- Hydrolysis of β-galactosyl ester linkage by β-galactosidases
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p-Hydroxybenzoyl β-galactose (pHB-Gal) was synthesized chemically to examine the hydrolytic activity of β-galactosyl ester linkage by β-galactosidases. The enzyme from Penicillium multicolor hydrolyzed the substrate as fast as p-nitrophenyl β-galactoside (pNP-Gal), a usual substrate with a β-galactosidic linkage. The enzymes from Escherichia coli and Aspergillus oryzae hydrolyzed pHB-Gal with almost the same rates as pNP-Gal. The enzymes from Bacillus circulans, Saccharomyces fragilis, and bovine liver showed much lower activities. pH-activity profiles, inhibition analysis, and kinetic properties of the enzymic reaction on pHB-Gal suggested that β-galactosidase had only one active site for hydrolysis of both galactosyl ester and galactoside. The Penicillium enzyme hydrolyzed pHB-Gal in the presence of H218O to liberate galactose containing 18O. This result suggests the degradation occurs between the anomeric carbon and an adjacent O atom in the ester linkage of pHB-Gal.
- Kiso, Taro,Nakano, Hirofumi,Nakajima, Hirofumi,Terai, Tadamasa,Okamoto, Katsuyuki,Kitahata, Sumio
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- Cooperation of β-galactosidase and β-N-acetylhexosaminidase from bifidobacteria in assimilation of human milk oligosaccharides with type 2 structure
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Bifidobacteria are predominant in the intestines of breast-fed infants and offer health benefits to the host. Human milk oligosaccharides (HMOs) are considered to be one of the most important growth factors for intestinal bifidobacteria. HMOs contain two
- Miwa, Mika,Horimoto, Tomohiro,Kiyohara, Masashi,Katayama, Takane,Kitaoka, Motomitsu,Ashida, Hisashi,Yamamoto, Kenji
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- SBA-15 supported ionic liquid phase (SILP) with H2PW12O40- for the hydrolytic catalysis of red macroalgal biomass to sugars
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A supported ionic liquid phase (SILP) catalyst for biomass hydrolysis was prepared via immobilization of an acidic ionic liquid (IL) with a phosphotungstic counter-anion H2PW12O40- (HPW) on ordered mesoporous silica (SBA-15). Characterization results from XRD, N2 physisorption, FT-IR, TGA and SEM/TEM image analyses confirmed the successful preparation of the SILP catalyst (SBA-IL-HPW). Meanwhile, its catalytic performance was evaluated in terms of sugar production from the hydrolysis of different biomasses in water. Under optimal hydrolysis conditions, SBA-IL-HPW yielded 73% d-galactose from agarose and 58% d-glucose from cellobiose. Moreover, SBA-IL-HPW effectively hydrolyzed the red macroalgae G. amansii as it afforded 55% total reducing sugar and 38% d-galactose yields. SBA-IL-HPW was easily separated from the hydrolysates after reaction and was re-used five times without significant loss of activity. Overall findings reveal the potential of SBA-IL-HPW as a durable, environmentally benign catalyst for sugar production from renewable resources.
- Malihan, Lenny B.,Nisola, Grace M.,Mittal, Neha,Lee, Seong-Poong,Seo, Jeong Gil,Kim, Hern,Chung, Wook-Jin
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- Purification and characterization of two novel β-galactosidases from Lactobacillus reuteri
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The intracellular β-galactosidase (β-gal) enzymes from two strains of Lactobacillus reuteri, L103 and L461, were purified by ammonium sulfate fractionation, hydrophobic interaction, and affinity chromatography. Both enzymes are heterodimers with a molecular mass of 105 kDa, consisting of a 35 kDa subunit and a 72 kDa subunit. Active staining of L. reuteri L103 and L461 β-gal with 4-methylumbelliferyl β-D-galactoside showed that the intact enzymes as well as the larger subunits possess β-galactosidase activity. The isoelectric points of L. reuteri L461 and L103 β-gal were found to be in the range of 3.8-4.0 and 4.6-4.8, respectively. Both enzymes are most active in the pH range of 6-8; however, they are not stable at pH 8. The L. reuteri β-galactosidases are activated by various mono- and divalent cations, including Na+, K+, and Mn2+, and are moderately inhibited by their reaction products D-glucose and D-galactose. Because of their origin from beneficial and potentially probiotic lactobacilli, these enzymes could be of interest for the synthesis of prebiotic galactooligosaccharides.
- Nguyen, Thu-Ha,Splechtna, Barbara,Steinboeck, Marlene,Kneifel, Wolfgang,Lettner, Hans Peter,Kulbe, Klaus D.,Haltrich, Dietmar
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- Adxanthromycins A and B, new inhibitors of ICAM-1/LFA-1 mediated cell adhesion molecule from streptomyces sp. NA-148. II. Physico-chemical properties and structure elucidation
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Adxanthromycins A and B are new inhibitors of ICAM-1/LFA-1 mediated cell adhesion molecule isolated from the fermentation broth of Streptomyces sp. NA-148. The molecular formula of adxanthromycins A and B were determined as C42H40O17 and C48H50O22, respectively by FAB-MS and NMR spectral analyses, and the structures of both compounds were elucidated to be a dimeric anthrone peroxide skeleton containing α-D-galactose by various NMR spectral analyses and chemical degradation.
- Takahashi, Senji,Nakano, Takayuki,Koiwa, Tsukasa,Noshita, Toshiro,Funayama, Shinji,Koshino, Hiroyuki,Nakagawa, Akira
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- Depsitinuside: A new depside galactoside from an endophytic fungus isolated from Viburnum tinus
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Chromatographic purification of the extract of an endophytic fungal culture yielded depsitinuside (1), a new phenolic ester together with ergosterol (2) and (22E,24S)-24-methyl-5-a-cholesta-7,22-diene-3b,5,6b-triol (3). The structure of 1 was elucidated based on 1D, 2D NMR spectroscopy and high-resolution mass spectrometry, whereas the known compounds (2 and 3) were identified by 1H NMR, mass spectrometry, and in comparison with the literature values. Compound 1 was evaluated for its enzyme inhibitory potential against acetylcholinesterase, butyrylcholinesterase and lipoxygenase, and was found inactive (10%-40% inhibition at a concentration of 2 mg/ml).
- Nazir, Mamona,Sultan, Misbah,Riaz, Naheed,Hafeez, Maria,Hussain, Hidayat,Ahmed, Ishtiaq,Schulz, Barbara,Draeger, Siegfried,Jabbar, Abdul,Krohn, Karsten,Ashraf, Muhammad,Saleem, Muhammad
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- An unusual galactofuranose lipopolysaccharide that ensures the intracellular survival of toxin-producing bacteria in their fungal host
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Dress code for living in a fungus: Analysis of the carbohydrate coating of the toxin-producing endobacterium of the phytopathogenic fungus Rhizopus microsporus revealed an unprecedented lipopolysaccharide (LPS) structure, which is important for infection and colonization of the fungal host. A mutant lacking the unusual [→2)-β-D-galactofuranose-(1→]n O antigen (red in the schematic illustration) was incapable of forming a stable symbiosis with the fungus.
