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Argemone mexicana: Chemical and pharmacological aspects *

Article  in  Revista Brasileira de Farmacognosia · May 2013

DOI: 10.1590/S0102-695X2013005000021

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 Revista Brasileira de Farmacognosia
Brazilian Journal of Pharmacognosy
Argemone mexicana: chemical and 23(3): 559-575, May/Jun. 2013

pharmacological aspects#
Goutam Brahmachari,* Dilip Gorai, Rajiv Roy

Laboratory of Natural Products & Organic Synthesis, Department of Chemistry,

Visva-Bharati University, West Bengal, India.
Review
Abstract: The Papaveraceae, informally known as the poppy family, are an
ethnopharmacologically important family of 44 genera and approximately 760
species of flowering plants. The present work offers a review addressing the Received 16 Oct 2012
detailed chemistry and pharmacology of Argemone mexicana L. regarded as one Accepted 6 Feb 2013
of the most significant plant species in traditional system of medicine. The plant is Available online 5 Mar 2013
used in different parts of the world for the treatment of several ailments including
tumors, warts, skin diseases, inflammations, rheumatism, jaundice, leprosy, Keywords:
microbial infections, and malaria. Interestingly, the plant is the source of a diverse Argemone mexicana
biological activity
kind of chemical constituents although alkaloids are mostly abundant. Beyond
Papaveraceae
pharmaceutical efficacies, certain plant parts also show toxic effects as well. pharmaceutical potential
Hence, an up-to-date information on the chemical and pharmacological knowledge phytochemical constituents
on this plant may be helpful to guide researchers anticipating to undertake further traditional uses
investigations in these directions. The present review covers literature up to 2012
and enlists 111 references. ISSN 0102-695X
DOI: 10.1590/S0102-695X2013005000021

Introduction et al., 2007). Leaves and seeds are also reported to find
application in maintaining normal blood circulation and
Argemone mexicana L., known as Ghamoya (class: cholesterol level in human body (Albuquerque et al.,
Magnoliopsida Dicotyledons; subclass: Magnoliidae; 2007); these plant parts possess anti-venom property
order: Papaverales; family: Papaveraceae; Figure 1) is as well (Makhija & Khamar, 2010; Minu et al., 2012).
an exotic weed indigenous in South America but has Flowers are found to be expectorant and have been used
widespread distribution in many tropical and sub-tropical in the treatment of coughs (Brahmachari et al., 2010). In
countries including West Africa (Ibrahim & Ibrahim, Brazil, the plant is commonly known as ‘cardo-santo’ and
2009). This plant is common everywhere by roadsides and used traditionally in the treatment of a number of diseases
fields in India as well (Bhalke & Gosavi, 2009). The plant (Agra et al., 2007; 2008; Bieski et al., 2012). Seeds of the
is an erect prickly annual herb of about 1 m high; leaves plant are used as purgative, laxative and digestive while
are usually 5 to 11 cm long, and more or less blotched with its latex is used against conjunctivitis (Agra et al., 2008).
green and white, glaucous broad at the base, half-clasping Besides, its infusion finds application against hypertension
the stem prominently sinuate-lobed, and spiny (Chopra et in Brazil (Bieski et al., 2012). The present review deals
al., 1956). The flowers become 4 to 5 cm in diameter, and with the phytochemical and pharmacological aspects of A.
are terminal, yellow, and scentless. The capsule is spiny, mexicana covering the literature up to 2012.
obovate or elliptic-oblong, and about 3 cm in length. The
seeds are spherical, shining, black and pitted. Material and Methods
A. mexicana is considered as an important
medicinal plant in India; the yellow juice, which exudes The chemical constituents isolated and identified
when the plant is injured, has long been used in India as from Argemone mexicana, pharmacological activities
traditional medicine for dropsy, jaundice, ophthalmia, exhibited by the isolated compounds as well as by the crude
scabies and cutaneous affections (Chopra et al., 1956; plant extracts were searched across the Medline (National
Ambasta, 1986; Sharma et al., 2012). Different parts of this Library of Medicine) and ScienceDirect databases. The
plant are used in chronic skin diseases, and also as emetic, data were updated in January 2013, using the search-terms
expectorant, demulcent and diuretic; the seeds and seed oil Argemone mexicana, chemical constituents, biological
are employed as a remedy for dysentery, ulcers, asthma and activities, pharmacological activities or properties of
other intestinal affections (Chopra et al., 1956; Bose et al., Argemone mexicana as keywords. In addition, the reference
1963; Ambasta, 1986; Prajapati et al., 2003; Savithramma lists of all papers identified were reviewed.

