Datura stramonium: An overview of its phytochemistry and pharmacognosy

Langonjam Rajeep Singh, Okram Mukherjee Singh*

Department of Chemistry, Manipur University, Canchipur, Imphal-795003, Manipur, India

ABSTRACT:

Datura stramonium (Solanaceae) is an important medicinal plant from which tropane alkaloids, amino acids, tannin, phytic acids, carbohydrates have been isolated. Its diverse biological activities include anti-asthmatic, antibacterial, antifungal, anti-inflammatory, larvacidal, antispasmodic, antioxidant, antinociceptive, anti-rheumatoid and anti-ulcer activities. It is used in indigenous and traditional folk medicine system in almost all parts of the World. The present review is focused on the phytochemical and pharmacological studies of the Datura stramonium.

KEYWORDS: Datura stramonium, alkaloids, analgesic activity, antibacterial activity.

1. INTRODUCTION

Manipur, a tiny state in the North-East corner of India and a distinct division of the Indo-Burma Hotspot is listed in the 25 biodiversity hotspots of the world. It is considered as a treasure house of plant, animal and microbial resources. Recently we have reported the phytochemicals and medicinal applications of certain plants which are distributed as wild plants in both the valley and hill areas of Manipur^1-3. An overview on the phytochemistry and pharmacognsy of Datura stramonium (Figure-1), which is grown in Manipur, is presented here.

Fig. 1. Datura stramonium

2. DESCRIPTION:

Datura stramonium is commonly known as jimson weed or thorn apple. It is a medicinal plant⁴ with a broad range of medicinal applications such as antinociceptive⁵, antioxidant⁶, hypolipidemic⁷, anti-rheumatoid⁸ and hypoglycemic⁹ properties. Dried leaves of Datura stramonium is used to cure asthma¹⁰. It grows to a height of 2-4 feet and commonly reaching a diameter of 4-6 feet. The flowers are large and corollas are 6 cm long. The fruit is a large, four ovaled ovate capsule, very thorny and contains numerous black to dark brown seeds. The stems are simple, stout and mostly erect. The leaves are large, approximately 20 cm long and oval like with a wavy and coarsely dentate margin. The root is long, thick and tapering and somewhat branched.

3. DISTRIBUTION:

The species of Datura can be found throughout the world. The plant grows in sandy flats, plains, areas up to 2,500 feet above sea level. The origin of Datura Stramonium is disputed. The Sanskrit dhattura and the Hindustani dhatur formed the basis of the general name, the origin of Jimson weed could be Asiatic. Some sources report a probable Central American origin, due to Datura’s habitation of most temperate and Subtropical parts of the world. It is indigenous to India and grows abundantly throughout the Himalayas from Kashmir to Sikkim. In Manipur, it is grown as a wild plant and distributed throughout the hills and valleys. In Manipur, it is generally grown in April – October¹¹.

4. CHEMICAL CONSTITUENTS:

Plant contains 0.2- 0.6% alkaloids. The main alkaloids are hyoscyamine and hyoscine (scopolamine). It also contains protein albumin and atropine. Atropine is formed from hyoscyamine by racemisation. These alkaloids are usually present in the proportion of about two parts of hyoscyamine to one part of hyoscine, but in young plants hyoscine is predominant alkaloid. Ditiglyol esters of 3,6-dihydroxytropane and 3,6,7-trihydroxytropane have been isolated from the roots in addition to hyoscine, hyoscyamine, tropine and pseudotropine. It also contains 6-hydroxyhyoscymine, skimmianine, metelodine, acetyl derivatives of caffeic, p-coumaric and ferulic acid, stigmasterol, campesterol, with anolide I, steroidal glycosides, daturataturins A and B, flavonoids, chrysins, quercetin and their esters. Withastramonolide and coumarins (umbelliferon and scopolin) are also present in the plant. The seeds contain oil, wax, resin, extractive, gummy matter, malic acid, some salts and a peculiar alkaloid which has been named Daturia^12-29. The main alkaloids found in Datura satramonium are shown in figure 2.