- Leone, Maria R.,Lackner, Gerald,Silipo, Alba,Lanzetta, Rosa,Molinaro, Antonio,Hertweck, Christian
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- Polyphenols from Euphorbia pekinensis Inhibit AGEs Formation in Vitro and Vessel Dilation in Larval Zebrafish in Vivo
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To identify active compounds in the roots of Euphorbia pekinensis for treatment of diabetic complications, an active column fraction from a 70% EtOH extract of E. pekinensis root was purified by preparative reversed-phase high-performance liquid chromatography, leading to the isolation of a new ellagic acid derivative, 3,3′-di- O -methylellagic acid 4- O -(6- O -galloyl)- β -D-galactopyranoside (1), along with three known compounds, geraniin (2), 3,3′-di- O -methylellagic acid 4- O - β -D-xylopyranoside (3), and ellagic acid 3,3′-dimethyl ether (4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The inhibitory effects of isolated compounds 1 - 4 on advanced glycation end-products (AGEs) formation were examined. All compounds exhibited considerable inhibition of AGEs formation and IC 50 values of 0.41 - 12.33 μM, compared with those of the positive controls aminoguanidine (IC 50 = 1122.34 μM) and quercetin (IC 50 = 27.80 μM). In addition, the effects of 2 and 4 on the dilation of hyaloid-retinal vessels induced by high glucose (HG) in larval zebrafish were investigated; both compounds significantly reduced the HG-induced dilation of hyaloid-retinal vessels relative to the HG-treated control group.
- Lee, Ik-Soo,Jung, Seung-Hyun,Kim, Jin Sook
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- Cyclotanoside, a New Cycloartane Glycoside from Flowers of Astragalus tanae
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The new cycloartane glycoside cyclotanoside and the triterpene saponin astragaloside VIII were isolated from flowers of Astragalus tanae Sosn. Their structures were established as 9β,19-cyclolanost-12,24E-dien-1α,3β,6α,16β,27-pentaol-27-O-β-D-(6′-O-acetoxy)-galactopyranoside and 3-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-xylopyranosyl-(1→2)-O-β-D-glucuronopyranosyl-soyasapogenol B.
- Alaniya,Kavtaradze, N. Sh.,Skhirtladze,Aneli
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- Structural and serological studies on the O-antigen show that Citrobacter youngae PCM 1505 must be classified to a new Citrobacter O-serogroup
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The O-polysaccharide obtained by mild acid hydrolysis of the lipopolysaccharide of Citrobacter youngae PCM 1505 was studied by sugar and methylation analyses along with 1D and 2D 1H and 13C NMR spectroscopies. The following structure of the tetrasaccharide repeating unit of the polysaccharide was established: Structural and serological data obtained earlier and in this work show that the strain studied is a candidate to a new Citrobacter O-serogroup.
- Katzenellenbogen, Ewa,Kocharova, Nina A.,Gorska-Fraczek, Sabina,Gamian, Andrzej,Shashkov, Alexander S.,Knirel, Yuriy A.
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- Substrate specificity and other properties of the beta-D-galactosidase from Aspergillus niger.
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beta-D-Galactosidase from Aspergillus niger was purified by conventional techniques, including the repeated use of chromatography on hydroxylapatite. The final preparation represented a 112-fold purification, with a 22% yield. The specific activity of the purified enzyme was 72 mumol of D-galactose released/min/mg of protein, using p-nitrophenyl beta-D-galactopyranoside as the substrate. The substrate specificity of the enzyme was studied by using saccharides having structural linkages similar to those found in naturally occurring glycoconjugates. At substrate concentrations of 5mM, the beta-D-galactosidase efficiently hydrolyzed beta-Gal-1 leads to OC6H4NO2-p, beta-Gal-(1 leads to 3)-Gal, beta-Gal-(1 leads to 3)-beta-Gal-1 leads to OC6H4NO2-p, and beta-Gal-(1 leads to 3)-alpha-Gal-1 leads to OC6H4NO2-p, at rates of 63, 53, 65, and 29 mumol/min/mg of protein, respectively. Slower hydrolysis was observed for beta-Gal-(1 leads to 4)-beta-Glc, beta-Gal-(1 leads to 4)-beta-GlcNAc-1 leads to OC6H4NO2-p, and beta-Gal-(1 leads to 6)-beta-GlcNAc-1 leads to OC6H4NO2-p, with rates of 10, 13 and 9 mumol/min/mg of protein, respectively. Poorly hydrolyzed, at rates 1/300th of that of beta-Gal-1 leads to OC6H4NO2-p, were synthetic substrates having D-galactose attached beta-(1 leads to 3)- to either GalNAc or GlcNAc. The Km value for beta-D-galactosidase with beta-Gal-(1 leads to 4)-beta-GlNAc-1 leads to OC6H4NO2-p was approximately 20 times that with beta-Gal-1 leads to OC6H4NO2-p. The beta-D-galactosidase of A. niger has a molecular weight of 300,000, as demonstrated by gel-filtration chromatography. Sodium dodecyl sulfate-poly(acrylamide)-gel electrophoresis indicated a single subunit having a molecular weight of 130,000.
- Sykes,Abbas,Barlow,Matta
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- Structural analysis of kappa-carrageenan isolated from Hypnea musciformis (red algae) and evaluation as an elicitor of plant defense mechanism
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High molecular weight crude and purified polysaccharide fractions obtained from Hypnea musciformis, red algae were evaluated for their elicitor activity in terms of induced browning and phytoalexins production in the cotyledons of Chickpea and Peas. Intense browning was performed from purified fraction of algae that was extracted with water, dilute alkali and acid for elicitor preparations and maximum yield (30.2%) was obtained in aqueous extraction. Chemical composition of these extracted polysaccharides in terms of total sugar, protein, sulfate and uronic acid was performed and found that purified fractions contained sugar content (67.6%) and galactose as a major sugar component. using. Gel Permeation Chromatography of purified fraction identified molecular range ≥70,000 Da. On the basis of FTIR, 1H and 13C NMR studies, the purified fraction was safely characterized as k-carrageenan.
- Arman, Muhammad,Qader, Shah Ali Ul
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- Two new cucurbitane triterpenoids from the seeds of Momordica charantia
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Two new cucurbitane triterpenoids 1 and 2 were isolated, together with six known compounds, from the seeds of Momordica charantia L. The structures of new compounds were determined to be 3-O-{[β-d-galactopyranosyl(1 → 6)]-O-β-d-galactopyranosyl}-23(R), 24
- Ma, Lin,Yu, Ai-Hua,Sun, Li-Li,Gao, Wan,Zhang, Meng-Meng,Su, Ya-Lun,Liu, Hua,Ji, Teng-Fei,Li, Di-Zao
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- Houttuynoid M, an Anti-HSV Active Houttuynoid from Houttuynia cordata Featuring a Bis-houttuynin Chain Tethered to a Flavonoid Core
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Houttuynoid M (1), a new houttuynoid, and the related known compound houttuynoid A (2) were isolated from Houttuynia cordata. Their structures were defined using NMR data analysis, HR-MSn experiment, and chemical derivatization. Houttuynoid M is the first example of a houttuynoid with a bis-houttuynin chain tethered to a flavonoid core. A putative biosynthetic pathway of houttuynoid M (1) is proposed. The anti-herpes simplex virus (anti-HSV) activities of 1 and 2 (IC50 values of 17.72 and 12.42 μM, respectively) were evaluated using a plaque formation assay with acyclovir as the positive control.
- Li, Jiao-Jiao,Chen, Guo-Dong,Fan, Hong-Xia,Hu, Dan,Zhou, Zheng-Qun,Lan, Kang-Hua,Zhang, Hui-Ping,Maeda, Hideaki,Yao, Xin-Sheng,Gao, Hao
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- Modulating the site-specific oral delivery of sorafenib using sugar-grafted nanoparticles for hepatocellular carcinoma treatment
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Globally, one in six deaths is reported due to cancer suggesting the critical need for development of advanced treatment regimens. In this study, solid lipid nanoparticles (SLN) were prepared and appended with polyethylene glycol (PEGylated) galactose and a multikinase inhibitor sorafenib (SRFB) was used as chemotherapeutic drug, for treating hepatocellular carcinoma (HCC). The nanoparticles were evaluated for in-vitro and in-vivo performances to showcase the targeting efficiency and therapeutic benefits of the sorafenib loaded ligand conjugated nanoparticles (GAL-SSLN). When compared with SRFB or Sorafenib loaded SLN, GAL-SSLN showed superior cytotoxicity and apoptosis in HepG2 (human hepatocellular carcinoma cells). In addition, in-vivo pharmacokinetics and real time biodistribution studies in BALB/c mice showed that the surface conjugation of nanoparticles with galactose resulted in better pharmacokinetic performance and targeted delivery of the nanoparticles to liver. Results indicated that GAL-SSLN showed promising attributes in terms of targeting sorafenib to liver and therapeutic efficacy.
