Skip to main content
SpringerLink
Log in

Monoterpenes in Essential Oils

Biosynthesis and Properties

  • Chapter
Chemicals via Higher Plant Bioengineering

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 464))

Abstract

Monoterpenes are compounds found in the essential oils extracted from many plants, including fruits, vegetables, spices and herbs. These compounds contribute to the flavor and aroma of plant from which they are extracted. Monoterpenes are acyclic, monocyclic, or bicyclic C10 compounds synthesized by monoterpene synthases using geranyl pyrophos-phate (GPP) as substrate. GPP is also the precursor in the synthesis of farnesyl pyrophos-phate (FPP) and geranyl-geranyl pyrophosphate (GGPP), two important compounds in cell metabolism of animals, plants and yeast. Monoterpene cyclases produce cyclic monoterpenes through a multistep mechanism involving a universal intermediate, a terpinyl cation which can be transformed to several compounds. Experimental studies, using animal cancer models, have demonstrated that some monoterpenes possess anticarcinogenic properties, acting at different cellular and molecular levels. From these discoveries it seems clear that monoterpenes could be considered as effective, nontoxic dietary antitumorigenic agents that hold promise as a novel class of anticancer drugs.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Alonso, W. R. and Croteau, R. Prenyl transferases and cyclases In: Methods in Plant Biochemistry. Lea, P. J., Ed.; Academic Press Ltd., London, England 1993, 239–260.

    Google Scholar 

  • Bursch, W.; Oberhammer, F.; Jirtle, R. L.; Askari, M.; Sedovu, R.; Grasl-Kraupp, B.; Purchio, A. F.; Schulte-Her-mann, R. Transforming growth factor-β1 as signal for induction of cell death by apoptosis. Br. J. Can. 1993,67,531–536

    Article  CAS  Google Scholar 

  • Casey, P. J. Protein lipidation in cell signaling. Science. 1995, 268, 221–224.

    Article  PubMed  CAS  Google Scholar 

  • Colby, S. M.; Alonso, W. R.; Katahira, E. J.; McGarvey, D. J.; Croteau, R. 4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. J. Biol. Chem. 1993, 268, 23016–23024.

    PubMed  CAS  Google Scholar 

  • Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids. Chapman & Hall, New York, 1992.

    Google Scholar 

  • Croteau, R. Biosynthesis and catabolism of monoterpenoids. Chem. Rev. 1987, 87, 929–954.

    Article  CAS  Google Scholar 

  • Croteau, R.; Purkett, P. T. Geranyl pyrophosphate synthase: Characterization of the enzyme and evidence that this chain-length specific prenyltransfarase is associated with monoterpene biosynthesis in sage (Salvia offcinalis). Arch. Biochem. Biophys. 1989, 271, 524–535.

    Article  PubMed  CAS  Google Scholar 

  • Croteau, R.; Alonso, W. R.; Koepp A. E.; Johnson, M. A. Biosynthesis of Monoterpenes. Partial purification, characterization, and mechanism of action of 1,8-cineole synthase. Arch. Biochem. Biophys. 1994, 309, 184–192.

    Article  PubMed  CAS  Google Scholar 

  • Croteau, R.; Gershenzon, J.; Wheeler, C. J.; Satterwhite, D. M. Biosynthesis of Monoterpenes. Stereochemistry of the coupled isomerization and cyclization of geranyl pyrophosphate to camphene and isocamphene monoterpenes. Arch. Biochem. Biophys. 1990, 277, 374–381.

    Article  PubMed  CAS  Google Scholar 

  • Croteau, R.; Satterwhite, D. M.; Cane, D. E, Chang C. C. Biosynthesis of Monoterpenes. Enantioselectivity in the enzymatic cyclizations of;(+)-and (-)-linalyl pyrophosphate to (+)-and (-)-bornyl pyrophosphate. J. Biol. Chem. 1986, 261, 13438–13445.

