Phytochemistry Reviews

, Volume 13, Issue 3, pp 695–716 | Cite as

The evolution of foliar terpene diversity in Myrtaceae

  • Amanda Padovan
  • András Keszei
  • Carsten Külheim
  • William J. Foley


Plant terpenes play many roles in natural systems, from altering plant–animal interactions, to altering the local abiotic environment. Additionally, many industries depend on terpenes. For example, commercially used essential oils, including tea tree oil and lavender oil, are a mixture of terpenes. Many species of the family Myrtaceae form a key resource for these industries due to the high concentration of terpenes found predominately in their leaves. The frequency of chemotypic differences within many species and populations can lead to costly errors in industry. Terpene diversity in Myrtaceae is driven by variation in the terpene synthase enzymes, which catalyse the conversion a few common substrates into thousands of terpene structures. We review terpene diversity within and between species of Myrtaceae and relate this to variation in the terpene synthase enzymes to reconstruct the evolution of foliar terpene diversity in Myrtaceae. We found that (1) high inter- and intra-species variation exists in terpene profile and that α-pinene the most likely ancestral foliar terpene, and (2) that high concentration of 1,8-cineole (a compound which is regarded as the signature compound of Myrtaceae) is limited to just four Myrtaceae sub-families. We suggest that the terpene synthase enzymes do not limit terpene diversity in this family and variation in these enzymes suggests a mode of enzymatic evolution that could lead to high 1,8-cineole production. Our analysis highlights the need to standardise methods for collecting and reporting foliar terpene data, and we discuss some methods and issues here. Although there are many gaps in the published data, our large scale analysis using the results of many studies, shows the value of a family wide analysis for understanding both the evolution and industrial potential of terpene-producing plants.


Monoterpene Sesquiterpene Terpene synthase Eucalyptus Melaleuca Cineole Evolution 



This research was supported by a grant from the Australian Research Council to WJF (LP110100184). We thank our partners in that work (Australian Tea Tree Industry Association and GR Davis) for their support and appreciate the advice and comments of many essential oil chemists.

Supplementary material

11101_2013_9331_MOESM1_ESM.xls (1.1 mb)
Supplementary material 1 (XLS 1138 kb): A heat map of the most abundant foliar terpenes found in Myrtaceae. The 110 terpenes are listed in the first row and the 1393 species of Myrtaceae are listed in the first column. The most abundant compound is coloured in the darkest colour (1) and the sixth most abundant compound (6) is coloured in the lightest colour in each row
11101_2013_9331_MOESM2_ESM.doc (66 kb)
Supplementary material 2 (DOC 66 kb)


  1. Aharoni A, Giri AP, Verstappen FWA, Bertea CM, Sevenier R, Sun Z, Jongsma MA, Schwab W, Bouwmeester HJ (2004) Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Plant Cell 16:3110–3131PubMedCentralPubMedCrossRefGoogle Scholar
  2. Ammon DG, Barton AFM, Clarke DA, Tjandra J (1985) Rapid and accurate chemical determination of the water content of plants containing volatile oils. Analyst 110:917–920CrossRefGoogle Scholar
  3. Andrew R, Wallis I, Harwood C, Henson M, Foley W (2007) Heritable variation in the foliar secondary metabolite sideroxylonal in Eucalyptus confers cross-resistance to herbivores. Oecologia 153:891–901PubMedCrossRefGoogle Scholar