#
In memory of Santosh Kr. Brahmachari
559
Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

Staphylococcus aureus, Listeria monocytogenes,

Clostridium botulinum, Clostridium perfringens,
Escherichia coli, Pseudomonas aeruginosa and
Salmonella typhimurium. The organic crude extracts
showed potent antibacterial activity against the
bacterial strains at a concentration of 10 μL exhibiting
zones of inhibition in the range of 10.1 to 21.4 mm with
MIC values ranging from 62.5-500 μg/mL (Rahman et
al., 2009). This study indicates the presence of some
antibacterial chemical constituents in the plant, which
might find useful applications. It was also reported that
chloroform extract of A. mexicana seeds at a dose of 500
mg/mL show significant antimicrobial activity against
both gram positive and gram negative microorganisms
such as E. coli, P. aeroginosa, Enterococcus sp.,
Salmonella typhi, S. aureus with MIC values in the
range of 2-5 mg/mL (Singh et al., 2009b); however, the
methanol extract at the same dose showed a moderate
activity only against P. aeruginosa, S. typhi and S.
aureus. In addition, the 50% aqueous methanolic extract
of A. mexicana fruits was tested for its antibacterial
potential against some gram positive and gram negative
bacteria such as Klebsiella oxytoca, Vibrio damsella,
Enterobactor aerogens and E. coli, and it was revealed
that the crude extract is more effective against gram
negative bacteria as tested (Jain et al., 2012). Pandey &
Figure 1. Argemone mexicana L., Papaveraceae. Karanwal (2011) also demonstrated that the ethanolic
extract of the seeds possesses significant antibacterial
Chemical constituents activity against the pathogenic bacteria, P. aeruginosa,
E. coli and S. aureus with MIC value 230 μg/L. Similar
Chemical constituents isolated so far from kind of studies on antibacterial efficacy of different
this plant are presented in Table 1. Most of the isolated organic and aqueous plant extracts were also investigated
compounds belong to the class of alkaloids; besides, (Bhattacharjee et al., 2006; Abubacker & Ramanathan,
terpenoids, flavonoids, phenolics, long-chain aliphatic 2012; Bhardwaj et al., 2012). Both ethanolic and
compounds, and few aromatic compounds are found to aqueous extracts of A. mexicana were found to have
be other constituents of this plant. antibacterial potential against Streptococcus mutans
and Porphyromonas gingivalis responsible for oral
Biological activities exhibited by the plant and plant cavity infection; the alcoholic extract showed greater
constituents potency against S. mutans with MIC value of 125 μg/
mL, while the aqueous extract against P. gingivalis with
Various biological activities exhibited by MIC value of 78 μg/mL (Rosas-Pinon et al., 2012).
both the crude plant extracts and isolated chemical Different leaf extracts (acetone, methanol,
constituents are described categorically under the ethanol and aqueous) of A. mexicana were found to
following sub-sections: exhibit antipseudomonal activity against multidrug
resistant P. aeruginosa isolated from clinical samples
Antibacterial activity (Sahu et al., 2012). Twenty-seven strains have
been used for this antimicrobial study and applying
Crude plant extracts of A. mexicana L. as agar well diffusion method, the MIC and minimum
well as some of its chemical constituents were found bactericidal concentration (MBC) values noted for
to exhibit antimicrobial potential (Saranya et al., acetone, methanol and ethanol are 10, 8, 8 mg/mL and
2012). Rahman and his group (2009) studied in vitro 32, 28, 24 mg/mL, respectively, thereby demanding
antibacterial activity of the crude stems extracts that leaf of A . mexicana as complementary medicine in
(n-hexane, chloroform, ethyl acetate and ethanol) of treating diseases caused by multidrug resistant strains
the plant against a number of food-borne gram positive of P. aeruginosa. Following the same procedure,
and gram negative bacteria such as Bacillus subtilis, another research group (Alagesaboopathi & Kalaiselvi,

560 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013

 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

Table 1. Chemical constituents of Argemone mexicana.

Compound Plant parts Reference
Alkaloids
isocorydine (1) apigeal parts Israilov et al., 1986
berberine (2) apigeal parts, seeds Israilov et al., 1986; Ito et al., 1990; Chang et al., 2003b; Haisova & Slavik,
1975; Fletcher et al., 1993
dehydrocheilanthifoline (3) whole plants Chang et al., 2003b
dehydrocorydalmine (4) whole plants Singh et al., 2010c; Singh et al., 2009a
jatrorrhizine (5) whole plants Singh et al., 2010c
columbamine (6) whole plants Singh et al., 2010c
coptisine (7) whole plants Chang et al., 2003b; Ito et al., 1990
(+)-reticuline (8) apigeal parts, aerial parts Israilov et al., 1986; Hussain et al., 1983; Chang et al., 2003a; Rahman,
1994
protopine (9) apigeal parts, seeds Israilov et al., 1986; Ito et al., 1990; Chang et al., 2003b; Haisova & Slavik,
1975; Tripathi et al., 1999
allocryptopine (10) apigeal parts Israilov et al., 1986; Chang et al., 2003b; Haisova & Slavik, 1975.
cryptopine (11) whole plants Haisova & Slavik, 1975; Shamma, 1972
muramine (12) whole plants Nakkady et al., 1988
argemexicaine A (13) whole plants Chang et al., 2003b
argemexicaine B (14) whole plants Chang et al., 2003b
protomexicine (15) aerial parts Singh et al., 2012
13-oxoprotopine (16) aerial parts Singh et al., 2012
(-)-cheilanthifoline (17) apigeal parts Israilov et al., 1986; Haisova & Slavik, 1975; Shamma, 1972
(-)-scoulerine (18) apigeal parts Israilov et al., 1986; Haisova & Slavik, 1975; Shamma,1972
(+)-cheilanthifoline (19) whole plants Tripathi et al., 1999
(-)-stylopine (20) Whole plants Haisova & Slavik, 1975; Shamma, 1972
nor-sanguinarine (21) whole plants Haisova & Slavik, 1975; Tripathi et al., 1999; Rahman, 1994
chelerythrine (22) whole plants Chang et al., 2003b
sanguinarine (23) seeds Chang et al., 2003b; Haisova & Slavik, 1975; Fletcher et al., 1993.
oxyhydrastinine (24) whole plants Hussain et al., 1983; Rahman, 1994; Nakkady et al., 1988
thalifoline (25) whole plants Nakkady et al., 1988
argemexirine (26) whole plants Singh et al., 2010b
(+)-argenaxine (27) aerial parts Chang et al., 2003a
(+)-higenamine (28) aerial parts Chang et al., 2003a
(±)-tetrahydrocoptisine (29) whole plants Singh et al., 2010b
(-)-tetrahydroberberine (30) whole plants Chang et al., 2003b
dihydrocoptisine (31) whole plant Singh et al., 2010b
oxyberberine (32) whole plants Singh et al., 2010c; Singh et al., 2009a
N-demethyloxysanguinarine aerial parts Chang et al., 2003a
(33)
pancorine (34) aerial parts Chang et al., 2003a
O-methylzanthoxyline (35) whole plants Chang et al., 2003b
nor-chelerythrine (36) whole plants Haisova & Slavik, 1975
arnottianamide (37) whole plants Chang et al., 2003b
(±)-6-acetonyl whole plants Chang et al., 2003b; Nakkady et al., 1988; Migahid, 1978
dihydrochelerythrine (38)
dihydrosanguiranine (39) seeds Fletcher et al., 1993; Chang et al., 2003a
dihydrochelerythrine (40) tissues Chang et al., 2003a
angoline (41) whole plants Chang et al., 2003b; Chang et al., 2003a

