- 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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- 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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- Catalytic wet air oxidation of D-glucose by perovskite type oxides (Fe, Co, Mn) for the synthesis of value-added chemicals
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The conversion of common biomasses derived, as D-glucose, into value-added chemicals has received highest attention in the last few years. Among all processes, the catalytic wet air oxidation (CWAO) of derived biomasses using noble metal-based heterogeneo
- Geobaldo, Francesco,Pirone, Raffaele,Russo, Nunzio,Scelfo, Simone
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- Chain conformations and steady-shear viscosity properties of pectic polysaccharides from apple and tomato
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In this study, apple pectin (AP) and tomato pectin (TP) were demonstrated to be a high-ester (74.8%) polysaccharide with the weight-average molecular weight (Mw) of ～ 243 kDa and a low-ester (45.9%) polysaccharide with the Mw of ～ 19 kDa, respectively. The semi-rigid chain conformations of pectic polysaccharides in NaNO3 aqueous solution were deduced according to the Smidsr?d “B values” of AP (0.025) and TP (0.029), while AP and TP exhibited higher stiffness in water due to the electric repulsion of carboxyl groups, which was visually observed by AFM images. Under steady shear, the shear-thickening behaviors of AP and TP in NaNO3 aqueous solutions were observed in the shear rate range of ?1, which were attributed to the disruption of the ordered arrangement induced by semi-rigid pectin chains into randomly entangled structure by weak shear force. AP exhibited stronger shear-thickening behavior due to the formation of more entanglements resulted from the higher Mw and longer side chains highly branched at rhamngalacturonan region. This study provides the scientific basis for the construction of the relationship of steady-shear property with chain conformation and molecular weight of pectin.
- Hu, Shihao,Nie, Shaoping,Wang, Junqiao,Wang, Qiang,Xu, Xiaojuan
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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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- 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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- 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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- Oleanane-type triterpene saponins from Aralia armata leaves and their cytotoxic activity
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Two new, aramatosides A and B (1 and 2), together with seven known oleanane-type triterpene saponins (3–9) were isolated from the leaves of Aralia armata. Their structures were determined by combination of HR-ESI-MS, 1 D and 2 D NMR spectral data as well as comparison with the previous literature. Compounds 6–9 exhibited cytotoxic effects towards three human cancer cell lines (HT29, A2058, and A549) with IC50 values ranging from 2.01 ± 0.17 to 18.8 ± 1.17 μM. Especially, compound 7 (narcissiflorin) showed significant cytotoxic activity against HT29 and A549 cell lines with IC50 values of 2.02 ± 1.65 and 2.01 ± 0.17 μM, respectively, which are smaller than those of positive control irinotecan hydrochloride (IC50 values of 10.3 ± 1.32 and 9.89 ± 0.19 μM).
- Yen, Pham Hai,Chuong, Nguyen Th? Hong,Lien, Giang Thi Kim,Cuc, Nguyen Thi,Nhiem, Nguyen Xuan,Thanh, Nguyen Thi Viet,Tai, Bui Huu,Seo, Yohan,Namkung, Wan,Park, SeonJu,Kim, Seung Hyun,Minh, Chau Van,Kiem, Phan Van
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supporting information
p. 142 - 149
(2020/06/03)
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- A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
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The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.
- Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
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- PROCESSES FOR PREPARING ALDARIC, ALDONIC, AND URONIC ACIDS
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Various processes for preparing aldaric acids, aldonic acids, uronic acids, and/or lactone(s) thereof are described. For example, processes for preparing a C2-C7 aldaric acid and/or lactone(s) thereof by the catalytic oxidation of a C2-C7 aldonic acid and/or lactone(s) thereof and/or a C2-C7 aldose are described.
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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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- Novel polysaccharide from Chaenomeles speciosa seeds: Structural characterization, α-amylase and α-glucosidase inhibitory activity evaluation
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Purification and structural characterization of a novel polysaccharide fraction from Chaenomeles speciosa seeds were investigated. After hot water extraction and ethanol precipitation, the crude polysaccharide was sequentially purified with Cellulose DEAE-52 and gel-filtration chromatography, and a highly purified polysaccharide fraction (F3) was obtained. The structure of F3 was characterized by high-performance gel permeation chromatography (HPGPC), high performance liquid chromatography (HPLC), ultraviolet-visible (UV), Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectrum, together with methylation, scanning electron microscopy (SEM), atomic force microscope (AFM), and Congo-red test analysis. The results indicated that F3 was a homogeneous polysaccharide fraction with a molecular weight of 8.65 × 106 Da, and it was composed of Rha, GlcA, Gal, and Ara in a molar ratio of 6.34:5.73:47.14:40.13. The backbone of F3 was consisted of →3,6)-Galp-(1→, and the side chains of F3 were composed of Araf-(1→, →4)-GlcpA-(1→, →4)-Galp-(1→ and →3)-Rhap-(1→. The hypoglycemic assays demonstrated F3 had good α-amylase and α-glucosidase inhibition activities, and their IC50 values were 6.24 mg/mL and 4.59 mg/mL respectively. Thus, the polysaccharide from Chaenomeles speciose could be applied as a potential natural source in retarding postprandial hyperglycemia effects.
