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CHEMICAL CONSTITUENTS AND PHARMACOLOGICAL EFFECT OF INULA

GRAVEOLENS (SYN: DITTRICHIA GRAVEOLENS)-A REVIEW

Article · April 2018

DOI: 10.5281/zenodo.1214990

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 IAJPS 2018, 05 (04), 2183-2190 Ali Esmail Al-Snafi ISSN 2349-7750

CODEN [USA]: IAJPBB ISSN: 2349-7750

INDO AMERICAN JOURNAL OF

PHARMACEUTICAL SCIENCES
http://doi.org/10.5281/zenodo.1214990

Available online at: http://www.iajps.com Review Article

CHEMICAL CONSTITUENTS AND PHARMACOLOGICAL

EFFECT OF INULA GRAVEOLENS
(SYN: DITTRICHIA GRAVEOLENS)- A REVIEW
Ali Esmail Al-Snafi
Department of Pharmacology, College of Medicine, University of Thi qar, Iraq.
Cell: +9647801397994. E mail: aboahmad61@yahoo.com
Abstract:
The phytochemical study showed that Inula graveolens contained polyphenols, tannins, flavonoids, oil, steroidal
triterpenoides, sesquiterpene and anthraquinones. The pharmacological researches revealed that Inula graveolens
exerted antimicrobial, insecticidal, anti- platelet aggregation, antiproliferative, anti-diarrheal, antipyretic,
analgesic, antiinflammatory and anticholenergic effects. The current review discussed the chemical constituents and
pharmacological effects of Inula graveolens.
Keywords: chemical constituents, pharmacology, Inula graveolens
Corresponding author:
Ali Esmail Al-Snafi QR code
Department of Pharmacology,
College of Medicine,
University of Thi qar, Iraq
Cell: +9647801397994.
E mail: aboahmad61@yahoo.com

Please cite this article in press Ali Esmail Al-Snafi., Chemical Constituents and Pharmacological Effect of
Inula Graveolens [SYN: Dittrichia Graveolens]- A Review, Indo Am. J. P. Sci, 2018; 05(04).

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INTRODUCTION: lance-linear, 1–3[–7] cm × 1–3[–10] mm, margins

