Advertisement

Planta

pp 1–8 | Cite as

Terpenes and isoprenoids: a wealth of compounds for global use

  • Sarada D. TetaliEmail author
Review
  • 231 Downloads
Part of the following topical collections:
  1. Terpenes and Isoprenoids

Abstract

Main conclusion

Role of terpenes and isoprenoids has been pivotal in the survival and evolution of higher plants in various ecoregions. These products find application in the pharmaceutical, flavor fragrance, and biofuel industries.

Fitness of plants in a wide range of environmental conditions entailed (i) evolution of secondary metabolic pathways enabling utilization of photosynthate for the synthesis of a variety of biomolecules, thereby facilitating diverse eco-interactive functions, and (ii) evolution of structural features for the sequestration of such compounds away from the mainstream primary metabolism to prevent autotoxicity. This review summarizes features and applications of terpene and isoprenoid compounds, comprising the largest class of secondary metabolites. Many of these terpene and isoprenoid biomolecules happen to be high-value bioproducts. They are essential components of all living organisms that are chemically highly variant. They are constituents of primary (quinones, chlorophylls, carotenoids, steroids) as well as secondary metabolism compounds with roles in signal transduction, reproduction, communication, climatic acclimation, defense mechanisms and more. They comprise single to several hundreds of repetitive five-carbon units of isopentenyl diphosphate (IPP) and its isomer dimethylallyl diphosphate (DMAPP). In plants, there are two pathways that lead to the synthesis of terpene and isoprenoid precursors, the cytosolic mevalonic acid (MVA) pathway and the plastidic methylerythritol phosphate (MEP) pathway. The diversity of terpenoids can be attributed to differential enzyme and substrate specificities and to secondary modifications acquired by terpene synthases. The biological role of secondary metabolites has been recognized as pivotal in the survival and evolution of higher plants. Terpenes and isoprenoids find application in pharmaceutical, nutraceutical, synthetic chemistry, flavor fragrance, and possibly biofuel industries.

Notes

Acknowledgements

The author thanks the Indian Government funding agencies, DBT (BT/PR/10972/GBD/27/123/2008), UGC (37/532/2010 SR), CSIR (38(1334)/12/EMR-II/2013) and ICMR (59/48/2010/BMS/TRM) for support to her laboratory and for enabling work with medicinal and aromatic plants.

Compliance with ethical standards

Conflict of interest

The author declares no conflict of interest.

Supplementary material

425_2018_3056_MOESM1_ESM.docx (41 kb)
Supplementary material 1 (DOCX 40 kb)

