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Antioxidant and Antiangiogenic Properties, and Gas Chromatographic-Time of Flight Analysis of Sonchus arvensis Leaves Extracts.

Byline: Afrizal Itam, Amin Malik Shah Abdul Majid and Zhari Ismail

Summary: Sonchus arvensis L. (Asteraceae) is one of the medicinal herbs used in traditional medicines, in which the leaf extract was used as a diuretic, lithotriptic and antiurolithiasis agent. The leaves of S. arvensis reported contain several compounds, including a variety of flavonoids, terpenoids and sterol, even this plant also contain silica and potassium. Flavonoids are secondary metabolite compound which have ability as antioxidant. In this study, the aims are to determine of antioxidants and antiangiogenic properties, and phytoconstituents quantitative of aqueous and methanol extracts of S. arvensis leaves. The antioxidant properties were studied using 1,1-Diphenyl-2-picrylhydrazyl (DPPH) free radical, xanthine oxidase and b-carotene-linoleate models system.

Furthermore, the antiangiogenic property was evaluated using ex vivo rat aorta ring assay. Quantitative determination of extracts phytoconstituents were carried out by using Gas Chromatographic-Time of Flight (GC-TOF) mass spectrophotometric methods. The results showed that the aqueous and methanol extracts have ability as antioxidant which is antioxidant activities of aqueous extracts on DPPH radical and inhibition of xanthine oxidase activity are higher than that of methanol extracts. Meanwhile antioxidant activity using b-carotene-linoleate model system of S. arvensis aqueous extract is lower than that of methanol extracts. Nevertheless, the differences of these antioxidant activities are not significant. Antiangiogenic property of aqueous extract is also higher than that of methanol extract which is measured at 100 g mL-1.of extracts.

This indicates that there is correlation between antioxidant activity and antiangigenic property, exhibiting that this plant possesses the potential to prevent or cure the diseases that related to angiogenesis such as cancer.

Keywords: Sonchus arvensis; Asteraceae; antioxidant properties; antiangiogenic properties; GC/TOF-MS.

Introduction

The usage of plants as source of medicine have been used by world community for thousand years in maintaining health as an alternative to or in conjunction with modern medicines. The World Health Organization (WHO) estimated about 70% of the world population uses medicinal plants for medicines, and they are highly used mainly in Asia, South America and Africa [1]. In addition, combination of traditional and modern medicine has an important role in promoting health care system. In many countries, herbal medicine is making a strong comeback and the world of medicine today embraces both single pure chemical entities and herbal medicine side by side [2].

One of disease that treated with herbal medicine was cancer. Angiogenesis plays an important role in the growth and spread of cancer. New blood vessel feed the cancer cells with oxygen and nutrients, allowing these cells to grow, invade nearby tissue, spread to other part of the body, and form new colonies of cancer cells. Cancer cannot grow or spread without the formation of new blood vessels [3-6]. Antiangiogenic agent is the chemicals or drugs which can inhibit or reduce the new blood vessel formation. Therefore, antioxidant and antiangiogenic properties of medicinal plants have potential for prevention and treatment of cancer diseases.

Sonchus. arvensis L. (Asteraceae) is one of traditional medicinal herbs, easy to grow in rainy and sunshine areas, such as on riverbanks, ridges of rice field and abandoned fields 50-1650 meters above sea level, native from Eurasia. The local names are tempuyung (Indonesia), Niu she tou (China), Laitron des champs (France), Sow thistle (British). Traditionally, leaves extract of this plant was used as a diuretic, lithotriptic and antiurolithiasis agent; also indicated for fever, poisoning and swelling or abscess [7-11]. The leaves of S. arvensis reported contain several compounds, including a variety of flavonoids, terpenoids and sterol, even this plant also contain silica and potassium [12-20]. Flavonoids are secondary metabolite compound which have ability as antioxidant.

