CYTOTOXIC AND ANTIOXIDANT ACTIVITIES OF SECONDARY METABOLITES FROM PULICARIA UNDULATA

Objective: To evaluate the in vitro cytotoxicity, antioxidant activities and structure-activity relationship of secondary metabolites isolated from Pulicaria undulata.Methods: The methylene chloride-methanol (1:1) extract of the air-dried aerial parts of Pulicaria undulata was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of the isolated compounds were determined on the basis of the extensive spectroscopic analysis, including 1D and 2D NMR and compared with the literature data. The crude extract and the isolated compounds were evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method and cytotoxic assay using human breast cancer (MCF-7) and hepatoma (Hep G2) cell line.Results: Nine secondary metabolites were isolated from Pulicaria undulata in this study. Of which two terpenoidal compounds; 8-epi-ivalbin and 11β, 13-dihydro-4H-xanthalongin 4-O-β-D-glucopyranoside firstly isolated from the genus pulicaria and three flavonoids; eupatolitin, 6-methoxykaempferol, and patulitrin firstly isolated from P. undulata. 6-methoxykaempferol (IC50 2.3 µg/ml) showed the most potent antioxidant activity. The highest cytotoxic effect against MCF-7 and Hep G2 cells was obtained with eupatolitin (IC50 27.6 and 23.5 µg/ml) respectively. The structure-activity relationship was also examined and the findings presented here showed that 3, 5, 7, 4' and 3, 5, 4', 5'-hydroxy flavonoids were potent antioxidant and has cytotoxic activity.Conclusion: Pulicaria undulata is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as antioxidant drug and in the treatment of cancer

NEW FLAVONOIDS FROM THE AERIAL PARTS OF POLYGONUM EQUISETIFORME SM (POLYGONACEAE)

Objective: The current study was to deal the isolation and identification of secondary metabolites from Polygonum equisetiforme and evaluation of antioxidant activity of its extract.Methods: The methanol-water extract (7:3) of the air-dried aerial parts of Polygonum equisetiforme was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of these compounds were elucidated by UV and 1Dâ„2D Hâ„ C NMR spectroscopy and compared with the literature data. The crude extract was evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method.Results: Ten secondary metabolites were isolated from Polygonum equisetiforme in this study. Of which three new flavonoids named as 3,5,7,2',5' pentahydroxyflavone 3-O-b-D-glucopyranoside (1), 3,5,7,2',5' pentahydroxyflavone 3-O-b-D-glucopyranoside 8 C-sulphated (2) and quercetin 3-O-β-D-glucucorinde 6''-methyl ester 8-sulphated (3) as well as quercetin 3-O-β-D-glucucorinde methyl ester (4), quercetin 3-O-β-D-glucopyranoside (5), quercetin 7-O-β-D-glucopyranoside (6), quercetin(7), myricetin (8), P-methoxy gallic acid methyl ester (9) and gallic acid (10). The antioxidant potential of P. equisetiforme extract was evaluated by investigating it's total phenolic and flavonoid content and DPPH radical scavenging activity whereby the extract showed significant antioxidant activity (IC50 = 37.45 μg/ml). The total phenolic and flavonoid content was found to be 130.79±5.502 and 45.8±1.63 μg/ml, respectively.Conclusion: Polygonum equisetiforme is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as an antioxidant drug

Anti-Obesity Evaluation of Averrhoa carambola L. Leaves and Assessment of Its Polyphenols as Potential α-Glucosidase Inhibitors

Averrhoa carambola L. is reported for its anti-obese and anti-diabetic activities. The present study aimed to investigate its aqueous methanol leaf extract (CLL) in vivo anti-obese activity along with the isolation and identification of bioactive compounds and their in vitro α-glucosidase inhibition assessment. CLL improved all obesity complications and exhibited significant activity in an obese rat model. Fourteen compounds, including four flavone glycosides (1–4) and ten dihydrochalcone glycosides (5–12), were isolated and identified using spectroscopic techniques. New compounds identified in planta included (1) apigenin 6-C-(2-deoxy-β-D-galactopyranoside)-7-O-β-D-quinovopyranoside, (8) phloretin 3′-C-(2-O-(E)-cinnamoyl-3-O-β-D-fucopyranosyl-4-O-acetyl)-β-D-fucopyranosyl-6′-O-β-D fucopyranosyl-(1/2)-α-L arabinofuranoside, (11a) phloretin3′-C-(2-O-(E)-p-coumaroyl-3-O-β-D-fucosyl-4-O-acetyl)-β-D-fucosyl-6′-O-(2-O-β-D-fucosyl)-α-L-arabinofuranoside, (11b) phloretin3′-C-(2-O-(Z)-p-coumaroyl-3-O-β-D-fucosyl-4-O-acetyl)-β-D-fucosyl-6′-O-(2-O-β-D-fucosyl)-α-L-arabinofuranoside. Carambolaside M (5), carambolaside Ia (6), carambolaside J (7), carambolaside I (9), carambolaside P (10a), carambolaside O (10b), and carambolaside Q (12), which are reported for the first time from A. carambola L. leaves, whereas luteolin 6-C-α-L-rhamnopyranosyl-(1-2)-β-D-fucopyranoside (2), apigenin 6-C-β-D-galactopyranoside (3), and apigenin 6-C-α-L-rhamnopyranosyl-(1-2)-β-L-fucopyranoside (4) are isolated for the first time from Family. Oxalidaceae. In vitro α-glucosidase inhibitory activity revealed the potential efficacy of flavone glycosides, viz., 1, 2, 3, and 4 as antidiabetic agents. In contrast, dihydrochalcone glycosides (5–11) showed weak activity, except for compound 12, which showed relatively strong activity