Table 1. List of Compounds Extracted from Datura stramonium

Entry	Compound	Sources	Country	Ref.
1	3-acetoxytropane	R, ST	Bulgaria	13
2	3-acetoxy-6-isobutyryloxytropane	R, ST, L, P	Bulgaria	16
3	3α-apotropoyloxytropane	R, L, ST	Bulgaria	17
4	3β-apotropoyloxytropane	S	Bulgaria	17
5	Aponorscopolamine	ST, L, P	Bulgaria	18
6	Aposcopolamine	R, ST, L, P, S	Bulgaria	13
7	3-(3-acetoxytropoyloxy)tropane	R, ST, L	Bulgaria	19
8	3-acetoxy-6-hydroxytropane	R	Bulgaria	17
9	3,6-diacetoxytropane	R	Bulgaria	20
10	3,7-dihydroxy-6-tigloyl-oxytropane	S	Bulgaria	21
11	3α,6β-ditigloyloxytropane	R, ST	Bulgaria	22
12	3β,6β-ditigloyloxytropane	R	Bulgaria	22
13	3α,6β-ditigloyloxy-7-hydroxytropane	R, ST	Bulgaria	13
14	3β,6β-ditigloyloxy-7-hydroxytropane	R	Bulgaria	19
15	3,6-disubstitutedtropanes	R, ST	Bulgaria	22
16	3,7-dihydroxy-6 propionyloxytropane	Plant	Morocco	23
17	6,7-dehydro-3-tigloyloxytropane	Plant	Morocco	23
18	3,7-dihydroxy-6-(2’-methylbutyryloxy)tropane	Plant	Morocco	23
19	6,7-dehydroapoatropine	Plant	Morocco	23
20	Hygrine	ST	Bulgaria	13
21	3-(hydroxyacetoxy)tropane	ST, R	Bulgaria	24
22	6-hydroxyacetoxytropane	R	Bulgaria	22
23	3-hydroxy-6-acetoxytropane	R, ST	Bulgaria	20
24	3-hydroxy-6-(2-methylbutyryloxy)tropane	L	Bulgaria	13
25	3-hydroxy-6-tigloyloxytropane	R, ST, L, P	Bulgaria	13
26	Hyoscyamine	R, ST, L, S	Bulgaria	13
27	6-hydroxyapoatropine	R, ST, L	Bulgaria	22
28	7-hydroxyhyoscyamine	ST, L	Bulgaria	23
29	6-hydroxyhyoscyamine	R, ST, L	Bulgaria	22
30	Littorine	R, ST, L, S	Bulgaria	24
31	Meteloidine	R, P	Bulgaria	13
32	3-monosubstitutedtropanes	R, L	Bulgaria	13, 22
33	3-(3^’-methoxytropoyloxy)tropane	Plants	Morocco	23
34	Methylscopolamine	Plants	Bulgaria	17
35	Phenylacetoxytropane	R, ST, L, S	Bulgaria	22
36	3-phenylacetoxy-6,7-epoxytropane	R, ST, L, P	Bulgaria	25
37	3-(2^’-phenylpropionyloxy)tropane	L	Bulgaria	26
38	3-phenylacetoxy-6-hydroxytropane	R, ST	Bulgaria	24
39	3α-phenylacetoxytropane	S	Bulgaria	16
40	3β-phenylacetoxytropane	S	Bulgaria	17
41	Scopoline	S, L, ST, P	Bulgaria	22
42	Scopine	L, P, S	Bulgaria	22
43	Scopolamine	R, ST, L, P	Bulgaria	12
44	3-substituted-6,7-epoxytropanes	R, P, ST, S	Bulgaria	13, 22
45	Tropinone	S	Bulgaria	22
46	3α-tigloyloxytropane	ST, R	Bulgaria	13
47	3β-tigloyloxytropane	R	Bulgaria	13
48	3α-tigloyloxy-6-hydroxytropane	R, ST	Bulgaria	13
49	3β-tigloyloxy-6-hydroxytropane	R	Bulgaria	13
50	3-tigloyloxy-6-acetoxytropane	R	Bulgaria	13
51	3-tigloyloxy-6-propionyloxy-7-hydroxytropane	R, ST, L, P	Bulgaria	27
52	3-tigloyloxy-6-propionyloxytropane	R	Bulgaria	13
53	3-tigloyloxy-6-isobutyrloxytropane	R	Bulgaria	13
54	3-tigloyloxy-6-(2-methylbutyrloxy)tropane	R, ST	Bulgaria	13
55	3-tigloyloxy-2-methylbutyryloxytropane	R	Bulgaria	13
56	3α-tigloyloxy-6-isovaleryloxy-7-hydroxytropane	R	Bulgaria	28, 29
57	3β-tigloyloxy-6-isovaleryloxy-7-hydroxytropane	R	Bulgaria	28, 29
58	3-tropoyloxy-6-acetoxytropane	R, ST	Bulgaria	27
59	3,6,7-trisubstitutedtropanes	ST, L	Bulgaria	13, 22
60	Tropine	R, ST, L, S	Bulgaria	22
61	3-tigloyloxy-6,7-dihydroxytropane	R	Bulgaria	17
62	3-tigloyloxy-6-methylbutyryloxytropane	R	Bulgaria	13
63	3-tropoyloxytropane	R, L, S	Bulgaria	17
64	3-tropoyloxy-6,7-epoxynortropane	R	Bulgaria	17
65	3-tropoyloxy-6,7-epoxytropane	R, L, S	Bulgaria	17
66	3-tropoyloxy-6-hydroxytropane	R	Bulgaria	17
67	3-tropoyloxy-6-tigloyloxytropane	R	Bulgaria	17
68	3-tigloyloxy-6,7-epoxytropane	Plant	Morocco	23
69	3-tigloyloxy-6-isobutyryloxy-7-hydroxytropane	Plant	Morocco	23
70	3-tropoyloxy-6-isobutyryloxytropane	Plant	Morocco	23
71	3β-tropoyloxy-6β-isovaleroyloxytropane	Plant	Morocco	23

