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Published March 31, 2019 | Version v1
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Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and OMethyltransferase

Authors/Creators

  • 1. ∗ & Newe Yaar Research Center, Agricultural Research Organization, P. O. Box 1021, Ramat Yishay, 30095, Israel

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Yahyaa, Mosaab, Berim, Anna, Nawade, Bhagwat, Ibdah, Muhammad, Dudareva, Natalia, Ibdah, Mwafaq (2019): Biosynthesis of methyleugenol and methylisoeugenol in Daucus carota leaves: Characterization of eugenol/isoeugenol synthase and OMethyltransferase. Phytochemistry 159: 179-189, DOI: 10.1016/j.phytochem.2018.12.020, URL: http://dx.doi.org/10.1016/j.phytochem.2018.12.020

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LSID
urn:lsid:plazi.org:pub:FFAA9630144FFFCEFFCFFFBA41764967
URL
http://publication.plazi.org/id/FFAA9630144FFFCEFFCFFFBA41764967

Has part
Taxonomic treatment: http://treatment.plazi.org/id/0393EE48144DFFCCFFABF903428D4B9B (URL)
Figure: 10.5281/zenodo.10481709 (DOI)
Figure: 10.5281/zenodo.10481711 (DOI)
Figure: 10.5281/zenodo.10481713 (DOI)
Figure: 10.5281/zenodo.10481715 (DOI)
Figure: 10.5281/zenodo.10481717 (DOI)
Figure: 10.5281/zenodo.10481719 (DOI)
Figure: 10.5281/zenodo.10481721 (DOI)
Figure: 10.5281/zenodo.10481723 (DOI)
Figure: 10.5281/zenodo.10481725 (DOI)
Figure: 10.5281/zenodo.10481727 (DOI)

