- Application of bacterial directed enzyme prodrug therapy as a targeted chemotherapy approach in a mouse model of breast cancer
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Cancer is the second leading cause of death in the world. Some of the usual cancer treatments include surgery, chemotherapy, and radiotherapy. However, due to low efficacy and side effects of these treatments, novel targeted therapeutic methods are needed. One of the common drawbacks of cancer chemotherapy is off-target toxicity. In order to overcome this problem, many investigations have been conducted. One of the new targeted therapy methods known as bacterial directed enzyme-prodrug therapy (BDEPT) employs bacteria as enzyme carriers to convert a pro-drug to a drug specifically within the tumor site. In the present study, we used Escherichia coli DH5α carrying luxCDABE gene cluster and overexpressing β-glucuronidase for luminescent emission and enzyme expression, respectively. Enzyme expression can lead to the conversion of glycyrrhizic acid as a prodrug to glycyrrhetinic acid, a potent anti-cancer agent. DH5α-lux/βG was characterized and its stability was also evaluated. Bacteria colonization in the tumor site was measured by tissue homogenate preparation and colony counting method. Histopathological studies on the liver, spleen, and tumor were also conducted. According to the results, co-treatment of 4T1, a highly metastatic mouse breast cancer cell line, with GL and DH5α-lux/βG could significantly decrease the IC50 values. Moreover, increased number of bacteria could lead to a dramatic drop in IC50 value. Specific colonization of DH5α-lux/βG was observed in the tumor site compared with other tissues (p 0.0001). Moreover, the biocompatibility evaluation proved that DH5α-lux/βG had no adverse effects on normal tissues. Furthermore, concurrent usage of GL and bacteria in the treatment of induced 4T1 tumors in BALB/c mice significantly delayed tumor growth (p0.001) during 16 days of investigation. Based on these findings, BDEPT might be useful for targeted breast cancer therapy, although further investigations are required to confirm this.
- Bahrami, Ahmad Reza,Hosseini-Giv, Niloufar,Matin, Maryam M.
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- A Reusable Column Method Using Glycopolymer-Functionalized Resins for Capture–Detection of Proteins and Escherichia coli
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The use of glycopolymer-functionalized resins (Resin–Glc), as a solid support, in?column mode for bacterial/protein capture and quantification is explored. The Resin–Glc is synthesized?from commercially available chloromethylated polystyrene?resin and glycopolymer, and is characterized by fourier transform infrared spectroscopy, thermogravimetry, and elemental analysis. The percentage of glycopolymer functionalized on Resin–Glc is accounted to be 5 wt%. The ability of Resin–Glc to selectively capture lectin, Concanavalin A, over Peanut Agglutinin, reversibly, is demonstrated for six cycles of experiments. The bacterial sequestration study using SYBR (Synergy Brands, Inc.) Green I tagged?Escherichia coli/Staphylococcus aureus?reveals the ability of Resin–Glc to selectively capture?E. coli?over?S. aureus. The quantification of captured cells in the column is carried out by enzymatic colorimetric assay using methylumbelliferyl glucuronide?as the substrate. The?E. coli?capture studies reveal a consistent capture efficiency of 105?CFU (Colony Forming Units) g?1 over six cycles. Studies with spiked tap water samples show satisfactory results for?E. coli?cell densities ranging from 102 to 107?CFU mL?1. The method portrayed can serve as a basis for the development of a reusable solid support in capture and detection of proteins and bacteria.
- Ajish, Juby K.,Abraham, Hephziba Maria,Subramanian, Mahesh,Kumar, K. S. Ajish
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- Isolation and identification of two new sargentodoxosides from Sargentodoxa cuneata and their agonistic effects against FXR
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Sargentodoxa cuneata (Oliv.) Rehd. et Wils is a traditional Chinese medicine to treat acute appendicitis, rheumarthritis, abdominal pain, and painful menstruation for a long history. The investigation of S. cuneata led to the isolation and identification of twenty-three secondary metabolites, including two new compounds, sargentodoxosides A (1) and B (2), and twenty-one known ones (3-23). Their structural characterization was conducted by HRESIMS, 1 D and 2 D NMR spectra. All the isolated compounds were assayed for their agonistic activities against the farnesoid X receptor (FXR). Nine of the isolated compounds displayed significant agonistic effects against FXR at 0.1 μM, suggesting that they could be served as potential agents for the development of FXR agonists.
- Zhang, Wen,Sun, Cheng-Peng,Peng, Yu-Lin,Zhao, Wen-Yu,Wang, Zheng-Yue,Ning, Jing,Lv, Xia,Yu, Zhen-Long,Zhou, Shuang,Peng, Wei,Fang, Bang-Jiang,Ma, Xiao-Chi
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- A novel acylated flavonol tetraglycoside and rare oleanane saponins with a unique acetal-linked dicarboxylic acid substituent from the xero-halophyte Bassia indica
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In recent years, the scientific interest and particularly the economic significance of halophytic plants has been highly demanding due to the medicinal and nutraceutical potential of its bioactive compounds. A xero-halophyte Bassia indica is deemed to be
- Othman, Ahmed,Amen, Yhiya,Shimizu, Kuniyoshi
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- Bioactive oleanane-type saponins from Hylomecon Japonica
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Six undescribed oleanane-type saponins, named as Hylomeconosides L-Q, were isolated from the whole herb of Hylomecon Japonica, their structures were determined by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HRESI-MS) and chromatographic data (GC and LC). Their structures were identified as 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-xylopyranosyl-(1 → 3)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-quinovopyranoside; 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl quillaic acid 28-O-β-D-xylopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranoside. Hylomeconosides L-Q showed selective cytotoxicities against human cancer cell lines A549, AGS, HeLa, Huh 7, HT29 and K562. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon Japonica and their bioactivities.
