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ERSITY IV  N S Assam University Journal of Science & Technology : ISSN 0975-2773 U I L M C

H A

S A Biological and Environmental Sciences

R S A Vol. 7 Number I 139-144, 2011

Neurotoxic and Medicinal Properties of L. – Review Maibam Rasila Devi1, Meenakshi Bawari1, S.B Paul2, G.D.Sharma1 1Department of Life Science and Bioinformatics 2Department of Chemistry, Assam University, Silchar-788011, Assam, *Corresponding author email: [email protected]

Abstract The troublesome , jimson weed (Datura stramonium L.) is a with both poisonous and medicinal properties. The neurotoxicity is attributed to the presence of alkaloids which contain a methylated nitrogen atom (N-CH3) and include the , and , as well as the . A wide range of medicinal values of this plant have contributed in scientific field and also in ethnomedicine. The phytochemical, ethnomedicinal and toxicological works on D.stramonium has given a better assessment and information of this particular plant. The present paper presents an exclusive review work on the neurotoxic properties of D. stramonium. Keywords : Datura stramonium, tropane alkaloids, ethnomedicine, neurotoxicity, intoxication, anticholinergic

Introduction Datura stramonium is a wild-growing herb, the highest concentration. An extract made by known as Jimson weed. It also has several other boiling crushed retains the anticholinergic names: thorn apple, angel’s trumpet, loco weed, activity, has a rapid onset of action (Chang et etc. The incidence of D. stramonium poisoning al., 1999) and thus may be potentially useful is sporadic with a cluster of poisoning cases as an alternative to atropine for the treatment occurring mostly among adolescents. Some of the muscarinic symptoms of organophosphate medicinal uses of the plant are its anti- toxicity and some of central anticholinergic effects inflammatory property of all part of the (Theodore et al., 2004). The wide distribution, (Spring, 1989), stimulation of the central nervous the strong toxicity and the potential for system (CNS) (Guarov and Barajas,1991; occurrence in foodstuffs are responsible for Manandhar, 1995), respiratory decongestion the numerous incidents in humans (Roblot et (Zagari, 1992), treatment of dental and skin al.,1995; Arouko et al., 2003; Boumba et al.,2005; infections (John,1984; Darias et al., 1986; De Foe Ertekin et al.,2005; Oberndorfer et al.,2002; and Senatore, 1993) and also in the treatment Thabet et al.,1999; Shaikh et al., 2005). The of toothache (Abebe,1986) and alopecia (John, anticholinergic compounds of D.stramonium are 1984). It is a hallucinogenic plant that causes likely to produce and stupor but rarely serious poisoning. Consumption of any part of cause deep coma. The plant is a rich source the plant may result in a severe anticholinergic of alkaloids and it is an analgesic herb. reaction that may lead to toxicity and occasionally extract has an analgesic effect in both acute cause diagnostic difficulties (Diker, 2006). It is and chronic pain (Khalili and Atyabi, 2004).It is used recreationally for its anticholinergic effects, also used frequently in anti-asthmatic treatment resulting in . The entire plant has and known for its hallucinogenic and euphoric anti-cholinergic compounds, but the seeds contain effects (Muller, 1998; Weitz, 2003 and Ertekin

