Azuleno[6,5-b]furan-2,5-dione,4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-,(3aR,4S,4aR,7aR,8R,9aR)-

Names

[ Name ]:
Azuleno[6,5-b]furan-2,5-dione,4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-,(3aR,4S,4aR,7aR,8R,9aR)-

[Synonym ]:
6-O-acetylhelenalin
Helenalin acetate
Helenalin 6-acetate
Angustibalin
HELANIN ACETATE
O-Acetyl-helenalin
acetylhelenalin

Biological Activity

[Description]:

Helenalin acetate, a natural NF-κB inhibitor, is a potent C/EBPβ inhibitor. Helenalin acetate has anti-inflammatory and anticancer activities[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Epigenetics >> Histone Demethylase

Research Areas >> Inflammation/Immunology

[In Vitro]

Helenalin acetate（0.1-1 μM；持续 7 天）显着抑制 3T3-L1 细胞的分化[1]。 Helenalin acetate对急性髓性白血病细胞具有抗增殖作用，对正常造血祖细胞无作用[1]。 Helenalin acetate 通过结合到 C/EBPβ 的 N 末端部分来抑制 C/EBPβ，从而破坏 C/EBPβ 与共激活因子 p300 的合作。Helenalin acetate 仅选择性抑制全长（富含肝脏的激活蛋白* (LAP*)）同种型，但不抑制稍短的 (LAP) 同种型[1]。 Cell Differentiation Assay[1] Cell Line: 3T3-L1 cells Concentration: 0.1 μM, 0.3 μM, 1 μM Incubation Time: for 7 days Result: Inhibited the differentiation significantly.

[References]

[1]. Jakobs A, et al. Helenalin Acetate, a Natural Sesquiterpene Lactone with Anti-inflammatory and Anti-cancer Activity, Disrupts the Cooperation of CCAAT Box/Enhancer-binding Protein β (C/EBPβ) and Co-activator p300. J Biol Chem. 2016 Dec 9;291(50):26098-26108.

Chemical & Physical Properties

[ Density]:
1.22g/cm3

[ Boiling Point ]:
466.6ºC at 760 mmHg

[ Molecular Formula ]:
C₁₇H₂₀O₅

[ Molecular Weight ]:
304.33800

[ Flash Point ]:
207.1ºC

[ Exact Mass ]:
304.13100

[ PSA ]:
69.67000

[ LogP ]:
1.81710

[ Vapour Pressure ]:
6.95E-09mmHg at 25°C

[ Index of Refraction ]:
1.541