- Li, Fei,Ma, Chun-Liu,Qu, Ming-Hui,Wang, Guang-Shu,Wang, Yi-Xiao,Wu, Si-Tong,Yu, Bai-Hong
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- Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities
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Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
- Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu
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- Triterpene glycosides from Silene odontopetala
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Silene species are known for their use in traditional medicine in treating several diseases. To the authors’ knowledge there is no report on the chemical composition of S. odontopetala. Therefore, the phytochemical investigation of the methanol extract of S. odontopetala was carried out, leading to the isolation of six undescribed oleanane-type glycosides along with the known saponin azukisaponin IV. Their structures were elucidated by the analysis of 1D and 2D-NMR experiments, along with mass spectrometry analysis. The cytotoxic activity of oleanane-type saponins was evaluated against a small panel of cancer cell lines, including PC-3 (prostate carcinoma cells), MCF-7 (breast cancer cells), A549 (alveolar basal carcinoma cells), and HeLa (cervical carcinoma cells). Furthermore, the activity of isolated compounds against a normal cell line HEK-293, used for assessing their cytotoxicity, was evaluated.
- ün, Rabia Nur,Alankus, Ozgen,Karayildirim, Tamer,Masullo, Milena,Nalbantsoy, Ay?e,Piacente, Sonia
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- A immunosuppressive triterpenoid saponin from the stems of Epigynum griffithianum
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Chemical investigation of the stems of Epigunum griffithianum led to the isolation and identification of a new triterpenoid saponin (1) and two known compounds (epigynosides A (2) and B (3)). These structures were elucidated by means of spectroscopic analysis (1D and 2D NMR, MS, UV, IR) as well as comparison with the reported data. Compound 1 was evaluated in vitro for the immunosuppressive activities on proliferation of mice splenocyte and displayed significant immunosuppressive activities compared to the positive control (dexamethasone) with the concentration at 25 μM. (Figure presented.).
- Li, Wen-Yi,Wang, Qun,Wang, Yu-Dan
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supporting information
p. 1389 - 1393
(2018/12/04)
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- Flavonol Glycosides from Leaves of Allium microdictyon
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The composition of flavonoids from leaves of Allium microdictyon Prokh. (Amaryllidaceae) was studied for the first time and included 14 compounds including two new flavonol glycosides 1 and 2. UV, IR, and NMR spectroscopic and mass spectrometric data dete
- Olennikov
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p. 1035 - 1039
(2020/11/03)
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- Triterpene saponins from Silene gallica collected in North-Eastern Algeria
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Eleven previously undescribed triterpene saponins, named silenegallisaponin A-K (1–11), were isolated from the aerial parts of Silene gallica L. Their structures were elucidated by analysis of 1D and 2D-NMR spectroscopic data and mass spectrometry (HR-ESI-MS). The saponins comprised caulophyllogenin, echinocystic acid, or quillaic acid substituted at C-3 by a β-D-glucuronic acid or β-D-galactopyranosyl-(1 → 3)-β-D-glucuronopyranoside and at C-28 by a β-D-fucopyranose substituted at C-2 by a β-D-glucose and at C-3 by a β-D-glucose or a β-D-quinovose.
- Bechkri, Sara,Alabdul Magid, Abdulmagid,Sayagh, Charlotte,Berrehal, Djemaa,Harakat, Dominique,Voutquenne-Nazabadioko, Laurence,Kabouche, Zahia,Kabouche, Ahmed
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- Two New Triterpene Glycosides in the Roots of Uraria crinita
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Two new triterpene glycosides, 24-deoxyoxytrogenin 3-O-α-L-rhamnopyranosyl (1→2)[β-D-glucopyra-nosyl]-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranoside and sophoradiol 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucuronopyranosyl (1→2)-β-D-glucuronopyranoside with four known glycosides were isolated from a Chinese natural medicine, the roots of Uraria crinita (L.) DESV. Their structures were determined by chemical and spectral methods.
- Okawa, Masafumi,Akahoshi, Ryo,Kawasaki, Kyoko,Nakano, Daisuke,Tsuchihashi, Ryota,Kinjo, Junei,Nohara, Toshihiro
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p. 159 - 162
(2019/04/09)
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- Nocardamin glucuronide, a new member of the ferrioxamine siderophores isolated from the ascamycin-producing strain Streptomyces sp. 80H647
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A new siderophore glucuronide, nocardamin glucuronide (1), was isolated together with nocardamin (2) by applying the one strain-many compounds (OSMAC) approach to the ascamycin-producing strain, Streptomyces sp. 80H647, and performing multivariate analysis using mass spectral data. Structure elucidation was accomplished by a combination of NMR and MS analyses. The absolute configuration of the glucuronic acid moiety was found to be β-D-GlcA by hydrolysis using β-glucuronidase, subsequent derivatization of the hydrolysate, and comparison with standards. The siderophore activity of 1 was evaluated through the chrome azurol S assay and was comparable to that of 2 and deferoxamine (IC50 13.4, 9.5, and 6.3 μM, respectively). Nocardamin glucuronide (1) is the first example of a siderophore glucuronide.
- Lopez, Julius Adam V.,Nogawa, Toshihiko,Futamura, Yushi,Shimizu, Takeshi,Osada, Hiroyuki
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p. 991 - 995
(2019/08/26)
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- New triterpenoid saponins from the herb hylomecon japonica
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Background: Hylomecon japonica, a plant of the Papaveraceae family which is well-known for the alkaloids they produce, is a perennial plant widely distributed in the northeast, central and east regions of China. Although a variety of chemical constituents, including alkaloids, flavonoids, and megastigmoids, have been isolated from H. japonica, the investigation of saponins in H. japonica has not been reported until now. Methods: Various separation techniques, including polyporous resin column chromatography, silica gel column chromatography and hemi-preparative HPLC were applied to the isolation of triterpenoid saponins, and chemical methods such as acid hydrolysis and spectroscopic methods including HRESIMS and NMR were applied to their structure elucidation, and the XTT reduction method was used to assay cytotoxicity. Results: Two new triterpenoid saponins, named hylomeconoside A (1) and B (2) which were identified as 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-quinovopyranoside (1) and 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl-gypsogenin-28-O-β-D-xylopyranosyl- (1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside (2), and two known triterpenoid saponins identified as dubioside C (3) and lucyoside P (4) on the basis of spectroscopic and chemical evidence, were isolated from H. japonica. Compound 1 exhibited moderate cytotoxicity on MGC-803 and HL-60 cells, with IC50 values of 43.8 and 32.4 μg.mL-1, respectively. Conclusions: Compounds 1 and 2 are new saponins, and 1 is considered to be one of the antitumor principles in this plant. This is the first time that triterpenoid saponins have been isolated from plants of the Papaveraceae family.
