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Öğe Analysis of saponins and phenolic compounds as inhibitors of alpha-carbonic anhydrase isoenzymes(Taylor & Francis Ltd, 2013) Koz, Omer; Ekinci, Deniz; Perrone, Angela; Piacente, Sonia; Alankus-Caliskan, Ozgen; Bedir, Erdal; Supuran, Claudiu T.A series of phenolic and saponin type natural products such as quercetin, rutin, catechin, epicatechin, silymarin, trojanoside H, astragaloside IV, astragaloside VIII and astrasieversianin X, were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). We here report inhibitory effects of these compounds against five alpha-CA isozymes (hCA I, hCA II, bCA III, hCA IV and hCA VI). Most of the phenolic and saponin type compounds inhibited the isoenzymes quite effectively at low micromolar K-i-s ranging between 0.1 and 4 mu M, whereas a few derivatives were ineffective (K-i-s > 100 mu M). The results were remarkable which might lead to design of novel CAIs with a diverse inhibition mechanism compared to sulfonamide/sulfamate inhibitors.Öğe Cycloartane glycosides from Astragalus aureus(Pergamon-Elsevier Science Ltd, 2011) Gulcemal, Derya; Alankus-Caliskan, Ozgen; Perrone, Angela; Ozgokce, Fevzi; Piacente, Sonia; Bedir, ErdalEight cycloartane-type triterpene glycosides (1-8) were isolated from Astragalus aureus Willd along with ten known cycloartane-type glycosides (9-18). Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analyses. Compounds 1-5 are cyclocanthogenin glycosides, whereas compounds 6-8 are based on cyclocephalogenin as aglycon, more unusual in the plant kingdom, so far reported only from Astragalus spp. Moreover, for the first time monoglycosides of cyclocanthogenin (5) and cyclocephalogenin (7, 8) are reported. All of the compounds tested for their cytotoxic activities against a number of cancer cell lines. Among the compounds, only 8 exhibited activity versus human breast cancer (MCF7) at 45 mu M concentration. (C) 2011 Elsevier Ltd. All rights reserved.Öğe Cycloartane Glycosides from Astragalus erinaceus(Acg Publications, 2012) Savran, Tahir; Gulcemal, Derya; Masullo, Milena; Karayildirim, Tamer; Polat, Emre; Piacente, Sonia; Alankus-Caliskan, OzgenOne new cycloartane-type saponin, 3-O-[beta-D-xylopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-6-O-beta-D-glucuronopyranosyl-3 beta,6 alpha,16 beta,24(S),25-pentahydroxyxyxloartane (1) was isolated from the MeOH extract of whole plant parts of Astragalus erinaceus along with 5 known saponins (2-6), cyclodissectoside, cycloastragenol, 6-O-beta-D-glucopyranosyl-3 beta,6 alpha,16 beta,24(S),25-pentahydroxycycloartane, oleifolioside B and 3,6-di-O-beta-D-xylopyranosyl-3 alpha,6 beta,16 beta,24(S),25-pentahydroxycycloartane, respectively. Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The glucuronic acid moiety in cycloartanes is a very unusual finding.Öğe Cycloartane glycosides from Astragalus plumosus var. krugianus and evaluation of their antioxidant potential(Elsevier Science Bv, 2014) Denizli, Nilufer; Horo, Ibrahim; Gulcemal, Derya; Masullo, Milena; Festa, Michela; Capasso, Anna; Koz, Omer; Piacente, Sonia; Alankus-Caliskan, OzgenThe methanol extracts of Astragalus plumosus var. krugianus Chamb. & Matthews afforded sixteen cycloartane glycosides among which krugianoside A, was never reported before. All compounds were evaluated for their cytotoxic activity in human skin fibroblast WS1 cells. For compounds exhibiting no significant effect on WS1 viability, the antioxidant potential was examined. Compounds 1 and 8 prevented elevation of ROS induced by t-BOOH, suggesting the potential activity of these compounds to protect fibroblasts from oxidative stress. (C) 2013 Elsevier B.V. All rights reserved.