- Colorimetric detection of glucose by a hybrid nanomaterial based on amplified peroxidase-like activity of ferrosoferric oxide modified with gold-platinum heterodimer
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The colorimetric detection of glucose using hybrid nanostructures is a rapidly growing research hotspot. In this work, we established a simple route for the synthesis of a class of multi-metal hybrid nanostructure materials and investigated their peroxidase-like performance for the colorimetric detection of glucose. The hybrid nanomaterial (Fe3O4@Au-Pt) incorporated ferrosoferric oxide nanoparticles (Fe3O4NPs) and heterodimers composed of gold (Au) and platinum (Pt), which presents excellent morphology and structure. On the basis of our research, we constructed an easy and sensitive colorimetric sensor for the detection of glucose and hydrogen peroxide (H2O2), and the results indicated that the Fe3O4@Au-Pt hybrid nanomaterial possessed preferable peroxidase-like activity in comparison with other nanozyme materials and showing prominent selectivity for glucose detection. For H2O2, the sensor has a linear range of 0.05-120 μM and a relatively low limit of detection (LOD) of 0.018 μM. For glucose, the linear range is 0.05-140 μM with an LOD of 0.025 μM. It is envisioned that these hydrophilic hybrid nanostructures will be widely applied in sensing target analytes, biomedical diagnosis, and therapeutic applications in the future by taking advantage of their specific structure and excellent catalytic performance.
- Bai, Zhenyu,Feng, Xiaoyang,Fu, Hao,Hu, Xueping,Li, Ping,Song, Xingliang
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p. 239 - 249
(2021/12/30)
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- Comparative study on the structural characterization and α-glucosidase inhibitory activity of polysaccharide fractions extracted from Sargassum fusiforme at different pH conditions
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Sargassum fusiforme polysaccharides (SFPs), including SFP-3-40, SFP-3-60, SFP-3-80, SFP-7-40, SFP-7-60, SFP-7-80, SFP-10-40, SFP-10-60, and SFP-10-80, were extracted at different pH (3, 7, and 10), and then precipitated with graded precipitation of 40%, 60% and 80% (v/v) ethanol solution, respectively. Their physicochemical properties and α-glucosidase inhibitory activity were determined. Results showed that SFPs significantly differed in the contents of total sugar, protein, uronic acid, sulfate, the zeta potential, and molecular weight distribution. SFPs, including SFP-10-40, SFP-10-60, and SFP-10-80, had bigger absolute zeta potential value and higher respective average molecular weight in the same ethanol concentration precipitate. All samples were mainly composed of fucose, glucuronic acid, and mannose with different molar ratios. The extraction pH and precipitation ethanol solution concentration caused little changes in functional groups, but significantly altered surface morphology of SFPs. Congo red test revealed that all polysaccharides were not helical polysaccharides. Rheological measurements indicated that SFPs were pseudoplastic fluids and showed elastic behavior of the gel. Except SFP-3-40 and SFP-3-60, all other samples had a stronger α-glucosidase inhibitory activity than that of acarbose. The inhibition type of SFPs against α-glucosidase varied owing to different extraction pH and precipitation ethyl concentration. This study shows that extraction pH can significantly affect the structure and hypoglycemic activity of SFPs and provide a data support for the scientific use of Sargassum fusiforme in industrial production.
- Jia, Rui-Bo,Li, Zhao-Rong,Lin, Lianzhu,Luo, Donghui,Ou, Zhi-Rong,Zhao, Mouming,Zheng, Qianwen
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p. 602 - 610
(2021/11/30)
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- 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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- Triterpene glycosides and phenylpropane derivatives from Staurogyne concinnula possessing anti-angiogenic activity
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After anti-angiogenic activity screening, the potential n-butanol layer partitioned from the ethanol extract of Staurogyne concinnula was conducted. Further purification by Diaion HP20 column and preparative HPLC chromatography, four undescribed triterpen
- Vo, Thanh-Hoa,Lin, Yu-Chi,Liaw, Chia-Ching,Pan, Wen-Pin,Cheng, Jing-Jy,Lee, Ching-Kuo,Kuo, Yao-Haur
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- Triterpenoid saponins from the leaves and stems of Pericampylus glaucus and their insulin mimetic activities
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During an attempt to discover insulin mimetics, thirteen new triterpenoid saponins (1–13), including three phytolaccagenic acids (1, 2, and 12) and ten serjanic acids (3–11 and 13), as aglycones were isolated from a 70% ethanol extract of leaves and stems from Pericampylus glaucus. The chemical structures of compounds 1–13 were determined through spectroscopic data analysis, including NMR, IR, and HRESIMS. All isolated compounds (1–13) were evaluated using 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) as a fluorescent-tagged glucose probe to determine their stimulatory effects on glucose uptake in differentiated 3 T3-L1 adipocyte cells. Consequently, four compounds (4, 7, 11, and 12) exhibited stimulatory effects on glucose uptake.
