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20575-57-9,MFCD00210598
Catalog No.:AA002A9J

20575-57-9 | Calycosin

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002A9J
Chemical Name:
Calycosin
CAS Number:
20575-57-9
Molecular Formula:
C16H12O5
Molecular Weight:
284.2635
MDL Number:
MFCD00210598
SMILES:
COc1ccc(cc1O)c1coc2c(c1=O)ccc(c2)O
Properties
Properties
 
BP:
536.8°C at 760 mmHg  
Form:
Solid  
MP:
245~247℃  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
432  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
2.4  

Literature

Title: Flavonoids induce the expression of acetylcholinesterase in cultured osteoblasts.

Journal: Chemico-biological interactions 20161125

Title: Regioselective glucuronidation of the isoflavone calycosin by human liver microsomes and recombinant human UDP-glucuronosyltransferases.

Journal: Chemico-biological interactions 20140905

Title: Profiling of hepatocellular carcinoma cell cycle regulating genes targeted by calycosin.

Journal: BioMed research international 20130101

Title: The membrane permeability of Astragali Radix-derived formononetin and calycosin is increased by Angelicae Sinensis Radix in Caco-2 cells: a synergistic action of an ancient herbal decoction Danggui Buxue Tang.

Journal: Journal of pharmaceutical and biomedical analysis 20121101

Title: Profiling and identification of the metabolites of calycosin in rat hepatic 9000×g supernatant incubation system and the metabolites of calycosin-7-O-β-D-glucoside in rat urine by HPLC-DAD-ESI-IT-TOF-MS(n) technique.

Journal: Journal of pharmaceutical and biomedical analysis 20121101

Title: Chemical and biological assessment of Angelica herbal decoction: comparison of different preparations during historical applications.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20120815

Title: Metabolism of calycosin, an isoflavone from Astragali Radix, in zebrafish larvae.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20120301

Title: Synergistic Apoptosis-Inducing Antileukemic Effects of Arsenic Trioxide and Mucuna macrocarpa Stem Extract in Human Leukemic Cells via a Reactive Oxygen Species-Dependent Mechanism.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Polysaccharides from astragali radix restore chemical-induced blood vessel loss in zebrafish.

Journal: Vascular cell 20120101

Title: Study of the effects of total flavonoids of Astragalus on atherosclerosis formation and potential mechanisms.

Journal: Oxidative medicine and cellular longevity 20120101

Title: Metabolomics-based optimal koji fermentation for tyrosinase inhibition supplemented with Astragalus radix.

Journal: Bioscience, biotechnology, and biochemistry 20120101

Title: Investigation of effects and mechanisms of total flavonoids of Astragalus and calycosin on human erythroleukemia cells.

Journal: Oxidative medicine and cellular longevity 20120101

Title: HPLC-MS/MS analysis of a traditional Chinese medical formulation of Bu-Yang-Huan-Wu-Tang and its pharmacokinetics after oral administration to rats.

Journal: PloS one 20120101

Title: [Effects and mechanisms of total flavonoids of astragali radix and calycosin on inhibiting human erythroleukemia cell line K562].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20111201

Title: Calycosin stimulates proliferation of estrogen receptor-positive human breast cancer cells through downregulation of Bax gene expression and upregulation of Bcl-2 gene expression at low concentrations.

Journal: JPEN. Journal of parenteral and enteral nutrition 20111101

Title: Transcriptional profiling of angiogenesis activities of calycosin in zebrafish.

Journal: Molecular bioSystems 20111101

Title: Calycosin promotes proliferation of estrogen receptor-positive cells via estrogen receptors and ERK1/2 activation in vitro and in vivo.

Journal: Cancer letters 20110928

Title: Isolation, identification and antiviral activities of metabolites of calycosin-7-O-β-D-glucopyranoside.

Journal: Journal of pharmaceutical and biomedical analysis 20110910

Title: Calycosin protects HUVECs from advanced glycation end products-induced macrophage infiltration.

Journal: Journal of ethnopharmacology 20110901

Title: [Study on HPLC chromatographic fingerprint of anti-tumor active site SSCE of Caulis spatholobi].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110901

Title: Ultraviolet irradiation induces accumulation of isoflavonoids and transcription of genes of enzymes involved in the calycosin-7-O-β-d-glucoside pathway in Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao.