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Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

8-acetonyl whole plants Nakkady et al., 1988

dihydrosanguiranine (42)
8-methoxy aerial parts Singh et al., 2012
dihydrosanguiranine (43)
dihydropalmatine hydroxide seeds Ito et al., 1990
(44)
(-)-argemonine (45) plant resins Rahman, 1994; Shamma, 1972

CH3 R1 OCH 3
H
N
N
R2 OH
H
H3 CO R3 HO CH 3
OH N
H 3 CO
R4 H3 CO
OCH 3
1 2 R 1 =R 2= -OCH 2O-; R 3 =R 4=OCH 3 8
3 R 1 =OCH 3; R2 =OH; R3 =R4 = -OCH2 O-
R1 4 R 1 =R 2=R 3=OCH 3; R4 =OH
5 R 1 =OH; R2 =R 3 =R 4 =OCH 3 R4
CH3 6 R 1 =R 3=R 4=OCH 3; R2 =OH R5
N
R2 7 R 1 =R 2=R 3=R 4= -OCH 2O- R3
O R2
R3 R4
N
R7 R5 CH 3 R1
N
R6 O
17 R 1=R 2= -OCH 2O-; R 3=H(β); R 4=OH; R 5=OCH 3
9 R 1 =R 2=R 4=R 5= -OCH 2O-; R 3=R 6=R 7=H O 18 R 1=R 4=OH; R 2=R 5=OCH 3; R 3 =H(β)
10 R1 =R2 = -OCH2 O-; R4 =R5 =OCH 3 ; R 3=R6 =R7 =H 19 R 1=R 2= -OCH 2O-; R 3=H(α); R 4=OH; R 5 =OCH 3
11 R1 =R2 =OCH 3 ; R 4=R5 = -OCH2 O-; R 3=R6 =R7 =H 16 20 R 1=R 2=R 4=R5 = -OCH2 O-; R 3=H(α)
12 R1 =R2 =R4 =R 5 =OCH 3; R3 =R6 =R7 =H
13 R1 =R2 = -OCH2 O-; R3 =R4 =R5 =H; R 6 =R 7=OCH 3
14 R1 =R4 =R7 =H; R 2 =R 3=OCH 3; R5 =R 6 =-OCH2 O-
15 R1 =R2 = -OCH2 O-; R3 =R4 =R5 =H; R 6 =OH; R7 =OCH 3

O O
O O
CH3 R1
N
N
N
R2 CH3
R1
O
O
O R2
21 22 R1=R2=OCH3 24 R1=R2= -OCH2O-
23 R1=R2= -OCH2O- 25 R1=OCH3; R2=OH

R1
O O
NH
R2 O N O N R1
H
R1 R2

R3 R5
R2 R3
R4

26 R 1=R 2=OH; R 3=R 4=R5 =H 29 R1 =R2 = -OCH 2 O- 31 R1 =H; R 2 =R 3 = -OCH 2O-

27 R 1=R 2= -OCH2 O-; R 3=CH 2 OH; R 4=R5 =OCH3 30 R1 =R2 =OCH 3 32 R1 = =O; R2 =R3 =OCH 3
28 R 1=R 2=R5 =OH; R 3=R4 =H

562 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013

 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

O R5 O O
R4 O O
O
NH N NCH3
R3 H 3CO OH
O CHO
O O R2 R1 OCH 3

33 34 R 1=OCH 3; R2 =R 3 = -OCH 2O-; R 4 =R 5=H 37

35 R 1=R 2=R 3=H; R4 =R5 =OCH 3
36 R 1=R 4=R 5=H; R2 =R3 =OCH 3

O H3 CO

N OH H 3CO OCH 3
O H3 CO N
OCH 3 CH3
N H 3CO OCH 3
R3 CH 3
R2 R1
OCH 3
38 R1 =CH 2COCH3 ; R 2=R 3=OCH 3
39 R1 =H; R 2 =R 3= -OCH 2O- 44 45
40 R1 =H; R 2 =R 3=OCH 3
41 R1 =R2 =R 3 =OCH 3
42 R1 =CH 2COCH3 ; R 2=R 3= -OCH 2O-
43 R1 =OCH 3 ; R 2=R3 = -OCH2 O-

Terpenoids
trans-phytol (46) aerial parts Chang et al., 2003a
β-amyrin (47) leaves Sukumar et al., 1984

HO
H

H
HO
46 H 47

Steroids
stigma-4-en-3,6-dione (48) aerial parts Chang et al., 2003a
β-sitosterol (49) roots Pathak et al., 1985

H
H

H H
H H
O
HO
O
48 49

Carbohydrates
lactose (50) - Sarraf et al., 1994
arabinose (51) - Sarraf et al., 1994
OH
OH HOH2C O
O OH OH
HO HO
OH
HO O
OH O
HO
OH
50 51

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Argemone mexicana: chemical and pharmacological aspects#
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Long-chain alcohols
triacotan-11-ol (52) aerial parts Sangwan & Malik, 1998
triacotan-6, 11-diol (53) aerial parts Sangwan & Malik, 1998; Dinda & Banerjee, 1987
(mexicanol)
hentriacontane-3,20-diol (54) flowers Brahmachari et al., 2010
11-oxo octacosanoic acid (55) seeds Rahman & Ilyas, 1962; Gunstone et al., 1977
11-oxo triacontanoic acid (56) seeds Fletcher et al., 1993; Gunstone et al., 1977
9-oxo octacosanoic acid (57) seeds Gunstone et al., 1977
(+)-6-hydroxy-6-methyl- oil Rukmini, 1975
9-oxo-octacosanoic acid
(argemonic acid) (58)
myristic acid (tetradecanoic oil Badami & Gunstone, 1962
acid) (59)
palmitic acid (60) oil Badami & Gunstone, 1962
stearic acid (61) oil Badami & Gunstone, 1962
arachidic acid (62) oil Badami & Gunstone, 1962
oleic acid (63) oil Badami & Gunstone, 1962
linoleic acid (64) oil Badami & Gunstone, 1962
mexicanic acid (65) aerial parts Dinda & Banerjee, 1987
CH3(CH2)nCH3 CH3(CH2)nCO2H
52 n=28 (11-ol) 55 n=26 (11-one) 61 n=16
53 n=30 (6,11-diol) 56 n=28 (11-one) 62 n=18
54 n=29 (3,20-diol) 57 n=26 (9-one) 63 n=16 (9-ene)
58 n=26 (6-CH3; 6-OH; 9-one) 64 n=16 (9,12-diene)
59 n=12 65 n=15 [4-ene(Z); 10-OH)
60 n=14