Plants contained biologically active chemicals, some entire or denticulate, apices acute, faces pilosulous to
of these were extremely useful for the treatment of hirtellous and minutely stipitate-
human diseases, but many plant constituents glandular. Phyllaries 1–8 mm. Ray florets [6–]10–
produced side effects and may life-threatening 12[–16]; corolla laminae 2–5[–7] mm. Disc florets 9–
illnesses[1-14]. The phytochemical study showed that 14+; corollas 3–4 mm. Cypselae 1.5–2 mm[21-22].
Inula graveolens contained polyphenols, tannins,
flavonoids, oil, steroidal triterpenoides, sesquiterpene Traditional uses:
and anthraquinones. The pharmacological researches Inula graveolens was widely used in aromatherapy
revealed that Inula graveolens exerted antimicrobial, for the treatment of asthma. It was used as
insecticidal, anti- platelet aggregation, bronchospasmolytic and mucolytic[23]. Inula
antiproliferative, anti-diarrheal, antipyretic, analgesic, graveolens was widely used in Iraq for the treatment
antiinflammatory and anticholenergic effects. This of rheumatic fever, infant convulsions, toothache, to
review will discuss the chemical constituents and reduce blood sugar, to dissolve internal blood clots,
pharmacological effects of Inula graveolens. and to aid digestion[18]. In Iranian traditional
Plant profile: medicine it was used as a anti-inflammation,
Synonyms: antirheumatism, antitumor, antipathogene and
antiinfection specially in the treatment of
Conyza minor Bubani, Cupularia graveolens [L.] leishmaniosis[20]. It was also used for treatment of
Godr. & Gren., Dittrichia graveolens [L.] Greuter, urinary tract infections, hemorrhoids, cold and
Erigeron graveolens L., Inula brahuica Boiss., Inula wound infections[24].
quadridentata Lag and Jacobaea graveolens[L.]
Merino[15]. Oil was inhaled in low concentrations for desired
Taxonomic classification: mucolytic effect, as decongestant in sinusitis and
respiratory inflammations, and for loosening mucus
in unproductive coughs and asthmatic conditions.
Kingdom: Plantae; Subkingdom: Tracheobionta;
Topically, it was used as counteracts and was
Superdivision: Spermatophyta; Division:
blended with Eucalyptus Dives, Spike Lavender, and
Magnoliophyta; Class: Magnoliopsida; Subclass:
Rosemary Verbenone, to releive acne caused by
Asteridae; Order: Asterales; Family: Asteraceae ⁄
ovreactive sebaceous glands. Inula dissolved
Compositae; Genus: Dittrichia/ Inula; Species: Inula hardened sebum from clogged glands[25]. Essential
graveolens and Dittrichia graveolens[16].
oil was also used to support lymphatic circulation
Common names: and the immune system, and to reduce acneic skin
inflammation[26].
Arabic: Inula, Shuwaser, Suawaid, Rasan, Teion; Part used medicinally:
English: Camphor inula, Cape khakiweed, Stinking- The whole plant and its oil [18, 23-26].
fleabane, Stinkweed, Stinkwort; German: Drüsiger
Alant, Klebriger Alant; Iran: Atre paizii Swedish:
Kamferinula[17-20]. Chemical constituents:
The preliminary phytochemical study showed that
Inula graveolens contained polyphenols, tannins,
Distribution: flavonoids, oil, steroidal triterpenoides, sesquiterpene
and anthraquinones[27-31].
It was distributed in Africa [Egypt, The chemical composition of the essential oils of
Algeria, Libya, Morocco, Tunisia]; Asia [Iraq, Iran, Inula graveolens varies depending on the plant
Palestine, Jordan, Lebanon, Syria, Turkey, Pakistan]; origin. The main component found in the essential
Europe [Albania, Bosnia, oils of Inula graveolens from Corsica was borneol
Bulgaria, Croatia, Greece, Italy, Macedonia, Montene [7.6%]. However, essential oil of Inula graveolens
gro, Serbia, France, Portugal, Spain, from Corsica contained santolinatriene 0.5, α-pinene
Austria, Belgium, Czech Republic, Germany, 0.3, camphene 6.1, β-pinene 0.8, dehydrocineole
Netherlands, Switzerland, United Kingdom, 1.7, p-cymene 0.1, limonene 0.7, p-cymenene 0.1,
Slovenia]; Australasia [Australia, New Zealand] and camphor 0.1, trans-chrysenthemyl alcohol 0.1, p-
Northern America [USA][17-19]. mentha-1,5-dien-8-ol [α-phellandren-8-ol] 0.2,
Description: Borneol 7.6, and trace amounts of α-terpinene,
Plant viscid, rank smelling, 20–130 cm; stems ± camphene hydrate, yomogi alcohol, myrcene, α-
pilose and stipitate-glandular. Leaf blades linear to phellandrene, santolina alcohol, β-phellandrene, [E ]-

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β -ocimene, γ -terpinene, artemisia alcohol, trans-ρ-menth-2-en-1,8-diol 2.19, decanal 0.18, β-