In this study we developed the quantitative determination of phytoconstituents of S. arvensis leaves extracts using GC-TOF mass spectrophotometric methods. Furthermore, in this study we also determined bio-pharmacological properties, including antioxidant and antiangiogenic properties of S. arvensis leaves extracts. The antioxidant properties of extracts were studied using DPPH free radical, xanthine oxidase and b-carotene- linoleate models, and the antiangiogenic property of extracts was studied by using in vivo rat aorta ring assay. In this case, we used methanolic and aqueous extracts, because the methanol can dissolve almost all secondary metabolite including flavonoids, and water also can dissolve flavonoids, especially for glycoside flavonoids. In antioxidant properties study, we used gallic acid, ascorbic acid, quercetin and BHA as reference compounds because these compounds have reported having antioxidant properties and often use as reference compounds in antioxidant activities.

Experimental

Chemicals and Reagents

Methanol, ethanol, sulphuric acid, chloroform and thin layer chromatography (TLC) plate Silicagel 60 F254 were obtained from Merck, Darmstadt, Germany. Potassium dihydrogen phosphate, dipotassium hydrogen phosphate were obtained from R and M Chemicals, Essex UK.

DPPH radical, gallic acid, quercetin, butylated hydroxyl anisole (BHA), xanthine oxygene oxidoreductase EC 1.1.3.22, xanthine (2,6-Dihydroxypurine), b-carotene, linoleic acid, Tween-40, butylated hydroxyl toluene (BHT), lupeol, aprotinin, thrombin (EC 3, 4.21.5), foetal bovine serum (FBS), amphotericin B (fungizone), gentamycin, -aminocaproic acid, Phosphate-Buffered saline (PBS) and sodium chloride were purchased from Sigma Chemical Company St. Louis MO, USA. Ascorbic acid was purchased from Univar Ajax Chemical, Australia. M199 was obtained from Gibco BRL. Fibrinogen was purchased from Calbiochem, La Jolla, California. Dimethylsulfoxide (DMSO) was acquired from J. T Baker Inc. USA..

Instruments

Determination of antioxidant activity was used spectrometer UV/ VIS Lambda 45 Perkin- Elmer. Antiangigenesis study was used curve-tip forceps, straight-tip forceps and small dissecting scissors were used for surgery and to cut rat aorta. Incubation of tissue was carried out at 37 C incubated in 5% of carbon dioxide using the Binder CB150 incubator. The blood vessel growth of rat aorta was prepared under a dissection microscope (Leica DMLB) attached with a Leica DC 300 camera (Cambridge, England) connected to Leica Compaq Workstation. Captured images areas were measured using QWIN Plus Software. Quantitative analysis of extracts was used gas chromatography/time of flight mass spectrometry (GC-TOF-MS): a Hewlett- Packard 6890 GC coupled with a LECO Pegasus II reflectron time-of-flight mass spectrometer with electron impact ionization, equipped with Chrom TOF mass data analysis system.

A DB-WAX fused silica capillary column (20 m x 0.18 mm, I.D; 0.18 m film thickness) and Helium as carrier gas (1 mL/min) were used.

Sample of Sonchus Arvensis

S. arvensis leaves were collected from Padang, West Sumatera Indonesia. The plant was identified and the specimen was deposited in herbarium of Biology School, University of Sciences Malaysia with reference number is 10932. The fresh leaves were washed and dried in the oven at 40 C, and then milled into powder.

Extraction

Five gram of the dried sample was macerated with 200 mL of water and methanol in separate flasks at their boiling points for 6 hours. After cooling, the mixtures were filtered and the filtrates were dried using a vacuum evaporator and stored in freezer using airtight container.

Determination of Antioxidant Activities

Dpph Free Radical Scavenging Activity

Free radical scavenging activity (FRSA) of extracts was determined according to Akowuah et al., Abdille et al. and Yuan et al. with some modifications [21-23]. Solutions of 25, 50, 100, 200, 400, and 600 L of 1000 g.mL-1 of aqueous and methanol extract solutions was placed in the separate tubes and the volume was made up to 1 mL with methanol. To this mixture, 5 mL of 0.1 mM DPPH was added. After 30 minutes of incubation at room temperature, absorbance was measured at 517 nm using spectrometer UV/ VIS Lambda 45, against methanol as the blank. Volume of 1, 2, 4, 10, 20, 40, 60, and 80 L of 500 g.mL-1 gallic acid, ascorbic acid, quercetin and BHA were used as references and 5 mL of 0.1 mM DPPH was used as the reagent.

