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Chemical Constituents, Antimicrobial, Analgesic, Antipyretic, and Anti-Inflammatory Activities of Euphorbia Peplus L

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Chemical Constituents, Antimicrobial, Analgesic, Antipyretic, and Anti-Inflammatory Activities of Euphorbia Peplus L Phytopharmacology 2013, 4(1), 69-80 Ali et al. Chemical constituents, antimicrobial, analgesic, antipyretic, and anti-inflammatory activities of Euphorbia peplus L. Ahamed A. Ali, Hanaa M. Sayed, Sabrin R.M. Ibrahim*, Ahamed M. Zaher Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt, *Corresponding author: [email protected]; Tel: +2-0882141330; Fax: +2-088-2332776 Received: 9 August 2012, Revised: 28 September 2012, Accepted: 29 September 2012 Abstract Fifteen compounds were isolated from Euphorbia peplus L.. Their structures were established by physical, chemical, and spectral data (UV, IR, MS, and 1D NMR), as well as comparison with authentic samples. The preliminary phytochemical scr- eening of the alcoholic extract was done. GC-MS study of the fatty acid methyl es- ters of the n-hexane fraction was carried out. The antimicrobial, pharmacological, and cytotoxic activities of the different extracts were evaluated. The anti-inflamm- atory activity was evaluated by using yeast-induced paw edema method at doses of 200 and 400 mg/kg of the extracts. The MeOH and EtOAc extracts give potent anti-inflammatory activity compared with indomethacin. All the extracts exhibited significant analgesic activity in the acetic acid-induced writhing method at dose 400 mg/kg. The tested extracts showed antipyretic activity at doses 200 and 400 mg/kg for each extract. They control the hyperthermia for 4 hr without decrease in activity. Keywords: Euphorbia peplus, Euphorbiaceae, GC-MS, antimicrobial, Introduction Family Euphorbiaceae comprises over 7500 species within 283 genera (Boulos, 1980; Tackholm, 1974). The genus Euphorbia consists of more than 1600 species growing in near- ly all types of climates throughout the world (Boulos, 1980). The wide spread plants of the genus Euphorbia are rich source of sterols, flavonoids, diterpenoids, and triterpenes with diverse structures (Jassbi, 2006; Ferreira et al, 1993; Gotta et al, 1984; Ivanovaa et al, 2003; Rizk et al, 1980). Euphorbia peplus L. is originally native to Europe and North Africa (Zhi- Qin et al, 2010). Its milky sap has long been used as a remedy for the treatment of skin canc- ers especially non-melanoma skin cancer (NMSC) and the active compounds have been determined to be diterpene esters (Ramsay et al, 2011). These esters were cytotoxic against a variety of cancers both in vivo and in vitro and are the subject of ongoing research around the world. Previous phytochemical studies of E. peplus led to the isolation of diterpenes (Zhi-Qin et al, 2010; Homanna et al, 1999; Jakopovic et al, 1998; Mucsi et al, 2001), flavonoids (Jas- 69 © 2013 Inforesights Publishing UK Phytopharmacology 2013, 4(1), 69-80 Ali et al. sbi, 2006; Dumkow et al, 1973; Mayumi et al, 1975; Nazemiyeh et al, 2010), sterols (Jassbi, 2006; Ferreira et al, 1993; Giner et al, 2000), triterpene alcohols (Cateni et al, 2000), and cer- ebrosides (Cateni et al, 2010). In this work we reported the phytochemical screening, isolate- ion and structural elucidation of fifteen compounds; eight of them (1, 4, 5, 7, 10, and 13-15) were reported for the first time from the plant and one (6) for the first time from the family. Also, GC analysis of the fatty acid methyl esters of the n-hexane fraction, in addition to anti- microbial, cytotoxic, and pharmacological activities of the different extracts were carried out. Materials and methods General experimental procedures Melting points were carried out on an Electrothermal 9100 Digital Melting Point apparatus (Electrothermal Engineering Ltd, Essex, England). EIMS was recorded on a Jeol the mass route JMS.600H mass spectrometer. UV spectra were recorded on a Shimadzu 1601 UV/VIS spectrophotometer in MeOH and after addition of different shift reagents. The IR spectra were measured on a Shimadzu Infrared-400 spectrophotometer (Kyoto, Japan). NMR spectra (chemical shifts in ppm, coupling constants in Hz) were recorded on Jeol Oxford NMR YH-400 and 500 using CDCl3 and DMSO-d6 as solvents. NMR spectra were refere- 1 13 nced to the solvent signals (CDCl3: 7.26 ppm for H and 77.0 ppm for C; DMSO-d6: 2.49 ppm for 1H and 39.9 ppm for 13C). Column chromatographic separation was performed on silica gel 60 (0.04-0.063 mm, Merck) and Sephadex LH-20 (0.25-0.1 mm, Merck). TLC was performed on pre-coated TLC plates with silica gel 60 F254 (0.2 mm, Merck). The chroma- tograms were developed using the following solvent systems: n-hexane:EtOAc (95:5, S1), n- hexane:EtOAc (90:10, S2), CHCl3:MeOH (95:5, S3), CHCl3:MeOH (90:10, S4), CHCl3: MeOH (80:20, S5), and n-BuOH:HOAc:H2O (4:1:2, S6). Spots were detected by spraying with the following spray reagents: I-1 % AlCl3 for flavonoids, II-FeCl3 for phenolic compou- nds, III-p- anisaldehyde/H2SO4 for triterpenoids (Mohammad et al, 2010). Plant material The plant material used in this work was the whole plant of Euphorbia peplus L. The plant was collected during the flowering stage in the period of April to June 2006 from Assuit University campus. The plant was kindly identified by Prof. Dr. A. A. Fayed, Profess- or of Plant Taxonomy, Botany Department, Faculty of Science, Assiut University. A voucher sample (EP-20061) was kept in the herbarium of the Faculty of Pharmacy, Assiut University, Assiut, Egypt. Phytochemical screening The alcoholic extract of Euphorbia peplus L. was subjected to phytochemical tests to detect the various types of chemical constituents present using standard procedures (Rakesh et al., 2010). GC-MS analysis 5 g of the n-hexane fraction refluxed with 0.5 N alc. KOH for 3 hr on a boiling water bath. The alcohol was distilled off and the aqueous liquid was diluted with distilled water 70 © 2013 Inforesights Publishing UK Phytopharmacology 2013, 4(1), 69-80 Ali et al. then extracted with ether till exhaustion to give unsaponifiable matter: The aqueous solution (soap) that remained after removal of the unsaponifiable matter was treated in the same way as previously mentioned to afford the fatty acids methyl esters (Assaf et al, 2010). GC-MS analysis of the fatty acids methyl esters was performed using Agilent GC-MS spectrometer (USA). The software controller/integrator was Turbo Mass, version 4.5.0.007 (PerkinElmer). GC-MS capillary column (3% methyl phenyl silicon type of stationary phase (OV-17) on 80/100, Carbowax HP (CWHP), 6' x 1/8" x 0.085", S.S.) was used. The carrier gas was heliu- m (purity 99.9999%) at a flow rate of 2 mL/min (32 p.s.i., flow initial 55.8 cm/s, split; 1:40). The column temperature program was: 160 °C for 2 min then increase by rate 15 °C/min till 300 °C and isothermal for 15 min. The injector temperature was 250 °C. Detector tempera- ture is 320 °C with dual flame ionization detector. MS scan was from 50 to 650 m/z. Extraction and isolation The air-dried powdered plant (2.7 kg) was extracted with MeOH. The MeOH extract was concentrated under reduced pressure to get a viscous brown residue (110 g). This residue was suspended in 500 mL distilled water and subjected to solvent fractionation using n-hexa- ne, CHCl3, EtOAc, and n-BuOH which were separately concentrated to yield 20, 12, 17, and 12 g, respectively. Chromatographic investigation of the n-hexane fraction The n-hexane fraction (20 g) was subjected to silica gel column (800 g, 130 x 5 cm) using n-hexane:EtOAc gradient. Four subfractions were obtained HFI to HFIV. HF-II (4 g, n-hexane:EtOAc 95:5) was chromatographed over silica gel column using n-hexane:EtOAc gradient elution to afford compounds 1 (50 mg, colorless fine needles) and 2 (50 mg, white crystals). HF-IV (4.4 g, n-hexane:EtOAc 85:15) was subjected to silica gel column chromat- ography (120 g, 50 x 5 cm) eluted with n-hexane:EtOAc gradient, where compounds 3 (90 mg, white crystalline needles) and 4 (50 mg, white crystalline needles) were isolated. Chromatographic investigation of the CHCl3 fraction The CHCl3 fraction (12 g) was chromatographed over silica gel column (500 g, 100 x 5 cm) using CHCl3:MeOH gradient elution. Three subfractions were obtained CF-I to CF-III. Silica gel column chromatography (150 g, 50 x 3 cm) of CF-II (4 g, CHCl3:MeOH 95:5) using CHCl3:MeOH gradient gave 5 (70 mg, colorless crystal), 6 (25 mg, white granular powder), and 7 (30 mg, yellowish white crystals). CF-III (2.5 g CHCl3:MeOH 9:1) was subj- ected to silica gel column chromatography (100 g, 50 x 3 cm) eluted with CHCl3:MeOH gra- dient elution to afford compounds 8 (25 mg, yellow amorphous powder), 9 (20 mg, yellow amorphous powder), and 10 (20 mg, colorless needles). Chromatographic investigation of the EtOAc fraction EtOAc fraction (17 g) was subjected to silica gel column chromatography (600 g, 100 x 5 cm) eluted with CHCl3:MeOH gradient to give four subfractions EF-I to EF-IV. These sub-fractions were further chromatographed over silica gel column, eluted with CHCl3: 71 © 2013 Inforesights Publishing UK Phytopharmacology 2013, 4(1), 69-80 Ali et al. MeOH to afford compounds 11 (50 mg, yellow amorphous powder), 12 (70 mg, yellow amo- rphous powder), and 13 (30 mg, yellow amorphous powder). Chromatographic investigation of the n-BuOH fraction Silica gel column chromatography (500 g, 100 x 5 cm) of n-BuOH fraction (12 g) usi- ng CHCl3:MeOH gradient afforded two subfractions. They were further chromatographed over silica gel column, eluted with CHCl3:MeOH gradient to give compounds 14 (20 mg, ye- llow amorphous powder) and 15 (40 mg, yellow amorphous powder).
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