2-(2,4-Dihydroxyphenyl)-3-(3-methyl-2-butenyl)-5-hydroxy-8,8-dimethyl-4H,8H-benzo[1,2-b:5,4-b']dipyran-4-one

Names

[ CAS No. ]:
19275-49-1

[ Name ]:
2-(2,4-Dihydroxyphenyl)-3-(3-methyl-2-butenyl)-5-hydroxy-8,8-dimethyl-4H,8H-benzo[1,2-b:5,4-b']dipyran-4-one

[Synonym ]:
Mulberrochromen
mulberrochromene
2-(2,4-dihydroxy-phenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-but-2-enyl)-8H-pyrano[3,2-g]chromen-4-one
2-(2,4-Dihydroxy-phenyl)-5-hydroxy-8,8-dimethyl-3-(3-methyl-but-2-enyl)-8H-pyrano[3,2-g]chromen-4-one

Biological Activity

[Description]:

Cudraflavone B is a prenylated flavonoid with anti-inflammatory and anti-tumor properties. Cudraflavone B is also a dual inhibitor of COX-1 and COX-2. Cudraflavone B blocks the translocation of nuclear factor κB (NF-κB) from the cytoplasm to the nucleus in macrophages. Thus, Cudraflavone B inhibits tumor necrosis factor α (TNFα) gene expression and secretion. Cudraflavone B also triggers the mitochondrial apoptotic pathway, activates NF-κB, the MAPK p38, and ERK, and induced the expression of SIRT1. Thus Cudraflavone B inhibits the growth of human oral squamous cell carcinoma cells[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Sirtuin

Signaling Pathways >> Cell Cycle/DNA Damage >> Sirtuin

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[Target]

NF-κB

COX-2

COX-1

TNFRSF1A

p38 MAP kinase

ERK

SIRT1

[References]

[1]. Hošek J, et al. Natural compound cudraflavone B shows promising anti-inflammatory properties in vitro. J Nat Prod. 2011 Apr 25;74(4):614-9.

[2]. Lee HJ, et al. Growth inhibition and apoptosis-inducing effects of cudraflavone B in human oral cancer cells via MAPK, NF-κB, and SIRT1 signaling pathway. Planta Med. 2013 Sep;79(14):1298-306.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₅H₂₄O₆

[ Molecular Weight ]:
420.45

[ Exact Mass ]:
420.15700

[ PSA ]:
100.13000

[ LogP ]:
5.26970