Enantioselective synthesis of 6-methyloctanal and 8-methyldecanal, the characteristic aroma components in yuzu Citrus junos, and analysis of their enantiomeric compositions in yuzu essential oil

2021 ◽  
Author(s):  
Yasutaka Ohkubo ◽  
Naomi Tomita ◽  
Yusuke Ogura ◽  
Hirosato Takikawa
Keyword(s):  
Essential Oil ◽  
Enantiomeric Excess ◽  
Enantioselective Synthesis ◽  
Citrus Junos ◽  
Aroma Components

Abstract 6-Methyloctanal and 8-methyldecanal are the characteristic aroma components of yuzu Citrus junos. However, their absolute configurations and enantiomeric compositions in yuzu essential oil have not been analyzed. A concise enantioselective synthesis of both aldehydes was successfully carried out to determine their absolute configurations and enantiomeric compositions. Both aldehydes in yuzu essential oil were found to be (S)-form with high enantiomeric excess.

scholarly journals Overexpression of a Rosa rugosa Thunb. NUDX gene enhances biosynthesis of scent volatiles in petunia

PeerJ ◽  
2021 ◽  
Vol 9 ◽  
pp. e11098
Author(s):  
Lixia Sheng ◽  
Shu Zang ◽  
Jianwen Wang ◽  
Tiantian Wei ◽  
Yong Xu ◽  
...  
Keyword(s):  
Gene Expression ◽  
Essential Oil ◽  
Gene Expression Pattern ◽  
Mass Spectrometry Analysis ◽  
High Yield ◽  
Rosa Rugosa ◽  
Spectrometry Analysis ◽  
Component Content ◽  
China Rose ◽  
Aroma Components

Rosa rugosa is an important natural perfume plant in China. Rose essential oil is known as ‘liquid gold’ and has high economic and health values. Monoterpenes are the main fragrant components of R. rugosa flower and essential oil. In this study, a member of the hydrolase gene family RrNUDX1 was cloned from Chinese traditional R. rugosa ‘Tang Hong’. Combined analysis of RrNUDX1 gene expression and the aroma components in different development stages and different parts of flower organ, we found that the main aroma component content was consistent with the gene expression pattern. The RrNUDX1 overexpressed Petunia hybrida was acquired via Agrobacterium-mediated genetic transformation systems. The blades of the transgenic petunias became wider and its growth vigor became strong with stronger fragrance. Gas chromatography with mass spectrometry analysis showed that the contents of the main aroma components of the transgenic petunias including methyl benzoate significantly increased. These findings indicate that the RrNUDX1 gene plays a role in enhancing the fragrance of petunia flowers, and they could lay an important foundation for the homeotic transformation of RrNUDX1 in R. rugosa for cultivating new R. rugosa varieties of high-yield and -quality essential oil.

scholarly journals GC-MS analysis of the essential oil, aroma components and n-hexane extract of St. John Wort (Hypericum perforatum L., Hypericaceae)

2018 ◽  
Vol 64 (01) ◽  
pp. 63-77
Author(s):  
Arijeta Shabani ◽  
Marija Karapandzova ◽  
Ivana Cvetkovikj Karanfilova ◽  
Gjose Stefkov ◽  
Svetlana Kulevanova
Keyword(s):  
Essential Oil ◽  
Hypericum Perforatum ◽  
Experimental Studies ◽  
Hexane Extract ◽  
Bioactive Constituents ◽  
Specific Chemical ◽  
Ms Analysis ◽  
Hexane Extracts ◽  
Pharmacological Potential ◽  
Aroma Components

St. John Wort (Hypercum perforatum L., Hypericaceae) has been used as a medicinal plant for a long period of time as this plant is characterized by a diversity of bioactive constituents which possess well documented pharmacological activities including antiviral, antimicrobial, anti-inflammatory, antioxidant, hepatoprotective and anti-tumoral activity. Nowadays, special interest is put on its essential oil as some experimental studies showed great biological and pharmacological potential. According this, the main goal of this study was GC/MS analysis of the essential oil, aroma components as well as n-hexane extracts of Hypericum perforatum that grows in Western region in R. Macedonia. GC/FID/MS analyses of the isolated essential oils from leaf, flower and herb resulted in the identification of 84 compounds. The fraction of sesquiterpenes was dominated in all examined oils and the main constituents were germacrene D (17.77-39.03%), E-caryophyllene (11.37-25.71%) and β-selinene (0.69-4.77%). GC/HS/MS analyses of the aroma components resulted in the identification of 23 compounds. Among them, isononane was identified as main aroma component (up to 75%). GC/FID/MS analyses of the n-hexane extracts resulted in the identification of 60 compounds which were characterized by the presence of terpenoid (mono- and sesquiterpene) components and non-terpenoid constituents mainly consisted of hydrocarbons and their oxygenate derivatives and related components. The non-terpenoid fraction represented the largest part of the analysed extracts. The most abundant were nonacosane (15.45-49.28%), octacosane (1.33-40.05%) and pentacosane (1.68-9.04%). The aerial parts of H. perforatum collected from Western part of R. Macedonia could be considered as a good source of essential oil with specific chemical profile as well as aroma components and high lipophilic compounds, but further investigation should be done in accordance to their possible commercial or medicinal use. Keywords: Hypericum perforatum, essential oil, aroma components, n-hexane extract, GC-MS

