Epimedokoreanin B , CAS No.161068-53-7

CAS: 161068-53-7 Cat. No.: E646212 Peso molecular: 422.47 PubChem CID: 21147600

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Descripción general

Epimedokoreanin B is a natural flavonoid with anticancer, anti-inflammatory and antibacterial effects. Epimedokoreanin B inhibits the growth of lung cancer cells through endoplasmic reticulum stress-mediated apoptosis accompanied by autophagosome accumulation. Epimedokoreanin B is an anti-periodontitis agent that inhibits gingipains and Porphyromonas gingivalis growth and biofilm formation .

In Vitro

Epimedokoreanin B (compound6; 3.13-25 μM; 48 hours) shows significate inhibitory effect on proliferation against lung cancer cell A549, Calu1 and H1299. Epimedokoreanin B displays no toxic on human bronchial epithelial cells BEAS-2B.\nEpimedokoreanin B treatment inhibits cell proliferation and migration accompanied by cytoplasmic vacuolation in A549 and NCI-H292 cells. Atophagosome accumulation accompanied with autophagy flux blocking is observed in Epimedokoreanin B treated cells, this was consistent with the occurrence of ER stress. Epimedokoreanin B (5 μM; 24 hours) inhibits CD163 expression and IL-10 production, which are known M2 markers, suggesting that Epimedokoreanin B inhibits M2 polarization in human monocyte-derived macrophages (HMDMs). Epimedokoreanin B suppresses STAT3 activation in HMDMs . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Cell Cytotoxicity AssayCell Line: A549, Calu1 and H1299 cells Concentration: 3.13 μM, 6.25 μM, 12.5 μM and 25.0 μM Incubation Time: 48 hours Result: Showed significate inhibitory effect on proliferation against lung cancer cell A549, Calu1 and H1299. Western Blot Analysis Cell Line: Human monocyte-derived macrophages (HMDMs) Concentration: 5 μM Incubation Time: 24 hours Result: Significantly suppressed IL-10-induced JAK1/STAT3 activation.and H1299.

In Vivo

Epimedokoreanin B (20 mg/kg; p.o; thrice a week; for 17 days) inhibits tumor growth in an LM8 tumor-bearing murine model. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Female C3H mice (8-10 weeks old) injected with LM8 cellsDosage: 20 mg/kg Administration: Oral administration; thrice a week; for 17 days Result: Inhibited tumor growth.

Form:Solid

Specifications

Mecanismos bioquímicos y fisiológicos

Epimedokoreanin B is a natural flavonoid with anticancer , anti-inflammatory and antibacterial effects. Epimedokoreanin B inhibits the growth of lung cancer cells through endoplasmic reticulum stress-mediated apoptosis accompanied by autophagosome accumul

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Protected from light, Store at -20°C

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Tipo de acción

INHIBITOR

Nombres e identificadores

• Sonrisas canónicas: CC(=CCC1=C(C(=CC(=C1)C2=CC(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)O)O)O)O)C
• IUPAC Name: 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
• InChIKey: QLZMBCVLWOJASJ-UHFFFAOYSA-N
• INCHI: 1S/C25H26O6/c1-13(2)5-7-15-9-16(10-21(29)24(15)30)22-12-20(28)23-19(27)11-18(26)17(25(23)31-22)8-6-14(3)4/h5-6,9-12,26-27,29-30H,7-8H2,1-4H3
• Isómeros SMILES: CC(=CCC1=C(C(=CC(=C1)C2=CC(=O)C3=C(C=C(C(=C3O2)CC=C(C)C)O)O)O)O)C
• PubChem CID: 21147600
• Términos de entrada MeSH: 2-(3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl)-5,7-dihydroxy-8-(3-methylbut-2-enyl)chromen-4-one;epimedokoreanin B
• Peso molecular: 422.47

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Clase Flavonoids
      • Subclass Flavones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Clase: Flavonoids
• Subclass: Flavones
• Intermediate Tree Nodes: Not available
• Direct Parent: 8-prenylated flavones
• Alternative Parents: 3'-prenylated flavones 3'-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Chromones Catechols 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Vinylogous acids Heteroaromatic compounds Oxacyclic compounds Hydrocarbon derivatives Organic oxides Organooxygen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 8-prenylated flavone - 3'-prenylated flavone - 3'-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - Catechol - 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 - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as 8-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 8-position.
• External Descriptors: Flavones and Flavonols

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Peso molecular: 422.500 g/mol
• XLogP3: 6.200
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 422.173 Da
• Monoisotopic Mass: 422.173 Da
• Topological Polar Surface Area: 107.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 745.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1