Amino acids
cysteine (66) leaves Sukumar et al., 1984
phenylalanine (67) leaves Sukumar et al., 1984
CO2H
HSCH2(CH(NH2)CO2H
NH2

66 67

Flavonoids
luteolin (68) seeds Harborne & Williams, 1983
eriodictyol (69) seeds Harborne & Williams, 1983
isorhamnetin-3-O-β-D- leaves, flowers Chang et al., 2003a; Sukumar et al., 1984; Rahman & Ilyas, 1962;
glucopyanoside (70) Krishnamurthi et al., 1965; Anthal et al., 2012
isorhamnetin (71) flowers Pathak et al., 1985; Rahman & Ilyas, 1962
isorhamnetin-7-O-β-D- flowers Rahman & Ilyas, 1962
diglucopyanoside (72)
isorhamnetin-3,7- O-β-D- flowers Krishnamurthi et al., 1965
diglucopyanoside (73)
quercetin (74) whole plants Singh et al., 2011
quercetrin (75) aerial parts Singh et al., 2012
rutin (76) whole plants, aerial parts Singh et al., 2011; Singh et al., 2012
mexitin (77) aerial parts Singh et al., 2012

564 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013

 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

R3 OH HO O
OH OH

R2O O HO O
OH O
H3CO OCH3
R1 OCH3
OH O OH O

68 R1=R2=H; R3=OH 69 77
70 R1=OGlc; R2=R3=H
71 R1=OCH3; R2=H; R3=OH
72 R1=OH; R2=di-Glc; R3=H
73 R1=OGlc; R2=Glc; R3=H
74 R1=R3=OH; R2=H
75 R1=ORha; R2=H; R3=OH
76 R1=ORut; R2=R3=H

Phenolics and aromatic acids

5,7-dihydroxy chromone seeds Bhardwaj et al., 1982
-7-neohesperidoside (78)
tannic acid (79) - Singh et al., 2010a
caffeic acid (80) - Singh et al., 2010a
ferulic acid (81) - Singh et al., 2010a
benzoic acid (82) - Dwivedi et al., 2008
cinnamic Acid (83) - Dwivedi et al., 2008
vanillic acid (84) Flowers Pathak et al., 1985
RO O OH
HO OH
OH
HO OH O
OH O OH
O
O O
78 R=neohesperidosyl OH
HO O
O
O
R1 CO2H OH HO O
HO O
O O O O
R2
OH
HO O O O
80 R1=R2=OH O O
81 R1=OCH3; R2=OH HO OH
83 R1=R2=H OH O O

O OH
R1 CO2H HO OH
O HO OH
R2 OH
HO
OH
82 R1=R2=H
84 R1=OCH3; R2=OH 79

Miscellaneous
α-tocopherol (85) aerial parts Chang et al., 2003a
adenosine (86) aerial parts Chang et al., 2003a
adenine (87) aerial parts Chang et al., 2003a
benzphetamine seeds Dalvi, 1985
N-demethylase
Sn-glycerol-1-eicosa-9,12- seeds Saleh et al., 1987
dienoate-2-palmitoleate-3-
linoleate (88)

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Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

CH3
N
HO NH2
H CH3 H CH3 HOH2C O N
N
H3C N
CH3 HO OH
CH3

85 86

NH2
CH2OCOC19H35
N N CHOCOC15H29
N N CH2OCOC17H31
H

87 88

Glc: β-D-glucopyranosyl; Rha: α-L-rhamnopyranosyl; Rut: rutinosyl; neohesperidosyl: 2-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]

2012) evaluated the antibacterial activity of the remains inactive.