References

  1. Abbas F, Ke Y, Yu R et al (2017) Volatile terpenoids: multiple functions, biosynthesis, modulation and manipulation by genetic engineering. Planta 246:803–816.  https://doi.org/10.1007/s00425-017-2749-x CrossRefPubMedGoogle Scholar
  2. Betterle N, Melis A (2018) Heterologous leader sequences in fusion constructs enhance expression of geranyl diphosphate synthase and yield of β-phellandrene production in cyanobacteria (Synechocystis). ACS Synth Biol 7(3):912–921.  https://doi.org/10.1021/acssynbio.7b00431 CrossRefPubMedGoogle Scholar
  3. Bohlmann J, Keeling CI (2008) Terpenoid biomaterials. Plant J 54:656–669.  https://doi.org/10.1111/j.1365-313x.2008.03449.x CrossRefGoogle Scholar
  4. Bracha-Drori K, Shichrur K, Lubetzky TC, Yalovsky S (2008) Functional analysis of Arabidopsis postprenylation CaaX processing enzymes and their function in subcellular protein targeting. Plant Physiol 148:119–131.  https://doi.org/10.1104/pp.108.120477 CrossRefPubMedPubMedCentralGoogle Scholar
  5. Chaves JE, Melis A (2018a) Engineering isoprene synthesis in cyanobacteria. FEBS Lett 592:2059–2069.  https://doi.org/10.1002/1873-3468.13052 CrossRefPubMedGoogle Scholar
  6. Chaves JE, Melis A (2018b) Biotechnology of cyanobacterial isoprene production. Appl Microbiol Biotechnol 102:6451–6458CrossRefGoogle Scholar
  7. Cho KS, Lim YR, Lee K et al (2017) Terpenes from forests and human health. Toxicol Res 33:97–106.  https://doi.org/10.5487/tr.2017.33.2.097 CrossRefPubMedPubMedCentralGoogle Scholar
  8. Croteau R, Kutcahn TM, Lewis NG (2000) Natural products. In: Buchanan B, Gruissem W, Jones R (eds) Biochemistry and molecular biology of plants. American Society of Plant Physiologists, Rockville, pp 1250–1318Google Scholar
  9. Englund E, Shabestary K, Hudson EP et al (2018) Cyanobacterial production of plant essential oils. Appl Microbiol Biotechnol 248:2791–2800.  https://doi.org/10.1016/j.ymben.2018.07.004 CrossRefGoogle Scholar
  10. Formighieri C, Melis A (2016) Sustainable heterologous production of terpene hydrocarbons in cyanobacteria. Photosynth Res 130:123–135CrossRefGoogle Scholar
  11. Formighieri C, Melis A (2017) Heterologous synthesis of geranyllinalool, a diterpenol plant product, in the cyanobacterium Synechocystis. Appl Microbiol Biotechnol 101:2791–2800CrossRefGoogle Scholar
  12. Formighieri C, Melis A (2018) Cyanobacterial production of plant essential oils. Planta 248:933–946CrossRefGoogle Scholar
  13. Gao Y, Honzatko RB, Peters RJ (2012) Terpenoid synthase structures: a so far incomplete view of complex catalysis. Nat Prod Rep 29:1153–1175.  https://doi.org/10.1039/c2np20059g CrossRefPubMedPubMedCentralGoogle Scholar
  14. Gershenzon J, Dudareva N (2007) The function of terpene natural products in the natural world. Nat Chem Biol 3:408–414.  https://doi.org/10.1038/nchembio.2007.5 CrossRefPubMedGoogle Scholar
  15. Hausch BJ, Lorjaroenphon Y, Cadwallader KR (2015) Flavor chemistry of lemon-lime carbonated beverages. J Agric Food Chem 63:112–119CrossRefGoogle Scholar
  16. Holstein SA, Hohl RJ (2004) Isoprenoids: remarkable diversity of form and function. Lipids 39:293–309.  https://doi.org/10.1007/s11745-004-1233-3 CrossRefPubMedGoogle Scholar
  17. Kokkiripati PK, Bhakshu LM, Marri S et al (2011) Gum resin of Boswellia serrata inhibited human monocytic (THP-1) cell activation and platelet aggregation. J Ethnopharmacol.  https://doi.org/10.1016/j.jep.2011.07.004 CrossRefPubMedGoogle Scholar
  18. Kokkiripati PK, Kamsala RV, Bashyam L et al (2013) Stem-bark of Terminalia arjuna attenuates human monocytic (THP-1) and aortic endothelial cell activation. J Ethnopharmacol 146:456–464.  https://doi.org/10.1016/j.jep.2012.12.050 CrossRefPubMedGoogle Scholar
  19. Kutyna DR, Borneman AR (2018) Heterologous production of flavour and aroma compounds in Saccharomyces cerevisiae. Genes (Basel) 9:326–341.  https://doi.org/10.3390/genes9070326 CrossRefGoogle Scholar