Journal: Physiologia plantarum 20110701

Title: Inhibitory effects of two major isoflavonoids in Radix Astragali on high glucose-induced mesangial cells proliferation and AGEs-induced endothelial cells apoptosis.

Journal: Planta medica 20110501

Title: Determination of paeoniflorin, calycosin-7-O-β-D-glucoside, ononin, calycosin and formononetin in rat plasma after oral administration of Buyang Huanwu decoction for their pharmacokinetic study by liquid chromatography-mass spectrometry.

Journal: Biomedical chromatography : BMC 20110401

Title: Separation and sweeping of flavonoids by microemulsion electrokinetic chromatography using mixed anionic and cationic surfactants.

Journal: Talanta 20110315

Title: Flavonoids from Radix Astragali induce the expression of erythropoietin in cultured cells: a signaling mediated via the accumulation of hypoxia-inducible factor-1α.

Journal: Journal of agricultural and food chemistry 20110309

Title: Identification and determination of flavonoids in astragali radix by high performance liquid chromatography coupled with DAD and ESI-MS detection.

Journal: Molecules (Basel, Switzerland) 20110309

Title: New isoflavonoid glycosides and related constituents from astragali radix ( Astragalus membranaceus ) and their inhibitory activity on nitric oxide production.

Journal: Journal of agricultural and food chemistry 20110223

Title: Antimicrobial activities of the CH2Cl2-CH3OH (1:1) extracts and compounds from the roots and fruits of Pycnanthus angolensis (Myristicaceae).

Journal: Natural product research 20110201

Title: A chinese herbal decoction, danggui buxue tang, stimulates proliferation, differentiation and gene expression of cultured osteosarcoma cells: genomic approach to reveal specific gene activation.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: A Chinese Herbal Decoction, Dang Gui Bu Xue Tang, Prepared from Radix Astragali and Radix Angelicae sinensis, Ameliorates Insulin Resistance Induced by A High-Fructose Diet in Rats.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Attenuated cardiac mitochondrial-dependent apoptotic effects by li-fu formula in hamsters fed with a hypercholesterol diet.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Anti-inflammatory, immunomodulatory, and heme oxygenase-1 inhibitory activities of ravan napas, a formulation of uighur traditional medicine, in a rat model of allergic asthma.

Journal: Evidence-based complementary and alternative medicine : eCAM 20110101

Title: Proangiogenic activity of plant extracts in accelerating wound healing - a new face of old phytomedicines.

Journal: Acta biochimica Polonica 20110101

Title: Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin.

Journal: Molecules (Basel, Switzerland) 20101209

Title: [Simultaneous determination of nine isoflavonoids in Huangqi Gegen decoction by high performance liquid chromatography].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001

Title: [Simultaneous assay of four isoflavonoids in Astragali Radix by QAMS].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001

Title: Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose.

Journal: Journal of agricultural and food chemistry 20100922

Title: Isoflavones isolated from red clover (Trifolium pratense) inhibit smooth muscle contraction of the isolated rat prostate gland.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20100901

Title: New flavonoids with 2BS cell proliferation promoting effect from the seeds of Trigonella foenum-graecum L.

Journal: Journal of natural medicines 20100701

Title: Study on the relevance between beany flavor and main bioactive components in Radix Astragali.

Journal: Journal of agricultural and food chemistry 20100512

Title: Ligustilide suppresses the biological properties of Danggui Buxue Tang: a Chinese herbal decoction composed of radix astragali and radix angelica sinensis.

Journal: Planta medica 20100301

Title: Comparison of the immunoregulatory function of different constituents in radix astragali and radix hedysari.

Journal: Journal of biomedicine & biotechnology 20100101

Title: Calycosin promotes angiogenesis involving estrogen receptor and mitogen-activated protein kinase (MAPK) signaling pathway in zebrafish and HUVEC.

Journal: PloS one 20100101

Title: The effective fraction isolated from Radix Astragali alleviates glucose intolerance, insulin resistance and hypertriglyceridemia in db/db diabetic mice through its anti-inflammatory activity.

Journal: Nutrition & metabolism 20100101

Title: Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells.

