(20S)-Protopanaxatriol

Names

[ Name ]:
(20S)-Protopanaxatriol

[Synonym ]:
PROTOPANAXTRIOL
20(S)-APPT,g-PPT
Gonane-3,6,12-triol, 17-[(1S)-1-hydroxy-1,5-dimethyl-4-hexen-1-yl]-4,4,10,14-tetramethyl-, (3β,6α,12β,14β,17β)-
(3β,6α,12β,14β)-4,4,14-Trimethyl-18-norcholest-24-ene-3,6,12,20-tetrol
20S-Protopanaxatriol
Protopanaxatriol, 20S-
(20S)-Protopanaxatriol

Biological Activity

[Description]:

(20S)-Protopanaxatriol is a metabolite of ginsenoside, works through the glucocorticoid receptor (GR) and oestrogen receptor (ER), and is also a LXRα inhibitor.

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Signaling Pathways >> GPCR/G Protein >> Glucocorticoid Receptor

Signaling Pathways >> Metabolic Enzyme/Protease >> LXR

Research Areas >> Cardiovascular Disease

Natural Products >> Steroids

[Target]

Glucocorticoid receptor, Oestrogen receptor[1], LXRα[2]

[In Vitro]

(20S)-Protopanaxatriol works through the glucocorticoid receptor (GR) and oestrogen receptor (ER) in human umbilical vein endothelial cells (HUVECs). (20S)-Protopanaxatriol (g-PPT) increases [Ca2+]i with an EC50 of 482 nM in HUVECs. (20S)-Protopanaxatriol (1 µM) elevates NO production via ERβ[1]. (20S)-Protopanaxatriol (PPT) inhibits the autonomous transactivation of Gal4-LXRα LBD, the T0901317-dependent transcription of SREBP-1c and its promoter. (20S)-Protopanaxatriol (10 μg/mL) blocks the recruitment of RNA polymerase II to the LXRE region of SREBP-1c. (20S)-Protopanaxatriol also inhibits T0901317-dependent transcription of LXRα target genes related to lipogenesis, and reduces T0901317-induced cellular triglyceride (TG) accumulation in primary hepatocytes, but does not alter transcription of ABCA1, also an LXRα target gene[2].

[References]

[1]. Leung KW, et al. Protopanaxadiol and protopanaxatriol bind to glucocorticoid and oestrogen receptors in endothelial cells. Br J Pharmacol. 2009 Feb;156(4):626-37.

[2]. Oh GS, et al. 20(S)-protopanaxatriol inhibits liver X receptor α-mediated expression of lipogenic genes in hepatocytes. J Pharmacol Sci. 2015 Jun;128(2):71-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
588.8±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₀H₅₂O₄

[ Molecular Weight ]:
476.73

[ Flash Point ]:
242.9±24.7 °C

[ PSA ]:
80.92000

[ LogP ]:
5.41

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.541

[ Storage condition ]:
-20°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Dual functions of ginsenosides in protecting human endothelial cells against influenza H9N2-induced inflammation and apoptosis.

J. Ethnopharmacol. 137 , 1542-1546, (2011)

Panax ginseng is a precious traditional Chinese herbal medicine which has been utilized as herbal tonic for improving immunity. The active component, ginsenosides have been shown to possess various ph...

Cytochrome P450 CYP716A53v2 catalyzes the formation of protopanaxatriol from protopanaxadiol during ginsenoside biosynthesis in Panax ginseng.

Plant Cell Physiol. 53 , 1535-1545, (2012)

Ginseng (Panax ginseng C.A. Meyer) is one of the most popular medicinal herbs, and the root of this plant contains pharmacologically active components, called ginsenosides. Ginsenosides, a class of te...

The in vitro structure-related anti-cancer activity of ginsenosides and their derivatives.

Molecules 16(12) , 10619-30, (2011)

Panax ginseng has long been used in Asia as a herbal medicine for the prevention and treatment of various diseases, including cancer. The current study evaluated the cytotoxic potency against a variet...

Related Compounds

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