A control is containing 1 mL of methanol and 5 mL of 0.1 mM DPPH. The experiments were carried out in triplicate. Free radical scavenging activity (AA- FRSA) of the extracts was determined as following formula:

(Equation)

where As and Ac are absorbance of sample and control, respectively. Effective concentration 50% (EC50) was calculated using regression equation from the calibration curve obtained from the graph of extract concentrations (X-axis) plotted against FRSA percentage (Y-axis).

Antioxidant Assay Using b-Carotene-Linoleate Model System

Antioxidant assay using b-carotene-linoleate model system of S. arvensis extracts was analyzed according to Abdille et al. [22] with modifications. 0.2 mg of b-carotene in 0.2 mL chloroform, 20 mg of linoleic acid and 200 mg of Tween-40 (polyoxyethylene sorbitan monopalmitate) were mixed. Chloroform was removed under vacuum at 40 C and resulting mixture was diluted vigorously with 10 mL water. To this emulsion, 40 mL of oxygenated water was added. 4 mL aliquots of the emulsion were pipetted into separate test tubes containing 0.2 mL of 200 g.mL-1 extracts, quercetin, BHA and BHT in ethanol. Quercetin, BHA and BHT were used for comparative purposes.

A control containing 0.2 mL of ethanol and 4 mL of the above emulsion was prepared. The test tubes were placed at 50 C in a water bath and the absorbance was measured at 470 nm (absorbance at zero time, t = 0) using UV/VIS Lambda 45 spectrometer. The next absorbance was measured after 120 minutes of incubation. A blank with a similar mixture was prepared without the presence of b-carotene. All analyses were carried out in triplicate. The antioxidant activity on b-carotene (AA b-C) was evaluated using the following formula:

(Equation)

where A0 and A0 are the absorbance value measured at zero time of the incubation for test sample and control, respectively. At and At are the absorbance values were measured after incubation for test sample and control, respectively. The results were expressed in percentage (%) of bleaching inhibition of b- carotene.

Inhibition on Xanthine Oxidase Activity

Xanthine oxidase inhibitory activity of S. arvensis extracts were determined according to Sweeny et al. [24] with modification. 0.5 mL of 100 g.mL-1 extracts solution, 1.3 mL of buffer phosphate solution pH 7.5 and 0.2 mL of 0.2 unit/mL xanthine oxidase solutions were pipetted into the test tube. After 10 minutes of incubation at room temperature, 1.5 mL of 0.15 mM xanthine substrate solution was added to this mixture. The mixture was incubated for 30 minutes at room temperature and then the absorbance reading was measured at 293 nm using spectrometer UV/VIS against 0.5 mL of methanol, 1.3 mL of buffer phosphate pH 7.5, 0.2 mL of xanthine oxidase and 1.5 mL of water as the blank.

0.5 mL of methanol, 1.3 mL of buffer phosphate pH 7.5, 0.2 mL of xanthine oxidase and 1.5 mL of xanthine substrate solution were used as the control. Allopurinol was used as reference compound that has been used as inhibitory of xanthine oxidase activity. The experiment was carried out in triplicate and the final results averaged between the three data sets. Inhibition percentage of antioxidant activity on xanthine oxidase (AA-XO) was calculated using the formula below:

(Equation)

where As and Ac are absorbance of sample and control, respectively

Antiangiogenetic Activity

The assay was performed according to the method employed by Brown et al. [25] with minor modifications using rat aortic arch ring derived from 8 weeks old male Sprague Dawley rat species. Samples were prepared by dissolved 10 g of sample in DMSO to 1 mL in volume. 10 L of the solutions were diluted with 990 L of medium (M199) supplemented with 20% FBS, 0.1% -aminocaproic acid, 1% L-glutamine, 1% gentamycin and 1% fungazone. A volume of 0.5 ml fibrinogen (3 g.mL-1 in M199) and 2.5 L aprotinin (1 g.mL-1 in PBS) were transferred into each well of a 48-well plate.