- Tunki, Lakshmi,Kulhari, Hitesh,Vadithe, Lakshma Nayak,Kuncha, Madhusudana,Bhargava, Suresh,Pooja, Deep,Sistla, Ramakrishna
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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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- 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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- Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
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The phytochemical investigations of the seeds of Digitalis purpurea have revealed their richness in cardenolide and pregnane glycosides exhibiting potent cytotoxicity; further chemical examinations of the D. purpurea seeds have achieved the isolation of s
- Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
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- Two new steroidal alkaloids from the mature fruits of Solanum nigrum
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Two previously undescribed steroidal alkaloids, compounds 1–2, were isolated from the ripe fruits of Solanum nigrum, along with seven known metabolites (3–9). Based on spectroscopic and chemical evidence, including IR, NMR, and HR-ESI-MS analyses, the structures of the isolated compounds were elucidated as 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3)]-β-D-galacopyranoside and 12β-hydroxy-(3β,22α,25R)-spirosol-5-en-27-acid-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside. Four steroidal alkaloids (compounds 1–2 and 4–5) were tested for their anti-proliferative effects against the HT-29, A549, and Lewis cell lines. Both of the previously isolated compounds inhibited the proliferation of these three cell lines in a dose-dependent manner, with the most significant effect being in the A549 cells, but neither reached IC50 at 50 μM. These results revealed that S. nigrum had weak cytotoxicity, indicating its clinical safety as a traditional anti-tumor herbal medicine.
- Lin, Li,Liu, LiangYu,Wang, JianNong,Wang, WenYi,Wu, Tong,Yang, YuKe
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- Two novel flavonoids from the leaves of Rhododendron dauricum L. with their inhibition of TNF-α production in LPS-induced RAW 264.7 cells
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Two new flavonoids, (2S)-6,8-dimethyl-5,7,3′,4′-tetrahydroxyflavanone 4′-O-β-D-glucopyranoside (1) and quercetin 3-O-β-D-(6′′-p-methoxybenzoyl)-galactopyranoside (2), together with ten known flavonoids (3–12) were isolated from the leaves of Rhododendron dauricum L. The structures of the flavonoids were characterized from spectroscopic data (1D and 2D NMR and HR-ESI-MS). The isolated flavonoids were evaluated for their inhibitory effects on the production of tumour necrosis factor (TNF)-α in LPS-stimulated RAW 264.7 cells. Compound 11 exhibited inhibitory activity against TNF-α production with an IC50 value of 46.2 ± 1.2 μM.
- Ye, Chao,Jin, Mei,Jin, Chunshi,Wang, Rongshen,Wang, Jiaming,Zhang, Ying,Li, Sainan,Sun, Jinfeng,Zhou, Wei,Li, Gao
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p. 1331 - 1339
(2019/08/15)
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- Studies on isolation and structural identification of saponins from the herb Hylomecon japonica and their bioactivities
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Three undescribed oleanane type triterpenoid saponins (1–3), along with one known saponin (4) were isolated from the whole herb of Hylomecon japonica. Their structures were elucidated by analysis of 1D and 2D-NMR (1H–1H COSY, HSQC, and HMBC) spectroscopic data, mass spectrometry (HR-ESI-MS) and chromatographic date (GC and LC) as 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (1), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-L-arabinopyranosyl ester (2), 3-O-β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-galactopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-galactopyranosyl ester (3), 3-O-β-D-galactopyranosyl-(1 → 2)-[α-L-arabinopyranosyl-(1 → 3)]-β-D-glucuronopyranosyl gypsogenin 28-O-β-D-glucopyranosyl-(1 → 3)-[β-D-xylopyranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl ester (4). All saponins possess a partial sequence β-D-galactopyranosyl-(1 → 2)-β-D-glucuronopyranosyl at C-3 of the aglycon. Compound 1 has cytotoxic activity against human colon cancer cell lines HT29, 3 against human gastric cancer cell lines AGS, and 4 against human lung cancer cell lines A549, AGS and HT29. Among them, compounds 3 and 4 showed significant inhibitory effect against AGS with IC50 value of 6.01 ± 1.4 μM, 3.66 ± 1.8 μM, respectively. These results represent a contribution to the chemotaxonomy of the saponins of Hylomecon japonica and their bioactivities.
- Li, Fei,Wu, Si-Tong,Qu, Ming-Hui,Wang, Yi-Xiao,Ma, Chun-Liu,Yu, Bai-Hong,Wang, Guang-Shu
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- Steroidal glycosides from the underground parts of Hosta ventricosa and their anti-inflammatory activities in mice
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Two new pregnane glycosides, 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside} (1) and 2α, 3β-dihydroxy-5α-pregn-16-en-20-one-3-O-{β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}(2), have been isolated along with two known spirostanol saponins from the underground parts of Hosta ventricosa. Their structures were elucidated on the basis of chemical and spectral evidence. The anti-inflammatory activities of these steroidal glycosides were evaluated using a xylene-induced ear edema model. Our results indicated that the compounds exhibited promising anti-inflammatory activities.
- Chu, Hong-Biao,Li, Nan-Nan,Zhang, Zong-Ping,Hu, Xiao-Yue,Yu, Cai-Yun,Hua, Lei
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p. 1766 - 1774
(2019/07/16)
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- Cytotoxic steroidal saponins from the roots and rhizomes of Maianthemum henryi
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Henryiosides F and G (1 and 2), two new steroidal saponins along with two known analogues (3 and 4) were obtained from the roots and rhizomes of Maianthemum henryi. Their structures were determined by physicochemical properties and spectroscopic methods including 1D, 2D-NMR, IR and HR-ESI-MS data analysis. Cytotoxic activity in human HepG2 and SW620 tumour cells were evaluated by the MTT method and all of the saponins exhibited cytotoxicity with IC50 values ranging from 15.33 μM to 57.85 μM.
- Zhang, Xin,Sun, Jing,Zhang, Xiaofei,Zhang, Shuo,Zhang, Xuan,Xue, Xuanji,Guo, Zengjun
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p. 1808 - 1815
(2019/08/07)
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- Steroidal constituents isolated from the seeds of Withania somnifera
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A new withanolide glycoside (1), two new ergostanol glycosides (2 and 3), and a new furostanol glycoside (4), along with nine known steroidal derivatives (5–12) were isolated from the seeds of Withania somnifera. The structures of the new compounds were determined using spectroscopic analysis and hydrolysis. The cytotoxic activities of the isolated compounds were evaluated against Ca9-22 human gingival carcinoma cells, HSC-2 human mouth carcinoma cells, and HL-60 human promyelocytic leukemia cells. Only 12 exhibited cytotoxic activity against these cell lines with IC50 values of 0.38, 0.54, and 1.5 μM, respectively.
