7658-08-4Relevant articles and documents
Chain conformations and steady-shear viscosity properties of pectic polysaccharides from apple and tomato
Hu, Shihao,Nie, Shaoping,Wang, Junqiao,Wang, Qiang,Xu, Xiaojuan
, (2022/04/03)
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.
Cytotoxic triterpene and steroidal glycosides from the seeds of Digitalis purpurea and the synergistic cytotoxicity of steroidal glycosides and etoposide in SBC-3 cells
Fukaya, Haruhiko,Kuroda, Minpei,Matsuo, Yukiko,Mimaki, Yoshihiro,Takatori, Kazuhiro,Tsuchihashi, Hiroko
, (2022/03/27)
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
Four new prenylflavonol glycosides from the leaves of Cyclocarya paliurus
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
, p. 772 - 779 (2020/08/10)
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,
A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential
Huang, Linlin,Li, Fei,Li, Quanhong,Liang, Li,Wei, Yunlu,Yu, Guoyong
, (2020/10/02)
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.
α-Glucosidase inhibitory and anti-inflammatory activities of dammarane triterpenoids from the leaves of Cyclocarya paliurus
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
supporting information, (2021/07/22)
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.
Neuroprotective and anti-inflammatory phenylethanoid glycosides from the fruits of Forsythia suspensa
Feng, Zi-Meng,Jiang, Jian-Shuang,Shao, Si-Yuan,Yang, Ya-Nan,Zhang, Fan,Zhang, Pei-Cheng
, (2021/06/15)
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.
Two new triterpenoid glycosides from leaves of Cyclocarya paliurus
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
, (2021/05/31)
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
A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities
Han, Hua,Qi, Xin-Rui,Shen, Li,Tang, Hai-Feng,Xu, Qiang-Zhi,Yang, Wen-Sheng,Yi, Yang-Hua,Yuan, Chun-Hong
, (2021/05/21)
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.
Two new iridoid glycosides from Gardeniae Fructus
Shu, Penghua,Yu, Mengzhu,Zhu, Huiqing,Luo, Yuehui,Li, Yamin,Li, Nianci,Zhang, Hui,Zhang, Jialong,Liu, Guangwei,Wei, Xialan,Yi, Wenhan
, (2021/02/26)
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%).
New triterpene glycosides from the far eastern starfish solaster pacificus and their biological activity
Malyarenko, Timofey V.,Kicha, Alla A.,Kalinovsky, Anatoly I.,Dmitrenok, Pavel S.,Malyarenko, Olesya S.,Kuzmich, Alexandra S.,Stonik, Valentin A.,Ivanchina, Natalia V.
, p. 1 - 15 (2021/03/17)
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.
