Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes

Hammer, Andreas Klaus; Emrich, Nils O; Ott, Janina; Birk, Florian; Fraatz, Marco Alexander; Ley, Jakob P; Geißler, Torsten; Bornscheuer, Uwe T.; Zorn, Holger

doi:10.1021/acs.jafc.0c06872

Cited by 9 publications

(11 citation statements)

References 49 publications

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“…Extraction from natural sources, such as plants and fungi, has been traditionally achieved to obtain fatty aldehydes, and the in-depth analysis of these extracts has served as a useful basis for the identification of valuable compounds (Hammer et al 2021 ). Currently, most of commercial flavors and fragrances are chemically synthesized using either fossil-based starting materials or renewable lipid sources (Gaylord 1957 ).…”

Section: Introductionmentioning

confidence: 99%

Two novel cyanobacterial α-dioxygenases for the biosynthesis of fatty aldehydes

Kim

Brack

Bayer

et al. 2021

Appl Microbiol Biotechnol

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Abstractα-Dioxygenases (α-DOXs) are known as plant enzymes involved in the α-oxidation of fatty acids through which fatty aldehydes, with a high commercial value as flavor and fragrance compounds, are synthesized as products. Currently, little is known about α-DOXs from non-plant organisms. The phylogenic analysis reported here identified a substantial number of α-DOX enzymes across various taxa. Here, we report the functional characterization and Escherichia coli whole-cell application of two novel α-DOXs identified from cyanobacteria: CalDOX from Calothrix parietina and LepDOX from Leptolyngbya sp. The catalytic behavior of the recombinantly expressed CalDOX and LepDOX revealed that they are heme-dependent like plant α-DOXs but exhibit activities toward medium carbon fatty acids ranging from C10 to C14 unlike plant α-DOXs. The in-depth molecular investigation of cyanobacterial α-DOXs and their application in an E. coli whole system employed in this study is useful not only for the understanding of the molecular function of α-DOXs, but also for their industrial utilization in fatty aldehyde biosynthesis.Key points• Two novel α-dioxygenases from Cyanobacteria are reported• Both enzymes prefer medium-chain fatty acids• Both enzymes are useful for fatty aldehyde biosynthesis Graphical abstract

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Section: Introductionmentioning

confidence: 99%

Two novel cyanobacterial α-dioxygenases for the biosynthesis of fatty aldehydes

Kim

Brack

Bayer

et al. 2021

Appl Microbiol Biotechnol

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“…The volatile does not occur in pineapple fruit but shows high structural similarity to 1-(3E,5Z)-undecatriene, a genuine character impact hydrocarbon of this fruit. Likewise unusual were dodec-11-enoic acid and di-and tri-unsaturated C16 isomer fatty acids in the lipids of Flammulina velutipes [112]. An excellent proof of the enormous synthetic potential of basidiomycetes was the identification of the (5E/Z,7E,9)-decatrien-2-ones in submerged, cultured Fomitopsis betulina (Figure 5b) [110,111].…”

Section: Formation Of Volatile Flavoursmentioning

confidence: 95%

“…The volatile does not occur in pineapple fruit but shows high structural similarity to 1-(3E,5Z)-undecatriene, a genuine character impact hydrocarbon of this fruit. Likewise unusual were dodec-11-enoic acid and di-and tri-unsaturated C16 isomer fatty acids in the lipids of Flammulina velutipes [112]. Their observation was used to generate ω1-unsaturated aldehydes through α-oxidation, with dodec-11-enal possessing a pleasant coriander/leaf-like smell (Figure 5c).…”

Section: Formation Of Volatile Flavoursmentioning

confidence: 98%

Improved Foods Using Enzymes from Basidiomycetes

Berger

Ersoy

2022

Processes

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Within the kingdom of fungi, the division Basidiomycota represents more than 30,000 species, some with huge genomes indicating great metabolic potential. The fruiting bodies of many basidiomycetes are appreciated as food (“mushrooms”). Solid-state and submerged cultivation processes have been established for many species. Specifically, xylophilic fungi secrete numerous enzymes but also form smaller metabolites along unique pathways; both groups of compounds may be of interest to the food processing industry. To stimulate further research and not aim at comprehensiveness in the broad field, this review describes some recent progress in fermentation processes and the knowledge of fungal genetics. Processes with potential for food applications based on lipases, esterases, glycosidases, peptidases and oxidoreductases are presented. The formation and degradation of colourants, the degradation of harmful food components, the formation of food ingredients and particularly of volatile and non-volatile flavours serve as examples. In summary, edible basidiomycetes are foods—and catalysts—for food applications and rich donors of genes to construct heterologous cell factories for fermentation processes. Options arise to support the worldwide trend toward greener, more eco-friendly and sustainable processes.

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“…The standard needs to be pure, chromatographically separated from the target compound, and must have a known OT in the air. In recent studies (2E)-decenal became the most commonly used IS [21][22][23][24]. Odor perception depends on the volatility of the compounds and the molecule geometry, which determines the interaction of the odotopes with the corresponding olfactory receptor proteins.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Odor Characteristics of Novel Non-Canonical Terpenes

et al. 2022

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Several non-canonical, methylated terpenes have been described as products of genetically modified Escherichia coli recently, and the aroma properties of 28 odor-active methylated derivatives of prenol, isoprenol, bornane, camphene, carene, citronellol, fenchol, geraniol, limonene, linalool, terpineol, and farnesol were characterized for the first time in the current study. Twelve methylated monoterpenes exhibited a particularly intense and pleasant odor and were therefore chosen for the determination of their respective odor thresholds (OTs) in comparison to their non-methylated equivalents. In addition to the determination of OTs based on the literature value for the internal standard, (2E)-decenal, the threshold values of the compounds with individually determined OTs of the participants were calculated. This enabled a more precise identification of the OTs. Among the non-canonical terpenes, the lowest OTs in the air were found for 2-methyllinalool (flowery, 1.8 ng L−1), 2-methyl-α-fenchol (moldy, 3.6 ng L−1), 2-methylgeraniol (flowery, 5.4 ng L−1), 2-methylcitronellol (citrus-like, 7.2 ng L−1), and 4-methylgeraniol (citrus-like, 16 ng L−1). The derivatives of geraniol, linalool, and citronellol showed very pleasant odor impressions, which could make them interesting for use as flavoring agents in the flavor and fragrance industry.

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Biotechnological Production and Sensory Evaluation of ω1-Unsaturated Aldehydes

Cited by 9 publications

References 49 publications

Two novel cyanobacterial α-dioxygenases for the biosynthesis of fatty aldehydes

Two novel cyanobacterial α-dioxygenases for the biosynthesis of fatty aldehydes

Improved Foods Using Enzymes from Basidiomycetes

Odor Characteristics of Novel Non-Canonical Terpenes

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