Advertisement

Alkaloids in Diet

  • Cheng Chen
  • Ligen LinEmail author
Living reference work entry

Abstract

Food is one of the three basic requirements of mankind, supplying six kinds of nutrients including water, carbohydrate, protein, lipid, vitamins, and minerals. Alkaloid-containing foods are an intrinsic part of the human diet, such as tea, coffee, and tomato. These food-oriented alkaloid constituents possess diverse effects on the human body, either wanted or unwanted. A large variety of food-produced alkaloids exhibit potent bioactivities, such as caffeine, atropine, and cocaine, whereas, lots of other alkaloids are toxic to human, such as pyrrolizidine alkaloids. This chapter focuses on the alkaloids in human diet and their mode of action and possible toxic effects. To organize this chapter, the alkaloids were categorized into nine groups based on their structures: pyrrolizidine alkaloids, tropane alkaloids, quinolizidine alkaloids, isoquinoline alkaloids, quinoline alkaloids, glycoalkaloids, purine alkaloids, pyridine alkaloids, and amide alkaloids. The structures of food-derived alkaloids are described, and their pharmacological activities, bioavailability, metabolism, and toxicological effects are discussed. Moreover, the application of alkaloids in medicines and food supplement, patents, as well as a conclusion about their current impact on food safety are reviewed. The main purpose of this chapter is to provide a comprehensive and up-to-date state of knowledge from phytochemical, pharmacological, and toxicological studies performed on alkaloids in human food.

Keywords

Alkaloids Bioactive constituents Toxicity Bioavailability Safety 

Notes

Acknowledgments

Financial support by the National Natural Science Foundation of China (81872754) and the Research Fund of University of Macau (MYRG2017-00109-ICMS and MYRG2018-00037-ICMS) are gratefully acknowledged.

