Biotechnological Interventions for Production of Flavour and Fragrance Compounds

Recent advances in the Silver catalysed synthesis of furan and its applications

Current Catalysis ◽

10.2174/2211544709999201019162020 ◽

2020 ◽

Vol 09 ◽

Author(s):

C M A Afsina ◽

Mohan Neetha ◽

Thaipparambil Aneeja ◽

Gopinathan Anilkumar

Keyword(s):

Organic Synthesis ◽

Oxidation Potential ◽

Silver Complexes ◽

Wide Spread ◽

Silver Catalysts ◽

Recent Advances ◽

High Oxidation ◽

Furan Moiety ◽

Anti Fungal ◽

Fragrance Compounds

: Furan and its derivatives find wide-spread application as pharmaceuticals, pigments, dyes, brighteners, flavour & fragrance compounds and insecticides. They also exhibit anti-hyperglycemic, analgesic, anti-inflammatory, antibacterial, anti-fungal and anti-tumour activities. Silver catalysts are nowadays commonly used in organic synthesis due to the high oxidation potential and versatile nature of silver complexes. In this review, we summarise the recent advances in the synthesis and applications of furan moiety using silver catalysis and covers literature from 2015-2020.

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

Applied Microbiology and Biotechnology ◽

10.1007/s00253-021-11724-x ◽

2021 ◽

Author(s):

In Jung Kim ◽

Yannik Brack ◽

Thomas Bayer ◽

Uwe T. Bornscheuer

Keyword(s):

Fatty Acids ◽

Functional Characterization ◽

Fatty Aldehyde ◽

Medium Carbon ◽

E Coli ◽

Industrial Utilization ◽

Key Points ◽

Plant Enzymes ◽

Fatty Aldehydes ◽

Fragrance Compounds

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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Supercritical CO2 Extraction of Narcissus poeticus L. Flowers for the Isolation of Volatile Fragrance Compounds

Molecules ◽

10.3390/molecules27020353 ◽

2022 ◽

Vol 27 (2) ◽

pp. 353

Author(s):

Renata Baranauskienė ◽

Petras Rimantas Venskutonis

Keyword(s):

Aromatic Compounds ◽

Supercritical Co2 ◽

Main Part ◽

Dry Weight ◽

Monoterpene Hydrocarbon ◽

Supercritical Co2 Extraction ◽

Benzyl Benzoate ◽

Freeze Dried ◽

Narcissus Poeticus ◽

Fragrance Compounds

The flowers of Narcissus poeticus are used for the isolation of valuable fragrance substances. So far, as the majority of these substances consist of volatile and sensitive to heat compounds, there is a need of developing effective methods for their recovery. In this study, freeze-dried N. poeticus inflorescences were extracted with pure supercritical CO2 (SFE-CO2) and its mixture with 5% co-solvent ethanol (EtOH) at 40 °C. Extract yields varied from 1.63% (12 MPa) to 3.12% (48 MPa, 5% EtOH). In total, 116 volatile compounds were identified by GC-TOF/MS in the extracts, which were divided into 20 different groups. Benzyl benzoate (9.44–10.22%), benzyl linoleate (1.72–2.17%) and benzyl alcohol (0.18–1.00%) were the major volatiles among aromatic compounds. The amount of the recovered benzyl benzoate in N. poeticus SFE-CO2 extracts varied from 58.98 ± 2.61 (24 MPa) to 91.52 ± 1.36 (48 MPa) mg/kg plant dry weight (pdw). α-Terpineol dominated among oxygenated monoterpenes (1.08–3.42%); its yield was from 9.25 ± 0.63 (12 MPa) to 29.88 ± 1.25 (48 MPa/EtOH) mg/kg pdw. Limonene was the major monoterpene hydrocarbon; (3E)-hexenol and heneicosanol dominated among alcohols and phenols; dihydroactinidiolide and 4,8,12,16-tetramethyl heptadecan-4-olide were the most abundant lactones; heptanal, nonanal, (2E,4E)-decadienal and octadecanal were the most abundant aldehydes. The most important prenol lipids were triterpenoid squalene, from 0.86 ± 0.10 (24 MPa) to 7.73 ± 0.18 (48 MPa/EtOH) mg/kg pdw and D-α-tocopherol, from 1.20 ± 0.04 (12 MPa) to 15.39 ± 0.31 (48 MPa/EtOH) mg/kg pdw. Aliphatic hydrocarbons (waxes) constituted the main part (41.47 to 54.93%) in the extracts; while in case of a 5% EtOH the percentage of alkanes was the lowest. The fraction of waxes may be removed for the separation of higher value fragrance materials. In general, the results obtained are promising for a wider application of SFE-CO2 for the recovery of fragrance substances from N. poeticus flowers.

