10485-94-6Relevant academic research and scientific papers
Identification of carbohydrate isomers in flavonoid glycosides after hydrolysis by hydrophilic interaction chromatography
Spackova, Vera,Pazourek, Jiri
, p. 357 - 364 (2013)
A method for carbohydrate isomers (saccharide units) identification in flavonoid glycosides after hydrolysis by an HPLC system with two detectors (diode array UV-VIS detector and evaporative light scattering detector) was set up in this work. Experimental procedure was optimized with two types of model glycosides, namely rutin and hesperidin. The model glycosides were hydrolyzed to saccharide units and aglycone parts; the aglycone was characterized by its UV-VIS spectrum and the saccharide unit was identified by its retention time and elution profile (anomeric signals). Acidic and enzymatic hydrolyses were compared in the first step of the method; in acidic hydrolysis, trifluoracetic acid was used, while glucosidase, galactosidase, and hesperidinase were used in enzymatic hydrolysis. A complete enzymatic hydrolysis was achieved with hesperidin and neohesperidin, but not with 3-O-glycosides. The method was applied for the identification of a glycone from a glycoside isolated from Polygonum lapathifolium (Polygonaceae sp.).
Hepta-, hexa-, penta-, tetra-, and trisaccharide resin glycosides from three species of Ipomoea and their antiproliferative activity on two glioma cell lines
León-Rivera, Ismael,del Río-Portilla, Federico,Enríquez, Raúl G.,Rangel-López, Edgar,Villeda, Juana,Rios, María Yolanda,Navarrete-Vázquez, Gabriel,Hurtado-Días, Israel,Guzmán-Valdivieso, Ulises,Nú?ez-Urquiza, Verónica,Escobedo-Martínez, Carolina
, p. 214 - 223 (2017)
Six new partially acylated resin glycosides were isolated from convolvulin of Ipomoea purga, Ipomoea stans, and Ipomoea murucoides (Convolvulaceae). The structures of compounds 1–6 were elucidated by a combination of NMR spectroscopy and mass spectrometry. The structure of jalapinoside B (1) consists of a hexasaccharide core bonded to an 11-hydroxytetradecanoic (convolvulinic) acid forming a macrolactone acylated by a 2-methylbutanoyl, a 3-hydroxy-2-methylbutanoyl, and a quamoclinic acid B units. Purginoic acid A (2) contains a hexasaccharide core bonded to a convolvulinic acid acylated by a 3-hydroxy-2-methylbutanoyl unit. Stansin A (4) is an ester-type heterodimer, and consists of two stansoic acid A (3) units, acylated by 2-methylbutanoic and 3-hydroxy-2-methylbutanoic acids. The site of lactonization was located at C-3 of Rhamnose, and the position for the ester linkage of the monomeric unit B on the macrolactone unit A was established as C-4 of the terminal rhamnose. Compounds 5 and 6 are glycosidic acids. Murucinic acid II (5) is composed of a pentasaccharide core bonded to an 11-hydroxyhexadecanoic (jalapinolic) acid, acylated by an acetyl unit. Stansinic acid I (6) is a tetrasaccharide core bonded to a jalapinolic acid, acylated by 2-methylbutanoyl and 3-hydroxy-2-methylbutanoyl units. Preliminary testing showed the cytotoxicity of compounds 1–6 toward OVCAR and UISO-SQC-1 cancer cell lines. In addition, compound 1 showed an antiproliferative activity on glioma C6 and RG2 tumor cell lines. Copyright
A new flavonol triglycoside derived from Anoectochilus elwesii on stimulating glucose uptake in insulin-induced human HepG2 cells
Cai, Jinyan,Zhao, Lin,Zhu, En
, p. 1414 - 1418 (2015)
A novel flavonol triglycoside (4), isorhamnetin-3-O-β-d-glucopyranosyl (1→2)-α-l-rhamnopyranosyl (1→6)-β-d-glucopyranoside, named elwesoside A, together with six known flavonols (1-3, 5-7) was isolated from Anoectochilus elwesii (Clarke ex Hook. f.) King et Pantl. and its structure was elucidated by extensive spectroscopic methods and comparison with the literature data. All compounds were first reported in this plant and two of them (4 and 5) were the first examples of flavonol triglycosides isolated from Anoectochilus genus. The effects of 1-7 were evaluated on insulin-treated human HepG2 cells under high glucose conditions for stimulating glucose uptake activities. The novel compound (4) displayed highly potent dose-dependent effect on the stimulation of glucose uptake in insulin-resistant human HepG2 cells.
Simalin A and B: Two new aromatic compounds from the stem bark of Bombax ceiba
Joshi, Khem Raj,Devkota, Hari Prasad,Yahara, Shoji
, p. 26 - 29 (2014)
Two new aromatic compounds, simalin A (1) and B (2), along with five known compounds shamiminol (3), (-)-epicatechin-7-O-β-xylopyranoside (4), (-)-catechin-7-O-β-xylopyranoside (5), (+)-isolarisiresinol-9′-O- β-glucopyranoside (6) and (+)-lyoniresinol-9′-O-β- glucopyranoside (7) were isolated from the stem bark of Bombax ceiba. Their structures were elucidated by chemical and spectral methods. Compounds 6 and 7 were isolated for the first time from B. ceiba.