- Iguchi, Tomoki,Kuroda, Minpei,Ishihara, Mai,Sakagami, Hiroshi,Mimaki, Yoshihiro
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supporting information
p. 2205 - 2210
(2019/11/03)
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- Structural features and antioxidant activity of a new galactoglucan from edible mushroom Pleurotus djamor
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A new water soluble galactoglucan with apparent molecular weight ~1.61 × 105 Da, was isolated from the edible mushroom Pleurotus djamor by hot water extraction followed by purification through dialysis tubing cellulose membrane and sepharose 6B column chromatography. The sugar analysis showed the presence of glucose and galactose in a molar ratio of nearly 3:1 respectively. The structure of the repeating unit in the polysaccharide was determined through chemical and NMR experiments as:[Formula presented] In vitro antioxidant studies showed that the PDPS exhibited hydroxyl radical scavenging activity (EC50 = 1.681 ± 0.034 mg/mL), DPPH radical scavenging activity (EC50 = 3.83 ± 0.427 mg/mL), reducing power (EC50 = 4.258 ± 0.095 mg/mL), and ABTS radical quenching activity (EC50 = 0.816 ± 0.077 mg/mL). So, PDPS should be explored as a natural antioxidant.
- Maity, Gajendra Nath,Maity, Prasenjit,Khatua, Somanjana,Acharya, Krishnendu,Dalai, Sudipta,Mondal, Soumitra
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p. 743 - 749
(2020/12/07)
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- Flavonol glycosides and phenylpropanoid glycosides with inhibitory effects on microglial nitric oxide production from Neoshirakia japonica
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Five new flavonol glycosides (1–5), one new phenylpropanoid glycoside (6), and nine known glycosides (7–15) were isolated from the stems and leaves of Neoshirakia japonica. The structures of the new compounds were determined by detailed analysis of spectroscopic data (HRESIMS, 1D and 2D NMR) and acid hydrolysis experiment. The antineuroinflammatory effects of all the isolates were evaluated by inhibiting NO production against LPS-induced BV-2 microglial cells. Compounds 1, 8, and 9 showed more potent inhibitory activities with IC50 values of 2.7, 5.5, and 4.1 μM, respectively, than that of the positive control minocycline (IC50 = 15.6 μM), while compounds 7 (IC50 = 17.0 μM) and 10 (IC50 = 24.3 μM) also displayed inhibitory activities to a certain degree.
- Zhao, Hai-Yan,Wang, Ya-Qi,Li, Yan-Cai,Lan, Qian,Liao, Hai-Bing,Wang, Heng-Shan,Liang, Dong
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- Cytotoxic steroidal glycosides from Polygonatum odoratum (Mill.) Druce
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Twenty-five steroidal glycosides including eight undescribed compounds which were named as polygonatumosides H–O, were isolated from the 70 % EtOH extract of rhizomes of Polygonatum odoratum (Mill.) Druce (Asparagaceae). Their structures were elucidated b
- Chen, Gang,Feng, Yuan,Koike, Kazuo,Li, Ning,Li, Wei,Liu, Bo,Liu, Xin,Sun, Lu,Zhou, Di
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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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- Five new steroidal saponins from the seeds of Solanum melongena L.
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Two novel cholestane-type steroidal saponins, melongoside R-S (1-2) and three novel furostanol-type steroidal saponins, melongoside T-V (3-5), together with three known steroidal saponins (6-8) were isolated from the seeds of Solanum melongna L. The struc
- Chen, Fang-Fang,Zhou, Jing,Zhang, Yu-Wei,Chen, Ya-Ping,Wang, Yin-Ru,Zhao, Yun-Fang,Liu, Wei,Huang, Xue-Feng
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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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- Anti-inflammatory active components of the roots of Datura metel
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One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we
- Qin, Ze,Zhang, Jin,Chen, Liang,Liu, Shu-Xiang,Zhao, Hai-Feng,Mao, Hui-Min,Zhang, Hong-Yang,Li, De-Fang
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p. 392 - 398
(2020/03/30)
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- Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases
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Small molecule irreversible inhibitors are valuable tools for determining catalytically important active-site residues and revealing key details of the specificity, structure, and function of glycoside hydrolases (GHs). β-glucans that contain backbone β(1,3) linkages are widespread in nature, e.g., mixed-linkage β(1,3)/β(1,4)-glucans in the cell walls of higher plants and β(1,3)glucans in yeasts and algae. Commensurate with this ubiquity, a large diversity of mixed-linkage endoglucanases (MLGases, EC 3.2.1.73) and endo-β(1,3)-glucanases (laminarinases, EC 3.2.1.39 and EC 3.2.1.6) have evolved to specifically hydrolyze these polysaccharides, respectively, in environmental niches including the human gut. To facilitate biochemical and structural analysis of these GHs, with a focus on MLGases, we present here the facile chemo-enzymatic synthesis of a library of active-site-directed enzyme inhibitors based on mixed-linkage oligosaccharide scaffolds and N-bromoacetylglycosylamine or 2-fluoro-2-deoxyglycoside warheads. The effectiveness and irreversibility of these inhibitors were tested with exemplar MLGases and an endo-β(1,3)-glucanase. Notably, determination of inhibitor-bound crystal structures of a human-gut microbial MLGase from Glycoside Hydrolase Family 16 revealed.
- Jain, Namrata,Tamura, Kazune,Déjean, Guillaume,Van Petegem, Filip,Brumer, Harry
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p. 1968 - 1984
(2021/05/26)
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- The anti-hyperuricemic effects of green alga Enteromorpha prolifera polysaccharide via regulation of the uric acid transporters in vivo
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A novel polysaccharide obtained from Enteromorpha prolifera (EPP) was purified through diethylaminoethyl cellulose-52 and Sephadex G-75 chromatography. Fourier transform infrared spectroscopy, high-performance liquid chromatography, and nuclear magnetic resonance (NMR) spectroscopy were employed to analyse the structure of EPP. It mainly comprised rhamnose, glucuronic acid, galactose, arabinose, and xylose at a molar ratio of 20.45:12.74:10.99:5.84:1.95, and its average molecular weight was 46.56 kDa. The seven major glycosidic residues identified by NMR were as follows: →2)-α-L-Araf-(1→, →2)-α-L-Rhap-(1→, →4)-α-L-Rhap-(1→, →2,6)-β-D-Galp-(1→, →4)-β-D-GlcpA-(1→, →3,4)-β-D-GlcpA-(1→, and →4)-β-Xylp-(1→. The effect of EPP on hyperuricemic mice was determined by analysing correlative general physical parameters, renal histopathology, renal gene expressions, and gut microbiome. EPP significantly reduced serum uric acid (UA), serum blood urea nitrogen, serum xanthine oxidase (XOD), and hepatic XOD as well as improved histological parameters in hyperuricemic mice. Furthermore, mRNA and protein expression analyses showed the upregulation of UA excretion genes such as ABCG2, OAT1, and NPT1 and downregulation of UA resorption gene URAT1. Moreover, EPP maintained the stability of the intestinal flora and confirmed that Parasutterella is closely related to the regulation of hyperuricemia. This study is the first to demonstrate the anti-hyperuricemic activity of EPP and highlight its therapeutic potential for hyperuricemia-related diseases.
- Chen, Xinhua,Gao, Xiaoxiang,Li, Xiaoqing,Liu, Yuanyuan,Sarker, Md Moklesur Rahman,Wu, Yijing,Zhang, Hui,Zhao, Chao
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- Cytotoxic steroidal saponins from the rhizome of Anemarrhena asphodeloides
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Two novel steroidal saponins, timosaponin V and W (1 and 2), together with seven known steroidal saponins (3–9), were isolated from the rhizomes of Anemarrhena asphodeloides Bunge. Their structures were elucidated by extensive 1D NMR and 2D NMR (HSQC, HMBC, 1H–1H COSY, and NOESY), and MS analyses. The cytotoxic activities of the isolates were evaluated. Compound 1 showed a significant cytotoxic activity against MCF-7 and HepG2 cell lines with IC50 values of 2.16 ± 0.19 μM and 2.01 ± 0.19 μM, respectively.
