Biosynthesis of essential oils in aromatic plants: A review

References

• Öztekin, S.; Martinov, M. Medicinal and Aromatic Crops: Harvesting, Drying, and Processing; Haworth Food & Agricultural Products Press: Binghamtion, NY, 2007.
   Google Scholar
• Holopainen, J.K. Multiple functions of inducible plant volatiles. Trends Plant Sci. 2004, 9, 529–533.
   PubMed Web of Science ®Google Scholar
• Dudareva, N.; Negre, F.; Nagegowda, D.A.; Orlova, I. Plant volatiles: Recent advances and future perspectives. Crit. Rev. Plant Sci. 2006, 25, 417–440.
   Web of Science ®Google Scholar
• Wagner, K.H.; Elmadfa, I. Biological relevance of terpenoids. Overview focusing on mono, di- and tetraterpenes. Ann. Nutr. Metab. 2003, 47, 95–106.
   PubMed Web of Science ®Google Scholar
• Caissard, J.C.; Joly, C.; Bergougnoux, V.; Hugueney, P.; Mauriat, M.; Baudino, S. Secretion mechanisms of volatile organic compounds in specialized cells of aromatic plants. Recent Res. Dev. Cell Biol. 2004, 2, 1–15.
   Google Scholar
• Sangwan, N.S.; Farooqi, A.H.A.; Shabih, F.; Sangwan, R.S. Regulation of essential oil production in plants. Plant Growth Regul. 2001, 34, 3–21.
   Web of Science ®Google Scholar
• Berka-Zougali, B.; Ferhat, M.-A.; Hassani, A.; Chemat, F.; Allaf, K.S. Comparative study of essential oils extracted from Algerian Myrtus communis L. leaves using microwaves and hydrodistillation. Int. J. Mol. Sci. 2012, 13, 4673–4695.
   PubMed Web of Science ®Google Scholar
• Waseem, R.; Low, K.H. Advanced analytical techniques for the extraction and characterization of plant-derived essential oils by gas chromatography with mass spectrometry. J. Sep. Sci. 2014, 38, 483–501.
   Web of Science ®Google Scholar
• Adam, K.P.; Thiel, R.; Zapp, J. Incorporation of 1-[1-13C]deoxy-d-xylulose in chamomile sesquiterpenes. Arch. Biochem. Biophys. 1999, 369, 127–132.
   PubMed Web of Science ®Google Scholar
• Langenheim, J.H. Higher plant terpenoids: A phytocentric overview of their ecological roles. J. Chem. Ecol. 1994, 20, 1223–1280.
   PubMed Web of Science ®Google Scholar
• Breitmaier, E. Terpenes: Flavors, Fragrances, Pharmaca, Pheromones; John Wiley & Sons: New York, 2006.
   Google Scholar
• Dubey, V.S.; Bhalla, R.; Luthra, R. An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants. J. Biosci. 2003, 28, 637–646.
   PubMed Web of Science ®Google Scholar
• McGarvey, D.J.; Croteau, R. Terpenoid metabolism. Plant Cell 1995, 7, 1015–1026.
   PubMed Web of Science ®Google Scholar
• Page, J.E.; Hause, G.; Raschke, M.; Gao, W.; Schmidt, J.; Zenk, M.H.; Kutchan, T.M. Functional analysis of the final steps of the 1-deoxy-d-xylulose 5-phosphate (DXP) pathway to isoprenoids in plants using virus-induced gene silencing. Plant Physiol. 2004, 134, 1401–1413.
   PubMed Web of Science ®Google Scholar
• Newman, J.D.; Chappell, J. Isoprenoid biosynthesis in plants: Carbon partitioning within the cytoplasmic pathway. Crit. Rev. Biochem. Mol. Biol. 1999, 34, 95–106.
   PubMed Web of Science ®Google Scholar
• Liao, Z.H.; Chen, M.; Gong, Y.F.; Miao, Z.Q.; Sun, X.F.; Tang, K.X. Isoprenoid biosynthesis in plants: Pathways, genes, regulation and metabolic engineering. J. Biol. Sci. 2006, 6, 209–219.
   Google Scholar
• Nagegowda, D.A. Plant volatile terpenoid metabolism: Biosynthetic genes, transcriptional regulation and subcellular compartmentation. FEBS Lett. 2010, 584, 2965–2973.
   PubMed Web of Science ®Google Scholar
• Wallach, O. Zur Kenntniss der Terpene und ätherischen Oele. Justus Liebigs Ann. Chem. 1887, 238, 78–89.
   Google Scholar
• Croteau, R. The discovery of terpenes. Discov. Plant Biol. 1998, 1, 329–343.
   Google Scholar
• Ruzicka, L. The isoprene rule and the biogenesis of terpenic compounds. Experientia 1953, 9, 357–367.
   PubMedGoogle Scholar
• Rohmer, M.; Seemann, M.; Grosdemange-Billiard, C. Biosynthetic routes to the building blocks of isoprenoids. In Biopolymers Online; Wiley Online Library. Wiley: New York, 2005; p 49.
   Google Scholar
• Rohmer, M. Isoprenoids including carotenoids and steroids. In Comprehensive Natural Products Chemistry; Cane, D.E., Eds.; Pergamon Press: Oxford, UK, 1999; pp 45–67.
   Google Scholar
• Rohmer, M. Mevalonate-independent methylerythritol phosphate pathway for isoprenoid biosynthesis. Elucidation and distribution. Pure Appl. Chem. 2003, 75, 375–388.
   Web of Science ®Google Scholar
• Rohmer, M. The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants. Nat. Prod. Rep. 1999, 16, 565–574.
   PubMed Web of Science ®Google Scholar
• Schwarz, M., Arigoni, D. Ginkgolide Biosynthesis. In Comprehensive Natural Product Chemistry. Isoprenoids Including Carotenoids and Steroids, Vol. 2; Cane, D.E., Ed.; Pergamon: Oxford, UK, 1999; pp. 367–400.
   Google Scholar
• Lombard, J.; Moreira, D. Origins and early evolution of the mevalonate pathway of isoprenoid biosynthesis in the three domains of life. Mol. Biology Evol. 2011, 28, 87–99.
   PubMed Web of Science ®Google Scholar
• Lichtenthaler, H.K.; Schwender, J.; Disch, A.; Rohmer, M. Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett. 1997, 400, 271–274.
   PubMed Web of Science ®Google Scholar
• Pulido, P.; Perello, C.; Rodriguez-Concepcion, M. New insights into plant isoprenoid metabolism. Mol. Plant 2012, 5, 964–967.
   PubMed Web of Science ®Google Scholar
• Cheng, A.X.; Lou, Y.G.; Mao, Y.B.; Lu, S.; Wang, L.J.; Chen, X.Y. Plant terpenoids: Biosynthesis and ecological functions. J. Integr. Plant Biol. 2007, 49, 179–186.
   Web of Science ®Google Scholar
• Ajikumar, P.K.; Tyo, K.; Carlsen, S.; Mucha, O.; Phon, T.H.; Stephanopoulos, G. Terpenoids: Opportunities for biosynthesis of natural product drugs using engineered microorganisms. Mol. Pharm. 2008, 5, 167–190.
   PubMed Web of Science ®Google Scholar
• Lichtenthaler, H.K. The 1-deoxy-d-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu. Rev. Plant Biol. 1999, 50, 47–65.
   PubMed Web of Science ®Google Scholar
• Hemmerlin, A.; Hoeffler, J.F.; Meyer, O.; Tritsch, D.; Kagan, I.A.; Grosdemange-Billiard, C.; Rohmer, M.; Bach, T.J. Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells. J. Biol. Chem. 2003, 278, 26666–26676.
   PubMed Web of Science ®Google Scholar
• Laule, O.; Fürholz, A.; Chang, H.S.; Zhu, T.; Wang, X.; Heifetz, P.B.; Gruissem, W.; Lange, M. Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 6866–6871.
   PubMed Web of Science ®Google Scholar
• Dudareva, N.; Andersson, S.; Orlova, I.; Gatto, N.; Reichelt, M.; Rhodes, D.; Boland, W.; Gershenzon, J. The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 933–938.
   PubMed Web of Science ®Google Scholar
• MacSweeney, A.; Lange, R.; Fernandes, R.P.M.; Schulz, H.; Dale, G.E.; Douangamath, A.; Proteau, P.J.; Oefner, C. The crystal structure of E. coli 1-deoxy-d-xylulose-5-phosphate reductoisomerase in a ternary complex with the antimalarial compound fosmidomycin and NADPH reveals a tight-binding closed enzyme conformation. J. Mol. Biol. 2005, 345, 115–127.
   Google Scholar
• Chappell, J. Biochemistry and molecular biology of the isoprenoid biosynthetic pathway in plants. Annu. Rev. Plant Biol. 1995, 46, 521–547.
   Web of Science ®Google Scholar
• Vollack, K.U.; Bach, T.J. Cloning of a cDNA encoding cytosolic acetoacetyl-coenzyme A thiolase from radish by functional expression in Saccharomyces cerevisiae. Plant Physiol. 1996, 111, 1097–1107.
   PubMed Web of Science ®Google Scholar
• Ahumada, I.; Cairó, A.; Hemmerlin, A.; González, V.; Pateraki, I.; Bach, T.J.; Rodríguez-Concepción, M.; Campos, N.; Boronat, A. Characterisation of the gene family encoding acetoacetyl-CoA thiolase in Arabidopsis. Funct. Plant Biol. 2008, 35, 1100–1111.
   Web of Science ®Google Scholar
• Montamat, F.; Guilloton, M.; Karst, F.; Delrot, S. Isolation and characterization of a cDNA encoding Arabidopsis thaliana 3-hydroxy-3-methylglutaryl-coenzyme A synthase. Gene 1995, 167, 197–201.
   PubMed Web of Science ®Google Scholar
• Nagegowda, D.A.; Bach, T.J.; Chye, M.L. Brassica juncea 3-hydroxy-3-methylglutaryl (HMG)-CoA synthase 1: Expression and characterization of recombinant wild-type and mutant enzymes. Biochem. J. 2004, 383, 517–527.
   PubMed Web of Science ®Google Scholar
• Sirinupong, N.; Suwanmanee, P.; Doolittle, R.F.; Suvachitanont, W. Molecular cloning of a new cDNA and expression of 3-hydroxy-3-methylglutaryl-CoA synthase gene from Hevea brasiliensis. Planta 2005, 221, 502–512.