  4. Andrew RL, Wallis IR, Harwood CE, Foley WJ (2010) Genetic and environmental contributions to variation and population divergence in a broad-spectrum foliar defence of Eucalyptus tricarpa. Ann Bot 105:707–717PubMedCentralPubMedCrossRefGoogle Scholar
  5. Andrew RL, Keszei A, Foley WJ (2013) Intensice sampling identifies new chemotypes, population divergence and biosynthetic connections among terpenoids in Eucalyptus tricarpa. Phytochemistry 94:148–158Google Scholar
  6. Arnold K, Bordoli L, Kopp J, Schwede T (2006) The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling. Bioinformatics 22:195–201PubMedCrossRefGoogle Scholar
  7. Biffin E, Lucas EJ, Craven LA, Ribeiro da Costa I, Harrington MG, Crisp MD (2010) Evolution of exceptional species richness among lineages of fleshy-fruited Myrtaceae. Ann Bot 106:79–93PubMedCentralPubMedCrossRefGoogle Scholar
  8. Birks JS, Kanowski PJ (1993) Analysis of resin compositional data. Silvae Genet 42:340–350Google Scholar
  9. Bohlmann J, Keeling CI (2008) Terpenoid biomaterials. Plant J 54:656–669PubMedCrossRefGoogle Scholar
  10. Bohlmann J, Crock J, Jetter R, Croteau R (1998) Terpenoid-based defenses in conifers: cDNA cloning, characterization, and functional expression of wound-inducible (E)-alpha-bisabolene synthase from grand fir (Abies grandis). PNAS 95:6756–6761PubMedCentralPubMedCrossRefGoogle Scholar
  11. Boland DJ, Brophy JJ, House APN (1991) Eucalyptus leaf oils. Use, chemistry, distillation and marketing. Inkata Press, Sydney, AustraliaGoogle Scholar
  12. Bouwmeester HJ, Verstappen FWA, Posthumus MA, Dicke M (1999) Spider mite-induced (3S)-(E)-nerolidol synthase activity in cucumber and lima bean. The first dedicated step in acyclic C11-homoterpene biosynthesis. Plant Physiol 121:173–180PubMedCentralPubMedCrossRefGoogle Scholar
  13. Brophy JJ, Southwell IA (2002) Eucalyptus chemistry. In: Coppen JJ (ed) Eucalyptus: the genus Eucalyptus. Taylor and Francis, New YorkGoogle Scholar
  14. Brophy JJ, Goldsack RJ, Forster PI (2006) A preliminary examination of the leaf oils of the genus Xanthostemon (Myrtaceae) in Australia. J Essent Oil Res 18:222–230CrossRefGoogle Scholar
  15. Butcher PA, Doran JC, Slee MU (1994) Intraspecific variation in the leaf oils of Melaleuca alternifolia (Myrtaceae). Biochem Syst Ecol 22:419–430CrossRefGoogle Scholar
  16. Carnegie AJ, Lidbetter JR, Walker J, Horwood MA, Tesoriero L, Glen M, Priest MJ (2010) Uredo rangelii, a taxon in the guava rust complex, newly recorded on Myrtaceae in Australia. Australas Plant Pathol 39:463–466CrossRefGoogle Scholar
  17. Carson CF, Hammer KA, Riley TV (2006) Melaleuca alternifolia (tea tree) oil: a review of antimicrobial and other medicinal properties. Clin Microbiol Rev 19:50–62PubMedCentralPubMedCrossRefGoogle Scholar
  18. Charles DJ, Simon JE (1990) Comparison of extraction methods for the rapid determination of essential oil content and composition of basil. J Am Soc Hortic Sci 115:458–462Google Scholar
  19. Chen H-C, Sheu M-J, Lin L-Y, Wu C-M (2007) Chemical composition of the leaf essential oil of Psidium guajava L. from Taiwan. J Essent Oil Res 19:345–347CrossRefGoogle Scholar
  20. Christensson JB, Forsström P, Wennberg A-M, Karlberg A-T, Matura M (2009) Air oxidation increases skin irritation from fragrance terpenes. Contact Dermatitis 60:32–40CrossRefGoogle Scholar
  21. Cornwell CP, Reddy N, Leach DN, Grant WS (2000a) Origin of (+)-delta-cadinene and the cubenols in the essential oils of the Myrtaceae. Flavour Fragr J 15:352–361CrossRefGoogle Scholar
  22. Cornwell CP, Reddy N, Leach DN, Wyllie SG (2000b) Hydrolysis of hedycaryol: the origin of the eudesmols in the Myrtaceae. Flavour Fragr J 15:421–431CrossRefGoogle Scholar