Journal: Journal of natural products 20091201

Title: [Isoflavones from vines of Pueraria lobata].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20091201

Title: Stimulating effects of Bacillus subtilis natto-fermented Radix astragali on hyaluronic acid production in human skin cells.

Journal: Journal of ethnopharmacology 20090925

Title: Microsomal metabolism of calycosin, formononetin and drug-drug interactions by dynamic microdialysis sampling and HPLC-DAD-MS analysis.

Journal: Journal of pharmaceutical and biomedical analysis 20090815

Title: [Constituents of Millettia nitida var. hirsutissima].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090801

Title: An updated review of tyrosinase inhibitors.

Journal: International journal of molecular sciences 20090601

Title: Inhibitory effects of calycosin isolated from the root of Astragalus membranaceus on melanin biosynthesis.

Journal: Biological & pharmaceutical bulletin 20090201

Title: Protection of PC12 cells against superoxide-induced damage by isoflavonoids from Astragalus mongholicus.

Journal: Biomedical and environmental sciences : BES 20090201

Title: Determination of two metabolites of calycosin-7-O-beta-D-glucopyranoside in rat urine by HPLC.

Journal: Biomedical chromatography : BMC 20090101

Title: Protective effect of isoflavones from Trifolium pratense on dopaminergic neurons.

Journal: Neuroscience research 20081001

Title: Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.

Journal: Journal of agricultural and food chemistry 20080827

Title: Chemical comparison and classification of Radix Astragali by determination of isoflavonoids and astragalosides.

Journal: Journal of pharmaceutical and biomedical analysis 20080609

Title: Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.

Journal: Bioorganic & medicinal chemistry 20080515

Title: Determination of nine active components in Radix Hedysari and Radix Astragali using capillary HPLC with diode array detection and MS detection.

Journal: Journal of separation science 20080201

Title: Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.

Journal: Bioorganic & medicinal chemistry 20080101

Title: NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.

Journal: Magnetic resonance in chemistry : MRC 20080101

Title: Phenylalanine ammonia lyase functions as a switch directly controlling the accumulation of calycosin and calycosin-7-O-beta-D-glucoside in Astragalus membranaceus var. mongholicus plants.

Journal: Journal of experimental botany 20080101

Title: Chemical markers for the quality control of herbal medicines: an overview.

Journal: Chinese medicine 20080101

Title: Combined effects of fangchinoline from Stephania tetrandra Radix and formononetin and calycosin from Astragalus membranaceus Radix on hyperglycemia and hypoinsulinemia in streptozotocin-diabetic mice.

Journal: Biological & pharmaceutical bulletin 20071101

Title: Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry.

Journal: Journal of pharmaceutical and biomedical analysis 20070903

Title: Accumulation of calycosin and its 7-O-beta-D-glucoside and related gene expression in seedlings of Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao induced by low temperature stress.

Journal: Plant cell reports 20070701

Title: Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070601

Title: Rotenoids and flavonoids with anti-invasion of HT1080, anti-proliferation of U937, and differentiation-inducing activity in HL-60 from Erycibe expansa.

Journal: Bioorganic & medicinal chemistry 20070201

Title: Verification of the formulation and efficacy of Danggui Buxue Tang (a decoction of Radix Astragali and Radix Angelicae Sinensis): an exemplifying systematic approach to revealing the complexity of Chinese herbal medicine formulae.

Journal: Chinese medicine 20070101

Title: Quality evaluation of Radix Astragali through a simultaneous determination of six major active isoflavonoids and four main saponins by high-performance liquid chromatography coupled with diode array and evaporative light scattering detectors.

Journal: Journal of chromatography. A 20061117

Title: Screening and identification of permeable components in a combined prescription of Danggui Buxue decoction using a liposome equilibrium dialysis system followed by HPLC and LC-MS.

Journal: Journal of separation science 20060901

Title: [Simultaneous determination of five isoflavonoids in commercial Radix Astragali by high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20060901

Title: Calcium channel blocking activity of calycosin, a major active component of Astragali Radix, on rat aorta.

Journal: Acta pharmacologica Sinica 20060801

Title: Solvent effect in 1H NMR spectra of 3'-hydroxy-4'-methoxy isoflavonoids from Astragalus membranaceus var. mongholicus.