- Qu, Yan-Fei,Gao, Jing-Yu,Wang, Jing,Geng, Yan-Mei,Zhou, Yu,Sun, Cheng-Xin,Li, Fei,Feng, Lei,Yu, Meng-Juan,Wang, Guang-Shu
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- Cytotoxic and hypoglycemic activity of triterpenoid saponins from camellia oleifera abel. Seed pomace
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One new and three known triterpenoid saponins were isolated and identified from Camellia oleifera seeds through IR, NMR, HR-ESI-MS and GC-MS spectroscopic methods, namely oleiferasaponin A3, oleiferasaponin A1, camelliasaponin B
- Di, Tai-Mei,Yang, Shao-Lan,Du, Feng-Yu,Zhao, Lei,Xia, Tao,Zhang, Xin-Fu
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- Astragalosidic acid: A new water-soluble derivative of astragaloside IV prepared using remarkably simple TEMPO-Mediated Oxidation
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There is an urgent need for a water-soluble derivative of astragaloside IV for drug R&D. In the present study, a remarkably simple method for the preparation of such a water-soluble derivative of astragaloside IV has been developed. This protocol involves oxidative 2,2,6,6-tetramethylpiperidine-1-oxyl free radical (TEMPO)-mediated transformation of astragaloside IV to its carboxylic acid derivative, which is a new compound named astragalosidic acid. The structure of astragalosidic acid was elucidated by means of spectroscopic analysis. Its cardioprotective activity was investigated using an in vitro model of cardiomyocyte damage induced by hypoxia/reoxygenation in H9c2 cells. The oxidative TEMPO-mediated transformation proposed in the present study could be applied to other natural saponins, offering an effective and convenient way to develop a new compound with greatly improved structure-based druggability.
- Qing, Lin-Sen,Peng, Shu-Lin,Liang, Jian,Ding, Li-Sheng
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- New Flavonoid Glucuronides from the Aerial Part of Scutellaria intermedia
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The aerial part of the plant Scutellaria intermedia Popov yielded five glucuronides, three of which were identified as chrysin 7-O-β-D-glucuronide, wogonin 7-O-β-D-glucuronide, and baicalein 7-O-β-Dglucuronide (baicalin). IR, UV, PMR, and 13C N
- Karimov,Slobodyanyuk,Botirov, E. Kh.
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p. 638 - 641
(2017/10/06)
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- α -Amylase and α -Glucosidase Inhibitory Saponins from Polyscias fruticosa Leaves
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Three bisdesmosidic saponins 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (1), polyscioside D (2), and 3-O- { β -D-glucopyranosyl-(1 → 2)-[β-D-glucopyranosyl-(1 → 4)]-β-D- g l u c u r o n o p y r a n o s y l } oleanolic acid 28-O-β-D-glucopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3) were isolated from a methanol extract of Polyscias fruticosa (L.) Harms leaves. Compound 1 was obtained as a main constituent and compound 3 was reported for the first time and named as polyscioside I. Saponin 1 inhibited porcine pancreas α-amylase and yeast α-glucosidase activities while 2 and 3 were inactive. Synergistic inhibitory effect on α-amylase was observed from the combination of low concentrations of 1 and acarbose. The findings suggest the use of P. fruticosa and its major saponin 1 for the prevention and treatment of diabetes and its complications.
- Hanh, Tran Thi Hong,Dang, Nguyen Hai,Dat, Nguyen Tien
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- New Flavonol Glucuronides from the Flower Buds of Syzygium aromaticum (Clove)
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Repeated chromatography of the EtOAc-soluble fraction from the 70% EtOH extract of the flower buds of Syzygium aromaticum (clove) led to the isolation and characterization of four new flavonol glucuronides, rhamnetin-3-O-β-d-glucuronide (1), rhamnazin-3-O-β-d-glucuronide (2), rhamnazin-3-O-β-d-glucuronide-6″-methyl ester (3), and rhamnocitrin-3-O-β-d-glucuronide-6″-methyl ester (4), together with 15 flavonoids (5-19) having previously known chemical structures. The structures of the new compounds 1-4 were determined by interpretation of spectroscopic data, particularly by 1D- and 2D-NMR studies. Six flavonoids (6, 7, 9, 14, 18, and 19) were isolated from the flower buds of S. aromaticum for the first time in this study. The flavonoids were examined for their cytotoxicity against human ovarian cancer cells (A2780) using MTT assays. Among the isolates, pachypodol (19) showed the most potent cytotoxicity on A2780 cells with an IC50 value of 8.02 μM.
- Ryu, Byeol,Kim, Hye Mi,Lee, Jin Su,Lee, Chan Kyu,Sezirahiga, Jurdas,Woo, Jeong-Hwa,Choi, Jung-Hye,Jang, Dae Sik
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p. 3048 - 3053
(2016/05/19)
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- Molecular structure, chemical properties and biological activities of Pinto bean pod polysaccharide
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Pinto bean pod polysaccharide (PBPP) was successfully extracted with yield of 38.5 g/100 g and the PBPP gave total carbohydrate and uronic acid contents of 286.2 mg maltose equivalent/g and 374.3 mg Gal/g, respectively. The Mw of PBPP was 270.6 kDa with intrinsic viscosity of 0.262 dm3/g, which composed of mannose (2.5%), galacturonic acid (15.0%), rhamnose (4.0%), glucose (9.0%), galactose (62.2%), xylose (2.9%) and arabinose (4.3%) with trace amount of ribose and fucose. The result suggested that PBPP has a spherical conformation with a highly branched structure. Fourier Transform Infrared analysis showed that PBPP has a similar structure as commercial pectin with an esterification degree of 59.9%, whereas scanning electron microscopy study showed that the crude polysaccharide formed a thin layer of film that was made of multiple micro strands of fibre. PBPP exhibited substantial free radical scavenging activity (7.7%), metal reducing capability (2.04 mmol/dm3) and α-amylase inhibitory activity (97.6%) at a total amount of 1 mg. PBPP also exhibited high water- and oil-holding capacities (3.6 g/g and 2.8 g/g, respectively). At a low concentration, PBPP exhibited emulsifying activity of 39.6% with stability of 38.6%. Apart from that, PBPP was able to show thickening capability at low concentration (0.005 kg/dm3).