aqueous, acetone, ethanol and chloroform extracts of The alkaloids, dehydrocorydalmine (4) and
the leaves, stems and roots of the plant against four oxyberberine (32), isolated from A. mexicana, were
strains of bacterial species, namely, E. coli, Klebsiella found to exhibit antifungal activities against some fungal
pneumoniae, Bacillus cereus and S. aureus, and found strains such as Helminthosporium sp., Curvularia sp.,
that stems extract possesses greater inhibitory activity Alternaria cajani, Bipolaris sp. and Fusarium udum
compared to the roots and leaves extracts. They (Singh et al., 2009a). Dehydrocorydalmine (4) was
reported that ethanol stem extract showed greatest found to inhibit spore germination of all the fungal
antibacterial activity against K. pneumoniae (22.86 species studied. The spores of Helminthosporium sp.
mm) followed by acetone extract (17.35 mm) whereas and Curvularia sp. did not germinate at all at 5000
the highest inhibition zone observed for ethanol ppm, while Curvularia sp. was found to be highly
extract of root against B. cereus was 20.05 mm and sensitive at 4000 ppm. Alternaria cajani, Bipolaris
the maximum activity of ethanol leaf extract against S. sp. and Fusarium udum were slightly resistant to
aureus was 19.12 mm. Doss et al. (2012) evaluated the this compound as they showed 11.74%, 10.15% and
leaf extracts (aqueous and alcoholic) of A. mexicana 5.74% germination, respectively, even at 5000 ppm.
to show significant antibacterial activity against a The other alkaloid, oxyberberine (32) inhibited 100%
number of bacterial strains such as Streptococcus spore germination of Bipolaris sp. and Curvularia sp.
agalactiae, Escherichia coli, Staphylococcus aureus at 5000 ppm. The germination of all the tested fungi
and Klebsiella pneumonia exhibiting zone of inhibition was greatly inhibited at 1000 to 4000 ppm. A. cajani,
ranging from 9.0 to 15.0 mm and MIC values between Helminthosporium sp. and F. udum were slightly
0.225 to 2.00 mg/mL (Doss et al., 2012). Osho & resistant at 5000 ppm (Singh et al., 2009a). A similar
Afetunji (2010) investigated in vitro antimicrobial study was also carried out by the same group (Singh et
study with essential oil of the plant against some al., 2010c) with a mixture of quaternary alkaloids and
common bacterial and fungal pathogenic microbes and some phenolic acids (tannic acid 79, caffeic acid 80 and
found promising results (Osho & Afetunji, 2010). The ferulic acid 81) of the plant. The experimental results
alkaloid, N-demethyloxysanguinarine (33), isolated also supported significant antifungal potentials of the
from chloroform extract of A. mexicana has been found test compounds.
to show antibacterial activity against K. pneumonia, S.
aureus, E. coli and P. aeroginosa with MIC value ranges Anti-HIV activity
from 1.5625 to 3.1250 mg/mL (Bhattacharjee et al.,
2010). Rahman et al. (2011) reported that acetone, ethyl The benzo[c]phenanthridine alkaloid,
acetate and petroleum ether extracts of leaf and stem of (±)-6-acetonyl dihydrochelerythrine (38) isolated from
A. mexicana exhibit efficiency to inhibit water borne the methanolic extract of air-dried whole plants of A.
pathogens such as E. coli, Shigella sp., Staphylococcus mexicana was found to exhibit potent anti-HIV activity
sp. and Salmonella sp. Petroleum ether extract of both in H9 lymphocyte assay with EC50 value of 1.77 μg/
leaf and stem shows maximum activity whereas ethyl mL (Therapeutic Index: 14.6) (Chang et al., 2003b).
acetate shows moderate activity but acetone extract

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 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

Anti-inflammatory activity plant extract is able to induce a direct and dual specific
effect upon the vascular smooth muscle, mediated, at least
The ethanolic extract of leaves of A. mexicana in part, by adrenergic receptors.
is reported to have significant anti-inflammatory and
analgesic activity at a dose of 200 mg/kg in mice (Sharma Anti-fertility activity
et al., 2010). It is also reported that leaf extract of A.
mexicana is able to show significant anti-inflammatory Three isoquinoline alkaloids, dihydropalmatine
activity in rats; the investigators (Sukumar et al., 1984) hydroxide (44), berberine (2) and protopine (9), isolated
are in opinion that the chemical constituents of the leaf from the seeds of Argemone mexicana were evaluated to
extract such as isorhamnetin-3-O-β-D-glucopyanoside have inhibitory activity against spermatogenesis in dogs
(70), β-amyrin (47), cysteine (66) and phenylalanine (67) at the stage XII of late spermatids on administration at a
might be responsible for such activity. dose of 30 mg/kg for 70 days; the numbers of spermatids
were found to decrease by 46.5, 58.0 and 97.7% with
Wound healing activity compounds 44, 2 and 9, respectively (Gupta et al., 1990).
In addition, the total numbers of mature Leydig cells
Ghosh and his group (2005) studied in vivo were also decreased by compounds 2 and 9. The relative
wound healing activity of the extract and the latex antispermatogenic activity was reported to be: 9 > 2 > 44.
of A. mexicana on excision wound healing model ―
the results demonstrated significant wound healing Cytotoxic activity
activity of the test extracts that is comparable with
the established drug, nitrofurazone; the tensile Methanolic extract of A. mexicana leaves was
strength of the extract treated group was found to be found to exhibit cytotoxic activity against healthy mouse
higher than the latex treated group of animals on 12th fibroblasts (NIH3T3) and three human cancer-cell lines
post wounding day (Ghosh et al., 2005). Significant (AGS, HT-29 and MDA-MB-435S) using the MTT [3-(4,5-
wound healing activity of petroleum ether and butanol dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide]
fractions of ethanol extract of A. mexicana, containing assay as reported by Uddin and his group (2011). The
some sterols, alkaloids, proteins and carbohydrates, result showed that the extract is much active against MDA-
was also reported in albino rat model by Patil and his MB-435S cancer cell line (IC50 1.82 mg/mL). Chang and
group (2001). Dash & Murthy (2011) investigated his group (2003a) isolated a number of alkaloids from A.
wound healing activity using excision, incision and mexicana and evaluated cytotoxic activity of some of the
dead space wound models in Wistar albino rats with isolated alkaloids viz. N-demethyloxysanguinarine (33),
different extracts of A. mexicana leaves. The results pancorine (34), (+)-argenaxine (27), (+)-higenamine
revealed that the treatment with methanol extract of (28), (+)-reticuline (8), angoline (41) and chelerythrine
leaves of A. mexicana accelerated wound healing agent (22) to human nasopharyngeal carcinoma (HONE-1) and
in rats. human gastric cancer (NUGC) cell lines. Chelerythrine
(22) was found to be the most active among the series
Anti-stress and antiallergic activity against NUGC cell lines, whereas (+)-argenaxine (27)
showed only a moderate activity. On the other hand,
Both the polar extracts (i.e. aqueous and angoline (41) inhibited both HONE-1 and NUGC cancer
methanolic) of A. mexicana stems were evaluated to cell lines (Chang et al., 2003a).
exert antiallergic as well as antistress efficacy in asthma
developed by milk-induced leucocytosis and milk- Nematicidal activity
induced eosinophilia at a dose of 50 mg/kg i.p. in albino
mice model; both of the test extracts showed significant It was reported that the seed oil of A. mexicana
(p<0.05) decrease in leucocytes and eosinophils in vivo is found to kill Meloidogyne incognita larvae in 17 min
(Bhalke & Gosavi, 2009). (Das & Sukul, 1998). The investigators found reduction
of nematode infection in terms of root galling, root protein
Vasoconstrictor and vasorelaxant effects content and nematode population in soil and roots after
application of aqueous mixture (0.2%) to soil and leaves
Paez-Sanchez and his group (2006) evaluated of Hibiscus esculentus inoculated with M. incognita.
the vascular effects of methanolic extract of the aerial Nath et al. (1982) investigated nematicidal properties of
parts A. mexicana in rat aortic rings; the test extract was plant extracts of different parts of A. mexicana against
found to produce relaxation from contraction induced by M. juvanica in experimental test tubes of microplots.
noprepinephrine in a concentration-dependent manner. They reported that plant extracts are capable of lowering
The overall experimental results demonstrated that the nematode population in the field while larvae were found

Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013 567

Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

to be immobile in 24 h. Another research group (Shaukat Fungitoxic activity

et al., 2002) reported that juvenile mortality of M. juvanica
is caused by different extracts of A. mexicana leaf material, out A. mexicana seed extract is found to be fungitoxic
of which polar solvent extract found to be more effective. against a number of fungal strains (Shah et al., 1992).
Again, seed soaking in aqueous extract of A. mexicana is The latex of the plant was found to exhibit toxicity
found to reduce penetration of the nematodes juvenile in against Trichophytan mentagrophytes (Asthana et al.,
chick pea, thereby supporting nematicidal efficacy of the 1989). The leaf extract of A. mexicana is found to exhibit
plant (Mojumder & Mishara, 1991). significant fungitoxic activity against few fruit pathogens
like Alternaria alternata, Dreschlera halodes, and
Antifeedant activity Helminthosporium speciferum (Srivastava & Srivastava,
1998), and also against Curvularia tuberculata (Upadhyay
It is reported that petroleum ether and aqueous & Rai, 1990), responsible for die-back diseases.
leaf extracts of A. mexicana were found to exhibit
significant antifeedant activity against second stage larvae Antihelmintic activity
of Henosephilachna vigintiocto puncata Fabricius (Rao et
al., 1990). The aqueous plant extracts of A. mexicana
find useful as significant antihelmintic against Indian
Lousicidal activity earthworm Pheritima posthuma (Jaliwala et al., 2011).
Majeed et al. (2011) also investigated antihelmintic
Kumar and his group (2002) investigated activity of alcohol and aqueous extracts of leaves against
lousicidal efficacy of aqueous leaf extract of A. mexicana P. posthuma and Ascardia galli in a dose dependent
by conducting mortality and repellency tests on tropicalis manner (6.25, 12.5, 25, 50, 100 mg/mL) and found that
peters and found lousicidal activity with 73% mortality. both the extracts show significant antihelmintic activity
at a concentration of 100 mg/mL.
Mollucicidal activity
Larvicidal activity
Two alkaloids, protopine (9) and sanguinarine
(23), isolated from the plant are found to exhibit Acetone fraction of the petroleum ether extract
mollucicidal activity by decreasing significantly in the of seeds from A. mexicana exhibited larvicidal and
levels of protein, free amino acid, DNA and RNA in the growth inhibiting activity against the 2nd instar larvae
nervous tissue of Lymnaea acuminata and also to cause of Aedes aegypti at concentrations from 25 to 200 ppm
a significant reduction in phospholipids levels and a having IC50 values of 13.58 ppm and 17.43 ppm at
simultaneous increase in the rate of lipid peroxidation field condition and laboratory condition, respectively
in the nervous tissue of treated snails (Singh & Singh, (Sakthivadivel & Thilagavathy, 2003). Willcox et al.
1999). (2007) also reported significant larvicidal activity
of acetone fraction of petroleum ether extract of A.
Effect on ileum organ mexicana seeds against 2nd instar larvae of A. aegypti.
The leaf extract (in petroleum ether) of the plant also
Capasso and his group (1997) studied the exhibits high larvicidal potential with LC50 value
effect of the methanolic extract, its partially purified of 48.89 ppm against 3rd -4th instar larvae of Culex
fraction, and the isolated pure compounds such as quinquefasciatus (Sakthivadivel et al., 2012). A
protopine (9) and allocryptopine (10) from A. mexicana synergistic action of this plant was also reported in
on the morphine withdrawal effect in guinea pig their findings; larvicidal potential of leaf extract of A.
isolated ileum; all the tested materials were observed to mexicana increases (LC50 value of 28.60 ppm) when
reduce the effect significantly and in a concentration- mixed (1:1) with that of Clausena dentate.
dependent manner, thereby suggesting the possible
application of isoquinoline alkaloids as potential agents Antioxidant activity
in the treatment of drug abuse. Further investigation
in this direction also indicated that that CHCl3/MeOH Perumal et al. (2010) reported that ethanol
and MeOH extracts reduced the contractions of isolated extract of A. mexicana roots possesses antioxidant
guinea-pig ileum in a dose-dependent manner (Piacente activity; at a dose of 100 μg/mL concentration, the
et al., 1998); the effects were attributed to the active extract showed high scavenging activity against
compounds identified as protopine (9), allocryptopine DPPH (85.17%), ABTS (75.27%) and H2O2 (84.25%)
(10) and berberine (2). radicals. Different extracts of A. mexicana leaves were
also reported to exhibit superoxide anion scavenging

568 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013

 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

activity by Nitro blue tetrazolium assay with maximum while decrease in total bilirubin (TBIL) and direct bilirubin
percentage of free radical scavenging at a dosage of 200 (DBIL) level tested at different doses of 125, 250 and 500
μg/mL; acetone extract being the most active showing mg/kg b.w.
IC50 value double to that of L-ascorbic acid (Bhardwaj
et al., 2011). Miscellaneous activities

