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Datura stramonium: An overview of its phytochemistry and pharmacognosy

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Research J. Pharmacognosy and Phytochemistry 2013; 5(3): 143-148 O. M. Singh, et al.

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
ISSN 0975- 2331 isolated. Its diverse biological activities include anti-asthmatic, antibacterial,
Research Journal of Pharmacognosy antifungal, anti-inflammatory, larvacidal, antispasmodic, antioxidant,
and Phytochemistry. 5(3): May-June antinociceptive, anti-rheumatoid and anti-ulcer activities. It is used in
2013, 143-148 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.

Review Article 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 Manipur1-3. An overview on the phytochemistry and
pharmacognsy of Datura stramonium (Figure-1), which is grown in
Manipur, is presented here.

*Corresponding Author:
Okram Mukherjee Singh,
Department of Chemistry,
Manipur University, Canchipur,
Imphal-795003, Manipur, India
Email: ok_mukherjee@yahoo.co.in

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
Received on 21.02.2013 large, four ovaled ovate capsule, very thorny and contains numerous black to
Modified on 04.03.2013 dark brown seeds. The stems are simple, stout and mostly erect. The leaves
Accepted on 03.04.2013 are large, approximately 20 cm long and oval like with a wavy and coarsely
© A&V Publication all right reserved dentate margin. The root is long, thick and tapering and somewhat branched.
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Research J. Pharmacognosy and Phytochemistry 2013; 5(3): 143-148 O. M. Singh, et al.

3. DISTRIBUTION: hyoscyamine by racemisation. These alkaloids are usually


The species of Datura can be found throughout the world. present in the proportion of about two parts of hyoscyamine
to one part of hyoscine, but in young plants hyoscine is
The plant grows in sandy flats, plains, areas up to 2,500 feet
above sea level. The origin of Datura Stramonium is predominant alkaloid. Ditiglyol esters of 3,6-
disputed. The Sanskrit dhattura and the Hindustani dhatur dihydroxytropane and 3,6,7-trihydroxytropane have been
formed the basis of the general name, the origin of Jimson isolated from the roots in addition to hyoscine,
weed could be Asiatic. Some sources report a probable hyoscyamine, tropine and pseudotropine. It also contains 6-
Central American origin, due to Datura’s habitation of mosthydroxyhyoscymine, skimmianine, metelodine, acetyl
temperate and Subtropical parts of the world. It is derivatives of caffeic, p-coumaric and ferulic acid,
indigenous to India and grows abundantly throughout the stigmasterol, campesterol, with anolide I, steroidal
Himalayas from Kashmir to Sikkim. In Manipur, it is grown glycosides, daturataturins A and B, flavonoids, chrysins,
as a wild plant and distributed throughout the hills and quercetin and their esters. Withastramonolide and
valleys. In Manipur, it is generally grown in April – coumarins (umbelliferon and scopolin) are also present in
October11. the plant. The seeds contain oil, wax, resin, extractive,
gummy matter, malic acid, some salts and a peculiar
4. CHEMICAL CONSTITUENTS: alkaloid which has been named Daturia12-29. The main
Plant contains 0.2- 0.6% alkaloids. The main alkaloids are alkaloids found in Datura satramonium are shown in figure
hyoscyamine and hyoscine (scopolamine). It also contains 2.
protein albumin and atropine. Atropine is formed from
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

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Research J. Pharmacognosy and Phytochemistry 2013; 5(3): 143-148 O. M. Singh, et al.

