Apigenin

Common Name

Apigenin Description

Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (PMID: 16982614 ). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (PMID: 16844095 ). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (PMID: 16648565 ). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-(P-Hydroxyphenyl)-5,7-dihydroxychromoneChEBI 4',5,7-TrihydroxyflavoneChEBI 5,7,4'-TrihydroxyflavoneChEBI 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyroneChEBI 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI C.I. natural yellow 1ChEBI ChamomileChEBI SpigeninChEBI VersliinChEBI 4',5,7-Trihydroxy-flavoneHMDB 4,5, 7-TrihydroxyflavoneHMDB 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB ApigenolHMDB

Chemical Formlia

C₁₅H₁₀O₅ Average Molecliar Weight

270.2369 Monoisotopic Molecliar Weight

270.05282343 IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one Traditional Name

chamomile CAS Registry Number

520-36-5 SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

InChI Key

KZNIFHPLKGYRTM-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Kingdom

Organic compounds Super Class

Phenylpropanoids and polyketides Class

Flavonoids Sub Class

Flavones Direct Parent

Flavones Alternative Parents

7-hydroxyflavonoids

5-hydroxyflavonoids

4-hydroxyflavonoids

Chromones

Pyranones and derivatives

1-hydroxy-4-unsubstituted benzenoids

1-hydroxy-2-unsubstituted benzenoids

Benzene and substituted derivatives

Vinylogous acids

Heteroaromatic compounds

Oxacyclic compounds

Organooxygen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

4'-hydroxyflavonoid

5-hydroxyflavonoid

7-hydroxyflavonoid

Flavone

Hydroxyflavonoid

Chromone

Benzopyran

1-benzopyran

1-hydroxy-4-unsubstituted benzenoid

1-hydroxy-2-unsubstituted benzenoid

Phenol

Pyranone

Monocyclic benzene moiety

Benzenoid

Pyran

Vinylogous acid

Heteroaromatic compound

Organoheterocyclic compound

Oxacycle

Organic oxygen compound

Organooxygen compound

Organic oxide

Hydrocarbon derivative

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

trihydroxyflavone (CHEBI:18388 )

flavones (C01477 )

Flavones and Flavonols (C01477 )

Flavones and Flavonols (LMPK12110005 )

Ontology Status

Detected and Quantified Origin

Drug

Biofunction

Not Available Application

Not Available Cellliar locations

Membrane (predicted from logP)

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point347.5 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP3.02PERRISSOUD,D & TESTA,B (1986)

Predicted Properties

Property Value Source Water Solubility0.12 mg/mLALOGPS logP3.07ALOGPS logP2.71ChemAxon logS-3.4ALOGPS pKa (Strongest Acidic)6.63ChemAxon pKa (Strongest Basic)-5.2ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area86.99 Å²ChemAxon Rotatable Bond Count1ChemAxon Refractivity72.91 m³·mol^-1ChemAxon Polarizability26.78 Å³ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-00di-0000900000-b6d7fc88c039e719d164View in MoNA GC-MS

GC-MS Spectrum – GC-EI-TOFsplash10-00di-0433900000-b411d851fccc9f228d84View in MoNA GC-MS

GC-MS Spectrum – GC-EI-TOFsplash10-03xv-1913500000-be46740b1210f9e106eeView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0090000000-0f608530bf761944dbf3View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0090000000-0c659ac43b543480168bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0690000000-e19eed49b8311d9cd339View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0910000000-57a56bfe2cce55357a11View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0900000000-b8799a618cff0ac84ddbView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0490000000-f9a416c79166c84ca773View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0900000000-1499c7f2bceeb3e13f52View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0490000000-413a7da79773bc92a112View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0090000000-8f4d30104539ae85cd50View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0290000000-32e8793c17b364eee127View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-0uea-0900000000-52147353f7af35162dabView in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-014i-0090000000-7a9b77ceb393c9239412View in MoNA LC-MS/MS

LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-00vi-0290000000-c9cb9331a28763da83a8View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-TOF , negativesplash10-014i-0940000000-eb8b08c7beca627dc728View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0090000000-47dcd836edc83106c566View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0090000000-f81b58efeb7a6ad517b7View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-00di-0090000000-9ee52d5a554d161d358dView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0fk9-0970000000-f0c48df94377a366e7cfView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane (predicted from logP)

Biofluid Locations

Blood

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.127 +/- 0.081 uMAdlit (>18 years old)BothNormal

16407641

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

228 Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB002798 KNApSAcK ID

Not Available Chemspider ID

4444100 KEGG Compound ID

C01477 BioCyc ID

CPD-431 BiGG ID

Not Available Wikipedia Link

Apigenin NuGOwiki Link

HMDB02124 Metagene Link

HMDB02124 METLIN ID

3397 PubChem Compound

5280443 PDB ID

AGI ChEBI ID

18388

Product: DL-Glutamine

References Synthesis Reference Chen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp Material Safety Data Sheet (MSDS) Download (PDF) General References

Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. Epub 2006 Sep 18. [PubMed:16982614 ]
Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. Epub 2006 Jul 17. [PubMed:16844095 ]
Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51. [PubMed:16648565 ]

PMID: 17475795

By rofalproject

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