Anticancer activity The Department of Traditional Medicine in

Mali has recognized A. mexicana as a standardized
The ethanol extract of A. mexicana was reported phytomedicine for home-based management of malaria
to exhibit inhibitory activity against human cancer cell (Willcox, 2011; Schrader et al., 2012). Aqueous
lines such as HeLa-B75 (48%), HL-60 (20.15%) and extract of the aerial parts of the plant was found to
PN-15 (58.11%) (Gacche et al., 2011). Gali et al. (2011) exhibit anti-parasite activity against the chloroquine-
also reported anticancer activity of methanolic extract of resistant K1 strain of Plasmodium falciparum with an
A. mexicana leaves against HeLa and MCF-7 cancer cell IC50 value 5.89 μg/mL; in a randomized, controlled
lines with IC50 values ranging from 1.35 to 1.2 μg/μL clinical trial, 89% of patients recovered clinically
based on MTT assay results. The investigators also proved (95% with artemisinin based combination therapy),
that the nature of this cytotoxic activity is apoptotic rather although parasite clearance was only achieved in 9%
than necrosis and this activity may be due to the presence of patients (Schrader et al., 2012). No deterioration
of flavonoid constituents in leaf. of severe malaria in patients >5 years and 1.9%
deterioration in children ≤5 years were observed
Antidiabetic activity in the clinical trials (Willcox et al., 2011). As far as
phytochemical constituents are concerned, A. mexicana
Aqueous extract of aerial parts of A. mexicana contains the alkaloids berberine (2), protopine (9) and
at a dose of 200 and 400 mg/kg body weight was allocryptopine (10); although these compounds showed
reported to have hypoglycemic efficacy in alloxan- in vitro antimalarial activity (IC50 of protopine against
induced diabetic rats; significant reduction in blood the W2-strain 0.91 μM) (Avello Simoes Pires, 2009),
glucose levels, plasma urea, creatinine, triacylglyceride, berberine is purely absorbed, and the aqueous decoction
cholesterol values and recovery in body weight of the plant was not active against Plasmodium berghei
compared to diabetic control rats and the standard drug in the mouse model (Willcox et al., 2011; Schrader et
treated rats are found when treated with the aqueous al., 2012).
extract at a dose of 400 mg/kg body weight (Nayak Recently, Amartha & Chaudhari (2011)
et al., 2011). Rout et al. (2011) also found that the reported on neuropharmacological applications of A.
hydro-alcoholic extract of aerial parts of A. mexicana mexicana; the ethyl acetate and methanol extract of
reduces fasting blood glucose levels in Streptozotocin- the whole plant of A. mexicana exhibited analgesic,
induced hyperglycemic Wistar albino rats at a dose of locomotor and muscle relaxant activity in Wistar
200 and 400 mg/kg body weight; experimental results albino mice at an oral dosage of 100, 200 and 400 mg/
also showed that the extract dosage of 400 mg/kg kg b.w. Both extracts showed significant activities
body weight has effective hypoglycemic activity in but methanol extract at a dosage of 200 mg/kg body
comparison with the standard drug metformin at a dose weight was found to be more potent for central nervous
of 300 mg/kg body wt. (Rout et al., 2011). system activities such as analgesic, anxiolytic and
sedative effects (Amartha & Chaudhari, 2011). In
Antihepatotoxic activity addition, acetone leaf extract of the plant showed
significant anti-termitic activity against the Formosan
Das et al. (2009) showed promising antihepatotoxic subterranean termite pest, Coptotermes formosanus
activity of aqueous extract of A. mexicana stem in carbon Shiraki, in a dose-dependent manner; after 48 h of
tetrachloride-induced hepatotoxic male Albino Wistar rats; exposure, the plant extract exhibited LD50 and LD90
oral administration of 150 and 250 mg/kg body weight of values of 253 and 1511 ppm, respectively (Elango et
the extract decreased serum asparate transaminase, alanine al., 2012). Table 2 offers a closer look at the bioactive
aminotransferase and alkaline phosphatase levels. Another chemical constituents of A. mexicana.
research group (Sourabie et al., 2012) also investigated
the anti-icterus activity of crude leaf powder of the plant Toxicity and safety evaluation of A. mexicana
against CCl4-induced hepatotoxicity in Wistar rats; the
investigators observed significant increase in the levels Few works on the toxicity and safety evaluation
of ASAT/GOT (aspartate aminotransferase), ALAT/GPT of A. mexicana are reported. Ibrahim & Ibrahim (2009)
(alanine aminotransferase) and ALP (alkaline phosphate) showed that the plant extract exhibits acute toxicity

Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013 569

Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

Table 2. A quick look at the bioactive compounds from A. mexicana.

Compound Biological activity Reference
berberine (2) Anti-fertility activity Gupta et al., 1990
Effect on ileum contraction in guinea pig Piacente et al., 1998
Antimalarial activity Avello Simoes Pires, 2009
dehydrocorydalmine (4) Antifungal activity Singh et al., 2009a
(+)-reticuline (8) Cytotoxic activity Chang et al., 2003a
protopine (9) Anti-fertility activity Gupta et al., 1990
Effect on ileum in guinea pig Capasso et al., 1997; Piacente et al., 1998
Mollucicidal activity Singh & Singh, 1999
Antimalarial activity Avello Simoes Pires, 2009
allocryptopine (10) Effect on ileum in guinea pig Capasso et al., 1997; Piacente et al., 1998
Antimalarial activity Avello Simoes Pires, 2009
chelerythrine (22) Cytotoxic activity Chang et al., 2003a
sanguinarine (23) Mollucicidal activity Singh & Singh, 1999
(+)-argenaxine (27) Cytotoxic activity Chang et al., 2003a
(+)-higenamine (28) Cytotoxic activity Chang et al., 2003a
oxyberberine (32) Antifungal activity Singh et al., 2009a
N-demethyloxysanguinarine (33) Cytotoxic activity Chang et al., 2003a
pancorine (34) Cytotoxic activity Chang et al., 2003a
(±)-6-acetonyl dihydrochelerythrine (38) Anti-HIV activity Chang et al., 2003b
angoline (41) Cytotoxic activity Chang et al., 2003a
dihydropalmatine hydroxide (44) Anti-fertility activity Gupta et al., 1990
β-amyrin (47) Anti-inflammatory & analgesic activity Sukumar et al., 1984
cysteine (66) Anti-inflammatory & analgesic activity Sukumar et al., 1984
phenylalanine (67) Anti-inflammatory & analgesic activity Sukumar et al., 1984
isorhamnetin-3-O-β-D-glucopyanoside (70) Anti-inflammatory & analgesic activity Sukumar et al., 1984