  23. Cornwell CP, Reddy N, Leach DN, Wyllie SG (2001) Germacradienols in the essential oils of the Myrtaceae. Flavour Fragr J 16:263–273CrossRefGoogle Scholar
  24. Crankshaw DR, Langenheim JH (1981) Variation in terpenes and phenolics through leaf development in Hymenaea and its possible significance to herbivory. Biochem Syst Ecol 9:115–124CrossRefGoogle Scholar
  25. Croteau R, Davis E, Ringer K, Wildung M (2005) (−)-Menthol biosynthesis and molecular genetics. Naturwissenschaften 92:562–577PubMedCrossRefGoogle Scholar
  26. De Vincenzi M, Silano M, De Vincenzi A, Maialetti F, Scazzocchio B (2002) Constituents of aromatic plants: eucalyptol. Fitoterapia 73:269–275PubMedCrossRefGoogle Scholar
  27. DeGabriel J, Moore B, Shipley L, Krockenberger A, Wallis IR, Johnson C, Foley WJ (2009) Inter-population differences in the tolerance of a marsupial folivore to plant secondary metabolites. Oecologia 161:539–548PubMedCrossRefGoogle Scholar
  28. Degenhardt J, Köllner TG, Gershenzon J (2009) Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry 70:1621–1637PubMedCrossRefGoogle Scholar
  29. Dudareva N, Andersson S, Orlova I, Gatto N, Reichelt M, Rhodes D, Boland W, Gershenzon J (2005) The nonmevalonate pathway supports both monoterpene and sesquiterpene formation in snapdragon flowers. Plant Biol 102:933–938Google Scholar
  30. Fähnrich A, Krause K, Piechulla B (2011) Product variability of the ‘cineole cassette’ monoterpene synthases of related Nicotiana species. Mol Plant 4:965–984PubMedCrossRefGoogle Scholar
  31. Govaerts, R (2008) World checklist of Myrtaceae: Kew PubGoogle Scholar
  32. Grattapaglia D, Vaillancourt R, Shepherd M, Thumma B, Foley W, Külheim C, Potts B, Myburg A (2012) Progress in Myrtaceae genetics and genomics: Eucalyptus as the pivotal genus. TGG 8:463–508Google Scholar
  33. Greenhagen BT, O’Maille PE, Noel JP, Chappell J (2006) Identifying and manipulating structural determinates linking catalytic specificities in terpene synthases. PNAS 103:9826–9831PubMedCentralPubMedCrossRefGoogle Scholar
  34. Grubb PJ, Metcalfe DJ, Grubb EA, Jones GD (1998) Nitrogen-richness and prtoection of seeds in Australian tropical rainforest: a test of plant defence theory. Oikos 82:467–482CrossRefGoogle Scholar
  35. Guex N, Peitsch M, Schwede T, Diemand A (1995–2011) DeepView/Swiss-PdbViewer v4.0.4. Swiss Institute of BioinformaticsGoogle Scholar
  36. Hall D, Robert J, Keeling C, Domanski D, Lara A, Jancsik S, Kuzyk M, Hamberger B, Borchers C, Bohlmann J (2011) An integrated genomic, proteomic and biochemical analysis of (+)-3-carene biosynthesis in Sitka spruce (Picea sitchensis) genotypes that are resistant or susceptible to white pine weevil. Plant J 65:936–948PubMedCrossRefGoogle Scholar
  37. Homer LE, Leach DN, Lea D, Slade Lee L, Henry RJ, Baverstock PR (2000) Natural variation in the essential oil content of Melaleuca alternifolia Cheel (Myrtaceae). Biochem Syst Ecol 28:367–382PubMedCrossRefGoogle Scholar
  38. Horner JD, Gosz JR, Cates RG (1988) The role of carbon-based plant secondary metabolites in decomposition in terrestrial ecosystems. Am Nat 132:869–883CrossRefGoogle Scholar
  39. Huang M, Sanchez-Moreiras AM, Abel C, Sohrabi R, Lee S, Gershenzon J, Tholl D (2012) The major volatile organic compound emitted from Arabidopsis thaliana flowers, the sesquiterpene (E)-β-caryophyllene, is a defense against a bacterial pathogen. New Phytol 193:997–1008PubMedCrossRefGoogle Scholar
  40. Hyatt DC, Croteau R (2005) Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (−)-pinene synthase from Abies grandis. Arch Biochem Biophys 439:222–233PubMedCrossRefGoogle Scholar