terpinolene, linalool, fenchol and lavandulol[29]. methyl-benzenepropanal 0.5, trans-carveol 0.1, nerol
Analysis of oil of the aerial parts of Inula graveolens 0.4, carvol 0.09, vetiverol 0.08, piperitone 0.25,
from Algerian origin, showed that the main nonanoic acid 0.14, 4-hydroxy-3-methyl
constituents were: bornyl acetate [69.78%], borneol acetophenone 0.11, carvacrol 0.06, bornyl acetate
[4.25%], caryphyllene oxide [5.7 %], 1[7]5 - 14.86, 1-5 [methyl-2-furanyl]-1-buten-3-one 0.13, ρ-
menthadien-8-ol [2.10 %], chamigrene [2.9 %] and mentha-1[7],2-dien-8-ol 0.39, 2,4-decadienal 0.32, 1-
the b selinene 0. 95%. However thirty compounds methylnaphtalene 0.04, hydragine 0.2, β-
were isolated included [%]: camphre: 0.25, 1[7]5 - damascenone 0.4, caryophyllene 1.98, 6,10-dimethyl-
mentha –diene-2-ol: 0.09, bornyle acetate: 69.78, P- 5,9-undecadien-2-one 0.34, 3,4-diethylphenol 7.5, β-
cymene -8- ol: 0.98, 1[7]2 mentha diene 8 ol: 2.10, lonone 0.28, β-selinene 0.26, α-selinene 0.16, α-
isoborneol: 0.10 borneol: 4.25, menth-1-ene-9-ol amorphene 0.4, 6,6-dimethyl-2-[2-[trimethylsilyl]
acetate: 0.28, 4 -terpineol: 0.30, b-caryophyllene: ethyl cyclohex-2-enone 1.7, geranyl propionate 1.8,
0.50, benzoate de geranyle: 0.18, allo-4- geranyl butyrate 2.0, caryophyllene oxide 4.0,
aromadendrene: 0.20, isogermacrène D: 0.15, cyercene 1.1, β-cubebene 7.1, α-cadinol 0.38, 5-epi-
isobornyl-2-methylbutyrate: 0.15, neryl acetate: paradisiol 0.89, geranyl hexanoate 0.85, hexafarnesyl
0.34, ocimenone: 1.00, caryphyllene oxide: 5.7, acetone 2.5 and isovaleric acid 3-phenylpropyl ester
occidentallo acetate: 0.78, nerolidol acetate: 0.38, a- 2.1[24].
chamigrene: 2.90, epicadinol: 1.68, a -eudesmol:
1.17, 4-methyl valerate de neryl: 0.39, nerolidol: 1,8-cineole [22.4%], borneol [20.4%] and a-cadinol
0.63, trans verbenol: 0.18, cis eudesm-6-ene- 12 al: [11.8%] were determined as the main compounds of
0.10, farnesyl acetate: 0.24, isobornyl isobutyrate: Inula graveolens from Turkey. However, thirty six
0.33, b -selinene: 0.95, and germacrene B: 0.67[32]. compounds were identified included [%]: 2-hexenal
0.4,a-pinene 2.3, benzaldehyde -, sabinene 1.2, b-
The main constituent of the oil of Inula graveolens pinene 3.6, myrcene -, santolinatriene 0.2, a-
from Iran were 1,8 cineole [54.89%], p-cymene phellandrene 0.4, a-thujene 0.3, p-cymene 3.5,
[16.2%], β- pinene [6.94%] and borneol [5.44%]. limonene 0.5, camphene 4.6, 1,8-cineole 22.4, g-
However twenty compounds were isolated included terpinene 0.6, benzene, 1- methyl - 2 0.2, terpinolene
[%]: α-pinene 3.21, β-pinene 6.94, myrcene 0.2, α- -, linalool 0.3, trans-pinocarveole -, 𝛼-terpineol 1.5,
phellandrene 0.89, p-cymene 16.2, 1,8-cineol 54.89, camphor 0.4, 2-cyclohexan-1-ol -, thymol methyl
γ-terpinene 0.56, linalool 0.51, undecane 0.28, oxide 0.4, thymol 1.8, a-cubebene -, b-elemene 0.6, a-
fenchol 0.37, trans-pinocarveol 1.69, pinocarvone copaene 0.4, b-bourbonene -, b-cubebene 0.1, b-
0.53, borneol 5.44, terpin-4-ol 1.37, α-terpineol 1.31, caryophyllene 1.9, a-humulene -, d-cadinene 0.6, g-
myrtenol 0.35, dodecane 0.25, bornyl acetate 0.24, muurolene 1.3, bornylacetate 5.3, germacrene D -, b-
tridecane 0.19, β-caryophyllene 1.58, α-humulene selinene 0.9, bicyclogermacrene -, b-caryophyllene
1.99 and α-muurolene 0.42[33]. On the other hand, 4.8, a-muurolene 0.4, spathulenol 1.6, Borneol 20.4,
the chemical analysis of the essential oil of the caryophyllene oxide -, ledol 1.3, a-cadinol 11.8, b-
flowering aerial parts of Dittrichia graveolens eudesmol 0.1, hexadecanoic acid -, pentadecanal 0.2,
[whole aerial part at flowering stage] from Shoshtar nonadecane -, tricosane -, pentacosane 0.2 and
suburb [Khozestan Province, Iran] revealed the hexacosane 0.4[34].
presence of sixty compounds . The major components
were borneol [38.2%], bornyl acetate [14.86%] Thirty compounds were characterized in the essential
followed by 3,4-diethyl phenol [7.5%], β-cubebene oil of the fresh aerial parts of Inula graveolens from
[7.1%] and caryophyllene oxide [4.0%]. However, Algeria. The main compounds were isobornylacetate
the compounds isolated from the sample were [50.8 %], borneol [18.3 %] and τ- cadinol
included [%]: α-pinene 0.09, camphene 0.12, 2- [6.2.%][35].
heptenal 0.02, benzaldehyde 0.04, 2β-pinene 0.05, 6-
methyl-5-hepten-2-one 0.03, 2,4-heptadienal [cis,cis] The analysis of essential oil constituents of the aerial
0.06, 4-ethyl-1,2-dimethylbenzene 0.04, limonene part without flowers [stems and leaves], flowers and
0.09, 1,8-cineole 0.16, 2-methylene cyclopentanol roots of Inula graveolens from Monastir [Tunisia]
0.02, o-tolualdehyde 0.03, β,β-dimethylstyrene 0.08, revealed that the main compounds in the aerial part
α-terpinolene 0.26, nonanal 0.14, 6-methyl-3,5- without flowers were α-cadmol [9. 2%], borneol [21
heptadiene-2-one 0.04, β-thujone 0.03, trans-ρ- .4%], bornyl acetate [33. 4%]. While, the main
mentha-2,8-dienol 0.09, 2-ethyl hexanoic acid 0.04, components found in the flowers oil, were
trans-ρ-menthadien-1-ol 0.07, alcanfor 0.61, Camphene [5.5%], α-cadinol [11. 3%], borneol
neroloxide 0.44, borneol 38.2, ρ-cymen-8-ol 0.53, [19.3%] and bornyl acetate [39. 6%]. The major

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constituents in the oil roots were found to be carvone involved in the toxic action of Inula graveolens
[5.0%], bornyl acetate [5.3%], p-mentha-I, 2-dien-8-ol essential oils[40].
[5.3%] and β-selinene [11.5% ][36].
The antimicrobial activity of the essential oil was
The oil of Inula graveolens from Jordan, was studied against five bacterial and one fungal strain
characterized by high percentages of oxygenated using a disk-diffusion assay. The essential oil was
monoterpenes, they were the predominant fraction. active only against Gram-positive bacteria[41].
Their percentage was found to increase with time,
during the collection period [from 86.5% in August to The antimicrobial effects of Inula graveolens
93.7% in January]. Simultaneously, the percentage of petroleum ether, chloroform and ethanol extracts
sesquiterpene hydrocarbons and monoterpene were investigated [at concentration of 20, 40 and 80
hydrocarbons decreased from 2.9% to about zero and µl of 5% concentration in dimethyl sulphoxide]
from 4.4% to 1.6% respectively. Bornyl acetate against Bacillus subtilis, Micrococcus luteus,
[percent content ranged from 68.7% in August to Staphylococcus aureus, Escherishia coli, Klebsiella
82.6% in January] was the principal component in all pneumoniae, Pseudomonas aeruginosa and Candida
months of collection throughout the vegetative albicans. The extracts showed concentration
cycle[37]. dependent antimicrobial effects against Bacillus
More than 50 compounds were identified from the subtilis, Micrococcus luteus, Staphylococcus aureus
essential oil obtained from the aerial parts of Greek and Candida albicans. The most potent effect was
Dittrichia graveolens. The major constituents of the recorded for petroleum ether extract. However, all
oil were found to be epi-α-cadinol [30.2%] and extract in the higher concentrations [40 µl of 5%
bornyl acetate [25.4%][38]. The total phenolic concentration in dimethyl sulphoxide] also showed
content of the methanolic extract of Inula graveolens antimicrobial effects against Escherishia coli,
from Iraq was 1.63% gallic acid equivalent, while the Klebsiella pneumoniae and Pseudomonas
total flavonoid content was 0.52% quercetin aeruginosa [28].
equivalent of dry mass of plant extract[39].The total
phenolic content of the Inula graveolens The antibacterial effects of Dittrichia graveolens
methanolic leaves extracts from Morocco was essential oil were investigated against nine different
86.19±3.04mg GAE/g extract, and the total ATCC type strains of microbial species, including
flavonoids content was 9.72±0.94 mg QE/g Gram-positive bacteria [S. aureus, E. faecalis, B.
extract[27]. Many sesquiterpene lactones, subtilis], Gram-negative bacteria [E. coli, P.
eudesmanolide, 11,13-dihydroivalin, ivalin, aeruginosa], yeast [C. albicans, C. glabrata] and
inuviscolide, 8-epi-inuviscolide, 8-epi-xanthatin- fungi [A. niger, A. parasiticus] . The MICs and
1β,5β-epoxide were isolated from the aerial parts of MLCs of oil against all tested microorganisms were
Inula graveolens [16]. Sesquiterpene derivatives, in the range of 0.25–4 and 1–8 μl/ml, respectively. E.
3alpha-hydroxyilicic acid methyl ester, 2alpha- faecalis and C. glabrata were the most sensitive
hydroxy-4-epi-ilicic acid, 2alpha-hydroxy-2R- microorganisms with the lowest MIC and MLC
xanthalongin, 4-epi-isoinuviscolide, 8-epi-helenalin, values [0.5 and 1 μl/ml], whereas the least susceptible
and bigelovin were isolated from the active epigeal microorganisms were S. aureus and E. coli [4 and 8
parts extracts of Dittrichia graveolens[31]. μl/ml][24].

