New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils

König, Wilfried Α.; Gehrcke, Bärbel; Icheln, Detlef; Evers, Petra; Dönnecke, Jürgen; Wang, Weichao

doi:10.1002/jhrc.1240150603

Cited by 137 publications

(35 citation statements)

References 14 publications

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“…The dual system can be varied, using one achiral and one chiral stationary phases; two achiral stationary phases or two chiral stationary phases. 25,26 According to results, the essential oils obtained from propolis of three regions of southern of Brazil have an expressive concentration of monoterpenes, with a variable enantiomeric composition. Establishing a relation between the monoterpenes and chiral distribution, it is possible to attribute that a-pinene and limonene suffered variations in enantiomeric form in excess, while in the case of b-pinene, the preference is observed by the (-) enantiomeric form in excess ( Table 2).…”

Section: Resultsmentioning

confidence: 99%

Chiral Analysis of Monoterpenes in Volatile Oils From Propolis

Simionatto

Facco

Morel

et al. 2012

J. Chil. Chem. Soc.

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The essential oils obtained by hydrodistillation from samples of propolis manufactured in three regions of Rio Grande do Sul State at Brazil, were analyzed through CG, CG-MS and chiral phase gas chromatography (CPGC). These analyses display the presence of samples with elevated essential oil purport, when compared with plants. The yields obtained were until 3.8%. The samples exhibited similar composition, with predominance of the monoterpenes a-pinene (57-63%), b-pinene (12.5-30.8%) and limonene (1.5-11.2%). In chiral analysis of these constituents were observed modifications in the enantiomeric excess of isomers of a-pinene and limonene in relation with source location of the sample, already in the chiral analysis of b-pinene were detected only elevated excess of the enantiomer with the (-) configuration. The antimicrobial activity of the crude essential oil was assayed against five bacteria. The best result was obtained against Staphylococcus aureus.

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Section: Resultsmentioning

confidence: 99%

Chiral Analysis of Monoterpenes in Volatile Oils From Propolis

Simionatto

Facco

Morel

et al. 2012

J. Chil. Chem. Soc.

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“…After removal of excess of reagent in a stream of N 2 , the sample was dissolved in CH 2 Cl 2 (0.5 mL) and used for gas chromatography. Gas chromatographic analysis: The separation of the enantiomers was achieved using a 15-m fused silica capillary (0.25 mm i. d.) coated with octakis(2,6-di-O-methyl-3-O-pentyl)-γ-cyclodextrin [24] (dissolved in polysiloxane OV 1701, 1:1, w/w) at 95°C. A Carlo Erba Model 2150 gas chromatograph with split injection and flame ionization detection was used with 0.4 bar H 2 as carrier gas.…”

Section: Separation Of the Enantiomers Of 11mentioning

confidence: 99%

Enantiomerically Pure Amines as Substrates for the Ti‐Catalyzed Hydroamination of Alkynes

et al. 2004

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For two representative reactions employing enantiomerically pure (S)‐1‐phenylethylamine and (S)‐1‐cyclohexylethylamine it is shown that Ti‐catalyzed hydroamination reactions of alkynes do not generally take place without partial racemization at the chiral center adjacent to the nitrogen atom. However, identified from a selection of nine Ti catalysts, Cp*2TiMe2 and at least two other catalysts can be used for racemization‐free hydroamination reactions of alkynes. Furthermore, the amount of racemization can be reduced significantly by the addition of pyridine to the reaction mixture. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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“…14 Many different chiral stationary phases based on permethylated cyclodextrins have been reported for their capability to solve different enantiomeric pairs in plant volatiles and essential oils. 12,13,15,16 Due to the complexity of the composition of some essential oils and the similarity in chemical structure of their components, some terpenes usually coelute in gas chromatography (GC). To solve this problem, high performance liquid chromatography (HPLC) may be a useful alternative as a pre-fractionation technique.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric Ratio Changes of Terpenes in Essential Oils from Hybrid Eucalyptus grandis × E. tereticornis and its Pure Species

Naspi¹,

Costa²,

Lucı́a³

et al. 2017

J. Braz. Chem. Soc.

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Some Eucalyptus species produce oils with biological activities and the effect of their interspecific hybridization on the enantiomeric composition of terpenes has not been reported. The enantiomeric excesses of monoterpenes in the essential oil of Eucalyptus grandis × E. tereticornis and its parental taxa were determined by gas chromatography-mass spectrometry (GC-MS), and to resolve coelutions problems by preparative high performance liquid chromatography (HPLC) and GC-MS with two columns in series. The essential oil composition of the hybrid presented qualitative and quantitative differences with the composition of its parental taxa. Great differences were found for the enantiomeric ratio in monoterpene alcohols among the three essential oils. Our results suggest that the enantiomeric analysis can be a reliable method for the study of how the interspecific hybridization can module the enantiomeric chemical profile in Eucalyptus essential oils. These results suggest the use of interspecific hybridization to improve or expand the source of bioactive compounds.

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New, selectively substituted cyclodextrins as stationary phases for the analysis of chiral constituents of essential oils

Cited by 137 publications

References 14 publications

Chiral Analysis of Monoterpenes in Volatile Oils From Propolis

Chiral Analysis of Monoterpenes in Volatile Oils From Propolis

Enantiomerically Pure Amines as Substrates for the Ti‐Catalyzed Hydroamination of Alkynes

Enantiomeric Ratio Changes of Terpenes in Essential Oils from Hybrid Eucalyptus grandis × E. tereticornis and its Pure Species

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