scholarly journals Composition of Essential Oils from Seeds of Abies koreana

2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800
Author(s):  
Anna Wajs-Bonikowska ◽  
Karol Olejnik ◽  
RadosJaw Bonikowski ◽  
Piotr Banaszczak
Keyword(s):  
Essential Oil ◽  
Essential Oils ◽  
Enantiomeric Excess ◽  
Rich Source ◽  
Oxygenated Monoterpenes ◽  
Abies Koreana ◽  
Korean Fir ◽  
Nmr Methods

The essential oils from seeds of nine Abies koreana specimens have been studied using GC-MS-FID and NMR methods, leading to the determination of 96 volatiles, which constituted over 99% of the oils. The hydrodistilled oils of fresh, resinous scent were isolated with yields in the range of 3.8-8.5%. The results showed that the essential oil of Korean fir seeds contained 70-95% monoterpenes and 1-20% oxygenated monoterpenes as the dominant groups. The numerous sesquiterpenes, diterpenes and their oxygenated derivatives constituted only 2-8% of the oil. The major component of the seed essential oil was limonene (4172 g/100g); the laevorotary form of this terpene predominated. A. koreana seeds seem to be a rich source of both essential oil and (-)-limonene, whose average enantiomeric excess was above 95%.

scholarly journals Natural Variability in Enantiomeric Composition of Bioactive Chiral Terpenoids in the Essential Oil of Solidago Canadensis L. from Uttarakhand, India

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Chandan S. Chanotiya ◽  
Anju Yadav
Keyword(s):  
Essential Oil ◽  
Narrow Range ◽  
Enantiomeric Excess ◽  
Natural Variability ◽  
Biologically Active ◽  
Enantiomeric Composition ◽  
Bornyl Acetate ◽  
Solidago Canadensis ◽  
Capillary Gc ◽  
Germacrene D

The natural variability in the enantiomeric distribution of biologically active chiral terpenoids in Solidago canadensis L. essential oil from Kumaon was evaluated by enantioselective capillary GC, capillary GC, and GC-MS. Germacrene D, a sesquiterpene hydrocarbon, was noticed as the major compound, contributing 56.7%, 75.5% and 69.7% to the samples, while other constituents with variable compositions were limonene (0.2 to 12.5%), bornyl acetate (2.1 to 2.9%), δ-elemene (2.4 to 3.2), β-elemene (1.3 to 1.8%), and elemol (1.4 to 2.6%). The enantiomeric excess has been determined for germacrene D with (+)-enantiomer (>41.8% to >47%) dominating over the (-)-enantiomer in all the samples. Furthermore, there has been above 95% enantiomeric excess for ( R)-(+)-limonene (>95.1% to >99%), whereas moderate to low excess for (1 R)-(+)-α-pinene (>47.9%), and (1 S)-(-)-β-pinene (>30.3%) was established. Notably, only (-)-bornyl acetate was found as a single enantiomer with >99% enantiomeric excess. However, for all the identified chiral terpenoids, the enantiomeric distribution varied within only a narrow range in all the samples.

Chemoenzymatic dynamic kinetic resolution as a key step in the enantioselective synthesis of (S)-salbutamol

2011 ◽  
Vol 76 (7) ◽  
pp. 919-927 ◽  
Author(s):  
Annika Träff ◽  
Carmen E. Solarte ◽  
Jan-E. Bäckvall
Keyword(s):  
Burkholderia Cepacia ◽  
Kinetic Resolution ◽  
Enantiomeric Excess ◽  
Enantioselective Synthesis ◽  
Dynamic Kinetic Resolution

The synthesis of (S)-salbutamol is described. By utilizing DKR in the enantiodetermining step, employing Burkholderia cepacia lipase (PS-IM), (S)-acetate ((S)-6) was obtained in excellent enantiomeric excess (98%). The subsequent transformations yielded the salt of (S)-salbutamol with retained stereochemistry.

Application of integrative physiological approach to evaluate human physiological responses to the inhalation of essential oils of Japanese citrus fruits iyokan (Citrus iyo) and yuzu (Citrus junos)

2021 ◽  
Author(s):  
Motoko Ohata ◽  
Lanxi Zhou ◽  
Shiori Ando ◽  
Shu Kaneko ◽  
Kazumi Osada ◽  
...  
Keyword(s):  
Prefrontal Cortex ◽  
Essential Oil ◽  
Essential Oils ◽  
Sympathetic Nerve Activity ◽  
Nervous Activity ◽  
Citrus Fruits ◽  
Nerve Activity ◽  
Citrus Junos ◽  
Central Nervous Systems ◽  
Physiological Approach