Clean artery rings were rinsed five times in M199 growth media and placed in each well (1 ring/well) of a 48 well plate. Then 15 l of thrombin (50 units/ ml in 0.15 M sodium chloride) were added in each well and the plate was incubated for 1 hour at 37 C and 5% CO2. A volume of 0.5 ml of test sample was added in each well while solution of equivalent concentration without sample was added in control wells. Plate was covered and incubated at 37 C and 5% CO2 for 5 days. Plate was observed daily and media was replaced on day 4. The amount of new blood vessel growth was scored at day 5 under 4X magnification. The inhibition percentage of angiogenesis was calculated by formula:

(Equation)

Analysis by GC-TOF Mass Spectrometry

The analysis was based on a method developed by Korytar et al. [26]. Solutions of 1000 g.mL-1 of aqueous and methanol extracts was used for analysis, which was made from 10 mg of the extracts dissolved in methanol to 10 mL. The analytical conditions were GC open program 50 to 250 C (5 min hold) at 20 C /min, splitless injection, injector temperature 200 C, ion source temperature 180 C, mass range 50 - 500 amu, spectral scan rate 20 spectra/sec, volume injected 1 l. Identification of the compounds were carried out by the both NIST (National Institute for Standard and Technology) 1998 Mass Spectral Database and the Terpene Essential Oil Library with the matching of molecular weight was more than 70%.

Statistical Analysis

The results of this experiment analyzed statistically using SPSS 12 (SPSS Inc. Chicago, IL) and the results were expressed as mean standard deviation of triplicate experiments. Furthermore, differences between mean were evaluated by one- way ANOVA and Tukey's-b multiple comparisons at a level of P less than 0.05

Results and Discussion

Determination of Antioxidant Activities

DPPH Free Radical Scavenging Activity

Both aqueous and methanol extracts of S. arvensis were able to reduce the stable radical DPPH to yellow-coloured 1,1-diphenyl-2-picrylhydrazyl by its hydrogen donating ability. This indicates that the extracts have ability as antioxidant on DPPH.

Antioxidant activities of these extracts are shown in Table-1. Antioxidant activities of these extracts are also expressed with effective concentration 50% (EC50) that is the concentration necessary for 50% reduction of DPPH. EC50 of aqueous and methanol extracts, gallic acid, ascorbic acid, quercetin and BHA are presented in Table-2. In general, FRSA on DPPH of aqueous and methanol extracts is almost equal, but statistically FRSA on DPPH of S. arvensis aqueous and methanol extracts are significantly different (pless than 0.05), either for similar concentrations in different extracts (aqueous and methanol extracts) or for the different concentrations (25, 50, 100, 200, 400 and 600 g.mL-1) in similar extracts, except at concentration of 800 g.mL-1. This indicates that the compounds that contained in these extracts are equal but different in percentage.

In this case, phenolics including polyphenolics and flavonoids which are one of components having antioxidant properties that contained in this plant can dissolve in water and methanol with different solubility. . Previously study, researchers reported that there was a positive correlation between phenolic contents and its antioxidant activity [27-30]. Other researcher also reported that the positive correlation between polyphenolic contents of Agaricus blazei and its antioxidant activity and reported that the polyphenolic compounds with one or more other components present in the extracts may contribute to the overall observed antioxidant activity [31-33]. If compared to gallic acid, ascorbic acid, quercetin and BHA as reference compounds, FRSA on DPPH of these extracts is lower as shown in Table-2. Antioxidant activities of these extracts are one by thirteen to one by fourteen when compared to ascorbic acid which in general found in vegetables and fruits.

Table-1: DPPH free radical scavenging activity of S. arvensis leaves extracts.

