Professional Documents
Culture Documents
Journal of Ethnopharmacology
journal homepage: www.elsevier.com/locate/jethpharm
Review
a r t i c l e
i n f o
Article history:
Received 1 July 2010
Received in revised form 18 October 2010
Accepted 26 November 2010
Available online 3 December 2010
Keywords:
Apiaceae
Asafoetida
Ferula assa-foetida
Oleo-gum-resin
Sesquiterpene coumarins
a b s t r a c t
The old traditional phytomedicine asafoetida, an oleo-gum-resin obtained from the roots of different
Ferula assa-foetida, is used in different countries for various purposes. Asafoetida is not only used as a
culinary spice but also traditionally used to treat various diseases, including asthma, gastrointestinal disorders, intestinal parasites, etc. This oleo-gum-resin has been known to possess antifungal, anti-diabetic,
anti-inammatory, anti-mutagenic and antiviral activities. A wide range of chemical compounds including sugars, sesquiterpene coumarins and polysuldes have been isolated from this plant. Recent studies
have shown new promising antiviral sesquiterpene coumarins from this old phytomedicine. The present
review summarizes the information concerning the traditional uses, phytochemistry and biological activities of asafoetida.
2010 Elsevier Ireland Ltd. All rights reserved.
Contents
1.
2.
3.
4.
5.
Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Traditional uses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Phytochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3.1.
Coumarins and sesquiterpene coumarins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3.2.
Sulfur-containing compounds. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
3.3.
Other compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Pharmacology . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
4.1.
Bioactive compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Discussion and conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Acknowledgments . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
1. Introduction
Asafoetida is an oleo-gum-resin obtained from the exudates of
the roots of the Iranian endemic medicinal plant, Ferula assa-foetida.
This species (Ferula assa-foetida) is often considered to be the main
source of asafoetida, although other Ferula species, such as Ferula
foetida, Ferula rubricaulis, Ferula rigidula, Ferula alliacea and Ferula
narthex, are also sources of asafoetida (Rajanikanth et al., 1984;
1
2
2
2
3
4
4
8
8
8
9
Table 1
Various names of asafoetida in some different languages.
Language
Name
Afghan
Arabic
Chinese
Dutch
English
Finnish
French
German
Hindi
Hungarian
Italian
Nepali
Pakistan
Polish
Russian
Spanish
Swedish
Turkish
Kama, Anguza
Shajarat-ul-Heltit, Angudn
A-wei
Duivelsdrek
Asafetida, Stinking assa, Devils dung
Pirunpaska, Pirunpihka
Ase-ftide
Stinkender assand, Teufelsdreck
Hing, Hingu
Ordoggyoker
Asa fetida
Hing, Hingu
Kama, Anguza
Zapaliczka Cuchnaca, Asafetida
Asafetida
Asaftida
Dyvelstrck
Seytan tersi, Seytan boku, Seytanotu
particularly in India. In addition, Nepali people regularly consume it in their daily diets, and it is believed that asafoetida has
aphrodisiac, sedative and diuretic properties (Eigner and Scholz,
1990; Bandyopadhyay et al., 2006). It is traditionally used for
the treatment of different diseases, such as asthma, epilepsy,
stomachache, atulence, intestinal parasites, weak digestion and
inuenza (Zargari, 1996; Takeoka, 2001; Evans, 2002; Lee et al.,
2009). Recent pharmacological and biological studies have also
shown several activities, such as antioxidant (Dehpour et al., 2009),
antiviral (Lee et al., 2009), antifungal (Singh, 2007; Sitara et al.,
2008; Angelini et al., 2009), cancer chemopreventive (Aruna and
Sivaramakrishnan, 1992; Saleem et al., 2001), anti-diabetic (AbuZaiton, 2010), antispasmodic (Fatehi et al., 2004), hypotensive
(Fatehi et al., 2004), and molluscicidal (Kumar and Singh, 2006)
from this oleo-gum-resin.
Along with these biological surveys, there have been a number of phytochemical investigations of asafoetida (Mahran, 1973;
Pangarova and Zapesochnaya, 1975; Rajanikanth et al., 1984;
Buddrus et al., 1985; Banerji et al., 1988; Kajimoto et al., 1989;
Nassar et al., 1995; Nassar and Mohamed, 1998; Abd El-Razek
et al., 2001; Takeoka, 2001; Duan et al., 2002; Khajeh et al.,
2005; Appendino et al., 2006; Bandyopadhyay et al., 2006; Abd
El-Razek, 2007; Ghosh et al., 2009; Lee et al., 2009; Mirzaei
and Hasanloo, 2009). Asafoetida consists of three main fractions,
including resin (4064%), gum (25%) and essential oil (1017%)
(Takeoka, 2001). The resin fraction contains ferulic acid and its
esters, coumarins, sesquiterpene coumarins and other terpenoids.
