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The potential to produce and accumulate mono- and sesquiterpenes in lemon mint (Mentha aquatica var. citrata) glandular trichomes was evaluated. Volatiles were extracted using methyl-tert-butyl ether or solid phase micro extraction and determined by gas chromatography-mass spectrometry. The main components of the essential oil of lemon mint are the monoterpene alcohol linalool and its ester linalyl acetate. Sesquiterpenes, such as elemol, (E)-caryophyllene, and germacrene D, as well as the monoterpenes 1,8-cineole, β-myrcene, and β-(E)-ocimene, are also prominent. Most of the essential oil is localized in the glands, as leaves devoid of trichomes had very low essential oil levels. The quantities of all these components per leaf increased during leaf development until reaching the third whorl, and then the levels remained steady. Conversely, the essential oil content per gram fresh weight decreased with leaf development, but the decrease was not statistically significant at p = 0.05. Desalted cell-free extracts derived from isolated glandular trichomes were able to convert geranyl diphosphate into linalool. Lower amounts of geranyl diphosphate were also converted to other monoterpenes such as myrcene, α-pinene, β-pinene, limonene, β-(E)-ocimene, and nerol. Furthermore, the extracts were able to convert farnesyl diphosphate into the sesquiterpene (E)-caryophyllene and lesser amounts of other sesquiterpenes such as δ-cadinene, α-humulene, β-(E)-farnesene, and α-gurjunene. These cell-free extracts also efficiently catalyzed the formation of linalyl acetate from linalool and acetyl-coenzyme A. Our findings indicate that glandular trichomes of lemon mint, similar to other members of the Lamiaceae, contain unique enzymatic activities capable of the synthesis of mono- and sesquiterpene components of its essential oil.
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Aharoni, A., Giri, A.P., Verstappen, F.W., Bertea, C.M., Sevenier, R., Sun, Z., Jongsma, M.A., Schwab, W., Bouwmeester, H.J. 2004. Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16: 3110-3131.
Alonso, W.R., Rajaonarivony, J.I.M., Gershenzon, J., Croteau, R. 1992. Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha × piperita) and spearmint (M. spicata). J. Biol. Chem. 267: 7582-7587.
Bauer, K., Garbe, D., Surburg, H. 1990. Common fragrance and flavor materials, 4th ed. Wiley-VCH, Weinheim, Germany, p. 45.
Beekwilder, J., Alvarez-Huerta, M., Neef, E., Verstappen, F.W.A., Bouwmeester, H.J., Aharoni, A. 2004. Functional characterization of enzymes forming volatile esters from strawberry and banana. Plant Physiol. 135: 1865-1878.
Bohlmann, J., Meyer-Gauen, G., Croteau, R. 1998. Plant terpenoid synthases: molecular biology and phylogenetic analysis. Proc. Natl. Acad. Sci. USA 95: 4126-4133.
Bradford, M.M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal. Biochem. 72: 248-254.
Budavari, S., ed. 1989. The Merck Index. An encyclopedia of chemicals, drugs and biologicals. 12th ed. Merk & Company, Inc. Whitehouse Station, NJ, p. 939.
Burdock, G.A. 1995. Fenaroli's handbook of flavor ingredients, 3rd ed. CRC Press, Boca Raton, FL.
Chen, F., Tholl, D., D'Auria, J.C., Farooq, A., Pichersky, E., Gershenzon, J. 2003. Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell 15: 481-494.
Colby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, D.J., Croteau, R. 1993. 4S-limonene synthase from the oil glands of spearmint (Mentha spicata): cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene CyChSe. J. Biol. Chem. 268: 23016-23024.
Crowell, A.L., Williams, D.C., Davis, E.M., Wildung, M.R., Croteau, R. 2002. Molecular cloning and characterization of a new linalool synthase. Arch. Biochem. Biophys. 405: 112-121.
Davidovich-Rikanati, R., Sitrit, Y., Tadmor, Y., Iijima, Y., Bilenko, N., Bar, E., Carmona, B., Fallick, E., Dudai, N., Simon, J.E., Pichersky, E., Lewinsohn, E. 2007. Enrichment of tomato flavor by diversion of the early plastidial terpenoid pathway. Nat. Biotechnol. 25: 899-901.
Dudareva, N., D'Auria, C., Hee Nam, K., Raguso, R., Pichersky, E. 1998. Acetyl-CoA: benzylalcohol acetyltransferase—an enzyme involved in floral scent production in Clarkia breweri.Plant Cell 14: 297-304.
El-Sharkawy, I., Manrıquez, D., Flores, F.B., Regad, F., Bouzayen, M., Latche, A., Pech, J.C. 2005. Functional characterization of a melon alcohol acyl-transferase genefamily involved in the biosynthesis of ester volatiles. Identification of the crucial role of a threonine residue for enzyme activity. Plant Mol. Biol. 59: 345-362.
Gang, D.R., Wang, J., Dudareva, N., Nam, K.H., Simon, J.E., Lewinsohn, E., Pichersky, E. 2001. An investigation of the storage and biosynthesis of phenylpropenes in sweet basil. Plant Physiol. 125: 539-555.