Öğe Cycloartane Glycosides from Three Species of Astragalus (Fabaceae)(Wiley-V C H Verlag Gmbh, 2011) Linnek, Jens; Mitaine-Offer, Anne-Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Paululat, Thomas; Avunduk, Sibel; Alankus-Caliskan, Ozgen; Lacaille-Dubois, Marie-AlethNine cycloartane-type glycosides were isolated from three species of the genus Astragalus (Fabaceae): From the aerial parts of A. cicer L., two new saponins, cicerosides A and B (1 and 2, resp.), i.e., a tetradesmosidic and tridesmosidic cycloartane-type glycosides besides one known compound, from the roots of A. sempervirens Lam., one known saponin, and from the roots of A. ptilodes Boiss. var. cariensis Boiss., five known compounds. Their structures were established mainly by 600-MHz 2D-NMR techniques (H-1, H-1-COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectroscopy.Öğe New triterpene saponins from Phryna ortegioides(Elsevier Science Bv, 2015) Horo, Ibrahim; Masullo, Milena; Falco, Antonia; Senol, Serdar Gokhan; Piacente, Sonia; Alankus-Caliskan, OzgenFour new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae. The structures of the new compounds were determined as gypsogenic acid 28-O-beta-D-glucopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 6)-O-beta-D-glucopyranosyl ester (1), 3-O-alpha-L-arabinofuranosyl-gypsogenic acid 28-O-beta-D-glucopyranosyl-(1 -> 3)-O-[beta-D-glucopyranosyl-(1 -> 6)]-O-beta-D-glucopyranosyl ester (2), 3-O-alpha-L-arabinofuranosyl-gypsogenic acid 28-O-beta-D-glucopyranosyl-(1 -> 3)-O-[beta-D-glucopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 6)-O-]-beta-D-glucopyranosyl ester (3), 3-O-alpha-L-arabinofuranosyl-16 alpha-hydroxyolean-12-en-23,28-dioic acid-28-O-beta-D-glucopyranosyl-(1 -> 3)-O-[beta-D-glucopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 6)]-O-beta-D-glucopyranosyl ester (4). Their structures were established by a combination of one-and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family. The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC50 values of 77 and 52 mu M, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 mu M, caused a significant reduction of the cell number. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.Öğe Oleanane glycosides from Astragalus tauricolus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling(Pergamon-Elsevier Science Ltd, 2013) Gulcemal, Derya; Masullo, Milena; Napolitano, Assunta; Karayildirim, Tamer; Bedir, Erdal; Alankus-Caliskan, Ozgen; Piacente, SoniaAs a part of our ongoing research for bioactive compounds from Turkish Astragalus species, the investigation of Astragalus tauricolus has been carried out. An approach based on HPLC-ESIMSn experiments has been used to profile the triterpene glycosides occurring in the butanol extract of the whole plant. On the basis of the results of the online screening by HPLC-ESIMSn, 22 oleanane-type triterpene glycosides, including ten compounds never reported before, were isolated, and their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Noteworthy, cycloartane-type triterpene glycosides, the main constituents of Astragalus spp., were not found. This peculiar feature characterizes a very limited group of Astragalus spp. The antiproliferative activity of the isolated compounds 1-12, 15, 17-19 was evaluated against a small panel of cancer cell lines. Only compound 11 showed an IC50 of 22 mu M against human leukemia cell line (U937). The other tested compounds, in a range of concentrations between 1 and 50 mu M, did not cause any significant reduction of the cell number. (C) 2012 Elsevier Ltd. All rights reserved.Öğe Oleanane glycosides from Astragalus tauricolus: Isolation and structural elucidation based on a preliminary liquid chromatography-electrospray ionization tandem mass spectrometry profiling(Pergamon-Elsevier Science Ltd, 2013) Gulcemal, Derya; Masullo, Milena; Napolitano, Assunta; Karayildirim, Tamer; Bedir, Erdal; Alankus-Caliskan, Ozgen; Piacente, SoniaAs a part of our ongoing research for bioactive compounds from Turkish Astragalus species, the investigation of Astragalus tauricolus has been carried out. An approach based on HPLC-ESIMSn experiments has been used to profile the triterpene glycosides occurring in the butanol extract of the whole plant. On the basis of the results of the online screening by HPLC-ESIMSn, 22 oleanane-type triterpene glycosides, including ten