References

  1. Adams M, Wiedenmann M, Tittel G, Bauer R (2006) HPLC-MS trace analysis of atropine in Lycium barbarum berries. Phytochem Anal 17(5):279–283PubMedCrossRefGoogle Scholar
  2. Arzneibuch K (2004) European pharmacopoeia commentary. Wissenschaftliche Verlagsgesellschaft Stuttgart, StuttgartGoogle Scholar
  3. Arzneibuch K (2007) European pharmacopoeia commentary. Wissenschaftliche Verlagsgesellschaft Stuttgart, StuttgartGoogle Scholar
  4. Ballestero JA, Plazas PV, Kracun S, Gomez-Casati ME et al (2005) Effects of quinine, quinidine, and chloroquine on α9α10 nicotinic cholinergic receptors. Mol Pharmacol 68:822–829PubMedCrossRefGoogle Scholar
  5. Benowitz NL (1988) Pharmacologic aspects of cigarette-smoking and nicotine addiction. N Engl J Med 319(20):1318–1330PubMedCrossRefGoogle Scholar
  6. Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF (2002) Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4. J Pharmacol Exp Ther 302(2):645–650PubMedCrossRefGoogle Scholar
  7. Bhat R, Ganachari S, Deshpande R, Ravindra G, Venkataraman A (2013) Rapid biosynthesis of silver nanoparticles uing areca nut (Areca catechu) extract under microwave-assistance. J Clust Sci 24(1):107–114CrossRefGoogle Scholar
  8. Biondich AS, Joslin JD (2016) Coca: the history and medical significance of an ancient Andean tradition. Emerg Med Int 2016:4048764PubMedPubMedCentralCrossRefGoogle Scholar
  9. Brown JH, Taylor P (2006) Muscarinic receptor agonists and antagonists. In: Brunton LL, Lazo JS, Parker KL (eds) Goodman & Gilman’s the pharmacological basis of therapeutics, 11th edn. McGraw-Hill, New YorkGoogle Scholar
  10. Bucher E, Meszaros L (1989) Stechapfelsamen (Datura sp.) und deren alkaloide in futtermitteln. Kraftfutter 3(89):76–82Google Scholar
  11. Crippa A, Discacciati A, Larsson SC, Wolk A, Orsini N (2014) Coffee consumption and mortality from all causes, cardiovascular disease, and cancer: a dose-response meta-analysis. Am J Epidemiol 180(8):763–775PubMedCrossRefGoogle Scholar
  12. Deng XB, Zhu LP, Fang T et al (2016) Analysis of isoquinoline alkaloid composition and wound-induced variation in nelumbo using HPLC-MS/MS. J Agric Food Chem 64(5):1130–1136PubMedCrossRefGoogle Scholar
  13. Dharmananda S (2004) Safety issues affecting herbs: pyrrolizidine alkaloids. http://www.itmonline.org/arts/pas.htm
  14. Dusemund B, Appel KE, Lampen A (2010) Risk assessment of phytochemicals in food. DFG Senate commission on Food safety (SKLM), WeinheimGoogle Scholar
  15. Edgar JA, Roeder E, Molyneux RJ (2002) Honey from plants containing Pyrrolizidine alkaloids (PAs) a potential threat to health. J Agric Food Chem 50(10):2719–2730PubMedCrossRefGoogle Scholar
  16. EFSA (2005) Opinion of the scientific panel on dietetic products, nutrition and allergies on a request from the commission related to the evaluation of Lupin for labelling purposes. Eur Food Safety Authority J 302:1–11Google Scholar
  17. EFSA (2008a) Three quinine salts from the priority list from chemical group 30, opinion of the scientific panel on food additives, flavourings, processing aids and materials in contact with food (EFSA-Q-2003-172B). EFSA J 739:1–18Google Scholar
  18. EFSA (2008b) Tropane alkaloids (from Datura sp.) as undesirable substances in animal feed. Scientific Opinion of the Panel on Contaminants in the Food Chain. EFSA J 691:1–55Google Scholar
  19. FDA/CFSAN (2007) FDA advises dietary supplement manufacturers to remove comfrey products from the market. US Food and Drug Administration, Washington, DCGoogle Scholar
  20. Friedman M, Henika PR, Mackey BE (2003) Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice. Food Chem Toxicol 41:61–71PubMedCrossRefGoogle Scholar
  21. Jain V, Garg A, Parascandola M et al (2017) Analysis of alkaloids in areca nut-containing products by liquid chromatography–tandem mass spectrometry. J Agric Food Chem 65(9):1977–1983PubMedPubMedCentralCrossRefGoogle Scholar
  22. Je JY, Lee DB (2015) Nelumbo nucifera leaves protect hydrogen peroxide-induced hepatic damage via antioxidant enzymes and HO-1/Nrf2 activation. Food Funct 6(6):1911–1918PubMedCrossRefGoogle Scholar
  23. JECFA JFWECoFA (1993) Solanine and chaconine. Toxicological evaluation of certain food additives and naturally occurring toxicants prepared by the 39th meeting of the JECFA, WHO Food additives series 30. GenevaGoogle Scholar
  24. Jellin JM, Gregory PJ (2007) Natural medicines comprehensive database, 9th edn. Therapeutic Research Faculty and Stockton, CalifoniaGoogle Scholar
  25. Kempf M, Beuerle T, Buehringer M et al (2008) Pyrrolizidine alkaloids in honey: risk analysis by gas chromatography-mass spectrometry. Mol Nutr Food Res 52(10):1193–1200PubMedCrossRefGoogle Scholar
  26. Kenny PJ, Markou A (2006) Nicotine self-administration acutely activates brain reward systems and induces a long-lasting increase in reward sensitivity. Neuropsychopharmacology 31(6):1203–1211PubMedCrossRefGoogle Scholar
