Essential Oils of<i>Lamiaceae</i>with High Content of α-, β-Pinene and Limonene Enantiomers

Shutava, H. G.; Kavalenka, Natallia A.; Supichenka, NHalina N.; Леонтьев, Виктор Николаевич; Shutava, NTatsiana G.

doi:10.1080/0972060x.2014.884816

Cited by 8 publications

(7 citation statements)

References 18 publications

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“…Inspection of a review 6 revealed that racemic epoxythymols were found in Doronicum hungaricum 14 and Piptothrix areolare, 15 and the lack of optical activity was confirmed using the 1 H NMR chiral shift reagent Eu(THC) 3 . 15 Such rare enantiomeric behaviors were also observed when studying Agastache rugosa, Mentha piperita, Mentha x piperita, 16 and Anethum graveolens. 17 In order to shed some light on this behavior, we now report on the unprecedented observation that each enantiomer of the epoxythymol areolal (1), or its near racemic mixture, can be dominant in its plant source, P. areolare, at different stages.…”

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confidence: 67%

“…Inspection of a review revealed that racemic epoxythymols were found in Doronicum hungaricum and Piptothrix areolare , and the lack of optical activity was confirmed using the 1 H NMR chiral shift reagent Eu(THC) 3 . Such rare enantiomeric behaviors were also observed when studying Agastache rugosa , Mentha piperita , Mentha x piperita , and Anethum graveolens …”

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confidence: 94%

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Configurational Variation of a Natural Compound within Its Source Species. The Unprecedented Case of Areolal in Piptothrix areolare

et al. 2019

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The exceptional case of a natural compound that shows drastic absolute configuration variations within the same species was examined. Sequential samples of areolal (1) isolated from Piptothrix areolare showed dextrorotatory (ee 32%), almost racemic (ee 4%), levorotatory (ee 82%), and again dextrorotatory (ee 10%) values. Enantiomeric compositions of this epoxythymol derivative were determined from individual plant specimens collected from the same geographical location over a 46-day period, which were processed using the same extraction and isolation methods. Detection of this unusual phenomenon was possible by analysis of NMR data recorded in the presence of BINOL as a chiral solvating agent. The absolute configuration of (−)-(8S)-areolal followed from vibrational circular dichroism data of an enantiomerically enriched sample, while single-crystal X-ray diffraction and supramolecular analyses revealed interactions that diminish the crystal entropy in rac-1. These results might be related with environmental factors and biochemical processes, suggesting the need of strict evaluations of enantiomeric composition of natural products that could be considered for human applications.

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confidence: 67%

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confidence: 94%

Configurational Variation of a Natural Compound within Its Source Species. The Unprecedented Case of Areolal in Piptothrix areolare

et al. 2019

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“…Agastache species are traditionally used as spices due to the characteristic anise-like aroma given by the essential oil. Different factors could determine changes in essential oil composition, such as cultivation methods, origin, age of the plant, weather conditions [ 40 , 41 ], and chemotype differences [ 42 ].…”

Section: Phytochemical Profilementioning

confidence: 99%

Agastache Species: A Comprehensive Review on Phytochemical Composition and Therapeutic Properties

Nechita

Toiu

Benedec

et al. 2023

Plants

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The Agastache genus is part of the Lamiaceae family and is native to North America, while one species, Agastache rugosa (A. rugosa), is native to East Asia. A review on the phytochemistry and bioactivity of Agastache genus was last performed in 2014. Since then, a lot of progress has been made on the characterization of the phytochemical and pharmacological profiles of Agastache species. Thus, the purpose of this paper is to present a summary of the findings on the phytochemistry and biological effects of several Agastache species, including both extracts and essential oil characterization. We performed a comprehensive search using PubMed and Scopus databases, following PRISMA criteria regarding the study selection process. The available data is focused mainly on the description of the chemical composition and bioactivity of A. rugosa, with fewer reports referring to Agastache mexicana (A. mexicana) and Agastache foeniculum (A. foeniculum). Agastache species are characterized by the dominance of flavonoids and phenolic acids, as well as volatile compounds, particularly phenylpropanoids and monoterpenes. Moreover, a series of pharmacological effects, including antioxidant, cytotoxic, antimicrobial, anti-atherosclerotic, and cardioprotective properties, have been reported for species from the Agastache genus.

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“…citrata. 5 A specific case, where the enantiomeric purity is modified from one enantiomer to the other one, occurs for linalool in Jasmonium grandiflorum, where in above 12 h (R)-linalool is the major enantiomer in the bottom flower stage while (S)-linalool appears as the major enantiomer when the flower opened. Such a variation can be related with DNA, as well as the volatility of compounds.…”

Section: Introductionmentioning

confidence: 99%

“…The same phenomenon was described for limonene, sabinene, and terpinen‐4‐ol in an annual study of oil samples from Pittosporum undulatum , 4 as well as for the enantiomeric variation of limonene, α ‐pinene, and β ‐pinene from the essential oils of Agastache rugosa and Mentha piperita var. citrata 5 . A specific case, where the enantiomeric purity is modified from one enantiomer to the other one, occurs for linalool in Jasmonium grandiflorum , where in above 12 h ( R )‐linalool is the major enantiomer in the bottom flower stage while ( S )‐linalool appears as the major enantiomer when the flower opened.…”

Section: Introductionmentioning

confidence: 99%

Chiral NMR analysis reveals the environmental dependence of areolal scalemization in Piptothrix areolare

et al. 2022

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The occurrence of racemic and enantiomerically enriched (scalemic) mixtures of secondary metabolites in their natural sources is a rare phenomenon. The unprecedent case of enantiomeric variations from levorotatory to dextrorotatory, and back to levorotatory, passing through an almost racemic mixture, was recently documented for areolal, the major epoxythymol of Piptothrix areolare. In an attempt to shed some light to understand the reasons for such an unusual behavior, herein, we evaluated this phenomenon by correlating the areolal enantiomeric purity with several environmental variables, including temperature, humidity, rain precipitation, wind speed, and radiation during over 1 year of the plant life cycle. The specific rotation and enantiomeric excess determined by 1H‐NMR‐BINOL measurements provided the scalemic variations of areolal samples isolated from the roots collected from the same location along a 427‐day period. The 1H‐NMR‐BINOL methodology provided better sensitivity to enantiomeric variations than specific rotation measurements. Statistical data, including matrix correlation analysis, exploratory analysis by heatmap plotting, and the principal component analysis (PCA), suggested direct correlation of the scalemic variation with humidity, rain precipitation, and radiation variables with the best PCA explanation (78.4%) and noncritical or poor correlations in PCA explained in 60.2% and 48.4%, respectively. When variations in the optical activity parameter of any metabolite are observed, the search for scalemic mixtures along their host plant life cycle should be undertaken. Herein, this phenomenon could be associated with interactions with soil microorganisms and with evolutionary aspects of Piptothrix areolare which belongs to Asteraceae, one of the most successfully adaptable plant families.

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Essential Oils ofLamiaceaewith High Content of α-, β-Pinene and Limonene Enantiomers

Cited by 8 publications

References 18 publications

Configurational Variation of a Natural Compound within Its Source Species. The Unprecedented Case of Areolal in Piptothrix areolare

Configurational Variation of a Natural Compound within Its Source Species. The Unprecedented Case of Areolal in Piptothrix areolare

Agastache Species: A Comprehensive Review on Phytochemical Composition and Therapeutic Properties

Chiral NMR analysis reveals the environmental dependence of areolal scalemization in Piptothrix areolare

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