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05. CNS Plants

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05. CNS Plants Plants affecting the CNS 1 I. True alkaloids Amino acid derivates which contain nitrogen in the heterocycle 2 I.1. Tropane alkaloids Tropane rings are biosynthesised from ornithine amino acid Me = (-CH 3) Two major tropane alkaloid groups: • Solanaceous alkaloids • Coca alkaloids Natural occurence in species of Solanaceae , Erythroxylaceae, Convolvulaceae Major alkaloids are: S and R atropine (S) (R) hyoscyamine (one of its hyoscyamine enantiomers is atropine ), scopolamine (syn: hyoscin), cocaine 3 scopolamine Determination of tropane alkaloids Vitali – Morin colour reaction 1 g sample from the plant + 20 ml fuming H2SO4 solution Evaporated to dryness on a water-bath To the residue add 0,5 ml 3% (w/v) KOH in methanol bright purple colouration changes to red fades to colourless 4 Mechanism of action Inhibition of muscarinic cholinergic receptors (competitive antagonists of acetylcholine) Site of action : smooth and cardiac muscle, gland cells, in peripheral ganglia and CNS Alkaloids bounds reversible to receptors Solanaceous alkaloids are anticholinergic , reducing the activity of the parasympathetic nervous system and promoting sympathetic predominance Symptoms are developed in 30-60 minutes, lasts for 2 hours (intensive phase), later decrease for 10-12 hours (except in the eyes: 72 hours) Alkaloids are excreted with urine 5 Major symptoms 1. Xerostomia (dry mouth) 2. Mydriasis (dilated pupils) 3. Tachycardia (high heart rate) 4. Rapid breathing 5. Spasm, seizures 6. Death (respiratory failure) 6 Datura stramonium – jimsonweed Solanaceae – nightshade f. Distribution: Mexico, but naturalised in many countries Annual weed Disturbed, nutrient (nitrogen) rich fields, from early summer Used to „treat” roaring (respiratory obstruction) horses before selling them Psychoactive effects jimson weed (Jamestown, Virginia) Treatment for asthma 7 8 9 Seed is dominated by numerous pock-like depressions The surface of the seed is covered evenly with minute bumps Unmature seeds have a sweet taste! 10 Poisoning The whole plant is poisonous for all species ! Level of toxins vary among plant organs: ~ 0,2-0,6% Toxins accumulate in tissues! Generally seeds admixed into the meal It’s rarely grazed due to the bitter taste and unpleasant smell Most susceptible: pigs Less susceptible: rabbits , poultry 11 Case studies Schulman & Bolton (1998): high proportion of seed in the forage Binev et al. (2006): ensiled maize with Datura plants Soler-Rodríguez et al. (2006): lucerne hay with Datura 12 Naudé et al. (2004): hay samples contamined with Datura 13 Other Datura species Datura innoxia – downy thorn-apple 14 Hyoscyamus niger – henbane Solanaceae – nightshade f. Distribution: continental Eurasia, India, N-Africa Annual/biennial weed On waste ground and also as a cereal weed Formerly used to steal chickens, applied at witch rituals, against toothache or in beers as a flavouring As a medicine: antispasmodic, bronchodilator effect 15 16 17 Seeds are compressed and scrobiculate (pitted): having numerous shallow grooves or depressions 18 Poisoning The whole plant is poisonous for all species ! Symptoms are similar to Datura poisoning Mainly humans are affected 19 Atropa belladonna – deadly nightshade Solanaceae – nightshade f. Distribution: Europe, N-Africa, W-Asia Perennial, herbaceous plant (often growing as a subshrub) In shady forests from early summer Atropos – one of the three Greek fates of destinies Bella donna (in Italian) – beautiful lady Formerly it was used as a love potion Atropine sulphate is a mydriatic for eye examinations, antispasmodic effect 20 21 22 23 Seeds are ornamented by numerous pock-like depressions 24 Poisoning The whole plant is poisonous for all species Symptoms are similar to Datura , but poisonings are rare Average toxin content (in the above-ground parts): 0,2-2% Tolerant species: rabbit, birds, guinea pigs Susceptible species: pigs LD: for kids 2-5 berries, for adults 10-20 25 Other European species with Datura-like symptoms Scopolia carniolica – European scopolia Mandragora officinarum - mandrake 26 Coca alkaloids Erythroxylum cocoa – coca shrub with a stimulant effect 27 I.2. Benzylisoquinoline alkaloids Natural occurences mainly in species of Papaveraceae family , but also species in Aristolochiaceae and thyrosine isoquinoline Liliaceae Synthesis: isoquinoline backbone from thyrosine amino acid Most important alkaloids: morphine, codeine, papaverine, rhoedine Commercial drug tests available (Mandelin reagent) 28 Mechanism of action – opioids (morphine) Opioids bound to an opioid receptor of a neurone Blocking Ca 2+ ions entering the cells K+ ion efflux Hyperpolarization inhibition of action potential neurons less likely to fire paralysing effect, suppression