References

  • Ahmed, M., Amin, S., Islam, M., Takahashi, M., Okuyama, E., Hossain, C., 2000. Analgesic principle from Abutilon indicum. Pharmazie 55, 314-316.
  • Alasalvar, C., Grigor, J.M., Zhang, D., Quantick, P.C., Shahidi, F., 2001. Comparison of volatiles, phenolics, sugars, antioxidant vitamins, and sensory quality of different colored carrot varieties. J. Agric. Food Chem. 49, 1410-1416.
  • Anarat-Cappillino, G., Sattely, E.S., 2014. The chemical logic of plant natural product biosynthesis. Curr. Opin. Plant Biol. 19, 51-58.
  • Araguez, I., Hoffmann, T., Osorio, S., Rambla, J.L., Medina-Escobar, N., Granell, A., Botella, M.A., Schwab, W., Valpuesta, V., 2013. Eugenol production in achenes and receptacles of strawberry fruits is catalyzed by synthases exhibiting distinct kinetics. Plant Physiol. 163, 946-958.
  • Arscott, S.A., Simon, P.W., Tanumihardjo, S.A., 2010. Anthocyanins in purple-orange carrots (Daucus carota L.) do not influence the bioavailability of β -carotene in young women. J. Agric. Food Chem. 58, 2877-2881.
  • Atkinson, R.G., 2018. Phenylpropenes: occurrence, distribution, and biosynthesis in fruit. J. Agric. Food Chem. 66, 2259-2272.
  • 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.
  • Dexter, R., Qualley, A., Kish, C.M., Ma, C.J., Koeduka, T., Nagegowda, D.A., Dudareva, N., Pichersky, E., Clark, D., 2007. Characterization of a petunia acetyltransferase involved in the biosynthesis of the floral volatile isoeugenol. Plant J. 49, 265-275.
  • Fischer, R., Nitzan, N., Chaimovitsh, D., Rubin, B., Dudai, N., 2011. Variation in essential oil composition within individual leaves of sweet basil (Ocimum basilicum L.) is more affected by leaf position than by leaf age. J. Agric. Food Chem. 59, 4913-4922.
  • Fukuda, T., Okazaki, K., Shinano, T., 2013. Aroma characteristic and volatile profiling of carrot varieties and quantitative role of terpenoid compounds for carrot sensory attributes. J. Food Sci. 78, S1800-S1806.
  • Gang, D.R., Lavid, N., Zubieta, C., Chen, F., Beuerle, T., Lewinsohn, E., Noel, J.P., Pichersky, E., 2002. Characterization of phenylpropene O -methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O -methyltransferase family. Plant Cell 14, 505-519.
  • Gupta, A.K., Schauvinhold, I., Pichersky, E., Schiestl, F.P., 2014. Eugenol synthase genes in floral scent variation in Gymnadenia species. Funct. Integr. Genom. 14, 779-788.
  • Hehmann, M., Luka c in, R., Ekiert, H., Matern, U., 2004. Furanocoumarin biosynthesis in Ammi majus L. FEBS J. 271, 932-940.
  • Kammerer, D., Carle, R., Schieber, A., 2004. Characterization of phenolic acids in black carrots (Daucus carota ssp. sativus var. atrorubens Alef.) by high-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 18, 1331-1340.
  • Karapinar, M., 1990. Inhibitory effects of anethole and eugenol on the growth and toxin production of Aspergillus parasiticus. Int. J. Food Microbiol. 10, 193-199.
  • Katz-Downie, D.S., Valiejo-Roman, C.M., Terentieva, E.I., 1999. Towards Apiaceae subfamily Apioideae: additional information from nuclear ribosomal DNA ITS sequences. Plant Systemat. Evol. 216, 167-195.
  • Kim, S.-J., Vassao, D.G., Moinuddin, S.G., Bedgar, D.L., Davin, L.B., Lewis, N.G., 2014. Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli. Arch. Biochem. Biophys. 541, 37-46.
  • Kjeldsen, F., Christensen, L.P., Edelenbos, M., 2001. Quantitative analysis of aroma compounds in carrot (Daucus carota L.) cultivars by capillary gas chromatography using large-volume injection technique. J. Agric. Food Chem. 49, 4342-4348.
  • Koeduka, T., 2014. The phenylpropene synthase pathway and its applications in the engineering of volatile phenylpropanoids in plants. Plant Biotechnol. 31, 401-407.
  • Koeduka, T., Baiga, T.J., Noel, J.P., Pichersky, E., 2009. Biosynthesis of t -anethole in anise: characterization of t -anol/isoeugenol synthase and an O -methyltransferase specific for a C7-C8 propenyl side chain. Plant Physiol. 149, 384-394.
  • Koeduka, T., Fridman, E., Gang, D.R., Vassao, D.G., Jackson, B.L., Kish, C.M., Orlova, I., Spassova, S.M., Lewis, N.G., Noel, J.P., 2006. Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Proc. Natl. Acad. Sci. Unit. States Am. 103, 10128-10133.
  • Koeduka, T., Kajiyama, M., Furuta, T., Suzuki, H., Tsuge, T., Matsui, K., 2016. Characterization of an O -methyltransferase specific to guaiacol-type benzenoids from the flowers of loquat (Eriobotrya japonica). J. Biosci. Bioeng. 122, 679-684.
  • Koeduka, T., Louie, G.V., Orlova, I., Kish, C.M., Ibdah, M., Wilkerson, C.G., Bowman, M.E., Baiga, T.J., Noel, J.P., Dudareva, N., 2008. The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida represent two distinct protein lineages. Plant J. 54, 362-374.
  • Lee, E.J., Yoo, K.S., Patil, B.S., 2011. Total carotenoid, anthocyanin, and sugar contents in sliced or whole purple (cv. Betasweet) and orange carrots during 4-week cold storage. Hortic. Environ. Biote. 52, 402-407.
  • Lewinsohn, E., Schalechet, F., Wilkinson, J., Matsui, K., Tadmor, Y., Nam, K.-H., Amar, O., Lastochkin, E., Larkov, O., Ravid, U., 2001. Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits. Plant Physiol. 127, 1256-1265.
  • Louie, G.V., Baiga, T.J., Bowman, M.E., Koeduka, T., Taylor, J.H., Spassova, S.M., Pichersky, E., Noel, J.P., 2007. Structure and reaction mechanism of basil eugenol synthase. PLoS One 2, e993.
