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Plant Toxins pp 243-261 | Cite as

Plant Alkaloids: Main Features, Toxicity, and Mechanisms of Action

  • Hélio Nitta Matsuura
  • Arthur Germano Fett-NetoEmail author
Reference work entry
Part of the Toxinology book series (TOXI)

Abstract

Alkaloids are one of the largest groups of plant secondary metabolites, being present in several economically relevant plant families. Alkaloids encompass neuroactive molecules, such as caffeine and nicotine, as well as life-saving medicines including emetine used to fight oral intoxication and the antitumorals vincristine and vinblastine. Alkaloids can act as defense compounds in plants, being efficient against pathogens and predators due to their toxicity. Fast perception of aggressors and unfavorable environmental conditions, followed by efficient and specific signal transduction for triggering alkaloid accumulation, are key steps in successful plant protection. Toxic effects, in general, depend on specific dosage, exposure time, and individual characteristics, such as sensitivity, site of action, and developmental stage. At times, toxicity effects can be both harmful and beneficial depending on the ecological or pharmacological context. Different strategies are used to study alkaloid metabolism and accumulation. An efficient approach is to monitor gene expression, enzyme activities, and concentration of precursors and of the alkaloid itself during controlled attacks of pathogens and herbivores or upon the simulation of their presence through physical or chemical stimulation. Detailed understanding of alkaloid biosynthesis and mechanisms of action is essential to improve production of alkaloids of interest, to discover new bioactive molecules, and to sustainably exploit them against targets of interest, such as herbivores, pathogens, cancer cells, or unwanted physiological conditions.

Keywords

Alkaloid Antioxidant Antitumoral Herbivory Pathogen 

Notes

Acknowledgments

This work was elaborated with the support of the Brazilian agencies: National Council for Scientific and Technological Development (CNPq), Coordination for the Improvement of Higher Education Personnel (CAPES), and Rio Grande do Sul State Foundation for Research Support (FAPERGS).