The gum includes glucose, galactose, l-arabinose, rhamnose, glucuronic acid, polysaccharides and glycoproteins, and the volatile
fraction contains sulfur-containing compounds, monoterpenes and
other volatile terpenoids. Bioassay-guided fractionation studies of
asafoetida have led to the identication of some interesting bioactive compounds; for example, Lee et al. characterized antiviral
sesquiterpene coumarins from asafoetida that are more potent than
amantadine against inuenza A (Lee et al., 2009).
The present review deals with the traditional uses, phytochemistry, and pharmacological studies of asafoetida. In addition, this
review includes bioactive compounds isolated from asafoetida.
2. Traditional uses
We classied the traditional uses according to similar uses of
asafoetida.
Gastrointestinal disorders: In Ayurveda, asafoetida is introduced
as a valuable remedy for atulence (Kapoor, 2001). Asafoetida
roasted in ghee (a claried butter without any solid milk particles or water) is usually used in gastrointestinal disorders because
unprocessed asafoetida causes irritation and inammation (Gogte,
2000). It is also used for the treatment of stomachache in the eastern region of Shimoga of India (Rajakumar and Shivanna, 2009). In
India, asafoetida is traditionally used as an antibacterial agent, an
antispasmodic, a diuretic and a laxative (Srinivasan, 2005). Water
extract of the dried gum is also taken orally as an antihelminthic
(Eigner and Scholz, 1990; Ross, 2005; Bandyopadhyay et al., 2006).
In Iranian folk medicine, asafoetida is used as an antispasmodic,
antihelminthic, and carminative agent. In addition, it is used as a
mild laxative medicine for the elderly (Zargari, 1996). American
people orally use it as an antihelminthic and it is claimed to be a
powerful antispasmodic (Ross, 2005). In China, asafoetida is used
for infestation with intestinal parasites (Emami et al., 2010). In Fiji,
water extract of the dried gum is also taken orally for the treatment
of upset stomach (Ross, 2005).
Nervous disorders: In Ayurveda, asafoetida is introduced as a
valuable remedy for hysteria and nervous disorders (Kapoor, 2001).
In Afghanistan, hot water extract of the dried gum is also taken
orally for hysteria. Nepali people use it as a sedative and a diuretic
spice (Eigner and Scholz, 1990; Ross, 2005; Bandyopadhyay et al.,
2006). In Iranian folk medicine, asafoetida is used as an anticonvulsant (Zargari, 1996) as well as it is chewed as an antiepileptic in
Morocco (Ross, 2005). American people orally use it as a stimulant
to the brain and nerves (Ross, 2005).
Respiratory problems: Apparently, one of the most important
traditional uses of asafoetida is the treatment of asthma. In India,
asafoetida is traditionally used as a useful symptomatic treatment
for angina pectoris and asthma (Srinivasan, 2005). In Ayurveda,
asafoetida is introduced as a valuable remedy for whooping cough,
pneumonia and bronchitis in children. It is also a pulmonary
stimulant (Kapoor, 2001). In Saudi Arabia, dried asafoetida is
medicinally used for whooping cough, asthma, and bronchitis
(Ross, 2005). In Iranian folk medicine, asafoetida is also used
as a medicine for the treatment of asthma (Zargari, 1996). In
Afghanistan and Fiji, the dried gum is taken for whooping cough
(Ross, 2005). In ancient Rome, it was used as a culinary spice and as
a replacement for Silphion cyrenaicum (Appendino et al., 2006). The
aforementioned plant has been used for tuberculosis and incessant
cough.
Impotence: In Ayurveda and traditional medicines of different
countries such as America and Brazil, it is considered to be an
aphrodisiac (Kapoor, 2001; Ross, 2005).
In spite of various applications of asafoetida in different cultures,
its consumption is forbidden in traditional Korean Buddhism (Kim
et al., 2006). In homeopathy, asafoetida is used for low acid levels in
the stomach, stomach pressure, atulence and loose stools (Emami
et al., 2010).