compounds never reported before, were isolated, and their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Noteworthy, cycloartane-type triterpene glycosides, the main constituents of Astragalus spp., were not found. This peculiar feature characterizes a very limited group of Astragalus spp. The antiproliferative activity of the isolated compounds 1-12, 15, 17-19 was evaluated against a small panel of cancer cell lines. Only compound 11 showed an IC50 of 22 mu M against human leukemia cell line (U937). The other tested compounds, in a range of concentrations between 1 and 50 mu M, did not cause any significant reduction of the cell number. (C) 2012 Elsevier Ltd. All rights reserved.Öğe Oleanane type glycosides from Paronychia anatolica subsp balansae(Elsevier Science Bv, 2014) Gulcemal, Derya; Masullo, Milena; Alankus-Caliskan, Ozgen; Piacente, SoniaFour new oleanane-type triterpene glycosides were isolated from the methanol extract of the roots of Paronychia anatolica subsp. balansae along with three known oleanane-type triterpene glycosides. Structures of the new compounds were established as 3-O-beta-D-glucuronopyranosyl-28-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-quinovopyranoside] zahnic acid, 3-O-beta-D-glucuronopyranosyl-28-O-[beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-quinovopyranoside] zahnic acid, 3-O-beta-D-glucuronopyranosyl-28-O-[alpha-L-arabinofuranosyl(1 -> 2)-beta-D-quinovopyranoside] zahnic acid, 28-O-beta-D-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl]-medicagenic acid, by using 1D and 2D-NMR techniques and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including human breast cancer (MCF-7), human lung adenocarcinoma (A549) and human leukemia (U937) cell lines. (C) 2013 Elsevier B.V. All rights reserved.Öğe Phenolic Glycosides with antiproteasomal activity from Centaurea urvillei DC. subsp urvillei(Elsevier Sci Ltd, 2010) Gulcemal, Derya; Alankus-Caliskan, Ozgen; Karaalp, Canan; Ors, Ahmet Uygar; Ballar, Petek; Bedird, ErdalA new flavanone glycoside, naringenin-7-O-beta-D-glucuronopyranoside, and a new flavonol glycoside, 6-hydroxykaempferol-7-O-beta-D-glucuronopyranoside were isolated together with 12 known compounds, 5 flavone glycoside; hispidulin-7-O-beta-D-glucuronopyranoside, apigenin-7-O-beta-D-methylglucuronopyranoside, hispidulin-7-O-beta-D-methylglucuronopyranoside, hispidulin-7-O-beta-D-glucopyranoside, apigenin-7-O-beta-D-glucopyranoside, a flavonol; kaempferol, two flavone; apigenin, and luteolin, a flavanone glycoside; eriodictyol-7-O-beta-D-glucuronopyranoside, and three phenol glycoside; arbutin, salidroside, and 3,5-dihydroxyphenethyl alcohol-3-O-beta-D-glucopyranoside from Centaurea urvillei subsp. urvillei. The structure elucidation of the new compounds was achieved by a combination of one- (H-1 and C-13) and two-dimensional NMR techniques (G-COSY, G-HMQC, and G-HMBC) and LC-ESI-MS. The isolated compounds were tested for their antiproteasomal activity. The results indicated that kaempferol, a well known and widely distributed flavonoid in the plant kingdom, was the most active antiproteasomal agent, followed by apigenin, eriodictyol-7-O-beta-D-glucuronopyranoside, 3,5-dihydroxyphenethyl alcohol-3-O-beta-D-glucopyranoside, and salidroside, respectively. (C) 2010 Elsevier Ltd. All rights reserved.Öğe The Potential Hepatoprotective and Antioxidant Activities of Astragalus davisii against Paracetamol Induced Liver Damage in Rats(Sciencedomain Int, 2020) Foudah, Ahmed, I; Alqarni, Mohammed H.; Soliman, Gamal A.; Abdel-Rahman, Rehab F.; Alankus-Caliskan, Ozgen; Ganaie, Majid A.; Yusufoglu, HasanThe current study aimed to estimate in vitro antioxidant effect of Astragalus davisii (A. davisii) extract. Further, the possible protective effect of A. davisii against paracetamol (PCM)-induced liver injury was assessed in rats. A. davisii was tested for its antioxidant activity using DPPH radical scavenging assay. the hepatoprotective potential of the extract was assessed in rats following oral administration for 7 days. Liver injury was induced in rats following oral administration of PCM overdose. Hepatic biomarkers; alanine-aminotransferase, aspartate-aminotransferase, alkaline-phosphatase, gamma-glutamyl transferase and bilirubin were increased, while total protein and albumin were reduced in PCM control animals. Additionally, the activities of superoxide dismutase (SOD), catalase and glutathione-peroxidase (GPx) and the levels of glutathione were significantly declined, while levels of hepatic malondialdehyde (MDA) were significantly elevated in PCM alone treated rats. Oral administration of A. davisii (400 mg/kg) prior to PCM inhibited the elevation in the levels of liver damage markers in serum and protected against oxidative stress. Histopathological remarks confirmed the hepatoprotective potential of the extract. the results suggest that A. davisii extract at 400 mg/kg protects liver against injury induced by PCM overdose.Öğe Protective effects of two Astragalus species on ulcerative colitis in rats(Pharmacotherapy Group, 2016) Soliman, Gamal A.; Gabr, Gamal A.; Al-Saikhan, Fahad I.; Ansari, Mohd Nazam; Khan, Tajdar H.; Ganaie, Majid A.; Abdulaziz, Saeedan S.; Alankus-Caliskan, OzgenPurpose: To investigate the anti-inflammatory activities of root extracts of Astragalus gummifera and Astragalus kurdicus, as well as their protective effects against acetic acid-induced ulcerative colitis (UC) in rats. Methods: The roots of both species were shade-dried, pulverized to fine powder and extracted with 80 % ethanol. The extracts were lyophilized using freeze-dryer, and their anti-inflammatory effects were evaluated in rats by carrageenan-induced paw edema. In UC study, the extracts, at doses of 200 and 400 mg/kg, were given orally to rats for 5 days, with the last dose given 2 h prior to colitis induction. Histopathological studies were carried out on the colon tissues. Dexamethasone (DEX) was used as standard anti-inflammatory drug. Results: A. gummifera (400 mg/kg) and A. kurdicus (200 and 400 mg/kg) significantly reduced carrageenan-induced edema, offered protection against UC and arrested UC-induced increases in myeloperoxidase (MPO) activity. Histological examination of colon sections also revealed evidence of extract-induced protection from UC. Conclusion: These results suggest that A. gummifera and A. kurdicus root extracts have promising potential as sources of anti-inflammatory agents which may be useful in the treatment of UC.Öğe Saponins from Astragalus hareftae (NAB.) SIRJ(Pergamon-Elsevier Science Ltd, 2012) Horo, Ibrahim; Bedir, Erdal; Masullo, Milena; Piacente, Sonia; Ozgokce, Fevzi; Alankus-Caliskan, OzgenFour cycloartane- (hareftosides A-D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-beta-D-xylopyranosyl-3 beta,6 alpha, 16 beta,24(S),25-pentahydroxycycloartane (1), 3,6,24-tri-O-beta-D-xylopyranosyl-3 beta,6 alpha,16 beta,24(S),25-pentahydroxycycloartane (2), 3-O-beta-D-xylopyranosyl-3 beta,6 alpha,16 beta,25-tetrahydroxy-20(R),25(S)-epoxycycloartane (3), 16-O-beta-D-glucopyranosyl-3 beta,6 alpha,16 beta,25-tetrahydroxy-20(R), 24(S)-epoxycycloartane (4), 3-O-[beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 2)-O-beta-D-glucuronopyranosyl]-soyasapogenol B (5) by the extensive use of 1D- and 2D-NMR experiments along with ESI-MS and HR-MS analyses. (c) 2012 Elsevier Ltd. All rights reserved.Öğe Saponins from Cephalaria aristata C. Koch(Acg Publications, 2014) Gulcemal, Derya; Masullo, Milena; Senol, Serdar Gokhan; Alankus-Caliskan, Ozgen; Piacente, SoniaOne new oleanane-type saponin, 3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 3)-alpha-D-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosylhederagenin 28-O-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester (1) was isolated from the MeOH extract of whole plant parts of Cephalaria aristata C. Koch along with three known oleanane-type saponins, 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl hederagenin 28-O-(beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl) ester (2), 3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosyl hederagenin (3) and 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosylhederagenin (4). Also three triterpenoids and a steroid glucoside oleanolic acid (5), beta-amyrin (6), 20-beta-hydroxyursolic acid (7) and 29-hydroxystigmast-5-en-3-O-beta-D-glucopyranoside (8). Their structures were established by the extensive use of 1D-and 2D-NMR experiments along with ESIMS and HRMS analysis.