References

  1. Ahsan H, Reagan-Shaw S, Eggert DM, Tan TC, Afaq F, Mukhtar H, Ahmad N. Protective effect of sanguinarine on ultraviolet B-mediated damages in SKH-1 hairless mouse skin: implications for prevention of skin cancer. Photochem Photobiol. 2007;83:986–93.CrossRefPubMedGoogle Scholar
  2. Apostolova N, Victor VM. Molecular strategies for targeting antioxidants to mitochondria: therapeutic implications. Antioxid Redox Signal. 2015;22:686–729.CrossRefPubMedPubMedCentralGoogle Scholar
  3. Beaudoin GAW, Facchini PJ. Benzylisoquinoline alkaloid biosynthesis in opium poppy. Planta. 2014;240:19–32.CrossRefPubMedGoogle Scholar
  4. Brandenburg A, Dell’Olivo A, Bshary R, Kuhlemeier C. The sweetest thing: advances in nectar research. Curr Opin Plant Biol. 2009;12:486–90.CrossRefPubMedGoogle Scholar
  5. Casikar V, Mujica E, Mongelli M, Aliaga J, Lopez N, Smith C, Bartholomew F. Does chewing coca leaves influence physiology at high altitude? Ind J Clin Biochem. 2010;25:311–4.CrossRefGoogle Scholar
  6. Courdavault V, Papon N, Clastre M, Giglioli-Guivarc N, St-Pierre B, Burlat V. A look inside an alkaloid multisite plant: the Catharanthus logistics. Curr Opin Plant Biol. 2014;19:43–50.CrossRefPubMedGoogle Scholar
  7. Croteau R, Kutchan TM, Lewis NG. Natural products (secondary metabolites). In: Buchanan B, Gruissem W, Jones R, editors. Biochemistry and molecular biology of plants. Rockville: American Society of Plant Physiologists; 2000.Google Scholar
  8. Cushnie TPT, Cushnie B, Lamb AJ. Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities. Int J Antimicrob. 2014;44:377–86.CrossRefGoogle Scholar
  9. Dewey RE, Xie J. Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry. 2014;94:10–27.CrossRefGoogle Scholar
  10. Eisner T. For love of insects. Cambridge: Harvard University Press; 2003.Google Scholar
  11. Evans SR, Hofmann A. Planta de los dioses. Mexico: Fondo de Cultura Económica; 2006.Google Scholar
  12. Green BT, Lee ST, Panter KE, Brown DR. Piperidine alkaloids: human and food animal teratogens. Food Chem Toxicol. 2012;50:2049–55.CrossRefPubMedGoogle Scholar
  13. Hagel JM, Facchini PJ. Benzylisoquinoline alkaloid metabolism: a century of discovery and a brave new world. Plant Cell Physiol. 2013;54:647–72.CrossRefPubMedGoogle Scholar
  14. Han MA, Woo SM, Min K-J, Kim S, Park J-W, Kim DE, Kim SH, Choi YH, Kwon TK. 6-Shogaol enhances renal carcinoma Caki cells to TRAIL-induced apoptosis through reactive oxygen species-mediated cytochrome c release and down-regulation of c-FLIP(L) expression. Chem-Biol Interact. 2015;228:69–78.CrossRefPubMedGoogle Scholar
  15. Hantak MM, Grant T, Reinsch S, Mcginnity D, Loring M, Toyooka N, Saporito RA. Dietary alkaloid sequestration in a poison frog: an experimental test of alkaloid uptake in Melanophryniscus stelzneri (Bufonidae). J Chem Ecol. 2013;39:1400–6.CrossRefPubMedGoogle Scholar
  16. Harborne JB. Introduction to ecological biochemistry. London: Elsevier Academic Press; 1993.Google Scholar
  17. Hartmann T. From waste products to ecochemicals: fifty years research of plant secondary metabolism. Phytochemistry. 2007;68:2831–46.CrossRefPubMedGoogle Scholar
  18. Irwin RE, Cook D, Richardson LL, Manson JS, Gardner DR. Secondary compounds in floral rewards of toxic rangeland plants: impacts on pollinators. J Agric Food Chem. 2014;62:7335–44.CrossRefPubMedGoogle Scholar
  19. Kautz S, Trisel JA, Ballhorn DJ. Jasmonic acid enhances plant cyanogenesis and resistance to herbivory in Lima bean. J Chem Ecol. 2014;40:1186–96.CrossRefPubMedGoogle Scholar
  20. Kerrigan S, Lindsey T. Fatal caffeine overdose: two case reports. Forensic Sci Int. 2005;153:67–9.CrossRefPubMedGoogle Scholar
  21. Koleva II, van Beek TA, Soffers AEMF, Dusemund B, Rietjens IMC. Alkaloids in the human food chain – natural occurrence and possible adverse effects. Mol Nutr Food Res. 2012;56:30–52.CrossRefPubMedGoogle Scholar
  22. Laue P, Bährs H, Chakrabarti S, Steinberg CEW. Natural xenobiotics to prevent cyanobacterial and algal growth in freshwater: contrasting efficacy of tannic acid, gallic acid, and gramine. Chemosphere. 2014;104:212–20.CrossRefPubMedGoogle Scholar
  23. Lee ST, Welch KD, Panter KE, Gardner DR, Garrossian M, Chang CT. Cyclopamine: from cyclops lambs to cancer treatment. J Agric Food Chem. 2014;62:7355–62.CrossRefPubMedGoogle Scholar
  24. Machowinski A, Krämer H, Hort W, Mayser P. Pityriacitrin – a potent UV filter produced by Malassezia furfur and its effect on human skin microflora. Mycoses. 2006;49:388–92.CrossRefPubMedGoogle Scholar
  25. Matsuura HN, Fett-Neto AG. The major indole alkaloid N, β-d-glucopyranosyl vincosamide from leaves of Psychotria leiocarpa Cham. & Schltdl. is not an antifeedant but shows broad antioxidant activity. Nat Prod Res. 2013;27:402–11.CrossRefPubMedGoogle Scholar
  26. Matsuura HN, Rau MR, Fett-Neto AG. Oxidative stress and production of bioactive monoterpene indole alkaloids: biotechnological implications. Biotechnol Lett. 2014;36:191–200.CrossRefPubMedGoogle Scholar
  27. Mehrotra S, Goel MK, Srivastava V, Rahman LU. Hairy root biotechnology of Rauwolfia serpentina: a potent approach for the production of pharmaceutically important terpenoid indole alkaloids. Biotechnol Lett. 2015;37:253–63.CrossRefPubMedGoogle Scholar