   PubMed Web of Science ®Google Scholar
• Rodwell, V.W.; Beach, M.J.; Bischoff, K.M.; Bochar, D.A.; Darnay, B.G.; Friesen, J.A.; Gill, J.F.; Hedl, M.; Jordan-Starck, T.; Kennelly, P.J. et al. 3-Hydroxy-3-methylglutaryl-CoA reductase. Methods Enzymol. 2000, 324, 259–280.
   PubMed Web of Science ®Google Scholar
• Lumbreras, V.; Campos, N.; Boronat, A. The use of an alternative promoter in the Arabidopsis thaliana HMG1 gene generates an mRNA that encodes a novel 3-hydroxy-3-methylglutaryl coenzyme A reductase isoform with an extended N-terminal region. Plant J. 1995, 8, 541–549.
   PubMed Web of Science ®Google Scholar
• Nagegowda, D.A.; Rhodes, D.; Dudareva, N. The role of the methyl-erythritol-phosphate (MEP) pathway in rhythmic emission of volatiles. In The Chloroplast; Rebeiz, C.A.; Benning, C.; Bohnert, H.J.; Daniell, H.; Hoober, J.K.; Lichtenthaler, H.K.; Portis, A.R.; Tripathy, B.C., Eds.; Springer: Netherlands, 2010; pp 139–154.
   Google Scholar
• McCaskill, D.; Croteau, R. Some caveats for bioengineering terpenoid metabolism in plants. Trends Biotechnol. 1998, 16, 349–355.
   Web of Science ®Google Scholar
• Lee, M.; Leustek, T. Identification of the gene encoding homoserine kinase from Arabidopsis thaliana and characterization of the recombinant enzyme derived from the gene. Arch. Biochem. Biophys. 1999, 372, 135–142.
   PubMed Web of Science ®Google Scholar
• Lluch, M.A.; Masferrer, A.; Arró, M.; Boronat, A.; Ferrer, A. Molecular cloning and expression analysis of the mevalonate kinase gene from Arabidopsis thaliana. Plant Mol. Biol. 2000, 42, 365–376.
   PubMed Web of Science ®Google Scholar
• Simkin, A.J.; Guirimand, G.; Papon, N.; Courdavault, V.; Thabet, I.; Ginis, O.; Bouzid, S.; Giglioli-Guivarc’h, N.; Clastre, M. Peroxisomal localisation of the final steps of the mevalonic acid pathway in planta. Planta 2011, 234, 903–914.
   PubMed Web of Science ®Google Scholar
• Cordier, H.; Karst, F.; Bergès, T. Heterologous expression in Saccharomyces cerevisiae of an Arabidopsis thaliana cDNA encoding mevalonate diphosphate decarboxylase. Plant Mol. Biol. 1999, 39, 953–967.
   PubMed Web of Science ®Google Scholar
• Heaps, N.A.; Poulter, C.D. Type-2 isopentenyl diphosphate isomerase: Evidence for a stepwise mechanism. J. Am. Chem. Soc. 2011, 133, 19017–19019.
   PubMed Web of Science ®Google Scholar
• Guirimand, G.; Guihur, A.; Phillips, M.A.; Oudin, A.; Glévarec, G.; Mahroug, S.; Melin, C.; Papon, N.; Clastre, M.; Giglioli-Guivarc’h, N. Triple subcellular targeting of isopentenyl diphosphate isomerases encoded by a single gene. Plant Signal. Behav. 2012, 7, 1–3.
   PubMedGoogle Scholar
• Lois, L.M.; Rodríguez‐Concepción, M.; Gallego, F.; Campos, N.; Boronat, A. Carotenoid biosynthesis during tomato fruit development: Regulatory role of 1-deoxy-d-xylulose 5-phosphate synthase. Plant J. 2000, 22, 503–513.
   PubMed Web of Science ®Google Scholar
• Bouvier, F.; d’Harlingue A.; Suire C.; Backhaus R.A.; Camara B. Dedicated roles of plastid transketolases during the early onset of isoprenoid biogenesis in pepper fruits. Plant Physiol. 1998, 117, 1423–1431.
   Google Scholar
• Souret, F.F.; Weathers, P.J.; Wobbe, K.K. The mevalonate-independent pathway is expressed in transformed roots of Artemisia annua and regulated by light and culture age. In Vitro Cell. Dev. Biol. Plant 2002, 38, 581–588.
   Web of Science ®Google Scholar
• Proteau, P.J. 1-Deoxy-d-xylulose 5-phosphate reductoisomerase: An overview. Bioorg. Chem. 2004, 32, 483–493.
   PubMed Web of Science ®Google Scholar
• Han, M.; Heppel, S.C.; Su, T.; Bogs, J.; Zu, Y.; An, Z.; Rausch, T. Enzyme inhibitor studies reveal complex control of methyl-d-erythritol 4-phosphate (MEP) pathway enzyme expression in Catharanthus roseus. PloS ONE 2013, 8, e62467.
   Google Scholar
• Lange, B.M.; Turner, G.W. Terpenoid biosynthesis in trichomes—Current status and future opportunities. Plant Biotechnol. J. 2013, 11, 2–22.
   PubMed Web of Science ®Google Scholar
• Carretero-Paulet, L.; Ahumada, I.; Cunillera, N.; Rodríguez-Concepción, M.; Ferrer, A.; Boronat, A.; Campos, N. Expression and molecular analysis of the Arabidopsis DXR gene encoding 1-deoxy-d-xylulose 5-phosphate reductoisomerase, the first committed enzyme of the 2-C-methyl-d-erythritol 4-phosphate pathway. Plant Physiol. 2002, 129, 1581–1591.
   PubMed Web of Science ®Google Scholar
• Bodill, T.; Conibear, A.C.; Blatch, G.L.; Lobb, K.A.; Kaye, P.T. Synthesis and evaluation of phosphonated N-heteroarylcarboxamides as DOXP-reductoisomerase (DXR) inhibitors. Bioorg. Med. Chem. 2011, 19, 1321–1327.
   PubMed Web of Science ®Google Scholar
• Richard, S.B.; Lillo, A.M.; Tetzlaff, C.N.; Bowman, M.E.; Noel, J.P.; Cane, D.E. Kinetic analysis of Escherichia coli 2-C-methyl-d-erythritol-4-phosphate cytidyltransferase, wild type and mutants, reveals roles of active site amino acids. Biochemistry 2004, 43, 12189–12197.
   PubMed Web of Science ®Google Scholar
• Tholl, D.; Lee, S. Terpene specialized metabolism in Arabidopsis thaliana. In The Arabidopsis Book; The American Society of Plant Biologists: Rockville, MD, 2011; p e0143.
   Google Scholar
• Lan, X. Molecular cloning and characterization of the gene encoding 2-C-methyl-d-erythritol 4-phosphate cytidyltransferase from hairy roots of Rauvolfia verticillata. Biologia 2013, 68, 91–98.
   Web of Science ®Google Scholar
• Miallau, L.; Alphey, M.S.; Kemp, L.E.; Leonard, G.A.; McSweeney, S.M.; Hecht, S.; Bacher, A.; Eisenreich, W.; Rohdich, F.; Hunter, W.N. Biosynthesis of isoprenoids: Crystal structure of 4-diphosphocytidyl-2C-methyl-d-erythritol kinase. Proc. Natl. Acad. Sci. U. S. A. 2003, 100, 9173–9178.
   PubMed Web of Science ®Google Scholar
• Rohdich, F.; Wungsintaweekul, J.; Lüttgen, H.; Fischer, M.; Eisenreich, W.; Schuhr, C.A.; Fellermeier, M.; Schramek, N.; Zenk, M.H.; Bacher, A. Biosynthesis of terpenoids: 4-Diphosphocytidyl-2-C-methyl-d-erythritol kinase from tomato. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 8251–8256.
   PubMed Web of Science ®Google Scholar
• Kim, S.M.; Kim, Y.B.; Kuzuyama, T.; Kim, S.U. Two copies of 4-(cytidine 5′-diphospho)-2-C-methyl-d-erythritol kinase (CMK) gene in Ginkgo biloba: molecular cloning and functional characterization. Planta 2008, 228, 941–950.
   PubMed Web of Science ®Google Scholar
• Gao, S.; Lin, J.; Liu X, Deng, Z.; Li, Y.; Sun, X.; Tang, K. Molecular cloning, characterization and functional analysis of a 2C-methyl-d-erythritol 2,4-cyclodiphosphate synthase gene from Ginkgo biloba. J. Biochem. Mol. Biol. 2006, 39, 502–510.
   PubMedGoogle Scholar
• Jin, H.; Gong, Y.; Guo, B.; Qiu, C.; Liu, D.; Miao, Z.; Sun, X.; Tang, K. Isolation and characterization of a 2C-methyl-d-erythritol 2,4-cyclodiphosphate synthase gene from Taxus media. Mol. Biol. 2006, 40, 914–921.
   Web of Science ®Google Scholar
• Seemann, M.; Wegner, P.; Schünemann, V.; Bui, B.T.S.; Wolff, M.; Marquet, A.; Trautwein, A.X.; Rohmer, M. Isoprenoid biosynthesis in chloroplasts via the methylerythritol phosphate pathway: The (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE) from Arabidopsis thaliana is a [4Fe–4S] protein. J. Biol. Inorg. Chem. 2005, 10, 131–137.
   PubMed Web of Science ®Google Scholar
• Querol, J.; Campos, N.; Imperial, S.; Boronat, A.; Rodríguez-Concepción, M. Functional analysis of the Arabidopsis thaliana GCPE protein involved in plastid isoprenoid biosynthesis. FEBS Lett. 2002, 514, 343–346.
   PubMed Web of Science ®Google Scholar
• Rodríguez-Concepción, M.; Querol, J.; Lois, L.M.; Imperial, S.; Boronat, A. Bioinformatic and molecular analysis of hydroxymethylbutenyl diphosphate synthase (GCPE) gene expression during carotenoid accumulation in ripening tomato fruit. Planta 2003, 217, 476–482.