- Kamarudin, Fazlina,Gan, Chee-Yuen
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p. 280 - 287
(2016/04/19)
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- Hydrolysis behaviors of sugarcane bagasse pith in subcritical carbon dioxide-water
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The aim of this study was to describe the hydrolysis behavior of sugarcane bagasse pith (SCBP) in subcritical CO2-water. The hydrolysis was carried out in a batch reactor using different temperatures (160 to 260 °C), liquid to solid ratios (20:1 to 100:1), CO2 pressures (0 to 7.3 MPa), stirring speeds (0 to 500 rpm) and reaction times (0 to 40 min). The highest total reducing sugar yield (43.6%) was obtained at 200 °C, liquid to solid ratio 30:1, 2 MPa CO2, 500 rpm and 50 min. Two-dimensional heteronuclear single quantum coherence (2D HSQC) nuclear magnetic resonance (NMR), scanning electron microscopy (SEM) and Fourier transform infrared spectrometry (FT-IR) were used to help elucidate the physical and chemical characteristics of the raw material and residual solid particles, with results consistent with the removal of hemicellulose during hydrolysis. The changes in the concentration of products with time were analyzed to understand product distribution through high-performance liquid chromatography (HPLC) and to infer the reaction mechanism.
- Liang, Jiezhen,Chen, Xiaopeng,Wang, Linlin,Wei, Xiaojie,Qiu, Feifei,Lu, Chaochao
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p. 99322 - 99330
(2016/11/02)
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- ELECTROCHEMICAL METHODS AND COMPOUNDS FOR THE DETECTION OF ENZYMES
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Disclosed are compositions and methods for the electrochemical detection of enzymes, such as enzymes that are indicative of disease, disorders, or pathogens, such as viruses, bacteria, and fungi, or other disorders. These methods can be used in point-of- care diagnostic assays for the detection of disease, disorder, or pathogen (e.g., to identify the strain of pathogen infecting a patient in a healthcare setting). The electrochemical methods described herein can also be used to assess the susceptibility of a pathogen to an antipathogen drug. Also provided are probes suitable for use in conjunction with the methods described herein.
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Page/Page column 21
(2016/04/26)
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- Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury
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Seven new triterpenoids (1-7), together with two known ones (8-9), were isolated from the aerial parts ofIlex cornuta. The leaves of I. cornuta are the major source of "Kudingcha", a popular herbal tea consumed in China and other countries. The structures of compounds 1-7 were determined as 20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (1), 20-epi-urs-12,18-dien-28-oic acid 2′-O-acetyl-3β-O-α-l-arabinopyranoside (2), 20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (3), 3β,23-dihydroxy-20-epi-urs-12,18-dien-28-oic acid (4), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-α-l-arabinopyranoside (5), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronic acid (6), 23-hydroxy-20-epi-urs-12,18-dien-28-oic acid 3β-O-β-d-glucuronopyranoside-6-O-methyl ester (7), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and chemical reactions. Protective effects against H2O2-induced H9c2 cardiomyocyte injury were tested in vitro for compounds 1-9, and the data showed that compound 4 had significant cell-protective effect. Compounds 1-9 did not show significant DPPH radical scavenging activity.
- Li, Shanshan,Zhao, Jianping,Wang, Wenlian,Lu, Yuchen,Xu, Qiongming,Liu, Yanli,Li, Xiaoran,Khan, Ikhlas A.,Yang, Shilin
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p. 178 - 184
(2015/11/03)
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- New triterpenoid glycosides from the roots of camellia oleifera abel
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Five new triterpenoid saponins, oleiferosides I-M (1-5, resp.) were isolated from the roots of Camellia oleifera Abel. Their structures were elucidated by a combination of 1D- and 2D-NMR spectroscopy, mass spectrometry, and chemical methods. All the compounds were identified as oleanane-type saponins with sugar moieties linked to C(3) of the aglycone. In addition, cytotoxic activities of these saponins were evaluated against four human tumor cell lines (A549, B16, BEL-7402, and MCF-7) by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) in vitro assay. All of the compounds showed significant cytotoxic activities against the tested cell lines.
- Li, Xia,Zhao, Jianping,Li, Xiaoran,Liu, Yanli,Xu, Qiongming,Khan, Ikhlas A.,Yang, Shilin
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p. 496 - 508
(2015/04/27)
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- Oleanane triterpenes from the flowers of camellia japonica inhibit porcine epidemic diarrhea virus (PEDV) replication
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Porcine epidemic diarrhea virus (PEDV) infections have resulted in a severe economic loss in the swine industry in many countries due to no effective treatment approach. Fifteen oleanane triterpenes (1-15), including nine new ones (1-4 and 10-14), were isolated from the flowers of Camellia japonica, and their molecular structures were determined by extensive spectroscopic methods. These compounds were evaluated for their antiviral activity against PEDV replication, and the structure-activity relationships (SARs) were discussed. Compounds 6, 9, 11, and 13 showed most potent inhibitory effects on PEDV replication. They were found to inhibit PEDV genes encoding GP6 nucleocapsid, GP2 spike, and GP5 membrane protein synthesis based on RT-PCR data. Western blot analysis also demonstrated their inhibitory effects on PEDV GP6 nucleocapsid and GP2 spike protein synthesis during viral replication. The present study suggested the potential of compounds 6, 9, 11, and 13 as promising scaffolds for treating PEDV infection via inhibiting viral replication.