- Lee, Hee-Ju,Cho, Hyo-Moon,Park, Eun-Jin,Lee, Ba-Wool,Nghiem, Duc-Trong,Pham, Ha-Thanh-Tung,Pan, Cheol-Ho,Oh, Won-Keun
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- A novel acid polysaccharide from Boletus edulis: extraction, characteristics and antitumor activities in vitro
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A novel cold-water-soluble polysaccharide (BEP), with a molecular weight of 6.0 × 106?Da, was isolated from Boletus edulis. BEP consists of galactose, glucose, xylose, mannose, glucuronic, and galacturonic acid in a ratio of 0.34:0.28:0.28:2.57:1.00:0.44. The IR results showed that BEP was an acid polysaccharide, containing α-type and β-type glucoside bonds. MTT assay showed BEP could inhibit cell proliferation significantly. Morphological observation demonstrated that BEP-treated MDA-MB-231 and Ca761 cells exhibited typical apoptotic morphological features. Flow cytometry analysis revealed that BEP caused mitochondrial membrane potential collapse. Annexin V-FITC/PI staining indicated that BEP induced apoptosis of MDA-MB-231 and Ca761 cells through cell block in S phase and G0/G1 phase, respectively. Western blot results showed that BEP could increase the Bax/Bcl-2 ratios, promote the release of cytochrome C, and activate the expression of caspase-3 and caspase-9 in MDA-MB-231 and Ca761 cells. In conclusion, our results demonstrated that BEP could inhibit the proliferation of breast cancer cells and induce apoptosis through mitochondrial pathways.
- Meng, Ting,Yu, Sha-sha,Ji, Hai-yu,Xu, Xiao-meng,Liu, An-jun
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- Chemical constituents from shells of Xanthoceras sorbifolium
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Three undescribed triterpenes and four previously unreported saponins, along with two known ones, were isolated from shells of Xanthoceras sorbifolium (Sapindaceae). Their structures were elucidated by the interpretation of 1D and 2D NMR data. The nitric oxide (NO) assay revealed that 28-O-isobutyryl-21-O-angeloyl-R1-barrigenol and 3-O-β-D-6-O-methylglucuronopyranosyl-21,22-di-O-angeloyl-R1-barrigenol possessed stronger inhibitory effects on LPS-induced NO overproduction (IC50 = 18.5 ± 1.2 and 28.2 ± 1.8 μM, respectively) than the positive drug minocycline (IC50 = 30.1 ± 1.3 μM) in activated BV2 cells. Western blot, RT-qPCR, and docking experiments further validated that the regulation of iNOS and IL-1β expressions was involved in the anti-neuroinflammatory effects of these two compounds.
- Chen, Gang,Xie, Yumeng,Zhou, Di,Yang, Yanqiu,Liu, Jingyu,Hou, Yue,Cheng, Maosheng,Liu, Yang,Li, Ning
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- New olean-15-ene type gymnemic acids from Gymnema sylvestre (Retz.)R.Br. and their antihyperglycemic activity through α-glucosidase inhibition
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A mixture of gymnemic acids was precipitated from the water extract of leaves of Gymnema sylvestre (Retz.)R.Br. ex Sm. (Asclepiadaceae)by acidification with 2 N H2SO4. The chromatographic separation of the mixture afforded five new gymnemic acids (1-5). The compounds were characterized as Δ15 oleanane glycosides on the basis of extensive spectral data analysis. The compounds (1-5)showed dose dependent inhibition of α-glucosidase, which was found to be comparable to acarbose (IC50 95 μg/ml). Maximum inhibition was achieved with compound 4 (IC50 57 μg/ml)followed by 3 (IC50 62 μg/ml), 1 (IC50 80 μg/ml), 2 (IC50 120 μg/ml)and 5 (IC50 128 μg/ml). The results revealed that the overall pattern of hydroxyl and acyl substitutions of compounds affected their inhibitory activity. In oral sucrose tolerance test, pre-treatment with crude gymnemic acid mixture and isolated compounds 1 and 4 at a dose of 10 mg/Kg b.w. significantly blunted the effect of sucrose challenge in mice. Based on these results, the antihyperglycemic effect of G. sylvestre can be, at least partly, attributed to the inhibition of α-glucosidase by its gymnemic acids. The current study provides relatively more direct evidence explaining the effectiveness of G. sylvestre against hyperglycemia.
- Alkefai, Naila Hassan Ali,Amin, Saima,Sharma, Manju,Ahamad, Javed,Mir, Showkat R.
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- Saponins from the roots of Chenopodium bonus-henricus L.