Geremia, B. 1955. Rassengna Internazionale di Clinica e Therapie. Urban & Fisher, Academic Verlag, Berlin, Germany, Vol. 35, pp. 577-592.
Gershenzon, J., Maffei, M., Croteau, R. 1989. Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of Spearmint (Mentha spicata). Plant Physiol. 89: 1351-1357.
Gershenzon, J., McCaskill, D., Rajaonarivony, J.I.M., Mihaliak, C., Karp, F., Croteau, R. 1992. Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products. Anal. Biochem. 200: 130-138.
Gershenzon, J., McConkey, M.E., Croteau, R. 2000. Regulation of monoterpene accumulation in leaves of peppermint. Plant Physiol. 122: 205-213.
Gildemeister, E., Hoffman, F. 1961. Oils of Mentha species. In: Treibs, W., ed. Die Atherischen Ole. Akademic Verlag, Berlin, Germany, Vol. 7, pp. 246-421.
Harada, M., Ueda, Y., Iwata, T. 1985. Purification and some properties of alcohol acyltransferase from banana fruit. Plant Cell Physiol. 26: 1067-1074.
Holland, D., Larkov, O., Bar-Ya'akov, I., Bar, E., Zax, A., Brandeis, E., Ravid, U., Lewinsohn, E. 2005. Developmental and varietal differences in volatile ester formation and Acetyl-CoA: Alcohol Acetyl Transferase activities in apple (Malus domestica Borkh.) fruit. J. Agric. Food Chem. 53: 7198-7203.
Iijima, Y., Gang, D.R., Fridman, E., Lewinsohn, E., Pichersky, E. 2004. Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiol. 134: 370-379.
Jia, JW., Crock, J., Lu, S., Croteau, R., Chen, XY. 1999. (3R)-Linalool synthase from Artemisia annua L.; cDNA isolation, characterization and wound-induction. Arch. Biochem. Biophys. 372: 143-149.
Jirovetz, L., Buchbauer, G., Ngassoum, MB., Parmentier, M. 2005. Chemical composition and olfactory characterization of essential oils of fruits and seeds of African pear (Dacryodes edulis (G. Don) H.J. Lam) from Cameroon. Flavour Fragr. J. 20: 215-218.
Larkov, O., Zaks, A., Bar, E., Lewinsohn, E., Dudai, N., Mayer, A.M., Ravid, U. 2008. Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species. Phytochemistry 69: 2565-2571.
Lupien, S., Karp, F., Wildung, M., Croteau, R. 1999. Regiospecific cytochrome P450 limonene hydroxylases from mint (Mentha) species: cDNA isolation, characterization, and functional expression of (2)-4S-limonene-3-hydroxylase and (2)-4S-limonene-6-hydroxylase. Arch. Biochem. Biophys. 368: 181-192.
Maffei, M., Gallino, M., Sacco, T. 1986. Glandular trichomes and essential oils of developing leaves in Mentha viridis lavanduliodora.Planta Med. 52: 187-193.
Maffei, M., Chialva, F., Sacco, T. 1989. Glandular trichomes and essential oils in developing peppermint leaves. I. Variation of peltate trichome number and terpene distribution within leaves. New Phytol. 111: 707-716.
Maffei, M., Bertea, C.M., Mucciarelli, M. 2007. Anatomy, physiology, biosynthesis, molecular biology, tissue cultture, and biotechnology of mint essential oil production. In: Lawrence, B.M., ed. Mint, the genus Mentha. CRC Press Taylor & Francis Group, Boca Raton, Florida, pp. 42-46.
Malingre, T.M. 1971. Chemotaxonomisch onderzock von Mentha arvensisL. Pharm. Weekblad 106: 165-171.
McCaskill, D., Croteau, R. 1995. Monoterpene and sesquiterpene biosynthesis in glandular trichomes of peppermint (Mentha × piperita) rely exclusively on plastid-derived isopentenyl diphosphate. Planta 197: 49-56.
McCaskill, D.G., Gershenzon, J., Croteau, R. 1992. Morphology and monoterpene biosynthetic capabilities of secretory cell clusters isolated from glandular trichomes of peppermint (Mentha piperita L.). Planta 187: 445-454.
McConkey, M.E., Gershenzon, J., Croteau, R.B. 2000. Developmental regulation of monoterpene biosynthesis in the glandular trichomes of peppermint. Plant Physiol. 122: 215-223.
Merck. 1989. The Merck Index, 11th ed. Merck & Company, Inc. Rahway, NJ, p. 6243.
Murray, M.J., Lincoln, D.E. 1970. The genetic basis of acyclic oil constituents in Mentha citrata Ehrh. Genetics 65: 457-471.
Newman, J.D., Chappell, J. 1999. Isoprenoid biosynthesis in plants: carbon partitioning within the cytoplasmic pathway. Crit. Rev. Biochem. Mol. Biol. 34: 95-106.