- Yang, Jun-Li,Ha, Thi-Kim-Quy,Dhodary, Basanta,Pyo, Euisun,Nguyen, Ngoc Hieu,Cho, Hyomoon,Kim, Eunhee,Oh, Won Keun
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p. 1268 - 1280
(2015/03/04)
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- Hepatoprotective triterpene saponins from the roots of Glycyrrhiza inflata
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Two novel oleanane-type triterpene saponins, licorice-saponin P2 (1) and licorice-saponin Q2 (3), together with nine known compounds 2, 4-11, have been isolated from the water extract of the roots of Glycyrrhiza inflata. The structures of these compounds were elucidated on the basis of spectroscopic analysis, including 2D-NMR experiments (1H-1H COSY, HSQC, HMBC and ROESY). In in vitro assays, compounds 2-4, 6 and 11 showed significant hepatoprotective activities by lowering the ALT and AST levels in primary rat hepatocytes injured by D-galactosamine (D-GalN). In addition, compounds 2-4, 6, 7 and 11 were found to inhibit the activity of PLA2 with IC50 values of 6.9 μM, 3.6 μM, 16.9 μM, 27.1 μM, 32.2 μM and 9.3 μM, respectively, which might be involved in the regulation of the hepatoprotective activities observed.
- Zheng, Yun-Feng,Wei, Juan-Hua,Fang, Shi-Qi,Tang, Yu-Ping,Cheng, Hai-Bo,Wang, Tian-Lin,Li, Cun-Yu,Peng, Guo-Ping
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p. 6273 - 6283
(2015/05/13)
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- Electrocatalytic synthesis of poly(2,6-diaminopyridine) on reduced graphene oxide and its application in glucose sensing
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Reduced graphene oxide (RGO) was prepared via electrochemical reduction of graphene oxide (GO), and it can effectively catalyze the polymerization of 2,6-diaminopyridine. Poly(2,6-diaminopyridine) (PDAP) deposited on RGO (PDAP-RGO) has good electroactivity in a wide pH range until pH 11.0. Due to the electrocatalytic reduction of H2O2 at the PDAP-RGO, a platform for glucose sensing was constructed by immobilizing glucose oxidase (GOD) into the PDAP-RGO. The proposed glucose sensor exhibited a wide linear range from 0.05 to 6.65 mM, a low detection limit of 0.142 μM, a good reproducibility and stability. The apparent Michaelis-Menten constant of GOD was also calculated based on the relationship between steady-state current and glucose concentration.
- Qin, Yong,Yuan, Jie,Ma, Jianfeng,Kong, Yong,Xue, Huaiguo,Peng, Yonggang
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p. 52896 - 52901
(2015/06/25)
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- H2O2-mediated fluorescence quenching of double-stranded DNA templated copper nanoparticles for label-free and sensitive detection of glucose
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Blood glucose monitoring has attracted extensive attention because diabetes mellitus is a worldwide public health problem. Here, a novel and label-free fluorescent sensing strategy was reported for simple and sensitive detection of glucose in human serum on the basis of H2O2-mediated fluorescence quenching of double-stranded DNA (ds-DNA) templated copper nanoparticles (Cu NPs). In this strategy, the fluorescence intensity of ds-DNA templated Cu NPs was found to be quenched effectively in the presence of H2O2. Similarly, glucose could be monitored based on the enzymatic conversion of glucose by glucose oxidase to generate H2O2. Under the optimized conditions, the strategy exhibited sensitive and selective detection of glucose in a linear range from 50 nM to 100 μM and with a detection limit of 12 nM. In addition, the method was successfully applied in the detection of glucose in human serum samples with satisfactory results. Furthermore, the strategy was free of any fluorescence dye label, complex DNA sequence design, and sophisticated experimental techniques. Therefore, the proposed approach could hold great potential for diabetes mellitus research and clinical diagnosis.
- Wang, Hai-Bo,Zhang, Hong-Ding,Chen, Ying,Li, Yang,Gan, Tian
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p. 77906 - 77912
(2015/09/28)
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- Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization-tandem mass spectrometry: Evidence and tags to distinguish different glycosaminoglycans
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Diverse monosaccharide analysis methods have been established for a long time, but few methods are available for a complete monosaccharide analysis of glycosaminoglycans (GAGs) and certain acidolysis- resistant components derived from GAGs. In this report, a reversed-phase high-performance liquid chromatography (RP-HPLC) method with pre-column 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization was established for a complete monosaccharide analysis of GAGs. Good separation of glucosamine/ mannosamine (GlcN/ManN) and glucuronic acid/iduronic acid (GlcA/IdoA) was achieved. This method can also be applied to analyze the acidolysis-resistant disaccharides derived from GAGs, and the sequences of these disaccharides were confirmed by electrospray ionization-collision-induced dissociation- tandem mass spectrometry (ESI-CID-MS/MS). These unique disaccharides could be used as markers to distinguish heparin/heparan sulfate (HP/HS), chondroitin sulfate/dermatan sulfate (CS/DS), and hyaluronic acid (HA).
- Zhu, He,Chen, Xuan,Zhang, Xiao,Liu, Lili,Cong, Dapeng,Zhao, Xia,Yu, Guangli
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- Monoterpene glycosides, phenylpropanoids, and acacetin glycosides from Dracocephalum foetidum
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Chemical investigation of the acetone extract from the aerial parts of the Mongolian medicinal plant Dracocephalum foetidum resulted in the isolation of three limonene glycosides, a caffeic acid trimer, four rosmarinic acid glucosides, and five acacetin acyl glycosides, together with 13 known natural products. The chemical structures of all of the compounds were determined by spectroscopic analyses. Among these compounds three showed hyaluronidase inhibitory activity. In addition, one other compound showed stronger 1,1-diphenyl-2-picrylhydrazyl radical scavenging activity than the positive control Trolox, whereas three other compounds demonstrated a similar activity to that of Trolox.
- Selenge, Erdenechimeg,Murata, Toshihiro,Tanaka, Shiho,Sasaki, Kenroh,Batkhuu, Javzan,Yoshizaki, Fumihiko
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- Aromatic glycoside from flue-cured tobacco (Nicotiana tabacum) Leaves and its pyrolysis behavior studied by pyrolysis-GC/MS
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The aromatic glycoside, named benzyl-6-O-α-L-arabinopyranosyl(1-6)- β-D-glucopyranoside, was isolated from the leaves of Nicotiana tabacum L. The structure of which was elucidated by analysis of its spectroscopic data. This compound's thermal behavior and pyrolysis products were also investigated by on-line pyrolysis-gas chromatography mass spectroscopy (Py-GC/MS) at 300, 500, 700, 900 °C. The results indicated that, due to the primary decomposition reaction of the O-glycosidic bound's cleavage, the characteristic and main pyrolysis product was the typical aroma constituent benzyl alcohol, suggesting that glycoside would contribute to produce specific aroma for tobacco products on heating as a novel aroma precursor.
