Section: Limonenementioning

confidence: 99%

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

et al. 2020

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“…It is usually discarded owing to its low aroma value and low chemical stability. While the oxyfunctionalized compounds of limonene have unique aroma and flavors with high economic value and pharmacological action (Sales et al, 2019). α-Terpineol is one of the bio-transformation products from limonene, and it has important applications in daily chemical, pharmaceutical, food, and flavor industries due to its pleasant odor which is similar to lilac (Molina et al, 2019).…”

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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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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“…Limonene-1,2-diol has been associated with a signi cant inhibitory effect on the pro-in ammatory activities of CD4 + and CD8 + T lymphocytes; a potential anticancer activity. It also has insect-attractant properties besides being used as avoring for beverages, chewing gum, gelatins, and puddings (Molina et al 2015b;Sales et al 2018b;Sales 2019c).…”

Section: Fungal Biotransformation Of Limonene For the Production Of Aroma Compoundsmentioning

confidence: 99%

“…From the point of view of the productivity on a larger scale of the compound of interest limonene-1,2-diol, for biotransformation R-(+)-limonene using C. nymphaeae (CBMAI 0864). Moreover, a single addition of 15 g/L -1 substrate R-(+)-limonene at the start of the biotransformation resulted in the highest concentration 4.19 g/L − 1 of limonene-1,2-diol indicating at zero time yielded better results that fed-batch operation was not a good choice (Sales et al 2019c). This bioconversion, mediated by C. nymphaeae (CBMAI 0864), has already been described.…”

Section: Fungal Biotransformation Of Limonene For the Production Of Aroma Compoundsmentioning

confidence: 99%

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

Sevalho

Paulino

Souza

et al. 2021

Preprint

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The number of aroma compounds obtained by biotechnological process has increased tremendously in recent years and, as a result, are now being extensively employed in order to make products more attractive for consumers. In the present review, we inten to assess the wide range of reactions are catalyzed by fungal strains in regards to biotransformation of limonene and pinene for the aroma compounds production, their production rates/maximum concentrations and their biological potential. We comprehensively summarized in this review available data (2000–2021) regarding fungal biotransformation of limonene and pinene as biotechnological processes. Over the past years, has been paid to the biotransformation processes due to mild and environmentally friendly conditions applied. This review has shown that reports on the application of the fungi as a promising source of biocatalysts, mainly for stereoselective reactions such as hydroxylation and epoxidation. Studies have demonstrated the existence of promising monoterpenes used as substrates, which could be important from an industrial standpoint since this increases their importance as starting materials for obtaining aromatic molecules new. Moreover, biological (e.g.,antioxidant, anticancer) activities attributed to some monoterpene biotransformation products are increasingly being reported, indicating that their applications may transcend food, cosmetic and pharmaceutical industry.

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Establishment of culture conditions for bio-transformation of R-(+)-limonene to limonene-1,2-diol by Colletotrichum nymphaeae CBMAI 0864

Cited by 14 publications

References 37 publications

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

Transformations of Monoterpenes with the p-Menthane Skeleton in the Enzymatic System of Bacteria, Fungi and Insects

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

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

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