- 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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- 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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- Four new prenylflavonol glycosides from the leaves of Cyclocarya paliurus
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Four new prenylflavonol glycosides (1–4) along with two known analogues (5–6) were isolated from the leaves of Cyclocarya paliurus for the first time. The structures of these compounds were characterized by comprehensive analysis of 1 D, 2 D NMR, HRESIMS,
- Ye, Zi-Jun,Sun, Hui-Hui,Chen, Zu-Hui,Wu, Jian-Ping,Li, Jing,Zhu, Hui,Huang, Lu-Lu,Chang, Xi-Wen,Ou, Sai-Yu,Wang, Wen-Xuan,He, Xiao-Ai,Zhu, Gang-Zhi,Xu, Kang-Ping
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p. 772 - 779
(2020/08/10)
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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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- Two new iridoid glycosides from Gardeniae Fructus
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Two new iridoid glycosides, genipin 1,10-di-O-α-L-rhamnoside (1) and genipin 1,10-di-O-β-D-xylopyranoside (2), along with thirteen known compounds (3–15) were isolated from Gardeniae Fructus. Their structures were elucidated by physical data analyses such as NMR, UV, IR, HR-ESI-MS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory and antioxidant activities. At a concentration of 25 μM, compound 13 showed obvious mushroom tyrosinase inhibition activity with % inhibition value of 36.52 ± 1.98%, with kojic acid used as the positive control (46.09 ± 1.29%). At a concentration of 1 mM, compounds 8 and 9 exhibited considerable DPPH radical scavenging activities, with radical scavenging rates of 48.54 ± 0.47%, 58.59 ± 0.39%, respectively, with L-ascorbic acid used as the positive control (59.02 ± 0.77%).
- Shu, Penghua,Yu, Mengzhu,Zhu, Huiqing,Luo, Yuehui,Li, Yamin,Li, Nianci,Zhang, Hui,Zhang, Jialong,Liu, Guangwei,Wei, Xialan,Yi, Wenhan
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- A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities
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Our continuing search for marine bioactive secondary metabolites led to the screening of crude extracts of sea cucumbers by the model of Pyricularia oryzae. A new sulfated triterpene glycoside, coloquadranoside A (1), together with four known triterpene glycosides, philinopside A, B, E and pentactaside B (2–5) were isolated from the sea cucumber Colochirus quadrangularis, and their structures were elucidated using extensive spectroscope analysis (ESI-MS, 1D and 2D NMR) and chemical methods. Coloquadranoside A possesses a 16-acetyloxy group in the holostane-type triterpene aglycone with a 7(8)–double bond, a double bond (25,26) at its side chain, and two β-D-xylose in the carbohydrate chain. Coloquadranoside A exhibits in vitro some antifungus, considerable cytotoxicity (IC50 of 0.46–2.03 μM) against eight human tumor cell lines, in vivo antitumor, and immunomodulatory activity.
- Han, Hua,Qi, Xin-Rui,Shen, Li,Tang, Hai-Feng,Xu, Qiang-Zhi,Yang, Wen-Sheng,Yi, Yang-Hua,Yuan, Chun-Hong
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- Two new triterpenoid glycosides from leaves of Cyclocarya paliurus
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Two dammarane glycosides (1-2) were isolated from the leaves of Cyclocarya paliurus. The structures of new compounds were established by application of spectroscopic methods, including one-dimensional and two-dimensional NMR, HRESIMS, and chemical hydroly
- Chang, Xiwen,Chen, Huiyun,Gui, Rui,He, Xiaoai,Li, Guihua,Liu, Yiqian,Lu, Shijuan,Ou, Saiyu,Shangguan, Dangang,Sun, Huihui,Wang, Yuyan,Wu, Jianping,Xu, Kangping,Zha, Wenwen,Zhu, Hui
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- Neuroprotective and anti-inflammatory phenylethanoid glycosides from the fruits of Forsythia suspensa
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Neuroinflammation is emerging as a crucial reason of major neurodegenerative diseases in recent years. Increasingly evidences have supported that bioactive natural products from traditional Chinese medicines have efficiency for neuroinflammation. Forsythia suspensa, a typical medicinal herb, showed potential neuroprotective and anti-inflammatory properties in previous pharmacological studies. In our research to obtain neuroprotective and anti-inflammatory natural products, three unprecedented C6–C7′/C6–C16′ linked phenylethanoid glycoside dimers (1–3), three new phenylethanoid glycosides (4–6), and six known compounds (7–12) were isolated from the fruits of Forsythia suspensa. Their structures were determined by comprehensive spectroscopic data and comparison to the literature data. All isolated compounds were evaluated their neuroprotective and anti-inflammatory activities. Compounds 1 and 10 exhibited significant neuroprotective activities with the cell viability values of 75.24 ± 8.05% and 93.65 ± 10.17%, respectively, for the serum-deprivation and rotenone induced pheochromocytoma (PC12) cell injury. Meanwhile, compound 1 exhibited excellent anti-inflammatory activity against tumor necrosis factor (TNF)-α expression in LPS induced RAW264.7 cells with the IC50 value of 1.30 μM. This study revealed that the bioactive phenylethanoid glycosides may attenuate neuroinflammation through their neuroprotective and anti-inflammatory activities.
