Plant toxins: alkaloids and their toxicities

Authors

  • Zaman Munirah Adibah Kamarul Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.
  • Azzeme Azzreena Mohamad Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia.

DOI:

https://doi.org/10.30574/gscbps.2019.6.2.0003

Keywords:

Plant toxins, Pyrrolizidine alkaloids, Tropane alkaloids, Piperidine alkaloids, Indolizidine alkaloids

Abstract

Since ancient civilization, plants have been utilized in many aspects of life, especially in medicinal purposes due to the presence of distinctive secondary metabolites like alkaloids, phenolics and terpenoids. Among them, alkaloids represent a large group of secondary metabolites that have basic properties and comprise nitrogen atom within the heterocyclic ring. Plant synthesizes alkaloids to maintain their survivability under unfavorable conditions. Over 3000 years, indigenous people have been used alkaloid-containing plant extracts to treat several ailments such as fever, snakebite and insanity. However, despite significant benefits to humans and pharmaceutical industries, some of the plant alkaloids are categorized as main plant toxins due to their enormous structural diversity and various modes of actions. Humans and animals can be exposed to toxic alkaloids either through inhalation, swallowing or by direct contact, therefore leads to the specific mechanism that involves receptors, transporters, enzymes and genetic materials at specific cells and tissues, hence may cause hepatotoxic effects and musculoskeletal deformities. This review focuses on some of the plant alkaloids such as pyrrolizidine, tropane, piperidine and indolizidine, which can give various side effects on humans and animals such as itching, nausea, vomiting, mild gastrointestinal perturbation, psychosis, paralysis, teratogenicity, arrhythmias and sudden death.

Metrics

Metrics Loading ...

References

Cushnie TT, Cushnie B and Lamb AJ. (2014). Alkaloids: an overview of their antibacterial, antibiotic-enhancing and antivirulence activities. International Journal of Antimicrobial Agents, 44(5), 377-386.

Kittakoop P, Mahidol C and Ruchirawat, S. (2014). Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation. Current Topics in Medicinal Chemistry, 14(2), 239-252.

Shi QIU, Hui SUN, Zhang AH, Hong-Ying XU, Guang-Li YAN, Ying HAN and Xi-Jun WANG. (2014). Natural alkaloids: basic aspects, biological roles, and future perspectives. Chinese Journal of Natural Medicines, 12(6), 401-406.

Vanderplanck M and Glauser G. (2018). Integration of non-targeted metabolomics and automated determination of elemental compositions for comprehensive alkaloid profiling in plants. Phytochemistry, 154, 1-9.

Ng YP, Or TCT and Ip NY. (2015). Plant alkaloids as drug leads for Alzheimer's disease. Neurochemistry International, 89, 260-270.

Robertson LP, Hall CR, Forster PI and Carroll AR. (2018). Alkaloid diversity in the leaves of Australian Flindersia (Rutaceae) species driven by adaptation to aridity. Phytochemistry, 152, 71-81.

Dias DA, Urban S and Roessner U. (2012). A historical overview of natural products in drug discovery. Metabolites, 2(2), 303-336.

Beaudoin GA and Facchini PJ. (2014). Benzylisoquinoline alkaloid biosynthesis in opium poppy. Planta, 240(1), 19-32.

Wadood A, Ghufran M, Jamal SB, Naeem M, Khan A and Ghaffar R. (2013). Phytochemical analysis of medicinal plants occurring in local area of Mardan. Biochemistry and Analytical Biochemistry, 2(4), 1-4.

Hamid HA, Ramli ANM and Yusoff MM. (2017). Indole alkaloids from plants as potential leads for antidepressant drugs: a mini review. Frontiers in Pharmacology, 8, 1-7.

Lu JJ, Bao JL, Chen XP, Huang M and Wang YT. (2012). Alkaloids isolated from natural herbs as the anticancer agents. Evidence-based Complementary and Alternative Medicine, 2012, 1-12.

Kurmukov AG. (2013). Phytochemistry of Medicinal Plants. In Medicinal Plants of Central Asia: Uzbekistan and Kyrgyzstan. Springer: New York, 13-14.

Sekhar CJ, Sandhya S, Ravindran V, Banji D, Sudhakar K and Chaitanya RSNAKK. (2012). Plant toxins-useful and harmful effects. Hygeia Journal of Drug and Medicine, 4(1), 79-90.

Perviz S, Khan H and Pervaiz A. (2016). Plant alkaloids as an emerging therapeutic alternative for the treatment of depression. Frontiers in Pharmacology, 7, 1-7.