Concentration of###DPPH free radical activity of extracts

extract (g.mL-1)###(%)

###Aqueous###Methanol

25###2.40 0.12###4.88 0.19

50###5.24 1.16###10.76 0.75

100###13.99 0.58###17.14 0.21

200###29.77 0.63###31.77 1.32

400###59.97 0.94###55.60 0.83

600###87.76 0.64###76.63 0.32

Table-2: Effective concentration 50% (EC50) of aqueous and methanol extracts of S. arvensis and reference compounds to DPPH free radical

No###Extracts###EC50 (g.mL-1)

1###Aqueous###341.2

2###Methanol###366.6

3###Gallic acid###7.5

4###Ascorbic acid###25.4

5###Quercetin###11.8

6###Butylated hydroxyl anisole (BHA)###19.9

Antioxidant Assay Using b-Carotene-Linoleate

Model System

The antioxidant activity of carotenoids is based on the radical adduct of carotenoids with free radicals from linoleic acid. The linoleic acid free radical attacks the highly unsaturated b-carotene models. The presence of different antioxidants can hinder the extent of b-carotene bleaching by neutralizing the linoleate-free radical and other free radical formed in system [34]. Accordingly, the absorbance decreased rapidly in samples without antioxidant, whereas in the presence of an antioxidant, they retained their color, and thus absorbance, for long time [35]. Antioxidant activity of aqueous and methanol S. arvensis extracts, and reference compounds using b-carotene-linoleic acid method are presented in Table-3. These S. arvensis extracts exhibited the ability to prevent the bleaching of b-carotene by linoleic acid with different prevention degree.

Ability of methanol extract higher than that of aqueous extract, and their antioxidant activity percentages observed are significantly different (p less than 0.05). The antioxidant property of the methanol extract is between of 0.28 - 0.31 times to that of quercetin, BHA and BHT. Antioxidant activity on b-carotene-linoleate can caused among others by polysaccharides. Polysaccharides derived from Lysium barbarum fruits reported has antioxidant activity on b-carotene-linoleate. The antioxidant activity of the polysaccharides increases with increasing concentration. At 250 g/mL, the polysaccharides antioxidant activity was valued at 93.7% (36). Polysaccharides can be suspended in water and methanol, so that aqueous and methanol extracts contain polysaccharides.

Table-3: Antioxidant activities of S. arvensis extracts and quercetin, BHA, and BHT as reference compounds using b-carotene-linoleic acid model system

No###Compounds (in)###Antioxidant activity (%)

1.###Aqueous extract###21.50 2.41

2.###Methanol extract###26.93 1.63

3.###Quercetin###87,70 2,01

4.###Butylated hydroxyl anisole (BHA)###95,84 1,11

5.###Butylated hydroxyl toluene (BHT)###95,12 1,86

Inhibition on Xanthine Oxidase Activity

Aqueous and methanol of S. arvensis extracts have ability to inhibit the xanthine oxidase activity. Xanthine oxidase inhibitory activities of 100 g.mL-1. S. arvensis aqueous and methanol extracts to xanthine substrate are shown in Table-4. In this table also are presented xanthine oxidase inhibitory activities of allopurinol as reference compound. Both, xanthine oxidase activities of aqueous and methanol extracts are higher than that of allopurinol. These inhibition percentages observed are significantly different (p less than 0.05). This means that these extracts contained the compounds that have ability to inhibit xanthine oxidase activity.

Table-4: Xanthine oxidase inhibitory activities of 100 g.mL-1 S. arvensis extracts to xanthine substrate

No###Compounds (in)###Antioxidant activity (%)

1.###Aqueous extract###81.73 0.15

2.###Methanol extract###78.81 0.24

3.###Allopurinol###76,39 0,78

Similar with FRSA, inhibitory activity of the extracts on xanthine oxidase activity is caused by the chemical contents in the extracts, for example flavonoids and phenolics. Flavonoids, other certain phenols and polyphenols have been reported to be potent as the xanthine oxidase inhibitors [37-40]. The flavonoids apigenin and luteolin from the flower of Chrysanthemum indicum were shown as xanthine oxidase inhibitory [41]. Luteolin-7-glucoside from Lycopus europaeus was reported to be a xanthine oxidase inhibitor [42, 43]. Other study reported that there is positive correlation between inhibitory activities of the plants extract with their phenolic contents [44], and predicted that most of natural xanthine oxidase inhibitors present in the active Polygonum cuspidatum extracts might be polyphenols [45-47].

Antiangiogenic Activity

Antiangiogenic activity of aqueous and methanol extracts is expressed as inhibition percentages as shown in Table-5. Representative images of the aortic arch tissue slices are shown in Fig. 1. The analyses of each sample were carried out in 6 replicates with the results being quantified on day 5 of the assay in the manner described by Brown et al. (1996). Betulinic acid, a known antiangiogenic agent [48], was employed as the positive control in this technique. The result employing these tissues explants place the inhibition by betulinic acid at 69.44 14.25%. The inhibition levels of aqueous and methanol extracts derived from S. arvensis are 11.60 3.51% and 8.65 2.22% respectively.

Table-5: Inhibition percentages of S. arvensis and betulinic acid as positive control on angiogenic using rat aorta ring assay.

No###Compounds (in)###Angiogenesis inhibition (%)

###1.###Aqueous extract###11.60 3.51

###2.###Methanol extract###8.65 2.22

###3.###Betulinic acid###69.49 14.25

Antioxidants are well known to have potent antiangiogenic activity. Amongst those that have been identified includes phenolics and or flavonoids and betulinic acid. Flavonoids/ phenolics are widespread in the plant kingdom [49-51]. Phenolics and flavonoids compounds are highly water-soluble and have been shown to be antiangiogenic.. It is also possibly for S. arvensis extracts to contain other yet to be identified antiangiogenic compounds besides phenolics or flavonoids given the large number of unknown chemicals present in these plant species.

Analysis by GC-TOF Mass Spectrometry

The GC-TOF-MS chromatograms of S. arvensis extracts are presented in Fig. 2. This figure shows that the chromatogram pattern of methanol and water extracts were not all the similar, but there is a difference, either quantity or intensity of the peak, quantity of peak is expressed on X axis (tR), meanwhile intensity of peak is expressed on Y axis (abundance). This indicates that there are the similarity and difference of components that contained in methanol and aqueous extracts either amount or concentration. The components of these extracts that detected are shown in Table-6. The results of analysis that presented in this table were composition percentage of the components which relative to the total of components and only components having the percentage 1% or greater in the extracts are reported.

Aziridine, 1-vinyl- (13.10%), n-propylacetate (5.64%) and ethanol,2-(2- aminoethoxy) (5.28%) are three of the higher percentage compounds than others in aqueous extract, meanwhile 1-decosene (21.81%), lupeol (10.40%) and cyclobutanol (6.61%) are the higher percentage compounds than others in methanol extract.Furthermore, provisional estimates that the detectable secondary metabolites in S. arvensis extracts are a-sitosterol (1.84%) and phytol (1.84%) in methanol extract, and lupeol, both in methanol (10.40%) and aqueous (0.91%) extracts. a-sitosterol is steroidal compound having a hydroxyl group at C3 position. Steroids are lipids which are non-polar compounds; hence its solubility is higher in methanol than in water. Researchers have indicated that sitosterol may be useful for the prevention of certain cancers, including ovarian, prostate, breast and colon cancers, and reduce blood levels of cholesterol [52].

Phytol found in methanol extract, it is an alcohol, which is a semi polar compound; hence easier to dissolve in methanol than in water. Lupeol was the higher percentage compound in methanol extracts, and was lower percentage compound in aqueous extract. Lupeol is a triterpene having one alcohol group at C3 position enabling it to dissolve in methanol. Previous study, Hooper et al. reported that the presence of lupeol in S. arvensis [53]. Researchers have demonstrated that lupeol may useful as antitumor and/or anticancer activity including leukemia cells, human prostate cancer cells and pancreatic cancer [54-56]. Lupeol and sitosterol are distributed in plant kingdom, which their biosynthesis is via the mevalonic acid pathway. Phytol biosynthesis is also via mevalonic acid pathway which geranylgeranyl pyrophosphate acts as precursor [57]. Besides, phytol is a decomposition product of chlorophyll [58, 59].

Table-6: The quantitative estimation of compounds identified in the methanol and aqueous extracts of S. arvensis leaves detected using GC/TOF-MS, where identification of the compounds were carried out by the both NIST 1998 Mass Spectral Database and the Terpene Essential Oil Library with the matching of molecular weight was more than 70%

###Extracts

###Compounds###Molecular###Methanol###Aqueous

###Formula###tR (sec)###A (%)###tR (sec)###A (%)

Hexadecanoic acid, methyl ester###C17H34O2###751.86###1.42###751.93###0.67

1,2-Benzenediol###C6H6O2###285.96###0.43###286.23###1.43

1,6,10,14-Hexadecatetraen-3-ol, 3,7,11,15-tetramethyl, [E,E]###C20H34O###1237.9###1.42###0###0

1-Decanol,2-hexyl###C16H34O###1121.5###1.29###1121###0.18

1-Decosene###C22H44###1072.9###21.81###1069.6###8.00

2(1H)Naphthalenone,3,5,6,7,8,8a-hexahydro-4,8a-dimethyl-6-1(1-methylethenyl)-###C15H22O###1181.2###5.73###1179.7###0.39

2,5-Dimethoxy-4-(methylsulfonyl)amphetamine###C12H19NO4S###53.66###2.88###0###0

2-Cyclopentene-1,4-dione###C5H4O2###90.96###0.38###91.43###1.38

2-Ethyl-3-oxo-4-pyrrolidin-2-ylidene-butyronitrile###C10H14N2O###0###0###669.13###1.06

2-Hydroxy-5-methylisophtalaldehyde###C9H8O3###0###0###473.93###4.41

2-Trifluoromethyl-3-oxobutanoic acid, ethylester###C7H9F3O3###0###0###60.73###3.06

5-Methoxypyrrolidin-2-one###C5H9NO2###0###0###263.53###1.54

7-Oxabicyclo[4.1.0]heptane,1-methyl-4-(2-methyloxiranyl)-###C10H16O2###676.46###0.59###677.23###1.74

9,12,15 Octadecatrienoic acid, methyl ester [z,z,z]-###C19H32O2###819.26###0.92###819.23###0.16

Acetic acid, anhydride with formic acid###C3H4O3###55.16###1.26###0###0

Acetic acid, hydroxyl-, methylester###C3H6O3###60.86###0.20###63.53###0.15

alpha-Sitosterol###C29H50O###1174###1.84###0###0

Aziridine, 1-vinyl-###C4H7N###0###0###62.23###13.10

Benzaldehyde, 2hydroxy-6-methyl###C8H8O2###472.16###1.17###0###0

Benzofenac methylester###C16H15ClO3###58.43###1.24###0###0

Cendran-diol,8S,14-###C15H26O2###0###0###1213.6###1.16

Cyclobutanol###C4H8O###60.36###6.61###60.43###2.85

Dimethyl Sulfoxide###C2H6OS###82.96###0.46###80.93###4.22

Ethanol,2-(2-aminoethoxy)-###C4H11NO2###0###0###58.13###5.28

Hydrazine carboxamide###CH5N3O###0###0###55.63###2.19

Hydrogen azide###HN3###70.06###1.13###73.23###0.45

Lupeol###C30H50O###1193###10.40###1190.6###0.91

Methane,(methylsulfinyl)(methylthio)-###C3H8OS2###54.16###1.24###0###0

Monoethanolamine###C2H7NO###0###0###56.83###1.33

n-propylacetate###C5H10O2###63.36###2.15###65.53###5.64

Phytol###C20H40O###824.26###1.84###0###0

Propanoic acid, 2-oxo-, methylester###C4H6O3###76.36###0.03###72.03###3.25

Undecane###C11H24###195.46###0.41###0###0

Conclusion

Aqueous and methanol extracts of S. arvensis have ability as antioxidant to inhibit either to free radical, xanthine oxidase or b-carotene-linoleate.

Antioxidant activities of aqueous extracts on DPPH radical and inhibition of xanthine oxidase activity are higher than methanol extracts. Meanwhile antioxidant activity using b-carotene-linoleate model system of aqueous extract is lower than methanol extracts. Antiangiogenic property of aqueous extract is also higher than that of methanol extract. This means that S. arvensis leaves extracts potent to inhibit or prevent and even used to cure angiogenic diseases.

Acknowledgements

We are thankful to Mr. Noramin from Kulim Hi Tech for the assistance provided with the Mass Spectrometry studies and Mr. Hider who has assisted us doing on antiangiogenic work.

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