- Yuan,Zhou,Li,Feng
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p. 3620 - 3622
(2014/08/05)
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- Structure and gene cluster of the O-antigen of Escherichia coli O30
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The acidic O-polysaccharide (O-antigen) of Escherichia coli O30 was isolated from the lipopolysaccharide and studied by sugar analysis and NMR spectroscopy. The following structure of the branched tetrasaccharide repeating unit was established, which is u
- Perepelov, Andrei V.,Hao, Xiyan,Senchenkova, Sof'Ya N.,Shashkov, Alexander S.,Liu, Bin,Wang, Lei,Knirel, Yuriy A.
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p. 196 - 198
(2014/05/20)
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- CHONDROITIN COMPLEXES FOR TRANSCUTANEOUS ABSORPTION
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The present invention relates to the use of chondroitin as a transdermal carrier and slow-release system for active ingredients in pharmaceutical and cosmeceutical compositions.
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Page/Page column 9; 10
(2014/02/16)
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- Water-soluble polysaccharides from finger citron fruits (Citrus medica L. var. sarcodactylis)
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Four water-soluble polysaccharides, FCp-1, FCp-2, FCp-3, and FCp-4 were obtained from finger citron fruits (Citrus medica L. var. sarcodactylis) by hot-water extraction and ethanol precipitation, followed by routine separation procedure. Based on the calibration curve, molecular weights of them were estimated to be 113.9, 32.6, 140.3, and 177.1 kDa respectively. The acid hydrolysis, methylation, IR, GC-MS, and NMR experiments were used for composition analysis. FCp-1 was a heteropolysaccharide composed of arabinose, galactose, glucose, rhamnose, and xylose, with a molar ratio of 3.0:7.0:4.1:1.0:1.5. FCp-2 and FCp-4 were →4)-α-d-GalpA(1→ linking galacturonan differ in molecular weights. FCp-3 was a →6)-α-d-Glcp(1→ linking glucan. According to the results of in vitro assays, FCp-3 showed significantly and moderately enhancing capacities toward the proliferation of splenocytes and thymocytes respectively. Thus, FCp-3 or analogs may have further use as immunomodulatory agents.
- He, Zhengchun,Liang, Fengjie,Zhang, Yuyang,Pan, Yuanjiang
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p. 100 - 104
(2014/04/03)
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- Evidence that GH115 α-glucuronidase activity, which is required to degrade plant biomass, is dependent on conformational flexibility
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The microbial degradation of the plant cell wall is an important biological process that is highly relevant to environmentally significant industries such as the bioenergy and biorefining sectors. A major component of the wall is glucuronoxylan, a β1,4-linked xylose polysaccharide that is decorated with α-linked glucuronic and/or methylglucuronic acid (GlcA/MeGlcA). Recently three members of a glycoside hydrolase family, GH115, were shown to hydrolyze MeGlcA side chains from the internal regions of xylan, an activity that has not previously been described. Here we show that a dominant member of the human microbiota, Bacteroides ovatus, contains a GH115 enzyme, BoAgu115A, which displays glucuronoxylan α-(4-Omethyl)-glucuronidase activity. The enzyme is significantly more active against substrates in which the xylose decorated with GlcA/MeGlcA is flanked by one or more xylose residues. The crystal structure of BoAgu115A revealed a four-domain protein in which the active site, comprising a pocket that abuts a cleft-like structure, is housed in the second domain that adopts a TIM barrel-fold. The third domain, a five-helical bundle, and the C-terminal β-sandwich domain make inter-chain contacts leading to protein dimerization. Informed by the structure of the enzyme in complex with GlcA in its open ring form, in conjunction with mutagenesis studies, the potential substrate binding and catalytically significant amino acids were identified. Based on the catalytic importance of residues located on a highly flexible loop, the enzyme is required to undergo a substantial conformational change to form a productive Michaelis complex with glucuronoxylan.
- Rogowski, Artur,Basle, Arnaud,Farinas, Cristiane S.,Solovyova, Alexandra,Mortimer, Jennifer C.,Dupree, Paul,Gilbert, Harry J.,Bolam, David N.
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- Three new triterpene saponins from roots of Eryngium planum
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Saponin composition of the roots of Eryngium planum L. was investigated. Triterpene saponins found in E. planum and also present in Eryngium maritimum were different from those described previously in Eryngium campestre L. Three primary saponins were isol
- Kowalczyk, Mariusz,Masullo, Milena,Thiem, Barbara,Piacente, Sonia,Stochmal, Anna,Oleszek, Wies?aw
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p. 653 - 660
(2014/05/06)
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- A single molecule perspective on the functional diversity of in vitro evolved β-glucuronidase
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The mechanisms that drive the evolution of new enzyme activity have been investigated by comparing the kinetics of wild-type and in vitro evolved β-glucuronidase (GUS) at the single molecule level. Several hundred single GUS molecules were separated in large arrays of 62 500 ultrasmall reaction chambers etched into the surface of a fused silica slide to observe their individual substrate turnover rates in parallel by fluorescence microscopy. Individual GUS molecules feature long-lived but divergent activity states, and their mean activity is consistent with classic Michaelis-Menten kinetics. The large number of single molecule substrate turnover rates is representative of the activity distribution within an entire enzyme population. Partially evolved GUS displays a much broader activity distribution among individual enzyme molecules than wild-type GUS. The broader activity distribution indicates a functional division of work between individual molecules in a population of partially evolved enzymes that-as so-called generalists-are characterized by their promiscuous activity with many different substrates.
- Liebherr, Raphaela B.,Renner, Max,Gorris, Hans H.