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Two new glycosides of phytolaccagenin and 2β-hydroxyoleanoic acid, namely bonushenricoside A (3) and bonushenricoside B (5) together with four known saponins, respectively compounds 3-O-L-α-arabinopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (1), 3-O-β-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-glucopyranosyl ester (2), 3-O-β-glucuronopyranosyl-bayogenin-28-O-β-glucopyranosyl ester (4) and 3-O-β-glucuronopyranosyl-medicagenic acid-28-β-xylopyranosyl(1→4)-α-rhamnopyranosyl(1→2)-α-arabinopyranosyl ester (6) were isolated from the roots of Chenopodium bonus-henricus L. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, IR and HRMS). The MeOH extract and compounds were tested for cytotoxic activity on five leukemic cell lines (HL-60, SKW-3, Jurkat E6-1, BV-173 and K-562). In addition, the ability of metanolic extract and saponins to modulate the interleukin-2 production in PHA/PMA stimulated Jurkat E6-1 cells was investigated as well.
- Kokanova-Nedialkova, Zlatina,Nedialkov, Paraskev T.,Momekov, Georgi
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p. 2024 - 2031
(2018/06/12)
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- In vivo evaluation and atom-based 3D-QSAR studies on saponins from shells of Xanthoceras sorbifolium Bunge as anti-AD agents
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A series of oleanane type of glycosides (1–19), including nine undescribed ones (1–9), were isolated and identified from Xanthoceras sorbifolium. Subsequently, an atom-based 3D-QSAR model was constructed based on results of the in vivo anti-AD evaluation of the isolates (2–3, 10–17) and nine literature-reported anti-AD oleanane type of glycosides to clarify the structure-anti-AD activity, and under the guidance of which 19 was predicted and proved to elicit a nearly equivalent in vivo anti-AD effect as xanthoceraside and donepezil that were used as positive drugs in the Y maze and Morris water maze test.
- Chen, Gang,Cheng, Maosheng,Li, Ning,Liu, Yang,Xie, Yumeng,Yang, Lei,Zhou, Di,Zou, Libo
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- Quantitative Determination of Pt- Catalyzed d -Glucose Oxidation Products Using 2D NMR
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Quantitative correlative 1H-13C NMR has long been discussed as a potential method for quantifying the components of complex reaction mixtures. Here, we show that quantitative HMBC NMR can be applied to understand the complexity of the catalytic oxidation of glucose to glucaric acid, which is a promising bio-derived precursor to adipic acid, under aqueous aerobic conditions. It is shown through 2D NMR analysis that the product streams of this increasingly studied reaction contain lactone and dilactone derivatives of acid products, including glucaric acid, which are not observable/quantifiable using traditional chromatographic techniques. At 98% glucose conversion, total C6 lactone yield reaches 44%. Furthermore, a study of catalyst stability shows that all Pt catalysts undergo product-mediated chemical leaching. Through catalyst development studies, it is shown that sequestration of leached Pt can be achieved through use of carbon supports.
- Armstrong,Hirayama,Knight,Hutchings
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p. 325 - 335
(2019/01/04)
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- Triterpene Glycosides from the Seeds of Dolichos lablab
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Two new triterpene glycosides (1 and 2), together with nine known triterpene glycosides (3–11), were isolated from the seeds of Dolichos lablab (Leguminosae). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The isolated compounds did not show cytotoxicity against HL-60 human leukemia cells and HepG2 human hepatoma cells at sample concentrations of 20μM.
- Yokosuka, Akihito,Takayama, Hiroki,Mimaki, Yoshihiro
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p. 604 - 608
(2019/07/22)
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- Erythrosaponins A–J, triterpene saponins from the roots and stem bark of Gardenia erythroclada
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Ten undescribed triterpene saponins, named erythrosaponins A–J, along with one known analogue were isolated from the roots and stem bark of Gardenia erythroclada. Their structures were determined on the basis of extensive 1D and 2D NMR analyses. Absolute structure of erythrosaponin A was unequivocally affirmed by single-crystal X-ray crystallography. All isolated compounds were evaluated for their cytotoxicity against cancer cell lines (KB and HeLa S-3) and their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells. Erythrosaponin D showed moderate cytotoxicity against KB and HeLa S-3 cells with IC50 values of 25.8 and 29.5 μM, respectively. Erythrosaponins D, F, G, I and J showed moderate anti-inflammatory with IC50 values in the range of 63.0–81.4 μM.
- Kaennakam, Sutin,Aree, Thammarat,Yahuafai, Jantana,Siripong, Pongpun,Tip-pyang, Santi
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- Structurally diverse glycoconjugated volatile compounds from Oxytropis falcata Bunge
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A phytochemical investigation on the whole plant of Oxytropis falcata Bunge yielded 16 glycoconjugated compounds with structurally diverse volatile aglycones but similar sugars. Of these, five were previously undescribed compounds with different volatile aglycones but same glucuronic acid (1 → 2) glucosyl moiety, including three octanol glucuronic acid (1 → 2) glucosides (1–3), one acyclic monoterpenoid glucuronic acid (1 → 2) glucoside (4), and one 4-phenyl-butan-2-ol glucuronic acid (1 → 2) glucoside (5), and 11 were biological related known glucoconjugated volatile compounds (6–16) isolated from genus Oxytropis for the first time. The structures of these compounds were determined by extensive spectroscopic analysis of MS, 1D and 2D NMR data. The absolute configurations of aglycones and sugar residues were assigned via enzymatic hydrolysis and subsequently comparison of the specific rotations. This is the first report of such structurally diverse glycoconjugated volatile compounds from O. falcata, which might be regarded as the precursor of free volatile compounds, and presents scientific evidences for better clarifying the volatile compositions of this medicinal plant and genus Oxytropis.
