Monoterpene bioconversion for the production of aroma compounds by fungi isolated from Brazilian fruits

Pinheiro, Denise Maria; Pimentel, Mariana R.; Ssanros, Rosangela dos; Pastore, Gláucia Maria

doi:10.1007/s10068-013-0176-8

Cited by 19 publications

(12 citation statements)

References 30 publications

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“…Regarding the terpenoids, α-terpineol was detected in the grape samples, but was absent in the respective wines. Several studies are present in the literature [ 44 , 45 , 46 ] focused on terpenoid conversions, which require the presence of various microorganisms. The absence of α-terpineol in wine could therefore be linked to a biotransformation of this terpenoid during the wine making process.…”

Section: Resultsmentioning

confidence: 99%

Grape and Wine Composition in Vitis vinifera L. cv. Cannonau Explored by GC-MS and Sensory Analysis

Petretto

Mercenaro

Urgeghe

et al. 2021

Foods

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GC-FID/MS is a powerful technique used to analyze food and beverage aromas. Volatile organic compounds (VOCs) in grape berries play an important role in determining wine quality and are affected by many factors, such as climate and soil that mainly influence their relative concentrations. Wine aroma is generated by a complex mixture of compounds, and the sensory relevance of individual VOCs is far from elucidated. Herein, the VOC content (free and glycosylated) of Cannonau grape skin and juice and of Cannonau wine collected in different areas of Sardinia is explored. Wine sensory analysis was also carried out and the relationship between sensory attributes and VOCs was investigated. Although Cannonau grapes showed the same VOC fingerprint, great variability was identified between samples, although only the differences in 2-phenylethanol and benzyl alcohol concentration in the grape skins and benzyl alcohol and a terpenoid in grape juice were significantly different according to ANOVA. The correlation between VOC content and the sensory profile highlights the role played by 2-methyl-1-butanol and 2-phenylethanol in increasing wine sensory complexity.

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Section: Resultsmentioning

confidence: 99%

Grape and Wine Composition in Vitis vinifera L. cv. Cannonau Explored by GC-MS and Sensory Analysis

Petretto

Mercenaro

Urgeghe

et al. 2021

Foods

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“…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).…”

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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“…Heterotrophic micro-organisms are able to bioconverse monoterpenes and their oxidized analogues. Epoxidation (Javidnia et al 2009;Prieto et al 2011;Molina et al 2013), stereoselective hydroxylation (Rodr ıguez et al 2006;Prieto et al 2011;Iscan et al 2012), oxidation (Rozenbaum et al 2006;Javidnia et al 2009;Prieto et al 2011), isomerization (Ponzoni et al 2008), dehydrogenation (Eaton 1997), stereo-and enantioselective reduction of ketones (Carballeira et al 2004) are common reactions carried out by heterotrophic micro-organisms. Moreover, the capability to lead reactions is the same for both heterotrophic and autotrophic microorganisms.…”

Section: Introductionmentioning

confidence: 99%

Biotransformations of monoterpenes by photoautotrophic micro-organisms

et al. 2014

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Summary Monoterpenes are widely used in food technology, cosmetic and pharmaceutical industries and as compounds of agricultural importance. It is known that compounds comprising this class can be transformed by a variety of organisms, namely by: bacteria, fungi, yeasts, plants or isolated enzymes. Biotransformations, as one of the most important tools of green chemistry, allow obtaining new products using whole cells of micro‐organisms or isolated enzymes in mild reaction conditions. Therefore, biotransformations of monoterpenes, by different type of reaction such as: epoxidation, oxidation and stereoselective hydroxylation, resulted in the production of so desired, enantiomerically defined compounds that can be advised as natural seem to be interesting. Bearing in mind that such processes are carried out also by easy to maintain, photoautotrophic micro‐organisms cultivated at large scale, this paper is focused on biotransformations of acyclic, monocyclic and bicyclic monoterpenes by freshwater or haliphylic cyanobacteria and microalgae on the way of mainly stereoselective hydroxylation. Moreover, aspects of potential industrial application of obtained products in medicine, perfume, cosmetics and food industry are discussed.

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Monoterpene bioconversion for the production of aroma compounds by fungi isolated from Brazilian fruits

Cited by 19 publications

References 30 publications

Grape and Wine Composition in Vitis vinifera L. cv. Cannonau Explored by GC-MS and Sensory Analysis

Grape and Wine Composition in Vitis vinifera L. cv. Cannonau Explored by GC-MS and Sensory Analysis

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

Biotransformations of monoterpenes by photoautotrophic micro-organisms

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