8-O-Acetylharpagide

Names

[ Name ]:
8-O-Acetylharpagide

[Synonym ]:
β-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-7-(acetyloxy)-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methylcyclopenta[c]pyran-1-yl
6-Thio-8-propylthiotheophylline
(1S,4aS,5R,7S,7aS)-1-(β-D-Glucopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl acetate
8-O-acetyl-harpagide
Harpagide 7-acetyl
Uric acid,1,3-dimethyl-8-propylthio-6-thio
8-n-Propylthio-6-thiotheophyllin

Biological Activity

[Description]:

8-O-Acetylharpagide is an iridoid isolated from Ajuga reptans with antitumoral, antiviral, antibacterial, and anti-inflammatory activities. 8-O-Acetylharpagide also has a biological activity on isolated smooth muscle preparations from guinea pig[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Wen B, et al. Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens Thunb extract in rats. J Ethnopharmacol. 2013 May 20;147(2):503-8.

[2]. Breschi MC, et al. Vasoconstrictor activity of 8-O-acetylharpagide from Ajuga reptans. J Nat Prod. 1992 Aug;55(8):1145-8.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
607.2±55.0 °C at 760 mmHg

[ Melting Point ]:
227-229℃

[ Molecular Formula ]:
C₁₇H₂₆O₁₁

[ Molecular Weight ]:
406.382

[ Flash Point ]:
215.9±25.0 °C

[ Exact Mass ]:
406.147522

[ PSA ]:
175.37000

[ LogP ]:
-3.48

[ Vapour Pressure ]:
0.0±3.9 mmHg at 25°C

[ Index of Refraction ]:
1.624

[ Storage condition ]:
?20°C

Safety Information

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

Articles

[Pharmacokinetics of 8-O-acetylharpagide and harpagide after oral administration of Ajuga decumbens extract in beagle dog].

Zhongguo Zhong Yao Za Zhi 38(12) , 2015-8, (2013)

8-O-acetylharpagide and harpagide are two kinds of effective component of Ajuga decumbens extract. A sensitive LC-MS/MS method has been established for pharmacokinetics of 8-O-acetylharpagide and harp...

[Determination of acetylharpagide in Ajuga decumbens by HPLC].

Zhongguo Zhong Yao Za Zhi 31(4) , 289-90, (2006)

To establish a method of the quantitative determination of acetylharpagide in Ajuga decumbens.The chromatographic conditions were as follows: a Phenomenex Luna C18 column was used, the mobile phase wa...

[Studies on chemical constituents of Galeopsis bifida].

Zhongguo Zhong Yao Za Zhi 27(3) , 206-8, (2002)

To investigate the chemical constituents of Galeopsis bifida.Various chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by chem...