- Wang, Shanshan,Zhang, Xiaojing,Que, Sheng,Liang, Hong,Tu, Pengfei,Zhang, Qingying
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p. 143 - 147
(2018/07/29)
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- Saponins from European Licorice Roots (Glycyrrhiza glabra)
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European licorice roots (Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means o
- Schmid, Christian,Dawid, Corinna,Peters, Verena,Hofmann, Thomas
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p. 1734 - 1744
(2018/09/10)
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- Melonoside B and Melonosins A and B, Lipids Containing Multifunctionalized δ-Hydroxy Fatty Acid Amides from the Far Eastern Marine Sponge Melonanchora kobjakovae
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Melonoside B (1) and melonosins B (2) and A (3), new lipids based on polyoxygenated fatty acid amides, and known melonoside A (4) were isolated from two different collections of the marine sponge Melonanchora kobjakovae. The structures of these compounds, including their absolute configurations, were established using detailed analysis of 1D and 2D NMR, ECD, and mass spectra as well as chemical transformations. Melonosins 2 and 3 inhibit AP-1- and NF-kB-dependent transcriptional activities in JB6 Cl41 cells at noncytotoxic concentrations, demonstrating potential cancer preventive activity.
- Guzii, Alla G.,Makarieva, Tatyana N.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Popov, Roman S.,Kuzmich, Alexandra S.,Fedorov, Sergey N.,Krasokhin, Vladimir B.,Kim, Natalya Yu.,Stonik, Valentin A.
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supporting information
p. 2763 - 2767
(2019/01/04)
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- Three new oleanane-type triterpenoid saponins from the seeds of Celosia cristata L.
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Phytochemical investigation of the 1-butanol soluble fraction of 60% ethanol extract of the seeds of Celosia cristata L. led to the identification of three new oleanane-type triterpenoid saponins. Using 1D and 2D NMR experiment metho
- Liu, Xin,Zhang, Jifa,Guo, Kai,Jia, Airong,Zhang, Miansong,Shi, Yaping,Liu, Changheng,Xiao, Linlin,Sun, Zhenliang
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p. 167 - 174
(2017/10/06)
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- Chemical characterization and antioxidant activities of polysaccharides isolated from the stems of Parthenocissus tricuspidata
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Four polysaccharides, PTP–1, PTP–2, PTP–3 and PTP–4, were obtained from the water extraction of the stems of P. tricuspidata by anion exchange chromatography and gel filtration. The antioxidant activities of four PTPs were investigated, exhibiting different antioxidant activities, in which PTP?4 performed noticeable, with strong superoxide radical activity (comparable to BHT), high DPPH radical activity (78.53% at 1250 μg/mL), moderate hydroxyl radical scavenging activity and reducing power activity. Furthermore, the chemical structure of PTP?4 was measured by FT-IR, GC, 1H and 13C NMR spectra, indicating its mainly composition of the arabinose, xylose, galactose, glucuronic acid, and mannose. Thus, the stems of P. tricuspidata could be used as a potential source for natural antioxidant.
- Liang, Xiaoxia,Gao, Yingying,Fei, Wenbo,Zou, Yuanfeng,He, Min,Yin, Lizi,Yuan, Zhixiang,Yin, Zhongqiong,Zhang, Wei
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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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- Cytotoxic triterpene saponins from the mangrove Aegiceras corniculatum
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Using various chromatographic separations, sixteen compounds, including one new triterpene saponin named aegicoroside A (1), were isolated from the leaves of the Vietnamese mangrove Aegiceras corniculatum. Their structures were determined by spectroscopic methods such as 1D and 2D NMR and HR-ESI-MS. The cytotoxic activities of the isolated compounds against MCF7 (breast), HCT116 (colon), B16F10 (melanoma), and A549 (adenocarcinoma) cancer cell lines were also evaluated. Strong cytotoxicity was observed for sakurasosaponin (2) against all four cancer cell lines and for sakurasosaponin methyl ester (3) against MCF7, A549, and HCT116 cell lines with IC50 values ranging from 2.89?±?0.02 to 9.86?±?0.21?μM.