   PubMed Web of Science ®Google Scholar
• Gräwert, T.; Kaiser, J.; Zepeck, F.; Laupitz, R.; Hecht, S.; Amslinger, S.; Schramek, N.; Schleicher, E.; Weber, S.; Haslbeck, M. IspH protein of Escherichia coli: Studies on iron-sulfur cluster implementation and catalysis. J. Am. Chem. Soc. 2004, 126, 12847–12855.
   PubMed Web of Science ®Google Scholar
• Cunningham, F.X.; Lafond, T.P.; Gantt, E. Evidence of a role for LytB in the nonmevalonate pathway of isoprenoid biosynthesis. J. Bacteriol. 2000, 182, 5841–5848.
   PubMed Web of Science ®Google Scholar
• Sun, Y.; Chen, M.; Tang, J.; Liu, W.; Yang, C.; Yang, Y.; Lan, X.; Hsieh, M.; Liao, Z. The 1-hydroxy-2-methyl-butenyl 4-diphosphate reductase gene from Taxus media: Cloning, characterization and functional identification. Afr. J. Biotechnol. 2009, 8, 4339–4346.
   Web of Science ®Google Scholar
• Wouters, J.; Oudjama, Y.; Ghosh, S.; Stalon, V.; Droogmans, L.; Oldfield, E. Structure and mechanism of action of isopentenylpyrophosphate-dimethylallylpyrophosphate isomerase. J. Am. Chem. Soc. 2003, 125, 3198–3199.
   PubMed Web of Science ®Google Scholar
• Durbecq, V.; Sainz, G.; Oudjama, Y.; Clantin, B.; Bompard-Gilles, C.; Tricot, C.; Caillet, J.; Stalon, V.; Droogmans, L.; Villeret, V. Crystal structure of isopentenyl diphosphate: Dimethylallyl diphosphate isomerase. EMBO J. 2001, 20, 1530–1537.
   PubMed Web of Science ®Google Scholar
• Hamano, Y.; Dairi, T.; Yamamoto, M.; Kawasaki, T.; Kaneda, K.; Kuzuyama, T.; Itoh, N.; Seto, H. Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid-antibiotic-producing Streptomyces strain. Biosci. Biotechnol. Biochem. 2001, 65, 1627–1635.
   PubMed Web of Science ®Google Scholar
• Guirimand, G.; Guihur, A.; Phillips, M.A.; Oudin, A.; Glévarec, G.; Melin, C.; Papon, N.; Clastre, M.; St-Pierre, B.; Rodríguez-Concepción, M. A single gene encodes isopentenyl diphosphate isomerase isoforms targeted to plastids, mitochondria and peroxisomes in Catharanthus roseus. Plant Mol. Biol. 2012, 79, 443–459.
   PubMed Web of Science ®Google Scholar
• Tritsch, D.; Hemmerlin, A.; Bach, T.J.; Rohmer, M. Plant isoprenoid biosynthesis via the MEP pathway: In vivo IPP/DMAPP ratio produced by E-4-hydroxy-3-methylbut-2-enyl diphosphate reductase in tobacco BY-2 cell cultures. FEBS Lett. 2010, 584, 129–134.
   PubMed Web of Science ®Google Scholar
• Cordoba, E.; Salmi, M.; León, P. Unravelling the regulatory mechanisms that modulate the MEP pathway in higher plants. J. Exp. Bot. 2009, 60, 2933–2943.
   PubMed Web of Science ®Google Scholar
• Vranová, E.; Coman, D.; Gruissem, W. Structure and dynamics of the isoprenoid pathway network. Mol. Plant 2012, 5, 318–333.
   PubMed Web of Science ®Google Scholar
• Arigoni, D.; Eisenreich, W.; Latzel, C.; Sagner, S.; Radykewicz, T.; Zenk, M.H.; Bacher, A. Dimethylallyl pyrophosphate is not the committed precursor of isopentenyl pyrophosphate during terpenoid biosynthesis from 1-deoxyxylulose in higher plants. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1309–1314.
   PubMed Web of Science ®Google Scholar
• Thiel, R.; Adam, K.P. Incorporation of [1-13C]1-deoxy-d-xylulose into isoprenoids of the liverwort Conocephalum conicum. Phytochemistry 2002, 59, 269–274.
   PubMed Web of Science ®Google Scholar
• Nabeta, K.; Kawae, T.; Kikuchi, T.; Saitoh, T.; Okuyama, H. Biosynthesis of chlorophyll a from 13C-labelled mevalonates and glycine in liverwort. Nonequivalent labelling of phytyl side chain. J. Chem. Soc. Chem. Commun. 1995, 1995, 2529–2530.
   Google Scholar
• Itoh, D.; Karunagoda, R.P.; Fushie, T.; Katoh, K.; Nabeta, K. Nonequivalent labeling of the phytyl side chain of chlorophyll a in callus of the hornwort Anthoceros punctatus. J. Nat. Prod. 2000, 63, 1090–1093.
   PubMed Web of Science ®Google Scholar
• Adam, K.P.; Thiel, R.; Zapp, J. Incorporation of 1-[1-13C]deoxy-d-xylulose in chamomile sesquiterpenes. Arch. Biochem. Biophys. 1999, 369, 127–132.
   PubMed Web of Science ®Google Scholar
• Bick, J.A.; Lange, B.M. Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: Unidirectional transport of intermediates across the chloroplast envelope membrane. Arch. Biochem. Biophys. 2003, 415, 146–154.
   PubMed Web of Science ®Google Scholar
• Flügge, U.I.; Gao, W. Transport of isoprenoid intermediates across chloroplast envelope membranes. Plant Biol. 2005, 7, 91–97.
   PubMed Web of Science ®Google Scholar
• Luthra, R.; Luthra, P.M.; Kumar, S. Redefined role of mevalonate-isoprenoid pathway in terpenoid biosynthesis in higher plants. Curr. Sci. 1999, 76, 133–135.
   Web of Science ®Google Scholar
• Mahmoud, S.S.; Croteau, R.B. Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase. Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 8915–8920.
   PubMed Web of Science ®Google Scholar
• Sacchettini, J.C.; Poulter, C.D. Creating isoprenoid diversity. Science 1997, 277, 1788–1789.
   PubMed Web of Science ®Google Scholar
• Phillips, D.R.; Rasbery, J.M.; Bartel, B.; Matsuda, S. Biosynthetic diversity in plant triterpene cyclization. Curr. Opin. Plant Biol. 2006, 9, 305–314.
   PubMed Web of Science ®Google Scholar
• Trapp, S.C.; Croteau, R.B. Genomic organization of plant terpene synthases and molecular evolutionary implications. Genetics 2001, 158, 811–832.
   PubMed Web of Science ®Google Scholar
• Ohnuma, Si.; Hirooka, K.; Tsuruoka, N.; Yano, M.; Ohto, C.; Nakane, H.; Nishino, T. A pathway where polyprenyl diphosphate elongates in prenyltransferase: Insight into a common mechanism of chain length determination of prenyltransferases. J. Biol. Chem. 1998, 273, 26705–26713.
   PubMed Web of Science ®Google Scholar
• Wang, K.C.; Ohnuma, S.I. Isoprenyl diphosphate synthases. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 2000, 1529, 33–48.
   PubMed Web of Science ®Google Scholar
• Lesburg, C.A.; Caruthers, J.M.; Paschall, C.M.; Christianson, D.W. Managing and manipulating carbocations in biology: Terpenoid cyclase structure and mechanism. Curr. Opin. Struct. Biol. 1998, 8, 695–703.
   PubMed Web of Science ®Google Scholar
• Kellogg, B.A.; Poulter, C.D. Chain elongation in the isoprenoid biosynthetic pathway. Curr. Opin. Chem. Biol. 1997, 1, 570–578.
   PubMed Web of Science ®Google Scholar
• Sallaud, C.; Rontein, D.; Onillon, S.; Jabès, F.; Duffé, P.; Giacalone, C.; Thoraval, S.; Escoffier, C.; Herbette, G.; Leonhardt, N. A novel pathway for sesquiterpene biosynthesis from Z, Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites. Plant Cell Online 2009, 21, 301–317.
   PubMed Web of Science ®Google Scholar
• Hsiao, Y.Y.; Jeng, M.F.; Tsai, W.C.; Chuang, Y.C.; Li, C.Y.; Wu, T.S.; Kuoh, C.S.; Chen, W.H.; Chen, H.H. A novel homodimeric geranyl diphosphate synthase from the orchid Phalaenopsis bellina lacking a DD(X)2–4D motif. Plant J. 2008, 55, 719–733.
   PubMed Web of Science ®Google Scholar
• Schmidt, A.; Wächtler, B.; Temp, U.; Krekling, T.; Séguin, A.; Gershenzon, J. A bifunctional geranyl and geranylgeranyl diphosphate synthase is involved in terpene oleoresin formation in Picea abies. Plant Physiol. 2010, 152, 639–655.
   PubMed Web of Science ®Google Scholar
• Burke, C.C.; Wildung, M.R.; Croteau, R. Geranyl diphosphate synthase: Cloning, expression, and characterization of this prenyltransferase as a heterodimer. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 13062–13067.
   PubMed Web of Science ®Google Scholar
• Tholl, D.; Kish, C.M.; Orlova, I.; Sherman, D.; Gershenzon, J.; Pichersky, E.; Dudareva, N. Formation of monoterpenes in Antirrhinum majus and Clarkia breweri flowers involves heterodimeric geranyl diphosphate synthases. Plant Cell Online 2004, 16, 977–992.
   PubMed Web of Science ®Google Scholar
• Wang, G.; Dixon, R.A. Heterodimeric geranyl(geranyl)diphosphate synthase from hop (Humulus lupulus) and the evolution of monoterpene biosynthesis. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 9914–9919.
   PubMed Web of Science ®Google Scholar
• Wu, S.; Schalk, M.; Clark, A.; Miles, R.B.; Coates, R.; Chappell, J. Redirection of cytosolic or plastidic isoprenoid precursors elevates terpene production in plants. Nat. Biotechnol. 2006, 24, 1441–1447.
   PubMed Web of Science ®Google Scholar
• Gaffe, J.; Bru, J.P.; Causse, M.; Vidal, A.; Stamitti-Bert, L.; Carde, J.P.; Gallusci, P. LEFPS1, a tomato farnesyl pyrophosphate gene highly expressed during early fruit development. Plant Physiol. 2000, 123, 1351–1362.
   PubMed Web of Science ®Google Scholar
• Hemmerlin, A.; Rivera, S.B.; Erickson, H.K.; Poulter, C.D. Enzymes encoded by the farnesyl diphosphate synthase gene family in the big sagebrush Artemisia tridentata ssp. spiciformis. J. Biol. Chem. 2003, 278, 32132–32140.
   PubMed Web of Science ®Google Scholar
• Cunillera, N.; Arro, M.; Delourme, D.; Karst, F.; Boronat, A.; Ferrer, A. Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes. J. Biol. Chem. 1996, 271, 7774–7780.
   PubMed Web of Science ®Google Scholar
• Hong, Y.J.; Irmisch, S.; Wang, S.C.; Garms, S.; Gershenzon, J.; Zu, L.; Köllner, T.G.; Tantillo, D.J. Theoretical and experimental analysis of the reaction mechanism of MrTPS2, a triquinane-forming sesquiterpene synthase from chamomile. Chem. Eur. J. 2013, 19, 13590–13600.
   PubMed Web of Science ®Google Scholar
• Osbourn, A.E.; Lanzotti, V. Plant-Derived Natural Products; Springer: New York; 2009.
   Google Scholar
• Degenhardt, J.; Köllner, T.G.; Gershenzon, J. Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 2009, 70, 1621–1637.
   PubMed Web of Science ®Google Scholar
• Kampranis, S.C.; Ioannidis, D.; Purvis, A.; Mahrez, W.; Ninga, E.; Katerelos, N.A.; Anssour, S.; Dunwell, J.M.; Degenhardt, J.; Makris, A.M. Rational conversion of substrate and product specificity in a Salvia monoterpene synthase: Structural insights into the evolution of terpene synthase function. Plant Cell Online 2007, 19, 1994–2005.
   PubMed Web of Science ®Google Scholar
• Nagegowda, D.A.; Dudareva, N. Plant biochemistry and biotechnology of flavor compounds and essential oils. In Medicinal Plant Biotechnology; Kayser, O.; Quax, W.J., Eds.; GmbH & Co. KGaA: Weinheim, Germany, 2008; pp 469–492.
   Google Scholar
• Chen, F.; Tholl, D.; Bohlmann, J.; Pichersky, E. The family of terpene synthases in plants: A mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom. Plant J. 2011, 66, 212–229.
   PubMed Web of Science ®Google Scholar
• Bohlmann, J.; Phillips, M.; Ramachandiran, V.; Katoh, S.; Croteau, R. cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis). Arch. Biochem. Biophys. 1999, 368, 232–243.
   PubMed Web of Science ®Google Scholar
• Maruyama, T.; Saeki, D.; Ito, M.; Honda, G. Molecular cloning, functional expression and characterization of d-limonene synthase from Agastache rugosa. Biol. Pharm. Bull. 2002, 25, 661–665.
   PubMed Web of Science ®Google Scholar
• Dudareva, N.; Martin, D.; Kish, C.M.; Kolosova, N.; Gorenstein, N.; Fäldt, J.; Miller, B.; Bohlmann, J. (E)-β-ocimene and myrcene synthase genes of floral scent biosynthesis in snapdragon: Function and expression of three terpene synthase genes of a new terpene synthase subfamily. Plant Cell Online 2003, 15, 1227–1241.
   PubMed Web of Science ®Google Scholar
• Nagegowda, D.A.; Gutensohn, M.; Wilkerson, C.G.; Dudareva, N. Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers. Plant J. 2008, 55, 224–239.
   PubMed Web of Science ®Google Scholar
• Chen, F.; Tholl, D.; D’Auria, J.C.; Farooq, A.; Pichersky, E.; Gershenzon, J. Biosynthesis and emission of terpenoid volatiles from Arabidopsis flowers. Plant Cell Online 2003, 15, 481–494.
   PubMed Web of Science ®Google Scholar
• Fäldt, J.; Arimura, G-I.; Gershenzon, J.; Takabayashi, J.; Bohlmann, J. Functional identification of AtTPS03 as (E)-β-ocimene synthase: A monoterpene synthase catalyzing jasmonate- and wound-induced volatile formation in Arabidopsis thaliana. Planta 2003, 216, 745–751.
   PubMed Web of Science ®Google Scholar
• Bohlmann, J.; Martin, D.; Oldham, N.J.; Gershenzon, J. Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-β-ocimene synthase. Arch. Biochem. Biophys. 2000, 375, 261–269.
   PubMed Web of Science ®Google Scholar
• Chen, F.; Ro, D.-K.; Petri, J.; Gershenzon, J.; Bohlmann, J.; Pichersky, E.; Tholl, D. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Plant Physiol. 2004, 135, 1956–1966.
   PubMed Web of Science ®Google Scholar
• Jia, J.-W.; Crock, J.; Lu, S.; Croteau, R.; Chen, X.-Y. (3R)-Linalool synthase from Artemisia annua L.: cDNA isolation, characterization, and wound induction. Arch. Biochem. Biophys. 1999, 372, 143–149.
   PubMed Web of Science ®Google Scholar
• Lu, S.; Xu, R.; Jia, J.-W.; Pang, J.; Matsuda, S.P.; Chen, X.-Y. Cloning and functional characterization of a β-pinene synthase from Artemisia annua that shows a circadian pattern of expression. Plant Physiol. 2002, 130, 477–486.
   PubMed Web of Science ®Google Scholar
• Guennewich, N.; Page, JE.; Köllner, TG.; Degenhardt, J.; Kutchan, TM. Functional expression and characterization of trichome-specific (−)-limonene synthase and (+)-α-pinene synthase from Cannabis sativa. Nat. Prod. Commun. 2007, 2, 223–232.
   Web of Science ®Google Scholar
• Zeng, Y.; Yang, T. RNA isolation from highly viscous samples rich in polyphenols and polysaccharides. Plant Mol. Biol. Report. 2002, 20, 417–417.
   Google Scholar
• Lücker, J.; El Tamer, M.K.; Schwab, W.; Verstappen, F.W.; van der Plas, L.H.; Bouwmeester, H.J.; Verhoeven, H.A. Monoterpene biosynthesis in lemon (Citrus limon). Eur. J. Biochem. 2002, 269, 3160–3171.
   PubMedGoogle Scholar
• Shimada, T.; Endo, T.; Fujii, H.; Hara, M.; Omura, M. Isolation and characterization of (E)-beta-ocimene and 1,8-cineole synthases in Citrus unshiu Marc. Plant Sci. 2005, 168, 987–995.
   Web of Science ®Google Scholar
• Shimada, T.; Endo, T.; Fujii, H.; Omura, M. Isolation and characterization of a new d-limonene synthase gene with a different expression pattern in Citrus unshiu Marc. Sci. Hortic. 2005, 105, 507–512.
   Web of Science ®Google Scholar
• Shimada, T.; Endo, T.; Fujii, H.; Hara, M.; Ueda, T.; Kita, M.; Omura, M. Molecular cloning and functional characterization of four monoterpene synthase genes from Citrus unshiu Marc. Plant Sci. 2004, 166, 49–58.
   Web of Science ®Google Scholar
• Aharoni, A.; Giri, A.P.; Verstappen, F.W.; Bertea, C.M.; Sevenier, R.; Sun, Z.; Jongsma, M.A.; Schwab, W.; Bouwmeester, H.J. Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell Online 2004, 16, 3110–3131.
   PubMed Web of Science ®Google Scholar
• Landmann, C.; Fink, B.; Festner, M.; Dregus, M.; Engel, K.-H.; Schwab, W. Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia). Arch. Biochem. Biophys. 2007, 465, 417–429.
   PubMed Web of Science ®Google Scholar
• Arimura, G-I.; Ozawa, R.; Kugimiya, S.; Takabayashi, J.; Bohlmann, J. Herbivore-induced defense response in a model legume. Two-spotted spider mites induce emission of (E)-β-ocimene and transcript accumulation of (E)-β-ocimene synthase in Lotus japonicus. Plant Physiol. 2004, 135, 1976–1983.
   Google Scholar
• van Schie, C.C.; Haring, M.A.; Schuurink, R.C. Tomato linalool synthase is induced in trichomes by jasmonic acid. Plant Mol. Biol. 2007, 64, 251–263.
   PubMed Web of Science ®Google Scholar
• Demissie, Z.A.; Erland, L.A.; Rheault, M.R.; Mahmoud, S.S. The Biosynthetic origin of irregular monoterpenes in Lavandula isolation and biochemical characterization of a novel cis-prenyl diphosphate synthase gene, lavandulyl diphosphate synthase. J. Biol. Chem. 2013, 288, 6333–6341.
   PubMed Web of Science ®Google Scholar
• Lee, S.; Chappell, J. Biochemical and genomic characterization of terpene synthases in Magnolia grandiflora. Plant Physiol. 2008, 147, 1017–1033.
   PubMed Web of Science ®Google Scholar
• Irmisch, S.; Krause, S.T.; Kunert, G.; Gershenzon, J.; Degenhardt, J.; Köllner, T.G. The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils. BMC Plant Biol. 2012, 12, 84.
   PubMed Web of Science ®Google Scholar
• Shelton, D.; Zabaras, D.; Chohan, S.; Wyllie, S.G.; Baverstock, P.; Leach, D.; Henry, R. Isolation and partial characterisation of a putative monoterpene synthase from Melaleuca alternifolia. Plant Physiol. Biochem. 2004, 42, 875–882.
   PubMed Web of Science ®Google Scholar
• Crowell, A.L.; Williams, D.C.; Davis, E.M.; Wildung, M.R.; Croteau, R. Molecular cloning and characterization of a new linalool synthase. Arch. Biochem. Biophys. 2002, 405, 112–121.
   PubMed Web of Science ®Google Scholar
• Roeder, S.; Hartmann, A.-M.; Effmert, U.; Piechulla, B. Regulation of simultaneous synthesis of floral scent terpenoids by the 1,8-cineole synthase of Nicotiana suaveolens. Plant Mol. Biology 2007, 65, 107–124.
   PubMed Web of Science ®Google Scholar
• Iijima, Y.; Gang, D.R.; Fridman, E.; Lewinsohn, E.; Pichersky, E. Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiol. 2004, 134, 370–379.