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supporting information
p. 5949 - 5955
(2014/05/20)
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- Triterpenoid saponins from the roots of two Gypsophila species
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Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-D-galactopyranosyl-(1->2)-[β-D-xylopyranos yl-(1 → 3)]-β-D-glucuronopyranosylquillaic acid 28-O-β-D-xylopyranosyl-(1 →4)-[β-D-glucopyranosyl-(1 →3)]-α-L-rhamnopyranosyl-(1 →2)-[β-D-glucopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucuronopyranosylgypsogenin 28-O-β-D-xylop yranosyl-(1 →4)-[β-D-glucopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1 →2)-[β-D-glucopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 →2)-[β-D-xylopyranosyl-(1 →3)]-β-D-glucurono pyranosylgypsogenin 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-D-quinovopyranosyl-(1 →4)]-β-D-fucopyranosyl ester (3), gypsogenic acid 28-O-β-D-glucopyranosyl-(1 →3)-{6-O-[3-hydroxy-3-methylglutaryl]-β-D-glucopyranosyl-(1→6)}-β-D-galactopyranosyl ester (4). Three compounds were evaluated against one human colon cancer cell line SW480 and one rat cardiomyoblast cell line H9c2.
- Pertuit, David,Avunduk, Sibel,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Paululat, Thomas,Delemasure, Stphanie,Dutartre, Patrick,Lacaille-Dubois, Marie-Aleth
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p. 182 - 188
(2015/03/14)
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- Regenerative labeling of saccharides
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A simple method for regenerative labeling of saccharides is devised by using (naphth-2-ylmethoxy)amine or N-methyl-(naphth-2-ylmethoxy)amine. The naphthyl group is optically responsive to facilitate the separation of labeled saccharides, which are subsequently reverted to the parental saccharides by one-pot hydrogenolysis-hydrolysis using co-catalysts Pd(OH)2 and HCl under an atmosphere of H2. The mechanistic study indicates that the naphthylmethyl group plays an essential role in the initial hydrogenolysis, followed by in situ hydrolysis, to regenerate the saccharides.
- Wen, Hao-Yu,Hsu, Peng-Hao,Chen, Guei-San,Fang, Jim-Min
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p. 9530 - 9533
(2013/07/27)
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- Isolation and structural determination of triterpenoid glycosides from the aerial parts of alsike clover (Trifolium hybridum L.)
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Five azukisapogenol glycosides (1-5) have been isolated from the aerial parts of alsike clover (Trifolium hybridum L.), and their structures were elucidated by combined spectroscopic, spectrometric (1D and 2D NMR; HRESIMS, ESI-MS/MS), and chemical methods. Three of them are new compounds and were identified as 3-O-[-α-l-arabinopyranosyl(1→2)]-β-d- glucuronopyranosyl azukisapogenol (1), 3-O-[-β-d- glucuronopyranosyl(1→2)-β-d-glucuronopyranosyl]-29-O-β-d- glucopyranosyl azukisapogenol (2), and 3-O-[-α-l- arabinopyranosyl(1→2)-β-d-glucuronopyranosyl]-29-O-β-d- glucopyranosyl azukisapogenol (3). The remaining two (4, 5) are known compounds but have not been previously described as saponins constituents of the genus Trifolium. Also, azukisapogenol is reported here as a triterpenoid aglycone for the first time in this genus. Finally, the main chemotaxonomic features that may be recognized as specific of Trifolium species were discussed.
- Perez, Andy J.,Kowalczyk, Mariusz,Simonet, Ana M.,Macias, Francisco A.,Oleszek, Wieslaw,Stochmal, Anna
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p. 2631 - 2637
(2013/05/21)
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- Comparison of physicochemical characteristics and anticoagulant activities of polysaccharides from three sea cucumbers
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In order to search for sulfated polysaccharides in different invertebrate connective tissues and to examine their biological activities, we have isolated three types of polysaccharides from the body wall of the three sea cucumbers Holothuria edulis, Apostichopus japonicas and Holothuria nobilis. The physicochemical properties and anticoagulant activities of these polysaccharides were examined and compared. The chemical composition analysis and nuclear magnetic resonance (NMR) analysis indicate that two types of polysaccharides, sulfated fucan and fucosylated chondroitin sulfate (FuCS), were found in all of the three species and in addition a neutral glycan was observed in H. edulis. The neutral a-glucan was firstly obtained from sea cucumber. The same type of polysaccharides from different species of sea cucumbers have similar physicochemical properties and anticoagulant activities, but those of different types of glycans are significantly different, possibly due to their different monosaccharide compositions, electric charges and average molecular weights. The FuCSs have stronger anticoagulant activities than the sulfated fucans, although the molecular sizes of the FuCSs are lower than those of the sulfated fucans, whereas the neutral glucan has no activity, as expected from the absence of sulfate. Thus, anticoagulant activities of the different type of polysaccharides are likely to relate to monosaccharide composition and sulfate content. Preliminary analysis suggests that the sulfation patterns of the FuCSs may result in the difference in anticoagulant activities. Our data could help elucidate the structure-activity relationship of the sea cucumber polysaccharides.
- Luo, Lan,Wu, Mingyi,Xu, Li,Lian, Wu,Xiang, Jingying,Lu, Feng,Gao, Na,Xiao, Chuang,Wang, Shengmin,Zhao, Jinhua
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p. 399 - 417
(2013/05/09)
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- Triterpenoid glycosides from the stems of Gordonia kwangsiensis
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Eleven oleanane-type triterpenoid glycosides, named gordonsaponins A-K, were isolated from the stems of Gordonia kwangsiensis. Their structures were elucidated by spectroscopic and chemical methods. The cytotoxic activities of all eleven were evaluated against five human tumor cell lines (HCT-8, Bel-7402, BGC-823, A549, and A2780), with only one having activity against all tested cell lines, with IC50 values ranging from 0.1 to 2.41 μM.
- Fu, Hui-Zheng,Li, Chuang-Jun,Yang, Jing-Zhi,Chen, Xiao-Guang,Zhang, Dong-Ming
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p. 167 - 174
(2013/02/23)
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- Two new triterpenoid saponins from Caragana microphylla seeds
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Two new triterpenoid saponins, caraganins A and B (1 and 2), structurally characterized by a 22-oxo group, were isolated from the seeds of Caragana microphylla Lam., together with their n-butyl esters as artifacts (1a and 2a). Their structures and configurations were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. Compounds 1a and 2a exhibited potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration values ranging from 3.125 to 6.25 μg/ml.