    PubMed  CAS  Google Scholar 

  • Croteau, R.; Satterwhite, D. M.; Cane, D. E.; Chang, C. C. Biosynthesis of Monoterpenes. Enantioselectivity in the enzymatic cyclizations of (+)-linalyl pyrophosphate to (+)-and (-)-pinene and (-)-camphene. J. Biol. Chem. 1988a, 263, 10063–10071.

    PubMed  CAS  Google Scholar 

  • Croteau, R.; Satterwhite, D. M.; Wheeler, C. J.; Felton, N. M. Biosynthesis of Monoterpenes. Stereochemistry of the enzymatic cyclizations of geranyl pyrophosphate to (-)-endo-fenchol. J. Biol. Chem. 1988b, 263, 15449–15453.

    PubMed  CAS  Google Scholar 

  • Croteau, R.; Satterwhite, D. M.; Wheeler, C. J.; Felton, N. M. Biosynthesis of Monoterpenes. Stereochemistry of the enzymatic cyclizations of geranyl pyrophosphate to (+)-α-pinene and (-)-β-pinene. J. Biol. Chem. 1989, 264, 2075–2080.

    PubMed  CAS  Google Scholar 

  • Croteau, R. B.; Wheeler, C. J.; Cane, D. E.; Ebert, R.; Ha, H.-J. Isotopically sensitive branching in the formation of cyclic monoterpenes: Proof that (-)-α-pinene and (-)-β-pinene are synthesized by the same monotepene cyclase via deprotonation of a common intermediate. Biochemistry 1987, 26, 5383–5389.

    Article  PubMed  CAS  Google Scholar 

  • Crowell, P. L.; Kennan, W. S.; Haag, J. D.; Ahmad, S.; Vedejs, E.; Gould, M. N. Chemoprevention of mammary carcinogenesis by hydroxylated derivatives of d-limonene. Carcinogenesis 1992,13, 1261–1264.

    Article  PubMed  CAS  Google Scholar 

  • Crowell, P. L.; Siar Ayoubi, A.; Burke, Y. D. Antitumorigenic effects of limonene and perillyl alcohol against pancreatic and breast cancer. Adv. Exp. Med. Biol. 1996, 401, 131–136.

    Article  PubMed  CAS  Google Scholar 

  • De-Oliveira, A. C.; Ribeiro-Pinto, L. F.; Otto, S. S.; Goncalves, A.; Paumgartten, F. J. Induction of liver monooxy-genases by beta-myrcene. Toxicology 1997a, 124, 135–140.

    Article  PubMed  CAS  Google Scholar 

  • De-Oliveira, A. C.; Ribeiro-Pinto, L. F.; Paumgartten, J. R. In vitro inhibition of CYP2B1 monooxygenase by beta-myrcene and other monoterpenoid compounds. Toxicol. Lett. 1997b, 92, 39–44.

    Article  PubMed  CAS  Google Scholar 

  • Dudareva, N.; Cseke, L.; Blanc, V. M.; Pichersky, E. Evolution of floral scent in Clarkia: Novel patterns of S-linalool synthase gene expression in the C. breweri flower}. The Plant Cell. 1996, 8, 1137–1148.

    PubMed  CAS  Google Scholar 

  • Eisenreich, W.; Menhard, B.; Hylands, P. J.; Zenk, J. H.; Bacher, A. Studies on the biosynthesis of taxol: The tax-ane carbon skeleton is not of mevalonoid origin. Proc. Natl. Acad. Sci. USA. 1996, 93, 6431–6436.

    Article  PubMed  CAS  Google Scholar 

  • Eisenreich, W.; Sagner, S.; Zenk, M. H.; Bacher, A. Monoterpenoid essential oils are not of mevalonoid origin. Tetrahedron Lett. 1997, 38, 3889–3892.

    Article  CAS  Google Scholar 

  • Facchini, P. J.; Chapell, J. Gene family for an elicitor induced sesquiterpene cyclase in tobacco. Proc. Natl Acad. Sci. USA. 1992, 89, 11088–11092.

