Essential oil of two chemotypes of Mentha suaveolens during ontogenesis

Hendriks, H.; Os, F. H. L. van

doi:10.1016/0031-9422(76)85115-1

Cited by 33 publications

(18 citation statements)

References 14 publications

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“…In other characteristics, they are rather similar, and they are probably typical of enzymes likely to be present in other species where the reduction of monoterpene ketones is a characteristic feature of development (7,8,10,11,20,21). Although the enzymes reported here are theoretically dehydrogenases (i.e.…”

Section: Methodsmentioning

confidence: 76%

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves

Kjonaas¹,

Martinkus-Taylor²,

Croteau³

1982

Plant Physiol.

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The monoterpene ketone l-menthone is specifically converted to I-menthol and I-menthyl acetate and to d-neomenthol and d-neomenthyl-f8-nglucoside in mature peppermint (Mentha piperita L. cv. Black Mitcham) leaves. The selectivity of product formation results from compartmentation of the menthol dehydrogenase with the acetyl transferase and that of the neomenthol dehydrogenase with the glucosyl transferase. Soluble enzyme preparations, but not particulate preparations, from mature peppermint leaves catalyzed the NADPH-dependent reduction of 1-menthone to both epimeric alcohols, and the two dehydrogenases responsible for these stereospecific transformations were resolved by affinity chromatography on Mitrex Gel Red A. Both enzymes have a molecular weight of approximately 35,000, possess a Km for NADPH of about 2 x 10' M, are very sensitive to inhibition by thiol-directed reagents, and are not readily reversible. The menthol dehydrogenase showed a pH optimum at 7.5, exhibited a Km for 1-menthone of about 2.5 x 10' M, and also reduced disomenthone to d-neoisomenthol. The neomenthol dehydrogenase showed a pH optimum at 7.6, exhibited a K. for I-menthone of about 2.2 x 10' M, and also reduced d-isomenthone to d-isomenthol. These stereochemically distinct, but otherwise similar, enzymes are of key importance in determining the metabolic fate of menthone in peppermint, and they are probably typical of the class of dehydrogenases thought to be responsible for the metabolism of monoterpene ketones during plant development.appears to be a common feature of maturing essential oil plants. In peppermint, the metabolic disposition of the diastereomeric reduction products of 1-menthone is highly specific in that only 1-menthyl acetate (with little d-neomenthyl acetate) and d-neomenthyl-,f-D-glucoside (with little l-menthyl-fi-D-glucoside) are formed (6, 12). In vivo experiments, using labeled CO2, menthone, menthol and neomenthol as precursors, provided compelling evidence that compartmentation effects, and not the substrate specificity of the transferases, were responsible for the selectivity of pathways observed; this conclusion was confirmed by isolation and characterization of the acetyl CoA:monoterpenol acetyltransferase and the UDP-glucose:monoterpenol glucosyltransferase involved (5, 18). The nature of the terpenyl moiety of the acetate and ,B-D-glucoside is, thus, determined at the menthone reduction step by compartmentation of these stereospecific reactions with the appropriate, relatively nonselective, transferase. Consistent with chemical considerations (15) and with earlier genetic studies (13,19), such a metabolic scheme requires the presence in peppermint of two stereochemically distinct dehydrogenases. The NADPH-dependent conversion of d-pulegone to menthol (presumably via menthone) by extracts of peppermint leaves has been detected by Loomis and coworkers (3), suggesting the existence of one of the necessary enzymes. In this communication, we describe in detail the separation and characterization of t...

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Section: Methodsmentioning

confidence: 76%

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves

Kjonaas¹,

Martinkus-Taylor²,

Croteau³

1982

Plant Physiol.

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“…We also demonstrated that essentially all of the remaining en- (10) that both C6-and C3-oxygenated p-menthanes are derived from a common dioxygenated precursor (a diosphenolene) is clearly untenable. Similarly, proposals (9,21,23,25) that the C3-oxygenated series is formed by the conversion of terpinolene to piperitenone are incorrect.…”

Section: Enzyme Activity Measurementsmentioning

confidence: 86%

“…Although organoleptic evaluation of the oil of mutant 643 had suggested an abnormal composition, the analytical results were nevertheless surprising in that over 85% of the oil was composed of C3-oxygenated monoterpenes (Table I), of which well over half were 3-keto-1,2-oxides ( Fig. 1 M. cordifolia chemotypes (10,18), but the presence of these compounds and their C3-oxygenated congeners in spearmint types is unusual (17,22). A developmental study of oil compositional change as a function of leaf maturity of plants grown under controlled conditions indicated that the expansion of Scotch spearmint leaves from 0.5 cm to over 5 cm was accompanied by a gradual decrease in limonene content from over 20% to about 15%, with a gradual increase in carvone content from 50% to about 70%.…”

Section: Essential Oil Analysismentioning

confidence: 99%

Biochemical Characterization of a Spearmint Mutant That Resembles Peppermint in Monoterpene Content

Croteau¹,

Karp²,

Wagschal³

et al. 1991

Plant Physiol.