  28. Mithöfer A, Boland W. Plant defense against herbivores: chemical aspects. Annu Rev Plant Biol. 2012;63:431–50.CrossRefPubMedGoogle Scholar
  29. Mohsenikia M, Alizadeh AM, Khodayari S, Khodayari H, Aminkouhpayeh S, Karimi A, Zamani M, Azizian S, Mohagheghi MA. The protective and therapeutic effects of alpha-solanine on mice breast cancer. Eur J Pharmacol. 2013;718:1–9.CrossRefPubMedGoogle Scholar
  30. Nascimento NC, Fett-Neto AG. Plant secondary metabolism and challenges in modifying its operation: an overview. In: Fett-Neto AG, editor. Plant secondary metabolism: methods and applications, Methods in molecular biology series, vol. 643. New York: Humana Press; 2010.Google Scholar
  31. Okada K, Abe H, Arimura G. Jasmonates induce both defense responses and communication in monocotyledonous and dicotyledonous plants. Plant Cell Physiol. 2015;56:16–27.CrossRefPubMedGoogle Scholar
  32. Paranhos JT, Fragoso V, Henriques AT, Ferreira AG, Fett-Neto AG. Regeneration of Psychotria umbellata and production of the analgesic indole alkaloid umbellatine. Tree Physiol. 2005;25:251–5.CrossRefPubMedGoogle Scholar
  33. Pasquali G, Porto DD, Fett-Neto AG. Metabolic engineering of cell cultures versus whole-plant complexity in the production of bioactive monoterpene indole alkaloids: recent progress related to old dilemma. J Biosci Bioeng. 2006;101:287–96.CrossRefPubMedGoogle Scholar
  34. Porto DD, Matsuura HN, Vargas LRB, Henriques AT, Fett-Neto AG. Shoot accumulation kinetics and effects on herbivores of the wound-induced antioxidant indole alkaloid brachycerine of Psychotria brachyceras. Nat Prod Commun. 2014;9:629–32.PubMedGoogle Scholar
  35. Roepke J, Salim V, Wu M, Thamm AMK, Murata J, Ploss K, Boland W, DeLuca V. Vinca drug components accumulate exclusively in leaf exudates of Madagascar periwinkle. Proc Natl Acad Sci U S A. 2010;107:15287–92.CrossRefPubMedPubMedCentralGoogle Scholar
  36. Rostás M, Cripps MG, Silcock P. Aboveground endophyte affects root volatile emission and host plant selection of a belowground insect. Oecologia. 2015;177:487–97.CrossRefPubMedGoogle Scholar
  37. Saporito RA, Donnelly MA, Spande TF, Garraffo HM. A review of chemical ecology in poison frogs. Chemoecology. 2012;22:159–68.CrossRefGoogle Scholar
  38. Senchina DS, Hallam JE, Kohut ML, Nguyen NA, Perera MAN. Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners. Exerc Immunol Rev. 2014;20:68–93.PubMedGoogle Scholar
  39. Shimshoni JA, Mulder P, Bouznach A, Edery N, Pasval I, Barel S, Khaliq MA, Perl S. Heliotropium europaeum poisoning in cattle and of its pyrrolizidine alkaloid profile. J Agric Food Chem. 2015;63:1664–72.CrossRefPubMedGoogle Scholar
  40. Todd AT, Liu E, Polvi SL, Pammett RT, Page JE. A functional genomics screen identifies diverse transcription factors that regulate alkaloid biosynthesis in Nicotiana benthamiana. Plant J. 2010;62:589–600.CrossRefPubMedGoogle Scholar
  41. Vilariño MP, Ravetta DA. Tolerance to herbivory in lupin genotypes with different alkaloid concentration: interspecific differences between Lupinus albus L. and L. angustifolius L. Environ Exp Bot. 2008;63:130–6.CrossRefGoogle Scholar
  42. Wang X, Bennetzen JL. Current status and prospects for the study of Nicotiana genomics, genetics, and nicotine biosynthesis genes. Mol Genet Genomics. 2015;290:11–21.CrossRefPubMedGoogle Scholar
  43. Wasternack C, Hause B. Jasmonates: biosynthesis, perception, signal transduction and action in plant stress response, growth and development. An update to the 2007 review in Annals of Botany. Ann Bot. 2013;111:1021–58.CrossRefPubMedPubMedCentralGoogle Scholar
  44. Wilson CR, Sauer J, Hooser SB. Taxines: a review of the mechanism and toxicity of yew (Taxus spp.) alkaloids. Toxicon. 2001;39:175–85.CrossRefPubMedGoogle Scholar
  45. Wink M, Twardowski T. Allelochemical properties of alkaloids: effects on plants, bacteria and protein biosynthesis. In: Rizvi SJH, Rizvi V, editors. Allelopathy: basic and applied aspects. London: Chapman & Hall; 1992.Google Scholar
  46. Wright GA, Baker DD, Palmer MJ, Stabler D, Mustard JA, Power EF, Borland AM, Stevenson PC. Caffeine in floral nectar enhances a pollinator’s memory of reward. Science. 2013;339:1202–4.CrossRefPubMedPubMedCentralGoogle Scholar
  47. Yamashoji S, Matsuda T. Synergistic cytotoxicity induced by α-solanine and α-chaconine. Food Chem. 2013;141:669–74.CrossRefPubMedGoogle Scholar
  48. Yang L, Stöckigt J. Trends for diverse production strategies of plant medicinal alkaloids. Nat Prod Rep. 2010;27:1469–79.CrossRefPubMedGoogle Scholar
  49. Zhang X, Kuča K, Dohnal V, Dohnalová L, Wu Q, Wu C. Military potential of biological toxins. J Appl Biomed. 2014;12:63–77.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  • Hélio Nitta Matsuura
    • 1
  • Arthur Germano Fett-Neto
    • 1
    Email author
  1. 1.Plant Physiology Laboratory, Center for Biotechnology and Department of BotanyFederal University of Rio Grande do Sul (UFRGS)Porto AlegreBrazil

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