Abstract
Compared to GPCRs, the set of plant-derived compounds that target ion channels appears much more limited. For voltage-gated channels, most known toxins are derived from animals such as snails, spiders and snakes. Also, many ligand-gated channels are targeted by few to none known plant-derived drugs. Nevertheless, ion channels are the target of some of the most potent plant poisons and most commonly used plant-derived drugs.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Baldwin IT (1988) The alkaloidal responses of wild tobacco to real and simulated herbivory. Oecologia 77(3):378–381. https://doi.org/10.1007/bf00378046
Bates SS, Douglas DJ, Doucette GJ, Léger C (1995) Enhancement of domoic acid production by reintroducing bacteria to axenic cultures of the diatom Pseudo-nitzschia multiseries. Nat Toxins 3(6):428–435. https://doi.org/10.1002/nt.2620030605
Battersby AR, Hodson HF (1965) Chapter 15 alkaloids of calabash curare and Strychnos species**the majority of Strychnos alkaloids which are based upon the strychnine skeleton are covered in chapter 17. In: RHF M (ed) The alkaloids: chemistry and physiology, vol 8. Academic press, pp 515–579. https://doi.org/10.1016/S1876-0813(08)60054-8
Bock JH, Norris DO (2016) Chapter 1 - introduction to forensic plant science. In: Forensic plant science. Academic Press, San Diego, pp 1–22. https://doi.org/10.1016/B978-0-12-801475-2.00001-4
Boehm R (1897) Ueber Curare und Curarealkaloide. Arch Pharm 235(8–9):660–684. https://doi.org/10.1002/ardp.18972350812
Bonpland A, Humboldt A, William HM (1814) Personal narrative of travels to the equinoctial regions of America during the years 1799-1804. Longman, Hurst, Rees, Orme, and Brown, London
Brown TK (2013) Ibogaine in the treatment of substance dependence. Curr Drug Abuse Rev 6(1):3–16
Cembella AD (1998) Ecophysiology and metabolism of paralytic shellfish toxins in marine microalgae. In: Anderson DM, Cembella AD, Hallegraeff GM (eds) Physiological ecology of harmful blooms. Springer, Berlin, Heidelberg, pp 381–403
Chan TY (2009) Aconite poisoning. Clin Toxicol (Phila) 47(4):279–285. https://doi.org/10.1080/15563650902904407
Czarnowski C, Bailey J, Bal S (2007) Curare and a Canadian connection. Can Fam Physician 53(9):1531–1532
Dayan AD (2009) What killed Socrates? Toxicological considerations and questions. Postgrad Med J 85(999):34–37. https://doi.org/10.1136/pgmj.2008.074922
Edwards C, Beattie KA, Scrimgeour CM, Codd GA (1992) Identification of anatoxin-A in benthic cyanobacteria (blue-green algae) and in associated dog poisonings at Loch Insh, Scotland. Toxicon 30(10):1165–1175. https://doi.org/10.1016/0041-0101(92)90432-5
Eiden F (2003) Strychnine, ein ganz besonderes Gift. Kultur & Technik 27:24–30
Franzios G, Mirotsou M, Hatziapostolou E, Kral J, Scouras ZG, Mavragani-Tsipidou P (1997) Insecticidal and genotoxic activities of mint essential oils. J Agric Food Chem 45(7):2690–2694. https://doi.org/10.1021/jf960685f
Fuentealba J, Guzmán L, Manríquez-Navarro P, Pérez C, Silva M, Becerra J, Aguayo LG (2007) Inhibitory effects of tutin on glycine receptors in spinal neurons. Eur J Pharmacol 559(1):61–64. https://doi.org/10.1016/j.ejphar.2006.12.018
Galeotti N, Di Cesare ML, Mazzanti G, Bartolini A, Ghelardini C (2002) Menthol: a natural analgesic compound. Neurosci Lett 322. https://doi.org/10.1016/S0304-3940(01)02527-7
Hall RD, Holden MA, Yeoman MM (1987) The accumulation of phenylpropanoid and capsaicinoid compounds in cell cultures and whole fruit of the chilli pepper, Capsicum frutescens mill. Plant Cell Tissue Organ Cult 8(2):163–176. https://doi.org/10.1007/bf00043153