    Article  PubMed  CAS  Google Scholar 

  • Gambliel, H.; Croteau, R. Pinene Cyclases I and II. Two enzymes form sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration. J. Biol. Chem. 1984, 259, 740–748.

    PubMed  CAS  Google Scholar 

  • Gelb, M. H.; Tamanoi, F.; Yokoyama, K.; Ghomashchi, F.; Esson, K.; Gould, M. N. The inhibition of protein prenyltransferases by oxygenated metabolites of limonene and perillyl alcohol. Cancer Lett. 1995, 91, 169–175.

    Article  PubMed  CAS  Google Scholar 

  • Gould, M. N. Prevention and therapy of mammary cancer by monoterpenes. J. Cell Biochem. 1995, Suppl 22, 139–144.

    Article  CAS  Google Scholar 

  • Hall, P.; Coates, P. J.; Ansari, B.; Hopwood, D. Regulation of cell number in the mammalian gastrointestinal tract: the importance of apoptosis. J. Cell Sci. 1994,107, 3569–3577.

    PubMed  CAS  Google Scholar 

  • He, L.; Mo, H.; Hadisusilo, S.; Qureshi, A. A.; Elson, C. E. Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo. J. Nutr. 1997,127, 668–674.

    PubMed  CAS  Google Scholar 

  • Hohl, R. J.; Lewis, K. Differential effects of monoterpenes and lovastatin on ras processing. J. Biol Chem. 1995, 270, 17508–17512.

    Article  PubMed  CAS  Google Scholar 

  • Irving, R. S.; Adams, R. P. Genetic and biosynthetic relationships of monoterpenes. In: Terpenoids: Structure, biogenesis, and distribution. Runeckles, V. C.; Mabry, T. J. Eds. Academic Press. New York and London. 1973,187–214.

    Google Scholar 

  • Jackson, J. H.; Cochrane, C.G.; Bourne, J. R.; Solski, P. A.; Buss, J. E.; Der, C. J. Farnesol modification of Kir-sten-ras exon 4B protein is essential for transformation. Proc. Natl. Acad. Sci. USA. 1990, 87, 3042–3046.

    Article  PubMed  CAS  Google Scholar 

  • Jirtle, R.L.; Haag, J. D.; Ariazi, E. A.; Gould, M. N. Increased mannose 6-phosphate/insulin-like growth factor II receptor and transforming growth factor β 1 levels during monoterpene-induced regression of mammary tumors. Can. Res. 1993, 53, 3849–3852.

    CAS  Google Scholar 

  • Juven, B. J.; Kanner, J.; Schved, F.; Weisslowicz, H. Factors that interact with the antibacterial action of thyme essential oil and its active constituents. J. Appl. Bacteriol. 1994, 76, 626–631.

    Article  PubMed  CAS  Google Scholar 

  • Karlson, J.; Borg-Karlson, A. K.; Unelius, R.; Shoshan, M. C; Wilking, N.; Ringborg, U.; Linder, S. Inhibition of tumor cell growth by monoterpenes in vitro: Evidence of a Ras-independent mechanism of action. Anti-cancer Drugs. 1996, 7,422–429.

    Article  PubMed  CAS  Google Scholar 

  • Lange, B. M.; Wildung, M. R.; McCaskill, D.; Croteau, R. A family of tansketolases that directs isoprenoid biosynthesis via a mevalonate independent pathway. Proc. Natl. Acad. Sci. 1998, 95, 2100–2104.

    Article  PubMed  CAS  Google Scholar 

  • Lichtenthaler, R.; 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.

    Article  PubMed  CAS  Google Scholar 

  • Lois, L. M.; Campos, N.; Putra, S. R.; Danielsen, K.; Rohmer, M.; Boronat, A. Cloning and characterization of a gene from Escherichia coli encoding a transketolase-like enzyme that catalyzes the synthesis of d-1-de-oxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin, and pyridoxol biosynthesis. Proc. Natl Acad. Sci. USA. 1998, 95, 2105–2110.