Matsuura HN and Fett-Neto AG. (2015). Plant alkaloids: main features, toxicity, and mechanisms of action. In Plant Toxins. Springer Netherlands, 1-15.

Waller GR and Nowacki EK. (1978). The role of alkaloids in plants. In: Alkaloid biology and metabolism in plants. Springer: Boston, 143-181

Mazid M, Khan TA, and Mohammad F. (2011). Role of secondary metabolites in defense mechanisms of plants. Biology and Medicine, 3, 232-249.

Muzquiz M, de la Cuadra C, Cuadrado C, Burbano C and Calvo, R. (1994). Herbicide-like effect of Lupinus alkaloids. Industrial Crops and Products, 2(4), 273-280.

Patel K, Gadewar M, Tripathi R, Prasad SK and Patel DK. (2012). A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid “Harmine”. Asian Pacific Journal of Tropical Biomedicine, 2(8), 660-664.

Mohan K, Jeyachandran R and Deepa (2012). Alkaloids as anticancer agents. Annals of Phytomedicine, 1, 46 -53.

Moudi M, Go R, Yien CYS, and Nazre M. (2013). Vinca alkaloids. International Journal of Preventive Medicine, 4, 1231.

Isah T. (2016). Anticancer alkaloids from trees: Development into drugs. Pharmacognosy Reviews, 10(20), 90-99.

Saxena M, Saxena J, Nema R, Singh D, and Gupta A. (2013). Phytochemistry of medicinal plants. Journal of Pharmacognosy and Phytochemistry. 1, 168-182.

Cortinovis C and Caloni F. (2015). Alkaloid-containing plants poisonous to cattle and horses in Europe. Toxins, 7(12), 5301-5307.

Diaz GJ. (2015). Toxicosis by plant alkaloids in humans and animals in Colombia. Toxins, 7(12), 5408-5416.

Patel S, Nag MK, Daharwal SJ, Singh MR and Singh D. (2013). Plant Toxins: An Overview. Research Journal of Pharmacology and Pharmacodynamics (RJPPD), 5, 283-288.

Griffin CT, Danaher M, Elliott CT, Kennedy DG and Furey A. (2013). Detection of pyrrolizidine alkaloids in commercial honey using liquid chromatography–ion trap mass spectrometry. Food Chemistry, 136(3-4), 1577-1583.

Neuman MG and Steenkamp V. (2009). Toxicity profile of pyrrolizidine alkaloid-containing medicinal plants: Emphasis on Senecio species. International Journal of Biomedical and Pahrmaceutical Sciences, 3, 104-108.

Chen T, Mei N and Fu PP. (2010). Genotoxicity of pyrrolizidine alkaloids. Journal of Applied Toxicology, 30(3), 183-196.

Wiedenfeld H. (2011). Plants containing pyrrolizidine alkaloids: toxicity and problems. Food Additives and Contaminants: Part A, 28(3), 282-292.

Seremet OC, Olaru OT, Gutu CM, Nitulescu GM, Ilie M, Negres S, Zbarcea CE, Purdel CN, Spandidos DA, Tsatsakis AM, Coleman MD, Margina DM. (2018). Toxicity research of certain plant extracts containing pyrrolizidine alkaloids using alternative invertebrates models. Molecular Medicine Reports, 17(6), 7757-7763.

Fu PP, Xia Q, Lin G, Chou MW. (2004). Pyrrolizidine alkaloids – genotoxicity, metabolism, enzymes, metabolic activation and mechanisms. Drug Metabolism Reviews, 36(1), 1-55.

Pfister JA, Molyneux RJ, Baker DC. (1992). Pyrrolizidine alkaloid content of houndstongue (Cynoglossum officinale L.). Journal of Range Management, 45(3), 254–256.

Panter KE, Gardner DR, Lee ST, Pfister JA, Ralphs MH, Stegelmeier BL, James LF. (2012). Important poisonous plants of the United States. In: Gupta RC (Eds), Veterinary Toxicology: Basic and Clinical Principles. Elsevier Inc, San Diego, 1021-1079

Crews C and Anderson WAC. (2009). Detection of ragwort alkaloids in toxic hay by liquid chromatography/time-of-flight mass spectrometry. Veterinary Record, 165(19), 568–569.

Araújo LU, Reis PG, Barbosa LCO, Saúde-Guimarães DA, Grabe-Guimarães S, Mosqueira VCF, Carneiro CM, Silva-Barcellos NM. (2012). In vivo wound healing effects of Symphytum officinale L. leaves extract in different topical formulations. Pharmazie, 67(4), 355–360.