Harvell KP, Bosland PW (1997) The environment produces a significant effect on pungency of chilies. Hort Sci 32:1292
Holland A, Kinnear S (2013) Interpreting the possible ecological role(s) of cyanotoxins: compounds for competitive advantage and/or physiological aide? Mar Drugs 11(7):2239–2258. https://doi.org/10.3390/md11072239
Islam MN, Khalil MI, Islam MA, Gan SH (2014) Toxic compounds in honey. J Appl Toxicol 34(7):733–742. https://doi.org/10.1002/jat.2952
Jennings KR, Brown DG, Wright DP (1986) Methyllycaconitine, a naturally occurring insecticide with a high affinity for the insect cholinergic receptor. Experientia 42(6):611–613. https://doi.org/10.1007/bf01955557
Jordt S-E, Julius D (2002) Molecular basis for species-specific sensitivity to “hot” chili peppers. Cell 108(3):421–430. https://doi.org/10.1016/S0092-8674(02)00637-2
Kakemoto E, Okuyama E, Nagata K, Ozoe Y (1999) Interaction of anisatin with rat brain gamma-aminobutyric acidA receptors: allosteric modulation by competitive antagonists. Biochem Pharmacol 58(4):617–621
Kamatou GPP, Vermaak I, Viljoen AM, Lawrence BM (2013) Menthol: a simple monoterpene with remarkable biological properties. Phytochemistry 96:15–25. https://doi.org/10.1016/j.phytochem.2013.08.005
Karban R, Shiojiri K, Huntzinger M, McCall AC (2006) Damage-induced resistance in sagebrush: volatiles are key to intra- and interplant communication. Ecology 87(4):922–930
Karban R, Wetzel WC, Shiojiri K, Ishizaki S, Ramirez SR, Blande JD (2014) Deciphering the language of plant communication: volatile chemotypes of sagebrush. New Phytol 204(2):380–385. https://doi.org/10.1111/nph.12887
Kellmann R, Mihali TK, Jeon YJ, Pickford R, Pomati F, Neilan BA (2008) Biosynthetic intermediate analysis and functional homology reveal a saxitoxin gene cluster in cyanobacteria. Appl Environ Microbiol 74(13):4044–4053. https://doi.org/10.1128/AEM.00353-08
Kennedy DO, Wightman EL (2011) Herbal extracts and phytochemicals: plant secondary metabolites and the enhancement of human brain function. Adv Nutr 2(1):32–50. https://doi.org/10.3945/an.110.000117
King H (1948) 394. Curare alkaloids. Part VIII. Examination of commercial curare, Chondrodendron tomentosum R and P and Anomospermum grandifolium eichl. J Chem Soc (Resumed):1945–1949. https://doi.org/10.1039/JR9480001945
Krienitz L, Ballot A, Kotut K, Wiegand C, Putz S, Metcalf JS, Codd GA, Pflugmacher S (2003) Contribution of hot spring cyanobacteria to the mysterious deaths of lesser flamingos at Lake Bogoria, Kenya. FEMS Microbiol Ecol 43(2):141–148. https://doi.org/10.1111/j.1574-6941.2003.tb01053.x
Kudakasseril GJ, Staba EJ (1988) Insecticidal phytochemicals. https://doi.org/10.1016/B978-0-12-715005-5.50038-8
Kumar P, Pandit SS, Steppuhn A, Baldwin IT (2014) Natural history-driven, plant-mediated RNAi-based study reveals <em>CYP6B46</em>‘s role in a nicotine-mediated antipredator herbivore defense. Proc Natl Acad Sci 111(4):1245–1252. https://doi.org/10.1073/pnas.1314848111
Lashley KS (1917) The effects of strychnine and caffeine upon the rate of learning. Psychobiology 1. https://doi.org/10.1037/h0075094
Lin Y, Qasim M, Hussain M, Akutse K, Avery P, Dash C, Wang L (2017) The herbivore-induced plant volatiles methyl salicylate and menthol positively affect growth and pathogenicity of entomopathogenic fungi. Sci Rep:7, 40494. https://doi.org/10.1038/srep40494
Ma LJ, Gu RH, Tang L, Chen ZE, Di R, Long CL (2015) Important poisonous plants in tibetan ethnomedicine. Toxins (Basel) 7(1):138–155. https://doi.org/10.3390/toxins7010138
Mauck WL, Olson LE (1976) Toxicity of natural pyrethrins and five pyrethroids to fish. Arch Environ Contam Toxicol 4(1):18–29