- Zhao, Yun-Fang,Zhou, Jing,Zhang, Min-Jie,Zhang, Min,Huang, Xue-Feng
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- Flavonol glycosides from Fissistigma maclurei
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Two new flavonol glycosides, fissmacosides A (1) and B (2) along with two known flavonol glycosides, kaempferol 3-O-α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside (3) and kaempferol 3-O-β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→6)-[4-(E)-feruloyl]-β-d-galactopyranoside (4) were isolated from the methanol extract of the leaves of Fissistigma maclurei Merr. Their structures were determined on the basis of extensive spectroscopic methods, including 1D-, 2D-NMR, and MS data.
- Ba, Nguyen Van,Men, Chu Van,Khi, Nguyen Tien,Tiet, Tran Viet,Khanh, Pham Gia,Quang, Le Bach,Chuyen, Nguyen Van,Tien, Vu Dinh,Nhiem, Nguyen Xuan,Kiem, Phan Van
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p. 1011 - 1017
(2019/11/21)
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- Melophluosides A and B, new triterpene galactosides from the marine sponge Melophlus sarasinorum
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Two new triterpene galactosides, melophluosides A and B, were isolated from a marine sponge Melophlus sarasinorum collected in Indonesia. Their structures were determined by the analysis of spectroscopic data and chemical reactions. The absolute configuration of cyclohexenone moiety was determined by the calculated ECD spectrum of a simplified model. Melophluosides A and B exhibited moderate cytotoxicity against HeLa cells (IC50, 11.6 and 9.7 μM, respectively).
- Angkouw, Esther D.,Fukumoto, Arina,Hitora, Yuki,Ise, Yuji,Mangindaan, Remy E. P.,Sadahiro, Yusaku,Tsukamoto, Sachiko
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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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- Novel steroidal glycosides from the whole plants of helleborus foetidus
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Phytochemical analysis of the whole Helleborus foetidus plants identified 28 steroidal glycosides (1-28), including 20 novel spirostanol glycosides (1-20) and a novel furostanol glycoside (21). The structures of the newly identified compounds were elucidated by two-dimensional NMR spectroscopy and hydrolytic cleavage. Compounds 12, 13, and 15 were determined to be spirostanol trisdesmosides bearing sugar moieties at the C-1, -21, and -24 hydroxy groups of the aglycone unit. The isolated compounds were subsequently evaluated for cytotoxic activity against HL-60 human promyelocytic leukemia cells and A549 human lung carcinoma cells. In particular, 7 showed cytotoxic activity against the HL-60 and A549 cells, with IC50 values of 5.9 and 6.6μM, respectively, whereas 19 was selectively cytotoxic to A549 cells with an IC50 value of 5.5μM.
- Iguchi, Tomoki,Uchida, Yuka,Takano, Shingo,Yokosuka, Akihito,Mimaki, Yoshihiro
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p. 273 - 287
(2020/11/26)
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- Structural features and anti-gastric cancer activity of polysaccharides from stem, root, leaf and flower of cultivated Dendrobium huoshanense
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The structure features and anti-gastric cancer activities in vitro of stem, root, leaf and flower polysaccharides from cultivated Dendrobium huoshanense were investigated systematically. Stem polysaccharide (cDHPS) was composed of →4)-β-D-Glcp-(1→, →4)-β-
- Liu, Bing,Shang, Zhen-Zi,Li, Qiang-Ming,Zha, Xue-Qiang,Wu, De-Ling,Yu, Nian-Jun,Han, Lan,Peng, Dai-Yin,Luo, Jian-Ping
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p. 651 - 664
(2019/12/24)
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- Triterpene glycosides from Silene odontopetala
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Silene species are known for their use in traditional medicine in treating several diseases. To the authors’ knowledge there is no report on the chemical composition of S. odontopetala. Therefore, the phytochemical investigation of the methanol extract of S. odontopetala was carried out, leading to the isolation of six undescribed oleanane-type glycosides along with the known saponin azukisaponin IV. Their structures were elucidated by the analysis of 1D and 2D-NMR experiments, along with mass spectrometry analysis. The cytotoxic activity of oleanane-type saponins was evaluated against a small panel of cancer cell lines, including PC-3 (prostate carcinoma cells), MCF-7 (breast cancer cells), A549 (alveolar basal carcinoma cells), and HeLa (cervical carcinoma cells). Furthermore, the activity of isolated compounds against a normal cell line HEK-293, used for assessing their cytotoxicity, was evaluated.
- ün, Rabia Nur,Alankus, Ozgen,Karayildirim, Tamer,Masullo, Milena,Nalbantsoy, Ay?e,Piacente, Sonia
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- Studies on isolation, characterization of fucoidan from brown algae Turbinaria decurrens and evaluation of it's in vivo and in vitro anti-inflammatory activities
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In the present study, the anti-nociception and anti-inflammatory activity of fucoidan isolated from T. decurrens on formalin induced paw-edema in mice model were investigated. The extracted fucoidan contain 54.86% of total sugar, 23.51% of sulfate and 3.4% of protein. The monosaccharide composition analysis revealed that fucoidan encompassed of fucose (59.3%), galactose (12.6%), mannose (9.6%), rhamnose (6.4%) and xylose (11.4%). Further, the structural characterization was done by UV–visible spectroscopy, X-ray diffraction, FT-IR and 1HNMR analysis. The fucoidan reduced the licking time thereby suggesting anti-nociceptive effect and decreased the size of paw swelling in the formalin induced inflammatory edema condition. The isolated fucoidan could significantly decreased the MDA and also increase the SOD, CAT, GPx, GST and GSH activity in paw edema tissue of formalin injected mice. Furthermore, fucoidan administration retained p65/NF-κB transcription factor in the cytosol thereby showing down regulation of the gene expression of pro-inflammatory mediators such as IL-1β, COX-2 and MMP-9 in fucoidan treated mice. The anti-inflammatory effect of fucoidan was attributed to its capacity on modulating the levels of enzymatic antioxidants, master regulator NF-κB and pro-inflammatory cytokines. The fucoidan has reduced LPS induced cytotoxicity in IC-21 macrophage at a dose depended on manner.
- Arumugam, Munuswamy,Beulaja, Manikandan,Janarthanan, Sundaram,Mahalakshmi, Krishnan,Manikandan, Ramar,Palanisamy, Subramanian,Parimalanandhini, Duraisamy,Prabhu, Narayanasamy Marimuthu,You, SangGuan
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p. 1263 - 1276
(2020/07/03)
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- Cytotoxic steroidal glycosides from the underground parts of Hosta ventricosa
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A phytochemical study on the underground parts of Hosta ventricosa yielded one new spirostanol saponin (1), two new furostanol saponins (2 and 3), and one new pregnane glycoside (4), along with three known compounds (5?7). Their structures were elucidated on the basis of chemical and spectroscopic analysis. All isolated compounds were evaluated for their cytotoxic effects against five human cancer cell lines (HL-60, A-549, SMMC-7721, MCF-7, and SW-480). Compounds 1, 2, and 5?7 showed cytotoxic activities with IC50 values of 3.21-17.06 μM.
- Chu, Hong-Biao,Dan, Zeng-Lamu,Gao, Yan,Li, Dan,Li, Rui,Zhang, Jia-Ping
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- Steroidal saponins from Raphia vinifera and their cytotoxic activity
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Phytochemical analysis of the fruits of Raphia vinifera led to the isolation of four new steroidal saponins (1–4), along with six known secondary metabolites (6–10). The structures of the isolated compounds were determined based on the analyses of NMR and
- Chi, Godloves Fru,Efferth, Thomas,Fotso, Ghislain Wabo,Kuete, Victor,Mbaveng, Armelle T.,Ngadjui, Bonaventure T.,Omollo Ombito, Japheth,Sop, Rodrigue V. T.,Nguenang, Ga?lle S.