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A radiation-induced mutant of Scotch spearmint (Mentha x graclis) was shown to produce an essential oil containing principally C3-oxygenated p-menthane monoterpenes that are typical of peppermint, instead of the CS-oxygenated monoterpene family characteristic of spearmint. In vitro measurement of all of the enzymes responsible for the production of both the C3-oxygenated and CS-oxygenated families of monoterpenes from the common precursor (-)-limonene indicated that a virtually identical complement of enzymes was present in wild type and mutant, with the exception of the microsomal, cytochrome P-450-dependent (-)-limonene hydroxylase; the C6-hydroxylase producing (-)-trans-carveol in the wild type had been replaced by a C3-hydroxylase producing (--trans-isopiperitenol in the mutant. Additionally, the mutant, but not the wild type, could carry out the cytochrome P-450-dependent epoxidation of the ai-unsaturated bond of the ketones formed via C3-hydroxylation. Although present in the wild type, the enzymes of the C3-pathway that convert trans-isopiperitenol to menthol isomers are synthetically inactive because of the absence of the key C3-oxygenated intermediate generated by hydroxylation of limonene. These results, which clarify the origins of the C3-and CS-oxygenation patterns, also allow correction of a number of earlier biogenetic proposals for the formation of monoterpenes in Mentha.The monoterpene constituents of the essential oils of peppermint (Mentha piperita L.) and spearmint (native = Mentha spicata L.; Scotch = Mentha x gracilis [28]) are distinguished by the position of oxygenation on the p-menthane ring3 (18,25). Peppermint produces almost exclusively monoterpenes bearing an oxygen function at C3, such as menthone and menthol, whereas spearmint species produce almost exclusively monoterpenes bearing an oxygen function at C6, typi-

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“…These include piperitone oxide (Hendriks et al, 1976;Holeman et al, 1985;Oumzil et al, 2002) and piperitenone oxide (Koliopoulos et al, 2010;Holeman et al, 1985;Oumzil et al, 2002;Sutour et al, 2010).…”

Section: Discussionmentioning

confidence: 99%

“…Some chemotypes of M. suaveolens showed high percentage of ketones such as pulegone (Oumzil et al, 2002;Sutour et al, 2008;Velasco-Negueruela et al, 1996), piperitenone (Sutour et al, 2010) and dihydrocarvone (Hendriks et al, 1976).…”

Section: Discussionmentioning

confidence: 99%

Chemical composition of the essential oil and botanical study of the flowers ofMentha suaveolens

El-Kashoury

El‐Askary

Kandil

et al. 2014

Pharmaceutical Biology

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Context: Herbal medicines play a paramount role in the treatment of wide range of diseases, so there is a growing need for their quality control and standardization. Traditionally, histological and morphological inspections have been the usual methods to authenticate herbs intended for medicinal applications. Mentha suaveolens Ehrh. (Lamiaceae) is native to Africa Temperate Asia and Europe and it's cultivated in Egypt. Objective: The macro-and micromorphology of the flowers of M. suaveolens Ehrh. cultivated in Egypt were studied to find the diagnostic characters of this species. In addition, the chemical composition of the essential oil of the flowers was also studied to define the chemotype of the plant. Materials and methods: Photographs of macro-and micromorphology were taken using Casio and Leica DFC500 digital cameras, respectively. In addition, the essential oil was prepared by hydrodistillation followed by gas chromatographic/mass spectrometric (GC/MS) analysis for identification of its components. Results: The macro-and micromorphological characteristics of M. suaveolens were determined. The yield of the essential oil obtained by hydrodistillation from M. suaveolens flowers was 1.7% calculated on dry weight basis. GC/MS analysis of the oil resulted in identification of 29 components, which amounted to 99.77% of the total oil composition. The major component was carvone (50.59%) followed by limonene (31.25%). Discussion and conclusion: The results obtained herein revealed for the macro, micromorphological and chemical composition characteristics of the flowers. The results of GC/MS analysis of the essential oil supported that M. suaveolens cultivated in Egypt could be categorized as carvone-rich chemotype since this compound pertained its high relative percentile.

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Essential oil of two chemotypes of Mentha suaveolens during ontogenesis

Cited by 33 publications

References 14 publications

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves

Biochemical Characterization of a Spearmint Mutant That Resembles Peppermint in Monoterpene Content

Chemical composition of the essential oil and botanical study of the flowers ofMentha suaveolens

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