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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O6
Molecular Weight 300.2629
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHRYSERIOL

SMILES

COC1=CC(=CC=C1O)C2=CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=SCZVLDHREVKTSH-UHFFFAOYSA-N
InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

HIDE SMILES / InChI
Chryseriol (Chrysoeriol) is a methoxylated flavone of great scientific interest because of its promising antioxidant, antiinflammatory, antitumor, antimicrobial, antiviral, and free radical scavenging activities. Chryseriol is a promising inhibitor of protein kinase CK2α and CK2α', the catalytic subunits of CK2, with IC50 values of 250 and 34 nM for CK2α and CK2α', respectively. Chrysoeriol produced a noncompetitive and mixed inhibition of pancreatic lipase with IC50=158uM. Chryseriol is a dual c‑Met and VEGFR2 kinase inhibitor. The results of docking experiments revealed that chrysoeriol was able to efficiently bind in the active site cavity of c‑Met and VEGFR2. The results of enzymatic assays showed relatively high binding affinities of chrysoeriol to c‑Met (Kd=12 uM) and VEGFR2 (Kd=11 uM). Chrysoeriol selectively inhibited human recombinant CYP1B1-mediated 7-ethoxyresorufin-O-deethylation (EROD) activity 5-fold more than that of CYP1A1-mediated activity in a competitive manner. Additionally, chrysoeriol inhibited E(2) hydroxylation catalyzed by CYP1B1, but not by CYP1A1. So chrysoeriol is a chemopreventive natural ingredient that can selectively inhibit CYP1B1 activity and prevent the formation of carcinogenic 4-OHE(2) from E(2.). Chrysoeriol was a selective PI3K-AKT-mTOR pathway inhibitor. It restrained the proliferation of human multiple myeloma cells, but didn't affect proliferation of PBMNCs from normal donors. It might exhibit the cell cycle regulatory effect via the inhibition of PI3K-AKT-mTOR signal pathway. The US Food and Drug Administration (FDA) recently granted orphan drug approval for Chrysoeriol, a cannabis-based drug used to treat acute myeloid leukaemia, which was developed by Jamaican scientist Dr Henry Lowe.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Studies on chemical constituents of Meconopsis quintuplinervia Regel].
2002 Apr
Fractionation of orange peel phenols in ultrafiltered molasses and mass balance studies of their antioxidant levels.
2004 Dec 15
Antioxidants and inhibitor of matrix metalloproteinase-1 expression from leaves of Zostera marina L.
2004 Feb
Neuroprotective and antioxidant activity of compounds from the aerial parts of Dioscorea opposita.
2005 Aug
Effects of compounds in leaves of Salix matsudana on arachidonic acid metabolism.
2005 Dec
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005 Feb 15
A new flavone glycoside and other constituents from Carduus crispus.
2005 Mar
Two acylated flavonoid glycosides from Stachys bombycina, and their free radical scavenging activity.
2005 Nov
Selective bronchodilatory effect of Rooibos tea (Aspalathus linearis) and its flavonoid, chrysoeriol.
2006 Dec
Newbouldiaquinone A: A naphthoquinone-anthraquinone ether coupled pigment, as a potential antimicrobial and antimalarial agent from Newbouldia laevis.
2006 Mar
[Studies on the flavonoids from whole herbs of Seriphidium terrae-albae].
2006 May
Complete assignments of NMR data of 13 hydroxymethoxyflavones.
2007 Dec
Detection and quantification of glycosylated flavonoid malonates in celery, Chinese celery, and celery seed by LC-DAD-ESI/MS.
2007 Feb 21
[Studies on chemical constituents from leaves of Cassia alata].
2009 Apr
[Studies on chemical components of Lobelia chinensis].
2009 Feb
[New homoisoflavanones from Polygonatum odoratum (Mill.) Druce].
2009 Jul
Identification and quantification of flavonoids and phenolic acids in burr parsley (Caucalis platycarpos L.), using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry.
2009 Jul 9
Quantitative determination of flavonoids by column high-performance liquid chromatography with mass spectrometry and ultraviolet absorption detection in Artemisia afra and comparative studies with various species of Artemisia plants.
2009 Mar-Apr
Protective effect of chrysoeriol against doxorubicin-induced cardiotoxicity in vitro.
2009 Nov 5
[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].
2009 Sep
Leucas aspera: A review.
2010 Jan
A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells.
2010 Jan
Old and new inhibitors of quinone reductase 2.
2010 Jul 30
Cassia occidentalis L.: a review on its ethnobotany, phytochemical and pharmacological profile.
2010 Jun
Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation.
2010 Oct
Vitexin, orientin and other flavonoids from Spirodela polyrhiza inhibit adipogenesis in 3T3-L1 cells.
2010 Oct
NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species.
2010 Sep
Patents

Sample Use Guides

In Vitro Use Guide
Chrysoeriol exhibited antimicrobial activity against nine pathogens in a disc diffusion assay at the concentration of 40 ug per disc. It has minimum inhibitory concentration (MIC) values of 1.25 ug/mL against a methicillin-resistant Staphylococcus aureus 3640 (MRSA) for which the parent luteolin has an MIC value of sixteen-fold higher concentration (i.e., 20 ug/mL).
Name Type Language
CHRYSERIOL
Common Name English
CHRYSOERIOL
Common Name English
3'-O-METHYLLUTEOLIN
Common Name English
CRESOROL
Common Name English
3'-METHOXY-4',5,7-TRIHYDROXYFLAVONE
Systematic Name English
5,7,4'-TRIHYDROXY-3'-METHOXYFLAVONE
Systematic Name English
3'-METHOXYAPIGENIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-
Systematic Name English
LUTEOLIN 3'-METHYL ETHER
Common Name English
CHRYSORIOL
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 582017
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
Code System Code Type Description
PUBCHEM
5280666
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
PRIMARY
WIKIPEDIA
Chrysoeriol
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
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CHEBI
57799
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-742-6
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
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EPA CompTox
DTXSID60197687
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
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CAS
491-71-4
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
PRIMARY
CHEBI
16514
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
PRIMARY
FDA UNII
Q813145M20
Created by admin on Sat Dec 16 08:42:16 GMT 2023 , Edited by admin on Sat Dec 16 08:42:16 GMT 2023
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