Abstract
This chapter is intended to be a presentation of alkaloids derived by amination reaction (acetate derived) from chemical, biological, and ecological points of view. The phytochemistry, isolation, biosynthesis, and biological activities of these alkaloids are described. The acetate-derived alkaloids (coniine) contained mainly in the plant poison hemlock (Conium maculatum); therefore, some of the botanical characteristics of this plant are mentioned.
It is, however, pertinent to mention at this juncture that the enormous volume of authentic information accumulated so far with regard to the isolation of alkaloids from a variety of plant species and their subsequent characterization by the help of latest analytical techniques they may be classified as alkaloids derived from amination reactions. These include:
-
(a)
Acetate-derived alkaloids
-
(b)
Phenylalanine-derived alkaloids
-
(c)
Terpenoid alkaloids
-
(d)
Steroidal alkaloids
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Aniszewski T (2007) Alkaloids – Secrets of life. Alkaloid chemistry, biological significance, applications and ecological role. Elsevier, Amsterdam
Arihan O, Boz M, Iskit AB, Ilhan M (2009) Antinociceptive activity of coniine in mice. J Ethnopharmacol 125:274–278
Ashutosh K (2007) Pharmacognosy and pharmacobiotechnology. Academic, India
Attardo C, Sartori F (2003) Pharmacologically active plant metabolites as survival strategy products. Boll Chim Farm 142:54–65
Barz W, Koster J (1981) Turnover and degradation of secondary (natural) products. In: Stumpf PK, Conn EE (eds) The biochemistry of plants, vol 7. Academic, New York, pp 35–84
Baskin JM, Baskin CC (1990) Seed germination ecology of poison hemlock Conium maculatum. Can J Bot 68:2018–2024
Baskin CC, Baskin JM (1998) Germination ecophysiology of herbaceous plant species in a temperate region. Am J Bot 75:286–305
Berger F, Ramírez-Hernández MH, Ziegler M (2004) The new life of a centenarian: signalling functions of NAD(P). Trends Biochem Sci 29:111–118
Biberci E, Altuntas Y, Chobanoglu A, Alpinar A (2002) Acute respiratory arrest following hemlock (Conium maculatum) intoxication. J Toxicol Clin Toxicol 40:517–518
Binev R (2001) Studies upon etiological and clinical symptoms on poisoning with poison hemlock (Conium maculatum) in livestock. In: Proceedings of the scientific conference with an international participation “40 years Stara Zagora Union of Scientists”, Union of Scientists, Stara Zagora vol 2, pp 97–101
Binev R, Mitev J, Miteva T (2007) Intoxication with poison hemlock (Conium maculatum L.) in calves. Tr J Sci 5:40–50
Binev R (2008) Intoxication with poison hemlock (Conium maculatum L.) in animals. Review. Ekol Fut 7:3–11
Brooks DE (2001) Plant poisoning, hemlock. Available from: www.emedicine.com/emerg/topic875.htm
Brooks DE (2008) Plant poisoning, Hemlock. eMedicine. Retrieved 20 Feb 2009
Budavari S (ed) (1996) The Merck index, 12th edn. Merck, New Jersey, p 424
Bunch TD, Panter KE, James LF (1992) Ultrasound studies of the effects of certain poisonous plants on uterine function and fetal development in livestock. J Anim Sci 70:1639–1643
Carod-Artal FJ (2003) Neurological syndromes linked with the intake of plants and fungi containing a toxic component. I. Neurotoxic syndromes caused by the ingestion of plants, seeds and fruits. Rev Neurolog 36:860–871
Castells E, Berhow MA, Vaughn SF, Berenbaum MR (2005) Geographic variation in alkaloid production in Conium maculatum populations experiencing differential herbivory by Agonopterix alstroemeriana. J Ch Ecol 31:1693–1709
Castells E, Berenbaum MR (2006) Laboratory rearing of Agonopterix alstroemeriana, the defoliating poison hemlock (Conium maculatum L.) moth, and effects of piperidine alkaloids on preference and performance. Environ Entomol 35:607–615
Corsi G, Biasci D (1998) Secretory structures and localization of alkaloids in Conium maculatum L. (Apiaceae). Ann Bot 81:157–162
Cromwell BT, Roberts MF (1964) The biogenesis of γ-coniceine in hemlock (Conium maculatum). Phytochemistry 3:369–375
Durand MF, Pommier P, Chazalette A, de Haro L (2008) Child poisoning after ingestion of a wild apiaceae: a case report. Arch Pediatr 15:139–141
Dyson D, Wrathall A (1977) Congenital deformities in pigs possibly associated with exposure to hemlock (Conium maculatum). Vet Rec 100:241–242
Edmonds LD, Selby LA, Case AA (1972) Poisoning and congenital malformations associated with consumption of poison hemlock by sows. J Am Vet Med Assoc 160:1319–1324
Forsyth CS, Frank AA (1993) Evaluation of developmental toxicity of coniine to rats and rabbits. Teratol 48:59–64
Forsyth CS, Speth RC, Wecker L, Galey FD, Frank AA (1996) Comparison of nicotinic receptor binding and biotransformation of coniine in the rat and chick. Toxicol Lett 89:175–183
Frank AA, Reed WM (1987) Conium maculatum (poison hemlock) toxicosis in a flock of range turkeys. Avian Dis 31:386–388
Frank BS, Michelson WB, Panter KE, Gardner DR (1995) Ingestion of poison hemlock (Conium maculatum). West J Med 163:573–574
Galey FD, Holstege DM, Fisher EG (1992) Toxicosis in dairy cattle exposed to poison hemlock (Conium maculatum) in hay: isolation of Conium alkaloids in plants, hay and urine. J Vet Diagn Invest 4:60–64
Gebhardt Y, Witte S, Forkmann G, Lukacin R, Matern U, Martens S (2005) Molecular evolution of flavonoid dioxygenases in the family Apiaceae. Phytochemistry 66:1273–1284
Green BT, Lee ST, Panter KE, Welch KD, Cook D, Pfister JA, Kem WR (2010) Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors. Neurotoxicol Teratol 32:383–390
Grieve M (1995–2004) Hemlock. In: A modern herbal. Botanical.com. Available from: www.botanical.com/botanical/mgmh/h/hemloc18.html
Gupta RN (1968) Biosynthesis of the piperidine alkaloids. Lloydia 31:318–326
Haupt H (2003) Poisonous and less poisonous plants. Conium maculatum and Cicuta virosa. Kinderkrankenschw 22:495–496
Holm L, Doll J, Holm E, Pancho J, Herberger L (1997) Conium maculatum. In: World weeds. Natural history and distribution. Wiley, New York, pp 221–225
Huggins J (2002) Coniine and the hemlock alkaloids. Available from: www.chm.bris.ac.uk/motm/hemlock
James LF, Panter KE, Nielsen DB, Molyneux RJ (1992) The effect of natural toxins on reproduction in livestock. J Anim Sci 70:1573–1579
James LF, Panter KE, Gaffield W, Molyneux RJ (2004) Biomedical applications of poisonous plant research. J Agric Food Chem 52:3211–3230
Jessup DA, Boermans HJ, Kock ND (1986) Toxicosis in tule elk caused by ingestion of poison hemlock. J Am Vet Med Assoc 189:1173–1175
Keeler RF, Dell Balls L, Shupe JL, Ward CM (1980) Teratogenicity and toxicity of coniine in cows, ewes, and mares. Cornell Vet 70:19–26
Keeler RF (1983) In: Keeler RF, Tu AT (eds) Handbook of natural toxins, vol 1. Marcel Dekker, New York/Basel
Keeler RF (1988) Livestock models of human birth defects, reviewed in relation to poisonous plants. J Anim Sci 66:2414–2427
Krenzelok EP, Jacobsen TD, Aronis JM (1996) Hemlock ingestions: the most deadly plant exposures. J Toxicol Clin Toxicol 34:601–602
Kutchan TM (1995) Alkaloid biosynthesis -the basis for metabolic engineering of medicinal plants. Plant Cell 7:1059–1070
Lee ST, Green BT, Welch KD, Pfister JA, Panter KE (1998) Stereoselective potencies and relative toxicities of coniine enantiomers. Chem Res Toxicol 21:2061–2064
Lee ST, Gardner DR, Chang CW, Panter KE, Molyneux RJ (2008) Separation and measurement of plant alkaloid enantiomers by RP-HPLC analysis of their Fmoc-Alanine analogs. Phytochem Anal 9:395–402
Leete E, Adityachaudhury N (1967) Biosynthesis of hemlock alkaloids II conversion of γ-coniceine to coniine and ψ-conhydrine. Phytochemistry 6:219–223
Leete E (1970) The biosynthesis of coniine from octanoic acid in hemlock plants (Conium maculatum). J Am Chem Soc 92:3835
Leete E, Olson JO (1970) 5-Oxo-octanoic acid and 5-oxo-octanal, precursors of coniine. J Chem Soc D: 1651
Leete E, Olson JO (1972) Biosynthesis and metabolism of the hemlock alkaloids. J Am Chem Soc 94:5472–5477
López TA, Odriozola E, Eyherabide J (1991) Toxicidad vegetal para el ganado. Estación Experimental Agropecuaria Balcarce (I.N.T.A.), Buenos Aires, pp 12–13
López TA, Cid MS, Bianchini ML (1999) Biochemistry of hemlock (Conium maculatum L.) alkaloids and their acute and chronic toxicity in livestock. A review. Toxicon 37:841–865
Marzocca A, Mársico O, Del Puerto O (1993) Conium maculatum. In: Manual de Malezas, 4th edn. Editorial Hemisferio Sur, Buenos Aires, pp 357–359
Mitich W (1998) Poison-hemlock (Conium maculatum L.). Weed Technol 12:194–197
Moody CJ, Lightfoot AP, Gallagher PT (1997) Asymmetric synthesis of 2-substituted piperidines. Synthesis of the alkaloids (−)-coniine and (±)-pseudoconhydrine. J Org Chem 62:746–748
Panter KE, Keeler RF (1988) The hemlocks: poison-hemlock (Conium maculatum) and water hemlock (Cicuta spp.). In: James L, Ralphs M, Nielsen D (eds) The ecology and economic impact of poisonous plants on livestock production. Westview Press, London, pp 207–235
Panter KE, Keeler K (1989) Piperidine alkaloids of poison hemlock (Conium maculatum). In: Cheeke PR (ed) Toxicants of plant origin alkaloids, vol 1. CRC Press, Boca Raton, pp 109–132
Panter KE, Keeler K (1990) Conium, Lupinus, Nicotiana alkaloids: fetal effects and the potential for residues in milk. Vet Hum Toxicol 32:89–93
Panter KE, Keeler RF, Buck W (1985) Congenital skeletal malformations induced by maternal ingestion of Conium maculatum (poison hemlock) in newborn pigs. Am J Vet Res 46:2064–2066
Panter KE, Keeler RF, Buck WB (1985) Induction of cleft palate in newborn pigs by maternal ingestion of poison-hemlock (Conium maculatum). Am J Vet Res 46:1368–1371
Panter KE, Keeler K, Baker D (1988) Toxicoses in livestock from the hemlocks (Conium and Licuta spp.). J Anim Sci 66:2407–2413
Panter KE, Keeler K, Bunch T (1988) Maternal and fetal toxicity of poison hemlock (Conium maculatum) in sheep. Am J Vet Res 49:281–283
Panter KE, Bunch TD, Keeler RF, Sisson DV, Callan RJ (1990) Multiple congenital contractures (MCC) and cleft palate induced in goats by ingestion of piperidine alkaloid-containing plants: reduction in fetal movement as the probable cause. J Toxicol Clin Toxicol 28:69–83
Panter KE, Keeler RF, Bunch TD, Callan RJ (1990) Congenital skeletal malformations and cleft palate induced in goats by ingestion of Lupinus, Conium and Nicotiana species. Toxicon 28:1377–1385
Panter KE, James LF, Keeler RF, Bunch TD (1992) Radioultrasound of poisonous plants-induced fetotoxicity in livestock. In: James LF, Keeler RF, Bailey E Jr, Cheeke P, Hegarty M (eds) Poisonous plants, Proceedings of the third international symposium. Iowa University Press, Iowa, pp 481–488
Panter KE, Keeler K, James LF, Bunch TD (1992) Impact of plant toxins on fetal and neonatal development: a review. J Ran Man 45:52–57
Pfister JA, Provenza FD (2002) Risk management to reduce livestock losses from toxic plants. J Ran Manag 55:285–290
Reding MT, Buchwald SL (2008) Short enantioselective total syntheses of the piperidine alkaloids (S)-coniine and (2R,6R)-trans-solenopsin A via catalytic asymmetric imine hydrosilylation. Chem Res Toxicol 21:2061–2064
Reynolds T (2004) In: Reynolds T (ed) Aloes – the genus Aloe. CRC Press, Boca Raton, pp 39–74
Reynolds T (2005) Hemlock alkaloids from Socrates to poison aloes. Phytochemistry 66:1399–1406
Rizzi D, Basile C, Di Maggio A, Sebastio A, Introna F Jr, Rizzi R, Scatizzi A, De Marco S, Smialek JE (1991) Clinical spectrum of accidental hemlock poisoning: neurotoxic manifestations, rhabdomyolysis and acute tubular necrosis. Nephrol Dial Transplant 6:939–943
Roberts MF (1971) The formation of γ-coniceine from 5-ketooctanal by a transaminase of Conium maculatum. Phytochemistry 10:3057–3060
Roberts MF (1974) Origin of the methyl carbon of methylconiine in Conium maculatum. Phytochemistry 13:1841–1845
Roberts MF (1974) S-adenosyl-l-methionine-coniine methyltransferase from Conium maculatum. Phytochemistry 13:1847–1851
Roberts MF (1975) γ-coniceine reductase in Conium maculatum. Phytochemistry 14:2393–2397
Roberts MF (1977) Purification and properties of l-alanine-4-ketooctanal aminotransferase from Conium maculatum. Phytochemistry 16:1381–1386
Roberts MF (1978) Separation of formation of γ-coniceine and aliphatic amines from GOT activity in Conium maculatum. Phytochemistry 17:107–112
Roberts MF (1980) An alkaloid from Conium maculatum. Planta Med 39:216
Scatizzi A, di Maggio A, Rizzi D, Sebastio AM, Basile C (1993) Acute renal failure due to tubular necrosis caused by wildfowl-mediated hemlock poisoning. Ren Fail 15:93–96
Schep LJ, Slaughter RJ, Beasley DM (2009) Nicotinic plant poisoning. Cl Toxicol 47:771–781
Shupe JL, James LF (1983) Teratogenic plants. Vet Human Toxicol 25:415–421
Swinyard CA, Bleck MD (1985) The etiology of arthrogryposis (multiple congenital contractures). Clin Orthop Relat Res 194:15–29
(1996) The Merck index. Merck, Whitehouse Station, pp 423–424
Tokarnia H, Doberainer J, Vargas Peixoto P (1992) In: James L, Keeler R, Bailey E Jr, Cheeke P, Hegarty M (eds) Poisonous plants, Proceedings of the third international symposium. Iowa State University Press, Iowa, pp 63–73
Vetter J (2004) Poison hemlock (Conium maculatum L.). F Chem Toxicol 42:1373–1382
Widmer WR (1984) Poison hemlock toxicosis in swine. Vet Med 79:405–408
Worthley LI (2002) Clinical toxicology: part II. Diagnosis and management of uncommon poisonings. Crit Care Resusc 4:216–230
Zdanevich V, Belodubrovskaya A (1997) Conium maculatum chemical composition, useful and harmful properties. Rast Res 33:108–113
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Binev, R. (2013). Alkaloids Derived by Amination Reaction: Acetate-Derived (Coniine). In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_28
Download citation
DOI: https://doi.org/10.1007/978-3-642-22144-6_28
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-22143-9
Online ISBN: 978-3-642-22144-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics