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Conium maculatum Hemlock alkaloids

L6pez, T. A., Cid, M. S. and Bianchini, M. L. 1999. Biochemistry of hemlock (Conium maculatum L.) alkaloids and their acute and chronic toxicity in livestock. A review. Toxicon, 37 841-865. [Pg.266]

Alkaloids are widespread in plants and include some very well-known poisons (notably coniine and strychnine), hallucinogens (morphine, cocaine and muscimol) and other potentially lethal compounds that are nevertheless used in medical practice (e.g. atropine, codeine, colchicine and morphine). As indicated by the preliminary snap-shot above, alkaloids typically have names ending in -ine and which are often related to the plant source or properties. Thus, morphine was named after Morpheus (the God of sleep) and coniine derives from Conium maculatum (hemlock), the plant used in the judicial murder of Socrates (399 BC). Various chemical tests for alkaloids are used as preliminary indicators of alkaloid presence in crude plant extracts. Finally, it should be noted that alkaloids can also exist as jVoxides of the alkaloid base. [Pg.8]

Conium maculatum (hemlock) contains the poisonons piperidine alkaloid, coniine, and related alkaloids, N-methyl-coniine, conhydrine, pseudoconhydrine, and gamma-coniceine. It has well-established teratogenic activity in certain animal species. [Pg.328]

Lopez TA, Odriozola E, Eyherabide J (1991) Toxicidad vegetal para el ganado. Estacion Experimental Agropecuaria Balcarce (I.N.T.A.), Buenos Aires, pp 12-13 Lopez 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, Marsico O, Del Puerto O (1993) Conium maculatum. In Manual de Malezas, 4th edn. Editorial Hemisferio Sur, Buenos Aires, pp 357-359... [Pg.905]

Coniine (12), impHcated by Plato in the death of Socrates, is the major toxic constituent of Conium maculatum L. (poison hemlock) and, as pointed out eadier, was apparendy the first alkaloid to be synthesized. For years it was thought that coniine was derived from lysine (24), as were many of its obvious relatives containing reduced piperidine nuclei and a side chain, eg, peUetierine (46). However, it is now known (99) that coniine is derived from a polyketooctanoic acid [7028-40-2] (138), CgH QO, or some other similar straight chain analogue. [Pg.557]

The common hemlock, Conium maculatum, contain five alkaloids. Power and Tutin found a similar mixture in fool s parsley, and a volatile alkaloid resembling coniine i.s stated to occur in certain aroids. According to Svagr, water hemlock Cicuta virosa) owes its poisonous properties to toxin and not to cicutine, a name sometimes used as a synonym for coniine. The toxic properties of hemlock juice have been known ftom very early times thus it was the chief ingredient in the poison administered to criminals by the Greeks. The leaves and the unripe fruits are the parts used in medicine. The following are the names and formulae of the alkaloids —... [Pg.13]

Figure 2.2 Three piperidine alkaloid teratogens from Conium maculatum (poison-hemlock) (a) coniine, (b) y-coniceine, and (c) A-methyl coniine, with accompanying LD50 as determined in a mouse bioassay. Figure 2.2 Three piperidine alkaloid teratogens from Conium maculatum (poison-hemlock) (a) coniine, (b) y-coniceine, and (c) A-methyl coniine, with accompanying LD50 as determined in a mouse bioassay.
Banter, K.E. and Keeler, R.F. (1989). Biperidine alkaloids of poison hemlock (Conium maculatum), in Cheeke, B.R., Ed., Toxicants of plant origin, Vol. I Alkaloids, CRC Bress, Boca Raton, pp. 109-132. [Pg.70]

Neurotoxic - death Poison hemlock (Conium maculatum) Coniine - neurotoxic alkaloid -poison used by Socrates... [Pg.168]

Piperidine alkaloids such as coniine and (—)-coniceine are very poisonous. They occur in hemlock (Conium maculatum L.), known as a very toxic plant. One of the characteristics of these piperidine alkaloids is smell. Moreover, they are neurotoxins which have acute effects such as chronic toxicity. [Pg.161]

Bowman, W. C. and Sanghvi, I. S. 1963. Pharmacological actions of hemlock (Conium maculatum) alkaloids. Journal of Pharmacy and Pharmacology, 15 1-25. [Pg.266]

Heterocycles which are not biosynthesized in humans, but which are natural products produced by other life forms, are very important in the history of drug design. This is particularly true of alkaloids containing a piperidine ring. These include coniine (8.87, extracted from poison hemlock, Conium maculatum, a member of the Umbelliferae carrot family), atropine (from Atropa belladonna and other genera of the Solanaceae plant family the plant was called belladonna [ beautiful woman ] since it was used by... [Pg.530]

An alkaloid obtained mainly from the fruits and leaves of hemlock, Conium maculatum (Umbelliferae). [Pg.493]

Coniine, a poisonous alkaloid isolated from the seeds, leaves, and roots of hemlock Conium maculatum), has been known since ancient times. Ingestion causes weakness, paralysis, and finally death. The Greek philosopher Socrates was executed by being forced to drink a potion prepared from hemlock in 339 b.c. [Pg.957]

The first alkaloid which we shall consider is of especial interest historically. The Greek philosopher Socrates was put to death by being compelled to drink an extract of hemlock, Conium maculatum. In the fruit and leaves of this plant there are present six different alkaloids one of which is named from the plant and is known as conine. This compound is a colorless, strongly alkaline liquid acting as a deadly poison when taken in more than extremely small doses. Physiologically it produces paralysis of the motor nerve terminations and depression of the central nervous system. [Pg.885]

Frank AA and Reed WM (1990) Comparative toxicity of coniine, an alkaloid of Conium maculatum (poison hemlock), in chickens, quails, and turkeys. Avian Diseases 34 433-437. [Pg.661]

Galey FD, Holstege DM, and Fisher EG (1992) Toxicosis in dairy cattle exposed to poison hemlock (Conium maculatum) in hay Isolation of Conium alkaloids in plants, hay, and urine. Journal of Veterinary Diagnostic Investigation 4 60-64. [Pg.661]

Plants of many genera produce compounds called alkaloids (alkali-like), and indeed all the thousands of known alkaloids contain nitrogen, by definition, and most are basic, and many are also toxic. Nicotine, a structurally simple example of an alkaloid, is a highly toxic substance, and is the major active component in tobacco (Nicotiam sp.), and amongst the most addictive drugs - an extraordinary contrast to the vital role in life played by nicotinic acid amide (32.2.1). Coniine, the active ingredient of hemlock (Conium maculatum), is another stmcturally simple example. [Pg.637]

Coniine is present in all parts of the plant poison hemlock (Conium maculatum). It is the first alkaloid to be synthesized and structure determined. Because of its high toxicity, its clinical application is very limited. [Pg.223]

Although the alkaloids coniine (48) and y-coniceine (51) bear a structural resemblance to the piperidine alkaloids, these compounds are derived from a polyketide pathway (Fig. 29.17). Lysine is a poor precursor, and early attempts to show incorporation of this compound resulted in failure. Acetate is a much better precursor. Coniine is a highly toxic alkaloid and is one of the toxic components of poison hemlock (Conium maculatum, Apiaceae) (Cutler, 1992). Otherwise, alkaloids are very uncommon in the Apiaceae. Coniine does occur in several other plants, for example, Sarracenia (Sarracenia). y-Coniceine is found in several species of Aloe (Liliaceae) (Dring et al., 1984). Coniine is toxic to the aquatic plant Lemna (Wink, 1993). The LDioo p.o. in the... [Pg.543]

Coniine, 2-propylpiperidine the most important of the Conium alkaloids (see), and the toxic principle of the poison hemlock, Conium maculatum, which was used in ancient Athens to put Socrates to death. The lethal dose of C. in humans is 0.5-1 g. The largest quantities of C. are found in the unripe seeds The synthesis of C. from a-picoline and paraldehyde by Ladenburg in 1886 was the first laboratory synthesis of any alkaloid. M, 127.22, m.p. -2.5 C, b.p. 166 C, [a] 7 16°. [Pg.134]

Conium alkaloids simple piperidine alkaloids found only in poison hemlock, Conium maculatum. The main alkaloids are Coniine (see) and y-coniceine (M, 125.22, b.p. 168°C) the secondary alkaloids are A -methyl and hydroxy derivatives of coniine. In contrast to other piperidine alkaloids, the ring system of C. a. is synthesized from acetate rather than from lysine (Fig.). [Pg.134]

Coniine is the toxic principle of hemlock ( Conium maculatum). It repels potential predators (E 5.5.3). In the pitcher traps of Sarracenia the alkaloid paralyzes captured insects. [Pg.178]

The coniine is the most important alkaloid of the hemlock plants. Craiiine, one of the major toxic alkaloids present in poison hemlock (Conium maculatum), occurs in two optically active forms [36, 45]. [Pg.884]

The biological activities of the poison hemlock (Conium maculatum) are due to the content of piperidine alkaloids — coniine (2-propylpiperidine), y-coniceine (2n-propyl-ly-piperidine), conhydrine (2-(l- hydroxypropyl)-piperi-dine), A/-methylc(Miiine (1-methyl-2- propylpiperidine), pseudoconhydrine ((5-hydroxypropyl)-piperidine), conhydrinone ((l-oxo-propyl)-piperidine), W-methylpseudoconhydrine (5-hydroxy-l-methyl-2-propyl-piperidine), and 2-methylpiperidine. The poismiing effect of hemlock supplements by the presence of poly-p-keto acid (2,5,7-tri-oxo-octanoic acid), quercetin, kaempferol, and glycoside dioxymid [4, 12,13, 20, 52, 85, 87]. [Pg.897]

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... [Pg.904]

Leete E, Adityachaudhury N (1967) Biosynthesis of hemlock alkaloids II conversion of y-coniceine to coniine and l/-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... [Pg.905]

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... [Pg.905]

Evidence for a type of bound alkaloid emerged in the course of Fairbairn s studies on the distribution and variation in content of alkaloids in hemlock (Conium maculatum). The bound form is supposed to yield an alkaloid in the plant tissue upon hydrolysis. It may be possible that nucleotide-like compounds exist (see Section 6.4). [Pg.234]


See other pages where Conium maculatum Hemlock alkaloids is mentioned: [Pg.531]    [Pg.23]    [Pg.184]    [Pg.529]    [Pg.382]    [Pg.144]    [Pg.76]    [Pg.70]    [Pg.211]    [Pg.363]    [Pg.393]    [Pg.884]    [Pg.886]    [Pg.903]   


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