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Amarogentin

Names

[ CAS No. ]:
21018-84-8

[ Name ]:
Amarogentin

[Synonym ]:
(4aS,5R,6S)-1-Oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-D-glucopyranoside
(4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-D-glucopyranoside
amorogentin
sweroside-2'-O-3",5",3'''-trihydroxy-biphenyl-2''-carboxylic acid
[4aS-(4aa,5b,6a)]-3,3',5-Trihydroxy[1,1'-biphenyl]-2-carboxylic Acid 2-Ester with 5-Ethenyl-6-(b-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
Sweroside-2'-(3'',5'',3'''-trihydroxydiphenyl)-2''-carboxylic Acid Ester
amarosgentin
Amarogentin Hydrate
(4aS,5R,6S)-1-Oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl 2-O-[(3,3',5-trihydroxy-2-biphenylyl)carbonyl]-β-D-glucopyranoside
1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-4,4a,5,6-tetrahydro-6-((2-O-((3,3',5-trihydroxy(1,1'-biphenyl)-2-yl)carbonyl)-β-D-glucopyranosyl)oxy)-, (4aS,5R,6S)-
1H,3H-Pyrano[3,4-c]pyran-1-one, 5-ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3',5-trihydroxy[1,1'-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-, (4aS,5R,6S)-
Amarogentin

Biological Activity

[Description]:

Amarogentin is a secoiridoid glycoside that is mainly extracted from Swertia and Gentiana roots. Amarogentin exhibits many biological effects, including anti-oxidative, anti-tumour, and anti-diabetic activities. Amarogentin exerts hepatoprotective and immunomodulatory effects. Amarogentin promotes apoptosis, arrests G2/M cell cycle and downregulates of PI3K/Akt/mTOR signalling pathways. Amarogentin exerts beneficial vasculo-metabolic effect by activating AMPK[1][2][3].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK
Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> PI3K/Akt/mTOR >> AMPK
Research Areas >> Metabolic Disease

[References]

[1]. Zhang Y, et al. Protective Effects of Amarogentin against Carbon Tetrachloride-Induced Liver Fibrosis in Mice. Molecules. 2017 May 6;22(5). pii: E754.

[2]. Wölfle U, et al. Amarogentin Displays Immunomodulatory Effects in Human Mast Cells and Keratinocytes. Mediators Inflamm. 2015;2015:630128.

[3]. Zhao JG, et al. Amarogentin secoiridoid inhibits in vivo cancer cell growth in xenograft mice model and induces apoptosis in human gastric cancer cells (SNU-16) through G2/M cell cycle arrest and PI3K/Akt signalling pathway. J BUON. 2016 May-Jun;21(3):609-17.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
928.5±65.0 °C at 760 mmHg

[ Melting Point ]:
229-230ºC

[ Molecular Formula ]:
C29H30O13

[ Molecular Weight ]:
586.541

[ Flash Point ]:
306.9±27.8 °C

[ Exact Mass ]:
586.168640

[ PSA ]:
201.67000

[ LogP ]:
2.79

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.693

[ Storage condition ]:
-20C

Related Compounds