Öğe Secondary Metabolites from Astragalus lycius and Their Cytotoxic Activities(Natural Products Inc, 2016) Horo, Ibrahim; Kocabas, Fatma; Alankus-Caliskan, Ozgen; Ozgokce, Fevzi; Khan, Ihlas A.; Bedir, ErdalEight known secondary metabolites were isolated from the methanolic extract of the whole plant of Astragalus lycius Boiss. They were identified as 5,5'-dihydroxy-3'-methoxy-isoflavone-7-O-beta-D-glucoside (1), genistin (2), sissotrin (3), 5,4'-dimethoxy-isoflavone-7-O-beta-D-glucopyranoside (4), (7S,8R)-5-methoxydehydrodiconiferyl alcohol-4-O-beta-D-glucopyranoside (5), 4-O-lariciresinol-glucoside (6), 2-phenylethyl-beta-D-glucopyranoside (7) and beta-isitosterol-3-O-beta-D-glucopyranoside (8) by spectroscopic methods including H-1- and C-13-NMR and HR-MS experiments, and by comparison with literature values. Compounds 1-7 are reported for the first time from Astragalus taxa. All of the compounds were tested for their cytotoxic activities against a number of cancer cell lines. Among them, only 6 exhibited significant activity against human colon carcinoma (HT-29) at 2.69 mu M concentration.Öğe Secondary Metabolites from the Roots of Paronychia chionaea(Natural Products Inc, 2011) Avunduk, Sibel; Alankus-Caliskan, Ozgen; Miyamoto, Tomofumi; Tanaka, Chiaki; Lacaille-Dubois, Marie-AlethTwo novel secondary metabolites, compounds (1-2) were isolated from the roots of Paronychia chionaea. On the basis of spectroscopic data including ID and 2D NMR experiments (COSY, TOCSY, HSQC, and HMBC), and mass spectroscopy, their structures were established as 6-C[alpha-L-arabinopyranosyl-(1 -> 2)-beta-D-glucopyranosyl]-7-O-[beta-D-glucopyranosyl]-luteolin 3'-methyl ether (1), and 2-(methoxy)-2-(3,5-dimethoxy 4-hydroxyphenyl)-ethane-1,2-diol 1-O-beta-D-glucopyranoside (2).Öğe Synthesis, antimicrobial and cytotoxic activities, and structure-activity relationships of gypsogenin derivatives against human cancer cells(Elsevier France-Editions Scientifiques Medicales Elsevier, 2014) Emirdag-Ozturk, Safiye; Karayildirim, Tamer; Capaci-Karagoez, Aysun; Alankus-Caliskan, Ozgen; Ozmen, Ali; Poyrazoglu-Coban, EsinA series of gypsogenin (1) derivatives (1a-i) was synthesized in good yields, and the derivatives' structures were established using UV, IR, H-1 NMR,C-13 NMR, and LCMS spectroscopic data. Among the tested compounds, 1a, 1b, 1d, 1e, and gypsogenin (1) showed antimicrobial activities against Bacillus subtilis and Bacillus thrungiensis, with inhibition zones of 10-14 mm. In addition, compounds 1b, 1d, and 1e showed antimicrobial activities against Bacillus cereus, with inhibition zones of 9-14 mm. Using six human cancer cell lines in vitro, the cytotoxic activities of all tested compounds were determined by calculating the IC50 values. Doxorubicin and paclitaxel were used as controls. Among the tested compounds, 1a, 1c, and 1d had inhibitory effects with IC50 values of 3.9 mu M (HL-60 cells), 5.15 mu M (MCF-7 cells), and 5.978 mu M (HL-60), respectively. To determine the type of cell death, Hoechst 33258 (HO) and propidium iodide (PI) double staining was used. Especially, gypsogenin (1) and compound la triggered the apoptotic mechanism at a concentration of 20 mu M. Thus, gypsogenin (1) and compounds la, 1c, and 1d possess varying degrees of biological activities and can be considered as potential antitumor agents. (C) 2014 Elsevier Masson SAS. All rights reserved.