  • Mansour, E.-S.S., Maatooq, G.T., Khalil, A.T., Marwan, E.-S.M., Sallam, A.A., 2004. Essential oil of Daucus glaber forssk. Z. Naturforsch. 59, 373-378.
  • Mojab, F., Hamedi, A., Nickavar, B., Javidnia, K., 2008. Hydrodistilled volatile constituents of the leaves of Daucus carota L. subsp. sativus (Hoffman.) Arcang. (Apiaceae) from Iran. J. Ess. Oil Bear. Pl. 11, 271-277.
  • Moleyar, V., Narasimham, P., 1992. Antibacterial activity of essential oil components. Int. J. Food Microbiol. 16, 337-342.
  • Muhlemann, J.K., Woodworth, B.D., Morgan, J.A., Dudareva, N., 2014. The monolignol pathway contributes to the biosynthesis of volatile phenylpropenes in flowers. New Phytol. 204, 661-670.
  • Pichersky, E., Gershenzon, J., 2002. The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Curr. Opin. Plant Biol. 5, 237-243.
  • Pichersky, E., Noel, J.P., Dudareva, N., 2006. Biosynthesis of plant volatiles: nature's diversity and ingenuity. Science 311, 808-811.
  • Qualley, A.V., Dudareva, N., 2008. Aromatic Volatiles and Their Involvement in Plant Defense. Induced Plant Resistance to Herbivory. Springer, pp. 409-432.
  • Raguso, R.A., Light, D.M., Pickersky, E., 1996. Electroantennogram responses of Hyles lineata (Sphingidae: Lepidoptera) to volatile compounds from Clarkia breweri (Onagraceae) and other moth-pollinated flowers. J. Chem. Ecol. 22, 1735-1766.
  • Rocha, L., Fernandes, C.P., 2016. Chapter 22 - aniseed (Pimpinella anisum, Apiaceae) oils A2 - preedy, Victor R. Essential oils. In: Food Preservation, Flavor and Safety. Academic Press, San Diego, pp. 209-213.
  • Rossi, P.-G., Bao, L., Luciani, A., Panighi, J., Desjobert, J.-M., Costa, J., Casanova, J., Bolla, J.-M., Berti, L., 2007. (E)-Methylisoeugenol and elemicin: antibacterial components of Daucus carota L. essential oil against Campylobacter jejuni. J. Agric. Food Chem. 55, 7332-7336.
  • Schmittgen, T.D., Livak, K.J., 2008. Analyzing real-time PCR data by the comparative C T method. Nat. Protoc. 3, 1101.
  • Singh, P., Kalunke, R.M., Giri, A.P., 2015. Towards comprehension of complex chemical evolution and diversification of terpene and phenylpropanoid pathways in Ocimum species. RSC Adv. 5, 106886-106904.
  • Staniszewska, M., Kula, J., Wieczorkiewicz, M., Kusewicz, D., 2005. Essential oils of wild and cultivated carrots-the chemical composition and antimicrobial activity. J. Ess. Oil 17, 579-583.
  • Tan, K.H., Nishida, R., 2012. Methyl eugenol: its occurrence, distribution, and role in nature, especially in relation to insect behavior and pollination. J. Insect Sci. 12, 1-74.
  • Vassao, D.G., Gang, D.R., Koeduka, T., Jackson, B., Pichersky, E., Davin, L.B., Lewis, N.G., 2006. Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD (P) H-dependent reduction. Org. Biomol. Chem. 4, 2733-2744.
  • Vassao, D.G., Kim, K.-W., Davin, L.B., Lewis, N.G., 2010. Lignans (neolignans) and allyl/ propenyl phenols: biogenesis, structural biology, and biological/human health considerations. Comprehensive Natural Products Ii: Chemistry and Biology, Vol 1: Natural Products Structural Diversity-I: Secondary Metabolites: Organization and Biosynthesis. pp. 815-928.
  • Wang, G.-L., Huang, Y., Zhang, X.-Y., Xu, Z.-S., Wang, F., Xiong, A.-S., 2016. Transcriptome-based identification of genes revealed differential expression profiles and lignin accumulation during root development in cultivated and wild carrots. Plant Cell Rep. 35, 1743-1755.
  • Wang, J., Pichersky, E., 1998. Characterization of S-adenosyl-L- methionine:(Iso) eugenol O -methyltransferase involved in floral scent production in Clarkia breweri. Arch. Biochem. Biophys. 349, 153-160.
  • Xie, Z., Kapteyn, J., Gang, D.R., 2008. A systems biology investigation of the MEP/terpenoid and shikimate/phenylpropanoid pathways points to multiple levels of metabolic control in sweet basil glandular trichomes. Plant J. 54, 349-361.
  • Yahyaa, M., Ibdah, M., Marzouk, S., Ibdah, M., 2018. Profiling of the terpene metabolome in carrot fruits of wild (Daucus carota L. ssp. carota) accessions and characterization of a geraniol synthase. J. Agric. Food Chem. 66, 2378-2386.
  • Yahyaa, M., Matsuba, Y., Brandt, W., Doron-Faigenboim, A., Bar, E., McClain, A., Davidovich-Rikanati, R., Lewinsohn, E., Pichersky, E., Ibdah, M., 2015a. Identification, functional characterization, and evolution of terpene synthases from a basal dicot. Plant Physiol. 169, 1683-1697.
  • Yahyaa, M., Tholl, D., Cormier, G., Jensen, R., Simon, P.W., Ibdah, M., 2015b. Identification and characterization of terpene synthases potentially involved in the formation of volatile terpenes in carrot (Daucus carota L.) roots. J. Agric. Food Chem. 63, 4870-4878.
  • Yauk, Y.K., Chagne, D., Tomes, S., Matich, A.J., Wang, M.Y., Chen, X., Maddumage, R., Hunt, M.B., Rowan, D.D., Atkinson, R.G., 2015. The O -methyltransferase gene MdoOMT1 is required for biosynthesis of methylated phenylpropenes in ripe apple fruit. Plant J. 82, 937-950.
  • Yauk, Y.K., Souleyre, E.J.F., Matich, A.J., Chen, X.Y., Wang, M.Y., Plunkett, B., Dare, A.P., Espley, R.V., Tomes, S., Chagne, D., Atkinson, R.G., 2017. Alcohol acyl transferase 1 links two distinct volatile pathways that produce esters and phenylpropenes in apple fruit. Plant J. 91, 292-305.
  • Zvi, M.M.B., Shklarman, E., Masci, T., Kalev, H., Debener, T., Shafir, S., Ovadis, M., Vainstein, A., 2012. PAP1 transcription factor enhances production of phenylpropanoid and terpenoid scent compounds in rose flowers. New Phytol. 195, 335-345.