Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi

Zhuk, Tatyana S.; Skorobohatko, Oleksandra S.; Albuquerque, Wendell; Zorn, Holger

doi:10.1016/j.bioorg.2021.104651

Cited by 7 publications

(4 citation statements)

References 44 publications

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“…The carbonyl reducing ability of Basidiomycota has been demonstrated in several occasions. The Polyporales such as Dichomitus albidofuscus, Phanerochaete chrysosporium, Bjerkandera sp., Pycnoporus cinnabarinus, Polyporus tuberaster, and Ischnoderma benzoinum have shown their reducing activity on aromatic and/or aliphatic acids, aldehydes, and ketones, thus strengthening our hypothesis. − Therefore, the aim of the present study was (i) to identify an efficient process for the aroma alteration of aldehyde-rich essential oils mediated by the mushroom species in the submerged culture, (ii) chemical and aroma profiling of the new bioflavor, and (iii) optimization of the fermentation parameters in the shake flask and downstream processing.…”

Section: Introductionmentioning

confidence: 55%

Mushroom-Mediated Reductive Bioconversion of Aldehyde-Rich Essential Oils for Aroma Alteration: A Rose-like Floral Bioflavor from Citronella Oil

Bora

Borah

Kalita

et al. 2023

J. Agric. Food Chem.

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The bioflavors are of high demand in food and beverage industries. The current study identified reductive processes mediated by mushroom species to alter the aroma of aldehyde-rich essential oils in the submerged culture. Neofomitella polyzonata, a polypore mushroom, reduced citronellal and citral in the citronella oil into corresponding alcohols that altered the oil aroma, creating a new bioflavor. The screening with 43 aldehydes showed its broad substrate scope within aromatic and linear aldehydes, yet influenced by the electronic and steric factors. Under an optimized condition, it efficiently converted up to 1.5 g/L citrusy and sharp citronella oil into a terpene alcohol-rich (citronellol and geraniol) floral, sweet, fresh, and rosy oily product within 12 h. The preparative-scale fermentation in the shake flask followed by distillation, an organic solvent-free downstream process, furnished the product in 87.2% w/w yield. Detailed sensory analyses and volatile chemo-profiling established the uniqueness in the product aroma and identified citronellol and geraniol as the key odorants. The chemometric analysis found best compositional similarity of this product with Damask or Turkish rose oils. The preference test for the water flavored with the fermented product (0.001−0.005% v/ v) indicated its potential as a rosy bioflavor for the beverages.

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Section: Introductionmentioning

confidence: 55%

Mushroom-Mediated Reductive Bioconversion of Aldehyde-Rich Essential Oils for Aroma Alteration: A Rose-like Floral Bioflavor from Citronella Oil

Bora

Borah

Kalita

et al. 2023

J. Agric. Food Chem.

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“…The instances of reduction through basidiomycetes are less compared to oxidative transformations. Nevertheless, reductive capability of mushrooms has been established well on linear and/or aromatic carbonyls (e.g., aldehydes, ketones and carboxylic acids) in several occasions (Ishihara et al, 2012;Zhuk et al, 2021;Bora et al, 2023). In a report, edible mushroom species were used for the stereoselective reduction of linear a-keto esters to a-hydroxy esters in the submerged condition (Ishihara et al, 2012).…”

Section: Reductive Transformation Of Aromatic and Linear Carbonylsmentioning

confidence: 99%

“…Polypore mushrooms have recently been reported to carry out efficient carbonyl reduction in their submerged cultures. For example, Dichomitus albidofuscus reduced a variety of linear and aromatic aldehydes, cyclic ketone, aromatic or phenyl‐substituted linear acids (lignin monomers) to their corresponding alcohols (Zhuk et al ., 2021). The substrates like 2‐heptenal, dodecanal, undecanal, benzoic acid, vanillic acid were reduced to flavour molecules 1‐heptanol, 1‐dodecanol, 1‐undecanol, benzyl alcohol, benzaldehyde, vanillin, respectively.…”

