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27740-01-8 | β-D-Glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
CAS No: 27740-01-8 Catalog No: AG002UML MDL No:MFCD01861503
Product Description
Catalog Number:
AG002UML
Chemical Name:
β-D-Glucopyranosiduronic acid, 5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl
CAS Number:
27740-01-8
Molecular Formula:
C21H18O12
Molecular Weight:
462.3604
MDL Number:
MFCD01861503
IUPAC Name:
(2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI:
InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChI Key:
DJSISFGPUUYILV-ZFORQUDYSA-N
SMILES:
OC(=O)[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
UNII:
16IGP0ML9A
Properties
Complexity:
777
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
5
Defined Bond Stereocenter Count:
0
Exact Mass:
462.08g/mol
Formal Charge:
0
Heavy Atom Count:
33
Hydrogen Bond Acceptor Count:
12
Hydrogen Bond Donor Count:
7
Isotope Atom Count:
0
Molecular Weight:
462.363g/mol
Monoisotopic Mass:
462.08g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
203A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.8
Literature
| Title | Journal |
|---|---|
| In vitro effects of some flavones on human pyruvate kinase isoenzyme M2. | Journal of biochemical and molecular toxicology 20150301 |
| Scutellarin inhibits high glucose-induced and hypoxia-mimetic agent-induced angiogenic effects in human retinal endothelial cells through reactive oxygen species/hypoxia-inducible factor-1α/vascular endothelial growth factor pathway. | Journal of cardiovascular pharmacology 20140901 |
| Synthesis and protective effect of scutellarein on focal cerebral ischemia/reperfusion in rats. | Molecules (Basel, Switzerland) 20120906 |
| Scutellarin inhibits cytochrome P450 isoenzyme 1A2 (CYP1A2) in rats. | Phytotherapy research : PTR 20120801 |
| Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13. | Bioorganic & medicinal chemistry letters 20120615 |
| Research on scutellarin parenteral solution's protective effects in rats with severe acute pancreatitis and multiple organ injuries. | Inflammation 20120601 |
| [Scutellarin starch microspheres' permeability through nasal mucosa of different animals in vitro]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120301 |
| Scutellarin inhibits translocation of protein kinase C in diabetic thoracic aorta of the rat. | Clinical and experimental pharmacology & physiology 20120201 |
| [Simultaneous determination of isoorientin, scutellarin and cynaroside in rat plasma and pharmacokinetics by UPLC-MS/MS]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20120201 |
| Neuroprotective effects of scutellarin against hypoxic-ischemic-induced cerebral injury via augmentation of antioxidant defense capacity. | The Chinese journal of physiology 20111231 |
| Preparation, characterization and evaluation of breviscapine lipid emulsions coated with monooleate-PEG-COOH. | International journal of pharmaceutics 20111215 |
| Scutellarin protects against Aβ-induced learning and memory deficits in rats: involvement of nicotinic acetylcholine receptors and cholinesterase. | Acta pharmacologica Sinica 20111201 |
| Comparative studies on interactions of baicalein, baicalin and scutellarin with lysozyme. | European journal of medicinal chemistry 20111201 |
| Scutellarin-dependent inhibition of collagen biosynthesis in cultured fibroblasts. | Natural product research 20111101 |
| Absorption and disposition of scutellarin in rats: a pharmacokinetic explanation for the high exposure of its isomeric metabolite. | Drug metabolism and disposition: the biological fate of chemicals 20111101 |
| [Simultaneous determination of protocatechuic acid, isoorientin and scutellarin in rat tissues after a single intravenous administration of compound hongcao for injection by UPLC-MS/MS]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111101 |
| Flavonoids in Scutellaria immaculata and S. ramosissima (Lamiaceae) and their biological activity. | The Journal of pharmacy and pharmacology 20111001 |
| Scutellarin benzyl ester partially secured the ischemic injury by its anti-apoptosis mechanism in cardiomyocytes of neonatal rats. | Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20110901 |
| Intestinal transport of scutellarein and scutellarin and first-pass metabolism by UDP-glucuronosyltransferase-mediated glucuronidation of scutellarein and hydrolysis of scutellarin. | Xenobiotica; the fate of foreign compounds in biological systems 20110701 |
| Neuroprotection of Scutellarin is mediated by inhibition of microglial inflammatory activation. | Neuroscience 20110630 |
| Scutellarin blocks sodium current in freshly isolated mouse hippocampal CA1 neurons. | Neurochemical research 20110601 |
| Acute and subacute toxicological evaluation of scutellarin in rodents. | Regulatory toxicology and pharmacology : RTP 20110601 |
| Effects of scutellarin on MUC5AC mucin production induced by human neutrophil elastase or interleukin 13 on airway epithelial cells. | Journal of Korean medical science 20110601 |
| [Effect of scutellarin on expressions of nicotinic acetylcholine receptor protein and mRNA in the brains of dementia rats]. | Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine 20110601 |