- Vinh, Le Ba,Nguyet, Nguyen Thi Minh,Yang, Seo Young,Kim, Jang Hoon,Thanh, Nguyen Van,Cuong, Nguyen Xuan,Nam, Nguyen Hoai,Minh, Chau Van,Hwang, Inkyu,Kim, Young Ho
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supporting information
p. 1 - 7
(2017/11/23)
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- Phytochemical Characterization of Low Molecular Weight Constituents from Marshmallow Roots (Althaea officinalis) and Inhibiting Effects of the Aqueous Extract on Human Hyaluronidase-1
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Extract RE was obtained from the roots of Althaea officinalis in a yield of 8.1%, related to the dried plant material, by extraction with MeOH-H2O (1:1), followed by precipitation with EtOH to remove high molecular weight constituents. Phytochemical investigation of RE revealed the presence of N-phenylpropenoyl-l-amino acid amides 1-5, 8% glycine betaine 6, about 9% total amino acids with proline as the main compound, and about 61% mono- and oligomeric carbohydrates with sucrose as the main compound. Further fractionation revealed the presence of a hypolaetin diglycoside (12) and four hypolaetin glycosides (7-9 and 11) with O-sulfocarbohydrate moieties; additionally, 4′-O-methylisoscutellarein-8-O-β-d-(3-O-sulfo)glucuronopyranoside (10) and the diglycosylated coumarin haploperoside D (13) were identified. The hypolaetin-O-sulfoglycosides 7-10 are new natural products. RE inhibited the enzymatic activity of surface-displayed human hyaluronidase-1 on Escherichia coli F470 cells with an IC50 of 7.7 mg/mL. RE downregulated mRNA expression of hyal-1 in HaCaT keratinocytes at 125 and 250 μg/mL, respectively. These data contribute to a deeper phytochemical understanding of marshmallow root extracts and to the positive influence of extracts used for therapy of irritated and inflamed buccal tissue and cough.
- Sendker, Jandirk,B?ker, Ines,Lengers, Isabelle,Brandt, Simone,Jose, Joachim,Stark, Timo,Hofmann, Thomas,Fink, Careen,Abdel-Aziz, Heba,Hensel, Andreas
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p. 290 - 297
(2017/03/09)
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- New Triterpenoid Saponins from Green Vegetable Soya Beans and Their Anti-Inflammatory Activities
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Ten compounds were isolated and identified from green vegetable soya beans, of which five are new triterpenoid saponins (1-5) and five are known compounds (6-10). The chemical structures of the five triterpenoid saponins (1-5) were elucidated to be 3β,24-
- Lan, Xiuhua,Deng, Kejun,Zhao, Jianping,Chen, Yiyi,Xin, Xuhui,Liu, Yanli,Khan, Ikhlas A.,Yang, Shilin,Wang, Taoyun,Xu, Qiongming
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p. 11065 - 11072
(2017/12/26)
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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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- Bioactive Iridoid Glycosides from the Whole Plants of Rehmannia chingii
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Nine new iridoid glycosides, rehmachingiiosides A-I (1-9), together with 16 known analogues, were isolated from the whole plants of Rehmannia chingii. The structures of compounds 1-9 were elucidated on the basis of spectroscopic data analysis and from chemical evidence. Furthermore, in two vitro assays, compounds 5 and 10 showed an inhibitory effect on LPS-induced NO production with IC50 values of 2.5 and 7.3 μM, and compounds 4, 6, and 10-12 (when evaluated at 10 μM) exhibited evidence of hepatoprotective effects against APAP-induced HepG2 cell damage.
- Liu, Yan-Fei,Shi, Guo-Ru,Wang, Xin,Zhang, Chun-Lei,Wang, Yan,Chen, Ruo-Yun,Yu, De-Quan
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p. 428 - 433
(2016/03/05)
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- Selective oxidation of glucose to glucuronic acid by cesium-promoted gold nanoparticle catalyst
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Gold catalysts outperform palladium and platinum catalysts for the oxidation of sugars with high activity and selectivity toward aldonic acids. The oxidation into other sugar acids, such as uronic and aldaric acids, has been scarcely investigated. Au nanoparticles supported on CeO2 using a soft chemical reduction method with hydrazine, were active for the selective oxidation of low weight carbohydrates (glucose, fructose, maltose) into glucuronic acid. The oxidation occurred in aqueous solution at low temperature using O2 as oxidant and without adding any base. The activity was improved by modifying the supported Au catalyst with cesium, while selectivity was maintained. Under these conditions, high selectivity to glucuronic acid was achieved; however, in the presence of base many by-products were obtained. The preparation of glucuronic acid in high yield using gold catalysts was never reported, which makes the catalyst developed here very interesting for liquid phase oxidation processes.
- Wojcieszak, Robert,Cuccovia, Iolanda M.,Silva, Márcia A.,Rossi, Liane M.