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 The major free amino acid products of leaves are
Jimson Weed14 asparagines and glutamine.
Entry Constituent (%) of unpurified
Jimson weed seed flour
Table 4. Mineral content of thorn apple15
1 Nitrogen 3.1
Mineral concentration (mg/g)
2 Water 7.7
Mineral Seed coat Seeds Whole seeds
3 Fat 18.1
4 Fiber 17.8 Magnesium 399.20 344.07 307.49
Calcium 57.00 426.50 295.10
5 Ash 6.6
Lead 0.32 0.29 0.95
6 Carbohydrate 31.9
7 Starch 1.1 Chromium 0.60 0.60 2.85
Iron 6.92 6.93 5.63
8 Sugar 2.1
Copper 10.36 6.22 8.07
9 Reducing Sugar 0.3
10 Glucose 0.13 Manganese 5.13 4.11 8.49
Zinc 8.25 3.23 0.51
Phosphorus 190.00 275.00 220.00
Table 3. Amino acid content of Jimson Weed seed flour14 Potassium 1.93 2.04 2.50
Entry Name of amino acids Jimson Weed Sodium 2.02 2.86 2.50
1 Aspartic acid 7.74
2 Threonine 3.14
3 Serine 4.03 H3C H3C
N N
4 Glutamine 13.05
5 Proline 3.32
6 Glycine 3.87 O
7 Alanine 3.51
8 Valine 3.62 H H H H
9 Cysteine 2.00 HOH2C O HOH2C O
10 Methionine 1.38
11 Isoleucine 3.22
O O
12 Leucine 5.31
13 Tyrosine 2.55
14 Phenylalanine 3.47
15 Histidine 1.84
16 Lysine 3.19 (-)-Hyoscyamine (-)-Scopolamine
17 Arginine 6.54 Fig : 2. Alkaloids isolated from Datura stramonium
18 Tryptophan 0.51

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Research J. Pharmacognosy and Phytochemistry 2013; 5(3): 143-148 O. M. Singh, et al.

5. BIOLOGICAL ACTIVITY: 24.6 and 63.3 mg g-1 in the extracts. Flavonoid contents
Extracts of Datura stramonium are used in traditional were between 23.15 and 63.3 mg g-1 in the methalonic
systems of medicines. The plant as a whole possesses extract of the Datura stramonium. It was reported that
remarkable biological activities which are summarised Flavonoids are a group of polyphenic compounds with
below. known properties which include free radical scavenging,
inhibition of hydrolytic oxidative enzymes and anti-
5.1. Antibacterial Activity: inflammatory activity. It has been recognised that alkaloids
The leave extract of Datura stramonium exhibits and flavonoids show antioxidant activity and their effects
antibacterial activity. The antibacterial activity against the on human nutrition and health care are considerable35.
microorganism strains of Salmonella typhii, Pseudomonas
aeruginosa, Proteus vulgaris in the alcoholic extract of the 5.7. Antimicrobial activity:
leaves Datura stramonium was found to be most efficient Mukesh et al studied the anti-microbial activity of
and moderately effective against Klebsiella pneumonia, combined crude ethanolic extract of Datura stramonium,
Staphylococcus-aureus and Escherica coli. The different Terminalia arjuna and Withania somnifera in cup plate
concentrations of the alcoholic extracts of Datura diffusion method for antibacterial and antifungal activity.
stramonium was proved to be effective and concentration The extracts were subjected to screening to detect potential
dependant antimicrobial activity against Gram positive and antimicrobial activity against Staphylococcus aureus,
Gram negative bacteria tested. This is also evidenced by Bacillus subtilus, Escherichia coli, K. pneumonia, M. luteus
several research groups and supporting the presence of and C. albicans comparing with Ciprofloxacin standard
antibacterial activity of Datura stramonium against Gram drug. Minimum inhibitory concentrations (MIC) of the
positive bacteria by dose dependent manner30. extracts were also determined against the four selected
microorganisms showing zones of inhibition =10mm.
5.2. Nematicidal Activity: Antiinflammatory activity and analgesic activity of both
Nidhi et al reported the efficient nematicidal activity of aqueous and alcoholic extracts revealed significant effects
the aqueous extract prepared from the leaf of Datura (p<0.01) against thermal, chemical and forced induced
stramonium31. stimuli in hot plate, tail immersion and tail clip method
respectively as well as significant anti-inflammatory
5.3. Antifungal activity: effects36.
It was reported that the leaf extract of Datura stramonium
was found to exhibit excellent antifungal activity. K. Usha 5.8. Acarcidal, repellent and oviposition deterrent
et al reported strong antifungal activity of a concoction activity:
brewed from Datura stramonium, Calotropis giganta and Nabi Alper Kumral et al investigated the ethanol extracts
Azadirachta indica (neem) and cow manure followed by obtained from both leaf and seed for acaricidal, repellent
methanol-water (70/30 v/v) extracts of Datura stramonium, and oviposition deterrent properties against adult two-
Calotropis gigantea and Azadirachata indica against spotted spider mites (Tetranychus urticae Koch) (Acari:
Fusarium mangiferae32. Tetranychidae) under laboratory conditions. Leaf and seed
extracts, which were applied in 167,250 and 145,750 mg/l
5.4. Contact toxicity: concentrations, respectively (using a Petri leaf disc-spray
Habib et al demonstrated that the leaf and seed extracts of tower method), caused 37
98 and 25% mortality among spider
Datura stramonium has contact toxicity against Tribolium mite adults after 48 h .
castaneum adults33.
5.9. Toxicological evaluation of Datura stramonium in
5.5. Anticancer activity: rats:
Ahmad et al studied a variety of human cancer cells Dugan et al studied diets containing 0.5, 1.58 and 5.0%
derived from breast (MDA- MB231), head and neck jimson weed seed were fed to male and female rats
(FaDu), and lung (A549) and were exposed for 24 and 48 (20/group) in a 90-day subchronic feeding study. The
hours to Datura aqueous leaf extract and clonogenic cell alkaloid content was 2.71 mg atropine and 0.66 mg
survival as well as parameters indicative of oxidative stress scopolamine/g of seed. Gross clinical observations, body
were assayed. Exposure of these cells to the extract for 48 weights and feed and water intakes were recorded weekly.
hours showed that all cancer cell lines were sensitive to cell They reported that the principal effects of jimson weed seed
killing induced by Datura aqueous leaf extract exposure were: decreased body-weight gain, serum albumin and
with some variability (p<0.05)34. serum calcium; increased liver and testes weights (as a
percentage of body weight), serum alkaline phosphatase
5.6. Antioxidant activity: and blood urea nitrogen. Female rats showed more marked
Kumar et al studied antioxidant activity of Datura responses to jimson weed seed than did males. In addition
stramonium and was carried out by inhibition of lipid to the effects seen in both sexes, the females developed
peroxidation technique. Alkaloid contents were varied from decreased serum total protein and cholesterol, and increased