| Metabolic and pharmacokinetic studies of scutellarin in rat plasma, urine, and feces. | Acta pharmacologica Sinica 20110501 |
| [Studies on the chemical constituents from Conyza canadensis]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110501 |
| Flavonoid composition of Juniperus oblonga Bieb. | Bulletin of experimental biology and medicine 20110401 |
| [Effect of pravastatin on transportation of scutellarin in mouse liver and its mechanism]. | Yao xue xue bao = Acta pharmaceutica Sinica 20110301 |
| Scutellarin alleviates interstitial fibrosis and cardiac dysfunction of infarct rats by inhibiting TGFβ1 expression and activation of p38-MAPK and ERK1/2. | British journal of pharmacology 20110201 |
| [Influence of scutellarin on oxidative stress and neuronal apoptosis of rats with dementia]. | Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20110201 |
| [Determination of four effective components from total flavonoids of Scutellaria barbata by high performance liquid chromatography]. | Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20110101 |
| Scutellarin attenuates human-neutrophil-elastase-induced mucus production by inhibiting the PKC-ERK signaling pathway in vitro and in vivo. | The American journal of Chinese medicine 20110101 |
| Synthesis and bio-activity evaluation of scutellarein as a potent agent for the therapy of ischemic cerebrovascular disease. | International journal of molecular sciences 20110101 |
| Scutellarin inhibits cell migration by regulating production of αvβ6 integrin and E-cadherin in human tongue cancer cells. | Oncology reports 20101101 |
| Scutellarin promotes in vitro angiogenesis in human umbilical vein endothelial cells. | Biochemical and biophysical research communications 20100910 |
| [Absorption and transportation characteristics of scutellarin and scutellarein across Caco-2 monolayer model]. | Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine 20100901 |
| [Evaluation of brain-targeted trendence of scutellarin nasal administration]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20100901 |
| PEG-scutellarin prodrugs: synthesis, water solubility and protective effect on cerebral ischemia/reperfusion injury. | European journal of medicinal chemistry 20100501 |
| Scutellarin protects against lipopolysaccharide-induced acute lung injury via inhibition of NF-kappaB activation in mice. | Journal of Asian natural products research 20100301 |
| Scutellarin exerts its anti-hypertrophic effects via suppressing the Ca2+-mediated calcineurin and CaMKII signaling pathways. | Naunyn-Schmiedeberg's archives of pharmacology 20100201 |
| Selective fraction of Scutellaria baicalensis and its chemopreventive effects on MCF-7 human breast cancer cells. | Phytomedicine : international journal of phytotherapy and phytopharmacology 20100101 |
| [Advances in studies on pharmacokinetics of scutellarin and scutellarein]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091201 |
| Metabolism profile of scutellarin in urine following oral administration to rats by ultra performance liquid chromatography coupled to time-of-flight mass spectrometry. | Talanta 20091115 |
| Estrogenic and neuroprotective properties of scutellarin from Erigeron breviscapus: a drug against postmenopausal symptoms and Alzheimer's disease. | Planta medica 20091101 |
| Suppression of diet-induced hypercholesterolemia by scutellarin in rats. | Planta medica 20090901 |
| Scutellarin sensitizes drug-evoked colon cancer cell apoptosis through enhanced caspase-6 activation. | Anticancer research 20090801 |
| [Effects of doubled CO2 concentration on Erigeron breviscapus growth and its active constituent accumulation]. | Ying yong sheng tai xue bao = The journal of applied ecology 20090801 |
| [Effect of water stress on content of active constituents in Erigeron breviscaps]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090501 |
| Protective effects of scutellarin against cerebral ischemia in rats: evidence for inhibition of the apoptosis-inducing factor pathway. | Planta medica 20090201 |
| Nitric oxide and catalase-sensitive relaxation by scutellarin in the mouse thoracic aorta. | Journal of cardiovascular pharmacology 20090101 |
| Separation and purification of two flavone glucuronides from Erigeron multiradiatus (Lindl.) Benth with macroporous resins. | Journal of biomedicine & biotechnology 20090101 |
| [Study on optimal harvest time of Erigeron breviscapus]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20081201 |
| Simultaneous determination of five main active constituents of Erigeron multiradiatus by HPLC-DAD-MS. | Journal of pharmaceutical and biomedical analysis 20081104 |
| Pulmonary delivery of scutellarin solution and mucoadhesive particles in rats. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20081101 |
| Scutellarin-induced endothelium-independent relaxation in rat aorta. | Phytotherapy research : PTR 20081101 |
| Anti-inflammatory activity of the extracts and fractions from Erigeron multiradiatus through bioassay-guided procedures. | Journal of ethnopharmacology 20080926 |
| Scutellarin isolated from Erigeron multiradiatus inhibits high glucose-mediated vascular inflammation. | Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20080901 |
| Comparative pharmacokinetics of breviscapine liposomes in dogs, rabbits and rats. | International journal of pharmaceutics 20080709 |