It seems that the most frequent uses of asafoetida are in
upper respiratory diseases, including the treatment of asthma,
bronchitis and whooping cough (as an expectorant), and gastrointestinal disorders as an antihelminthic, anti-atulence and
antispasmodic.
3. Phytochemistry
3.1. Coumarins and sesquiterpene coumarins
Tsukervanik et al. was the rst group to begin to investigate
plants of the genus Ferula in 1935 (Abd El-Razek et al., 2003). Ferula
is a genus rich in coumarins, particularly sesquiterpene coumarins
(Abd El-Razek et al., 2003). To date, many sesquiterpene coumarins
have been identied from this genus. A large number of different
sesquiterpene coumarins have been reported from asafoetida. The
variation in the structures of reported sesquiterpene coumarins
may be due to their different sources. In Fig. 1, the chemical structures of sesquiterpene coumarins that have been reported to date
are depicted.
Sesquiterpene coumarins of Ferula assa-foetida include umbelliprenin (1), 5-hydroxyumbelliprenin (2), 8-hydroxyumbelliprenin
(3), tadshiferin (4), asacoumarin A (5), 8-acetoxy-5-Shydroxyumbelliprenin (6), asacoumarin B (7) (the structure
of this compound was revised later and it was revealed that its
structure is the same as that of galbanic acid), assafoetidin (8),
franesiferol A (9), franesiferol B (10), franesiferol C (11), galbanic
acid (12), conferol (13), gummosin (14), assafoetidinol A (15) and
assafoetidinol B (16) (Nassar et al., 1995; Abd El-Razek et al., 2001,
2003; Appendino et al., 2006, 1993; Lee et al., 2009).
Some other sesquiterpene coumarins reported from Ferula
assa-foetida are ferocaulicin (17), epi-samarcandin (18), episamarcandin acetate (19) and kamolonol (20) (Nassar et al., 1995;
Nassar and Mohamed, 1998; Abd El-Razek et al., 2003).
Other studies on Ferula assa-foetida resin have also led to the
isolation of different sesquiterpene coumarins including foetidine
(21), saradaferin (22), 10-R-acetoxy-11-hydroxyumbelliprenin
(23), 10-R-karatavicinol (24), methyl galbanate (25), lehmferin
(26), feselol (27), ligupersin A (28), epi-conferdione (29), microlobin
(30), polyanthinin (31) and umbelliferone (7-hydroxycoumarin)
(Buddrus et al., 1985; Abd El-Razek et al., 2001; Bandyopadhyay
et al., 2006).
R2
COOH
R3
R1
1 R1= R2 =R3= H
HO
7
O
R1
4 R1=R2= H, R3= OH
R2
5 R1=R2= OH, R3 = H
HO
10
9 R1= OH, R2 = H
14 R1 = H, R2 = OH
O
O
O
13
HOOC
HO
12
11
R1
H
OH
R3
R4
R1
R2
R3
AcO
O
O
O
R2
17
O
O
O
O
H
20
21
HO
OH
HO
22
O
O
HO
23
OH
26
HO
25
24
27
28
HO
O
O
29
O
HO
O
H3COOC
HO
OAc
30
AcO
OH
31
Fig. 1. (Continued )
have also been reported from the roots of Ferula foetida (Duan et
al., 2002).
3.3. Other compounds
The compounds of Ferula assa-foetida are not limited to
sesquiterpene coumarins and sulfur-containing compounds; it also
contains some other compounds belonging to different classes
of natural products, such as diterpenes like 7-oxocallitrisic acid
(64), picealactone C (65) and 15-hydroxy-6-en-dehydroabietic
acid (66) (Lee et al., 2009), phenolics like vanillin and 3,4dimethoxycinnamyl-3-(3,4-diacetoxyphenyl) acrylate (67) (Abd
El-Razek, 2007), acetylenes such as falcarinolone (68) (Christensen
and Brandt, 2006), sesquiterpenes like taraxacin (69) (Appendino
et al., 2006), fetidone A (70) and B (71) (Appendino et al., 2006) and
other miscellaneous compounds, such as oleic acid, -sitosterol,
galactose, arabinose, glucuronic acid, rhamnose, luteolin 7--dglucopyranoside (72) and ferulic acid (Fig. 3) (Pangarova and
Zapesochnaya, 1975; Zargari, 1996; Lee et al., 2009).
4. Pharmacology
In vitro studies: Recently, antiviral activity of asafoetida was
assessed against some human rhinovirus serotypes (Rollinger et al.,
2008). In this study, Rollinger et al. proved that cytopathic effects
Table 2
Pharmacological/biological activities reported from asafoetida in detail.
