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Kahweol

Names

[ CAS No. ]:
6894-43-5

[ Name ]:
Kahweol

[Synonym ]:
(1S,4S,12S,13R,16R,17R)-17-(Hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0.0.0]nonadeca-5(9),6,10-trien-17-ol

Biological Activity

[Description]:

Kahweol is one of the consituents of the coffee from Coffea Arabica with anti-inflammatory anti-angiogenic, and anti-cancerous activities. Kahweol inhibits adipogenesis and increase glucose uptake by AMP-activated protein kinase (AMPK) activation. Kahweol induces apoptosis.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK
Signaling Pathways >> Apoptosis >> Apoptosis
Signaling Pathways >> PI3K/Akt/mTOR >> AMPK

[Target]

AMPK; adipogenesis; apoptosis[1]


[In Vitro]

Kahweol (20-40 μM; 24 hours) decreases TGF-β-induced CTGF protein expression in AML12 and LX2 cells[1]. Kahweol (20-40 μM; 1 hour) decreases TGF-β-induced phospho-Smad2/3 expression in AML12 cells, but does not affect expression in LX2 cells[1]. Kahweol (20-40 μM) significantly decreased TGF-β-stimulated phospho-ERK and JNK expression in primary hepatocytes only[1]. kahweol (0-25 μg/ml; 6-24 hours) increased the phosphorylation of AMPK and its downstream target Acetyl-CoA carboxylase (ACC) in a time-dependent manner in 3T3-L1 cells[2]. kahweol (0-25 μg/ml) significantly affects protein expression of PPARγ, C/EBPα, FABP4, and FASN, that regulate adipocyte differentiation and lipid metabolism[2]. Western Blot Analysis[2] Cell Line: 3T3-L1 cells Concentration: 0, 5, 10, 25 μg/ml Incubation Time: Result: Reduced PPARγ, C/EBPα, FABP4, and FASN expression in a dose-dependent manner.

[References]

[1]. Seo HY, et al. Kahweol decreases hepatic fibrosis by inhibiting the expression of connective tissue growth factor via the transforming growth factor-beta signaling pathway. Oncotarget. 2017 Aug 1;8(50):87086-87094.

[2]. Baek JH, et al. Kahweol inhibits lipid accumulation and induces Glucose-uptake through activation of AMP-activated protein kinase (AMPK). BMB Rep. 2017 Nov;50(11):566-571.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
476.6±45.0 °C at 760 mmHg

[ Melting Point ]:
88-90 °C

[ Molecular Formula ]:
C20H26O3

[ Molecular Weight ]:
314.419

[ Flash Point ]:
242.0±28.7 °C

[ Exact Mass ]:
314.188202

[ PSA ]:
53.60000

[ LogP ]:
3.38

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.623

Synthetic Route


Related Compounds

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