    Article  PubMed  CAS  Google Scholar 

  • Luckner, M. Secondary metabolism in microorganisms, plants, and animals. Second Edition. Springer-Verlag, Berlin, Germany 1984, 35–37, 41-42, 199-210.

    Google Scholar 

  • Mandel, A.; Feldmann, K.; Herrera-Estrella, L.; Rocha-Sosa, M.; Le ón, P. Clal, a novel gene required for chloro-plast development, is highly conserved in evolution. Plant J. 1996, 9, 649–658.

    Article  PubMed  CAS  Google Scholar 

  • Mau, C. J. D.; West, C. A. Cloning of casbene synthase cDNA: Evidence for conserved structural features among terpenoid cyclases in plants. Proc. Natl. Acad. Sci. USA. 1994, 91, 8497–8501.

    Article  PubMed  CAS  Google Scholar 

  • Marion, M. J. P.; Audrin, A.; Miagnial, L.; Brevard, H. Spices and their extracts: Utilization, selection, quality control and new developments. In: Spices, Herbs and Edible Fungi;, Charalambous, G., Ed.; Elsevier. Science B.V. Amsterdam, The Netherlands 1994, 71–95.

    Google Scholar 

  • McGeady, P.; Croteau, R. Isolation and characterization of an active-site peptide from a monoterpene cyclase labeled with a mechanism-based inhibitor. Arch. Biochem. Biophys. 1995, 317, 149–155.

    Article  PubMed  CAS  Google Scholar 

  • Meireles, M. A. A.; Nikolov, Z. L. Extraction and fractionation of essential oils with liquid carbon dioxide. In: Spices, Herbs and Edible Fungi; Charalambous, G., Ed.; Elsevier Science B.V. Amsterdam, The Netherlands 1994, 1–70.

    Google Scholar 

  • Mills, J. J.; Chari, R. S.; Boyer, I. J.; Gould, M. N.; Jirtle, R. L. Induction of apoptosis in liver tumors by the monoterpene perillyl alcohol. Cancer Res. 1995, 55, 979–983.

    PubMed  CAS  Google Scholar 

  • Moyler, D. A. Spices-Recent Advances. In: Spices, Herbs and Edible Fungi; Charalambous, G., Ed.; Elsevier Science BV. Amsterdam, The Netherlands. 1994, 1–70.

    Google Scholar 

  • Moyler, D. A.; Browing, R. M.; Stephens, M. A. CO2 extraction of esential oils: Part V, nutmeg and mace oils. In: Spices, Herbs and Edible Fungi; Charalambous, G., Ed.; Elsevier Science BV, Amsterdam, The Netherlands 1994, 145–170.

    Google Scholar 

  • Müller-Riebau, F. J.; Berger, B. M.; Yegen, O.; Cakir, C. Seasonal variations in the chemical compositions of essential oils of selected aromatic plants growing wild in Turkey. J. Agric. Food Chem. 1997, 45, 4821–4825.

    Article  Google Scholar 

  • Nakatani, N. Antioxidative and antimicrobial constituents of herbs and spices. In: Spices, Herbs and Edible Fungi; Charalambous, G., Ed.; Elsevier Science B.V. Amsterdam, The Netherlands 1994, 251–271.

    Google Scholar 

  • Ouattara, B; Simard, R. E.; Holley, R. A.; Piette, G. J.; Begin, A. Antibacterial activity of selected fatty acids and essential oils against six meat spoilage organisms. Int. J. Food Microbiol. 1997, 37, 155–162.

    Article  PubMed  CAS  Google Scholar 

  • Patinaik, S.; Subramanyam, V. R.; Bapaji, M.; Kole, C. R. Antibacterial and antifungal activity of aromatic constituents of essential oils. Microbios. 1997, 89, 39–46.

    Google Scholar 

  • Pichersky, E.; Lewinsohn, E.; Croteau, R. Purification and characterization of S-linalool synthase, an enzyme involved in the production of floral scent in Clarkia breweri. Arch. Biochem. Biophys. 1995, 316, 803–807.