   PubMed Web of Science ®Google Scholar
• Iijima, Y.; Davidovich-Rikanati, R.; Fridman, E.; Gang, D.R.; Bar, E.; Lewinsohn, E.; Pichersky, E. The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil. Plant Physiol. 2004, 136, 3724–3736.
   PubMed Web of Science ®Google Scholar
• Yuan, J.S.; Köllner, T.G.; Wiggins, G.; Grant, J.; Degenhardt, J.; Chen, F. Molecular and genomic basis of volatile-mediated indirect defense against insects in rice. Plant J. 2008, 55, 491–503.
   PubMed Web of Science ®Google Scholar
• Ito, M.; Honda, G. Geraniol synthases from perilla and their taxonomical significance. Phytochemistry 2007, 68, 446–453.
   PubMed Web of Science ®Google Scholar
• Ito, M.; Kiuchi, F.; Yang, L.L.; Honda, G. Perilla citriodora from Taiwan and its phytochemical characteristics. Biol. Pharm. Bull. 2000, 23, 359–362.
   PubMed Web of Science ®Google Scholar
• Hosoi, M.; Ito, M.; Yagura, T.; Adams, R.P.; Honda, G. cDNA isolation and functional expression of myrcene synthase from Perilla frutescens. Biol. Pharm. Bull. 2004, 27, 1979–1985.
   PubMed Web of Science ®Google Scholar
• Arimura, G.-I.; Köpke, S.; Kunert, M.; Volpe, V.; David, A.; Brand, P.; Dabrowska, P.; Maffei, M.E.; Boland, W. Effects of feeding Spodoptera littoralis on lima bean leaves: IV. Diurnal and nocturnal damage differentially initiate plant volatile emission. Plant Physiol. 2008, 146, 965–973.
   PubMed Web of Science ®Google Scholar
• Fäldt, J.; Martin, D.; Miller, B.; Rawat, S.; Bohlmann, J. Traumatic resin defense in Norway spruce (Picea abies): Methyl jasmonate-induced terpene synthase gene expression, and cDNA cloning and functional characterization of (+)-3-carene synthase. Plant Mol. Biol. 2003, 51, 119–133.
   PubMed Web of Science ®Google Scholar
• Martin, D.M.; Fäldt, J.; Bohlmann, J. Functional characterization of nine Norway spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily. Plant Physiol. 2004, 135, 1908–1927.
   PubMed Web of Science ®Google Scholar
• McKay, S.A.B.; Hunter, W.L.; Godard, K.-A.; Wang, S.X.; Martin, D.M.; Bohlmann, J.; Plant, A.L. Insect attack and wounding induce traumatic resin duct development and gene expression of (−)-pinene synthase in Sitka spruce. Plant Physiol. 2003, 133, 368–378.
   PubMed Web of Science ®Google Scholar
• Byun-McKay, A.; Godard, K.-A.; Toudefallah, M.; Martin, D.M.; Alfaro, R.; King, J.; Bohlmann, J.; Plant, A.L. Wound-induced terpene synthase gene expression in Sitka spruce that exhibit resistance or susceptibility to attack by the white pine weevil. Plant Physiol. 2006, 140, 1009–1021.
   PubMed Web of Science ®Google Scholar
• Phillips, M.A.; Wildung, M.R.; Williams, D.C.; Hyatt, D.C.; Croteau, R. cDNA isolation, functional expression, and characterization of (+)-α-pinene synthase and (−)-α-pinene synthase from loblolly pine (Pinus taeda): Stereocontrol in pinene biosynthesis. Arch. Biochem. Biophys. 2003, 411, 267–276.
   PubMed Web of Science ®Google Scholar
• Zapata, F.; Fine, P.V. Diversification of the monoterpene synthase gene family (TPSb) in Protium, a highly diverse genus of tropical trees. Mol. Phylogenet. Evol. 2013, 68, 432–442.
   PubMed Web of Science ®Google Scholar
• Huber, D.P.; Philippe, R.N.; Godard, K.-A.; Sturrock, R.N.; Bohlmann, J. Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii. Phytochemistry 2005, 66, 1427–1439.
   PubMed Web of Science ®Google Scholar
• Fischbach, R.J.; Zimmer, W.; Schnitzler, J.P. Isolation and functional analysis of a cDNA encoding a myrcene synthase from holm oak (Quercus ilex L.). Eur. J. Biochem. 2001, 268, 5633–5638.
   PubMedGoogle Scholar
• Kampranis, S.C.; Ioannidis, D.; Purvis, A.; Mahrez, W.; Ninga, E.; Katerelos, N.A.; Anssour, S.; Dunwell, J.M.; Degenhardt, J.; Makris, A.M., et al. Rational conversion of substrate and product specificity in a Salvia monoterpene synthase: Structural insights into the evolution of terpene synthase function. Plant Cell Online 2007, 19, 1994–2005.
   PubMed Web of Science ®Google Scholar
• Hoelscher, D.J.; Williams, D.C.; Wildung, M.R.; Croteau, R. A cDNA clone for 3-carene synthase from Salvia stenophylla. Phytochemistry 2003, 62, 1081–1086.
   PubMed Web of Science ®Google Scholar
• Jones, C.G.; Keeling, C.I.; Ghisalberti, E.L.; Barbour, E.L.; Plummer, J.A.; Bohlmann, J. Isolation of cDNAs and functional characterisation of two multi-product terpene synthase enzymes from sandalwood, Santalum album L. Arch. Biochem. Biophys. 2008, 477, 121–130.
   PubMed Web of Science ®Google Scholar
• Maruyama, T.; Ito, M.; Kiuchi, F.; Honda, G. Molecular cloning, functional expression and characterization of d-limonene synthase from Schizonepeta tenuifolia. Biol. Pharm. Bull. 2001, 24, 373–377.
   PubMed Web of Science ®Google Scholar
• Schilmiller, A.L.; Schauvinhold, I.; Larson, M.; Xu, R.; Charbonneau, A.L.; Schmidt, A.; Wilkerson, C.; Last, R.L.; Pichersky, E. Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 10865–10870.
   PubMed Web of Science ®Google Scholar
• Martin, D.M.; Bohlmann, J. Identification of Vitis vinifera (−)-α-terpineol synthase by in silico screening of full-length cDNA ESTs and functional characterization of recombinant terpene synthase. Phytochemistry 2004, 65, 1223–1229.
   PubMed Web of Science ®Google Scholar
• Fu, H.; Dooner, H.K. Intraspecific violation of genetic colinearity and its implications in maize. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 9573–9578.
   PubMed Web of Science ®Google Scholar
• Lin, C.; Shen, B.; Xu, Z.; Köllner, T.G.; Degenhardt, J.; Dooner, H.K. Characterization of the monoterpene synthase gene tps26, the ortholog of a gene induced by insect herbivory in maize. Plant Physiol. 2008, 146, 940–951.
   PubMed Web of Science ®Google Scholar
• Wu, S.; Schoenbeck, M.A.; Greenhagen, B.T.; Takahashi, S.; Lee, S.; Coates, R.M.; Chappell, J. Surrogate splicing for functional analysis of sesquiterpene synthase genes. Plant Physiol. 2005, 138, 1322–1333.
   PubMed Web of Science ®Google Scholar
• Mayer, K.; Schuller, C.; Wambutt, R.; Murphy, G.; Volckaert, G.; Pohl, T.; Dusterhoft, A.; Stiekema, W.; Entian, K.D.; Terryn, N., et al. Sequence and analysis of chromosome 4 of the plant Arabidopsis thaliana. Nature 1999, 402, 769–777.
   PubMed Web of Science ®Google Scholar
• Cai, Y.; Jia, J.-W.; Crock, J.; Lin, Z.-X.; Chen, X.-Y. Croteau, R. A cDNA clone for β-caryophyllene synthase from Artemisia annua. Phytochemistry 2002, 61, 523–529.
   PubMed Web of Science ®Google Scholar
• Chang, Y.-J.; Song, S.-H.; Park, S.-H.; Kim, S.-U. Amorpha-4,11-diene synthase of Artemisia annua: cDNA isolation and bacterial expression of a terpene synthase involved in artemisinin biosynthesis. Arch. Biochem. Biophys. 2000, 383, 178–184.
   PubMed Web of Science ®Google Scholar
• Mercke, P.; Bengtsson, M.; Bouwmeester, H.J.; Posthumus, M.A.; Brodelius, P.E. Molecular cloning, expression, and characterization of amorpha-4,11-diene synthase, a key enzyme of artemisinin biosynthesis in Artemisia annua L. Arch. Biochem. Biophys. 2000, 381, 173–180.
   PubMed Web of Science ®Google Scholar
• Wallaart, T.E.; Bouwmeester, H.J.; Hille, J.; Poppinga, L.; Maijers, N.C. Amorpha-4,11-diene synthase: Cloning and functional expression of a key enzyme in the biosynthetic pathway of the novel antimalarial drug artemisinin. Planta 2001, 212, 460–465.
   PubMed Web of Science ®Google Scholar
• Van Geldre, E.; De Pauw, I.; Inzé, D.; Van Montagu, M., Van den Eeckhout, E. Cloning and molecular analysis of two new sesquiterpene cyclases from Artemisia annua L. Plant Sci. 2000, 158, 163–171.
   PubMed Web of Science ®Google Scholar
• Hua, L.; Matsuda, S.P. The molecular cloning of 8-epicedrol synthase from Artemisia annua. Arch. Biochem. Biophys. 1999, 369, 208–212.
   PubMed Web of Science ®Google Scholar
• Mercke, P.; Crock, J.; Croteau, R.; Brodelius, P.E. Cloning, expression, and characterization of epi-cedrol synthase, a sesquiterpene cyclase from Artemisia annua L. Arch. Biochem. Biophys. 1999, 369, 213–222.
   PubMed Web of Science ®Google Scholar
• Picaud, S.; Brodelius, M.; Brodelius, P.E. Expression, purification and characterization of recombinant (E)-β-farnesene synthase from Artemisia annua. Phytochemistry 2005, 66, 961–967.
   PubMed Web of Science ®Google Scholar
• Bertea, C.M.; Voster, A.; Verstappen, F.W.; Maffei, M.; Beekwilder, J.; Bouwmeester, H.J. Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch. Biochem. Biophys. 2006, 448, 3–12.