  41. Iguchi M, Nishiyama A, Yamamura S, Hirata Y (1969) Conversion of elemene-type sesquiterpenes into cadinene-type compounds and formation of ten-membered germacrone-type intermediates. Tetrahedron Lett 10:4295–4298CrossRefGoogle Scholar
  42. Ireland B, Hibbert D, Goldsack R, Doran J, Brophy J (2002) Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.) S.T. Blake. Biochem Syst Ecol 30:457–470CrossRefGoogle Scholar
  43. Kampranis SC, Ioannidis D, Purvis A, Mahrez W, Ninga E, Katerelos NA, Anssour S, Dunwell JM, Degenhardt J, Makris AM, Goodenough PW, Johnson CB (2007) Rational conversion of substrate and product specificity in a Salvia monoterpene synthase: structural insights into the evolution of terpene synthase function. Plant Cell 19:1994–2005PubMedCentralPubMedCrossRefGoogle Scholar
  44. Kant M, Baldwin I (2007) The ecogenetics and ecogenomics of plant–herbivore interactions: rapid progress on a slippery road. Curr Opin Genet Dev 17:519–524PubMedCrossRefGoogle Scholar
  45. Katoh S, Hyatt D, Croteau R (2004) Altering product outcome in Abies grandis (−)-limonene synthase and (-)-limonene/(−)-alpha-pinene synthase by domain swapping and directed mutagenesis. Arch Biochem Biophys 425:65–76PubMedCrossRefGoogle Scholar
  46. Kaur R, Kaur H (2010) The antimicrobial activity of essential oil and plant extracts of Woodfordia fruticosa. Arch Appl Sci Res 2:302–309Google Scholar
  47. Keeling C, Bohlmann J (2006) Genes, enzymes and chemicals of terpenoid diversity in the constitutive and induced defence of conifers against insects and pathogens. New Phytol 170:657–675PubMedCrossRefGoogle Scholar
  48. Keszei A, Brubaker CL, Foley WJ (2008) A molecular perspective on terpene variation in Australian Myrtaceae. Aust J Bot 56:197–213CrossRefGoogle Scholar
  49. Keszei A, Brubaker CL, Carter R, Köllner T, Degenhardt J, Foley WJ (2010) Functional and evolutionary relationships between terpene synthases from Australian Myrtaceae. Phytochemistry 71:844–852PubMedCrossRefGoogle Scholar
  50. Köllner TG, Schnee C, Gershenzon J, Degenhardt J (2004) 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 16:1115–1131PubMedCentralPubMedCrossRefGoogle Scholar
  51. Köllner TG, O’Maille PE, Gatto N, Boland W, Gershenzon J, Degenhardt J (2006) Two pockets in the active site of maize sesquiterpene synthase TPS4 carry out sequential parts of the reaction scheme resulting in multiple products. Arch Biochem Biophys 448:83–92PubMedCrossRefGoogle Scholar
  52. Köllner TG, Gershenzon J, Degenhardt J (2009) Molecular and biochemical evolution of maize terpene synthase 10, an enzyme of indirect defense. Phytochemistry 70:1139–1145PubMedCrossRefGoogle Scholar
  53. Külheim C, Webb H, Yeoh SH, Wallis I, Moran G, Foley W (2011) Using the Eucalyptus genome to understand the evolution of plant secondary metabolites in the Myrtaceae. BMC Proc 5:O11PubMedCentralCrossRefGoogle Scholar
  54. Külheim C, Padovan A, Hefer C, Krause S, Degenhardt J, Myburg A, Foley WJ (2013) The Eucalyptus terpene synthase gene family. New Phytol (in press)Google Scholar
  55. Langenheim JH, Foster CE, McGinley RB (1980) Inhibitory effects of different quantitative compositions of Hymenaea leaf resins on a generalist herbivore Spodoptera exigua. Biochem Syst Ecol 8:385–396CrossRefGoogle Scholar
  56. Lawler IR, Foley WJ, Eschler BM, Pass DM, Handasyde K (1998) Intraspecific variation in Eucalyptus secondary metabolites determines food intake by folivorous marsupials. Oecologia 116:160–169CrossRefGoogle Scholar
  57. Levin DA (1976) The chemical defenses of plants to pathogens and hrbivores. Annu Rev Ecol Syst 7:121–159CrossRefGoogle Scholar