    Article  PubMed  CAS  Google Scholar 

  • Rajaonarivony, J. I. M.; Gershenzon, J.; Croteau, R. Characterization and mechanism of (4S)-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita). Arch. Biochem. Biophys. 1992, 296,49–57.

    Article  PubMed  CAS  Google Scholar 

  • Reddy, B. S.; Wang, C. X.; Samaha, H.; Lubet, R.; Steele, V. E.; Kelloff, G. J.; Rao, C. V. Chemoprevention of colon carcinogenesis by dietary perillyl alcohol. Cancer Res. 1997, 57, 420–425.

    PubMed  CAS  Google Scholar 

  • Rohmer, M.; Knani, M.; Simonin, P.; Sutter, B.; Sahm, H. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J. 1993. 295, 517–524.

    Google Scholar 

  • Russin, W. A.; Hoesly, J. D.; Elson, C. E.; Tanner, M. A.; Gould, M. N. Inhibition of rat mammary carcinogenesis by monoterpenoids. Carcinogenesis. 1989,10, 2161–2164.

    Article  PubMed  CAS  Google Scholar 

  • Sharkey, T. D. Isoprene synthesis by plants and animals. Endeavour. 1996, 20,74–78.

    Article  PubMed  CAS  Google Scholar 

  • Shi, W.; Gould, M. N. Induction of differentiation in neuro-2A cells by the monoterpene perillyl alcohol. Cancer Lett. 1995, 95, 1–6.

    Article  PubMed  CAS  Google Scholar 

  • Tantaoui-Elaraki; A.; Beraoud L. Inhibition of growth and aflatoxin production in Aspergillus parasiticus by essential oils of selected plant materials. J. Environ. Pathol. Toxicol Oncol. 1994, 13, 67–72.

    PubMed  CAS  Google Scholar 

  • Tateo, R.; Ferrillo, A.; Orlandi, A. 1994. Analysis of natural flavourings: Problems and actual methods. In: Spices, Herbs and Edible Fungi; Charalambous, G., Ed.; Elsevier Science, B.V. Amsterdam, The Netherlands 1994,97–129.

    Google Scholar 

  • Wagschal, K. C.; Pyun, H.-J.; Coates, R. M.; Croteau, R. Monoterpene biosynthesis: Isotope effects associated with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis). Arch. Biochem. Biophys. 1994, 308, 477–487.

    Article  PubMed  Google Scholar 

  • Wrana, J. L.; Attisano, L.; Wieser, R.; Ventura, F.; Massagué, J. Mechanism of activation of the TGF-β receptor. Nature (Lond). 1994, 370, 341–347.

    Article  CAS  Google Scholar 

  • Yuba, A.; Yazaki, K.; Tabata, M.; Honda, G.; Croteau, R. cDNA cloning, characterization, and functional expression of 4S-(-)-limonene synthase from Perilla frutescens. Arch. Biochem. Biophys. 1996, 332, 280–287.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departamento de Bioquímica Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, México,, D.F. 04510, México

    Herminia Loza-Tavera

Authors
  1. Herminia Loza-Tavera
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Memorial University of Newfoundland, St. John, Newfoundland, Canada

    Fereidoon Shahidi

  2. POS Pilot Plant Corporation, Saskatoon, Saskatchewan, Canada

    Paul Kolodziejczyk

  3. University of California, Davis, California, USA

    John R. Whitaker

  4. Institute of Biotechnology-UNAM, Cuernavaca, Morelos, Mexico

    Agustin Lopez Munguia

  5. USDA/ARS, Albany, California, USA

    Glenn Fuller

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media New York

About this chapter

Cite this chapter

Loza-Tavera, H. (1999). Monoterpenes in Essential Oils. In: Shahidi, F., Kolodziejczyk, P., Whitaker, J.R., Munguia, A.L., Fuller, G. (eds) Chemicals via Higher Plant Bioengineering. Advances in Experimental Medicine and Biology, vol 464. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4729-7_5

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-4729-7_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7143-4

  • Online ISBN: 978-1-4615-4729-7

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation