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Euphorbia helioscopia: Chemical Constituents and Biological Activities

Article · January 2012

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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

e- ISSN 0975 – 9328

Print ISSN 2229 – 7472
International Journal of Phytopharmacology

Journal homepage: www.onlineijp.com

IJP
EUPHORBIA HELIOSCOPIA: CHEMICAL CONSTITUENTS AND
BIOLOGICAL ACTIVITIES

Abou-El-Hamd H. Mohameda,*, Mohamed-Elamir F. Hegazyb,h, Mahmoud F. M.

Moustafac, Magdi A. El-Sayedd, Ibrahim B. Abdel-Faridd, Abeer M. Esmaila, Mohamed H.
Abdelrazike, Naglaa S. Mohameda, Gomah Nenaahf, Tarik A. Mohamedb, Abdelaaty A.
Shahatb, Joe Karchesyg , Hisashi Matsudah, and Paul W. Parei

a
Department of Chemistry, Aswan-Faculty of Science, South Valley University, Aswan, Egypt.
b
Chemistry of Medicinal Plants Department, National Research Center, Dokki, Cairo, Egypt.
c
Department of Biological Sciences, College of Science, King Khalid University, Saudi Arabia.
d
Department of Botany, Aswan-Faculty of Science, South Valley University, Aswan, Egypt.
e
Natural Products Chemistry Department, National Research Centre, Dokki, Giza,12622, Egypt.
f
Department of Zoology, Faculty of Science, Kafrelsheikh University, Kafr El Sheikh, 33516, Egypt.
g
Department of Wood Science and Engineering, Oregon state University, Corvallis, OR 97331, USA.
h
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan.
i
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.

ABSTRACT
Euphorbia, the largest genus in the spurge family “Euphorbiaceae” with more than 2000 species and is subdivided
into many subgenera and sections. Several species of the genus Euphorbia have been extensively studied for their antiviral,
antitumor, cytotoxic, antimicrobial and pesticidal activities. Based on traditional information, Euphorbia helioscopia has
been widely used in the traditional folk medicine in China and Turkey. Up to now, 30 diterpenoids have been isolated and
structurally characterized from this plant. The aim of the present work is to review all the available scientific literatures
published on E. helioscopia. The focus will be on the chemical constitutions that have been identified from this species, in
addition, all the reported biological, pharmacological and toxicological activities of different extracts and isolates from this
species have been included. The paper recommends the need for further investigations regarding the environmental and
mammalian safety of E. helioscopia for safer using in different biological and therapeutic applications.
Keywords: Euphorbia helioscopia, chemical constituents, terpenes, flavonoids, volatile oil, biological activities.

INTRODUCTION in the humid tropics and subtropics of both hemispheres

Euphorbiaceae is the largest family among the (Uzair M et al., 2009). The genus Euphorbia is the largest
Anthophyta, with 300 genera and 5000 species. The genus in the Euphorbiaceae family with over 2000 species
genuses sub cosmopolitan but with strong representation ranging from annuals to trees and is subdivided into many
subgenera and sections. All contain latex and have unique
Corresponding Author flower structures (Barla A et al., 2006; Chaudhry BA et
al., 2001; Jassbi AR et al., 2006). Euphorbia species are
Abou-El-Hamd H. Mohamed used for the treatment of various ailments such as skin
E-mail: [email protected] disease, gonorrhea, migraines, intestinal parasites and
 79
Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

warts cures. The plant lattices have been used in fish stem, end in a more or less compound umbel which is
poisons, and insecticide (Uzair M et al., 2009). Based on subtended by a circle of leaflets. The leaves are scattered
traditional information, the leaves and the lattices of this along the stem; they are somewhat oblong or wedge-
genus are used in the ayurvedic system of medicine for shaped, sometimes nearly round, from one-half to four
bronchitis and rheumatism (Barla et al., 2006). inches long, finely saw-edged, and narrowed to a short
Furthermore, it is stated to possess inflammatory, stalk. The rather inconspicuous flowers are of two kinds,
antiarthritic, antiamoebic, spasmolytic, antiviral, the staminate and pistillate on the same plant, both
hepatoprotective and antitumor activities. For hundreds of included in a cup-shaped involucre resembling a calyx or
years with traditional Chinese medicine Euphorbia have corolla. The staminate flowers are numerous, lining the
been used for the treatment of cancers, tumors and warts, inside of the cup, each consisting of one single stamen in
and is well known that this pecies contains irritant and the axil of a very little bract. The pistillate flower is
tumor-promoting constituents (Yang ZS et al., 2009). solitary in the centre of the cup and consists of a three-
Quite a number of species are used in folk medicine as lobed, three-celled ovary which soon protrudes on a long
drugs and raw materials for pharmaceutical preparations. stalk and hangs over the brim of the cup-like involucre.
In Turkish folk medicine, Euphorbia species have been The seeds are reddish-brown, strongly honeycombed. The
used for rheumatism, swelling and especially as a wart plant is in bloom from June till October (Fyles F, 1919).
remover. However, it can also trigger causes
inflammation and diarrhea (Barla, 2006). Taxonomy
Euphorbia helioscopia linn is classified into
Euphorbia helioscopia linn., known also as Lun Kingdom: Plantae, Subkingdom: Tracheobionta,
spurge (known in English as wolf’s milk, in French as Superdivision: Spermatophyta, Division: Magnoliophyta,
turnsol), is widely distributed in China, The whole plant Class: Magnoliopsida, Subclass: Rosidae, Order:
has great medicinal importance, often used to treat ascites, Malpighiales, Family: Euphorbiaceae, Subfamily:
edema, pulmonary tuberculosis, tinea and cervical Euphorbioideae, Tribe: Euphorbieae, Subtribe:
tuberculous lymphaden (Feng WS et al., 2009; Feng WS Euphorbiinae, Genus: Euphorbia, and species: Euphorbia
et al., 2010; Li, 2007). The leaves and stems are used as helioscopia Linn. (Doe J, 2010).
febrifuge and vermifuge. The oil from the seeds has
purgative properties, the roots are used as anthelmintic Distribution
and the seeds mixed with roasted pepper have been used The plant is native to the temperate regions of
in the treatment of cholera (Uzair M et al., 2009). Based Eurasia but has adapted to subtropical conditions. It
on some ethnobotanical surveys for medicinal plants used occurs as high as 3,000 m in India and Pakistan and is
traditionally in different countries, it has been recorded found to lat 69° N in Europe and Canada. It behaves as a
that, E. helioscopia is used by local people in Pakistan as winter annual in Japan, flowering from April to May. In
cathoratic, antihelminthic and purgative (Qureshi RA et India, plants flower from December to April on the plains
al., 2007). In addition, the milky juice from the leaves and and in May in hilly regions. It is often associated with
fresh stems are used to release pus (Ahmed S et al., light textured soils (Holm L et al., 1997), and in Upper
2006). In Jordan, milky juice has been used as an Egypt it was recorded in many cultivated crops
antiscorbutic as well as a diaphoretic (Al-Qura’n, 2009) (Mahmoud FM, 1996).
also known as toxic species that cause diarrhoea, general
fatigue, dysentery, dizziness, and anoxia (Al-Qura’n, Phytochemistry
2005). In China, E. helioscopia has been used as a E. helioscopia L. has been intensively
traditional folk medicine for the treatment of malaria, investigated. Different kinds of secondary metabolites,
bacillary dysentery and osteomyelitis (Lu ZQ et al., such as triterpenoids, diterpenoids, flavonoids, tannins
2008). A weed used by early dyers for bluish purple and lipids have been isolated from this species by several
(basic) and red (acid) shades, it acts as an indicator, groups during the past four decades (Durrani AA et al.,
giving colors resembling litmus, and was probably used at 1967; Zhang W et al., 2006).
one time as a food colorant (Mell CD, 1927).
Diterpenes
Botanical aspects Macrocyclic diterpenes
Morphology The metabolic pattern of Euphorbia helioscopia
E. helioscopia is a smooth annual plant with an is heavily characterized by a series of complex
erect, stout stem from eight to twelve inches high, often macrocyclic diterpenes, (e.g. jatrophon, jatrophane, and
branched from the base. The branches, as well as the main lathyrane).
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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Jatrophon type diterpenoids 95% EtOH extract of the whole plant of E. helioscopia
More than thirty jatrophon type diterpenes have collected in Sichuau, China, new jatrophane type
been isolated and structurally characterized from the diterpene was isolated and identified as euphornin N (49)
Japanese E. helioscopia L., Few studies on the methanol (Geng D et al., 2010). From the 95% EtOH extract of the
extract of the fresh leaves and roots of E. helioscopia, whole plant collected from Xuzhou, Jiangsu province,
collected in Kanagawa, Japan have been made in the four jatrophane type diterpenoids were isolated and
course of searching for physiologically active substances. identified as 7β,9α,14β-triacetoxy-3β-benzoyloxy-
Yamamura (1981) have isolated two euphoscopin- 12β,15β-epoxy-11β-hydroxy-jatropha-5E-ene(50),14β-
diterpene types which have been identified as Acetoxy-3β-benzoyloxy-7β,9α,15β trihydroxyjatropha-
euphoscopin A (1) and B (2), further investigation by 5E,11E-diene (51), 7β,9α,14β-triacetoxy-3β-benzoyloxy-
Shizuri (1983 a) and Ohba (1983) resulted in the isolation 15β,17-dihydroxy-jatropha-5E,11E-diene (52), 14α,15β-
of three new diterpenes, identified as helioscopinolide A diacetoxy-3β,7β-dibenzoyloxy-17-hydroxy-9-oxo-2βH-
(3), B (4) and C (5). Two new toxic diterpenes jatropha -5E,11E-diene (53) (Lu ZQ et al., 2008).
euphohelioscopin A (6) and B (7) together with two
euphoscopin-type skeleton euphoscopins C (8) and D (9) Lathyrane diterpenes
have also been isolated by Shizuri (1983 b). In connection From the 30% MeOH extract of the whole plant
with highly oxygenated diterpenes that have antitumor of E. helioscopia L., collected from Xixia county of
activity or promote cancer development in tumor Henan province, a new lathyrane diterpenes glycoside has
formation, three new diterpenes have been identified: been isolated and identified as 3β,7β,15β-trihydroxy-14-
euphornins A (10), B (11) and C (12) as well as, five new oxolathyra-5E,12E-dienyl-16-O-β-D-glucopyranoside
diterpenes euphohelins A-E (13-17) isolated by (Shizuri, (54) (Feng, 2010). The lathyrane diterpene
1984; Koemura, 1985). Examination of the toxic euphohelioscopin C (55) was isolated from the whole
diterpenes afforded eight new jatrophon type diterpene plants, collected at Altilia (Barile E et al., 2008; Corea G
euphornin D-K (18-25) and twelve new euphoscopin-type et al., 2009).
diterpene: euphoscopin E-L (26-33) and epieuphoscopin
A (34), B (35), D (36) and F (37) and euphohelionon (38) Triterpenes
(Yamamura S et al., 1989). Up to now only two obvious Triterpenoids resembling lupeol were isolated
cytotoxic macrocyclic diterpenoids ester have been from the latex of Turkish E. helioscopia L. with structures
reported from this plant during the past decades: confirmed as 19αH-lupeol (56) (Nazir, 1998); lup-20(29)-
euphornin (39) (Lu, 2008; Jassbi, 2006) and euphornin L ene-3-acetate (57) and lup-20(29)-ene-3-palmitate (58);
(40) (Tao, 2008). Three new diterpene analogues, together with common triterpenoids, were also found and
euphoheliosnoids A-C (41-43), have been isolated from identified as: 24-methylene cycloartanol (59), 24-
E. helioscopia L. which collected in Shujiae, Zhejiang methylene cycloart-3-one (60), cycloartanol (61) and
province, China; all of these new compounds stigmast-4-ene-3-one (62) (Barla A et al., 2006).
demonstrate considerable spectral analogy with the
previously reported euphoscopins but they are either Flavonoids
esterified differently at C-7 or oxidized with Flavonoids are popular compounds for
accompanying migration of a double bond at C-11 (Zhang chemotaxonomic surveys of plant genera and families.
W et al., 2005). Additionally investigation of this plant Several studies indicated that flavonoids occur in E.
collected from Zhejiang province has led to the isolation helioscopia Linn. The qualitative composition of
of a new diterpenes with a jatrophon type skeleton, named flavonoids in alcoholic extract of E. helioscopia indicated
euphoheliosnoid D (44) (Zhang W et al., 2006). 15 substances with flavonoidal nature. By 2-dimensional
paper chromatography (2-DPC) after acid hydrolysis of E.
Jatrophane-type diterpenes helioscopia alcoholic extract by Volobuevra (1970) and
From the aerial parts of Euphorbia helioscopia, Abd-Salam (1975) two compounds were characterized:
collected from Istanbul, Turkey, a jatrophane diterpene quercetin and kaempferal. E. helioscopia appears to have
ester, 5,11-jatrophadiene-3- benzoyloxy-7,9,14-tri- low flavonoids verity compared with other Euphorbia
acetyloxy-15-ol (45) (Barla A et al., 2006). Other novel species In the leaves, flavonoid sulphate and flavone C
diterpenes were isolated and identified as jatrophane and C-O- glycosides) (Noori M et al., 2009; Aqueveque P
skeleton type, named euphoscopin M (46), euphoscopin et al., 1999) have been reported. Quercetin-3-β-glucoside,
N (47) and euphornin L (48) were isolated from the whole quercetin-3-β-galactoside and quercetin-3-β-galactoside-
plant collected at the Saepinum ruins, in Altilia, Italy 2``-galate were isolated from E. helioscopia (Pohl R et
(Barile E et al., 2008; Corea G et al., 2009). From the al., 1975).
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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Tannins chromatography saturated and unsaturated fatty acids

E. helioscopia L., unlike other Euphorbia series ranging from lauric (C12) to cerotic (C26) were present
so far examined contains large numbers of novel with palmitic acid (C16) being the most predominant.
ellagitannins. A study by Lee (1990) reports the isolation Alkanes ranged from henocosane (C21) to
of four hydrolysable tannins named helioscpinins A and B heptatriacontane (C37) with hentriacontane (C31) as the
and helioscopins A and B having a variety of major product. The alkanols ranged from behenyl (C22)
phenolcarboxylic acid ester groups. Further chemical to myricyl (C30) with ceryl (C26) as the max. β-Sitosterol
study on tannins of this plant has led to the isolation of was the major component (97.35%) of the sterol fraction
two minor hydrolysable tannins named euphorscopin and (Nazir M et al., 1983).
euphorhelin (Lee SH et al., 1991).
The epicuticular waxes of E. helioscopia were
Polyphenols fractionated into fatty acids, hydrocarbons, wax esters,
Two studies of the polyphenol constituents from aldehydes, methyl esters, triterpenol acetates, alcohols,
E. helioscopia have been reported: from E. helioscopia sterols and polar components. The components of the
collected from Uzbekistan among various Euphorbia fractions were determined by gas chromatography GC,
species growing in the Fergan valley, quercetin, GC-mass spectrometry, and HPLC. The main components
quercetin-3-O-glucoside, and 1,2,3-tri-O-galloyl-β-D- within these lipid classes were hentriacontane the wax
glucose (Abdulladzhanova NG et al., 2003) were isolated. esters C-46 and C-48, octacosanal, hexacosanol and
Form Chinese species: gallic acid, methyl gallate, octacosanol, hexadecanoic acid and β-sitosterol. Lupeol
pyrogallol,(-)-shikimic acid-4-O-gallate, (-)-shikimic and its acetate were also confirmed. (Nazir M et al.,
acid-O-gallate, 1-O-galloyl-2,3-HHDP-α-D-glucose, 1993).
1,3,6-tri-O-galloyl-β-D-glucose, 1,2,3,6-tetra-O-galloyl-
B-D-glucose, resorcinol, gallic acide-4-O-(6`-O-galloyl)- The distribution of hydrocarbons in the surface
β-D-glucose were isolated (Feng WS et al., 2009). The wax of E. helioscopia was also studied. In addition to
chemical constituents of fruits and roots of E. helioscopia homologous series of n-alkanes, minor quantities of
were analyzed by a high- performance liquid unsaturated and branched hydrocarbons were also
chromatography. The major components were quercetin, detected. Some of the branched chain hydrocarbons could
quercitrin and subgallate (He XG et al., 1978). be explained as having originated from isoprene units and
the substituents corresponding to diterpenes and
Glycosides triterpenes (Ahmed W et al., 1996).
The whole plant of E. helioscopia L. were
collected in Xixia county, Henan province, China, E. helioscopia seeds contain 28% oil (Hossain
extracted with 50% aqueous acetone, yield a new aryl MG et al., 1993), the oil isolated from the seeds of E.
glycoside, 3``-O-galloyl-benzyl-D-α-L-rhamnopyranosyl- helioscopia and the natural mixture of fatty acids derived
(1-6)-β-D-glucopyranoside (63) (Feng WS et al., 2009). from the oil contains lauric acid 2.85 %, myristic acid
5.49 %, palmitic acid 9.18 %, stearic acid 1.13 %, oleic
Lipids, fatty acids, waxes & hydrocarbons acid 15.80 %, linoleic acid 22.14 %, and linolenic acid
In a study of the neutral lipids from the leaves of 42.71 % (Durrani AA et al.,, 1967; Nazir M et al., 1986;
E. Helioscopia, wax esters composed of lauric, 1.35%, Vioque J et al., 1994; Doe J, 2010; Yamamura S et al.,
myristic 5.24 %, palmitic 39.30%, stearic 13.27%, oleic 1981).
15.66%, linoleic 2.30%, arachidic 19.14%, behenic acid
3.80% and higher fatty alcohols were isolated. Octacosyl Volatile oil
alcohol and β-sitosterol were found in both in the free and Only two studies on the volatile oil of E.
esterified form. Heptacosane and triterpenoidal acetate helioscopia have been reported. In Saudi Arabia, E.
(C32H52O2) were isolated from the hydrocarbon fraction, helioscopia amongst other local plants was investigated
and the terpenoidal ester fraction respectively (Nazir MA for their volatile oil constituents, with the major
et al., 1977). In a separate study, the neutral lipids were constituents being elemol and β-eudesmol (Baghlaf AO et
extracted with hexane in 2.8% yield and resolved into an al., 1983). The analysis of steam volatile oil obtained
acidic fraction (28.7%) and a neutral fraction (71.1%). from the inflorescence of E. helioscopia was reported;
The normal monocarboxylic acids (19.26%), the resulted in the identification and quantification of 40
hydrocarbons (9.94%), the monohydric alcohols. constituents (94.3%) were identified and quantified. The
(35.53%), and the sterols (5.61%) were isolated from the major compounds were phytol (21.2%), trans-
acidic fraction and the neutral fraction by column Caryophyllene (10.0%) and docosanoic acid methyl ester
chromatography. In the anlysis by gas liquid (8.1%) (Fokialakis N et al., 2003).
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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Biological Activities organs of E. helioscopia significantly decreased the

Vasodepressor Activity seedling vigor index and growth of test crops. Leaf extract
The crude extract of the Turkish E. helioscopia had a greater inhibitory effect than the other extracts.
were partitioned against petroleum ether and then CH2Cl2, Water extracts from the root, stem, leaf, and fruit of E.
which give 4 fractions (A-D) thus fractions were further helioscopia resulted in a reduction in the seed germination
submitted to silica gel column chromatography to yield 7 (chickpea and lentil only) and germination index but the
pure compounds. The fractions and the compounds were leaf extract increased the mean germination time in all
tested for their vasodepressor effects using Wistar Albino test crops.
rats. Among the compounds, 5,11-jatrophadiene-3-
benzoyloxy-7,9,14-tri-acetyloxy-15-ol (45) was the most Insulin secretagogue activity
active vasodepressor (42 mmHg). The period for the A study by Hussain (2004) of E. helioscopia
effective reduction of blood pressure was 45 min. this amongst medicinal plants, collected from Islamabad and
effect lasted 70 min and did not return to normal during the Murree region of Pakistan, were carried out to look
this period. Compound lup-20(29)-ene-3-acetate (57) into the effect of these medicinal plants on insulin
dropped blood pressure by about 34 mmHg; this effect secretion from INS-1 cells. INS-1 cells secrete insulin
continued for 45 min. compound stigmast-4-ene-3-one without peracrine influence dried ethanol extracts of all
(62) had the lowest vasodepressor effect (28 mmHg); plants were dissolved in ethanol and DMSO, and tested at
however, it returned to normal after 30 min. the various concentrations (between 1 and 40 µg/mL) for
vasodepressor effect of these compounds might be due to insulin release from INS-1 cells in the presence of 5.5
vasorelaxation activity (Barla A et al., 2006). mM glucose. Glibenclamide was used as a central.
Promising insulin secretagogue activity in various plant
Anti-Allergic & anti-asthmatic activity extracts at 1, 10, 20 and 40 µg/mL was found, while E.
A study by Park (2001) indicates an inhibitor of helioscopia was active at 10 µg/mL (p < 0.05).
leukotriene D4-induced tracheal contraction was isolated
from E. helioscopia this isolated polyphenol compound, P-glycoprotein & BCRP- inhibiting activity
known as helioscopinin-A showed a certain inhibitory The isolated compounds; jatrophane diterpenes
activity on capillary permeability in passive cutaneous (50-52, 6, 8, 39, 43) and lathyrane (59) from the whole
anaphylaxis responses of rats and also on antigen-induced plant of E. helioscopia L. exhibited in vitro activity as
bronchial constriction in an experimental asthma model of inhibitors of P-glycoprotein (ABCB1) among them
guinea pigs. The compound at a high concentration epieuphoscopin B (39) behaved as the most potent
weakly inhibited histamine release from isolated mast inhibitor of mitoxantrone efflux activity, being twice as
cells of rats. It is suggested that this compound is an anti- efficient as the reference inhibitor cyclosporine A.
allergic and anti-asthmatic which exerts its activity structure activity relationships among jatrophanes showed
through antagonism on leukotriene D4-induced responses. the importance of substitution at positions 7 and 9.
Interestingly, these compounds appear to be specific P-
Allelopathic effect glycoprotein inhibitors since they show an absence of
Studies by Tanveer (2010) investigating the significant activity against BCRP (ABCG2), despite the
Allelopathic effect of root, stem, leaf, and fruit water high substrate overlapping of these transporters, thus
extracts and infested soil of E. helioscopia L. on the seed including them in the third-generation class of specific
germination and seedling growth of wheat, chickpea, and multidrug transporter modulators. (Barile E et al., 2008).
lentil were conducted in a completely randomized design The jatrophane compounds and lathyrane diterpenes by
with 4 replications. Water extracts of root, stem, leaf, and Corea (2009) from the E. helioscopia investigated for
fruit were prepared by soaking dried plant parts of E. their Pgp- and BCRP-inhibiting properties, appeared to be
helioscopia in water (1:20 w/v) for a period of 24 h. specific inhibitors of Pgp since they showed no significant
Seedling emergence, seedling vigor index, and total dry activity against BCRP, thus resembling to the third
weight of wheat, chickpea, and lentil seedlings were generation class of specific MDR inhibitors. Thus, owing
significantly reduced when these crops were grown in soil to the bulk availability of Euphorbieae plants and the
taken from an E. helioscopia infested field compared to relatively easy isolation of the major constituents of the
soil collected from an area free of any vegetation. E. diterpenoid fraction, these plants can be qualified as an
helioscopia infested soil also significantly decreased the interesting source of bioactive chemotypes for detailed
root length of wheat and lentil, and shoot length of lentil structure-activity studies on emerging new classes of lead
compared to the control soil. Water extracts of various compounds.
 83
Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Antibacterial activity from E. helioscopia had more than 90% inhibition rate to
E. helioscopia amongst 109 species of Iranian the spore germination of at least one fungus tested
plants were screened for antimicrobial activity. The (Shunyi Y et al., 2006). Dichloromethane and methanol
results show that E. helioscopia was active against extracts of the aerial parts of E. helioscopia were tested
Bacillus anthracis and inactive against Klebsiella against Trichphyton longifusus, Candida albicans,
pneumoniae, Proteus vulgaris, Shigella sonei, Vilorio Aspergillus flavus, Microsporum canis, Fusarium solani
cholerae, Escherichia coli, Saphylococcus aureus and and Candida glabrata. Dichloromethane extract showed
Salmonella paratyphi A. (Surmaghi SMH et al., 1993). 90% Inhibition against Fusarium solani, at the
The solvent extracts of E. helioscopia, which were concentration of 400 μg /ml for incubation period of
extracted by using several solvents with different seven days at 27 °C with reference to miconazole as
polarities (Kim JY et al., 2007), were prepared for utility standard. While methanol extract was found to be inactive
as natural preservatives. The E. helioscopia extract by (Uzair M et al., 2009). Petroleum ether, dichloromethane,
80% ethanol was sequentially fractionated with n-hexane, methanol extracts of E. helioscopia were tested by
dichloromethane, ethylacetate, and butanol. In order to Chaudhry (2001) for their antifungal activity against
effectively screen for a natural preservatives agent, the Claudosporium cucumerinum, the three extracts were
antimicrobial activities and cell growth inhibition were devoid of antifungal activity. Loothar and Choudhary
investigated for each strain with the different (2009) stated that dichloromethane extract of the aerial
concentrations of E. helioscopia extracts. Antimicrobial parts of the plant exhibited significant activity against
activities were shown in ethylacetate fraction of E. Fusarium solani with 90 % Inhibition.
helioscopia; however, ethanol, butanol and water
fractions showed weak antimicrobial activity against the Antiviral activity
tested microorganisms. Among the five fractions, Ramezani (2008) investigated E. helioscopia
ethylacetate fraction showed the highest antimicrobial extracts for the antiviral effects using plaque reduction
activities against microorganisms tested, such as Bacillus assay. Plant extracts were prepared using Soxhlet
sublitis, Listeria monocytogenes, Staphylococcus aureus, apparatus or by maceration in methanol after applying
Escherichia coli, Pseudomonas aeruginosa, Salmonella several enriching stages of phage CP51, phage titration
Enteritidis and Salmonella Typhimurium. The polyphenol was performed to determine the phage concentration in
content from ethanol, n-hexane, dichloromethane, phage lysate for specifying the dilution factor of the
ethylacetate, butanol, and water fractions were 207.46 phage to be used as negative control or the next working
mg/g, 45.45 mg/g, 138.23 mg/g, 678.02 mg/g, 278.91 stages. Then IC50 of trifluridine, as a positive control, for
mg/g, and 63.76 mg/g, respectively. Antibacterial activity phage CP51 was determined. The MIC of extracts for
of the Dichloromethane and methanol extracts of the Bacillus cereus was determined as 1.25 and 0.5 mg mL-1
aerial parts of E. helioscopia was performed against for Soxhlet and maceration extracts, respectively. To
Eschericha coli, Bacillus subtilis, Shigella flexenari, determine whether the extracts have the ability to inhibit
Staphylococcus aureu, Pseudomonas aeruginosa and the adsorption of virus to host cell, it was pre-incubated
Salmonella typhi. Both the extracts exhibited non- with phage CP51 for 30 min at 25 °C. The growth and
significant activity against Bacillus subtilis and reproduction of phage was inhibited by more than 50% at
Salmonella typhi at the concentration of 3 mg /ml (Uzair, concentration of 1 and 0.25 mg mL-1, respectively. In
2009). In the study of the Petroleum ether, order to test the effects of extract on transcription process,
dichloromethane, methanol extracts of E. helioscopia Bacillus cereus, phage CP51 and extract were incubated
were tested by Chaudhry (2001) for antibacterial activity together. The growth and reproduction of phage was
against Sacina leutea and Escherchia coli, only the inhibited by more than 50% at concentration of 0.75 and
methanol extract show antibacterial activity. Meanwhile, 0.125 mg mL-1 or Soxhlet and macerated extracts,
Loothar and Choudhary (2009) stated that respectively. These results indicated that both extracts of
dichloromethane extract of the aerial parts of the plant E. helioscopia have considerable antiviral activity.
showed non-significant activity against Salmonella typhi Cytotoxic activity
and Bacillus subtilis. Zhang (2004) studied the crude extract of E.
helioscopia and the isolated compounds euphoheliosnoids
Antifungal activity A-C, the crude extract exhibited cytotoxic activity against
The fungistatis of 14 plant extracts including E. murine leukaemia P388 cells, but euphoheliosnoids A-C
helioscopia against Botrytis cinerea, Rhizoctonia, solani, proved to be inactive. The cytotoxicities of compounds
Fusarium oxysporum, Cladosporium cucumerinum and euphoscopin A (1), euphoscopin B (2), euphoheliosnoid
Alternaria solani was tested in vitro using growth rate and A (6), euphoscopin C (8), euphoscopin F (27),
spore germination methods. The concentration of the epieuphoscopin B (39), euphornin (43), euphornin L (52)
extracts was 0.1 g/mL. The results showed that the extract were assayed using the HL-60 cells by MTT
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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

method, and A-549 cells by SRB method. And VP-16 dichloromethane, ethylacetate, and butanol. In order to
(etoposide) was used as the positive control with IC 50 effectively screen for a natural preservatives agent, the
values of 0.04 and 0.63 μM, respectively. Compounds antioxidant activities investigated such as DPPH radical
(52) and (27) exhibited cytotoxicity against HL-60 with scavenging capacity, superoxide radical scavenging
IC50 values of 2.7 and 9.0 μM, respectively, while the capacity, and xanthine oxidase inhibitory activity of the E.
other compounds were inactive (IC50 > 100 μM). (Tao, helioscopia extracts. By the screening system, we found
2008). All isolated compounds by Lu (2008) were that ethylacetate fraction had the strongest antioxidant
evaluated for cytotoxicity against HeLa human cervical activity in a dose⁃dependent manner. From these results,
carcinoma cells and MDA-MB-231 breast tumor cells. it is suggested that E. helioscopia could be used for the
Only two of these compounds, helioscopinolide A (3) ethylacetate fraction and could be suitable for the
(IC50 0.11 and 2.1 μM, respectively) and euphornin (43) development of a food preservative (Kim JY et al., 2007).
(IC50 3.1 and 13.4 μM, respectively), were found to be Uzair (2009) studied Dichloromethane and methanol
cytotoxic for the HeLa and MDA-MB-231 cells. All other extracts of the aerial parts of E. helioscopia L. for their
compounds were inactive (IC50 > 10 μM) for both cell antioxidant activity. The antioxidant activity (free radical-
lines. Seventy-three hydrolyzable tannins and related scavenging properties) of both extracts was evaluated by
compounds were isolated from seven Euphorbia plants thin layer chromatography (TLC) autographic assay
including E. helioscopia. Among them, 28 compounds method, using 2,2-Diphenyl-1-(2,4,6 trinitrophenyl)
including nine gallotannins, eleven ellagitannins and eight hydrazyl (DPPH) as spray reagent. Methanolic extract
related compounds were selected according to structural appeared as a yellow spot against purple background
similarity. Cytotoxicity of them on the human tumor cell because of the components responsible for free radical-
lines including A-549, SK-OV-3, SK-MEL-2, XF-498 scavenging properties when tested at 100μg
and HCT-15 were evaluated by the SRB method in vitro. concentration, whereas dichloromethane extract did not
3,4,6-Tri-O-galloyl-D-glucose was shown to exhibit the respond to DPPH.
most potent cytotoxic effect (4.4 μg/mL〈ED50〉10.3
μg/mL) (Lee SH et al., 1997). Cholinergic activity & Brine shrimps toxicity
The cholinergic activity of the E. helioscopia
Antitumor activity extracts (petroleum ether, dichloromethane, methanol)
Antitumor activity of the aquatic extract the root was studied by using isolated guinea-pig ileum and rabbit
of E. helioscopia L. (EWE) in Vitro were studied. Viable jejunum preparations. Guinea-pig (500-600 g) of a local
cells count, MTT staining and colonal formation assays of breed and of either sex was used for this study. The
three kinds of cancer cells were used to assess the results show that all extracts were devoid of cholinergic
antitumor activity. Determined by viable cells count, the activity (Chaudhry BA et al., 2001). Also the same
IC50 values of EWE against 7721, HeLa, MKN-45 cells extracts were tested for brine shrimps toxicity, the
were 1.26, 1.98, 1.72 mg/ml respectively (72 h). petroleum ether and dichloromethane show brine shrimps
Determined MTT staining, the IC50 values EWE against toxicity while the methanol extract had no activity.
7721, HeLa, MKN-45 cells were 1.43, 1.67, 0.97 mg/ml.
Determined by colonal formation, the inhibition rate of In vitro mushroom tyrosinase activity
EWE (4 mg/ml) against 7721, HeLa, MKN-45 cells were Nineteen hydrolyzable tannins isolated from the
59.8%, 66.4%, 70.5%. The results indicated that EWE E. helioscopia were tested for the inhibitory effect on
had obvious antitumor activity (Cai Y et al., 1999). β- mushroom tyrosinase activity in vitro. Inhibitory effect of
sitosterol, euphornin, euphornin D, euphohelioscopin A, gallotannin group was more potent than that of
quercetin, gallic acid, caffeic acid, Et gallate, myricetin, phenolcarboxylic acid and ellagitannin groups against the
and hyperoside were isolated from the ethanol ext. of E. enzyme activity. The inhibitory activity by pentagalloyl
helioscopia L. The antitumor activities of the isolated glucose on mushroom tyrosinase was more potent (IC50,
compounds on LA795 cells were also conducted. Gallic 4.9 μM) than that of kojic acid (IC50, 8.7 μM) (Kim JJ et
acid and hyperoside were reported as the antitumor al., 2001).
constituents of E. helioscopia L. for the first time (Yang L
et al., 2008). Molluscicidal activity
Molluscicidal activity is widespread in the
Antioxidant activity family Euphorbiaceae, although activity varies greatly
The solvent extracts of E. helioscopia, which from species to species and even between different parts
were extracted by using several solvents with different of the same plant. Al-Zanbagi (2000) studied E.
polarities, were prepared for utility as natural helioscopia together with two other plants from the family
preservatives. The E. helioscopia extract by 80% ethanol Euphorbiaceae from Saudi Arabia to identify those parts
was sequentially fractionated with n-hexane, of the plants that had molluscicidal activity against
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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Biomphalaria pfeifferi. The results showed that extracts of Pesticidal activity

E. helioscopia and E. schimperiana both showed promise Some extracts of E. helioscopia, Calendula
as molluscicides. The methanol extract of dry leaves of E. micrantha and Azadriachta indica were screened for the
helioscopia had an LD50 of 50.8 ppm and an LD90 of 68.2 control of Culex pipiens larvae, the vector of Filariasis
ppm. Using acetone extracts of the same plant Shoeb and and Biomphalaria alexandrina snails, the vector of
El-Sayed (1984) and El-Amin and Osman (1991) Schistosomiasis in Egypt. Results showed that the acetone
recorded higher activities than those obtained in this extract of E. helioscopia was the most toxic extract
study. Later, Al-Zanbagi (2005) studies the Molluscicidal against both C. pipiens larvae and B. alexandrina snails
properties of the E. helioscopia against the snail Bulinus with LC50 of 50.58 and 10.13 ppm respectively, whereas
wrighti. The results showed that the cold water and hot the benzene extract showed the lowest activity with LC50
water extracts of E. helioscopia gave good results (LC50 = 98.01 and 30.1 ppm against both pests respectively.
of 80 ppm and 96.6 ppm respectively) against the snails Other extracts showed moderate toxicity towards the two
Bulinus wrighti. The methanol, acetone and hexane pests (Elyassaki WM et al., 1996). In a study carried out
extracts gave a big difference results against the snail by Heng-Guo H.E. (2010), ethanol extract from E.
Bulinus wrighti rather than reported for Biomphalaria helioscopia showed contact toxicity (LC50= 870.25
pfeifferi. The choloroform extract has less molluscicidal mg/L) and antifeedant activity (AF50 of antifeeding ratio
activity against Bulinus wrighti in comparison with those was 23.71 mg/L.) against 2nd instar larvae of the
of Biomphalaria Pfeifferi. Lepidopteron moth, Pieris rapae.

Fig. 1. Jatrophon type diterpenoids of E. helioscopia

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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Fig. 2. Lathyrane diterpenes of E. helioscopia

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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Fig. 3 Triterpenes of E. helioscopia

Fig.4 Glycosides of E. helioscopia

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Abou-El-Hamd H. Mohamed. et al. / International Journal of Phytopharmacology. 3(1), 2012, 78-90.

Conclusions and future perspectives and commercial use of this plant, trials should be done to
The available literature indicating various validate the relevant concentrations and the economic
biological and therapeutic activities of E. helioscopia. values of using these biorationals in different biological
Large scale experiments would be required to substantiate and therapeutic applications. Assessments have to be
the efficacy of the different classes of secondary extended to establish various limitations about their
metabolites isolated from this plant. For the wide scale mammalian and environmental safety.

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