- 139 - Neurotoxic and Medicinal Properties of...... et al., 2005). The plant occurs indigenously in 7-hydroxyhyoscyamine are reported for the first Southern Africa and distributed to other areas time for this species (Strahil Berkov et al., 2005). of the world. It was used by Red Indians for Table no. 1: List of the other alkaloids found in many years as euphoric agent and since the D.stramonium (Strahil Berkov et al., 2006) 1800’s, used as a therapeutic agent and in Great Britian (Dessanges, 2001). However over 1) Hygrine dosage can result in severe toxicity. 2) 3á,6â-Ditigloyloxy-7-hydroxytropane D.stramonium contains a variety of alkaloids 3) 6-Hydroxyhyoscyamine that can cause anticholinergic poisoning if taken 4) Pseudotropine in large concentrations (Ertekin et al., 2005).The 5) 3á-Tigloyloxytropane anticholinergic alkaloids contribute to the anti- 6) Hydroxy-6-tigloyloxytropane asthmatic properties (Friedman, 2004). Atropine 7) Phenylacetoxytropane is found to have more exciting properties, while 8) 3-Tigloyloxy-6-(2-methylbutyryloxy) scopolamine has more relaxing and tropane hallucinogenic properties (Weitz, 2003). It has 9) been reported that all parts of the plant are 10) 3-Tigloyloxy-6-isovaleroyloxy-7- poisonous if ingested by humans or livestock hydroxytropane (Radford et al.,1964). However, its small quantity 11) Scopolamine is used for medicinal purposes (King 1984, 12) Tropinone Mann 1992). The larvicidal effects of this plant 13) Scopine against the rust-red flour beetle Tribolium 14) 6-Hydroxyacetoxytropane castaneum (Herbst) (Coleoptera: Tenebrionidae) 15) 3,6-Diacetoxytropane were also observed (Pascual-Villalobos and 16) 3-Tigloxyloxy-6-acetoxytropane Robledo, 1997). It can produce a number of 17) 3-Tigloyloxy-2-methylbutyryloxytropane amino acids particularly alanine, glutamate, 18) 3á,6â-Ditiglotoxytropane phenylalanine, and tyrosine. These amino acids 19) 3-Acetoxy-6-isobutyryloxytropan can be incorporated into the seed protein. The 20) 3-(2-Phenylpropionyloxy) tropane bulk of the amino acids incorporated into the 21) Littorine seed protein must, however, be supplied by adult 22) 6-Hydroxyapoatropine in the proximity of the , either as 23) 3â,6â-Ditigloyloxy-7-hydroxytropane the amino acids themselves, or their immediate 24) 3-Tropoyloxy-6-acetoxytropane precursors. The major free amino- acid products 25) 3,6-Dihydroxytropane of leaves are the amides asparagines and 26) 3â-Tigloyloxytropane glutamine (Lewis et al., 1970). 27) 3-Tigloyloxy-6-propionyloxy-7- hydroxytropane Phytochemistry of Datura stramonium 28) 3á-Apotropoyloxytropane Sixty-four tropane alkaloids have been detected 29) Aposcopolamine from D. stramonium. Two new tropane alkaloids, 30) 3â,6â-Ditigloyloxytropane 3-phenylacetoxy-6, 7-epoxynortropane and 7- 31) 3-(3'-Acetoxytropoyloxy) tropane hydroxyapoatropine were tentatively identified. 32) 3á-Tigloyloxy-6-hydroxytropane The alkaloids scopoline, 3-(hydroxyacetoxy) 33) Tropine tropane, 3-hydroxy-6-(2-methylbutyryloxy) 34) 3-Acetoxytropane tropane, 3â-tigloyloxy-6-hydroxytropane, 3,7- 35) 3-Hydroxy-6-acetoxytropane dihydroxy-6-tigloyloxytropane, 3-tigloyloxy-6- 36) 3-Hydroxy-6-methylbutyryloxytropane propionyloxytropane, 3-phenylacetoxy-6,7- 37) 3-Tigloloxy-6-isobutyryloxytropane epoxytropane, 3-phenylacetoxy-6-hydroxytropane, 38) Aponorscopolamine aponorscopolamine, 3â,6â-ditigloyloxytropane and 39) 7-Hydroxyhyoscyamine 40) Meteloidine 41) 3â,6â-Ditigloyloxytropane - 140 - Neurotoxic and Medicinal Properties of......

Table no. 2 : Alkaloid contents (ìg/mg) in Datura stramonium (Elisabetta Miraldi et al., 2001).

Samples Young plants Adults plants Atropine Scopolamine Atropine Scopolamine

Small leaves 0.156 ± 0.008 0.073 ± 0.001 0.165 ± 0.006 0.016 ± 007 Medium leaves 0.831 ± 0.014 0.041 ± 0.005 0.150 ± 0.002 0.022 ± 0.005 Big leaves 0.228 ± 0.014 0.035 ± 0.009 0.134 ± 0.004 0.044 ± 0.006 Stems 0.915 ± 0.015 0.129 ± 0.014 0.001 ± 0.001 -- Roots 0.121 ± 0.015 0.014 ± 0.004 -- -- buds -- Open flowers -- 0.299 ± 0.021 0.106 ± 0.031 0.270 ± 0.026 0.066 ± 0.004 Immature fruits -- Mature fruits -- Pericarp 0.001 ± 0.001 -- 0.001 ± 0.001 -- Seeds 0.670 ± 0.003 0.012 ± 0.001 0.387 ± 0.015 0.089 ± 0.010