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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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- Method for preparing lactic acid through catalytically converting carbohydrate
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The invention relates to a method for preparing lactic acid through catalytically converting carbohydrate, and in particular, relates to a process for preparing lactic acid by catalytically convertingcarbohydrate under hydrothermal conditions. The method disclosed by the invention is characterized by specifically comprising the following steps: 1) adding carbohydrate and a catalyst into a closedhigh-pressure reaction kettle, and then adding pure water for mixing; 2) introducing nitrogen into the high-pressure reaction kettle to discharge air, introducing nitrogen of 2 MPa, stirring and heating to 160-300 DEG C, and carrying out reaction for 10-120 minutes; 3) putting the high-pressure reaction kettle in an ice-water bath, and cooling to room temperature; and 4) filtering the solution through a microporous filtering membrane to obtain the target product. The method can realize high conversion rate of carbohydrate and high yield of lactic acid, and has the advantages of less catalyst consumption, good circularity, small corrosion to reaction equipment and the like.
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Paragraph 0029-0040
(2020/11/01)
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- Phenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities
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As a continuation of investigating Impatiens L. genus, eight flavonoids, eriodyctiol, eriodyctiol 7-O-β-?-glucoside, kaempferol 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside, kaempferol 3-rhamnosyl-di-glucoside, kaempferol 3-O-β-?-rutinoside, quercetin 3-O-β-?-glucoside and quercetin 3-O-β-?-galactoside, two phenolic acids–p-hydroxybenzoic acid and protocatechuic acid, and 2-methoxynaphthalene-1,4-dione were isolated from the aerial parts of I. glandulifera collected in Poland. The structures of the compounds were established by analysis of their spectroscopic (1H and 13C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. Quercetin 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside and kaempferol 3-O-β-?-rutinoside were isolated for the first time from the investigated taxon. In addition, the antioxidant activities in different tests of all obtained compounds were evaluated. The results clearly showed that among analyzed constituents, quercetin 3-O-β-?-glucoside exhibited antioxidant activity comparable or better than ascorbic acid and Trolox which were used as a positive control.
- Szewczyk, Katarzyna,Sezai Cicek, Serhat,Zidorn, Christian,Granica, Sebastian
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supporting information
p. 2851 - 2855
(2018/09/14)
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- A novel linear 3-O-methylated galactan isolated from Cantharellus cibarius activates macrophages
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A novel polysaccharide (WCCP-N-b) with a molecular weight of 18 kDa was isolated and purified from the fruiting bodies of Cantharellus cibarius. Monosaccharide composition, methylation analysis and NMR spectra indicated that WCCP-N-b was a linear α-1,6-galactan, partially methylated at O-3 of galactose. The molar ratio of Gal, 3-methylated-Gal, Glc and Man was 14.4:4.6:1.0:1.2. WCCP-N-b could significantly increase macrophage phagocytosis, release of NO and secretion of TNF-α, IL-6 and IL-1β. On a cellular mechanistic level, WCCP-N-b activated MAPKs and NF-κB signaling pathway via Toll-like receptor 2 (TLR2). To further elucidate the structure-function relationship, WCCP-N-b was hydrolyzed by acid. Four degraded fragments were obtained, with molecular weights of 16.1 kDa, 11.2 kDa, 5 kDa and 3.5 kDa, respectively. Their macrophage activation effects were significantly decreased along with the molecular weight decrease. Collectively, WCCP-N-b could activate RAW264.7 cells, and the activation effect was related to its molecular weight.
- Yang, Guang,Qu, Yunhe,Meng, Yue,Wang, Yushi,Song, Chengcheng,Cheng, Hairong,Li, Xiaomeng,Sun, Lin,Zhou, Yifa
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- Structural characterization of an active polysaccharide of longan and evaluation of immunological activity
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An active polysaccharide (LPD2) was isolated from longan pulp by comparing the effects of polysaccharides on the phagocytosis of macrophages. LPD2 was composed of arabinose, mannose, glucose, and galactose in a molar ratio of 0.25:0.49:1:0.5 with average molecular weight of 9.64 × 106 Da. The main linkages of the sugar residues of LPD2 were (1→4)-β-Glc and (1→6)-β-Man. LPD2 significantly enhanced the lymphocytes proliferation, phagocytosis and NO and IL-6 secretion by macrophage. The anti-TLR2 and anti-TLR4 mAbs markedly suppressed LPD2-mediated NO and IL-6 production. Furthermore, anti-TLR4 or anti-TLR2 plus anti-TLR4 treatment significantly decreased LPD2-induced increase of MyD88, IRAK4, TRAF6 and INOS mRNA expression. Moreover, western blotting analysis showed that LPD2 enhanced the expression of target proteins in MyD88/IRAK4-TRAF6- INOS pathways. These results suggested that LPD2 induced macrophage activation partly via the TLR2- and TLR4-mediated MyD88/IRAK4-TRAF6 signaling pathways. Knowing the structural features and activities of active polysaccharide of longan gives the insights into longan polysaccharide application as an immunomodulatory agent.
- Rong, Yu,Yang, Ruili,Yang, Yuzhe,Wen, Yazhou,Liu, Sixin,Li, Congfa,Hu, Zhuoyan,Cheng, Xiangrong,Li, Wu
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p. 247 - 256
(2019/03/08)
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- Two New Triterpene Glycosides in the Roots of Uraria crinita
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Two new triterpene glycosides, 24-deoxyoxytrogenin 3-O-α-L-rhamnopyranosyl (1→2)[β-D-glucopyra-nosyl]-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranoside and sophoradiol 3-O-α-L-rhamnopyranosyl (1→2)-β-D-glucuronopyranosyl (1→2)-β-D-glucuronopyranoside with four known glycosides were isolated from a Chinese natural medicine, the roots of Uraria crinita (L.) DESV. Their structures were determined by chemical and spectral methods.
- Okawa, Masafumi,Akahoshi, Ryo,Kawasaki, Kyoko,Nakano, Daisuke,Tsuchihashi, Ryota,Kinjo, Junei,Nohara, Toshihiro
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p. 159 - 162
(2019/04/09)
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- Discovery of cardio-protective constituents of Gualou Xiebai Decoction, a classical traditional Chinese medicinal formula
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Backgroud: Finding effective compounds of TCMs has always been the basis for achieving marker-based quality control which is currently most widely used quality control strategy. Gualou Xiebai Decoction (GLXB), a classical TCM formula, is recorded and proven as a therapy for curing coronary heart disease but the effective constituents are unidentified and the substantial basis of the therapeutic effects is not clear. Purpose: The present research is an investigation on the chemistry of this formula aiming at finding and precisely identifying effective compounds. Study design and methods: This research started with screening for effective fractions of GLXB by rat myocardial infarction model and H9c2 cell hypoxia/reoxygenation model, then compounds in effective fractions were isolated and identified by phytochemical and spectroscopic methods. The cardio-protective activities of the compounds were tested in vitro and one of the effective compounds was taken as example to investigate the mechanisms. Results: The water-insoluble parts of GLXB were identified as effective parts in both in vitro and in vivo experiments. Systematic isolation of compounds in the effective fractions resulted in the isolation of 34 compounds including 7 new compounds, whereas 8 compounds were effective in protecting H9c2 cells against hypoxia/reoxygenation injury. One of the effective compounds, macrostemonoside P (MP) possibly exerted its effect by activating RISK pathway and attenuating apoptosis. Conclusion: An array of effective constituents of GLXB were discovered, and discovery of these compounds contributed to elucidating the substantial basis for the therapeutic effects of this formula, and provides fundaments for establishing Q-markers for further reliable quality control of GLXB.