Three new flavone C-glycosides from the aerial parts of Paraquilegia microphylla
Xu, Kai-Jie,Xu, Xue-Min,Deng, Wen-Long,Zhang, Lei,Wang, Ming-Kui,Ding, Li-Sheng
, p. 409 - 416 (2011)
Three new flavone C-glycosides, paraquinins A-C, were isolated from the aerial parts of Paraquilegia microphylla (Royle) Dromm. et Hutch, a Tibetan medicine distributed in the Qinghai-Tibet plateau. On the basis of 1D and 2D NMR evidence, their structures were elucidated as acacetin-6-C-β- glucopyranosyl-(1→2) -α-L-glucopyranoside (1), acacetin-6-C - β-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2) -β-D-glucopyranoside (2), and acacetin-6-C -α- L-rhamnopyranosyl- (1→2)-(6'''-O-E-feruloyl) -β-D-glucopyranosyl-(1→2) -β- D-glucopyranoside (3).
Two new spirostanol saponins from Reineckia carnea
Zhang, Zhong-Quan,Chen, Jian-Chao,Zhang, Xian-Ming,Li, Zhong-Rong,Qiu, Ming-Hua
, p. 1494 - 1499 (2008)
Two new spirostanol saponins, (1β,3β,5β,25S)-spirostan-1,3- diol 1-(β-D-xylopyranoside) (1) and (1β,3β,5β,25S)- spirostan-1,3-diol 1-[α-L-rhamnopyranosyl-(1 → 2)-β-D- fucopyranoside] (2), along with two known compounds, (1β,3β,5β, 25S)-spirostan-1,3-diol
A FLAVONOL TRIGLYCOSIDE FROM BACCHARIS THESIOIDES
Liu, Yong-Long,Timmermann, Barbara N.,Hoffmann, Joseoh J.,McLaughlin, Steven P.
, p. 1549 - 1551 (1993)
Five flavonols have been isolated from the aerial parts of Baccharis thesioides.On the basis of spectroscopic analysis the structure of a new flavonol triglycoside has been elucidated as quercetin 3-O-2)α-L-rhamnopyranosyl (1->6)>-β-D-glucopyranoside.Four known flavonols were identified as rutin, hyperoside, isoquercetin and quercetin.
Triterpenoid saponins with anti-inflammatory activities from Ilex pubescens roots
Wu, Peng,Gao, Hui,Liu, Jian-Xin,Liu, Liang,Zhou, Hua,Liu, Zhong-Qiu
, p. 122 - 132 (2017)
Seven triterpenoid saponins, named ilexsaponin I–O, along with twelve known ones, were isolated from the roots of Ilex pubescens. The structures of all compounds were elucidated by use of extensive spectroscopic methods (IR, HR-ESI-MS, and 1D and 2D NMR).
Purification, characterization and antitumor activity of polysaccharides extracted from Phellinus igniarius mycelia
Li, Shi-Chao,Yang, Xiao-Ming,Ma, Hai-Le,Yan, Jing-Kun,Guo, Dan-Zhao
, p. 24 - 30 (2015)
Abstract Water-soluble intracellular polysaccharides (IPS) were extracted from cultured mycelia of Phellinus igniarius. The IPS were purified by ethanol fractional precipitation, ion-exchange and size exclusion chromatography in that order. Homogeneous polysaccharide IPSW-1, IPSW-2, IPSW-3, and IPSW-4 were obtained, which molecular characteristics were examined using multiangle laser-light scattering and refractive index detector system. The average molecular weights of them were 34.1, 17.7, 15.1, 21.7 kDa, respectively. GC analysis indicated that IPSW-1, IPSW-2 and IPSW-3 all only contained glucose, while IPSW-4 was composed of rhamnose, xylose, mannose, glucose and galactose in a molar ratio of 1.29:1.21:1:43.86:1.86. UV and IR analysis suggested they belonged to α-type of the pyran group and didn't contain protein. These homogeneous polysaccharides could inhibit the growth of SW480 and HepG2 cells to a certain extent in a dose-dependent manner. So they could be beneficial for the further development of a natural carcinoma preventive agent and functional food.
New pregnane and phenolic glycosides from Solenostemma argel
Ounaissia, Karima,Pertuit, David,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Tanaka, Chiaki,Delemasure, Stéphanie,Dutartre, Patrick,Smati, Dalila,Lacaille-Dubois, Marie-Aleth
, p. 98 - 104 (2016)
From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1–3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D – and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9–59.0?μM. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3?μM and 27.6?μM, respectively) significantly decreased the Il-1β production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481–9617?μmol?eq. Trolox/100?g.