- Feng, Zi-Meng,Jiang, Jian-Shuang,Shao, Si-Yuan,Yang, Ya-Nan,Zhang, Fan,Zhang, Pei-Cheng
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- α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus
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Diabetes mellitus is caused by chronic inflammation and affects millions of people worldwide. Cyclocarya paliurus leaves have been widely used in traditional folk tea as a remedy for diabetes, but the antidiabetic constituents remain to be further studied. The α-glucosidase inhibitory and anti-inflammatory activities were examined to evaluate their effects on diabetes mellitus, and bioassay-guided separation of C. paliurus leaves led to the identification of twenty dammarane saponins, including eleven new dammarane saponins (1–11). The structures of the isolates were elucidated by spectroscopic methods. Bioactivity assay results showed that compounds 1 and 2 strongly inhibited α-glucosidase activity, with IC50 values ranging from 257.74 μM, 282.23 μM, and strongly inhibited the release of NO, with IC50 values of 9.10 μM, 9.02 μM. Moreover, compound 2 significantly downregulated the mRNA expression of iNOS, COX-2, IL-1β, NF-κB, IL-6 and TNF-α in LPS-mediated RAW 264.7 cells and markedly suppressed the protein expression of iNOS, NF-κB/p65, and COX-2. Dammarane glucoside 2 exhibited the strongest α-glucosidase inhibitory and anti-inflammatory activities. In addition, the structure–activity relationships (SARs) of the dammarane saponins were investigated. In summary, C. paliurus leaves showed marked α-glucosidase inhibitory and anti-inflammatory activities, and dammarane saponins are responsible for regulating α-glucosidase, inflammatory mediators, and mRNA and the protein expression of proinflammatory cytokines, which could be meaningful for discovering new antidiabetic agents.
- Deng, Shengping,Hao, Lili,Huang, Xishan,Huang, Yan,Li, Chenguo,Li, Jun,Liang, Cheng-qin,Liu, Wei,Su, Shanshan,Xu, Xia,Yang, Ruiyun,Zhang, Gaorong,Zhou, Dexiong
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supporting information
(2021/07/22)
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- Four New Triterpenoid Saponins from the Root of Ilex centrochinensis
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One new siaresinolic acid saponin (1) and three new rotundic acid saponins (2–4) were isolated from the roots of Ilex centrochinensis. Their structures were confirmed by detailed analysis of standard spectroscopic data (IR, MS, 1D and 2D NMR). Compounds 1–4 exhibited anti-inflammatory activity by inhibiting nitric oxide production in a lipopolysaccharide-induced RAW264.7 cell inflammatory model. However, they showed no significant lipid-lowering activity against the production of triglycerides in the lipid-accumulation model of HepG2 cells induced by oleic acid.
- Deng, Xue-Ying,Hu, Ze-Hua,Li, Lu-Jun,Lu, Yan-Xia,Shi, Yu,Yang, Hang,Yi, Ying-Tao
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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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- A new steroidal glycoside from the fruits of Solanum myriacanthum
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A new cholestane-type steroidal glycoside, solamyriaside A (1), was isolated from the fruits of Solanum myriacanthum Dunal (Solanaceae), along with two known steroidal glycosides, namely, solaviaside A (2) and aculeatiside A (3), and three known steroidal alkaloid glycosides, namely, solamargine (4), khasianine (5) and solasonine (6), which were isolated for the first time from this plant. Based on spectroscopic data as well as chemical evidence, 1 was determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranosyl-22R,25R-cholest-5-ene-3β,16α,22,26-tetraol 26-O-β-D-glucopyranoside. The cytotoxic activity of 1–6 against HL-60 human promyelocytic leukaemia cells was examined. Compounds 4–6 showed cytotoxic activity. Among them, 4 exhibited the strongest activity with an IC50 value of 4.64 ± 0.17 μM, similar to the activity of cisplatin, a positive control.