- Zhang, Wei-Yang,Yu, Yang,Yan, Lu-Lu,Li, Chong,Han, Jing-Yan,Qin, Zi-Fei,Dai, Yi,Yao, Zhi-Hong,Zhou, Hua,Yao, Xin-Sheng
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p. 318 - 327
(2018/07/31)
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- PPAR α and γ Activation Effects of New Nor-triterpenoidal Saponins from the Aerial Parts of Anabasis articulata
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Anabasis articulata, traditionally used to treat diabetes, is rich in saponin content. This study was performed to investigate the agonistic effect of its saponins on peroxisome proliferator-activated receptor- α and peroxisome proliferator-activated receptor- γ in human hepatoma (HepG2) cells to explore the possibility of the involvement of these nuclear receptors in the mechanism of the antidiabetic effect of the plant. Chemical investigation of the n -butanol fraction resulted in the isolation of three new and one known 30-noroleanane triterpenoid saponins. The structures of the new compounds were elucidated as 3 β -hydroxy,23-aldehyde-30-norolean-12,20(29)-dien-28-oic acid-28- O - β -D-glucopyranosyl ester (1), 3 β - O -D-galactopyranosyl-23-aldehyde-30-norolean-12,20(29)-dien-28-oic acid-28- O - β -D-glucopyranosyl ester (2), and 3 β - O -D-xylopyranosyl-30-norolean-12,20(29)-dien-28-oic acid 28- O - β -D-glucopyranosyl ester (3), while the known 30-nortriterpenoidal saponin was identified as boussingoside E (4). Although, the isolated saponins (1 - 4) did not show > 1.5-fold activation of peroxisome proliferator-activated receptor- γ, but two of them (1 and 3) activated peroxisome proliferator-activated receptor- α to the higher extents of 2.25- and 1.86-fold, respectively. These results suggest that the reported antidiabetic action of the isolated saponins may not solely involve the activation of peroxisome proliferator-activated receptor- γ. However, the agonistic activity of the n -butanol fraction of A. articulata (1.71-fold induction) and two of its saponins (1 and 3) towards peroxisome proliferator-activated receptor- α may be beneficial in the cardiovascular condition that is closely associated with diabetes and other metabolic disorders.
- Salah El Dine, Riham,Abdallah, Hossam M.,Kandil, Zeinab A.,Zaki, Ahmed A.,Khan, Shabana I.,Khan, Ikhlas A.
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p. 274 - 281
(2019/05/04)
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- Structural elucidation, antioxidant and immunomodulatory activities of a novel heteropolysaccharide from cultured Paecilomyces cicadae (Miquel.) Samson
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The fine structure and chain conformation of a heteropolysaccharide (PCIPS3) from mycelium of Paecilomyces cicadae were investigated via the analysis of HPLC, IR, methylation, NMR spectroscopy and multiangle light scattering. It was determined to be a 2.23 × 104 g/mol heteropolysaccharide primarily composed of glucose, galactose and mannose in a molar ratio of 23.8:2.1:1.0. The PCIPS3 backbone consisted of 1,4-linked α-D-Glcp and 1,4-linked 6-O-Me-α-D-Glcp residues, which were occasionally interrupted by branched β-Galf residues through 1,6-linkage. Moreover, the α (0.60) from Mark–Houwink–Sakurada (MHS) equation suggested that PCIPS3 adopted a flexible chain conformation in 0.1 mol/L NaNO3 at 25 °C. The worm-like chains model parameters for PCIPS3 were estimated as following: ML = 437 nm?1, q = 0.46 nm and 0.79 nm, which were further evidenced by AFM. Furthermore, PCIPS3 showed excellent scavenging capacities of 2,2-diphenyl-1-picrylhydrazyl radical, superoxide radical, hydroxyl radical, ORAC radical and moderate immunomodulatory activity.
- Wang, Yanbin,He, Pengfei,He, Liang,Huang, Qingrong,Cheng, Junwen,Li, Weiqi,Liu, Yu,Wei, Chaoyang
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p. 270 - 281
(2019/04/17)
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- Anti-breast cancer triterpenoid saponins from the thorns of Gleditsia sinensis
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One new triterpenoid saponin (1), as well as six known ones (2–7), were isolated from the ethanol extract of the thorns of Gleditsia sinensis. Their structures were elucidated by extensive spectroscopic analysis in conjunction with chemical evidence. Cytotoxic activity of compounds 1–6 was evaluated against human breast cancer MCF 7 cells in vitro by the MTT method. Our results revealed moderate activities for compounds 1–6 with IC50 values of 18.43, 30.47, 18.46, 10.02, 30.76, and 17.32?μM, respectively. Furthermore, compounds 1, 3, 4, and 6 induced apoptosis in MCF 7 cell, with 1 and 6 causing late apoptosis of MCF 7 cells, while 3 and 4 acting oppositely.
- Yu, Jinqian,Li, Gang,Mu, Yan,Zhou, Honglei,Wang, Xiao,Yang, Peng
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supporting information
p. 2308 - 2313
(2018/03/01)
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- Anti-Influenza a virus of a new oligosaccharide citric acid derivative isolated from Vigna angularis (ohwi et ohashi. var. Dainagon) Seeds
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A new oligosaccharide citric acid derivative was isolated by hot aqueous extraction at 85 °C from Vigna angularis seeds, and it was purified using anion exchange chromatography DE-52. The structure was inferred by using UV, 1 D and 2 D NMR spectroscopy and HR-MALDI/MS, and identified as α-D-galactopyranosyl-(1→6)-α-D-galactopyranosyl-(1→6)-α-D-glucopyranosyle-(1→2)-β-D-fructofuranosyle citric acid. The isolated oligosaccharide citric acid derivative revealed promising anti-influenza A virus with 50% inhibition concentration (IC50) of 0.162 nM/mL and 50% cytotoxic dose (CC50) of >2.38 nM/mL.
- Mohammed, Magdy M. D.,Kobayashi, Nobuyuki
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p. 234 - 245
(2019/07/03)
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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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- Antibacterial Activity of a New Flavone Glycoside from the Stems of Holmskioldia sanguinea Retz.
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A new flavone glycoside was isolated from ethanolic extract of stem parts of Holmskioldia sanguinea Retz. Its structure was characterized as 3,4′-dihydroxy-5,7-dimethoxyflavone-3-O-β-D-galactopyranosyl(1→4)-O-β-D-arabinopyranosyl-4′-O-α-L-rhamnopyranoside (1) by colour reactions, chemical degradation and spectroscopic analysis. Antibacterial activity of compound 1 was evaluated against various Gram positive and Gram negative bacteria showing a significant effects.
- Yadava,Raghuvansi, Jyotsna
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p. 1815 - 1818
(2019/07/18)
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- Aspidsaponins E-H, Four new steroidal saponins from the rhizomes of Aspidistra elatior Blume and their anti-inflammatory activity
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Four new furostanol saponins, named aspidsaponins E-H (1–4) were isolated from the rhizomes of Aspidistra elatior Blume. Their structures were determined based on chemical methods and spectral data. Compounds 1 and 2 were a pair of diastereoisomeric furostanol saponins and possessed the highly oxidized structural feature of 1β, 2β, 3β, 4β, 5β, 26-hexanol-steroids, and compounds 3-4 were steroidal glycosides with a tetra-saccharide chain at C3. The isolated compounds (1–4) were tested in vitro for inhibitory activities against LPS-induced nitric oxide production in RAW264.7 macrophages. Among them, compounds 3 and 4 showed excellent anti-inflammatory activities with IC50 values 82.1 and 65.9 μM, respectively.
- Sun, Zhi-Ying,Zuo, Sheng-Qi,Yang, Xia,Lan, Jia-Hui,Liu, Cheng-Xiong,Guo, Zhi-Yong,Cheng, Fan,Zou, Kun
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- A New Coumarin Glycoside from Physochlaina physaloides
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A new coumarin glycoside, namely physochloside A, together with four known compounds, was isolated from the ethanol extract of Physochlaina physaloides. The structure of physochloside A was identified by UV, IR, ESI-MS, 1D NMR, and 2D NMR.