Pharmacological effects: The antibacterial activity of methanolic and acetone

extract of aerial parts of Dittrichia graveolens was
Antimicrobial effects: tested against Shigella dysenteriae [PTCC1188],
The antibacterial activity of Inula graveolens Pseudomonas aeruginosa [PTCC1430], Escherichia
essential oils was evaluated against Staphylococcus coli [PTCC1399], Staphylococcus aureus
aureus with studying the effect at the cellular level. [PTCC1431], Bacillus cereus [PTCC1015] and
A bactericidal mode of inhibition was established for Salmonella typhimurium [ATCC1596], Methanolic
the essential oils, it rapidly reduced the cell viability extract showed more potent antibacterial activity
of S. aureus MIC [5 mg/ml]. No lysis occurred after against Staphylococcus epidermidis [PTCC1114],
treatments with the MIC and eight times the MIC of Enterococcus faecalis [PTCC1393] and Klebsiella
the essential oil. Thickenings of the cell wall as well pneumoniae [PTCC1291]. Staphylococcus aureus,
as an aggregation of the cytoplasmic contents were Staphylococcus epidermis, E. faecalis and B. cereus
observed in S. aureus cells treated with the MIC of with inhibition zone 35, 30, 26, 21 mm were the most
the essential oils. The results suggest that the sensitive bacteria, with minimum inhibitory
cytoplasmic membrane and the cell wall were concentrations [MIC] ranging from 12.6 to 112