of transmission of pain signals 29 Symptoms – opioids (morphine) Pinpoint pupils Spasm of the stomach or intestinal tract, vomiting Paralysis of limbs stumbling walk Slow and labored breathing Urinary retention, constipation Coma, hallucinations, death 30 Papaver rhoeas – field poppy Papaveraceae – poppy f. Distribution: cosmopolitan (worldwide) Agricultural weed (cereals); from spring Annual Pappa (in Latin) = food, milk Rhoeas (in Greek) = red Toxic agents are rhoeadine papaverine alkaloids (about 25 different molecules, the major type is rhoeadine – nearly 50% of the total) and papaverine 31 32 33 Small, kidney-shaped seeds with a dark, greyish brown colour 34 Poisoning The whole plant is poisonous (especially its milk) for all species Can be admixed in hay and meals Poisonings are rare Toxins can be excreted in the milk a potential risk for offsprings Mainly cattle, horses and sheeps are sensitive Slow recovery after poisoning 35 Other Papaver species Papaver somniferum – opium poppy Somniferum (in Latin) – „sleep bringing” Dried latex = opium The mixture of about 50 different alkaloids (morphine, codeine, papaverine, etc.) Painkilling effect János Kabay – extraction of morphine from poppy straw 36 37 I.3. Piperidine alkaloids Natural occurence in species of Apiaceae family Synthesis: piperidine nucleus biosynthesised from lysine amino acid (true alkaloid) or from acetate (pseudoalkaloid) Most important molecules: coniine , coniceine, lobeline Coniine + NaOH (KOH) unpleasant smell, similar to mice urine 38 Mechanism of action – coniine In the peripheral nervous system coniine blocks the nicotine receptors on the post-synaptic membrane of neuromuscular junctions blocking movements Depresses the cranial nerve III. depressing motor functions The central nervous system is not immediately affected Sypmtoms Symptoms develop within 0,5-2 hours Uncontrolled urination Heart rate first slow, becomes rapid Trembling, problems in movement (paralysis of limbs) Respiration becomes slow, labored, and irregular Person remains conscious and aware until respiratory paralysis 39 Conium maculatum – hemlock Apiaceae – carrot f. Distribution: Europe Disturbed habitats, on nutrient (nitrogen) rich soils from summer Biennial Maculatum (in Latin) = spotted 8 different alkaloids, mainly coniine , coniceine Death of Socrates – infusion of hemlock plant 40 41 42 43 Fruit is dry but does not split open when ripe Ridged, compressed laterally and smooth 44 Poisoning The whole plant is poisonous , but mainly the green fruits (alkaloid content up to 2-3%) All species are susceptible, mainly cattle Can be admixed into hay, silage or meal Drying can decrease toxicity About 100-500 g green leaves can be lethal 45 Case studies Gelay et al. (1992) Binev et al. (2007) 46 II. Terpenoids 47 II.1. Diterpene pseudoalkaloids Natural occurence mainly in species of Ranunculaceae, Asteraceae, Euphorbiaceae, Lamiaceae families Biosynthesised from geranyl- geranyl pyrophosphate (GGPP ) kaurene (C20 ) with a nitrogenic atom pseudoalkaloid (with C19 skeleton) Major types are aconitine and Taxus alkaloids No quick tests but determination of aconitine is possible from blood and urine see Beike et al. (2004) 48 Mechanism of action - aconitine In the cardiac and skeletal muscle cell membranes, aconitine makes the voltage-gated Na + ion channels permanently open high Na + levels in muscle cells inhibits Na +/Ca 2+ exchangers higher Ca 2+ and Na + ion availability within the muscle cell cell membrane cannot be repolarized paralysis In neurons , aconitine depolarizes both the membranes of presynaptic and postsynaptic cells by opening their voltage- gated Na + ion channels Due to the strong depolarization, the permeability of the membrane for K+ and Ca 2+ ions is increased Ca 2+ ions stimulate the release of Ach into the synaptic gap 49 Symtomps of Aconitum poisoning Paresthesia (sensation of burning) Tingling and numbness in the mouth, burning feeling in the rumen Vomiting Motoric weakness , slowing movements Heart and respiration steadily fail (asphyxia ) Ventricular arrhythmias, asystole, cardiac arrest , death 50 Aconitum lycoctonum – wolfsbane Ranunculaceae – buttercup f. Distribution: Middle and North Europe Over 250 Aconitum species mainly in the northern hemisphere Perennial In mountanious forests or gardens from mid-summer Formerly used as an arrow poison Dermal absorption of the alkaloids (aconitine , mesaconitine, hypaconitine) is possible LD 50 : 1 mg/bwkg (mice) 1-2 mg/bwkg (human) 51 52 53 Poisoning The whole plant is poisonous for all species , but mainly the tubers and the seeds (even it’s dried) Animal poisonings are rare Mainly on alpine grasslands or in gardens 54 Puschner et al. (2002) Species with similar poisonous effects see Seminar 8 Delphinium spp. – Aconitum napellus
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