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1094 Natural Product Communications Vol. 1 (12) 2006 Vassallo et al. Quercetin 3-methyl ether-7-O-α-Lrhamnopyranosyl-(1→6)-(2''-p-coumaroyl)-β-Dglucopyranoside (2) Yellow amorphous powder. [α] D : +18° (c 0.1, MeOH). UV/Vis λ max (MeOH) nm (log ε): 265 (3.92), 356 (4.05). 1 H NMR (600 MHz, CD 3 OD): Table 2. 13 C NMR (600 MHz, CD 3 OD): Table 2. ESIMS: m/z 769 [M - H] - . Anal. Calcd for C 37 H 38 O 18 : C, 57.66; H, 4.97. Found C, 57.68; H 5.00. Acacetin 7-O-(6''-p-coumaroyl)-β-D-glucopyranoside (3) Yellow amorphous powder. [α] D : +11° (c 0.1, MeOH). UV/Vis λ max (MeOH) nm (log ε): 269 (3.99), 321 (3.76). 1 H NMR (600 MHz, CD 3 OD): Table 2. 13 C NMR (600 MHz, CD 3 OD): Table 2. ESIMS: m/z 591 [M - H] - . Anal. Calcd for C 31 H 28 O 12 : C, 62.84; H, 4.76. Found C, 62.80; H 4.80. Acid hydrolysis of compounds 1-3: A solution of each compound (1-3, 2.0 mg each) in 1 N HCl (1 mL) was stirred at 80°C in a stoppered reaction vial for 4 h. After cooling, the solution was evaporated under a stream of N 2 . Each residue was dissolved in 1-(trimethylsilyl)imidazole and pyridine (0.2 mL), and the solution was stirred at 60°C for 5 min. After drying the solution, the residue was partitioned between water and CHCl 3 . The CHCl 3 layer was analyzed by GC using an L-CP-Chirasil-Val column (0.32 mm x 25 m). Temperatures of the injector and detector were 200°C for both. A temperature gradient system was used for the oven, starting at 100°C for 1 min and increasing up to 180°C at a rate of 5°C/min. Peaks of the hydrolysate were detected by comparison with retention times of authentic samples of L-rhamnose and D-glucose (Sigma Aldrich) after treatment with 1-(trimethylsilyl)imidazole in pyridine. Antioxidant activity in cell-free systems Quenching of DPPH: The free radical-scavenging capacity of extracts, fractions and pure compounds was tested by their ability to bleach the stable 1,1- diphenyl-2-picrylhydrazyl radical (DPPH) [16]. The reaction mixture contained 86 μM DPPH and different concentrations of the natural compounds in 1 mL of ethanol. After 10 min at room temperature the absorbance at λ = 517 nm was recorded. Trolox (50 μM), a water-soluble derivative of vitamin E, was used as a standard. Scavenger effect on superoxide anion: Superoxide anion was generated in vitro as described by Paoletti et al. [17]. The assay mixture contained in a total volume of 1 mL, 100 mM triethanolaminediethanolamine buffer, pH 7.4, 3 mM NADH, 25 mM/12.5 mM EDTA/MnCl 2 , 10 mM β-mercaptoethanol; some samples contained the natural compounds at different concentrations. After 20 min incubation at 25°C, the decrease in absorbance was measured at λ = 340 nm. Superoxide dismutase (SOD) (80 mU/mL) was used as a standard. DNA cleavage induced by hydrogen peroxide UVphotolysis: The experiments were performed, as previously reported [18], in a volume of 20 μl containing 33 μM in bp (base pair) of pBR322 plasmid DNA in 5 mM phosphate saline buffer (pH 7.4), and the natural compounds at different concentrations. Immediately prior to irradiating the samples with UV light, H 2 O 2 was added to a final concentration of 2.5 mM. The reaction volumes were held in caps of polyethylene microcentrifuge tubes, placed directly on the surface of a transilluminator (8000 μW cm -1 ) at 300 nm. The samples were irradiated for 5 min at room temperature. After irradiation 4.5 μl of a mixture, containing 0.25% bromophenol blue, 0.25% xylen cyanol FF, and 30% glycerol, were added to the irradiated solution. The samples were then analyzed by electrophoresis on a 1% agarose horizontal slab gel in Tris-borate buffer (45 mM Tris-borate, 1 mM EDTA). Untreated pBR322 plasmid was included as a control in each run of gel electrophoresis, conducted at 1.5 V/cm for 15 hours. Gel was stained in ethidium bromide (1 μg/mL; 30 min) and photographed on Polaroid- Type 667 positive land film. The intensity of each scDNA band was quantified by means of densitometry. Dimethylsulfoxide (DMSO) (1 mM) was used as a standard. Metal chelating activity: The chelating of ferrous ions by fractions and pure compounds was estimated by the ferrozine assay [19]. Briefly, natural compounds were added to a solution of 0.15 mM FeSO 4 . The reaction was initiated by the addition of 0.5 mM ferrozine and the mixture was shaken
Flavonoid glycosides from Chrozophora senegalensis Natural Product Communications Vol. 1 (12) 2006 1095 vigorously and left standing at room temperature for ten minutes. After the mixture had reached equilibrium, the absorbance of the solution was then measured spectrophotometrically at 562 nm. DTPA (5 μM) was used as a standard. Supplementary data: NMR spectral data for quercetin 3'-methyl ether-3-O-α-L-rhamno-pyranoside (4), quercetin 3'-methyl ether-3-O-α-Lrhamnopyranosyl-(1→6)-β-D-glucopyranoside (5), apigenin 7-O-(6''-p-coumaroyl)-β-D-glucopyranoside (6), quercetin 3-methyl ether-7-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (7), 4- hydroxyphenyl-O-α-L-rhamnopyranosyl-(1→6)-β-Dglucopyranoside (8), 4'''-methyl ether amenthoflavone (9), roseoside (10), icariside B5 (11), and ampelopsisionoside (12). Acknowledgments - This work was supported by the “Bioactive Compounds from Medicinal and Food Plants of Developing Countries” project of the Italian Ministry for University and Research (Ministero dell’Università e della Ricerca, MIUR). References [1] Devi RS, Narayan S, Mohan KV, Sabitha KE, Devi CS. (2003) Effect of a polyherbal formulation, Ambrex, on butylated hydroxy toluene (BHT) induced toxicity in rats. Indian Journal of Experimental Biology, 41, 1294-1299. [2] Halliwell B, Gutteridge JMC. (1999) Free radicals in biology and medicine. In: Studies of Generalized Light Emission (Luminescence/Fluorescence). 3 rd Ed. Oxford: University Press, 387-388. [3] Kerharo J, Adam JC. (1974) Pharmacopée Sénégalaise Traditionelle: Plantes Médicinales et Toxicologiques. Vigot et Frères Ed, Paris, 1011. [4] Neuwinger HD. (2000) African Traditional Medicine. A Dictionary of Plant Use and Application. Medpharm Scientific Publisher. [5] Agrawal PK. (1989) Carbon-13 NMR of Flavonoids. Elsevier Science, Amsterdam, 294-364. [6] Wolbis M. (1989) Flavonol glycosides from Sedum album. Phytochemistry, 28, 2187-2189. [7] Markham KR, Ternai B, Stanley R, Geiger H, Mabry TJ. (1978) Carbon-13 NMR studies of flavonoids. III. Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron, 34, 1389-1397. [8] Itokawa H, Suto K, Takeya K. (1981) Studies on a novel p-coumaroyl glucoside of apigenin and on other flavonoids isolated from patchouli (Labiatae). Chemical & Pharmaceutical Bulletin, 29, 254-256. [9] Nawwar MAM, El-Mousallamy AMD, Barakat, HH, Buddrus J, Linscheid M. (1989) Flavonoid lactates from leaves of Marrubium vulgare. Phytochemistry, 28, 3201-3206. [10] De Tommasi N, Pizza C, Aquino R, Cumandà J, Mahmood N. (1997) Flavonol and chalcone ester glycosides from Bidens leucantha. Journal of Natural Products, 60, 270-273. [11] Markham KR, Sheppard C, Geiger H. (1987) Carbon-13 NMR of flavonoids. Part IV. Carbon-13 NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry, 26, 3335-3337. [12] Otsuka H, Takeda Y, Yamasaki K, Takeda Y. (1992) Structural elucidation of dendranthemosides A and B: two new β-ionone glucosides from Dendranthera shiwogiku. Planta Medica, 58, 373-375. [13] Miyase T, Ueno A, Takizawa N, Kobayashi H, Oguchi H. (1988) Studies on the glycosides of Epimedium grandiflorum Morr. var. thunbergianum (Miq.) Nakai. III. Chemical & Pharmaceutical Bulletin, 36, 2475-2484. [14] Inada A, Nakamura Y, Konishi M, Murata H, Kitamura F, Toya H, Nakanishi T. (1991) A new ionone glucoside and a new phenylpropanoid rhamnoside from stems of Ampelopsis brevipedunculata (maxim.) Trautv. Chemical & Pharmaceutical Bulletin, 39, 2437-2439. [15] Di Carlo G, Mascolo N, Izzo AA, Capasso F. (1999) Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sciences, 65, 337-353. [16] Bonina F, Saija A, Tomaino A, Lo Cascio R, Rapisarda P, Dederen JC. (1998) In vitro antioxidant activity and in vivo photoprotective effect of a red orange extract. International Journal of Cosmetic Sciences, 20, 331-342. [17] Paoletti F, Aldinucci D, Mocalli A, Caparrini A. (1986) A sensitive spectrophotometric method for the determination of superoxide dismutase activity in tissue extracts. Analitycal Biochemistry, 154, 536-541. [18] Russo A, Cardile V, Lombardo L, Vanella L, Vanella A,Garbarino JA. (2005) Antioxidant activity and antiproliferative action of methanolic extract of Geum quellyon Sweet roots in human tumor cell lines. Journal of Ethnopharmacology, 100, 323-332. [19] Dinis TC, Madeira VM, Almeida LM. (1994) Action of phenolic derivates (acetoaminophen, salicylate and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavengers. Archives of Biochemistry & Biophysics, 315, 161-169.
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