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μg/ml, respectively. E. coli and Salmonella method. The IC50 of the extracts was 86.67±1.59
typhimurium showed moderate sensitivity and other mg/l[27].
bacteria were resistant to the plant extract[20].
The antioxidant activity of methanolic and acetone
The antibacterial activity of Dittrichia graveolens extract of aerial parts of Dittrichia graveolens was
essential oil was investigated by the broth evaluated spectrophotometrically by DPPH, total
microdilution method against thirteen bacterial antioxidant capacity and reducing power activity. The
strains. The interactions of the essential oil and three methanolic extract of plant showed strong
standard antibiotics [chloramphenicol, tetracycline antioxidant activity against free radical scavenging
and streptomycin] toward five selected strains were specially in DPPH methode than aceton extract with
evaluated using the microdilution checkerboard assay IC50 of 6.2 ± 0.13μg/ml[20].
in combination with chemometric methods, principal
components analysis and hierarchical cluster analysis. The total phenolic, flavonoid and flavonol content,
The essential oil exhibited slight antibacterial activity the antioxidant activities of Dittrichia graveolens
against the tested bacterial strains in vitro, but the were evaluated. The total amount of phenols and
combinations Dittrichia graveolens essential oil- flavonoid in different plant organs of Dittrichia
chloramphenicol and Dittrichia graveolens - graveolens were different, the content of total
tetracycline exhibited synergistic or additive phenols and flavonoid in the flowers and leaves were
interactions. These combinations reduced the significantly more than the stems and roots. The
minimum effective dose of the antibiotics and, content of flavonol in the flowers, leaves and stems
consequently, minimized their adverse side effects. In were not significantly different, and the lowest
contrast, the using of Dittrichia graveolens essential content was observed in the roots. A linear and
oil and streptomycin was characterized by strong significant correlation coefficient was found between
antagonistic interactions against E. coli ATCC 25922, the antioxidant activity and the phenolic compounds
S. aureus ATCC 29213 and P. aeruginosa ATCC in the extracts of different organs of the plant[45].
27853[42]. In studying of antioxidant activity of the oil of
Dittrichia graveolens, 10 μl of essential oil reduced
Anti-Candida activity of the volatile oil of the aerial the concentration of DPPH free radical with an
parts of D. gravolence against different isolates of efficacy higher than that of 1mM Trolox [t=70 min].
Candida albicans was studied in vitro using serial Dittrichia graveolens oil reduced the DPPH to
dilutions of volatile oil in Sabouraud’s dextrose agar. 32.3%[24].
MIC of the volatile oil for 10 Candida albicans
isolates was 30.675 mg/ml[33]. Anti- platelet aggregation effect:
However, it was reported that Inula graveolens The methanolic extract of Inula graveolens showed
extracts, obtained by extraction with hot and cold potential platelet aggregation inhibitory activity in a
water and then lyophilization, were inactive against dose-dependent manner. The maximum inhibition
S. aureus and S. faecium cells [40, 43]. was observed at the dose of 400 μg/ml [P<0.01]
compared to heparin [20 μg/ml][18].
Insecticidal effect:
In studying of insecticidal activity of Inula Antiproliferative effect:
graveolens, oil caused 0, 10, 16.66 and 33.33% The extract showed strong antiproliferative [IC50
mortality of adult Mayetiola destructor at 3.83 mg/ml] and cytotoxic activity [IC50 5.83
concentration of 15, 30, 60 and 90 µg/l of air, mg/ml] against MCF-7 cell line, while it showed no
respectively[44]. activity against A549 and HL60 cells at 50
mg/ml[46].
Antioxidant effect:
The methanolic extract of Inula graveolens Anti-diarrheal effect:
possessed strong antioxidant activity [64.28%],
strong reducing power [increasing as the extract The Anti-diarrheal effects of the methanolic extract
concentration increases] and ferrous ion chelating of Inula graveolense were examined in rats. At the
[96%] abilities. Moreover, the methanolic extract doses of 200 [P < 0.05] and 400 mg/kg body weight
showed the highest free radical scavenging activities [P<0.01], the extract displayed remarkable
for superoxide anion and hydroxyl radical [93.43% antidiarrheal activity by reducing the rate of
and 91.38%, respectively] [45]. defecation and intestinal transit time of charcoal
The antioxidant activity of methanol leaves extracts meal compared to normal saline control group, the
of Inula graveolens was evaluated using the DPPH

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effect was dose dependent and similar to loperamide 6. Al-Snafi AE. Fumaria parviflora- A review. Indo
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effects: medicinal properties of Digitalis lanata and
The antipyretic activities of the methanolic extract of Digitalis purpurea - A review. Indo Am J P Sci
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[P<0.01] dose dependent anti-pyretic effect in yeast of Daphne mucronata - A review. Indo Am J P
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dose of 400 mg/kg [P < 0.01] as compared to 10. Al-Snafi AE. Chemical constituents and medical
diclofenac sodium [50 mg/kg]. The extract inhibited importance of Galium aparine - A review. Indo
paw and ear edema in a dose-related manner. A dose- Am J P Sc 2018; 5[3]: 1739-1744.
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