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Effects of fragrance compounds on growth of the silkworm Bombyx mori

PeerJ ◽

10.7717/peerj.11620 ◽

2021 ◽

Vol 9 ◽

pp. e11620

Author(s):

Zhen-peng Kai ◽

Yanwei Qiu ◽

Xue-wei Zhang ◽

Shan-shan Chen

Keyword(s):

Bombyx Mori ◽

Endocrine System ◽

Inhibitory Effect ◽

Ethyl Vanillin ◽

Abnormal Growth ◽

Significant Inhibitory Effect ◽

Ecological Problems ◽

Musk Xylene ◽

Fragrance Compounds

Due to the contamination and biological toxicity of some fragrance compounds, the environmental and ecological problems of such compounds have attracted more and more attention. However, studies of the toxicity of fragrance compounds for insects have been limited. The toxicity of 48 fragrance compounds for the silkworm Bombyx mori were investigated in this study. All of the fragrance compounds examined had no acute toxicity for B. mori larvae, but eight of them (menthol, maltol, musk xylene, musk tibeten, dibutyl sulfide, nerolidol, ethyl vanillin, and α-amylcinnamaldehyde) exhibited chronic and lethal toxicity with LC50 values from 20 to 120 µM. In a long-term feeding study, musk tibeten, nerolidol, and musk xylene showed significant growth regulatory activity. They were also extremely harmful to the cocooning of B. mori, resulting in small, thin, and loose cocoons. Two important insect hormones, namely, juvenile hormone (JH) and 20-hydroxyecdysone (20-E), were quantified in hemolymph following chronic exposure to musk tibeten, nerolidol, and musk xylene, respectively. Musk tibeten significantly increased JH titer and decreased the 20-E titer in hemolymph, and musk xylene had a significant inhibitory effect on JH titer and increased 20-E titer. Although nerolidol had no effect on hormone levels, exogenous JH mimic nerolidol increased the physiological effects of JH and significantly slowed the growth rate of B. mori larvae. The results showed that these fragrance compounds could interfere with the insect endocrine system, leading to death and abnormal growth. The risk to insects of residual fragrance compounds in the environment is worthy of attention.

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The Application of Headspace Solid-phase Microextraction as a Preparation Approach for Gas Chromatography with Mass Spectrometry

Kemija u industriji ◽

10.15255/kui.2020.020 ◽

2020 ◽

Vol 69 (9-10) ◽

pp. 515-520

Author(s):

Igor Jerković ◽

Marina Kranjac ◽

Marina Zekić ◽

Ani Radonić ◽

Zvonimir Marijanović

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Solid Phase Microextraction ◽

Solid Phase ◽

Gas Chromatography Mass Spectrometry ◽

Chemical Markers ◽

Headspace Solid Phase Microextraction ◽

Natural Organic Compounds ◽

The University ◽

Fragrance Compounds

Reviewed in brief are the selected results of the application of headspace solid-phase microextraction as a preparative approach for gas chromatography – mass spectrometry (HS-SPME/GC-MS) for natural organic compounds research at the University of Split, Faculty of Chemistry and Technology. A wide variety of headspace compounds from different natural sources has been identified: lower aliphatic compounds (e.g., C5- and C6-compounds), aromatic compounds, monoterpenes (e.g., linalool derivatives (oxides, anhydro-oxides, epoxides), hotrienol), sesquiterpenes (e.g., eudesmol isomers, hydrocarbons), and C9- and C13-norisoprenoids (e.g., 3,4-dihydro-3-oxoedulan, 4-oxoisophorone, trans-β-damascenone). These compounds are important phytochemicals as flavour/fragrance compounds, chemical markers of the botanical origin or others (e.g., allelochemicals, pheromones, or acaricide residue).

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Fragrance compounds: The wolves in sheep’s clothings

Medical Hypotheses ◽

10.1016/j.mehy.2017.03.025 ◽

2017 ◽

Vol 102 ◽

pp. 106-111 ◽

Cited By ~ 15

Author(s):

Seema Patel

Keyword(s):

Fragrance Compounds

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Heteropoly acid catalysts for the synthesis of fragrance compounds from bio-renewables: acetylation of nopol and terpenic alcohols

RSC Advances ◽

10.1039/c6ra02266a ◽

2016 ◽

Vol 6 (49) ◽

pp. 43217-43222 ◽

Cited By ~ 6

Author(s):

Vinicius V. Costa ◽

Kelly A. da Silva Rocha ◽

Luiz C. A. Oliveira ◽

Elena F. Kozhevnikova ◽

Ivan V. Kozhevnikov ◽

...

Keyword(s):

Heterogeneous Catalyst ◽

Heteropoly Acid ◽

Solvent Free ◽

Acid Catalysts ◽

Green Solvent ◽

Ambient Conditions ◽

Terpenic Alcohols ◽

Commercially Important ◽

Catalytic Processes ◽

Fragrance Compounds

Commercially important esters are obtained from biomass-based alcoholsviagreen solvent-free catalytic processes under ambient conditions using a simple heterogeneous catalyst.

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