L = Leaves, R = Roots, S = Seeds, ST = Stems, P = Pericarp

Table-2.The Percentage (%) of various chemical compounds of Jimson Weed¹⁴

Entry	Constituent	(%) of unpurified Jimson weed seed flour
1	Nitrogen	3.1
2	Water	7.7
3	Fat	18.1
4	Fiber	17.8
5	Ash	6.6
6	Carbohydrate	31.9
7	Starch	1.1
8	Sugar	2.1
9	Reducing Sugar	0.3
10	Glucose	0.13

Table 3. Amino acid content of Jimson Weed seed flour¹⁴

Entry	Name of amino acids	Jimson Weed
1	Aspartic acid	7.74
2	Threonine	3.14
3	Serine	4.03
4	Glutamine	13.05
5	Proline	3.32
6	Glycine	3.87
7	Alanine	3.51
8	Valine	3.62
9	Cysteine	2.00
10	Methionine	1.38
11	Isoleucine	3.22
12	Leucine	5.31
13	Tyrosine	2.55
14	Phenylalanine	3.47
15	Histidine	1.84
16	Lysine	3.19
17	Arginine	6.54
18	Tryptophan	0.51

The major free amino acid products of leaves are asparagines and glutamine.

Table 4. Mineral content of thorn apple¹⁵

Mineral concentration (mg/g)

Mineral	Seed coat	Seeds	Whole seeds
Magnesium	399.20	344.07	307.49
Calcium	57.00	426.50	295.10
Lead	0.32	0.29	0.95
Chromium	0.60	0.60	2.85
Iron	6.92	6.93	5.63
Copper	10.36	6.22	8.07
Manganese	5.13	4.11	8.49
Zinc	8.25	3.23	0.51
Phosphorus	190.00	275.00	220.00
Potassium	1.93	2.04	2.50
Sodium	2.02	2.86	2.50

Fig : 2. Alkaloids isolated from Datura stramonium

5. BIOLOGICAL ACTIVITY:

Extracts of Datura stramonium are used in traditional systems of medicines. The plant as a whole possesses remarkable biological activities which are summarised below.