- Cheng, Jiang,Deng, Yejun,Huang, Lixin,Liu, Lujie,Wang, Xiang,Xie, Pujun,Zhang, Caihong
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p. 755 - 766
(2020/03/18)
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- Symplocosins C-P: Fourteen triterpene saponins from the leaves of symplocos cochinchinensis var. philippinensis
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Extensive phytochemical work on the 1-BuOH-soluble fraction of a MeOH extract of the leaves of Symplocos cochinchinensis var. philippinensis resulted in the isolation of 14 new triterpenene saponins, along with four known ones. Their structures were elucidated by comparison of NMR spectroscopic data with related compounds reported in the literature. Three oleanane-type saponins, symplocosins K, M, and P, possessed glucuronic acid as a sugar component, and their carboxyl groups appeared as methyl esters. These are probably formed during extraction and isolation procedures. Symplocosin K (9) showed moderate cytotoxicity toward A549 cells. In addition, all isolated compounds did not show α-glucosidase inhibitory activity.
- Ohyama, Nobuhiro,Cai, Wen-Hu,Kawakami, Susumu,Sugimoto, Sachiko,Matsunami, Katsuyoshi,Otsuka, Hideaki
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p. 1090 - 1099
(2020/11/26)
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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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- 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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- 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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- 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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- 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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- 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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- 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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- 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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- 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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- 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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- 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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- A cytotoxic flavonol glycoside from Melaleuca leucadendra leaves extract with immunostimulant activity
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Leaves of Melaleuca leucadendra contain the novel flavonol glycoside, myricetin 3-O-β-4C1-galactopyranuronoid. In addition, known fifteen phenolics were identified. All isolates are characterized for the first time from this plant. Structures were established by conventional methods and confirmed by spectral methods of analysis, including one and two-dimensional nuclear magnetic resonance spectroscopy (1D and 2D-NMR) and high resolution electro-spray ionization mass spectrometry (HRESIMS), as well. Assessment of some immunological and biological efficacy, of the extract in combination with a parallel cytotoxicity evaluation, using the method of cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) technique was carried out. Besides, evaluation of the antioxidant effectiveness, using the free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and the oxygen radical absorption capacity (ORAC) methods was performed. In addition, the cytotoxicity against liver (Huh-7), breast (MCF-7) and prostate (PC-3) cancers using the neutral red assay (NRU) technique for the extract and the new flavonol glycoside also, was assessed.
- Hashim,Swilam,Moustafa,Bakry,Labib,Barakat,Singab,Linscheid,Nawwar
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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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- 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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- 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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- Purification, characterization, and bioactivities of a polysaccharide from mycelial fermentation of Bjerkandera fumosa
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In this work, a novel polysaccharide (named DBFM3) was isolated from mycelia of Bjerkandera fumosa by DEAE-32 and Sepharose CL–6?B column chromatography. High-performance gel permeation chromatography showed that DBFM3 was homogeneous, with an average molecular weight of 1.8?×?105?Da. Structural characteristics of the purified fraction were investigated by high-performance liquid chromatography (HPLC), FT-IR, and NMR. HPLC analysis indicated that DBFM3 was composed of mannose, galacturonic acid, and galactose at molar ratios of 1:18.16:0.702. Spectral analysis suggested that DBFM3 had (1?→?6), (1?→?3,6), (1?→?3) linkages and pyranose conformation. Antioxidant assay in vitro showed that DBFM3 exhibited 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical scavenging activity, and has protective effect against DNA damage and damage to SH-SY5Y cells induced by H2O2. Immunological tests indicated that DBFM3 significantly increased lymphocyte proliferation in vitro. Furthermore, DBFM3 increased the proliferation of lymphocytes in the presence of concanavalin A or lipopolysaccharide as mitogen.
- Liu, Di,Sun, Qianwen,Xu, Jing,Li, Na,Lin, Jianan,Chen, Shan,Li, Fan
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p. 115 - 122
(2017/03/23)
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- Triterpenoids with Antiplatelet Aggregation Activity from the Roots of Ilex pubescens
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Two new triterpenes and five new triterpene saponins, named ilexpusons A-G (1 - 7), as well as eight known compounds were isolated from Ilex pubescens. The structures of the new compounds were established by a combination of chemical and spectroscopic methods, including HRESIMS, 1 H-NMR, 13 C-NMR, 1 H- 1 H COSY, HSQC, HMBC, and NOESY. Additionally, the biological activity of compounds 1 - 15 against adenosine diphosphate-induced platelet aggregation in rabbit plasma was determined. Among the tested compounds, 1, 2, 5, 6, 8, 13, 14, and 15 exhibited significant inhibition of platelet aggregation in vitro.