Öğe Triterpene glycosides from Agrostemma gracilis(Pergamon-Elsevier Science Ltd, 2010) Koz, Omer; Bedir, Erdal; Masullo, Milena; Alankus-Caliskan, Ozgen; Piacente, SoniaFour triterpene saponins, agrostemmosides A-D were isolated from the methanol extract of Agrostemma gracilis. The structures of the compounds were determined as 3-O-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1 -> 2)-[beta-D-xylopyranosyl-(1 -> 6)]-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyloleanolic acid 28-O-beta-D-glucopyranosyl-(1 -> 2)-[beta-D-xylopyranosyl-(1 -> 6)]-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1 -> 2)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester, 3-O-beta-D-xylopyranosylechinocystic acid 28-O-beta-D-glucopyranosyl-(1 -> 2)-[beta-D-xylopyranosyl-(1 -> 6)]-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. To the best of our knowledge this is the first phytochemical report on A. gracilis, and echinocystic acid saponins were encountered for the first time in Caryophyllaceae family. (C) 2009 Elsevier Ltd. All rights reserved.Öğe Triterpene saponins from Cyclamen hederifolium(Pergamon-Elsevier Science Ltd, 2012) Altunkeyik, Hilal; Gulcemal, Derya; Masullo, Milena; Alankus-Caliskan, Ozgen; Piacente, Sonia; Karayildirim, TamerFive triterpene saponins never reported before, hederifoliosides A-E, and four known triterpene saponins were isolated from the tubers of Cyclamen hederifolium. The structures of hederifoliosides A-E were determined as 3 beta,16 alpha-dihydroxy-13 beta,28-epoxyolean-30-oic acid 3-O-{[beta-D-glucopyranosyl-(1 -> 2)-O]-beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 4)-O-alpha-L-arabinopyranoside}, 3 beta,16 alpha-dihydroxy-13 beta, 28-epoxyolean-30-oic acid 3-O-{[beta-D-glucopyranosyl-(1 -> 2)-O]-beta-D-xylopyranosyl-(1 -> 2)-O-[beta-D-glucopyranosyl-(1 -> 3)]-O-beta-D-glucopyranosyl-(1 -> 4)-O-alpha-L-arabinopyranoside}, 3 beta,16 alpha-dihydroxy-13 beta, 28-epoxyolean-30-al 3-O-{[beta-D-glucopyranosyl-(1 -> 2)-O]-beta-D-xylopyranosyl-(1 -> 2)-O-[beta-D-glucopyranosyl-(1 -> 3)]-O-[beta-D-glucopyranosyl-(1 -> 6)]-O-beta-D-glucopyranosyl-(1 -> 4)-O-alpha-L-arabinopyranoside}, 30-O-beta-D-glucopyranosyl-(1 -> 2)-O -beta-D-glucopyranosyl-3 beta,16 alpha,30-trihydroxyolean-12-en-28-al 3-O-{[beta-D-glucopyranosyl-(1 -> 2)-O]-beta-D-xylopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-(1 -> 4)-O-alpha-L-arabinopyranoside}, 30-O-beta-D-glucopyranosyl-(1 -> 2)-O-beta-D-glucopyranosyl-3 beta,16 alpha,28,30-tetrahydroxyolean-12-en 3-O-{[beta-D-glucopyranosyl-(1 -> 2)-O]-beta-D-xylopyranosyl-(1 -> 2)-O-[beta-D-glucopyranosyl-(1 -> 3)]-O-beta-D-glucopyranosyl-(1 -> 4)-O-alpha-L-arabinopyranoside}, by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. The cytotoxic activity of the isolated compounds was evaluated against a small panel of cancer cell lines including Hela, H-446, HT-29, and U937. None of the tested compounds, in a range of concentrations between 1 and 50 mu M, caused a significant reduction of the cell number. (C) 2011 Elsevier Ltd. All rights reserved.Öğe Triterpenoid saponins from Astragalus wiedemannianus Fischer(Pergamon-Elsevier Science Ltd, 2010) Polat, Emre; Bedir, Erdal; Perrone, Angela; Piacente, Sonia; Alankus-Caliskan, OzgenThree cycloartane-type triterpene glycosides were isolated from Astragalus wiedemannianus together with eight known secondary metabolites namely cycloastragenol, cycloascauloside B, astragaloside IV, astragaloside VIII, brachyoside B, astragaloside II, astrachrysoside A, and astrasieversianin X. The structures were established mainly by a combination of 1D and 2D-NMR techniques as 3-O-[alpha-L-rhamnopyranosyl-( 1 -> 2)-beta-D-glucopyranosyl]-25-O-beta-D-glucopyranosyl-20(R),24(S)-epoxy-3 beta,6 alpha,16 beta,25-tetra-hydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-24-O-alpha-(4'-O-acetoxy)-L-arabinopyranosyl-16-O-acetoxy-3 beta,6 alpha,16 beta,24(S),25-pentahydroxycycloartane, 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]-6-O-beta-D-glucopyranosyl-24-O-alpha-L-arabinopyranosyl-16-O-acetoxy-3 beta,6 alpha,16 beta,24(S),25-pentahydroxycycloartane. To the best of our knowledge, the presence of an arabinose moiety on the acyclic side chain of cycloartanes is reported for the first time. (C) 2009 Elsevier Ltd. All rights reserved.