- Wang, Qing-hu,He, Xiang,Hao, Jun-sheng,Bao, Wen-qiang,Pa, Bi-li-ge-tu-lan
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p. 806 - 808
(2019/11/03)
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- Constituents of the leaves and twigs of Elaeagnus umbellata and their proliferative effects on human keratinocyte HaCaT cells
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Bioassay-guided fractionation of an extract of leaves and twigs of Elaeagnus umbellata led to the isolation of a serotonin derivative, N-[2-(5-hydroxyl-1H-indol-3-yl)ethyl]-butanamide (1), along with six flavonoid glycosides, kaempferol-3-O-β-D-xylopyranosyl(1 → 2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (2), kaempferol-3-O-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (3), kaempferol-3-O-α-L-rhamnopyranosyl(1 → 6)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (4), kaempferol-3-O-β-D-xylopyranosyl(1 → 2)-β-D-galactopyranoside (5), kaempferol-3-O-rutinoside (6), and kaempferol-3-O-β-D-glucopyranosyl(1 → 2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (7). Their structures were elucidated using 1D/2D nuclear magnetic resonance spectroscopy and mass spectrometry. Compounds 1–6 were evaluated for their proliferative effects on HaCaT keratinocytes; 1–5 promoted keratinocyte proliferation dose dependently. Compounds 3 and 4 showed potent activities. These results suggest that the leaves and twigs of E. umbellata have wound healing and skin cell regeneration potentials.
- Paudel, Sunil Babu,Park, Jiyoung,Kim, Nam Hee,Choi, Hyukjae,Seo, Eun-Kyoung,Woo, Hyun Ae,Nam, Joo-Won
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- A new steroidal saponin from Polygonatum sibiricum
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A new furostan type steroidal saponin, kingianoside Z (1), along with four known compounds (2–5), was isolated from the ethanolic extract of Polygonatum sibiricum Delar. ex Redoute. Their structures were determined by spectroscopical method and by comparison with previously reported spectroscopic data. Compounds 3–5 showed significant cytotoxicity against HepG2 cell lines with IC50 values of 14.2, 12.1 and 8.5?μM, respectively.
- Zhang, Hong-Yang,Hu, Wei-Cheng,Ma, Guo-Xu,Zhu, Nai-Liang,Sun, Xiao-Bo,Wu, Hai-Feng,Xu, Xu-Dong
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p. 586 - 592
(2017/11/28)
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- Effect of polyphenols from Vicia faba L on lipase activity and melanogenesis
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Two new flavonoid glycosides, kaempferol 3-O-α-L-rhamnopyranosyl (1→6) (3′′-acetyl)-β-D-galactopyranoside 1 and kaempferol 3-O-α-L-arabinopyranosyl-5-O-α-L-rhamnopyranoside 2, along with six known ones 3–8 were isolated from the flowers of Vicia faba L. (Fabaceae). Methanol extract and the isolated compounds were tested against lipase and melanogenesis inhibition activities and resulted in that compound 2 showed 53 and 77% lipase inhibition activity in concentrations of 400 and 800?μg/mL, respectively. For melanogenesis, compounds 2, 3 and 4 exhibited potent melanogenesis inhibition activity where the melanin content in melanoma cells was decreased to be about 57.5, 56 and 61%, respectively, with no obvious melanocytotoxicity. The rest of compounds showed weak to moderate activity. The results of melanogenesis inhibition activity of this study suggested the potential use of Vicia faba flowers as a skin-whitening agent and reveal the flowers to be a rich source of important phytochemicals with antilipase and melanogenesis inhibitory activity.
- Allam, Ahmed E.,Nafady, Alaa M.,Nakagawa, Toshinori,Takemoto, Naomichi,Shimizu, Kuniyoshi
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p. 1920 - 1925
(2017/10/06)
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- Anti-inflammatory Potential of Flavonoids from the Aerial Parts of Corispermum marschallii
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The isolation of phenolics from aerial parts of Corispermum marschallii yielded a total of 13 compounds including nine previously undescribed patuletin and spinacetin glycosides. These were identified as patuletin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (1), spinacetin 3-O-β-d-galactopyranosyl-7-O-β-d-glucopyranoside (2), patuletin 3-O-(6″-O-β-d-glucopyranosyl)-β-d-galactopyranoside (3), patuletin 3-O-(6″-O-α-l-arabinopyranosyl)-β-d-galactopyranoside (4), patuletin 3-O-(2″-O-(5-O-α-l-arabinopyranosyl)-β-d-apiofuranosyl)-β-d-galactopyranoside (5), patuletin 3-O-(2″-O-β-d-apiofuranosyl)-β-d-galactopyranoside (6), spinacetin 3-O-β-d-galactopyranoside (7), patuletin 3-O-β-d-galactopyranosyl-7-O-(6-O-feruloyl)-β-d-glucopyranoside (8), and spinacetin 3-O-β-d-galactopyranosyl-7-O-(6-O-feruloyl)-β-d-glucopyranoside (9). Structure elucidation was based on UV-visible, multistage MS, and 1D and 2D NMR spectroscopy and chemical derivatization, which allowed the identification on the glycosides with two different hexose moieties occurring at different positions of the aglycones. Most of the compounds tested inhibited the production of pro-inflammatory factors such as ROS, IL-8, and TNF-α in stimulated neutrophils.
- Paw?owska, Karolina,Czerwińska, Monika E.,Wilczek, Marcin,Strawa, Jakub,Tomczyk, Micha?,Granica, Sebastian
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p. 1760 - 1768
(2018/09/10)
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- Structure and anticancer activity of native and modified polysaccharides from brown alga Dictyota dichotoma
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The laminaran DdL and fucoidan DdF were obtained from the brown alga Dictyota dichotoma. DdF was a sulfated (28.9%) and acetylated heteropolysaccharide containing fucose, galactose, mannose and glucose (57.9, 20.4, 12.4 and 9.2 mol%, respectively). DdL was a 1,3;1,6-β-D-glucan with the main chain built from 1,3-linked glucose residues and single glucose residue in branches at C6 (one branch on three glucose residues of the main chain). Sulfated (43.7%) laminaran DdLs was obtained from DdL by sulfation. It was determined that sulfates occur at C2, C4 and C6 of glucose residues. The anticancer effect of DdF, DdL, and DdLs (200 μg/mL) was studied in vitro on colon cancer cells HCT-116, HT-29, and DLD-1. The effect of polysaccharides (40 μg/mL) on colony formation of DLD-1 cancer cells after irradiation (4 Gy) was investigated first. All polysaccharides showed a synergistic effect with X-ray irradiation against cancer cells, decreasing the amount and size of cancer cells colonies.
- Usoltseva, Roza V.,Shevchenko, Natalia M.,Malyarenko, Olesya S.,Ishina, Irina A.,Ivannikova, Svetlana I.,Ermakova, Svetlana P.
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- The bioassay-guided isolation of antifungal saponins from Hosta plantaginea leaves
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Four new steroidal saponins hostaside Ⅰ (1), hostaside Ⅱ (2), hostaside Ⅲ (3), and hostaside Ⅳ (4), together with five known steroidal saponins (5–9), were isolated by the bioassay-guided fractionation from the leaves of Hosta plantaginea (Lam.) Aschers, a worldwide well-known ornamental plant. Hostasides Ⅰ and Ⅱ showed significant antifungal activities, and they could inhibit the growth of Candida albicans and Fusarium oxysporium with MIC values as low as 4?μg/ml.
- Wang, Meng-Yue,Peng, Ying,Peng, Chong-Sheng,Qu, Jiang-Yuan,Li, Xiao-Bo
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p. 501 - 509
(2017/10/05)
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