- Ono, Masateru,Shimode, Mizuki,Tsutsumi, Shuhei,Yasuda, Shin,Okawa, Masafumi,Kinjo, Junei,Miyashita, Hiroyuki,Ikeda, Tsuyoshi,Yoshimitsu, Hitoshi,Nohara, Toshihiro
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p. 326 - 333
(2020/07/04)
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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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- Protective effects of four new saponins from Gynostemma pentaphyllum against hydrogen peroxide-induced neurotoxicity in SH-SY5Y cells
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Gynostemma pentaphyllum has been used as a medicine-food homologious health product in China for a long time. This research aimed to isolate and identify its active compounds with protective effects against hydrogen peroxide induced SH-SY5Y cell death. Four new dammarane-type saponins were isolated from G. pentaphyllum using various chromatographic methods. They were identified as gypenoside S1 (1), gypenoside S3 (2), gypenoside S2 (3) and gypenoside S4 (4), respectively by HRESIMS and NMR spectra. Their cytotoxic activity was evaluated against three human cancer cell lines, A549 (lung), HepG2 (liver), SH-SY5Y (nerve), by MTT method. They showed low cytotoxicities with the IC50 values of more than 100 μM on three cancer cell lines. However, they appeared protective effects against hydrogen peroxide induced SH-SY5Y cell death in a dose-dependent manner. They recovered cell viability more than 69% at the concentration of 20 μM from 66%, while as vitamin C to 67%. Compound 3 and 4 recovered more than 79% at 100 μM. The present study suggests that G. pentaphyllum has antioxidative potential and the saponins from G. pentaphyllum are considered as the active compounds with safe and neuroprotecitve effect.
- Zhai, Xin-Fang,Zu, Ma-Li,Wang, Yu-Rong,Cui, Wei-Ye,Duan, Yu,Yang, Ce,Piao, Xiang-Lan
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- Phytochemicals from the Leaves of Cyclocarya paliurus and their 11β-HSD1 Enzyme Inhibitory Effects
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Two new dammarane-type triterpenoid saponins, 3β-(α-l-arabinopyranosyloxy)-24,25-dihydroxydammar-20-en-12α-yl 6-deoxy-β-d-glucopyranoside (1) and (24R)-3β-[(4-O-acetyl-α-l-arabinopyranosyl)oxy]-25-hydroxy-20,24-epoxydammaran-12β-yl 6-deoxy-β-d-glucopyrano
- Yan, Huan,Li, Xiang,Ni, Wei,Zhao, Qing,Leng, Ying,Liu, Hai-Yang
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- Chemical constituents of the bulbs of scilla peruviana and their pancreatic lipase inhibitory activity
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Scilla species are used as medicinal plants and contain lanosterol-type triterpene glyco-sides. The phytochemical investigation of the bulbs of Scilla peruviana led to the isolation of 17 com-pounds, including three new rearranged pentacyclic-lanosterol glycosides (1?3) and two new ho-moisoflavanone glycosides (12 and 13). The structures of the undescribed compounds were deter-mined by extensive spectroscopic analyses, including two-dimensional (2D) NMR. Among the triterpene glycosides, 2, 3, and 6 showed significant pancreatic lipase inhibitory activity in a concen-tration-dependent manner in vitro. The oral administration of scillascilloside D-2 (6) reduced serum triglyceride levels in a dose-dependent manner in soybean oil-loaded mice.
- Matsuo, Yukiko,Yamashiro, Asuka,Ootomo, Kanae,Nakagawa, Mika,Tsuchihashi, Hiroko,Inaba, Niro,Mimaki, Yoshihiro
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- New triterpene glycosides from the far eastern starfish solaster pacificus and their biological activity
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Three new triterpene glycosides, pacificusosides A–C (1–3), and three previously known triterpene glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1–3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its triterpene aglycon. This structural fragment has not previously been found in the sea cucumber triterpene glycosides or starfish steroidal glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new triterpene glycosides (2, 3) have closely related characteristics to sea cucumber glycosides. The cytotoxicity of compounds 1–6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4–6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2–6 were reduced by cholesterol like the similar effects of the previously investigated individual triterpene glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 μM.
- Malyarenko, Timofey V.,Kicha, Alla A.,Kalinovsky, Anatoly I.,Dmitrenok, Pavel S.,Malyarenko, Olesya S.,Kuzmich, Alexandra S.,Stonik, Valentin A.,Ivanchina, Natalia V.
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- 3,4-seco-Dammarane Triterpenoid Saponins with Anti-Inflammatory Activity Isolated from the Leaves of Cyclocarya paliurus
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Cyclocarya paliurus is commonly used for the prevention and treatment of hypertension, diabetes, and inflammation in South China. Although research on the anti-inflammatory effects of C. paliurus leaves has been reported, no active anti-inflammatory compounds have been identified. In the present study, RAW 264.7 cells were used to establish a bioactivity-guided identification model to verify the inhibitory effects of C. paliurus leaves on inflammation and identify the anti-inflammatory constituents. The active fraction was isolated to yield 18 dammarane triterpenoid saponins, including 11 new 3,4-seco-dammarane triterpenoid saponins (1-11), the structures of which were identified on the basis of analyses of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS) and comparison with literature data. Compounds 7, 8, 10, and 11 showed strong inhibition on nitric oxide (NO) productions, with IC50 values ranging from 8.23 to 11.23 μM. These four compounds significantly decreased the secretion of tumor necrosis factor-alpha (TNF-α), prostaglandin E2 (PGE2), and interleukin 6 (IL-6) in lipopolysaccharide-activated RAW 264.7 cells. Furthermore, compound 7 decreased the expression of the proteins cyclooxygenase-2 (COX-2), inducible nitric-oxide synthase (iNOS), and nuclear factor kappa-B (NF-κB/p65). In addition, the structure-activity relationships of the isolates were investigated. The results suggest that 3,4-seco-dammarane triterpenoid saponins may be used as potential anti-inflammatory drugs and warrant further investigation.