in mice with LD50 value of 400 mg/kg body weight arterioles (Husain et al., 1999). Sanguinarine (23) is
when administered intraperitoneally in the subjects reported to have hepatotoxic potential in rats (Dalvi,
having weight of 18-25 g and averagely aged between 1985), because a single i.p. dose (10 mg/kg) of the
4-6 weeks. Seed oil of the plant is also reported to compound not only increased the activity of SGPT and
show toxic effects in experimental animals, and such SGOT substantially but also caused a significant loss
toxicity is supposed primarily due to sanguinarine (23). of microsomal cytochrome P-450 and benzphetamine
The alkaloid 23 is reported to be 2.5 times more toxic N-demethylase activity. Furthermore, the treated rats
than its reduced product, dihydrosanguinarine (39), and exhibited considerable loss of body and liver weight,
both of them are interconvertable by simple oxidation peritoneal edema and slightly enlarged livers with
and reduction process (Verma et al., 2001). It is also fibrinous material. Microscopic examination of the liver
reported that alkaloid 23 is the causative component tissue showed progressive cellular degeneration and
of glaucoma and epidemic dropsy, a disease resulting necrosis, thereby, establishing that the test compound
in neuroparalysis and death of several people (Verma 23 is a potential hepatotoxic alkaloid (Dalvi, 1985).
et al., 2001). The mechanism of toxicity of Argemone A detailed study on the metabolism of sanguinarine
oil is still not cleared but four different postulations characterizing the oxidative metabolites produced by
have been described so far to explain the toxicity of human CYP1A1 and CYP1A2 and rat liver microsomes
sanguinarine — inhibition of Na+/K+ATPase, cell was recently reported by Deroussenta et al. (2010).
membrane damage by reactive oxygen species and Since consumption of mustard oil adulterated
lipid peroxidation, inhibition of DNA polymerase with Argemone oil leads to a clinical condition,
activity, and accumulation of pyruvate due to increased commonly referred to as “Epidemic dropsy” (Sood
glycogenolysis (Verma et al., 2001). It is believed et al., 1985; Deroussenta et al., 2010), the in vivo
that sanguinarine present in Argemone oil is toxic and clastogenic and DNA damaging potential of Argemone
interferes with the oxidation of pyruvic acid which will oil was investigated by Ansari and his group (2004) in
accumulate causing dilation of capillaries and small mice. In their investigation, Swiss albino mice were

570 Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 23(3): May/Jun. 2013

 Argemone mexicana: chemical and pharmacological aspects#
Goutam Brahmachari et al.

intraperitoneally administered 0.5, 1.0, 2.0 and 4.0 jaundice, leprosy, microbial infections, and malaria.
mL/kg body weight of the oil to analyze chromosome Beyond alkaloids, the plant species is the source of a
aberrations and micronucleus test, while 0.25, 0.5, 1.0 diverse kind of other chemical constituents that include
and 2.0 mL/kg body weight were given for alkaline comet terpenoids, steroids, carbohydrates, long-chain aliphatic
assay. The frequencies of chromosomal aberrations and alcohols and carboxylic acids, amino acids, flavonoids and
micronucleated erythrocytes formation in mouse bone other phenolics. Besides pharmaceutical efficacies, certain
marrow cells increased in a dose-dependent manner parts of the plant also show toxic effects as well; toxicity
following the oil treatment. However, significant and safety evaluation of using this plant and its chemical
induction in chromosomal aberrations (83%) and constituents are also dealt in this review. Hence, an up-
micronucleated erythrocytes formation (261%) were to-date information on the chemical and pharmacological
observed at a minimum dose of 1.0 mL/kg. The results knowledge on this plant may be helpful to guide researchers
of comet assay revealed DNA damage in blood, anticipating to undertake further investigations on this
bone marrow and liver cells following Argemone oil plant. Pharmacological and clinical studies of different
treatment. These results clearly suggest that single chemical constituents of A. mexicana are found to be very
exposure of test oil even at low doses can produce promising, which calls for more-systematic research of this
genotoxic effects in mice (Ansari et al., 2004). The medicinal plant and its active principles; more in-depth and
same research group (Ansari et al., 2005) also studied extensive studies in all relevant aspects are still warranted.
the in vivo DNA damaging potential of sanguinarine 23 We do anticipate that the present overview would boost the
in blood and bone marrow cells of mice using alkaline on-going development in this direction.
comet assay. Swiss albino male mice were given single
intraperitoneal administration of 1.35, 2.70, 5.40, Acknowledgements
10.80 and 21.60 mg sanguinarine alkaloid/kg body
weight, while controls were treated with saline in the The authors are thankful to the Chemistry
same manner. The results revealed a dose dependent Department, Visva-Bharati University for providing
increase in DNA damage in blood and bone marrow infrastructural facilities. Financial support from the
cells following 24 h treatment of sanguinarine alkaloid UGC, New Delhi is also deeply acknowledged.
23. All the three parameters of comet assay including
olive tail moment (OTM), tail length and tail DNA Authors’ contributions
showed significant (p<0.05) increases in blood and
bone marrow cells at respective doses of 10.80 and The concept, design, and arrangement of the
5.40 mg alkaloid/kg body weight. These results indicate present review article were contributed by GB; he also
that single exposure of the test compound causes DNA analyzed all the data, supervised the process of drafting
damage in blood and bone marrow cells of mice, which and contributed in finalizing the article through critical
could be responsible for the genotoxicity of Argemone reading of the draft manuscript. DG and RR both
oil (Ansari et al., 2005). Upreti et al. (1989) showed contributed equally in collecting exhaustive searching
that membrane destruction may be a possible mode on the databases, summarizing the data and preparing a
of action for damaging liver, lungs, heart and kidneys draft. All the authors have read the final manuscript and
of rats due to Argemone oil toxicity in rats. This oil, approved the submission
one of the adulterants encountered in edible oil, is also
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of Argemone mexicana. Oriental J Chem 15: 185- Department of Chemistry, Visva-Bharati University
186. Santiniketan-731235, West Bengal, India
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