Gymnestrogenin

Names

[ CAS No. ]:
19942-02-0

[ Name ]:
Gymnestrogenin

[Synonym ]:
Gymnestrogenin
(3S,4aS,5S,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-4a,9-Bis-hydroxymethyl-2,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-picene-3,5,10-triol
gymnestrogenin
3β,16β,21β,23,28-pentahydroxyolean-12-ene

Biological Activity

[Description]:

Gymnestrogenin is a pentahydroxytriterpene from the leaves of Gymnema sylvestre R.Br[1]. Gymnestrogenin is a LXR antagonist with IC50s of 2.5 and 1.4 μM for LXRα and LXRβ transactivation, respectively. Gymnestrogenin reduces the transcriptional activity of LXR even on its own promoter, thus reducing the mRNA expression[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> LXR

Research Areas >> Metabolic Disease

[Target]

IC50: 2.5 μM (LXRα) and 1.4 μM (LXRβ)[2]

[In Vitro]

Gymnestrogenin, reducing the expression of SREBP1c and ABCA1 in vitro, is able to decrease lipid accumulation in HepG2 cells[2].

[References]

[1]. Stöcklin W, et al. [Gymnestrogenin, a new pentahydroxytriterpene from the leaves of Gymnema sylvestre R.Br]. Helv Chim Acta. 1968;51(6):1235-42.

[2]. Renga B, et al. Molecular decodification of gymnemic acids from Gymnema sylvestre. Discovery of a new class of liver X receptor antagonists. Steroids. 2015 Apr;96:121-31.

Chemical & Physical Properties

[ Melting Point ]:
288-289 °C

[ Molecular Formula ]:
C₃₀H₅₀O₅

[ Molecular Weight ]:
490.71500

[ Exact Mass ]:
490.36600

[ PSA ]:
101.15000

[ LogP ]:
4.05530