Abstract This study investigated the effects of essential oil odors from Japanese citrus fruits, iyokan (Citrus iyo) and yuzu (Citrus junos), on human psychology and both the autonomic and central nervous systems. The inhalation of both essential oils significantly increased miosis rate and fingertip temperature and could induce parasympathetic dominance by suppressing sympathetic nerve activity. Oxyhemoglobin concentration in the prefrontal cortex increased after the inhalation of yuzu essential oil and decreased after the inhalation of iyokan essential oil. Subjectively, the inhalation of both essential oils reduced the feelings of fatigue and improved the feelings of refreshment, suggesting that the effect of autonomic nervous activity might involve in these psychological changes directly. Moreover, we observed that task performance improved after inhaling yuzu essential oil, which may be due to the increase in oxyhemoglobin concentration in the prefrontal cortex.

scholarly journals Characterization of Volatile Components of Zingiber roseum Essential Oil Using Capillary GC on Modified Cyclodextrins

2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
VPPalayam S Pragadheesh ◽  
Anju Yadav ◽  
Manju Singh ◽  
Chandan S Chanotiya
Keyword(s):  
Essential Oil ◽  
Essential Oils ◽  
Enantiomeric Excess ◽  
Volatile Components ◽  
Capillary Gc ◽  
Modified Cyclodextrins ◽  
Cyclodextrin Cavity ◽  
Possible Cause ◽  
Chiral Gas Chromatography

The essential oil from different parts of Zingiber roseum plants was extracted by hydrodistillation, and analyzed using enantio-GC, capillary-GC and GC-MS. Two chiral selectors, 6- tert-butyldimethylsilyl-2,3-diethyl-β-cyclodextrin (TBDE-β-CD), and 2,3,6-methyl-β-cyclodextrin (PM-β-CD) doped into 14% cyanopropylphenyl/ 86% dimethylpolysiloxane, and 35% diphenyl/ 65% dimethylpolysiloxane, respectively were compared in order to clarify the stereochemistry and enantioselectivity of terpenoids using chiral gas chromatography. The enantiomeric excess for (1R)-(+)-α-pinene, (1R)-(+)-β-pinene, and (R)-(+)-limonene were characteristic for the rhizome. In TBDE-β-cyclodextrin coated chiral columns, a significant increase in separation factor (a) for β-pinene, limonene, linalool and α-terpineol enantiomers was observed when compared with methyl substituted β-cyclodextrin. The increase in chain length of the alkyl substituents may be the possible cause for enantiomer separation in β-cyclodextrin cavity. In addition, enantioreversal of α-pinene enantiomers in 6-tert-butyldimethylsilyl-2,3-diethyl-β-cyclodextrin was noticed as a unique feature. The enantiomeric compositions of Z. roseum fruit and flower essential oils were similar, but, in contrast, the rhizome oil contained an entirely different composition. Therefore, these results aid in the authentication of the natural origin of Z. roseum essential oils.

scholarly journals Biotransformation with a New Acinetobacter sp. Isolate for Highly Enantioselective Synthesis of a Chiral Intermediate of Miconazole

Catalysts ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 462 ◽  
Author(s):  
Yanfei Miao ◽  
Yuewang Liu ◽  
Yushu He ◽  
Pu Wang
Keyword(s):  
Asymmetric Reduction ◽  
Enantiomeric Excess ◽  
Enantioselective Synthesis ◽  
Morphological Observation ◽  
Resting Cells ◽  
16S Rdna Sequence Analysis ◽  
Versatile Tool ◽  
Drug Synthesis ◽  
Biochemical Identification ◽  
Acinetobacter Sp

(R)-2-Chloro-1-(2,4-dichlorophenyl) ethanol is a chiral intermediate of the antifungal agent Miconazole. A bacterial strain, ZJPH1806, capable of the biocatalysis of 2-chloro-1-(2,4-dichlorophenyl) ethanone, to (R)-2-chloro-1-(2,4-dichlorophenyl) ethanol with highly stereoselectivity was isolated from a soil sample. It was identified as the Acinetobacter sp., according to its morphological observation, physiological-biochemical identification, and 16S rDNA sequence analysis. After optimizing the key reaction conditions, it was demonstrated that the bioreduction of 2-chloro-1-(2,4-dichlorophenyl) ethanone was effectively transformed at relatively high conversion temperatures, along with glycerol as cosubstrate in coenzyme regeneration. The asymmetric reduction of the substrate had reached 83.2% yield with an enantiomeric excess (ee) of greater than 99.9% at 2 g/L of 2-chloro-1-(2,4-dichlorophenyl) ethanone; the reaction was conducted at 40 °C for 26 h using resting cells of the Acinetobacter sp. ZJPH1806 as the biocatalyst. The yield had increased by nearly 2.9-fold (from 28.6% to 83.2%). In the present study, a simple and novel whole-cell-mediated biocatalytic route was applied for the highly enantioselective synthesis of (R)-2-chloro-1-(2,4-dichlorophenyl) ethanol, which allowed the production of a valuable chiral intermediate method to be transformed into a versatile tool for drug synthesis.

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