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Research J. Pharmacognosy and Phytochemistry 2013; 5(3): 143-148 O. M. Singh, et al.

serum glutamic-pyruvic transaminase and chloride, red Table-5. The traditional uses of Datura stramonium in different
blood cell count, haemoglobin concentration and packed parts of the world
Entry Countries Traditional uses of References
red cell volume. No histological lesions were associated
Datura stramonium
with ingestion of jimson weed seed at 5.0%. It was 1 India Fruit is burnt and ash is 41
concluded that jimson weed seed at concentrations of 0.5% given orally with honey
or more in the diet produced adverse physiological changes in bronchitis and
in rats38. asthma.
2 Pakistan Green Leaves are used 42
for softening the boils.
5.10. Allelopathic potential of the essential oil from The juice of flower is
Datura stramonium L.: useful for earache.
You et al analyzed the chemical composition of the 3 Bulgaria It is used as 43
essential oil from Datura Stramonium and determined their antiasthmatic,
phytotoxic activity on five cultivated crops. The main spasmolytic and
antiviral remedy.
components of essential oil were sterols and their 4 Rwanda It is used for acarcidal
44
derivatives, and the major constituents were 5α-Ergosta- activity.
7,22-dien-3β-ol (16.53%), 3-Hydroxycholestan-5-yl, acetate 5 Ethiopia It is used for wound
45
(14.97%), and 26,26-Dimethyl-5,24(28)-ergostadien-3β-ol treatment against
(10.39%). The essential oil and its aqueous saturated wound causing bacteria.
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
7. CONCLUSION:
species39.
The phytochemistry and pharmacognosy of Datura
stramonium has been well documented in this brief review.
5.11. Datura stramonium poisoning in horses:
In view of its multiple uses, more activity screening and
Nikolov et al studied the clinical signs manifested after
structural relationship studies are yet to explore further. The
intoxication with Jimson weed in horses and results were:
informations presented in this review would be helpful in
hyperthermia, tachycardia, polypnoea with dyspnoea, acute
promoting research aiming at the search and development
gastric dilatation, secondary intestinal gas accumulation,
of new agents for medical application and agro industries
mydriasis, dry mucosae, complete refusal of feed, and lack
40 based on natural products derived from plants.
of thirst, defecation and urination .
8. ACKNOWLEDGMENT:
6. The traditional uses of Datura stramonium: We are thankful to the UGC, New Delhi [project No.39-
In Europe the plant was used for witch craft, in ointments.
711/2010(SR)] for financial assistance.
Throughout most European countries the seeds were used to
brew beer. In Mexico various tribes (i.e. Opata, Seri) used
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