  20. Lauersen KJ, Wichmann J, Baier T et al (2018) Phototrophic production of heterologous diterpenoids and a hydroxy- functionalized derivative from Chlamydomonas reinhardtii. Metab Eng 49:116–127.  https://doi.org/10.1016/j.ymben.2018.07.005 CrossRefGoogle Scholar
  21. Laule O, Furholz A, Chang H-S et al (2003) Crosstalk between cytosolic and plastidial pathways of isoprenoid biosynthesis in Arabidopsis thaliana. Proc Natl Acad Sci 100:6866–6871.  https://doi.org/10.1073/pnas.1031755100 CrossRefPubMedGoogle Scholar
  22. Laurent M (2018) Vitamin E biosynthesis and its regulation in plants. Antiioxidants.  https://doi.org/10.3390/antiox7010002 CrossRefGoogle Scholar
  23. Lee C (2016) Fifty years of research and development of cosmeceuticals: a contemporary review. J Cosmet Dermatol 15:527–539.  https://doi.org/10.1111/jocd.12261 CrossRefPubMedGoogle Scholar
  24. Li L, Ma X, Zhan R et al (2017) Profiling of volatile fragrant components in a mini-core collection of mango germplasms from seven countries. PLoS One 12:1–14Google Scholar
  25. Lohr M, Schwender J, Polle JEW (2012) Isoprenoid biosynthesis in eukaryotic phototrophs: a spotlight on algae. Plant Sci 185–186:9–22.  https://doi.org/10.1016/j.plantsci.2011.07.018 CrossRefGoogle Scholar
  26. Lombard J, Moreira D (2011) Origins and early evolution of the mevalonate pathway of isoprenoid biosynthesis in the three domains of life. Mol Biol Evol 28:87–99.  https://doi.org/10.1093/molbev/msq177 CrossRefPubMedGoogle Scholar
  27. Melis A (2017) Terpene hydrocarbons production in cyanobacteria. In: Los DA (ed) Cyanobacteria: omics and manipulation. Caister Academic Press, UK, pp 187–198Google Scholar
  28. Moniodis J, Jones CG, Barbour EL et al (2015) The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum). Phytochemistry 113:79–86.  https://doi.org/10.1016/j.phytochem.2014.12.009 CrossRefPubMedGoogle Scholar
  29. Moses T, Pollier J, Thevelein JM, Goossens A (2013) Bioengineering of plant (tri) terpenoids: from metabolic engineering of plants to synthetic biology in vivo and in vitro. New Phytol 200:27–43.  https://doi.org/10.1111/nph.12325 CrossRefPubMedGoogle Scholar
  30. Niebler J, Buettner A (2015) Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography–mass spectrometry/olfactometry. Phytochemistry 109:66–75.  https://doi.org/10.1016/j.phytochem.2014.10.030 CrossRefPubMedGoogle Scholar
  31. Nolan KA, Marmur ES (2012) Over-the-counter topical skincare products: a review of the literature. J Drugs Dermatol 11:220–224PubMedGoogle Scholar
  32. Nuutinen T (2018) Medicinal properties of terpenes found in Cannabis sativa and Humulus lupulus. Eur J Med Chem 157:198–228CrossRefGoogle Scholar
  33. Paddon CJ, Westfall PJ, Pitera DJ et al (2013) High-level semi-synthetic production of the potent antimalarial artemisinin. Nature 496:528–536.  https://doi.org/10.1038/nature12051 CrossRefPubMedGoogle Scholar
  34. Pateraki I, Kanellis A (2010) Stress and developmental responses of terpenoid biosynthetic genes in Cistus creticus subsp. creticus. Plant Cell Rep 29:629–641CrossRefGoogle Scholar
  35. Pérez-Sánchez A, Barrajón-Catalán E, Herranz-López M, Micol V (2018) Nutraceuticals for skin care: a comprehensive review of human clinical studies. Nutrients 10:1–22.  https://doi.org/10.3390/nu10040403 CrossRefGoogle Scholar
  36. Phulara SC, Chaturvedi P, Gupta P (2016) Isoprenoid-based biofuels: homologous expression and heterologous expression in prokaryotes. Appl Environ Microbiol 82:5730–5740.  https://doi.org/10.1128/aem.01192-16 CrossRefPubMedPubMedCentralGoogle Scholar
  37. Pragadheesh VS, Chanotiya CS, Rastogi S, Shasany AK (2017) Scent from Jasminum grandiflorum flowers: investigation of the change in linalool enantiomers at various developmental stages using chemical and molecular methods. Phytochemistry 140:83–94.  https://doi.org/10.1016/j.phytochem.2017.04.018 CrossRefPubMedGoogle Scholar