  58. Lichtenthaler HK (1999) The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu Rev Plant Physiol Plant Mol Biol 50:47–65PubMedCrossRefGoogle Scholar
  59. Linhart YB, Thompson JD (1995) Terpene-based selective herbivory by Helix aspersa (Mollusca) on Thymus vulgaris (Labiatae). Oecologia 102:126–132Google Scholar
  60. Macel M, Klinkhamer P (2010) Chemotype of Senecio jacobaea affects damage by pathogens and insect herbivores in the field. Evol Ecol 24:237–250CrossRefGoogle Scholar
  61. Maida M, Carroll A, Coll J (1993) Variability of terpene content in the soft coral Sinularia flexibilis (Coelenterata: Octocorallia), and its ecological implications. J Chem Ecol 19:2285–2296PubMedCrossRefGoogle Scholar
  62. Martin D, Aubourg S, Schouwey M, Daviet L, Schalk M, Toub O, Lund S, Bohlmann J (2010) Functional annotation, genome organization and phylogeny of the grapevine (Vitis vinifera) terpene synthase gene family based on genome assembly, FLcDNA cloning, and enzyme assays. BMC Plant Biol 10:226–248PubMedCentralPubMedCrossRefGoogle Scholar
  63. Matsuki M, Foley WJ, Floyd R (2011) Role of volatile and non-volatile plant secondary metabolites in host tree selection by Christmas beetles. J Chem Ecol 37:286–300PubMedCrossRefGoogle Scholar
  64. McCaskill D, Croteau R (1995) Monoterpene and sesquiterpene biosynthesis in glandular trichomes of peppermint (Mentha x piperita) rely exclusively on plastid-derived isopentenyl diphosphate. Planta 197:49–56CrossRefGoogle Scholar
  65. Moore BD, Andrew RL, Külheim C, Foley WJ (2013) Causes and consequences of intraspecific chemical diversity. New Phytol (in press)Google Scholar
  66. Ogunbinu AO, Ogunwande IA, Walker TM, Setzer WN (2007) Study on the essential oil of Lawsonia inermis (L) Lythraceae. J Essent Oil Bear Plants 10:184–188CrossRefGoogle Scholar
  67. Padovan A, Keszei A, Koellner TG, Degenhardt J, Foley WJ (2010) The molecular basis of host plant selection in Melaleuca quinquenervia by a successful biological control agent. Phytochemistry 71:1237–1244PubMedCrossRefGoogle Scholar
  68. Padovan A, Keszei A, Wallis IR, Foley WJ (2012) Mosaic eucalypt trees suggest genetic control at a point that influences several metabolic pathways. J Chem Ecol 38:914–923PubMedCrossRefGoogle Scholar
  69. Pichersky E, Gershenzon J (2002) The formation and function of plant volatiles: perfumes for pollinator attraction and defense. Curr Opin Plant Biol 5:237–243PubMedCrossRefGoogle Scholar
  70. Prosser I, Altug IG, Phillips AL, König WA, Bouwmeester HJ, Beale MH (2004) Enantiospecific (+)- and (−)-germacrene D synthases, cloned from goldenrod, reveal a functionally active variant of the universal isoprenoid-biosynthesis aspartate-rich motif. Arch Biochem Biophys 432:136–144PubMedCrossRefGoogle Scholar
  71. Prosser IM, Adams RJ, Beale MH, Hawkins ND, Phillips AL, Pickett JA, Field LM (2006) 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 67:1564–1571PubMedCrossRefGoogle Scholar
  72. Rasmann S, De Vos M, Casteel CL, Tian D, Halitschke R, Sun JY, Agrawal AA, Felton GW, Jander G (2012) Herbivory in the previous generation primes plants for enhanced insect resistance. Plant Physiol 158:854–863PubMedCentralPubMedCrossRefGoogle Scholar
  73. Slee AV, Brooker MIH, Duffy SM, West JG (2006) EUCLID eucalypts of Australia third edition. CSIRO, CanberraGoogle Scholar
  74. Steffen RB, Antoniolli ZI, Steffen GPK, da Silva RF (2012) Essential oil of Eucalyptus grandis Hill ex Maiden in stimulating mycorrhizal sibipiruna seedlings (Ceasalpinia peltophoroides Benth.). Cienc Florest 22:69–78Google Scholar
  75. Steinbauer MJ (2010) Latitudinal trends in foliar oils of eucalypts: environmental correlates and diversity of chrysomelid leaf-beetles. Austral Ecol 35:204–213CrossRefGoogle Scholar
  76. Stubbs BJ, Specht A, Brushett D (2004) The essential oil of Cinnamomum camphora (L.) Nees and Eberm.—variation in oil composition throughout the tree in two chemotypes from eastern Australia. J Essent Oil Res 16:200–205CrossRefGoogle Scholar
  77. Suni T, Kulmala M, Hirsikko A, Bergman T, Laakso L, Aalto P, Leuning R, Cleugh H, Zegelin S, Hughes D, van Gorsel E, Kitchen M, Vana M, Hõrrak U, Mirme S, Mirme A, Sevanto S, Twining J, Tadros C (2008) Formation and characteristics of ions and charged aerosol particles in a native Australian eucalypt forest. Atmos Chem Phys 8:129–139CrossRefGoogle Scholar
  78. Thornhill AH, Crisp MD (2012) Phylogenetic assessment of pollen characters in Myrtaceae. Aust Syst Bot 25:171–187CrossRefGoogle Scholar
  79. Thornhill AH, Hope GS, Craven LA, Crisp MD (2012) Pollen morphology of the Myrtaceae. Part 4: tribes Kanieae, Myrteae and Tristanieae. Aust J Bot 60:260–289CrossRefGoogle Scholar
  80. Toudahl AB, Filho SAV, Souza GHB, Morais LD, Santos ODH, Jäger AK (2012) Chemical composition of the essential oil from Microlicia graveolens growing wild in Minas Gerais. Rev Bras Farmacogn 22:680–681CrossRefGoogle Scholar
  81. Unsicker SB, Kunert G, Gershenzon J (2009) Protective perfumes: the role of vegetative volatiles in plant defense against herbivores. Curr Opin Plant Biol 12:479–485PubMedCrossRefGoogle Scholar
  82. Van Poecke RMP, Posthumus MA, Dicke M (2001) Herbivore-induced volatile production by Arabidopsis thaliana leads to attraction of the parasitoid Cotesia rubecula: chemical, behavioral, and gene-expression analysis. J Chem Ecol 27:1911–1928PubMedCrossRefGoogle Scholar
  83. Vickers CE, Gershenzon J, Lerdau MT, Loreto F (2009) A unified mechanism of action for volatile isoprenoids in plant abiotic stress. Nat Chem Biol 5:283–291PubMedCrossRefGoogle Scholar
  84. Wallis IR, Keszei A, Henery ML, Moran GF, Forrester R, Maintz J, Marsh KJ, Andrew RL, Foley WJ (2011) A chemical perspective on the evolution of variation in Eucalyptus globulus. Perspect Plant Ecol Evol Syst 13:305–318CrossRefGoogle Scholar
  85. Webb H, Lanfear R, Hamill J, Foley WJ, Külheim C (2013) The yield of essential oils in Melaleuca alternifolia (Myrtaceae) is regulated through transcript abundance of genes in the MEP pathway. PLoS One 8:e60631PubMedCentralPubMedCrossRefGoogle Scholar
  86. Wilson PG (2011) Myrtaceae. In: Kubitzki K (ed) The families and genera of vascular plants, vol 10. Springer, Berlin, pp 212–271Google Scholar
  87. Wilson P, O’Brien M, Heslewood M, Quinn C (2005) Relationships within Myrtaceae sensu lato based on a matK phylogeny. Plant Syst Evol 251:3–19CrossRefGoogle Scholar
  88. Wise ML, Savage TJ, Katahira E, Croteau R (1998) Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J Biol Chem 273:14891–14899PubMedCrossRefGoogle Scholar
  89. World-Health-Organisation (1999) d-Limonene. In Some chemicals that cause tumours of the kidney or urinary bladder in rodents and some other substances: summary of data reported and evaluation. IARC, pp 307–327Google Scholar
  90. Zhuang X, Köllner TG, Zhao N, Li G, Jiang Y, Zhu L, Ma J, Degenhardt J, Chen F (2012) Dynamic evolution of herbivore-induced sesquiterpene biosynthesis in sorghum and related grass crops. Plant J 69:70–80PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Amanda Padovan
    • 1
  • András Keszei
    • 1
  • Carsten Külheim
    • 1
  • William J. Foley
    • 1
  1. 1.Research School of BiologyAustralian National UniversityCanberraAustralia

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