Natural variability of the enantiomeric composition of bioactive chiral terpenes in Mentha piperita

Castillo, Marı́a Luisa Ruiz del; Blanch, Gracia Patricia; Herráiz, Marta

doi:10.1016/j.chroma.2004.08.055

Cited by 35 publications

(23 citation statements)

References 19 publications

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“…Specifically, these enantiomers were (-)-menthone, (-)-neomenthol, (-)-menthol, and (+)-isomenthol. This is in agreement with data previously found for a number of samples in our laboratory by employing solid phase microextraction (SPME) [19] as well as by other authors using different analytical techniques [20][21][22]. Although the peak areas obtained (Table 1) were similar when applying any of the set of values of the tested parameters, 208C and 3 min were finally selected as the PTV temperature and the purge time, respectively, since they provided acceptable areas also showing high effectiveness in solvent elimination.…”

Section: Resultssupporting

confidence: 93%

Use of a superabsorbent polymer for the pre‐concentration of volatile components from complex matrices

Flores

Herráiz

Castillo³

2006

J of Separation Science

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A polymeric material commonly used as a superabsorbent in the sanitary industry is proposed for the first time for analytical purposes. Specifically, we have evaluated in this work the possibility of using this material in a programmed-temperature vaporizer (PTV) injector for the introduction of large volume samples. To that end, the viability of this superabsorbent polymer as a retaining material was first studied by testing the stability of its absorption capacity in the presence of various solvents and at various temperatures. Subsequently, its effectiveness in the isolation of menthol and its isomers from Mentha piperita essential oil as well as gamma-lactones from peach essential oil was assessed. For that purpose, optimization of different variables, namely PTV temperatures during sampling, purge times, and desorption temperatures, involved in the solvent elimination was performed. Additionally, the information obtained was compared with that acquired for the adsorbent material Tenax TA. The results shown in this work proved not only the viability of using this superabsorbent polymer in analytical procedures but also demonstrated its advantages over the adsorbent Tenax TA in attaining internal GC concentration of a sample by introducing large volumes via PTV.

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Section: Resultssupporting

confidence: 93%

Use of a superabsorbent polymer for the pre‐concentration of volatile components from complex matrices

Flores

Herráiz

Castillo³

2006

J of Separation Science

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“…The present results agree with previous studies, which demonstrated that the toxicities of the essential oils extracted from various plant samples were mainly related to their major components. Barcelona (Spain) [67]. The plants grown in Norway showed the presence of menthol and menthone as the main compounds [68].…”

Section: Contact and Fumigant Toxicity Methodsmentioning

confidence: 99%

Assessment of the Toxicity of Natural Oils from Mentha piperita, Pinus roxburghii, and Rosa spp. Against Three Stored Product Insects

et al. 2019

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Three natural oils extracted from Mentha piperita, Pinus roxburghii, and Rosa spp. were assessed in order to determine their insecticidal activity against the adults of three stored product insects: the rice weevil (Sitophilus oryzae L.), the lesser grain borer (Rhyzopertha dominica, Fabricius), and the red flour beetle (Tribolium castaneum, Herbst.). By Gas chromatography–mass spectrometry (GC/MS) analysis, the main compounds in the n-hexane oil from Rosa spp. were determined to be methyl eugenol (52.17%), phenylethyl alcohol (29.92%), diphenyl ether (7.75%), and geraniol (5.72%); in the essential oil from M. piperita, they were menthone (20.18%), 1,8-cineole (15.48%), menthyl acetate (13.13%), caryophyllene (4.82%), β-pinene (4.37%), and D-limonene (2.81%); and from the foliage of P. roxburghii, they were longifolene (19.52%), caryophyllene (9.45%), Δ-3-carene (7.01%), α-terpineol (6.75%), and γ-elemene (3.88%). S. oryzae and R. dominica were reared using sterilized wheat grains, and T. castaneum was reared on wheat flour mixed with yeast (10:1, w/w), all under laboratory conditions (27 ± 1 °C and 65% ± 5% Relative humidity (R.H). Two toxicity bioassays were used, as well as contact using thin film residues and fumigation bioassays. The results indicated that M. piperita caused a high toxicity for S. oryzae compared to other insects. High significant variations were observed between the tested M. piperita doses against the stored insects, and this natural material could be used to control insects that infect the grains. Also, the data indicated that the Rosa spp. oil had a low-toxicity effect against these insects compared to other oils. We recommend using natural oils against the stored weevils and petals, rather than the chemical agent, so as to serve human health.

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“…The order of elution for each enantiomer was assigned by comparison with authentic standards and is in concordance with those reported in bibliography using equivalent stationary phases. 9,12,13,16 The elution orders of (+) and (-) enantiomers of linalool and α-terpineol were obtained from previous reports with equivalent column (Table 5). 9,13 At this moment, we were able to determine the enantiomeric excess of six enantiomeric pairs: α-pinene, camphene, linalool, 4-terpineol, borneol and α-terpineol.…”

Section: Resultsmentioning

confidence: 99%

“…10 The analysis of enantiomers in an essential oil can be useful to determine their authenticity in those cases in which one of its components is present in a high enantiomeric purity, or exists in a specific enantiomeric ratio. 11,12 Moreover, the determination of chiral compounds can be used for defining chemotypes in aromatic plants and for establishing their geographical origin. 13 In addition to this, the enantiomeric ratio of terpenes can vary depending on the part of the plant in study.…”

Section: Introductionmentioning

confidence: 99%

“…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%

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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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Natural variability of the enantiomeric composition of bioactive chiral terpenes in Mentha piperita

Cited by 35 publications

References 19 publications

Use of a superabsorbent polymer for the pre‐concentration of volatile components from complex matrices

Use of a superabsorbent polymer for the pre‐concentration of volatile components from complex matrices

Assessment of the Toxicity of Natural Oils from Mentha piperita, Pinus roxburghii, and Rosa spp. Against Three Stored Product Insects

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

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