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- Biological Activities of Oleanolic Acid Derivatives from Calendula officinalis Seeds
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Phytochemical examination of butanol fraction of Calendula officinalis seeds led to the isolation of two compounds identified as 28-O-β-D-glucopyranosyl-oleanolic acid 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosiduronic acid (CS1) and oleanolic acid 3-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranosiduronic acid (CS2). Biological evaluation was carried out for these two compounds such as melanin biosynthesis inhibitory, hyaluronic acid production activities, anti obesity using lipase inhibition and adipocyte differentiation as well as evaluation of the protective effect against hydrogen peroxide induced neurotoxicity in neuro-2A cells. The results showed that, compound CS2 has a melanin biosynthesis stimulatory activity; however, compound CS1 has a potent stimulatory effect for the production of hyaluronic acid on normal human dermal fibroblast from adult (NHDF-Ad). Both compounds did not show any inhibitory effect on both lipase and adipocyte differentiation. Compound CS2 could protect neuro-2A cells and increased cell viability against H2O2. These activities (melanin biosynthesis stimulatory and protective effect against H2O2 of CS2 and hyaluronic acid productive activities of these triterpene derivatives) have been reported for the first time.
- Zaki, Ahmed,Ashour, Ahmed,Mira, Amira,Kishikawa, Asuka,Nakagawa, Toshinori,Zhu, Qinchang,Shimizu, Kuniyoshi
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p. 835 - 841
(2016/05/19)
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- Oleanane-type triterpenoid saponins from Silene armeria
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Twelve triterpenoid saponins, including seven compounds (i.e., armerosides A–G) hitherto unknown, were isolated from whole plants of Silene armeria. Their structures were established based on extensive spectroscopic analyses and chemical methods. From a biosynthetic perspective, C-23 oxidation of the sapogenin appears to be a key factor in the glycosylation pathway.
- Takahashi, Nobuyuki,Li, Wei,Koike, Kazuo
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- Melonoside A: An ω-Glycosylated Fatty Acid Amide from the Far Eastern Marine Sponge Melonanchora kobjakovae
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Melonoside A (1), the first representative of a new class of ω-glycosylated fatty acid amides, was isolated from the Far Eastern marine sponge Melonanchora kobjakovae. The structure of 1, including absolute configuration, was established using detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound 1 induces autophagy of human cisplatin-resistant germinal tumor cells NCCIT-R.
- Guzii, Alla G.,Makarieva, Tatyana N.,Denisenko, Vladimir A.,Dmitrenok, Pavel S.,Kuzmich, Aleksandra S.,Dyshlovoy, Sergey A.,Von Amsberg, Gunhild,Krasokhin, Vladimir B.,Stonik, Valentin A.
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supporting information
p. 3478 - 3481
(2016/07/26)
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- Rearranged oleanane type saponins, astraisoolesaponins A1–A3and B, from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao
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Four novel saponins, astraisoolesaponins A1–A3and B (1–4) were isolated from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. Spectroscopic analysis indicated that 1–4 are the first example of saponins possessing a 28-methyl-rearranged carbon skeleton. Their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Both 3 and 4 displayed triglyceride accumulation inhibitory effects in HepG2 cells and glucose uptake increase effects on L6 cells.
- Zhang, Yi,Guo, Yuan-Qiang,Li, Xiao-Xia,Ruan, Jing-Ya,Wang, Ting-Ting,Li, Jian,Han, Li-Feng,Yu, Hai-Yang,Wang, Tao
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p. 7008 - 7013
(2016/10/14)
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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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- 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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- Acylated oleanane-type triterpene oligoglycosides from the flower buds of Camellia sinensis var. assamica
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Eight new acylated oleanane-type triterpene oligoglycosides, floraassamsaponins I, II, III, IV, V, VI, VII, and VIII, were isolated from the flower buds of Camellia sinensis var. assamica. The chemical structures of new constituents were characterized on
- Ohta, Tomoe,Nakamura, Seikou,Nakashima, Souichi,Matsumoto, Takahiro,Ogawa, Keiko,Fujimoto, Katsuyoshi,Fukaya, Masashi,Yoshikawa, Masayuki,Matsuda, Hisashi
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p. 846 - 851
(2015/01/30)
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- Two new oleanane-type triterpene saponins from the leaves of Schefflera sessiliflora de P. V.
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From the leaves of Schefflera sessiliflora De P. V., two new oleanane-type triterpene saponins, named scheffleraside A (1), scheffleraside B (2); together with two known saponins, chikusetsusaponin IVa (3), 3-O-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl hederagenin (4) were isolated by various chromatography methods. Its chemical structure was elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison of their NMR data with previous reported data.
- Phat, Nguyen Tan,Hoa, Le Thi Viet,Tri, Mai Dinh,Dung, Le Tien,Minh, Phan Nhat,Dat, Bui Trong
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p. 102 - 105
(2015/02/18)
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- Two new penterpenoid saponins and a new diterpenoid glycoside from Hemsleya chinensis
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Two new penterpenoid saponins, hemsloside-Ma4 (1) hemsloside-Ma5 (2), and a new diterpenoid glycoside, hemsloside-Ma6 (3), were isolated from the rhizomes of Hemsleya chinensis. By detailed analysis of the NMR spectra and chemical methods, the structures of new compounds were determined to be 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside (1), 3-O-β-l-arabinopyranosyl-(1 → 3)-O-(6′-methyl ester)-β-d-glucuropyranosyl-oleanolic acid-28-O-β-d-xylopyranosyl-(1 → 6)-O-β-d-glucopy-ranoside (2), and 13ε-hydroxylabda-8(17), 14-dien-18-oic acid-18-O-α-l-rhamnopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-O-α-l-rhamnopyranoside (3). Diterpenoid-type compound (3) was isolated from Hemsleya genus for the first time.
