CALYCOSIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O5
Molecular Weight	284.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=C(C=C1)C2=COC3=C(C=CC(O)=C3)C2=O

InChI

InChIKey=ZZAJQOPSWWVMBI-UHFFFAOYSA-N

InChI=1S/C16H12O5/c1-20-14-5-2-9(6-13(14)18)12-8-21-15-7-10(17)3-4-11(15)16(12)19/h2-8,17-18H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H12O5
Molecular Weight	284.2635
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Review article number 135 biosynthesis in the rotenoid group of natural products: applications of isotope methodology.	1998 Nov 20	11711058
Andinermals A-C, antiplasmodial constituents from Andira inermis.	2001 Nov	11672743
[Analysis of natural medicines by micellar electrokinetic chromatography (MEKC) (II)--determination of atractylenolide III in Atractylodis Rhizoma].	2003 Jun	12822489
Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection.	2003 Oct 24	14601839
Isoflavonoids from Astragalus mongholicus protect PC12 cells from toxicity induced by L-glutamate.	2005 Apr 8	15763368
[Preparative isolation and purification of calycosin and formononetin from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed counter-current chromatography].	2005 May	16124581
Astrapterocarpan isolated from Astragalus membranaceus inhibits proliferation of vascular smooth muscle cells.	2005 Nov 21	16297381
Determination of seven compounds in Tang Maikang granule by high-performance liquid chromatography.	2005 Nov-Dec	16438792
Studies of chemical constituents and their antioxidant activities from Astragalus mongholicus Bunge.	2005 Oct	16370311
Chemical and biological assessment of a chinese herbal decoction containing Radix Astragali and Radix Angelicae Sinensis: Determination of drug ratio in having optimized properties.	2006 Apr 5	16569074
Calcium channel blocking activity of calycosin, a major active component of Astragali Radix, on rat aorta.	2006 Aug	16867251
Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.	2006 Feb 24	16413562
Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities.	2006 Jan	16441066
Solvent effect in 1H NMR spectra of 3'-hydroxy-4'-methoxy isoflavonoids from Astragalus membranaceus var. mongholicus.	2006 Jul	16602082
Absorption and metabolism of Astragali radix decoction: in silico, in vitro, and a case study in vivo.	2006 Jun	16507649
Live cell extraction and HPLC-MS analysis for predicting bioactive components of traditional Chinese medicines.	2006 May 3	16488100
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.	2006 Nov 17	16982063
[Simultaneous determination of five isoflavonoids in commercial Radix Astragali by high performance liquid chromatography].	2006 Sep	17165544
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.	2006 Sep	17069252
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.	2007 Jul	17253088
Analysis of interaction property of bioactive components in Danggui Buxue Decoction with protein by microdialysis coupled with HPLC-DAD-MS.	2007 Jun 1	17383242
Combined effects of fangchinoline from Stephania tetrandra Radix and formononetin and calycosin from Astragalus membranaceus Radix on hyperglycemia and hypoinsulinemia in streptozotocin-diabetic mice.	2007 Nov	17978479
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.	2007 Nov 29	18045504
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.	2007 Sep 3	17658714
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.	2008	18583351
Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim.	2008 Aug 27	18671403
Determination of nine active components in Radix Hedysari and Radix Astragali using capillary HPLC with diode array detection and MS detection.	2008 Feb	18196526
NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.	2008 Jan	18098226
Chemical markers for the quality control of herbal medicines: an overview.	2008 Jun 28	18588699
Chemical comparison and classification of Radix Astragali by determination of isoflavonoids and astragalosides.	2008 Jun 9	18272311
Protective effect of isoflavones from Trifolium pratense on dopaminergic neurons.	2008 Oct	18675857
[Constituents of Millettia nitida var. hirsutissima].	2009 Aug	19894535
Inhibitory effects of calycosin isolated from the root of Astragalus membranaceus on melanin biosynthesis.	2009 Feb	19182387
Determination of two metabolites of calycosin-7-O-beta-D-glucopyranoside in rat urine by HPLC.	2009 Jan	18816507
Stimulating effects of Bacillus subtilis natto-fermented Radix astragali on hyaluronic acid production in human skin cells.	2009 Sep 25	19619633
Comparison of the immunoregulatory function of different constituents in radix astragali and radix hedysari.	2010	20224658
Structural relationship and binding mechanisms of five flavonoids with bovine serum albumin.	2010 Dec 9	21150826
Calycosin promotes angiogenesis involving estrogen receptor and mitogen-activated protein kinase (MAPK) signaling pathway in zebrafish and HUVEC.	2010 Jul 29	20686605
Ligustilide suppresses the biological properties of Danggui Buxue Tang: a Chinese herbal decoction composed of radix astragali and radix angelica sinensis.	2010 Mar	19847742
[Simultaneous assay of four isoflavonoids in Astragali Radix by QAMS].	2010 Oct	21246825
[Simultaneous determination of nine isoflavonoids in Huangqi Gegen decoction by high performance liquid chromatography].	2010 Oct	21246819
Flavonoids from Radix Astragali induce the expression of erythropoietin in cultured cells: a signaling mediated via the accumulation of hypoxia-inducible factor-1α.	2011 Mar 9	21309574
Profiling of hepatocellular carcinoma cell cycle regulating genes targeted by calycosin.	2013	24455688
Regioselective glucuronidation of the isoflavone calycosin by human liver microsomes and recombinant human UDP-glucuronosyltransferases.	2014 Sep 5	25044472

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:59:25 GMT 2023` Edited by `admin` on `Fri Dec 15 18:59:25 GMT 2023`
Record UNII	09N3E8P7TA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CALYCOSIN

Common Name

English

CALYCOSIN (CONSTITUENT OF ASTRAGALUS) [DSC]

Common Name

English

7-HYDROXY-3-(3-HYDROXY-4-METHOXYPHENYL)CHROMEN-4-ONE

Systematic Name

English

3',7-DIHYDROXY-4'-METHOXYISOFLAVONE

Common Name

English

3'-HYDROXYFORMONONETIN

Common Name

English

CALYCOSIN [USP-RS]

Common Name

English

Code System Code Type Description

RS_ITEM_NUM

1087472