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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

Molecular Formula C16H12O6
Molecular Weight 300.2629
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

PubMed

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).
Substance Class Chemical
Record UNII
Q813145M20
Record Status Validated (UNII)
Record Version