5.1. Antibacterial Activity:

The leave extract of Datura stramonium exhibits antibacterial activity. The antibacterial activity against the microorganism strains of Salmonella typhii, Pseudomonas aeruginosa, Proteus vulgaris in the alcoholic extract of the leaves Datura stramonium was found to be most efficient and moderately effective against Klebsiella pneumonia, Staphylococcus-aureus and Escherica coli. The different concentrations of the alcoholic extracts of Datura stramonium was proved to be effective and concentration dependant antimicrobial activity against Gram positive and Gram negative bacteria tested. This is also evidenced by several research groups and supporting the presence of antibacterial activity of Datura stramonium against Gram positive bacteria by dose dependent manner³⁰.

5.2. Nematicidal Activity:

Nidhi et al reported the efficient nematicidal activity of the aqueous extract prepared from the leaf of Datura stramonium³¹.

5.3. Antifungal activity:

It was reported that the leaf extract of Datura stramonium was found to exhibit excellent antifungal activity. K. Usha et al reported strong antifungal activity of a concoction brewed from Datura stramonium, Calotropis giganta and Azadirachta indica (neem) and cow manure followed by methanol-water (70/30 v/v) extracts of Datura stramonium, Calotropis gigantea and Azadirachata indica against Fusarium mangiferae³².

5.4. Contact toxicity:

Habib et al demonstrated that the leaf and seed extracts of Datura stramonium has contact toxicity against Tribolium castaneum adults³³.

5.5. Anticancer activity:

Ahmad et al studied a variety of human cancer cells derived from breast (MDA- MB231), head and neck (FaDu), and lung (A549) and were exposed for 24 and 48 hours to Datura aqueous leaf extract and clonogenic cell survival as well as parameters indicative of oxidative stress were assayed. Exposure of these cells to the extract for 48 hours showed that all cancer cell lines were sensitive to cell killing induced by Datura aqueous leaf extract exposure with some variability (p<0.05)³⁴.

5.6. Antioxidant activity:

Kumar et al studied antioxidant activity of Datura stramonium and was carried out by inhibition of lipid peroxidation technique. Alkaloid contents were varied from 24.6 and 63.3 mg g^-1 in the extracts. Flavonoid contents were between 23.15 and 63.3 mg g^-1 in the methalonic extract of the Datura stramonium. It was reported that Flavonoids are a group of polyphenic compounds with known properties which include free radical scavenging, inhibition of hydrolytic oxidative enzymes and anti- inflammatory activity. It has been recognised that alkaloids and flavonoids show antioxidant activity and their effects on human nutrition and health care are considerable³⁵.

5.7. Antimicrobial activity:

Mukesh et al studied the anti-microbial activity of combined crude ethanolic extract of Datura stramonium, Terminalia arjuna and Withania somnifera in cup plate diffusion method for antibacterial and antifungal activity. The extracts were subjected to screening to detect potential antimicrobial activity against Staphylococcus aureus, Bacillus subtilus, Escherichia coli, K. pneumonia, M. luteus and C. albicans comparing with Ciprofloxacin standard drug. Minimum inhibitory concentrations (MIC) of the extracts were also determined against the four selected microorganisms showing zones of inhibition =10mm. Antiinflammatory activity and analgesic activity of both aqueous and alcoholic extracts revealed significant effects (p<0.01) against thermal, chemical and forced induced stimuli in hot plate, tail immersion and tail clip method respectively as well as significant anti-inflammatory effects³⁶.

5.8. Acarcidal, repellent and oviposition deterrent activity:

Nabi Alper Kumral et al investigated the ethanol extracts obtained from both leaf and seed for acaricidal, repellent and oviposition deterrent properties against adult two-spotted spider mites (Tetranychus urticae Koch) (Acari: Tetranychidae) under laboratory conditions. Leaf and seed extracts, which were applied in 167,250 and 145,750 mg/l concentrations, respectively (using a Petri leaf disc-spray tower method), caused 98 and 25% mortality among spider mite adults after 48 h³⁷.