McGaugh JL, Roozendaal B (2009) Drug enhancement of memory consolidation: historical perspective and neurobiological implications. Psychopharmacology 202(1):3–14. https://doi.org/10.1007/s00213-008-1285-6
McLaughlin GA (1973) Chapter 1 – history of pyrethrum A2 - CASIDA. In: John E (ed) Pyrethrum. Academic Press, New York, pp 3–15. https://doi.org/10.1016/B978-0-12-162950-2.50008-9
Mebs D, Schäfer C (2008) Kleopatra und der Kobrabiß – das Ende eines Mythos?, vol 90. doi:https://doi.org/10.1524/klio.2008.0015
Meghvansi MK, Siddiqui S, Khan MH, Gupta VK, Vairale MG, Gogoi HK, Singh L (2010) Naga chilli: a potential source of capsaicinoids with broad-spectrum ethnopharmacological applications. J Ethnopharmacol 132(1):1–14. https://doi.org/10.1016/j.jep.2010.08.034
Miles WR (1929) Drug effects measured by acquired patterns of response. Am J Physiol 90:451–451
Mody NV, Henson R, Hedin PA, Kokpol U, Miles DH (1976) Isolation of the insect paralyzing agent coniine fromSarracenia flava. Experientia 32(7):829–830. https://doi.org/10.1007/bf02003710
Mos L (2001) Domoic acid: a fascinating marine toxin. Environ Toxicol Pharmacol 9(3):79–85. https://doi.org/10.1016/S1382-6689(00)00065-X
Murad L, Lim KY, Christopodulou V, Matyasek R, Lichtenstein CP, Kovarik A, Leitch AR (2002) The origin of tobacco’s T genome is traced to a particular lineage within Nicotiana tomentosiformis (Solanaceae). Am J Bot 89(6):921–928. https://doi.org/10.3732/ajb.89.6.921
Olney JW, Rhee V, Ho OL (1974) Kainic acid: a powerful neurotoxic analogue of glutamate. Brain Res 77(3):507–512. https://doi.org/10.1016/0006-8993(74)90640-4
Pelletier PJ, Caventou JB (1819) Mémoire sur un nouvel alcali vegetal (la strychnine) trouvé dans la feve de Saint-Ignace, la noix vomique, etc. Annales de Chimie et de Physique 10:142–176
Perry L, Dickau R, Zarrillo S, Holst I, Pearsall DM, Piperno DR, Berman MJ, Cooke RG, Rademaker K, Ranere AJ, Raymond JS, Sandweiss DH, Scaramelli F, Tarble K, Zeidler JA (2007) Starch fossils and the domestication and dispersal of chili peppers (<em>Capsicum</em> spp. L.) in the Americas. Science 315(5814):986–988. https://doi.org/10.1126/science.1136914
Philippe G, Angenot L, Tits M, Frédérich M (2004) About the toxicity of some Strychnos species and their alkaloids. Toxicon 44(4):405–416. https://doi.org/10.1016/j.toxicon.2004.05.006
Popik P, Layer RT, Fossom LH, Benveniste M, Geter-Douglass B, Witkin JM, Skolnick P (1995) NMDA antagonist properties of the putative antiaddictive drug, ibogaine. J Pharmacol Exp Ther 275(2):753–760
Premkumar LS (2014) Transient receptor potential channels as targets for phytochemicals. ACS Chem Neurosci 5(11):1117–1130. https://doi.org/10.1021/cn500094a
Ramirez AM, Stoopen G, Menzel TR, Gols R, Bouwmeester HJ, Dicke M, Jongsma MA (2012) Bidirectional secretions from glandular trichomes of pyrethrum enable immunization of seedlings. Plant Cell 24(10):4252–4265. https://doi.org/10.1105/tpc.112.105031
Ramirez AM, Saillard N, Yang T, Franssen MC, Bouwmeester HJ, Jongsma MA (2013) Biosynthesis of sesquiterpene lactones in pyrethrum (Tanacetum cinerariifolium). PLoS One 8(5):e65030. https://doi.org/10.1371/journal.pone.0065030
Rapala J, Sivonen K, Luukkainen R, Niemelä SI (1993) Anatoxin-a concentration inAnabaena andAphanizomenon under different environmental conditions and comparison of growth by toxic and non-toxicAnabaena-strains — a laboratory study. J Appl Phycol 5(6):581–591. https://doi.org/10.1007/bf02184637
Rogers EF, Koniuszy FR, Shavel J, Folkers K (1948) Plant insecticides; ryanodine, a new alkaloid from Ryania speciosa Vahl. J Am Chem Soc 70(9):3086–3088. https://doi.org/10.1021/ja01189a074