   PubMed Web of Science ®Google Scholar
• Bouwmeester, H.J.; Kodde, J.; Verstappen, F.W.; Altug, I.G.; de Kraker, J.-W.; Wallaart, T.E. Isolation and characterization of two germacrene A synthase cDNA clones from chicory. Plant Physiol. 2002, 129, 134–144.
   PubMed Web of Science ®Google Scholar
• Maruyama, T.; Ito, M.; Honda, G. Molecular cloning, functional expression and characterization of (E)-beta-farnesene synthase from Citrus junos. Biol. Pharm. Bull. 2001, 24, 1171–1175.
   PubMed Web of Science ®Google Scholar
• Sharon-Asa, L.; Shalit, M.; Frydman, A.; Bar, E.; Holland, D.; Or, E.; Lavi, U.; Lewinsohn, E.; Eyal, Y. Citrus fruit flavor and aroma biosynthesis: Isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene. Plant J. 2003, 36, 664–674.
   PubMed Web of Science ®Google Scholar
• Portnoy, V.; Benyamini, Y.; Bar, E.; Harel-Beja, R.; Gepstein, S.; Giovannoni, J.J.; Schaffer, A.A.; Burger, J.; Tadmor, Y.; Lewinsohn, E.; Katzir, N. The molecular and biochemical basis for varietal variation in sesquiterpene content in melon (Cucumis melo L.) rinds. Plant Mol. Biol. 2008, 66, 647–661.
   PubMed Web of Science ®Google Scholar
• Mercke, P.; Kappers, I.F.; Verstappen, F.W.; Vorst, O.; Dicke, M.; Bouwmeester, H.J. Combined transcript and metabolite analysis reveals genes involved in spider mite induced volatile formation in cucumber plants. Plant Physiol. 2004, 135, 2012–2024.
   PubMed Web of Science ®Google Scholar
• Shah, F.H.; Cha, T. A mesocarp- and species-specific cDNA clone from oil palm encodes for sesquiterpene synthase. Plant Sci. 2000, 154, 153–160.
   PubMed Web of Science ®Google Scholar
• Tan, X.-P.; Liang, W.-Q.; Liu, C.-J.; Luo, P.; Heinstein, P.; Chen, X.-Y. Expression pattern of (+)-δ-cadinene synthase genes and biosynthesis of sesquiterpene aldehydes in plants of Gossypium arboreum L. Planta 2000, 210, 644–651.
   PubMed Web of Science ®Google Scholar
• Townsend, B.J.; Poole, A.; Blake, C.J.; Llewellyn, D.J. Antisense suppression of a (+)-δ-cadinene synthase gene in cotton prevents the induction of this defense response gene during bacterial blight infection but not its constitutive expression. Plant Physiol. 2005, 138, 516–528.
   PubMed Web of Science ®Google Scholar
• Meng, Y.-L.; Jia, J.-W.; Liu, C.-J.; Liang, W.-Q.; Heinstein, P.; Chen, X.-Y. Coordinated accumulation of (+)-δ-cadinene synthase mRNAs and gossypol in developing seeds of Gossypium hirsutum and a new member of the cad 1 family from G. arboreum. J. Nat. Prod. 1999, 62, 248–252.
   PubMed Web of Science ®Google Scholar
• Chang, Y.-J.; Jin, J.; Nam, H.-Y.; Kim, S.-U. Point mutation of (+)-germacrene A synthase from Ixeris dentata. Biotechnol. Lett. 2005, 27, 285–288.
   PubMed Web of Science ®Google Scholar
• Bennett, M.H.; Mansfield, J.W.; Lewis, M.J.; Beale, M.H. Cloning and expression of sesquiterpene synthase genes from lettuce (Lactuca sativa L.). Phytochemistry 2002, 60, 255–261.
   PubMed Web of Science ®Google Scholar
• van der Hoeven, R.S.; Monforte, A.J.; Breeden, D.; Tanksley, S.D.; Steffens, J.C. Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum. Plant Cell Online 2000, 12, 2283–2294.
   PubMed Web of Science ®Google Scholar
• Colby, S.M.; Crock, J.; Dowdle-Rizzo, B.; Lemaux, P.G.; Croteau, R. Germacrene C synthase from Lycopersicon esculentum cv. VFNT Cherry tomato: cDNA isolation, characterization, and bacterial expression of the multiple product sesquiterpene cyclase. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 2216–2221.
   PubMed Web of Science ®Google Scholar
• Pechous, S.W.; Whitaker, B.D. Cloning and functional expression of an (E, E)-α-farnesene synthase cDNA from peel tissue of apple fruit. Planta 2004, 219, 84–94.
   PubMed Web of Science ®Google Scholar
• Gomez, S.K.; Cox, M.M.; Bede, J.C.; Inoue, K.; Alborn, H.T.; Tumlinson, J.H.; Korth, K.L. Lepidopteran herbivory and oral factors induce transcripts encoding novel terpene synthases in Medicago truncatula. Arch. Insect Biochem. Physiol. 2005, 58, 114–127.
   PubMed Web of Science ®Google Scholar
• Arimura, G.-i.; Garms, S.; Maffei, M.; Bossi, S.; Schulze, B.; Leitner, M.; Mithöfer, A.; Boland, W. Herbivore-induced terpenoid emission in Medicago truncatula: Concerted action of jasmonate, ethylene and calcium signaling. Planta 2008, 227, 453–464.
   PubMed Web of Science ®Google Scholar
• Prosser, I.M.; Adams, R.J.; Beale, M.H.; Hawkins, N.D.; Phillips, A.L.; Pickett, J.A.; Field, L.M. Cloning and functional characterisation of a cis-muuroladiene synthase from black peppermint (Mentha × piperita) and direct evidence for a chemotype unable to synthesise farnesene. Phytochemistry 2006, 67, 1564–1571.
   PubMed Web of Science ®Google Scholar
• Bohlmann, J.; Stauber, E.J.; Krock, B.; Oldham, N.J.; Gershenzon, J.; Baldwin, I.T. Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. Phytochemistry 2002, 60, 109–116.
   PubMed Web of Science ®Google Scholar
• Cheng, A.-X.; Xiang, C.-Y.; Li, J.-X.; Yang, C.-Q.; Hu, W.-L.; Wang, L.-J.; Lou, Y.-G.; Chen, X.-Y. The rice (E)-β-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes. Phytochemistry 2007, 68, 1632–1641.
   PubMed Web of Science ®Google Scholar
• Cho, E.-M.; Okada, A.; Kenmoku, H.; Otomo, K.; Toyomasu, T.; Mitsuhashi, W.; Sassa, T.; Yajima, A.; Yabuta, G.; Mori, K., et al. Molecular cloning and characterization of a cDNA encoding ent-cassa-12,15-diene synthase, a putative diterpenoid phytoalexin biosynthetic enzyme, from suspension-cultured rice cells treated with a chitin elicitor. Plant J. 2004, 37, 1–8.
   PubMed Web of Science ®Google Scholar
• Nemoto, T.; Cho, E.-M.; Okada, A.; Okada, K.; Otomo, K.; Kanno, Y.; Toyomasu, T.; Mitsuhashi, W.; Sassa, T.; Minami, E., et al. Stemar-13-ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice. FEBS Lett. 2004, 571, 182–186.
   PubMed Web of Science ®Google Scholar
• Sallaud, C.; Rontein, D.; Onillon, S.; Jabès, F.; Duffé, P.; Giacalone, C.; Thoraval, S.; Escoffier, C.; Herbette, G.; Leonhardt, N, et al. A novel pathway for sesquiterpene biosynthesis from Z, Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites. Plant Cell 2009, 21, 301–317.
   PubMed Web of Science ®Google Scholar
• Köllner, T.G.; Schnee, C.; Gershenzon, J.; Degenhardt, J. The variability of sesquiterpenes emitted from two Zea mays cultivars is controlled by allelic variation of two terpene synthase genes encoding stereoselective multiple product enzymes. Plant Cell Online 2004, 16, 1115–1131.
   PubMed Web of Science ®Google Scholar
• Davis, E.M.; Croteau, R. Cyclization enzymes in the biosynthesis of monoterpenes, sesquiterpenes, and diterpenes. In Biosynthesis; Springer: Berlin Heidelberg, Germany, 2000; pp 53–95.
   Google Scholar
• Bohlmann, J.; Gershenzon, J. Old substrates for new enzymes of terpenoid biosynthesis. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 10402–10403.
   PubMed Web of Science ®Google Scholar
• Falara, V.; Akhtar, T.A.; Nguyen, T.T.H.; Spyropoulou, E.A.; Bleeker, P.M.; Schauvinhold, I.; Matsuba, Y.; Bonini, M.E.; Schilmiller, A.L.; Last, R.L., et al. The tomato terpene synthase gene family. Plant Physiol. 2011, 157, 770–789.
   PubMed Web of Science ®Google Scholar
• Demissie, Z.A.; Erland, L.A.E.; Rheault, M.R.; Mahmoud, S.S. The Biosynthetic origin of irregular monoterpenes in Lavandula Isolation and biochemical characterization of a novel cis-prenyl diphosphate synthase gene, lavandulyl diphosphate synthase. J. Biol. Chem. 2013, 288, 6333–6341.
   PubMed Web of Science ®Google Scholar
• Hsieh, F.L.; Chang, T.H.; Ko, T.P.; Wang, A.H.J. Structure and mechanism of an Arabidopsis medium/long-chain-length prenyl pyrophosphate synthase. Plant Physiol. 2011, 155, 1079–1090.
   PubMed Web of Science ®Google Scholar
• Effmert, U.; Große, J.; Röse, U.S.R.; Ehrig, F.; Kägi, R.; Piechulla, B. Volatile composition, emission pattern, and localization of floral scent emission in Mirabilis jalapa (Nyctaginaceae). Am. J. Bot. 2005, 92, 2–12.
   PubMed Web of Science ®Google Scholar
• Dong, L.; Miettinen, K.; Goedbloed, M.; Verstappen, F.W.A.; Voster, A.; Jongsma, M.A.; Memelink, J.; Krol, Svd.; Bouwmeester, H.J. Characterization of two geraniol synthases from Valeriana officinalis and Lippia dulcis: Similar activity but difference in subcellular localization. Metab. Eng. 2013, 20, 198–211.