- Deng, Shengping,Hao, Lili,Huang, Xishan,Huang, Yan,Li, Chenguo,Li, Jun,Liu, Wei,Su, Shanshan,Xu, Xia,Yang, Ruiyun,Zhang, Gaorong,Zhou, Dexiong
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p. 2041 - 2053
(2020/03/06)
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- Hypoglycemic triterpenoid glycosides from Cyclocarya paliurus (Sweet Tea Tree)
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Four new rarely occurred seco-dammarane triterpenoid glycosides (1–4) and four new dammarane triterpenoid glycosides (5–8), along with four known triterpenoids (9–12), were isolated from the 70% ethanol extract of the leaves of Cyclocarya paliurus (family Juglandaceae). Their structures were elucidated by extensive spectroscopic methods, including 1D/2D NMR and HRESIMS data, together with chemical analysis and DFT GIAO 13C NMR calculation. In bioassay, compounds 5–8 significantly increased glucose consumption in 3T3-L1 adipocytes, which could be the bioactive constituents for the anti-diabetes effect of the traditional usage of C. paliurus.
- Chen, Zuhui,Li, Jing,Lv, Wenyan,Sun, Huihui,Tan, Jie,Wang, Wenxuan,Wu, Jianping,Xu, Jialing,Xu, Kangping,Xuan, Tongyao,Yang, Zhichun,Ye, Zijun,Zhu, Hui,Zou, Zhenxing
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- Two novel non-holostane type glycosides from the viscera of sea cucumber Apostichopus japonicus
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Two novel glycosides, apostichoposide A1 (1) and B1 (2), were isolated from the viscera of Chinese sea cucumbers (Apostichopus japonicus, Selenka) collected in the Bohai sea. Both the isolated glycosides were characterized by non-holostane type aglycones having 18(16)-lactone and 7(8)-double bond. Cytotoxic activities of the two compounds were evaluated against three human cancer cell lines. Compound 1 had adequate cytotoxic activity against MGC-803 and PC-3M cell lines. Our results indicated that glycosides present in A. japonicus viscera are an important high value resource for biotechnological applications.
- Zhang, Xuan-Ming,Han, Li-Wen,Sheng, Wen-Long,Li, Xiao-Bin,Zhang, Shan-Shan,Guo, Jing-Lan,Lin, Hou-Wen,Liu, Ke-Chun
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p. 329 - 337
(2019/06/27)
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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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- Antioxidant Activity of Compounds Isolated from Elaeagnus umbellata Promotes Human Gingival Fibroblast Well-Being
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Four new triterpenoid bidesmosidic saponins (1-4) and a sesquiterpenoid glucoside (5), together with nine known phenolic compounds (6-14), were isolated from the fruits of Elaeagnus umbellata. Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry data. The antioxidant capability of the isolated compounds was evaluated in human gingival fibroblasts. Compound 6 decreased ROS production and promoted cell proliferation. It also counteracted the cell cycle blockade induced by a low concentration of H2O2 decreasing the expression of p21 and CDKN2A (p16INK4A). Compound 6 decreased the expression of inflammatory cytokines (IL-6 and IL-8) in response to inflammatory stimuli, supporting its possible use in periodontitis lesions.
- Braca, Alessandra,Camangi, Fabiano,De Leo, Marinella,De Tommasi, Nunziatina,Giacomelli, Chiara,Iannuzzi, Anna Maria,Martini, Claudia,Pietrobono, Deborah,Trincavelli, Maria Letizia
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- New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.
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Five new triterpenoid saponin glycosides, trichocucumerisides A-E (1-5), together with eleven known compounds (6-16) were isolated from Trichosanthes cucumerina fruit fibers. The structures of the new compounds were elucidated by detailed analysis of NMR and mass spectroscopic data as well as chemical reactions. The anti-inflammatory study against nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells shows that compounds 7 and 9 exhibited stronger NO inhibitory activity, with IC50 values of 3.0 and 2.7 μM, respectively, with comparison to positive references Celecoxib and aminoguanidine (IC50 values 75.7 and 75.0 μM, respectively). Compounds 7 and 9 also possessed a greater selectivity index (SI) of approximately 3-4-fold activity than that of the positive references.
- Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun
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p. 10461 - 10470
(2020/03/27)
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- A rare diketopiperazine glycoside from marine-sourced Streptomyces sp. ZZ446
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Two diketopiperazines were isolated from a culture of the marine-derived actinomycete Streptomyces sp. ZZ446. Their structures were elucidated as maculosin (1) and maculosin-O-α-L-rhamnopyranoside (2) based on their NMR and HRESIMS data, specific rotation, and chemical degradation. Maculosin-O-α-L-rhamnopyranoside (2) is a new diketopiperazine glycoside, a structural class not reported previously from the natural sources. Both compounds showed antimicrobial activity against methicillin-resistant Staphylococcus aureus, Escherichia coli, and Candida albicans with MIC values in a range from 26.0 to 37.0 μg/mL. (Figure presented.).
- Chen, Mengxuan,Chen, Sangluo,Lian, Xiao-Yuan,Zhang, Di,Zhang, Zhizhen
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supporting information
p. 1046 - 1050
(2019/01/04)
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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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- Bufadienolide glycosides and bufadienolides from the whole plants of Helleborus lividus, and their cytotoxic activity
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Cytotoxicity-guided fractionation of the MeOH extract of Helleborus lividus Aiton ex Curtis (Ranunculaceae) resulted in the isolation of five undescribed bufadienolide glycosides and two undescribed bufadienolides, along with three known compounds. Their structures were determined by detailed spectroscopic analysis and hydrolysis studies. The isolated compounds showed cytotoxicity against HL-60 human leukemia cells and A549 human lung adenocarcinoma cells, with IC50 values ranging from 2.20 ± 0.01 nM to 0.77 ± 0.01 μM. The undescribed compound 3β-[(O-β-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl)oxy]-14β,16β-dihydroxy-5β-bufa-20,22-dienolide induced apoptosis in HL-60 cells via a mitochondria-dependent apoptotic pathway. The average IC50 values of bufadienolide monorhamnosides for HL-60 and A549 cells were 10–20 times lower than those for Na+/K+ ATPase, implying that they induce tumor cell death via a mechanism of action other than Na+/K+ ATPase inhibition.
- Iguchi, Tomoki,Mimaki, Yoshihiro,Takano, Shingo,Tamura, Naoya,Yokosuka, Akihito
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- Antiproliferative activity of new pentacyclic triterpene and a saponin from: Gladiolus segetum Ker-Gawl corms supported by molecular docking study
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A new triterpenoidal saponin identified as 3-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-xylopyranosyl]-2β,3β,16α-trihydroxyolean-12-en-23,28-dioic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-α-l-rhamnopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranoside 1 together with a new oleanane triterpene identified as 2β,3β,13α,22α-tetrahydroxy olean-23,28-dioic acid 2 and 6 known compounds (3-8) have been isolated from Gladiolus segetum Ker-Gawl corms. The structural elucidation of the isolated compounds was confirmed using different chemical and spectroscopic methods, including 1D and 2D NMR experiments as well as HR-ESI-MS. Moreover, the in vitro cytotoxic activity of the fractions and that of the isolated compounds 1-8 were investigated against five human cancer cell lines (PC-3, A-549, HePG-2, MCF-7 and HCT-116) using doxorubicin as a reference drug. The results showed that the saponin fraction exhibited potent in vitro cytotoxic activity against the five human cancer cell lines, whereas the maximum activity was exhibited against the PC-3 and A-549 cell lines with the IC50 values of 1.13 and 1.98 μg mL-1, respectively. In addition, compound 1 exhibited potent activity against A-549 and PC-3 with the IC50 values of 2.41 μg mL-1 and 3.45 μg mL-1, respectively. Interestingly, compound 2 showed the maximum activity against PC-3 with an IC50 of 2.01 μg mL-1. These biological results were in harmony with that of the molecular modeling study, which showed that the cytotoxic activity of compound 2 might occur through the inhibition of the HER-2 enzyme.
- Abd El-Kader, Adel M.,Abdelmohsen, Usama Ramadan,Hajjar, Dina,Hayallah, Alaa M.,Mahmoud, Basma Khalaf,Mohamed, Mamdouh F. A.