- Tan, Qinglong,Qiu, Maosong,Cao, Di,Xiong, Tianqin,Zhang, Lei,Zhou, Lian,Rong, Li,Zhou, Jinsong,Jin, Jing,Zhao, Zhongxiang
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p. 797 - 804
(2017/06/19)
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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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- 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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- 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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- 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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- 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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- Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d -Gulose, 6-Deoxy- d -gulose, l -Glucose, 6-Deoxy- l -glucose, and Related Sugars
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Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: meso-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses.
- Liu, Zilei,Yoshihara, Akihide,Jenkinson, Sarah F.,Wormald, Mark R.,Estévez, Ramón J.,Fleet, George W.J.,Izumori, Ken
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p. 4112 - 4115
(2016/08/30)
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- METHOD FOR HYDROLYSIS OF ALGINATE
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Provided is a method for decomposing alginate. The method for decomposing alginate comprises a step of conducting a decomposition reaction of alginate using a solid acid catalyst in water. The solid acid catalyst is a carbon catalyst having a sulfonic acid functional group. According to an embodiment of the present invention, alginate can be decomposed in an environment-friendly way without using sulfuric acid. Also, mannuronic acid and guluronic acid are formed by the decomposition of alginate.
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Paragraph 0035-0037; 0039; 0041
(2017/09/26)
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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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- 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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- 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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- 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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- 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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- 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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- Five new triterpenoid saponins from the Roots of Camellia oleifera C. Abel with cytotoxic activities
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Abstract Five new triterpenoid saponins, oleiferosides P-T (1-5) were isolated from the EtOH extract of the roots of Camellia oleifera C. Abel. The structures of saponins 1-5 were elucidated on the basis of integrated spectroscopic techniques. All the compounds were characterized to be oleanane-type saponins with sugar moieties linked to the C-3 of the aglycone. By using the MTT assay, an in vitro analysis of the cytotoxic activities of these saponins on the human tumor cell lines (lung adenocarcinoma A549 cells, hepatic carcinoma SMMC-7721 cells and breast cancer MCF-7 cells). Among them, compound 4 showed a certain cytotoxic activity against all the tested cell lines.
- Wu, Jiangping,Zhao, Jianping,Liu, Yanli,Li, Xiaoran,Xu, Qiongming,Feng, Yulin,Khan, Ikhlas A.,Yang, Shilin
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p. 379 - 385
(2015/08/24)
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- Dhasingreoside: New flavonoid from the stems and leaves of Gaultheria fragrantissima
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A new flavonoid, dhasingreoside (1) and seven known compounds, quercetin 3-O-β-d-galacturonopyranoside (2), quercetin 3-O-β-d-galactopyranoside (3), quercetin 3-O-β-d-glucuronopyranoside (4), quercetin 3-O-α-l-rhamnopyranoside (5), (-)-epicatechin (6), salicylic acid (7) and gaultherin (8), have been isolated from the shade-dried stems and leaves of Gaultheria fragrantissima, commonly known as Dhasingre in Nepal. The structures were elucidated on the basis of physical, chemical and spectroscopic methods. Among known compounds, five compounds (3-6 and 8) were isolated for the first time from G. fragrantissima. In vitro antioxidant activity of all the isolated compounds was evaluated by 1,1-diphenyl-2-picrylhydrazyl free radical-scavenging assay. Dhasingreoside (1) and other compounds (2-6) showed significant free radical-scavenging activity.
- Cong, Fei,Joshi, Khem Raj,Devkota, Hari Prasad,Watanabe, Takashi,Yahara, Shoji
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p. 1442 - 1448
(2015/03/05)
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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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- 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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- Constituents of Vigna angularis and their in vitro anti-inflammatory activity
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Nine non-phenolic compounds, including four furanylmethyl glycosides, angularides A-D, one ent-kaurane diterpene glycoside, angularin A, and four triterpenoid saponins, angulasaponins A-D, were isolated from seeds of Vigna angularis, together with eight known compounds. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic analysis as well as chemical methods. Angularin A, angulasaponins A-C, and azukisaponins III and VI showed inhibition of nitric oxide production in LPS-activated RAW264.7 macrophages, with IC50 values ranging from 13 μM to 24 μM.
- Jiang, Yong,Zeng, Ke-Wu,David, Bruno,Massiot, Georges
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p. 111 - 118
(2015/02/19)
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