   PubMed Web of Science ®Google Scholar
• Szkopiñska, A.; Plochocka, D. Farnesyl diphosphate synthase; regulation of product specificity. Acta Biochim. Pol. 2005, 52, 45–55.
   PubMed Web of Science ®Google Scholar
• Manzano, D.; Busquets, A.; Closa, M.; Hoyerová, K.; Schaller, H.; Kamínek, M.; Arró, M.; Ferrer, A. Overexpression of farnesyl diphosphate synthase in Arabidopsis mitochondria triggers light-dependent lesion formation and alters cytokinin homeostasis. Plant Mol. Biol. 2006, 61, 195–213.
   PubMed Web of Science ®Google Scholar
• Bouwmeester, H.J.; Gershenzon, J.; Konings, M.C.; Croteau, R. Biosynthesis of the monoterpenes limonene and carvone in the fruit of caraway I. Demonstration of Enzyme activities and their changes with development. Plant Physiol. 1998, 117, 901–912.
   Google Scholar
• Turner, G.W.; Croteau, R. Organization of monoterpene biosynthesis in Mentha. Immunocytochemical localizations of geranyl diphosphate synthase, limonene-6-hydroxylase, isopiperitenol dehydrogenase, and pulegone reductase. Plant Physiol. 2004, 136, 4215–4227.
   Google Scholar
• Turner, G.W.; Gershenzon, J.; Croteau, R.B. Development of peltate glandular trichomes of peppermint. Plant Physiol. 2000, 124, 665–680.
   PubMed Web of Science ®Google Scholar
• Belingheri, L.; Gleizes, M.; Pauly, G.; Carde, J.P.; Marpeau, A. Isolation of cell compartments involved in the biosynthesis of lower terpenoids of Citrofortunella mitis fruits. In Biological Role of Plant Lipids; Biacs, P.A.; Gruiz, K.; Kremmer, T., Eds.; Springer: US; 1989, pp 303–308.
   Google Scholar
• Belingheri, L.; Pauly, G.; Gleizes, M.; Marpeau, A. Isolation by an aqueous two-polymer phase system and identification of endomembranes from Citrofortunella mitis fruits for sesquiterpene hydrocarbon synthesis. J. Plant Physiol. 1988, 132, 80–85.
   Web of Science ®Google Scholar
• Lee, D.S.; Lee, S.H.; Lee, Y.B. Effect of Environment on growth and quality of peppermint (Mentha piperita L.). In XXVI International Horticultural Congress: Protected Cultivation 2002: In Search of Structures, Systems and Plant Materials for Sustainable Greenhouse Production; Papadopoulos, A.P., Ed.; ISHS Acta Horticulturae 633: Toronto, Canada, 2002; pp 253–258.
   Google Scholar
• Abbaszadeh, B.; Teymoori, M.; Pouyanfar, M.; Rezaei, M.B.; Mafakheri, S. Growth and essential oil of Mentha longifolia L. var. amphilema from different ecological conditions. Ann. Biol. Res. 2013, 4, 85–90.
   Google Scholar
• Abdelmajeed, N.A.; Danial, E.N.; Ayad, H.S. The effect of environmental stress on qualitative and quantitative essential oil of aromatic and medicinal plants. Arch. Sci. 2013, 66, 100–120.
   Google Scholar
• Hassiotisa, C.N.; Ntanab, F.; Lazaric, D.M.; Pouliosb, S.; Vlachonasiosb, K.E. Environmental and developmental factors affect essential oil production and quality of Lavandula angustifolia during flowering period. Ind. Crops Prod. 2014, 62, 359–366.
   Web of Science ®Google Scholar
• Hu, Z.; Zhang, H.; Leng, P.; Zhao, J.; Wang, W.; Wang, S. The emission of floral scent from Lilium ‘siberia’ in response to light intensity and temperature. Acta Physiol. Plant. 2013, 35, 1691–1700.
   Web of Science ®Google Scholar
• Salim, E.A.; El Hassan, G.M.; Khalid, H.E.S. Effect of spacing and seasonal variation on growth parameters, yield and oil content of mint plants. J. For. Prod. Ind. 2014, 3, 71–74.
   Google Scholar
• Khalid, K.A. Effect of N.P. foliar spray on growth and chemical compositions of some medicinal Apiaceae plants grow in arid regions in Egypt. J. Soil Sci. Plant Nutr. 2012, 12, 581–596.
   Web of Science ®Google Scholar
• Nurzyńska-Wierdak, R. Does mineral fertilization modify essential oil content and chemical composition in medicinal plants? Acta Sci. Pol. Hort. Cult. 2013, 12, 3–16.
   Web of Science ®Google Scholar
• Khorasaninejad, S.; Mousavi, A.; Soltanloo, H.; Hemmati, K.; Khalighi, A. The effect of drought stress on growth parameters, essential oil yield and constituent of peppermint (Mentha piperita L.). J. Med. Plants Res. 2011, 5, 5360–5365.
   Web of Science ®Google Scholar
• Khorasaninejad, S.; Mousavi, A.; Soltanloo, H.; Hemmati, K.; Khalighi, A. The effect of salinity stress on growth parameters, essential oil yield and constituent of peppermint (Mentha piperita L.). World Appl. Sci. J. 2010, 11, 1403–1407.
   Google Scholar
• Chang, X.; Alderson, P.G.; Wright, C.J. Enhanced UV-B radiation alters basil (Ocimum basilicum L.) growth and stimulates the synthesis of volatile oils. J. Hortic. For. 2009, 12, 27–31.
   Google Scholar
• Khorshidi, J.; Tabatabaie, M.F.; Omidbaigi, R.; Sefidkon, F. Effect of densities of planting on yield and essential oil components of Fennel (Foeniculum vulgare Mill Var. Soroksary). J. Agric. Sci. 2009, 1, 152–157.
   Google Scholar
• Blande, J.D.; Holopainen, J.K.; Niinemets, Ü. Plant volatiles in polluted atmospheres: Stress responses and signal degradation. Plant Cell Environ. 2014, 37, 1892–1904.
   PubMed Web of Science ®Google Scholar
• Loreto, F.; Schnitzler, J.-P. Abiotic stresses and induced BVOCs. Trends Plant Sci. 2010, 15, 154–166.
   PubMed Web of Science ®Google Scholar
• Adam, D. Scientists discover cloud-thickening chemicals in trees that could offer a new weapon in the fight against global warming. The Guardian 2008. http://www.theguardian.com/environment/2008/oct/31/forests-climatechange
   Google Scholar
• Kandi, S.; Godishala, V.; Rao, P.; Ramana, K.V. Biomedical significance of terpenes: An insight. Biomedicine 2015, 3, 8–10.
   Google Scholar
• Kesselmeier, J.; Staudt, M. Biogenic volatile organic compounds (VOC): An overview on emission, physiology and ecology. J. Atmos. Chem. 1999, 33, 23–88.
   Web of Science ®Google Scholar
• Sharkey, T.D.; Wiberley, A.E.; Donohue, A.R. Isoprene emission from plants: Why and how. Ann. Bot. 2008, 101, 5–18.
   PubMed Web of Science ®Google Scholar
• Spinelli, F.; Cellini, A.; Piovene, C.; Nagesh, K.M.; Marchetti, L. Emission and Function Of Volatile Organic Compounds in Response to Abiotic Stress; INTECH Open Access Publisher: Croatia, 2011.
   Google Scholar
• Sharkey, T.D. Why plants emit isoprene. Nature 1995, 374, 769.
   Web of Science ®Google Scholar
• Singsaas, E.; Sharkey, T. The regulation of isoprene emission responses to rapid leaf temperature fluctuations. Plant Cell Environ. 1998, 21, 1181–1188.
   Web of Science ®Google Scholar
• Rasulov, B.; Hüve, K.; Bichele, I.; Laisk, A.; Niinemets, Ü. Temperature response of isoprene emission in vivo reflects a combined effect of substrate limitations and isoprene synthase activity: A kinetic analysis. Plant Physiol. 2010, 154, 1558–1570.
   PubMed Web of Science ®Google Scholar
• Hanson, D.T.; Swanson, S.; Graham, L.E.; Sharkey, T.D. Evolutionary significance of isoprene emission from mosses. Am. J. Bot. 1999, 86, 634–639.
   PubMed Web of Science ®Google Scholar
• Jun-Wen, C.; Cao K.-F. Plant VOCs emission: A new strategy of thermotolerance. J. For. Res. 2005, 16, 323–326.
   Google Scholar
• Keeling, C.I.; Bohlmann, J. Genes,enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens. New Phytol. 2006, 170, 657–675.
   PubMed Web of Science ®Google Scholar
• Zulak, K.G.; Bohlmann, J. Terpenoid biosynthesis and specialized vascular cells of conifer defense. J. Integr. Plant Biol. 2010, 52, 86–97.
   PubMed Web of Science ®Google Scholar
• Vuorinen, T.; Reddy, G.; Nerg, A.-M.; Holopainen, JK. Monoterpene and herbivore-induced emissions from cabbage plants grown at elevated atmospheric CO2 concentration. Atmos. Environ. 2004, 38, 675–682.
   Web of Science ®Google Scholar
• Jardine, K.; Yanez Serrano, A.; Arneth, A.; Abrell, L.; Jardine, A.; van Haren, J.; Artaxo, P.; Rizzo, L.V.; Ishida, F.Y.; Karl, T. Within-canopy sesquiterpene ozonolysis in Amazonia. J. Geophys. Res. Atmos. 2011, 116, D19301.
   Google Scholar
• Koul, O.; Walia, S.; Dhaliwal, G.S. Essential oils as green pesticides: Potential and constraints. Biopestic. Int. 2008, 4, 63–84.
   Google Scholar
• Kordali, S.; Cakir, A.; Mavi, A.; Kilic, H.; Yildirim, A. Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish Artemisia species. J. Agric. Food Chem. 2005, 53, 1408–1416.
   PubMed Web of Science ®Google Scholar
• Baser, K.H.C.; Buchbauer, G. Handbook of Essential Oils: Science, Technology, and Applications. CRC Press: Boca Raton, FL, 2009.
   Google Scholar
• Fukumoto, S.; Morishita, A.; Furutachi, K.; Terashima, T.; Nakayama, T.; Yokogoshi, H. Effect of flavour components in lemon essential oil on physical or psychological stress. Stress Health 2008, 24, 3–12.