  27. Korpan YI, Nazarenko EA, Skryshevskaya IV et al (2004) Potato glycoalkaloids: true safety or false sense of security? Trends Biotechnol 22(3):147–151PubMedCrossRefGoogle Scholar
  28. Kotsopoulos J, Vitonis AF, Terry KL et al (2009) Coffee intake, variants in genes involved in caffeine metabolism, and the risk of epithelial ovarian cancer. Cancer Causes Control 20(3):335–344PubMedCrossRefGoogle Scholar
  29. Lee JS, Shukla S, Kim JA, Kim M (2015) Anti-angiogenic effect of Nelumbo nucifera leaf extracts in human umbilical vein endothelial cells with antioxidant potential. PLoS One 10(2):e0118552PubMedPubMedCentralCrossRefGoogle Scholar
  30. Liu WY, Guo JL, Xiang ZX, Deng LF, He L (2015) Nuciferine, extracted from Nelumbo nucifera Gaertn, inhibits tumorpromoting effect of nicotine involving Wnt/beta-catenin signaling in non-small cell lung cancer. J Ethnopharmacol 165:83–93PubMedCrossRefGoogle Scholar
  31. Martindale (2010) The complete drug reference; Cocaine; Hyoscyamine; Hyoscine. Pharmaceutical Press and London, UKGoogle Scholar
  32. Meletis CD, Wagner E (2002) Natural remedies for promoting skin health. Alternative and Complementary Therapies 8(3):186–190CrossRefGoogle Scholar
  33. Michels KB, Willett WC, Fuchs CS, Giovannucci E (2005) Coffee, tea, and caffeine consumption and incidence of colon and rectal cancer. J Natl Cancer Inst 97(4):282–292PubMedPubMedCentralCrossRefGoogle Scholar
  34. Peng W, Liu YJ, Wu N et al (2015) Areca catechu L. (Arecaceae): a review of its traditional uses, botany, phytochemistry, pharmacology and toxicology. J Ethnopharmacol 164:340–356PubMedCrossRefGoogle Scholar
  35. Pomerleau OF, Pomerleau CS (1984) Neuroregulators and the reinforcement of smoking-towards a biobehavioral explanation. Neurosci Biobehav Rev 8(4):503–513PubMedCrossRefGoogle Scholar
  36. Potterat O (2010) Goji (Lycium barbarum and L. chinense): phytochemistry, pharmacology and safety in the perspective of traditional uses and recent popularity. Planta Med 76(1):7–19PubMedCrossRefGoogle Scholar
  37. Prakash AS, Pereira TN, Reilly PEB, Seawright AA (1999) Pyrrolizidine alkaloids in human diet. Mutat Res Genet Toxicol Environ Mutagen 443(1–2):53–67CrossRefGoogle Scholar
  38. Reen RK, Jamwal DS, Taneja SC et al (1993) Impairment of Udp-glucose dehydrogenase and gucuronidation activities in liver and small-intestine of rat and Guinea-pig in-vitro by piperine. Biochem Pharmacol 46(2):229–238PubMedCrossRefGoogle Scholar
  39. Schraufnagel DE, Blasi F, Drummond MB et al (2014) Electronic cigarettes a position statement of the forum of international respiratory societies. Am J Respir Crit Care Med 190(6):611–618PubMedCrossRefGoogle Scholar
  40. U.S. Department of Health and Human Services PHSOotSGR (2016) E-cigarette use among youth and young adults: a report of the surgeon general. https://www.surgeongeneral.gov/library/2016ecigarettes/index.html
  41. Vivekanandarajah A, Waters KA, Machaalani R (2019) Cigarette smoke exposure effects on the brainstem expression of nicotinic acetylcholine receptors (nAChRs), and on cardiac, respiratory and sleep physiologies. Respir Physiol Neurobiol 259:1–15PubMedCrossRefGoogle Scholar
  42. Wang MX, Liu YL, Yang Y et al (2015a) Nuciferine restores potassium oxonate-induced hyperuricemia and kidney inflammation in mice. Eur J Pharmacol 747:59–70PubMedCrossRefGoogle Scholar
  43. Wang XF, Cheang WS, Yang HX et al (2015b) Nuciferine relaxes rat mesenteric arteries through endothelium-dependent and -independent mechanisms. Br J Pharmacol 172(23):5609–5618PubMedPubMedCentralCrossRefGoogle Scholar
  44. Wennig R (2009) Back to the roots of modern analytical toxicology: Jean Servais Stas and the Bocarme murder case. Drug Test Anal 1(4):153–155PubMedCrossRefGoogle Scholar
  45. Wiedenfeld H, Roeder E, Bourauel T, Edgar J (2008) Pyrrolizidine alkaloids (PAs) structure and toxicity. Bonn University Press, BonnGoogle Scholar
  46. Yan MZ, Chang Q, Zhong Y et al (2015) Lotus leaf alkaloid extract displays sedative–hypnotic and anxiolytic effects through GABAA receptor. J Agric Food Chem 63(42):9277–9285PubMedCrossRefGoogle Scholar
  47. Ye LH, He XX, Kong LT et al (2014) Identification and characterization of potent CYP2D6 inhibitors in lotus leaves. J Ethnopharmacol 153(1):190–196PubMedCrossRefGoogle Scholar
  48. Zhang XY, Wang XY, Wu TT et al (2015) Isoliensinine induces apoptosis in triple-negative human breast cancer cells through ROS generation and p38 MAPK/JNK activation. Sci Rep 5:12579PubMedPubMedCentralCrossRefGoogle Scholar
  49. Zheng LL, Cao YW, Liu S, Peng ZY, Zhang SD (2014) Neferine inhibits angiotensin II-induced rat aortic smooth muscle cell proliferation predominantly by downregulating fractalkine gene expression. Exp Ther Med 8(5):1545–1550PubMedPubMedCentralCrossRefGoogle Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2020

Authors and Affiliations

  1. 1.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical SciencesUniversity of MacauMacauChina

Personalised recommendations