Enantiomeric analysis of monoterpenes in Oba-kuromozi (Lindera umbellata var. membranacea)

Inoue, Risa; Takahashi, Koetsu; Iiduka, Yoshiaki; Arai, Daisuke; Ashitani, Tatsuya

doi:10.1007/s10086-017-1686-4

Cited by 4 publications

(4 citation statements)

References 13 publications

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“…Recently, a noteworthy discovery regarding the enantiomers of linalool was reported by a study of L. umbellata var. membranacea, which identified a high proportion of the (R)-(−) and (S)-(+) forms in the leaves and twigs, respectively [13]. Similar results have also been reported for the leaves and twigs of Aniba rosaeodora, a Lauraceae species naturally distributed in the Central Amazon region [26].…”

Section: Enantiomeric Distribution Of Linaloolsupporting

confidence: 72%

“…Recently, the discovery that the enantiomer ratio of linalool, which is the major oxygenated monoterpenoid in the leaves of L. umbellata var. membranacea, tends to favor the (R)-(−) form in leaves and in the (S)-(+) form in twigs, was reported by Inoue et al [13]. Moreover, the four types of linalool oxide (furanoid) have been identified in their leaves and twigs according to conformational predominance [14].…”

Section: Introductionmentioning

confidence: 71%

“…Moreover, the new findings regarding linalool included the observation that, although most individuals showed similar enantiomeric properties to those of L. umbellata var. membranacea [13], there were a few individuals with a high (R)-(−)-linalool content in the twigs, and the proportion of enantiomers remained constant in each individual, regardless of the season. The new findings on flavonoids included the observation that the total phenolic content of leaves was more than twice that of twigs, that the leaves tended to contain more chalcones and twigs more flavanones, and that the content between chalcones (pinocembrin chalcone vs. pinostrobin chalcone) and between flavanones (pinocembrin vs. pinostrobin) was positively correlated in both leaves and twigs.…”

Section: Discussionmentioning

confidence: 95%

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The variability of terpenoids and flavonoids in native Lindera umbellata from the same region

et al. 2022

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The leaves and twigs of Lindera spp. have long been used as a herbal medicine and toothpicks in Japan. However, little is known about individual variations in the extractives of these species, because many previous studies have not distinguished extractives between individuals. In this study, we investigated the extractives of L. umbellata at the individual level. The detailed identification of the inter- and intra-individual variations in the major terpenoids and flavonoids in native L. umbellata may greatly contribute to the development of cultivation techniques and the effective use of forest resources. The contents of major components of L. umbellata, including four terpenoids (1,8-cineole, linalool, geraniol, and geranyl acetate) and five low-molecular-weight phenolics (pinocembrin chalcone, pinocembrin, pinostrobin chalcone, pinostrobin, and 5,6-dehydrokawain), were analyzed in leaves and twigs seasonally (June, August, and October). The compositions of the major terpenoids were strongly dependent on the properties of each individual and were generally independent of leaves and twigs. Moreover, geranyl acetate was characteristically present in the twigs of some individuals. As new findings regarding linalool, some individuals showed characteristic enantiomeric excesses, presumably because of biotic factors, and the proportion of these enantiomers was kept constant in each individual, regardless of the season. The total phenolic contents in leaves were more than twice those detected in twigs, and the leaves tended to contain more chalcones and twigs more flavanones. Furthermore, the contents of chalcones (pinocembrin chalcone vs. pinostrobin chalcone) and flavanones (pinocembrin vs. pinostrobin) were positively correlated in both leaves and twigs. The coefficient of variation (CV) clearly showed that the content of the major terpenoids was determined by inter-individual rather than intra-individual differences. Although the results obtained in this study should at present only be applicable to a limited population native to specific regions, our findings provide key knowledge in considering the sustainable use of L. umbellata.

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Section: Enantiomeric Distribution Of Linaloolsupporting

confidence: 72%

Section: Introductionmentioning

confidence: 71%

Section: Discussionmentioning

confidence: 95%

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The variability of terpenoids and flavonoids in native Lindera umbellata from the same region

et al. 2022

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“…Analytes: Terpinen-4-ol, limonene, α-terpineol. Inoue et al (2018) Lindera umbellata var. membranacea…”

Section: Using Solvent and Solvent Injectionmentioning

confidence: 99%

Measurement of Enantiomer Ratios for Five Monoterpenes From Six Conifer Species by Cartridge Tube-Based Passive Sampling Adsorption/Thermal Desorption (ps-ATD)

Wang

Luo

Rosenstiel

et al. 2022

Preprint

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Abstract. Many monoterpenes have at least two different stereochemical forms, and many biosynthetic pathways have long been known to favor one product over the other(s). A rapid method was developed and used in the determination of the (−/+) enantiomeric distributions for α-pinene, β-pinene, camphene, limonene, and β-phellandrene as emitted by plant material from six conifer species. The six species included two pine species Pseudotsuga menziesii and Pinus ponderosa, and four cypress species, Chamaecyparis lawsoniana, Thuja plilcata, Juniperus chinensis, and Thuja occidentalis.) The method involved passive sampling adsorption/thermal desorption (ps-ATD). During sampling, the cartridge tube was placed in a 60 mL glass vial with plant material for 1 h. Sample analytes were thermally transferred to a chiral gas chromatography (GC) column. Detection was by mass spectrometry (MS). The six species exhibited different emission patterns for the five monoterpenes in the −/+ totals, although within a given species the distributions among the five monoterpenes were similar across multiple plants. β-pinene dominated in P. menziesii and P. ponderosa, and α-pinene dominated in T. plicata and T. occidentalis. The chiral separations revealed differences in the −/+ enantiomeric distributions among the species. The (−) enantiomers of α-pinene and β-pinene dominated strongly in P. menziesii and P. ponderosa; the (−) enantiomer of β-phellandrene dominated in C. lawsoniana. The method precision was excellent.

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Antitermitic and antifungal properties of enantiopure linalool and furanoid linalool oxide confirmed in Lindera umbellata var. membranacea

Satoh

Kusumoto

Matsui

et al. 2021

Journal of Wood Chemistry and Technology

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Enantiomeric analysis of monoterpenes in Oba-kuromozi (Lindera umbellata var. membranacea)

Cited by 4 publications

References 13 publications

The variability of terpenoids and flavonoids in native Lindera umbellata from the same region

The variability of terpenoids and flavonoids in native Lindera umbellata from the same region

Measurement of Enantiomer Ratios for Five Monoterpenes From Six Conifer Species by Cartridge Tube-Based Passive Sampling Adsorption/Thermal Desorption (ps-ATD)

Antitermitic and antifungal properties of enantiopure linalool and furanoid linalool oxide confirmed in Lindera umbellata var. membranacea

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