Perez, A.G., Sanz, C., Olias, J.M. 1993. Partial purification and some properties of alcohol acetyltransferase from strawberry fruits. J. Agric. Food Chem. 41: 1462-1466.
Pichersky, E., Lewinsohn, E., Croteau, R. 1995. Purification and characterization of S-linalool synthase, an enzyme involved in the production of floral scent in Clarkia breweri.Arch. Biochem. Biophys. 316: 803-807.
Ponnamperuma, K., Croteau, R. 1996. Purification and characterization of an NADPH-cytochrome P450 (cytochrome c) reductase from spearmint (Mentha spicata) glandular trichomes. Arch. Biochem. Biophys. 329: 9-16.
Rohloff, J. 1999. Monoterpene composition of essential oil from peppermint (Mentha × piperita L.) with regard to leaf position using solid-phase microextraction and gas chromatography/mass spectrometry analysis. J. Agric. Food Chem. 47: 3782-3786.
Shalit, M., Katzir, N., Tadmor, Y., Larkov, O., Burger, Y., Schalechet, F., Lastochkin, E., Ravid, U., Amar, O., Edelstein, M., Lewinsohn, E. 2001. Acetyl CoA: alcohol acetyl transferase activity and aroma formation in ripening melon fruits. J. Agric. Food Chem. 49: 794-799.
Shalit, M., Guterman, I., Volpin, H., Bar, E., Tamari, T., Menda, N., Adam, Z., Zamir, D., Vainstein, A., Weiss, D., Pichersky, E., Lewinsohn, E. 2003. Volatile ester formation in roses. Identification of an acetyl coenzyme A: geraniol/citronellol acetyltransferase in developing rose petals. Plant Physiol. 131: 1868-1876.
Shanker, S., Ajayakumar, P.V., Sangwan, N.S., Kumar, S., Sangwan, R.S. 1999. Essential oil gland number and ultrastructure during Mentha arvensis leaf ontogeny. Biol. Plant. 42: 379-387.
Sitrit, Y., Ninio, R., Bar, E., Golan, E., Larkov, O., Ravid, U., Lewinsohn, E. 2004. S-Linalool synthase activity in the fruit of the columnar cactus koubo [Cereus peruvianus (L.) Miller]. Plant Sci. 167: 1257-1262.
Turner, G.W., Gershenzon, J., Nielson, E.E., Froehlich, J.E., Croteau, R. 1999. Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of oil gland secretory cells. Plant Physiol. 120: 879-886.
Turner, G.W., Gershenzon, J., Croteau, R.B. 2000. Distribution of peltate glandular trichomes on developing leaves of peppermint. Plant Physiol. 124: 655-663.
Ueda, Y., Fujishita, N., Chachin, K. 1997. Presence of alcohol acetyltransferase in melons (Cucumis melo L.). Postharvest Biol. Technol. 10: 121-126.
Werker, E. 1993. Function of essential oil-secreting glandular hairs in aromatic plants of the Lamiaceae, a review. Flavour Fragr. J. 8: 249-255.
All Time | Past Year | Past 30 Days | |
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The potential to produce and accumulate mono- and sesquiterpenes in lemon mint (Mentha aquatica var. citrata) glandular trichomes was evaluated. Volatiles were extracted using methyl-tert-butyl ether or solid phase micro extraction and determined by gas chromatography-mass spectrometry. The main components of the essential oil of lemon mint are the monoterpene alcohol linalool and its ester linalyl acetate. Sesquiterpenes, such as elemol, (E)-caryophyllene, and germacrene D, as well as the monoterpenes 1,8-cineole, β-myrcene, and β-(E)-ocimene, are also prominent. Most of the essential oil is localized in the glands, as leaves devoid of trichomes had very low essential oil levels. The quantities of all these components per leaf increased during leaf development until reaching the third whorl, and then the levels remained steady. Conversely, the essential oil content per gram fresh weight decreased with leaf development, but the decrease was not statistically significant at p = 0.05. Desalted cell-free extracts derived from isolated glandular trichomes were able to convert geranyl diphosphate into linalool. Lower amounts of geranyl diphosphate were also converted to other monoterpenes such as myrcene, α-pinene, β-pinene, limonene, β-(E)-ocimene, and nerol. Furthermore, the extracts were able to convert farnesyl diphosphate into the sesquiterpene (E)-caryophyllene and lesser amounts of other sesquiterpenes such as δ-cadinene, α-humulene, β-(E)-farnesene, and α-gurjunene. These cell-free extracts also efficiently catalyzed the formation of linalyl acetate from linalool and acetyl-coenzyme A. Our findings indicate that glandular trichomes of lemon mint, similar to other members of the Lamiaceae, contain unique enzymatic activities capable of the synthesis of mono- and sesquiterpene components of its essential oil.
All Time | Past Year | Past 30 Days | |
---|---|---|---|
Abstract Views | 468 | 167 | 21 |
Full Text Views | 23 | 3 | 0 |
PDF Views & Downloads | 45 | 11 | 0 |