Santulli G, Marks AR (2015) Essential roles of intracellular calcium release channels in muscle, brain, metabolism, and aging. Curr Mol Pharmacol 8(2):206–222
Schep LJ, Slaughter RJ, Becket G, Beasley DM (2009) Poisoning due to water hemlock. Clin Toxicol (Phila) 47(4):270–278. https://doi.org/10.1080/15563650902904332
Smith BA (1990) Strychnine poisoning. J Emerg Med 8(3):321–325. https://doi.org/10.1016/0736-4679(90)90013-L
Soderlun DM, Lee SH (2001) Point mutations in homology domain II modify the sensitivity of rat Nav1.8 sodium channels to the pyrethroid insecticide cismethrin. Neurotoxicology 22(6):755–765
Soderlund DM, Clark JM, Sheets LP, Mullin LS, Piccirillo VJ, Sargent D, Stevens JT, Weiner ML (2002) Mechanisms of pyrethroid neurotoxicity: implications for cumulative risk assessment. Toxicology 171(1):3–59
Tewksbury JJ, Nabhan GP (2001) Directed deterrence by capsaicin in chillies. Nature 412:403. https://doi.org/10.1038/35086653
Thomas NL, Williams AJ (2012) Pharmacology of ryanodine receptors and Ca2+−induced Ca2+ release. Wiley Interdiscip Rev Membr Transp Signal 1(4):383–397. https://doi.org/10.1002/wmts.34
Tufariello JJ, Meckler H, Senaratne KP (1984) Synthesis of anatoxin-a: very fast death factor. J Am Chem Soc 106(25):7979–7980. https://doi.org/10.1021/ja00337a059
Vais H, Atkinson S, Eldursi N, Devonshire AL, Williamson MS, Usherwood PN (2000) A single amino acid change makes a rat neuronal sodium channel highly sensitive to pyrethroid insecticides. FEBS Lett 470(2):135–138
Vetter J (2004) Poison hemlock (Conium maculatum L.). Food Chem Toxicol 42(9):1373–1382. https://doi.org/10.1016/j.fct.2004.04.009
Walker N, Howe C, Glover M, McRobbie H, Barnes J, Nosa V, Parag V, Bassett B, Bullen C (2014) Cytisine versus nicotine for smoking cessation. N Engl J Med 371(25):2353–2362. https://doi.org/10.1056/NEJMoa1407764
Wennig R (2009) Back to the roots of modern analytical toxicology: Jean Servais Stas and the Bocarmé murder case. Drug Test Anal 1(4):153–155. https://doi.org/10.1002/dta.32
Wickham R (2015) How menthol alters tobacco-smoking behavior: a biological perspective. Yale J Biol Med 88:279–287
Wiese M, D’Agostino PM, Mihali TK, Moffitt MC, Neilan BA (2010) Neurotoxic alkaloids: saxitoxin and its analogs. Mar Drugs 8(7):2185–2211. https://doi.org/10.3390/md8072185
Wink M, Theile V (2002) Alkaloid tolerance in Manduca sexta and phylogenetically related sphingids (Lepidoptera: Sphingidae). Chemoecology 12(1):29–46. https://doi.org/10.1007/s00049-002-8324-2
Wolf FW, Heberlein U (2003) Invertebrate models of drug abuse. J Neurobiol 54(1):161–178. https://doi.org/10.1002/neu.10166
Zhou DS, Wang CZ, van Loon JJA (2009) Chemosensory basis of behavioural plasticity in response to deterrent plant chemicals in the larva of the small cabbage white butterfly Pieris rapae. J Insect Physiol 55(9):788–792. https://doi.org/10.1016/j.jinsphys.2009.04.011
Zubaran C (2000) Ibogaine and noribogaine: comparing parent compound to metabolite. CNS Drug Rev 6(3):219–240. https://doi.org/10.1111/j.1527-3458.2000.tb00149.x
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2018 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Böttger, A., Vothknecht, U., Bolle, C., Wolf, A. (2018). Plant-Derived Drugs Affecting Ion Channels. In: Lessons on Caffeine, Cannabis & Co. Learning Materials in Biosciences. Springer, Cham. https://doi.org/10.1007/978-3-319-99546-5_8
Download citation
DOI: https://doi.org/10.1007/978-3-319-99546-5_8
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-99545-8
Online ISBN: 978-3-319-99546-5
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)