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p. 22730 - 22741
(2020/07/03)
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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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- New prenylflavonol glycosides with xanthine oxidase inhibitory activity from the leaves of Cyclocarya paliurus
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Eight new prenylflavonol glycosides (1–8), along with five known analogues (9–13) were isolated from the n-butanol extract of the dried leaves of Cyclocarya paliurus (family Juglandaceae) for the first time. The structures of these compounds were characte
- Chang, Xi-Wen,Chen, Zu-Hui,He, Xiao-Ai,Li, Jing,Lv, Wen-Yan,Sun, Hui-Hui,Tan, Jie,Wang, Wen-Xuan,Wu, Jian-Ping,Xu, Kang-Ping,Ye, Zi-Jun,Zhu, Gang-Zhi,Zhu, Hui
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- Laxative Metabolites from the Leaves of Moringa oleifera
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Three new flavonoids, quercetin-3-O-6-[methyl-(S)-3-hydroxy-3-methylglutaroyl(1→6]-β-d-glucopyranoside (1), kaempferol-3-O-[methyl-(S)-3-hydroxy-3-methylglutaroyl(1→6)]-β-d-glucopyranoside (2), and quercetin-3-O-6-[(E)-4-methoxy-5-methylhexa-2,4-dienoatyl(1→6)]-β-d-glucopyranoside (3), and two new alkaloids, 5-dehydroxymethyl-pyrrolemarumine 4″-O-α-l-rhamnopyranoside (4) and N1-methyl-N2-((4-O-α-l-rhamnopyranoside)benzyl) oxalamide (5), together with 45 known compounds (6-50) were isolated from the leaves of Moringa oleifera Lam. Among those compounds, 1-octacosanol (50), a straight-chain 28-carbon alcohol, exhibited good activity against diphenoxylate-induced constipation in mice, which is obtained as a laxative constituent from the plant for the first time. In order to have an accurate understanding of the content of compound 50, a quantification with gas chromatography-tandem mass spectrometry (GC-MS/MS) was carried out. The anti-inflammatory and α-glucosidase inhibitory activity of some compounds also was assessed.
- Huang, Xiang-Zhong,Jiang, Meng-Yuan,Li, Yan-Hong,Lu, Huai,Pu, Xiao-Yun,Tian, Kai,Wang, Wei,Xiong, Yong
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p. 7850 - 7860
(2020/09/01)
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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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- 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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- Cytotoxic Secondary Metabolites from the Endolichenic Fungus Hypoxylon fuscum
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As part of our search for new cytotoxic and antimicrobial natural products from endolichenic fungi, 19 compounds including 1 new 10-member lactone (2), 1 new polyacetylene glycoside (3), 1 new brasilane-type sesquiterpenoid glycoside (4), and 2 isobenzofuran-1(3H)-one derivatives (5 and 6) were isolated from the solid culture of the endolichenic fungus Hypoxylon fuscum. Their structures were unambiguously elucidated by NMR spectroscopic data, MS, ECD (electronic circular dichroism) calculation, and chemical methods. The cytotoxic effects on K562, SW480, and HEPG2 cell lines and the antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Candida albicans were assessed. Compounds 1, 2, and 5 exhibited moderate cytotoxicity against K562, SW480, and HEPG2 cell lines while compounds 1, 9, and 11 displayed weak antibacterial activity against S. aureus.
- Basnet, Buddha Bahadur,Chen, Baosong,Suleimen, Yerlan Melsuly,Ma, Ke,Guo, Shouyu,Bao, Li,Huang, Ying,Liu, Hongwei
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p. 1088 - 1097
(2019/08/30)
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- New C,O-Glycosylflavones from Melandrium divaricatum
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The aerial part of Melandrium divaricatum Fenzl (Caryophyllaceae) afforded 11 glycosylflavones including two new compounds that were characterized using UV, IR, and NMR spectroscopy and mass spectrometry as apigenin-6-C-(2″ -O-α-L-rhamnopyranosyl)-β-D-glucopyranoside-7-O-(6″″ -O-feruloyl)-β-Dglucopyranoside (divarioside A, 1) and apigenin-6-C-(2″-O-D-glucopyranosyl)- β-D-glucopyranoside-7-O-(6″″-O-feruloyl)- β-D-glucopyranoside (divarioside B, 2).
- Olennikov,Chirikova
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p. 1032 - 1038
(2019/11/26)
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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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- Lebbeckoside C, a new triterpenoid saponin from the stem barks of Albizia lebbeck inhibits the growth of human glioblastoma cells
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One new acacic acid-type saponin, named lebbeckoside C (1), was isolated from the stem barks of Albizia lebbeck. Its structure was established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as 3-O-[β-d-xylopyranosyl-(l→2)-β-d-fucopyranosyl-(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl]-21-O-{(2E,6S)-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-d-quinovopyranosyl)octa-2,7-dienoyl]-β-d-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28 O-[β-d-quinovopyranosyl-(l→3)-[α-l-arabinofuranosyl-(l→4)]-α-l-rhamnopyranosyl-(l→2)-β-d-glucopyranosyl] ester. The isolated saponin (1) displayed significant cytotoxic activity against the human glioblastoma cell line U-87 MG and TG1 stem-like glioma cells isolated from a patient tumor with IC50 values of 1.69 and 1.44?μM, respectively.
