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
SMILES
COC1=C(O)C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(O)C=C3O
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
| Molecular Formula | C16H12O6 |
| Molecular Weight | 300.2629 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
| Title | Date | PubMed |
|---|---|---|
| [Chemical constituents from aerial parts of Fallopia convolvulus]. | 2010-12 |
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| Discovery of chrysoeriol, a PI3K-AKT-mTOR pathway inhibitor with potent antitumor activity against human multiple myeloma cells in vitro. | 2010-12 |
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| Comparative study of the flavonoids of some Verbena species cultivated in Egypt by using high-performance liquid chromatography coupled with ultraviolet spectroscopy and atmospheric pressure chemical ionization mass spectrometry. | 2010-10-08 |
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| Chrysoeriol isolated from Eurya cilliata leaves protects MC3T3-E1 cells against hydrogen peroxide-induced inhibition of osteoblastic differentiation. | 2010-10 |
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| Vitexin, orientin and other flavonoids from Spirodela polyrhiza inhibit adipogenesis in 3T3-L1 cells. | 2010-10 |
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| Selective inhibition of methoxyflavonoids on human CYP1B1 activity. | 2010-09-01 |
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| NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species. | 2010-09 |
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| Behavioural characterization of four endemic Stachys taxa. | 2010-09 |
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| Old and new inhibitors of quinone reductase 2. | 2010-07-30 |
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| [Studies on the chemical constituents from pine needles of Cedrus deodara (II)]. | 2010-07 |
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| Identification of functional TFAP2A and SP1 binding sites in new TFAP2A-modulated genes. | 2010-06-03 |
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| Antihyperglycaemic and protective effects of flavonoids on streptozotocin-induced diabetic rats. | 2010-06 |
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| Cassia occidentalis L.: a review on its ethnobotany, phytochemical and pharmacological profile. | 2010-06 |
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| Inhibitory effects of chrysoeriol on DNA adduct formation with benzo[a]pyrene in MCF-7 breast cancer cells. | 2010-04-21 |
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| [Chemical constituents from Lagotis brevituba]. | 2010-04 |
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| Identification of bisprenylated benzoic acid derivatives from yerba santa (Eriodictyon ssp.) using sensory-guided fractionation. | 2010-02-10 |
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| [Study on the flavonoids from Mosla chinensis 'jiangxiangru']. | 2010-02 |
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| Effects of Various Flavonoids on the α-Synuclein Fibrillation Process. | 2010-01-28 |
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| Leucas aspera: A review. | 2010-01 |
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| A methoxyflavonoid, chrysoeriol, selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. | 2010-01 |
|
| Metalloproteinase inhibitors: status and scope from marine organisms. | 2010 |
|
| Fragmentation pathways of acylated flavonoid diglucuronides from leaves of Medicago truncatula. | 2009-12-02 |
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| Cytotoxic phenolic compounds from Chionanthus retusus. | 2009-12 |
|
| Protective effect of chrysoeriol against doxorubicin-induced cardiotoxicity in vitro. | 2009-11-05 |
|
| [Bioactive constituents from whole herbs of Vernonia cinerea (II)]. | 2009-11 |
|
| Chrysoeriol isolated from the leaves of Eurya ciliata stimulates proliferation and differentiation of osteoblastic MC3T3-E1 cells. | 2009-09 |
|
| [Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense]. | 2009-09 |
|
| 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. | 2009-07-09 |
|
| [Studies on the chemical constituents of Blumea laciniata]. | 2009-07 |
|
| [New homoisoflavanones from Polygonatum odoratum (Mill.) Druce]. | 2009-07 |
|
| 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. | 2009-06-03 |
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| Flavonoid glucuronides and a chromone from the aquatic macrophyte Stratiotes aloides. | 2009-05-22 |
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| An inhibitory effect of chrysoeriol on platelet-derived growth factor (PDGF)-induced proliferation and PDGF receptor signaling in human aortic smooth muscle cells. | 2009-05 |
|
| [Studies on chemical constituents from leaves of Cassia alata]. | 2009-04 |
|
| Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1. | 2009-03-25 |
|
| [Studies on chemical components of Lobelia chinensis]. | 2009-02 |
|
| Antioxidative iridoid glycosides and phenolic compounds from Veronica peregrina. | 2009-02 |
|
| Chemical constituents isolated from Polygala japonica leaves and their inhibitory effect on nitric oxide production in vitro. | 2009-02 |
|
| Phenolic compounds and chromatographic profiles of pear skins (Pyrus spp.). | 2008-10-08 |
|
| Analysis of heartsease (Viola tricolor L.) flavonoid glycosides by micro-liquid chromatography coupled to multistage mass spectrometry. | 2008-10-03 |
|
| Non-cannabinoid constituents from a high potency Cannabis sativa variety. | 2008-10 |
|
| Glycosides from whole plants of Glechoma hederacea L. | 2008-10 |
|
| Free-radical-scavenging principles from Phlomis caucasica. | 2008-10 |
|
| [Studies on chemical constituents from leaves of Vaccinium bracteatum]. | 2008-09 |
|
| Anti-inflammatory and antinociceptive potential of major phenolics from Verbascum salviifolium Boiss. | 2008-06-07 |
|
| Screening for free radical scavenging and cell aggregation inhibitory activities by secondary metabolites from Turkish Verbascum species. | 2007-12-12 |
|
| Complete assignments of NMR data of 13 hydroxymethoxyflavones. | 2007-12 |
|
| Assay of flavonoid aglycones from the species of genus Sideritis (Lamiaceae) from Macedonia with HPLC-UV DAD. | 2007-09 |
|
| The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions. | 2007-07-28 |
|
| Antimicrobial activity of the methanolic extract and of the chemical constituents isolated from Newbouldia laevis. | 2007-07 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.mdpi.com/2073-4344/9/2/112
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
Created
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Edited
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| Record UNII |
Q813145M20
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
582017
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Chrysoeriol
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207-742-6
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DTXSID60197687
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Chrysoeriol only slightly inhibited p38 phosphorylation and failed to
inhibit ERK1/2 phosphorylation.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ORAC value expressed as umol TE/g for this compound was 4400 +/- 189.
ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
1,1-Diphenyl-2-picrylhydrazyl radical scavenging assay(DPPH) IC50 expressed as ug/mL >40. In vitro hydroxyl radical scavenging assay(Hydroxy Radical) IC50 expressed as ug/mL = 1.4+/-0.16.
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