- Song, Na-Li,Li, Zhen-Jie,Chen, Jian-Chao,Deng, Yuan-Yuan,Yu, Mu-Yuan,Zhou, Lin,Qiu, Ming-Hua
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p. 103 - 107
(2015/06/16)
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- Triterpenoid saponins and C-glycosyl flavones from stem bark of Erythrina abyssinica Lam and their cytotoxic effects
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Abstract Six new compounds including two oleanane-type triterpenoid saponins (1, 2) and four C-glycosyl flavones (3-6), along with a known saponin (7), three di-C-glycosyl flavones (8-10) and a glycosyl auronol (11), were isolated from the stem bark of Erythrina abyssinica Lam. The structures of the new compounds, identified as 3-O-[α-l-rhamnopyranosyl-(1 → 2)-β-d-galactopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-22-O-β-d-glucopyranosyl sophoradiol (1), 3-O-[α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 2)-β-d-glucuronopyranosyl]-22-O-β-D-glucopyranosyl sophoradiol (2), 6-C-β-glucopyranosyl-8-C-β-quinovopyranosyl apigenin (3), 6-C-β-quinovopyranosyl-8-C-β-glucopyranosyl apigenin (4), 8-C-[6″-O-α-l-rhamnopyranosyl-(1? → 6″]-β-glucopyranosyl 7,4′-dihydroxyflavone (5) and 8-C-[6″-O-β-d-xylopyranosyl-(1?; → 6″)]-β-glucopyranosyl 7,4′-dihydroxyflavone (6), were determined by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and acid hydrolysis. These new compounds together with the known saponins 7 were evaluated for their cytotoxic activity against MCF-7 (estrogen dependent) and MDA-MB-231 (estrogen independent) cell lines. The new saponin 2 exhibited the highest cytotoxic activity among tested compounds, exerting a selective inhibitory effect against the proliferation of MCF-7 cells, with lower IC50 value (12.90 μM) than that of the positive control, resveratrol (13.91μM). Structure-activity relationship of these compounds is also discussed.
- Pérez, Andy J.,Hassan, Emad M.,Pecio, ?ukasz,Omer, Elsayed A.,Kucinska, Malgorzata,Murias, Marek,Stochmal, Anna
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- Triterpenoid saponins from Aesculus sylvatica W. Bartram
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16 triterpenoid saponins including two new compounds were isolated from the seeds of A esculus sylvatica W. Bartram. The two new saponins were assigned as 3-O-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinofuranosyl-(1 → 3)-β-D-glucuronopyranosyl-21,22-O-ditigloyl-3β,16α,21β,22α,24,28 hexahydroxyolean-12-ene (aesculioside S1, 1) and 3-O-[β-D-glucopyranosyl-(1 → 2)]-α-L-arabinofuranosyl-(1 → 3)-β-D-glucuronopyranosyl-21-O-tigloyl-22-O-angeloyl 3β,16α,21β,22α,24,28-hexahydroxyolean-12-ene (aesculioside S2, 2). Aesculioside S1 and S2 displayed moderate cytotoxicity against human non-small cell lung cancer cells (A549) and prostate cancer cells (PC3) (GI50 ranged from 8.7 to 18.2 μM). The structural analysis of the saponins isolated from Aesculus supports the taxonomic placement of A. sylvatica under the section Pavia of Aesculus genus.
- Yuan, Wei,Wang, Ping,Su, Zushang,Gao, Ruixin,Li, Shiyou
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p. 111 - 114
(2015/10/19)
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- Two triterpenoid glycosides from the roots of Camellia oleifera and their cytotoxic activity
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Two new triterpenoid saponins, oleiferoside N and oleiferoside O, were isolated from the EtOH extract from the roots of Camellia oleifera C. Abel. Their structures were elucidated as 16α-acetoxy-21β,22α-O-diangeloyloxy-23,28-dihydroxyolean-12-ene 3β-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 3)-β-D-glucuronopyranoside (1), 16α-acetoxy-21β-O-angeloyloxy-23,28-dihydroxy-22α-O-(2-methylbutanoyloxy)olean-12-ene 3β-O-β-D-xylopyranosyl-(1 → 3)-α-L-arabinopyranosyl-(1 → 3)-β-D-glucuronopyranoside (2), on the basis of spectroscopic analyses (IR, ESI-MS, HR-ESI-MS, 1D and 2D NMR) and acid hydrolysis. Both were characterized to be oleanane-type saponins with sugar moieties linked to C-3 of the aglycone. Cytotoxic activities of two saponins were evaluated against four human tumor cell lines (A549, B16, BEL-7402, and MCF-7) by using the MTT in vitro assay. Compounds 1 and 2 showed moderate cytotoxic activities toward the tested cell lines.
