Aroma Profile Analyses of Filamentous Fungi Cultivated on Solid Substrates

Orban, Axel; Fraatz, Marco Alexander; Rühl, Martin

doi:10.1007/10_2019_87

Cited by 7 publications

(4 citation statements)

References 94 publications

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“…However, in their natural habitats, wood-destructing fungi are exposed to many microbial and animal enemies as well as organisms spreading their spores. Thus, it is not surprising that they interact with their highly populated environment through volatile chemical signals . Like the pineapple constituents (1,3 E ,5 Z )-undecatriene and (1,3 E ,5 Z ,8 Z )-undecatetraene, which are known to act as algal pheromones, (5 E / Z ,7 E ,9)-decatrien-2-ones, with their highly similar three-dimensional structure, may serve as signaling compounds in fungi …”

Section: Resultsmentioning

confidence: 99%

“…Thus, it is not surprising that they interact with their highly populated environment through volatile chemical signals. 20 Like the pineapple constituents (1,3E,5Z)-undecatriene and (1,3E,5Z,8Z)-undecatetraene, which are known to act as algal pheromones, (5E/Z,7E,9)-decatrien-2-ones, with their highly similar three-dimensional structure, may serve as signaling compounds in fungi. 21 The biogenesis of the decatrienones is obscure.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…EI-MS (C 10 H 14 O, M = 150 g/mol): m/z (%) = 150 (M + • , 37), 135 (1), 107 (16), 93 (15), 91 (81), 79 (55), 71 (3), 67 (11), 65 (18), and 43 (100). 5), 81 (33), 79 (22), 71 (1), 67 (20), 53 (12), and 43 (100).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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(5E/Z,7E,9)-Decatrien-2-ones, Pineapple-like Flavors from Fomitopsis betulina—Structure Elucidation and Sensorial Properties

Grosse

Pendzialeck

Fohrer

et al. 2019

J. Agric. Food Chem.

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During the cultivation of the edible mushroom Fomitopsis betulina on agro-industrial side streams, a pleasant flavor strongly reminiscent of pineapple was perceived. Aroma extract dilution analyses identified two flavor components with a distinct pineapple odor. On the basis of mass spectrometric data, a Wittig reaction of (E)-penta-2,4-dien-1-yltriphosphonium bromide with ethyl levulinate was conducted. The resulting (5E/Z,7E,9)-decatrien-2-ones were identical to the compounds isolated from the fungal culture. Some structurally related methyl ketones were synthesized, confirmed by nuclear magnetic resonance and mass spectrometry, and their odor was characterized. The lowest odor threshold and most characteristic pineapple-like odor was found for (5Z,7E,9)-decatrien-2-one. Global minimum energy calculation of the methyl ketones and the comparison to (1,3E,5Z)-undecatriene, a character impact compound of fresh pineapple, showed that a chain length of at least 10 carbon atoms and a terminal double bond embedded in a “L”-shaped conformation were common to compounds imparting an intense pineapple-like odor. Both (5E/Z,7E,9)-decatrien-2-ones have not been described as natural flavor compounds.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

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(5E/Z,7E,9)-Decatrien-2-ones, Pineapple-like Flavors from Fomitopsis betulina—Structure Elucidation and Sensorial Properties

Grosse

Pendzialeck

Fohrer

et al. 2019

J. Agric. Food Chem.

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“…This review summarised the information published in the last two decades on mushroom catalysed processes for structural modification of exogenous small molecules to generate or alter aroma and/or flavours. To the best of our knowledge, there is no comprehensive review on mushroom‐mediated generation or alteration of aroma and flavours in recent times (Lomascolo et al ., 1999; Orban et al ., 2019; Zhu et al ., 2022). The current article will update the development in this field and display the credibility of mushroom species for aroma and bioflavour production.…”

Section: Introductionmentioning

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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Effect of fruiting-related genes on the formation of volatile organic compounds in the mushroom Schizophyllum commune

Orban,

Schwab,

Lugones

et al. 2023

Mycol Progress

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In fungi, little is known about connections between volatile organic compound (VOC) formation and developmental stages that are amongst others triggered by fruiting-related genes (FRGs). We analysed the volatilomes of Schizophyllum commune during different developmental stages in a variety of FRG-deletion strains and wild-type strains. The deletion strains Δtea1Δtea1, Δwc-2Δwc-2 and Δhom2Δhom2 were unable to develop fruiting bodies, and Δfst4Δfst4 formed only rudimentary fruiting body structures. Early developmental stages of these strains were dominated by esters, including methyl 2-methylbutanoate, ethyl 2-methylbutanoate, isobutyl 2-methylpropionate, and 2-methylbutyl acetate, of which the last three were not found in the headspace (HS) of the wild-type samples. Compared to the wild type, in the HS of hom2con samples, that are able to form fruiting bodies, methyl 2-methylbutanoate was the most abundant substance at early stages (68–81% of the total peak area). In contrast to fruiting body forming strains, Δtea1Δtea1, Δwc-2Δwc-2, Δhom2Δhom2 and Δfst4Δfst4 showed less sesquiterpenes in the HS. However, the sesquiterpenes found in the HS of FRG-deletion strains, namely, (E)-nerolidol, δ-cadinene, L-calamenene, α-bisabolol and β-bisabolene, were not present in hom2con or wild-type strains that mainly formed fruiting bodies and barely mycelium. Several sesquiterpenes, including α-guaiene, chamigrene and γ-gurjunene, were only found in presence of fruiting bodies. Our results show remarkable connections between FRGs, fruiting body development and VOC production in S. commune, especially counting for sesquiterpenes. Future studies are needed to reveal whether FRGs directly regulates VOC formation or indirectly by changing the phenotype.

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Aroma Profile Analyses of Filamentous Fungi Cultivated on Solid Substrates

Cited by 7 publications

References 94 publications

(5E/Z,7E,9)-Decatrien-2-ones, Pineapple-like Flavors from Fomitopsis betulina—Structure Elucidation and Sensorial Properties

(5E/Z,7E,9)-Decatrien-2-ones, Pineapple-like Flavors from Fomitopsis betulina—Structure Elucidation and Sensorial Properties

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

Effect of fruiting-related genes on the formation of volatile organic compounds in the mushroom Schizophyllum commune

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