   Web of Science ®Google Scholar
• Alexandrovich, I.; Rakovitskaya, O.; Kolmo, E.; Sidorova, T.; Shushunov, S. The effect of fennel (Foeniculum vulgare) seed oil emulsion in infantile colic: A randomized, placebo-controlled study. Altern. Ther. Health Med. 2003, 9, 58–61.
   PubMed Web of Science ®Google Scholar
• Edris, A.E. Pharmaceutical and therapeutic potentials of essential oils and their individual volatile constituents: A review. Phytother. Res. 2007, 21, 308–323.
   PubMed Web of Science ®Google Scholar
• Djilani, A.; Dicko, A. The Therapeutic Benefits of Essential Oils. INTECH Open Access Publisher: Croatia, 2012.
   Google Scholar
• Tisserand, R.; Young, R. Essential Oil Safety: A Guide for Health Care Professionals; Elsevier Health Sciences: United Kingdom, 2013.
   Google Scholar
• Johnson, S.; Boren, K. Topical and oral administration of essential oils—Safety issues. Aromatopia 2013, 22, 43–48.
   Google Scholar
• Angelucci, F.L.; Silva, V.V.; Dal Pizzol, C.; Spir, L.G.; Praes, C.; Maibach, H. Physiological effect of olfactory stimuli inhalation in humans: An overview. Int. J. Cosmet. Sci. 2014, 36, 117–123.
   PubMed Web of Science ®Google Scholar
• Anchisi, C.; Meloni, M.C.; Maccioni, A.M. Chitosan beads loaded with essential oils in cosmetic formulations. Int. J. Cosmet. Sci. 2006, 29, 205–214.
   Google Scholar
• Muyima, N.; Zulu, G.; Bhengu, T.; Popplewell, D. The potential application of some novel essential oils as natural cosmetic preservatives in an aqueous cream formulation. Flavour Fragr. J. 2002, 17, 258–266.
   Web of Science ®Google Scholar
• Bakkali, F.; Averbeck, S.; Averbeck, D.; Idaomar, M. Biological effects of essential oils—A review. Food Chem. Toxicol. 2008, 46, 446–475.
   PubMed Web of Science ®Google Scholar
• Kim, S.H.; Lee, S.Y.; Hong, C.Y.; Gwak, K.S.; Park, M.J.; Smith, D.; Choi, I.G. Whitening and antioxidant activities of bornyl acetate and nezukol fractionated from Cryptomeria japonica essential oil. Int. J. Cosmet. Sci. 2013, 35, 484–490.
   PubMed Web of Science ®Google Scholar
• Dreger, M.; Wielgus, K. Application of essential oils as natural cosmetic preservatives. Herba Pol. 2013, 59, 142–156.
   Google Scholar
• El Abed, N.; Kaabi, B.; Smaali, M.I.; Chabbouh, M.; Habibi, K.; Mejri, M.; Marzouki, M.N.; Ben Hadj Ahmed, S. Chemical composition, antioxidant and antimicrobial activities of Thymus capitata essential oil with its preservative effect against Listeria monocytogenes inoculated in minced beef meat. Evid. Based Complementary Altern. Med. 2014, 2014, 1–11.
   Google Scholar
• Candan, F.; Unlu, M.; Tepe, B.; Daferera, D.; Polissiou, M.; Sökmen, A.; Akpulat, H.A. Antioxidant and antimicrobial activity of the essential oil and methanol extracts of Achillea millefolium subsp. millefolium Afan. (Asteraceae). J. Ethnopharmacol. 2003, 87, 215–220.
   PubMed Web of Science ®Google Scholar
• Prabuseenivasan, S.; Jayakumar, M.; Ignacimuthu, S. In vitro antibacterial activity of some plant essential oils. BMC Complementary Altern. Med. 2006, 6, 39.
   PubMedGoogle Scholar
• Soković, M.; Marin, P.D.; Brkić, D.; Van Griensven, L. Chemical composition and antibacterial activity of essential oils of ten aromatic plants against human pathogenic bacteria. Food 2007, 1, 220–226.
   Google Scholar
• Sartoratto, A.; Machado, A.L.M.; Delarmelina, C.; Figueira, G.M.; Duarte, M.C.T.; Rehder, V.L.G. Composition and antimicrobial activity of essential oils from aromatic plants used in Brazil. Braz. J. Microbiol. 2004, 35, 275–280.
   Web of Science ®Google Scholar
• Garcia, C.C.; Talarico, L.; Almeida, N.; Colombres, S.; Duschatzky, C.; Damonte, E.B. Virucidal activity of essential oils from aromatic plants of San Luis, Argentina. Phytother. Res. 2003, 17, 1073–1075.
   PubMed Web of Science ®Google Scholar
• Turina, A.dV.; Nolan, M.; Zygadlo, J.; Perillo, M. Natural terpenes: Self-assembly and membrane partitioning. Biophys. Chem. 2006, 122, 101–113.
   PubMed Web of Science ®Google Scholar
• Di Pasqua, R.; Hoskins, N.; Betts, G.; Mauriello, G. Changes in membrane fatty acids composition of microbial cells induced by addiction of thymol, carvacrol, limonene, cinnamaldehyde, and eugenol in the growing media. J. Agric. Food Chem. 2006, 54, 2745–2749.
   PubMed Web of Science ®Google Scholar
• Harold, E.L.; Simone, H.G.; Geraldine, W. Antimicrobial activity of multipurpose essential oil blends. Health 2012, 4, 443–447.
   Google Scholar
• Kunicka-Styczyńska, A.; Sikora, M.; Kalemba, D. Lavender, tea tree and lemon oils as antimicrobials in washing liquids and soft body balms. Int. J. Cosmet. Sci. 2011, 33, 53–61.
   PubMed Web of Science ®Google Scholar
• Dudareva, N.; Pichersky, E. Biology of Floral Scent; CRC Press: Boca Raton, FL, 2010.
   Google Scholar
• Degenhardt, J.; Gershenzon, J.; Baldwin, I.T.; Kessler, A. Attracting friends to feast on foes: Engineering terpene emission to make crop plants more attractive to herbivore enemies. Curr. Opin. Biotechnol. 2003, 14, 169–176.
   PubMed Web of Science ®Google Scholar
• Khan, Z.R.; Pickett, J.A.; Berg, J.vd.; Wadhams, L.J.; Woodcock, C.M. Exploiting chemical ecology and species diversity: Stem borer and striga control for maize and sorghum in Africa. Pest Manage. Sci. 2000, 56, 957–962.
   Web of Science ®Google Scholar
• Aharoni, A.; Giri, A.P.; Deuerlein, S.; Griepink, F.; de Kogel, W.-J.; Verstappen, F.W.A.; Verhoeven, H.A.; Jongsma, M.A.; Schwab, W.; Bouwmeester, H.J. Terpenoid metabolism in wild-type and transgenic Arabidopsis plants. Plant Cell Online 2003, 15, 2866–2884.
   PubMed Web of Science ®Google Scholar
• Aharoni, A.; Jongsma, M.A.; Kim, T.Y.; Ri, M.B.; Giri, A.P.; Verstappen, F.W.A.; Schwab, W.; Bouwmeester, H.J. Metabolic engineering of terpenoid biosynthesis in plants. Phytochem. Rev. 2006, 5, 49–58.
   Google Scholar
• Stockhorst, U.; Pietrowsky, R. Olfactory perception, communication, and the nose-to-brain pathway. Physiol. Behav. 2004, 83, 3–11.
   PubMed Web of Science ®Google Scholar
• Lücker, J.; Schwab, W.; van Hautum, B.; Blaas, J.; van der Plas, L.H.W.; Bouwmeester, H.J.; Verhoeven, H.A. Increased and altered fragrance of tobacco plants after metabolic engineering using three monoterpene synthases from lemon. Plant Physiol. 2004, 134, 510–519.
   PubMed Web of Science ®Google Scholar
• Aranovich, D.; Lewinsohn, E.; Zaccai, M. Post-harvest enhancement of aroma in transgenic lisianthus (Eustoma grandiflorum) using the Clarkia breweri benzyl alcohol acetyltransferase (BEAT) gene. Postharvest Biol. Technol. 2007, 43, 255–260.
   Web of Science ®Google Scholar
• Lucker, J.; Bouwmeester, H.J.; Schwab, W.; Blaas, J.; Van Der Plas, L.H.W.; Verhoeven, H.A. Expression of Clarkia S-linalool synthase in transgenic petunia plants results in the accumulation of S-linalyl-β-d-glucopyranoside. Plant J. 2001, 27, 315–324.
   PubMed Web of Science ®Google Scholar
• Lavy, M.; Zuker, A.; Lewinsohn, E.; Larkov, O.; Ravid, U.; Vainstein, A.; Weiss, D. Linalool and linalool oxide production in transgenic carnation flowers expressing the Clarkia breweri linalool synthase gene. Mol. Breed. 2002, 9, 103–111.
   Web of Science ®Google Scholar
• Lewinsohn, E.; Schalechet, F.; Wilkinson, J.; Matsui, K.; Tadmor, Y.; Nam, K.H.; Amar, O.; Lastochkin, E.; Larkov, O.; Ravid, U. Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits. Plant Physiol. 2001, 127, 1256–1265.
   PubMed Web of Science ®Google Scholar
• Davidovich-Rikanati, R.; Sitrit, Y.; Tadmor, Y.; Iijima, Y.; Bilenko, N.; Bar, E.; Carmona, B.; Fallik, E.; Dudai, N.; Simon, J.E. Enrichment of tomato flavor by diversion of the early plastidial terpenoid pathway. Nat. Biotechnol. 2007, 25, 899–901.
   PubMed Web of Science ®Google Scholar
• Mahmoud, S.S.; Williams, M.; Croteau, R. Cosuppression of limonene-3-hydroxylase in peppermint promotes accumulation of limonene in the essential oil. Phytochemistry 2004, 65, 547–554.
   PubMed Web of Science ®Google Scholar
• Lange, B.M.; Ahkami, A. Metabolic engineering of plant monoterpenes, sesquiterpenes and diterpenes—Current status and future opportunities. Plant Biotechnol. J. 2013, 11, 169–196.
   PubMed Web of Science ®Google Scholar