- Yang, Ping,Li, Xia,Liu, Yan-Li,Xu, Qiong-Ming,Li, Yun-Qiu,Yang, Shi-Lin
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p. 800 - 807
(2015/03/05)
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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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- 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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- 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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- Acylated oleanane-type saponins from Ganophyllum giganteum
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Five oleanane-type saponins, 3-O-β-D-glucuronopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)] -(4-O-acetyl)-β-D-fucopyranosyl ester (1), 3-O-β-D- glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L- rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (2), zanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl- (1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (3), zanhic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′- methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (4), medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′- hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy] -β-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the β-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.
- Montes, Elier Galarraga,Mitaine-Offer, Anne-Claire,Amaro-Luis, Juan Manuel,Paululat, Thomas,Delaude, Clément,Pouységu, Laurent,Quideau, Stéphane,Rojas, Luis B.,Delemasure, Stéphanie,Dutartre, Patrick,Lacaille-Dubois, Marie-Aleth
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p. 236 - 242
(2014/02/14)
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- Effects of polysaccharide on chicks co-infected with Bordetella avium and Avian leukosis virus
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Chicks' co-infection with immunosuppressive virus and bacteria seriously threaten the development of the poultry industry. In this study, a model was established in which chicks were injected with either subgroup B ALV (ALV-B) + Bordetella avium (B. avium), or ALV-B + B. avium + Taishan Pinus massoniana pollen polysaccharide (TPPPS), or B. avium only, or B. avium + TPPPS. The data showed that the group injected with ALV-B and B. avium exhibited significant inhibition of the immune function and therefore increased pathogenicity compared with the group injected with B. avium-only. Application of TPPPS effectively alleviated immunosuppression, and body weights increased sharply in the TPPPS groups compared with non-TPPPS groups. To some extent, TPPPS may reduce the proliferation of ALV-B. These results suggest that Pinus pollen polysaccharides are beneficial treating co-infections with immunosuppressive virus and bacteria and therefore have potential for development into safe and effective immunoregulator.
- Guo, Fanxia,Xue, Cong,Wu, Cun,Zhao, Xue,Qu, Tinghe,He, Xiaohua,Guo, Zhongkun,Zhu, Ruiliang
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- Identification of two new phenathrenones and a saponin as antiprotozoal constituents of Drypetes gerrardii
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In an in vitro screen of 206 extracts from South African plants, the CH2Cl2/MeOH (1:1) stem extract of Drypetes gerrardii Hutch. var gerrardii (Putranjivaceae) inhibited Plasmodium falciparum and Leishmania donovani (IC50s of 0.50 and 7.31 μg/ml, respectively). In addition, the CH2Cl2/MeOH (1:1) extract of the leaves showed activity against Trypanosoma brucei rhodesiense (IC50 of 12.1 μg/ml). The active constituents were tracked by HPLC-based activity profiling, and isolated by preparative and semi-preparative RP-HPLC chromatography. Their structures were established by HRESIMS, and 1D and 2D NMR (1H, 13C, COSY, HMBC, HSQC, and NOESY). From the stem extract, a new phenanthrenone derivative, drypetenone D (1), and a phenanthrenone heterodimer, drypetenone E (2), were isolated. Compound 1 showed potent in vitro activity against P. falciparum (IC50 of 0.9 μM) with a selectivity index (SI) of 71, as calculated from cytotoxicity data for L-6 cells. These data qualified 1 for in vivo assessment in the Plasmodium berghei mouse model, but the compound turned out to be inactive. Compound 2 also exhibited good in vitro antiplasmodial activity (IC50 of 2.0 μM) and selectivity (SI 31). From the leaf extract, the saponin putranoside A (3) was isolated and identified. Compound 3 showed weak in vitro trypanocidal activity, with an IC50 of 18.0 μM, and a SI of 4.
- Hata, Yoshie,De Mieri, Maria,Ebrahimi, Samad Nejad,Mokoka, Tsholofelo,Fouche, Gerda,Kaiser, Marcel,Brun, Reto,Potterat, Olivier,Hamburger, Matthias
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supporting information
p. cxl
(2015/04/16)
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- New oleanane-type triterpenoid saponins isolated from the seeds of Celosia argentea
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Three new oleanane-type triterpenoid saponins named celosins H (1), I (2), and J (3) were isolated from the seeds of Celosia argentea L. Their structures were characterized as 3-O-β-d-xylopyranosyl-(1 → 3)-β-d- glucuronopyranosyl-polygalagenin 28-O-β-d-gl
- Pang, Xu,Yan, Hai-Xia,Wang, Zhen-Fang,Fan, Miao-Xuan,Zhao, Yang,Fu, Xin-Tong,Xiong, Cheng-Qi,Zhang, Jie,Ma, Bai-Ping,Guo, Hong-Zhu
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p. 240 - 247
(2014/02/14)
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