- Noté, Olivier Placide,Ngo Mbing, Joséphine,Kilhoffer, Marie-Claude,Pegnyemb, Dieudonné Emmanuel,Lobstein, Annelise
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p. 2292 - 2299
(2018/02/26)
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- Congmujingnosides B-G, triterpene saponins from the stem of Aralia chinensis and their protective effects against H2O2-induced myocardial cell injury
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Phytochemical investigation of the stem of Aralia chinensis yielded six new oleanane-type triterpene saponins named as congmujingnosides B-G (1–6). The new ones were elucidated on the basis of the chemical and spectroscopic analysis. Protective effects of compounds 1?6 were tested against H2O2-induced H9c2 cardiomyocyte injury, and the data showed that compounds 1 and 5 had significant cell-protective effects. No significant DPPH radical scavenging activity was observed for compounds 1?6.
- Zhang, Wen,Zhu, Nailiang,Hu, Meigeng,Yu, Shichun,Sun, Zhonghao,Wu, Haifeng,Li, Pengfei,Yang, Junshan,Ma, Guoxu,Xu, Xudong
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p. 500 - 505
(2017/11/15)
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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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- Antiangiogenic phenylpropanoid glycosides from Gynura cusimbua
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A new phenylpropanoid glycoside, named α-L-rhamnopyranosyl-(1?2)-β-D-[4″-(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate, 1″-O-(7S)-7-(3,4-dihydroxyphenyl)-7-methoxy-ethyl]-glucopyranoside (1), together with nine known compounds (2–10) were isolated from the active fraction (n-Butanol fraction) of Gynura cusimbua for the first time. The known compounds (2–10) were identified as phenylpropanoid glycosides on the basis of extensive spectral data and references. The antiangiogenic activities of compounds (1–10) were evaluated by MTT assay on HUVECs and wild-type zebrafish in vivo model assay. As a result, compounds 1, 6, 7, 8 and 10 exhibited certain antiangiogenic activities.
- Ma, Qinge,Wei, Rongrui,Zhou, Bin,Sang, Zhipei,Liu, Wenmin,Cao, Zhongling
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p. 457 - 463
(2017/10/26)
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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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- Three new cytotoxic oleanane triterpenoid saponins from Cylindrokelupha dalatensis
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Three new minor oleanane triterpenoid saponins, cylindrosides B (1), C (2), and D (3), were isolated from the seed of Cylindrokelupha dalatensis using chromatographic method. Their structures were established on the basis of the chemical and spectroscopic evidences. They displayed significant antitumor activity in vitro against HL60 cancer cell lines and IC50 values were 7.15?±?0.63, 10.07?±?0.97, and 4.74?±?0.57?μM, respectively, by MTT method.
- Yan, Meng-Yun,Liu, Jie,Xing, Shuang,Xiong, Guo-Ling,Pei, Ling-Peng,Ma, Bai-Ping,Liu, Ping,Zhou, Wen-Bin
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p. 770 - 780
(2017/11/15)
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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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- New C-2 diastereomers of flavanone glycosides conjugated with 3-hydroxy-3-methylglutaric acid from the pericarp of Citrus grandis (L.) Osbeck
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Two new 3-hydroxy-3-methylglutaryl (HMG) flavanone 7-O-diglycosides, cigranosides A and B (1 and 2), the known naringenin 7-(2′′-α-rhamnosyl-6′′-(3′′′′-hydroxy-3′′′′-methylglutaryl)-glucoside (melitidin, 3), their common biosynthetic precursor flavanone 7-O-diglycoside (naringin, 4), and one known flavone 7-O-diglycoside (rhoifolin, 5) were isolated from the pericarp of Citrus grandis (L.) Osbeck. The structures of these compounds were elucidated by spectroscopic and chemical techniques. The relative ratios and absolute configurations of the C-2 diastereomers of compounds 1, 2 and 4 were determined by online normal-phase HPLC-CD using a Chiralcel column. The absolute configuration of the HMG fragment in compounds 1–3 was assigned to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. The NO inhibitory activities of compounds 1–5 were evaluated using lipopolysaccharide-induced RAW264.7 cells. Compounds 1–5 were not cytotoxic to RAW264.7 cells at 10 μM.