Evaluation of hepatoprotective effect of Artimesia monosperma against carbon tetrachloride-induced hepatic damage rat

The hepatoprotective effect of aqueous ethanol extract of Artimesia monosperma aerial parts was investigated against carbon tetrachloride-induced acute hepatotoxicity in rat. The hepatoprotective activity of A. monosperma was evaluated by determination of liver enzyme markers in the serum (aspartat amino transferase AST; serum alanine transaminase ALT and alkaline phosphatase ALP). The histopathological studies were also carried out to support the above parameters. Oral administration of A. monosperma (100 and 200 mg/kg) markedly reduced the elevated values of AST, ALT and ALP caused by CCl 4 treatment. Glutathione (GSH) significantly decreases in the group treated with CCl 4. A. monosperma (two doses) and silymarin significantly increased GSH levels when they administrated with CCl 4. However, silymarin normalized liver enzymes and increased GSH levels than A. monosperma (two doses) when compared with the control group. Histopathological results revealed that A. monosperma treatment with its two doses exhibited almost normal architecture, compared to CCl 4-treated group. Image analysis of liver revealed a marked reduction in liver damage area after treatment with A. monosperma (100 or 200 mg/kg) and silymarin compared with CCl 4-treated group. A phytochemical study of A. monosprema resulted in the isolation of a quercetin 3-O-β- glucopyranoside; quercetin 5-O-β-glucopyranoside; isorhamnetin 3-O-β-glucopyranoside; 5, 4' - dihydroxy 6, 7-dimethoxy flavone; 5, 3' - dihydroxy 6, 7, 4'- trimethoxy flavone; 5, 7, 3' - trihydroxy 3, 6, 4' - trimethoxy flavone; quercetin and isorhamnetin. Structures of the isolated compounds were established by chromatography, UV and 1D/2D 1H/ 13C spectroscopy. Hepatoprotective effect of A. momosperma is probably due to combined effect of flavonoids

Metabolite profiles of Pulicaria crispa and P. incisa in relation to their in-vitro/ in-vivo antioxidant activity and hepatoprotective effect: A comparative mass spectrometry-based metabolomics

Plants of the genus Pulicaria (family: Asteraceae) are widely used in central Asia and the Middle East for treatment of different human diseases. Ultra performance liquid chromatography coupled to high resolution mass spectrometry (UPLC/MS) was utilized to establish the metabolic profiles of two Pulicaria species: P. crispa and P. incisa. 122 metabolites were identified including flavonoids (37), phenolic acids (22), sesquiterpenes (17), diterpenes (7), and fatty acids (27), with enrichment in methoxylated flavonoids (20), caffeoylquinic acid conjugates (14) xanthane sesquiterpenes (9) and hydroxylated fatty acids (20) in both Pulicaria species. The metabolite profile of P. incisa was characterized by the presence of tri- and tetra-methoxylated flavonoids while xanthane sesquiterpenes were the main chemical markers of P. crispa. Additionally, a novel sesquiterpene acid (dihydropulicaric acid) was annotated in both species based on its MS fragments. Antioxidant activity for P. crispa and P. incisa methanol extracts was assessed in vitro based on DPPH and ABTS assays and further in vivo using chlorpromazine intoxicated rat model. Results revealed that P. incisa extract was more effective in inhibiting both DPPH and ABTS free radicals (IC50 0.36 and 0.52 mg/mL, respectively) than P. crispa (IC50 0.51 and 0.73 mg/mL). In the animal model, antioxidant activity of P. incisa (20 mg/kg/day) was also slightly higher causing a 55 % reduction in MDA levels and 65 % increase in GSH activity compared to untreated animals. Furthermore, both extracts showed a hepatoprotective effect as revealed by improvement in levels of serum biomarkers of liver functions: total bilirubin, alanine transaminase (ALT) and aspartate transaminase (AST) comparable to silymarin at 25 mg/kg/day. These findings were also supported by the preserved integrity of the hepatic tissues of animals receiving either extracts at a dose of 20 mg/kg b.wt. The present study reveals for the potential antioxidant and hepatoprotective effects for Pulicaria in relation to its bioactive metabolites

Anthraquinone glycosides from Cassia roxburghii and evaluation of its free radical scavenging activity

The methanolic extract of the leaves of Cassia roxburghii DC., was investigated for its anthraquinone glycosides and antioxidant activity. Two new anthraquinone glycosides named emodin 1-O-β-d-glucopyranosyl-(1→2)- glucopyranoside (1) and aloemodin 8-O-β-d-glucopyranosyl-(1→6)- glucopyranoside (2) along with aloemodin 8-O-β-d-glucopyranoside (3), emodin (4), aloemodin (5) and one flavonoid, quercetin-3-O-α-l- rhamnopyranoside, were isolated from the leaves of C. roxburghii. Structures of the isolated compounds were established by UV, HRESI-MS, and 1D/2D 1H/ 13C NMR spectroscopy. The total extract and some isolated compounds were determined against DPPH (2,2-diphenyl-1-(2,4,6- trinitrophenyl)hydrazinyl radical, for their free radical scavenging activity, the total alcoholic extract showed strong antioxidant activity while the two new compounds showed weak antioxidant activity.Peer Reviewe

Phytochemical, anti-inflammatory, anti-ulcerogenic and hypoglycemic activities of Periploca angustifolia L extracts in rats

Abstract Background In traditional North Africa, medicine decoctions of the leaves of Periploca angustifolia are used to treat diarrhea, inflammation, ulcers, edema and diabetes. The aim of the study was to evaluate the phytochemical, anti-inflammatory, anti-ulcerogenic, and hypoglycemic activities of an ethanolic extract of P. angustifolia L. in rats. Methods An extract of air-dried powdered P. angustifolia plant was obtained using 96% ethanol. The extract was concentrated and the total phenolic and flavonoids contents were estimated colorimetrically. The phenolic and flavonoid compounds were quantified and identified using high performance liquid chromatography (HPLC). The anti-inflammatory, anti-ulcerogenic and hypoglycemic activities of the extract were evaluated in three rat models respectively: formaldehyde-induced paw edema, ethanol induced gastric damage and alloxan induced hyperglycemia. Results The total flavonoids and total phenolics constituted 15% and 2.69% of the extract, respectively and are expressed as quercetin equivalent and μg/mg gallic acid equivalent (GAE). Coumarin, resorcinol, isorhamnetin, quercetin, and naphthalene were isolated from the ethanolic extract of P. angustifolia. Oral administration of the ethanolic extract at 500 mg/kg body weight (b.wt.) significantly reduced paw inflammation, gastric lesions, ulcer index scores and blood glucose levels in normal and diabetic rats. Conclusion The crude ethanolic extract of P. angustifolia exhibited promising anti-inflammatory, anti-ulcerogenic, and hypoglycemic activities in accordance with the plant’s uses in folk medicine suggesting that P. angustifolia may be a safe alternative to chemical drugs

Phenolic metabolites, biological activities, and isolated compounds of Terminalia muelleri extract

© 2017 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.[Context]: Terminalia muelleri Benth. (Combretaceae), is rich with phenolics that have antioxidant and cytotoxic activities. No screening studies were published before on T. muelleri.[Objective]: The study focused on isolation and identification of secondary metabolites from aqueous methanol leaf extract of T. muelleri and evaluation of its biological activities.[Materials and methods]: The n-butanol extract was chromatographed on polyamide 6, and eluted with H2O/MeOH mixtures of decreasing polarity, then separated by different chromatographic tools that yielded 10 phenolic compounds. The antioxidant activity of the extract was evaluated by investigating its total phenolic and flavonoid content and DPPH scavenging effectiveness. The extract and the two acylated flavones were evaluated for their anticancer activity towards MCF-7 and PC3 cancer cell lines. Molecular docking study of the acylated flavones was performed against topoisomerase enzyme.[Results and discussion]: Two acylated flavonoids, apigenin-8-C-(2″-O-galloyl) glucoside 1 and luteolin-8-C-(2″-O-galloyl) glucoside 2, were isolated and identified for the second time in nature, with eight tannins (3–10), from the leaves of T. muelleri. The extract and compound 10 showed the most significant antioxidant activity (IC50 = 3.55 and 6.34 μg/mL), respectively. The total extract and compound 2 demonstrated cytotoxic effect against MCF-7 with IC50 = 29.7 and 45.2 μg/mL respectively, while compound 1 showed cytotoxic effect against PC3 (IC50 = 40.8 μg/mL). The docking study of compounds 1 and 2 confirmed unique binding mode in the active site of human DNA topoisomerase enzyme.[Conclusions]: Terminalia muelleri is a promising medicinal plant as it possesses high antioxidant activity and moderate cytotoxic activity against MCF-7.Peer Reviewe