Activity
Concentrations/dosages
Tested living
system/organ/cell
Result(s)
Reference(s)
Anti-diabetic
Alloxan-induced
diabetic rats (in vivo)
Abu-Zaiton (2010)
Anti-fertility
400 mg/kg
Antifungal
Oleo-gum-resin
Antispasmodic
Aqueous extract of
oleo-gum-resin
SpragueDawley rats
(in vivo)
Aspergillus parasiticus
Antispasmodic
Aqueous extract of
oleo-gum-resin
3 mg/ml
Guinea-pig ileum
(in vitro)
Antitumor
Water extract of
oleo-gum-resin (oral)
Oleo-gum-resin
Colloidal solution of
oleo-gum-resin (oral)
Acetone extract of
oleo-gum-resin (topical)
Cancer chemopreventive
(another study)
Oleo-gum-resin (oral)
Female
SpragueDawley rats
(in vivo)
Oleo-gum-resin (oral)
Oleo-gum-resin (oral)
Hypotensive
Aqueous extract of
oleo-gum-resin
Dried latex powder, ethanol,
chloroform, acetone and ether
extracts of dried latex powder
Resin
Anaesthetized rat
(in vivo)
Snail (in vivo)
Antiulcerogenic
Cancer chemopreventive
Molluscicidal
Mutagenic
a
b
0.7525 g/ml
Salmonella
typhimurium
Unnikrishnan and
Kuttan (1990)
Rollinger et al. (2008)
Agrawal et al. (2000)
Saleem et al. (2001)
Mallikarjuna et al.
(2003)
Antiviral
Guinea-pig ileum
(in vitro)
32
S
38
37
S S
S
44
45
S S
50
55
SH
59
40
41
S
47
S
52
51
42
S
S
S
57
56
63
60
43
48
S
54
53
OH
49 S S
36
58
S S
35
34
33
S S
46 S S
S
39
S
61
O
O
S
S
62
S
O
Fig. 2. Sulfur-containing compounds isolated from asafoetida.
OH
HOOC
64
O
O
COOH
65
67
OH
68
66
O
O
HO
69
O
70
71
OH
OH
HO
HO
O
OH
OH O
OH
72
Fig. 3. Miscellaneous compounds from different classes of natural products reported from asafoetida.
Toxicological studies: To our knowledge, there is no comprehensive toxicological study of asafoetida. However, a case of
methemoglobinemia has been reported after administration of
asafoetida in a 5-week-old black male infant. The infant was admitted to the hospital 6 h after the onset of tachypnea, grunting, and
cyanosis. Treatment was with intravenous methylene blue and the
infant recovered (Kelly et al., 1984). The intake of larger dosages can
lead to swelling of the lips, digestive complaints such as atulence
and diarrhea, discomfort and headache. Swelling of the genital
organs has been observed following external administration on
the abdomen. It is not recommended to be used during pregnancy
(Emami et al., 2010).
Table 3
Biological activities reported from the bioactive coumarins of asafoetida.
Compound number
Compound name
Biological activities
Reference(s)
Antiviral (inuenza H1 N1 )
29
13
8-Acetoxy-5-Shydroxyumbelliprenin
10-R-acetoxy-11hydroxyumbelliprenin
epi-Conferdione
Conferol
9
10
11
Farnesiferol A
Farnesiferol B
Farnesiferol C
Antiviral (inuenza H1 N1 )
Antiviral (inuenza H1 N1 ), Cytotoxic (HepG2, Hep3B and
MCF-7), synergistic effect with anticancer agents
(vincristine)
Antiviral (inuenza H1 N1 )
Antiviral (inuenza H1 N1 , HRV-2)
Antiviral (inuenza H1 N1 , HRV-2), antiangiogenic,
antitumor
Molluscicidal, anticoagulant, antioxidant (as sodium
ferulate), cancer chemopreventive, anti-atherosclerotic,
angiogenesis inducer, neuroprotective, antigenotoxic,
vasodilator, hypoglycemic
6
23
Ferulic acid
12
Galbanic acid
24
28
25
10-R-karatavicinol
Ligupersin A
Methyl galbanate
Umbelliferone
Umbelliprenin
Acknowledgments
We would like to thank Dr. Seyyed Ahmad Emami and Dr. Javad
Asili for their scientic consulting and kind help.
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