| [HPLC determination of four active components in dengzhanxixin injection]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080701 |
| Effect of ion-pairing and enhancers on scutellarin skin permeability. | The Journal of pharmacy and pharmacology 20080401 |
| [Optimizing extraction process of Scutellaria barbata by golden section method]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20080401 |
| Plant regeneration of Erigeron breviscapus (vant.) Hand. Mazz. and its chromatographic fingerprint analysis for quality control. | Plant cell reports 20080101 |
| Mrp2-related efflux of scutellarin in the intestinal absorption in rats. | Die Pharmazie 20080101 |
| Scutellarin induced Ca(2+ ) release and blocked KCl-induced Ca(2+ ) influx in smooth muscle cells isolated from rat thoracic artery. | Journal of Asian natural products research 20080101 |
| The promoting angiogenesis and anti-inflammation effect of scutellarin on polyglycolic acid scaffold of balb/c mice model. | Journal of Asian natural products research 20080101 |
| Effects of scutellarin on apoptosis induced by cobalt chloride in PC12 cells. | The Chinese journal of physiology 20071231 |
| Separation of scutellarin from crude extracts of Erigeron breviscapus (vant.) Hand. Mazz. by macroporous resins. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20071015 |
| Effects of scutellarin on PKCgamma in PC12 cell injury induced by oxygen and glucose deprivation. | Acta pharmacologica Sinica 20071001 |
| Protective effects of scutellarin and breviscapine on brain and heart ischemia in rats. | Journal of cardiovascular pharmacology 20070901 |
| [Pharmacokinetic and tissue distribution study of scutellarin in rats]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20070801 |
| Microwave-assisted extraction of scutellarin from Erigeron breviscapus Hand-Mazz and its determination by high-performance liquid chromatography. | Analytica chimica acta 20070522 |
| Two major urinary metabolites of scutellarin in rats. | Planta medica 20070401 |
| Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death. | Journal of agricultural and food chemistry 20070321 |
| Scutellarin protects PC12 cells from oxidative stress-induced apoptosis. | Journal of Asian natural products research 20070301 |
| The protective action of scutellarin against immunological liver injury induced by concanavalin A and its effect on pro-inflammatory cytokines in mice. | The Journal of pharmacy and pharmacology 20070101 |
| Prodrugs of scutellarin: ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20061201 |
| [Study on bile excretion of scutellarein]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20061001 |
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| Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration. | Drug metabolism and disposition: the biological fate of chemicals 20060801 |
| Synthesis, characterization and in situ intestinal absorption of different molecular weight scutellarin-PEG conjugates. | Die Pharmazie 20060801 |
| Two-step purification of scutellarin from Erigeron breviscapus (vant.) Hand. Mazz. by high-speed counter-current chromatography. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060711 |
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| Determination of scutellarin in mouse plasma and different tissues by high-performance liquid chromatography. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060501 |
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| [Pharmacokinetics of breviscapine liposomes following intravenous injection in Beagle dogs]. | Yao xue xue bao = Acta pharmaceutica Sinica 20060101 |
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| The anti-HIV-1 effect of scutellarin. | Biochemical and biophysical research communications 20050902 |
| The physicochemical characteristics of freeze-dried scutellarin-cyclodextrin tetracomponent complexes. | Drug development and industrial pharmacy 20050901 |
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| [Effect of caffeic acid, seopoletin and scutellarin on rat retinal neurons in vitro]. | Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050601 |
| A possible quantitative method to improve the sensitivity of scutellarin in human plasma. | Annali di chimica 20050601 |
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| In vitro studies of baicalin alone or in combination with Salvia miltiorrhiza extract as a potential anti-cancer agent. | International journal of oncology 20050101 |
| Pharmacokinetics of scutellarin and its aglycone conjugated metabolites in rats. | European journal of drug metabolism and pharmacokinetics 20050101 |
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| Scutellarin attenuates oxidative glutamate toxicity in PC12 cells. | Planta medica 20040501 |
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| Probing the binding of scutellarin to human serum albumin by circular dichroism, fluorescence spectroscopy, FTIR, and molecular modeling method. | Biomacromolecules 20040101 |
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| Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae). | Phytochemistry 20020801 |
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