- Zheng, Cheng-Jian,Jin, Gui-Lin,Zou, Jing-Ping,Jiang, Yi-Ping,Sun, Pei-Xin,Qin, Lu-Ping
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p. 190 - 195
(2013/02/25)
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- Medicinal flowers. XXXVI.1) Acylated oleanane-type triterpene saponins with inhibitory effects on melanogenesis from the flower buds of Chinese Camellia japonica
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Four acylated oleanane-type triterpene oligoglycosides, sanchakasaponins E-H, were isolated from the flower buds of Camellia japonica cultivated in Yunnan province, China, together with four known triterpene oligoglycosides. The chemical structures of the new triterpene oligoglycosides were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of the triterpene oligoglycoside constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were investigated.
- Nakamura, Seikou,Fujimoto, Katsuyoshi,Nakashima, Souichi,Matsumoto, Takahiro,Miura, Tomoko,Uno, Kaoru,Matsuda, Hisashi,Yoshikawa, Masayuki
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experimental part
p. 752 - 758
(2012/09/25)
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- Evaluation of novel antioxidant triterpenoid saponins from the halophyte Salicornia herbacea
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As a part of an ongoing search for novel antioxidants from the salt marsh plants, bioactivity-isolation and structure determination of constituents from Salicornia herbacea were performed. One new triterpenoid saponin (4), along with three known saponins (1-3), has been isolated from n-BuOH fraction of S. herbacea. On the basis of the spectroscopic methods, the structure of the new saponin 4 was elucidated as 3β-hydroxy-23-oxo-30-noroleana-12, 20(29)-diene-28-oic acid 3-O-β-d-glucuronopyranosyl-28-O-β-d- glucopyranoside. Scavenging effects of saponins 1-4 were examined on 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical and peroxynitrite. Particularly, saponin 3 exerted significant antioxidant activity on both authentic peroxynitrite and peroxynitrite generated from morpholinosydnonimine (SIN-1).
- Kim, You Ah,Kong, Chang-Suk,Lee, Jung Im,Kim, Hojun,Park, Hee Yeon,Lee, Hyi-Seung,Lee, Chulhyun,Seo, Youngwan
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experimental part
p. 4318 - 4322
(2012/09/22)
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- α-Glucosidase inhibitory constituents from Acanthopanax senticosus Harm leaves
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A new triterpene glycoside, 3-O-[(α-L-rhamnopyranosyl)(1→2)]- [β-Dglucuronopyranosyl-6-O-methyl ester]-olean-12-ene-28-olic acid (1) and a new indole alkaloid, 5-methoxy-2-oxoindolin-3-acetic acid methyl ester (5) were isolated from the leaves of Acanthopanax senticosus Harms along with six known compounds. The structures of the new compounds were determined by means of 2D-NMR experiments and chemical methods. All the isolated compounds were evaluated for their glycosidase inhibition activities and compound 6 showed significant α-glucosidase inhibition activity.
- Wang, Zhi-Bin,Jiang, Hai,Xia, Yong-Gang,Yang, Bing-You,Kuang, Hai-Xue
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experimental part
p. 6269 - 6276
(2012/09/07)
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- Triterpene glycosides from astragalus angustifolius
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Six new cycloartane-type (1-6) and four new oleanane-type (7-10) triterpene glycosides were isolated from Astragalus angustifolius Lam., together with five known triterpene glycosides. Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analysis. Compounds 1-3 are glycosides of cycloastragenol, while compounds 4-6 show the C-24 epimer of cycloastragenol as aglycone, encountered for the first time in nature. All compounds were evaluated for their antiproliferative activity in Hela, H-446, HT-29, and U937 cell lines. Only compound 8 displayed a weak activity with IC50 values of 36 and 50 μM against Hela and HT-29 cell lines, respectively. Georg Thieme Verlag KG Stuttgart · New York.
- Guelcemal, Derya,Masullo, Milena,Bedir, Erdal,Festa, Michela,Karayldrm, Tamer,Alankus-Caliskan, Ozgen,Piacente, Sonia
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experimental part
p. 720 - 729
(2012/07/16)
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- Cytotoxic triterpenoid saponins from Aesculus glabra Willd.
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Twenty-four acylated polyhydroxyoleanene saponins were isolated from the seeds of Aesculus glabra. Sixteen of them, namely aesculiosides G1-G16 (1-16), were determined as compounds by spectroscopic and chemical analysis. The structural features of all 24 saponins are: (1) arabinofuranosyl units affixed to C-3 of the glucuronopyranosyl unit in the trisaccharide chain; (2) no 24-OH substitution; (3) C-2 sugar moiety substitution of the 3-O-glucuronopyranosyl unit is either glucopyranosyl or galactopyranosyl. The features of these isolated saponin structures provide more evidence for chemical taxonomy within the genus Aesculus. The cytotoxicity of the aesculiosides (1-16) were tested against A549 and PC-3 cancer cell lines with GI50 from 5.4 to >25 μM.
- Yuan, Wei,Wang, Ping,Deng, Guangrui,Li, Shiyou
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experimental part
p. 67 - 77
(2012/04/04)
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- Simultaneous determination of uronates found in polysaccharides from natural products by HPLC with fluorometric detection
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A sensitive high-performance liquid chromatographic (HPLC) method for the determination of uronates isolated from polysaccharides found in natural products such as glycosaminoglycans and alginate is described. Preparation of iduronate, guluronate, and mannuronate as analytical standards for high performance liquid chromatography was achieved by depolymerization of dermatan sulfate and alginate in 2.5 mol L-1 trifluoroacetic acid at 100 °C for 6 h. Structures of resulting products (iduronate, guluronate, and mannuronate) were characterized by 600 MHz 1H NMR. Five uronates (glucuronate, iduronate, mannuronate, guluronate, and galacturonate) were separated on a Dionex CarboPac PA1 column using an isocratic elution with 8 mmol L-1 acetate buffer (pH 4.84) and were monitored by fluorescence detection using 1.5% 2-cyanoacetamide as a post-column fluorogenic reagent. As little as 50 pmol of each uronate could be detected with excitation at 331 nm and emission at 383 nm.
- Matsumoto, Akihisa,Hosoyama, Saori,Higashi, Kyohei,Toida, Toshihiko
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