Arcella D and Altieri A. (2018). Human acute exposure assessment to tropane alkaloids. EFSA Journal, 16(2), 5160-5184.

Alexander J. (2008). Tropane alkaloids (from Datura sp.) as undesirable substances in animal feed. EFSA Journal, 691(8), 1-55.

Springob K and Kutchan TM. (2009). Introduction to the different classes of natural products. In Plant-Derived Natural Products. Springer, New York, 3-50

Adamse P, Van Egmond HP, Noordam MY, Mulder PPJ and De Nijs M. (2014). Tropane alkaloids in food: poisoning incidents. Quality Assurance and Safety of Crops and Foods, 6(1), 15-24.

Adamse P and Van Egmond HP. (2010). Tropane alkaloids in food. RIKILT-Institute of Food Safety: Netherland, 1-24.

Chan TY. (2017). Worldwide occurrence and investigations of contamination of herbal medicines by tropane alkaloids. Toxins, 9(9), 284-293.

Binev R, Valchev I and Nikolov J. (2006). Clinical and pathological studies on intoxication in horses from freshly cut Jimson weed (Datura stramonium)-contaminated maize intended for ensiling: clinical communication. Journal of the South African Veterinary Association, 77(4), 215-219.

Soler-Rodríguez F, Martín A, García-Cambero JP, Oropesa AL and Pérez-López M. (2006). Datura stramonium poisoning in horses: a risk factor for colic. Veterinary Record. 158(4), 132-133.

Bofill FX, Bofill J, Such G, Piqué E and Guitart R. (2007). Two cases of corn contamination poisoning with Datura stramonium in cattle. Toxicology Journal, 24(1), 56-58.

Mulder PP, Nijs M, Castellari M, Hortos M, MacDonald S, Crews C, Hajslova J and Stranska M. (2016). Occurrence of tropane alkaloids in food. EFSA Supporting Publications, 13(12), 1140-1340.

Koleva II, van Beek TA, Soffers AE, Dusemund B and Rietjens IM. (2012). Alkaloids in the human food chain–natural occurrence and possible adverse effects. Molecular Nutrition and Food Research, 56(1), 30-52.

Hotti H and Rischer H. (2017). The killer of Socrates: coniine and related alkaloids in the plant kingdom. Molecules, 22(11), 1962-1985.

Green BT, Lee ST, Panter KE and Brown DR. (2012). Piperidine alkaloids: human and food animal teratogens. Food and chemical toxicology, 50(6), 2049-2055.

Fernández-Alonso JL, Bonilla AG and Idrobo JM. (2007). The plants as legal evidence. Development of forensic botany in Colombia. Journal of the Colombian Academy of Exact, Physical and Natural Sciences, 31, 181-198.

Cramer L, Ernst L, Lubienski M, Papke U, Schiebel HM, Jerz G and Beuerle T. (2015). Structural and quantitative analysis of Equisetum alkaloids. Phytochemistry, 116, 269-282.

da Silva VDA, da Silva AMM, e Silva JHC and Costa SL. (2018). Neurotoxicity of Prosopis juliflora: from Natural Poisoning to Mechanism of Action of Its Piperidine Alkaloids. Neurotoxicity Research, 34(4), 878-888.

Wu C, Feng K, Lu D, Yan D, Han T and Zhao B. (2016). Reproductive Toxicities Caused by Swainsonine from Locoweed in Mice. BioMed Research International, 2016, 1-9.

Lu H, Zhang L, Wang S, Wang W and Zhao B. (2013). The study of the oxytropis kansuensis-induced apoptotic pathway in the cerebrum of SD rats. BMC Veterinary Research, 9(1), 217-222.

Chenchen W, Wenlong W, Xiaoxue L, Feng M, Dandan C, Xiaowen Y and Baoyu Z. (2014). Pathogenesis and preventive treatment for animal disease due to locoweed poisoning. Environmental toxicology and pharmacology, 37(1), 336-347.

Nollet H, Panter K, Vanschandevijl K, Lefere L, Stegelmeier B and Deprez P. (2008). Suspected swainsonine poisoning in a Belgian horse. Equine Veterinary Education, 20(2), 62-65.

Botha CJ and Penrith ML. (2008). Poisonous plants of veterinary and human importance in southern Africa. Journal of Ethnopharmacology, 119(3), 549-558.

Downloads

Published

2019-02-28

How to Cite

Kamarul, Z. M. A., & Mohamad, A. A. (2019). Plant toxins: alkaloids and their toxicities. GSC Biological and Pharmaceutical Sciences, 6(2), 021–029. https://doi.org/10.30574/gscbps.2019.6.2.0003

Issue

Section

Review Article