  38. Pulido P, Perello C, Rodriguez-Concepcion M (2012) New insights into plant isoprenoid metabolism. Mol Plant 5:964–967.  https://doi.org/10.1093/mp/sss088 CrossRefPubMedGoogle Scholar
  39. Raguso RA (2016) More lessons from linalool: insights gained from a ubiquitous floral volatile. Curr Opin Plant Biol 32:31–36.  https://doi.org/10.1016/j.pbi.2016.05.007 CrossRefPubMedGoogle Scholar
  40. Rodríguez-Concepción M (2014) Plant isoprenoids: a general overview. In: Rodríguez-Concepción M (ed) Plant isoprenoids: methods and protocols, methods in molecular biology. Springer, New York, pp 1–5CrossRefGoogle Scholar
  41. Rodriguez-Concepcion M, Avalos J, Bonet ML et al (2018) A global perspective on carotenoids: metabolism, biotechnology, and benefits for nutrition and health. Prog Lipid Res 70:62–93.  https://doi.org/10.1016/j.plipres.2018.04.004 CrossRefPubMedGoogle Scholar
  42. Sathasivam R, Ki J-S (2018) A Review of the biological activities of microalgal carotenoids and their potential use in healthcare and cosmetic industries. Mar Drugs 16:26–37.  https://doi.org/10.3390/md16010026 CrossRefPubMedCentralGoogle Scholar
  43. Schwieterman ML, Colquhoun TA, Jaworski EA et al (2014) Strawberry flavor: diverse chemical compositions, a seasonal influence, and effects on sensory perception. PLoS One 9:e88446.  https://doi.org/10.1371/journal.pone.0088446 CrossRefPubMedPubMedCentralGoogle Scholar
  44. Shahidi F, de Camargo AC (2016) Tocopherols and tocotrienols in common and emerging dietary sources: occurrence, applications, and health benefits. Int J Mol Sci 17:1–29.  https://doi.org/10.3390/ijms17101745 CrossRefGoogle Scholar
  45. Sugawara Y, Hara C, Aoki T et al (2000) Odor distinctiveness between enantiomers of linalool: difference in perception and responses elicited by sensory test and forehead surface potential wave measurement. Chem Senses 25:77–84CrossRefGoogle Scholar
  46. Sun P, Schuurink RC, Caissard J et al (2016) My way: noncanonical biosynthesis pathways for plant volatiles. Trends Plant Sci 10:884–894.  https://doi.org/10.1016/j.tplants.2016.07.007 CrossRefGoogle Scholar
  47. Tholl D (2015) Biosynthesis and biological functions of terpenoids in plants. Adv Biochem Eng Biotechnol 148:63–106.  https://doi.org/10.1007/10_2014_295 CrossRefPubMedGoogle Scholar
  48. Tippmann S, Chen Y, Siewers V, Nielsen J (2013) From flavors and pharmaceuticals to advanced biofuels: production of isoprenoids in Saccharomyces cerevisiae. Biotechnol J 8:1435–1444.  https://doi.org/10.1002/biot.201300028 CrossRefPubMedGoogle Scholar
  49. Vickers CE, Williams TC, Peng B, Cherry J (2017) Recent advances in synthetic biology for engineering isoprenoid production in yeast. Curr Opin Chem Biol 40:47–56.  https://doi.org/10.1016/j.cbpa.2017.05.017 CrossRefGoogle Scholar
  50. Wagner K-H, Elmadfa I (2003) Biological relevance of terpenoids. Overview focusing on mono-, di- and tetraterpenes. Ann Nutr Metab Nutr Metab 47:95–106CrossRefGoogle Scholar
  51. Wang G, Tang W, Bidigare RR (2005) Terpenoids as therapeutic drugs and pharmaceutical agents. In: Z L (ed) Natural Products. Humana Press, Totowa, pp 197–227CrossRefGoogle Scholar
  52. Wichmann J, Baier T, Wentnagel E et al (2018) Tailored carbon partitioning for phototrophic production of (E)-α-bisabolene from the green microalga Chlamydomonas reinhardtii. Metab Eng 45:211–222CrossRefGoogle Scholar
  53. Wojtunik-kulesza KA, Targowska-duda K, Klimek K (2017) Volatile terpenoids as potential drug leads in Alzheimer’ s disease. Open Chem 15:332–343CrossRefGoogle Scholar
  54. Zhao DD, Jiang LL, Li HY et al (2016) Chemical components and pharmacological activities of terpene natural products from the genus Paeonia. Molecules 21:E1362.  https://doi.org/10.3390/molecules21101362 CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Plant Sciences, School of Life SciencesUniversity of HyderabadHyderabadIndia

Personalised recommendations