Journal: Magnetic resonance in chemistry : MRC 20060701

Title: Absorption and metabolism of Astragali radix decoction: in silico, in vitro, and a case study in vivo.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060601

Title: Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines.

Journal: Journal of pharmaceutical and biomedical analysis 20060503

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Chemical and biological assessment of a chinese herbal decoction containing Radix Astragali and Radix Angelicae Sinensis: Determination of drug ratio in having optimized properties.

Journal: Journal of agricultural and food chemistry 20060405

Title: Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.

Journal: Journal of chromatography. A 20060224

Title: Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.

Journal: Journal of natural products 20060101

Title: Astrapterocarpan isolated from Astragalus membranaceus inhibits proliferation of vascular smooth muscle cells.

Journal: European journal of pharmacology 20051121

Title: Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge.

Journal: Biomedical and environmental sciences : BES 20051001

Title: [Preparative isolation and purification of calycosin and formononetin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography].

Journal: Se pu = Chinese journal of chromatography 20050501

Title: Isoflavonoids from Astragalus mongholicus protect PC12 cells from toxicity induced by L-glutamate.

Journal: Journal of ethnopharmacology 20050408

Title: Capillary liquid chromatography-microcoil 1H nuclear magnetic resonance spectroscopy and liquid chromatography-ion trap mass spectrometry for on-line structure elucidation of isoflavones in Radix astragali.

Journal: Journal of chromatography. A 20050304

Title: Simultaneous determination of six isoflavonoids in commercial Radix Astragali by HPLC-UV.

Journal: Fitoterapia 20050301

Title: Determination of seven compounds in Tang Maikang granule by high-performance liquid chromatography.

Journal: Journal of chromatographic science 20050101

Title: Chemical and biological assessment of a traditional chinese herbal decoction prepared from Radix Astragali and Radix Angelicae Sinensis: orthogonal array design to optimize the extraction of chemical constituents.

Journal: Planta medica 20041201

Title: [Studies on chromatography fingerprint of huangqi by HPLC].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20041101

Title: Determination and identification of isoflavonoids in Radix astragali by matrix solid-phase dispersion extraction and high-performance liquid chromatography with photodiode array and mass spectrometric detection.

Journal: Journal of chromatography. A 20040402

Title: Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus.

Journal: Phytochemistry 20040401

Title: Effects of calycosin on the impairment of barrier function induced by hypoxia in human umbilical vein endothelial cells.

Journal: European journal of pharmacology 20031114

Title: Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection.

Journal: Journal of chromatography. A 20031024

Title: [Studies on chemical constituents of Hedysarum polybotrys].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20030801

Title: [Analysis of natural medicines by micellar electrokinetic chromatography (MEKC) (II)--determination of atractylenolide III in Atractylodis Rhizoma].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20030601

Title: [Studies on the chemical constituents of Spatholobus suberectus Dunn].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20021001

Title: Metabolism of biochanin A and formononetin by human liver microsomes in vitro.

Journal: Journal of agricultural and food chemistry 20020814

Title: Preparative isolation and purification of calycosin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20020712

Title: Flavonoids from Glycyrrhiza pallidiflora hairy root cultures.

Journal: Phytochemistry 20020601

Title: Andinermals A-C, antiplasmodial constituents from Andira inermis.

Journal: Phytochemistry 20011101

Title: Review article number 135 biosynthesis in the rotenoid group of natural products: applications of isotope methodology.

Journal: Phytochemistry 19981120

Title: Zhou Y, et al. Calycosin induces apoptosis in human ovarian cancer SKOV3 cells by activating caspases and Bcl-2 family proteins. Tumour Biol. 2015 Feb 12.

Title: Chen J, et al. Calycosin and genistein induce apoptosis by inactivation of HOTAIR/p-Akt signaling pathway in human breast cancer MCF-7 cells. Cell Physiol Biochem. 2015;35(2):722-8.

Title: Chen J, et al. Calycosin suppresses breast cancer cell growth via ERβ-dependent regulation of IGF-1R, p38 MAPK and PI3K/Akt pathways. PLoS One. 2014 Mar 11;9(3):e91245.

Title: Chen J, et al. Calycosin promotes proliferation of estrogen receptor-positive cells via estrogen receptors and ERK1/2 activation in vitro and in vivo. Cancer Lett. 2011 Sep 28;308(2):144-51.

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