5.9. Toxicological evaluation of Datura stramonium in rats:

Dugan et al studied diets containing 0.5, 1.58 and 5.0% jimson weed seed were fed to male and female rats (20/group) in a 90-day subchronic feeding study. The alkaloid content was 2.71 mg atropine and 0.66 mg scopolamine/g of seed. Gross clinical observations, body weights and feed and water intakes were recorded weekly. They reported that the principal effects of jimson weed seed were: decreased body-weight gain, serum albumin and serum calcium; increased liver and testes weights (as a percentage of body weight), serum alkaline phosphatase and blood urea nitrogen. Female rats showed more marked responses to jimson weed seed than did males. In addition to the effects seen in both sexes, the females developed decreased serum total protein and cholesterol, and increased serum glutamic-pyruvic transaminase and chloride, red blood cell count, haemoglobin concentration and packed red cell volume. No histological lesions were associated with ingestion of jimson weed seed at 5.0%. It was concluded that jimson weed seed at concentrations of 0.5% or more in the diet produced adverse physiological changes in rats³⁸.

5.10. Allelopathic potential of the essential oil from Datura stramonium L.:

You et al analyzed the chemical composition of the essential oil from Datura Stramonium and determined their phytotoxic activity on five cultivated crops. The main components of essential oil were sterols and their derivatives, and the major constituents were 5α-Ergosta-7,22-dien-3β-ol (16.53%), 3-Hydroxycholestan-5-yl, acetate (14.97%), and 26,26-Dimethyl-5,24(28)-ergostadien-3β-ol (10.39%). The essential oil and its aqueous saturated solution significantly inhibited the germination and growth of lettuce, radish, common bean, maize, and cucumber. The results indicated that D. Stramonium may release allelochemicals, both water-soluble and volatile compositions, into environment to inhibit other plant species³⁹.

5.11. Datura stramonium poisoning in horses:

Nikolov et al studied the clinical signs manifested after intoxication with Jimson weed in horses and results were: hyperthermia, tachycardia, polypnoea with dyspnoea, acute gastric dilatation, secondary intestinal gas accumulation, mydriasis, dry mucosae, complete refusal of feed, and lack of thirst, defecation and urination⁴⁰.

6. The traditional uses of Datura stramonium:

In Europe the plant was used for witch craft, in ointments. Throughout most European countries the seeds were used to brew beer. In Mexico various tribes (i.e. Opata, Seri) used in religious ritiuals. Datura stramonuim was thought to be one of two plants identified in 4,000 year old rock paintings throughout the Pecos river region of Texas and northern Mexico, used by Huichol Indians along with peyote to commune with the spirit world. Hernandez reported that the Aztecs applied a decoction of leaves to the body for fever or administered as a suppository. The fruit and leaves were considered good for pain in the chest. If too much was taken, it was believed to cause insanity. In north western New Spain, the Opata tribes used to rub Datura leaf of on the painfull area for spleen disease. The traditional uses of Datura stramonium in different parts of the world are listed in the table 5.

Table-5. The traditional uses of Datura stramonium in different parts of the world

Entry	Countries	Traditional uses of Datura stramonium	References
1	India	Fruit is burnt and ash is given orally with honey in bronchitis and asthma.	41
2	Pakistan	Green Leaves are used for softening the boils. The juice of flower is useful for earache.	42
3	Bulgaria	It is used as antiasthmatic, spasmolytic and antiviral remedy.	43
4	Rwanda	It is used for acarcidal activity.	44
5	Ethiopia	It is used for wound treatment against wound causing bacteria.	45

7. CONCLUSION:

The phytochemistry and pharmacognosy of Datura stramonium has been well documented in this brief review. In view of its multiple uses, more activity screening and structural relationship studies are yet to explore further. The informations presented in this review would be helpful in promoting research aiming at the search and development of new agents for medical application and agro industries based on natural products derived from plants.

8. ACKNOWLEDGMENT:

We are thankful to the UGC, New Delhi [project No.39-711/2010(SR)] for financial assistance.

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Received on 21.02.2013

Modified on 04.03.2013

Accepted on 03.04.2013

© A&V Publication all right reserved

Research Journal of Pharmacognosy and Phytochemistry. 5(3): May-June 2013, 143-148