Photochemical studies on jasmine oil

Toda, Hisayuki; Mihara, Satoru; Umano, Katsumi; Shibamoto, Takayuki

doi:10.1021/jf00117a022

Cited by 9 publications

(7 citation statements)

References 3 publications

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“…Two peaks in the GC chromatograms (detected in both samples 1 and 2) that were tentatively identified (based on mass spectral comparison with the MS from the Wiley-NIST data base) as methyl (2) and isopropyl (1) N-methylanthranilates were of great interest since nitrogen volatiles are known as potent floral volatiles that are difficult to detect and are frequently missed out during the analyses (Jabalpurwala et al, 2009). A literature survey on these two compounds gave the following results: the methyl ester of N-methylanthranilic acid (2) was previously reported from a number of Rutaceae species (belonging to one of the two sister subfamilies, Rutoideae and Aurantioideae, namely the genera Zanthoxylum (Detoni et al, 2009;Dreyer and Brenner, 1980), Citrus (Brophy et al, 2001;Jabalpurwala et al, 2009;Lota et al, 2000;Tomi et al, 2008), Fortunella Pino, 2009a, 2009b;Umano et al, 1994) and Murraya (Imai et al, 1989), respectively) with some sporadic (most frequently singular) occurrence (in low amount) in the unrelated genera Chamaecyparis (Thomas et al, 1966), Corydalis (Olesen and Knudsen, 1994), Jasminum (Calvarano, 1966;Cheng and Chao, 1979;Ito et al, 2002;Kaiser, 1988;Toda et al, 1983), Mangifera (Pino et al, 2005), Michelia (Kaiser, 1991), Siphonochilus A c c e p t e d M a n u s c r i p t 25 (Viljoen et al, 2002), and Trifolium (Honkanen et al, 1969). However, the isopropyl ester (1) has never been detected in a sample of natural origin.…”

Section: Resultsmentioning

confidence: 99%

Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth

Radulović

Miltojević

McDermott

et al. 2011

Journal of Ethnopharmacology

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Ethnopharmacological relevance: Mexican people employed infusion of leaves of Choisya ternata Kunth for their antispasmodic and "simulative properties". Aim of the study:In the present study the detailed GC and GC-MS analyses of the essential oil of Choisya ternata Kunth (Rutaceae) were performed. The presence of a minor constituent isopropyl N-methylanthranilate (1) was revealed among other identified volatiles. A synthesis of 1 was undertaken in order to corroborate this find and obtain gram quantities that would allow the testing of its biological activity (peripheral and central antinociceptive activity). Material and methods:The oils were investigated by GC and GC-MS. Synthesized compounds were spectrally characterized (UV-Vis, IR, 1D and 2D NMR, MS). The obtained synthetic samples of compounds were assayed for peripheral and central antinociceptive activity in two models (effects on acetic acid induced writhing in mice and the hot plate test for nociception). showed the lowest activity (with the methyl ester at 3 mg/kg still better than acetylsalicylic acid, at 200 mg/kg, in the first, or comparable with morphine, at 5 mg/kg, in the second test). Conclusion:This study once again revealed that detailed investigations of plant species with ethnopharmacologically documented activity may yield new natural compounds -a new alkaloid (ternanthranin), a volatile simple anthranilate that can be considered responsible for the antinociceptive activity of the crude plant extracts.

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Section: Resultsmentioning

confidence: 99%

Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth

Radulović

Miltojević

McDermott

et al. 2011

Journal of Ethnopharmacology

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“…To simplify the experiment, we used only indole in jasind, but at a slightly higher level (6%) than in natural jasmine oil to compensate for the lack of para-cresol. We note that the components in the model jasmine we created are present in natural jasmine (Verzele et al, 1981;Toda et al, 1983;Kaiser, 1988) with the exception of hexylcinnamic aldehyde, which has been found to be a useful building block of jasmine odor, and that the components in the model are sufficient to capture many aspects of natural jasmine.) All stimuli were diluted 1:5 in dipropylene glycol in such a way that the eight components would be present at the same level in jasmine and jasind regardless of the presence of indole.…”

Section: Methodsmentioning

confidence: 99%

How Pleasant and Unpleasant Stimuli Combine in Different Brain Regions: Odor Mixtures

Grabenhorst¹,

Rolls²,

Margot³

et al. 2007

J. Neurosci.

195

148

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Many affective stimuli are hedonically complex mixtures containing both pleasant and unpleasant components. To investigate whether the brain represents the overall affective value of such complex stimuli, or the affective value of the different components simultaneously, we used functional magnetic resonance imaging to measure brain activations to a pleasant odor (jasmine), an unpleasant odor (indole), and a mixture of the two that was pleasant. In brain regions that represented the pleasantness of the odors such as the medial orbitofrontal cortex (as shown by activations that correlated with the pleasantness ratings), the mixture produced activations of similar magnitude to the pleasant jasmine, but very different from the unpleasant indole. These regions thus emphasize the pleasant aspects of the mixture. In contrast, in regions representing the unpleasantness of odors such as the dorsal anterior cingulate and midorbitofrontal cortex the mixture produced activations that were relatively further from the pleasant component jasmine and closer to the indole. These regions thus emphasize the unpleasant aspects of the mixture. Thus mixtures that are found pleasant can have components that are separately pleasant and unpleasant, and the brain can separately and simultaneously represent the positive and negative hedonic value of a complex affective stimulus that contains both pleasant and unpleasant olfactory components. This type of representation may be important for affective decision making in the brain in that separate representations of different affective components of the same sensory stimulus may provide the inputs for making a decision about whether to choose the stimulus or not.

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“…The accelerated photochemical degradation of 'fresh' JA has been investigated, claiming that the material readily undergoes photochemical changes and an erosion of properties. 103 However, the nature of the product(s) formed during photoirradiation was not elucidated. On the other hand, photo-products of benzyl benzoate have never been found in JA.…”

Section: Ageing Of Jasmine Extractsmentioning

confidence: 99%

Jasminum grandiflorum flowers—Phytochemical complexity and its capture in extracts: a review

Joulain¹

2021

Flavour & Fragrance J

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The phytochemistry of the fragrant flowers of Jasminum grandiflorum is reviewed, highlighting the remarkable circadian interplay between the isoprenoid, polyketide and shikimate pathway in this plant, and outlining the challenges involved in capturing its metabolic profligacy into extracts. After presenting a detailed historical survey on the techniques developed for the production of jasmine extracts, the identification of their constituents, their associated sensory properties and their use for authentication purposes is discussed in detail.

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Photochemical studies on jasmine oil

Cited by 9 publications

References 3 publications

Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth

Identification of a new antinociceptive alkaloid isopropyl N-methylanthranilate from the essential oil of Choisya ternata Kunth

How Pleasant and Unpleasant Stimuli Combine in Different Brain Regions: Odor Mixtures

Jasminum grandiflorum flowers—Phytochemical complexity and its capture in extracts: a review

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