Section: Aroma and Flavour Generation Through Mushroom‐based Biocatal...mentioning

confidence: 99%

Mushroom‐based biocatalysts for the synthesis of aroma and flavours from exogenous organic molecules: a review of two decades

Bora,

Kemprai,

Hussain

et al. 2023

Int J of Food Sci Tech

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SummaryMushroom species, rich in lignolytic oxidoreductases are promising biocatalysts for the functionalization or degradation of small molecules to produce aroma and/or flavours. These macrofungi, sources of thermostable extracellular enzymes are often safer as biocatalysts, produce aromatic flavours similar to plant‐origin and capable of using a wide range of recalcitrant lignocellulosic substrates. The current review summarises the research on mushroom‐mediated production of aroma and aromatic flavours from organic molecules (pure or extract) in the last two decades. It mainly includes oxidative conversion or degradation of small molecules such as mono and sesquiterpenoids, phenylpropanoids, aromatic or linear alcohols and carbonyls, alkenes, carotenoids, fatty acids and amino acids into oxygenated aroma/flavours using the whole‐cells or purified enzymes of mushroom‐origin. Allylic or alcohol oxidation, alkene cleavage and degradation of unsaturated long‐chains were the major pathways of oxidative transformations. Reductive conversions of aromatic and linear carbonyls were also exemplified. However, slow biomass growth, low‐substrate load, conversion, product titre and selectivity, long fermentation time, difficult/low expression of enzymes, cost‐effective and efficient upscaling, insufficient genomic data are major challenges in utilising the diversity of mushroom species for aroma and bioflavour production in industrial scale.

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“…The reduction of carbonyl groups has already been shown by us for a number of white-rot fungi including DAL. [20] However, the addition of 2 to the mature cultures on the 6 th day resulted in 4 as main product (entries 3 and 4). During three days no biotransformation was observed if 3 was added on the 2 nd culture day (entry 5).…”

mentioning

confidence: 99%

Aerobic C−C Bond Cleavage Catalyzed by Whole‐Cell Cultures of the White‐Rot Fungus Dichomitus albidofuscus

2021

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Whole-cell cultures of the basidiomycetous white-rot fungus Dichomitus albidofuscus exhibit varying catalytic activity towards aromatic compounds depending on the growth stage. This study reveals the catalytic behavior of mature whole-cell cultures that effectively catalyze a CÀ C bond cleavage oxidizing toluene, benzaldehyde and acetophenone to phenol. The reaction products were analyzed by GC-MS and NMR techniques. To exclude the de novo formation of phenol by the fungus, its origin has been proven by bioconversion of benzaldehyde-d 5 . The key step involves an aerobic Baeyer-Villiger type rearrangement where the incorporation of oxygen into the product was confirmed based on isotope labelling experiments with 18 O 2 . Intermediate esters were not found in reaction mixture presumably due to the detected esterase activity in the mycelium as well as in supernatant of the wholecell cultures. As a result, the sequence of biocatalytic reactions catalyzed by D. albidofuscus for the degradation of toluene via CÀ C bond cleavage has been disclosed.

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Scope and limitations of biocatalytic carbonyl reduction with white-rot fungi

Cited by 7 publications

References 44 publications

Mushroom-Mediated Reductive Bioconversion of Aldehyde-Rich Essential Oils for Aroma Alteration: A Rose-like Floral Bioflavor from Citronella Oil

Mushroom-Mediated Reductive Bioconversion of Aldehyde-Rich Essential Oils for Aroma Alteration: A Rose-like Floral Bioflavor from Citronella Oil

Mushroom‐based biocatalysts for the synthesis of aroma and flavours from exogenous organic molecules: a review of two decades

Aerobic C−C Bond Cleavage Catalyzed by Whole‐Cell Cultures of the White‐Rot Fungus Dichomitus albidofuscus

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