The toxins in Jimson weed are tropane frequently given to pregnant mother with belladonna alkaloids, which possess strong asthmatic complaints (Pretorius andMarx, 2006). anticholinergic properties. These alkaloids It is used as a medicinal, psychotropic, sacred include: hyoscyamine (leaves, roots, seeds), & antispasmodic (Kulkarni SK, 2005; Kirtikar & hyoscine (roots); atropine (d,l-hyoscyamine) and Basle,1784; Evans et al.,1996; T.Oshima et scopolamine (l-hyoscine), as well as sitosterol and al.,1989). It is used for asthma, burns, ulcers, proteins (Friedman and Levin,1989;Chang et sinus infection, headaches, sores ( Mitchell & al.,1999). It is reported that hyoscyamine is the MH Ahmad, 2006). DS is used recreationally predominant alkaloid in DS from the line of for its central anticholinergic effects and is flowering (Evans et al., 1989; Bruni In, 1999; made easily into an extract by boiling the Osshima et al.,1989). Thorn apple leaves contains crushed seeds. The extract has rapid onset of 0.2%-0.45% of total alkaloids, seeds effects and may be useful for treatment of approximately 0.2% (Evans et al.,1989).The organophosphate poisoning (Theodore et al., contain a methylated nitrogen 2004). DS is a medicinal plant with atom (N-CH3) and include the anticholinergic antinociceptive (Abdollahi et al., 2003) antioxidant drugs, atropine, hyoscyamine, and scopolamine as (Couladis et al., 2003), hypolipidemic (Resekh et well as the narcotic cocaine (Fan Dang, 2005). al., 2001), anti-inflammatory, anti-rheumatoid Medicinal properties of D.stramonium (Tariq et al.,1989), and hypoglycemic properties (Gharaibeh et al.,1988). D.stramonium is used frequently as an anti- asthmatic treatment (Muller,1998,Weitz, 2003 & Pharmacological activity Ertekin et al.,2005). The widely reported D.stramonium seed extract has an analgesic medicinal uses include the use of the dried effect on both acute & chronic pain which were leaves of the plant as an anti-asthmatic agent produced by hot plate and formalin tests. It is (John,1984; Sezik et al., 1992; De Foe and likely that, this effect can be attributed to the Senatore, 1993). As the cure for the asthma alkaloid which interact with system mixture of the leaves and seeds is taken orally (Khalili et al., 2004).The whole plant is toxic, as a decoction or smoke. (Hirschmann et al., particularly the foliage & seeds. The 1990). Aqueous extract of the seeds are anticholinergic syndrome results from the reported to be used in the treatment of gastric inhibition of central and peripheral muscarinic pains and indigestion (Bhattarai, 1993). neurotransmission. The patient presents with dry Furthermore, this plant as herbal remedy is also skin and mucosa, flushing, with loss of

- 141 - Neurotoxic and Medicinal Properties of...... accommodation that causes blurred vision and haemagglutinin or lectin. The extract is capable , altered mental status, hyperpyrexia, of agglutinating erythrocytes from several species, sinus , , myoclonic and is non-specific with regard to human ABO jerking. Other symptoms may include ataxia, blood groups (Kalpatrick et al., 1978). Laboratory impaired short-term memory, disorientation, monitoring of changes in some blood parameters , hallucinations, , agitated in horses intoxicated with jimsonweed was carried delirium, seizures, coma, respiratory failure and out. It was established that the intoxication was cardiovascular collapse (Alberto et al., 2001). Its accompanied by hyperchromaemic, anticholinergic compounds are likely to produce erythrocytosis, leukocytosis, neutrophilia and delirium and stupor but rarely cause deep coma regenerative shift, lymphocytopenia, (Ohernodorfer et al., 2002).The ethanolic extracts aneosinophilia, increased haematocrit values and obtained from both and seed in the thorn low erythrocyte sedimentation rate (Binev et al., apple were investigated for acaricidal, repellent 2006). All parts of the plant are toxic but the highest and oviposition deterrent properties against adult amount of the alkaloids is contained in ripe seeds two-spotted spider mites (Tetranychus urticae (Chang et al.,1999; De Frates, 2005).They act as Koch) under laboratory conditions. Leaf & seed competitive antagonist of at extracts, which were applied in 167,250 and peripheral and central muscarinic receptor sites 145,750 mg/l concentrations, respectively caused (Dugan et al.,1989). Poisoning results in 98% and 25 % mortality among spider mite widespread paralysis of parasympathetic adults after 48 h (Nabi et al., 2009). Exposure of innervated organs.(Friedman et al.,1989). Datura the foetus to this plant when a mother uses it aqueous leaf extract-induced cytotoxicity & for asthma, will cause a continuous release of oxidative stress in human cancer cell lines Ach, resulting in the desensitizing of nicotinic (Ahmad, 2009). Severe toxicity has been receptors, this could ultimately result in associated with coma and seizures, although death permanent damage to the foetus (Pretorius and is rare (Dewitt et al.,1997). Marx, 2006). Conclusion The main effects of jimsonweed seeds were: The current review demonstrated that the whole decreased body weight gain, serum alkaline part of DS has got many uses and toxicity to a phosphatase and blood urea nitrogen. Female rats greater extent. This plant has been used in curing showed more marked responses to jimson weed different types of diseases. The alkaloids isolated seed than did males. In addition to the effects seen from the plants are also found to be toxic to the in both sexes, the females developed decreased animals and 48 alkaloids have been determined. serum total protein and cholesterol, and increase Two new tropane alkaloids, 3- phenylacetoxy-6,7- serum glutamic, pyruvic transaminase and epoxynortropane and 7-hydroxyapoatropine were chloride, red blood cell count, haemoglobin also identified. The outcome of this review work concentration and packed red cell volume (Dugan may facilitate the enrichment of concept and the et al.,1989). An extract prepared from the seeds possible outcome from the use and consumption of the DS possess activity typical of a protien of D. stramonium.

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