Enantiomeric distribution of selected terpenes for authenticity assessment of Australian Melaleuca alternifolia oil

Wong, Yong Foo; Davies, Noel W.; Chin, Sung‐Tong; Larkman, Tony; Marriott, Philip J.

doi:10.1016/j.indcrop.2015.01.066

Cited by 25 publications

(33 citation statements)

References 17 publications

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“…Currently, enantioselective gas chromatography (eGC) is the most widely used technique for enantiomeric separation of chiral volatile organic compounds. Several eGC methods have been recently reported for the separation of a range of terpenic compounds in TTO [8,9]. However, classical eGC methods may be incapable of distinguishing the target enantiomers from other interfering compounds in the sample matrix; non-specific co-elutions may arise.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of fast enantioselective multidimensional gas chromatography methods for monoterpenic compounds: Authenticity control of Australian tea tree oil

Wong

West

Chin

et al. 2015

Journal of Chromatography A

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Section: Introductionmentioning

confidence: 99%

Evaluation of fast enantioselective multidimensional gas chromatography methods for monoterpenic compounds: Authenticity control of Australian tea tree oil

Wong

West

Chin

et al. 2015

Journal of Chromatography A

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“…In addition, chiral compounds in specific species have a characteristic enantiomeric distribution that is attributable to stereoselectively controlled biogenetic formation mechanisms in the respective plant [16]. Therefore, the enantiomeric ratio of optically active components has been used successfully for the authenticity assessment of essential oils [17][18][19], or to differentiate natural compounds from those of synthetic origin, enabling the authenticity of desired products to be guaranteed [20]. Only a few investigations with limited samples [10,11,21,22] have been carried out to determine the enantiomeric distribution of the chiral compounds of P. nigrum, usually to determine their influence on the fragrance and taste of the plant material (spice) or the efficacy of therapeutic oil.…”

Section: Piper Nigrum Oil -Determination Of Selected Terpenes For Quamentioning

confidence: 99%

“…The authors define the Q-markers as intrinsic or processing/preparation-resultant chemical substances that exist in the raw materials and products of TCM (involving the pieces, decoctions, extractives, and Chinese patent medicines), and can be used as indicators for quality control of TCM. Studies involving enantiomeric compounds as chemical markers for authenticity assessment and quality control of Australian Melaleuca alternifolia oil have also been reported [17,18]. Based on these studies, the stereospecific composition for chiral compounds, such as terpinen-4-ol, has been incorporated into the ISO monograph as a secondary criterion for quality control of tea tree oil.…”

Section: Piper Nigrum Oil -Determination Of Selected Terpenes For Quamentioning

confidence: 99%

Piper nigrum Oil – Determination of Selected Terpenes for Quality Evaluation

et al. 2018

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The growing demand and commercial value of black pepper (Piper nigrum) has resulted in considerable interest in developing suitable and cost-effective methods for chemical characterization and quality evaluation purposes. In the current study, an extensive set of oil samples (n = 23) that were extracted by steam distillation from black pepper seeds was investigated to compare the chemical profiles of samples originating from nine major producing countries, as well as to identify potential chemical markers for quality evaluation. The twenty-two most abundant volatile compounds, mainly terpenes, in these oils were determined by conventional GC/MS analysis. Principal component analysis with this set of data revealed distinct clusters for samples that originated from China and Malaysia. Relatively low concentrations of sabinene (< 0.2%) and high concentrations of 3-carene (10.9 – 21.1%) were observed in these samples, respectively, compared to oil samples from other countries. The enantiomeric distributions of key terpene markers, viz., β-pinene, sabinene, limonene, and terpinen-4-ol, were determined by chiral GC/MS analysis. Interestingly, for these four monoterpenes, levo-isomers were found to be predominant, emphasizing the highly conserved enzymatic processes occurring in P. nigrum. Moreover, consistent enantiomeric ratios ((−) isomer/(+) isomer) of 92.2 ± 3.0% for β-pinene, 94.8 ± 2.8% for sabinene, 60.7 ± 1.1% for limonene, and 78.3 ± 1.3% for terpinen-4-ol were observed, independent of geographical location. These results demonstrate the potential of using stereospecific compositions as chiral signatures for establishing the authenticity and quality of black pepper oil.

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“…Up to now, several approaches have been proposed to manufacture microcapsules, such as complex coacervation, emulsion polymerization, in situ polymerization,solvent evaporation and spray drying methods. Chen et al microcapsulated tea tree oil with sodium alginate/quaternary ammonium salt by means of complex coacervation, in which 5 wt% sodium hydroxide solution was added to adjust the pH value. Moreover, the addition of calcium chloride(CaCl2) improved the encapsulation efficiency of aroma.…”

Section: Introductionmentioning

confidence: 99%

Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium bromide (TADAB) and its potential applications in cosmetics

Song

Chen

2017

Flavour & Fragrance J

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The formation of apple aroma microcapsules was achieved by sodium alginate (SA) and tetradecylallydimethylammonium bromide (TADAB) as shells based on complex coacervation‐emulsion polymerization. Alkyl alcohol polyoxyethylene ether was employed as emulsifier. Pentaerythritol tetraacrylate (PETRA) was used as a crosslinking agent and methyl methacrylate (MMA) was applied as comonomer to copolymerize with TADAB. The aroma microcapsules were characterized by scanning electron microscopy (SEM). Results showed that the aroma microcapsules prepared under optimal conditions were core‐shell structure. The aroma microcapsules were sphere‐like shape with particle size between 20 to 50 μm. FT‐IR analysis results showed that the electrostatic interactions and polymerization occurred assuredly. TG‐DTA study indicated that the thermal stability of the aroma microcapsules crosslinked with MMA shell was improved, and the thermal resistant temperature was up to 110°C. Moreover, the encapsulation efficiency of aroma microcapsules was measured by ultraviolet–visible near‐infrared spectrophotometer. In the surfactant solution, the release of aroma was quick during the first 8 hours, losing ca. 10.8% aroma encapsulated, however, there was no more else aroma dissolving out from the 9th hour. In open conditions, the encapsulation efficiency of the aroma microcapsules kept 66.57% after 48 hours, compared with the encapsulation efficiency going down alone if the microcapsules were milled.

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Enantiomeric distribution of selected terpenes for authenticity assessment of Australian Melaleuca alternifolia oil

Cited by 25 publications

References 17 publications

Evaluation of fast enantioselective multidimensional gas chromatography methods for monoterpenic compounds: Authenticity control of Australian tea tree oil

Evaluation of fast enantioselective multidimensional gas chromatography methods for monoterpenic compounds: Authenticity control of Australian tea tree oil

Piper nigrum Oil – Determination of Selected Terpenes for Quality Evaluation

Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium bromide (TADAB) and its potential applications in cosmetics

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