- Ma, Shuang-Gang,Wang, Ru-Bing,Li, Wen-Rui,Liu, Yun-Bao,Qu, Jing,Li, Yong,Wang, Xiao-Jing,Xu, Song,Yu, Shi-Shan
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p. 519 - 524
(2018/07/25)
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- Pro-apoptotic activity of new triterpenoid saponins from the roots of Albizia adianthifolia (Schumach.) W.Wight
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As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides G–I (1–3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-β-D-xylopyranosyl-(1 → 3)-[5-O-acetyl-α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1), 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (2), and 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (3). The apoptotic effect of saponins 1–3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1–3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
- Noté, Olivier Placide,Kamto, Eutrophe Le Doux,Toukea, Daniel Djou,Aouazou, Sarah Ali,Mbing, Joséphine Ngo,Muller, Christian Dominique,Guillaume, Dominique,Pegnyemb, Dieudonné Emmanuel
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- Oleanane-type glycosides from the roots of Weigela florida “rumba” and evaluation of their antibody recognition
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Three triterpene glycosides were isolated from the roots of Weigela florida “rumba” (Bunge) A. DC.: two previously undescribed 3-O-β-D-xylopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→4)]-β-D-xylopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-
- Champy-Tixier, Anne-Sophie,Mitaine-Offer, Anne-Claire,Real Fernández, Feliciana,Miyamoto, Tomofumi,Tanaka, Chiaki,Papini, Anna-Maria,Lacaille-Dubois, Marie-Aleth
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p. 198 - 203
(2018/05/29)
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- Optimization of ultrasound-assisted extraction of okra (Abelmoschus esculentus (L.) Moench) polysaccharides based on response surface methodology and antioxidant activity
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This study determined the optimal conditions for ultrasound-assisted extraction of a water-soluble polysaccharide, Raw Okra Polysaccharide, from the fruit of okra using response surface methodology. The optimal extraction temperature, extraction time and ultrasonic power were 59 °C, 30 min and 522 W, respectively, giving a yield of 10.35 ± 0.11%. ROP was further isolated, lyophilized and purified using a DEAE-Sepharose Fast Flow column and Sepharose CL-6B column, revealing three elution peaks subsequently designated ROP ?1, ?2, and ?3, respectively. Of these, ROP-2 showed the highest yield, and was therefore selected for physicochemical analysis and evaluation of antioxidant activity. Gas chromatography, fourier transform infrared spectroscopy, and high-performance liquid chromatography were used to characterize the primary structural features and molecular weight, revealing that ROP-2 is composed of glucose, mannose, galactose, arabinose, xylose, fructose, and rhamnose (molar percentages: 28.8, 12.5, 13.1, 15.9, 9.2, 13.7, and 6.8%, respectively) and has an average molecular weight of 1.92 × 105 Da. A superoxide radical scavenging assay and DPPH radical scavenging assay further revealed the significant in vitro antioxidant activity of ROP-2. These findings present an effective technique for extraction of the natural antioxidant ROP-2, warranting further analysis of its potential application in the food industry.
- Wang, Kunli,Li, Mo,Wen, Xin,Chen, Xiaosong,He, Zhengyu,Ni, Yuanying
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p. 1056 - 1063
(2018/04/12)
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- New dammarane triterpenoid saponins from the leaves of Cyclocarya paliurus
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Three new dammarane triterpenoid saponins, cyclocariosides O-Q (1–3), were isolated from the ethanolic extracts of the leaves of Cyclocarya paliurus. The structures of these compounds were elucidated by spectroscopic methods.
- Wang, Yi-Rui,Cui, Bao-Song,Han, Shao-Wei,Li, Shuai
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- Flavonoid glycosides from Sedum bulbiferum
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The MeOH extract from dried whole Sedum bulbiferum MAKINO (Crassulaceae) plants yielded 34 compounds, including six new flavonoid glycosides and 28 known compounds. The structures of new compounds were established using NMR, Mass spectroscopic analysis an
- Warashina, Tsutomu,Miyase, Toshio
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p. 1199 - 1204
(2017/12/26)
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- Triterpenoids from Cyclocarya paliurus and their inhibitory effect on the secretion of apoliprotein B48 in Caco-2 cells
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Five previously undescribed compounds including two triterpenoid aglycones, 3β,23-dihydroxy-1,12-dioxo-olean-28-oic acid and 3β,23,27-trihydroxy-1-oxo-olean-12-ene-28-oic acid, and three triterpenoid glucosides cyclocarioside L-N, along with 17 known compounds were isolated from a CH3Cl-soluble extract of the leaves of Cyclocarya paliurus. Two 27-nor-triterpenoid glycosides were isolated from the genus for the first time. Furthermore, the characterized compounds were tested for the inhibitory effects on apoliprotein B48 secretion in Caco-2 cells. Seven triterpenoid aglycones together with four triterpenoid saponins significantly decreased the apoliprotein B48 oversecretion induced by oleic acid in Caco-2 cells.
- Wu, Zheng-Feng,Meng, Fan-Cheng,Cao, Lan-Jie,Jiang, Cui-Hua,Zhao, Meng-Ge,Shang, Xu-Lan,Fang, Sheng-Zuo,Ye, Wen-Cai,Zhang, Qing-Wen,Zhang, Jian,Yin, Zhi-Qi
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