isorhapontigenin Chemical Properties

Melting point:

180.0 to 184.0 °C

Boiling point:

471.8±35.0 °C(Predicted)

Density 

1.345

storage temp. 

room temp

solubility 

DMSO: soluble15mg/mL, clear

pka

9.16±0.10(Predicted)

form 

powder

color 

white to light brown

InChI

InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+

InChIKey

ANNNBEZJTNCXHY-NSCUHMNNSA-N

SMILES

C1(O)=CC(/C=C/C2=CC=C(O)C(OC)=C2)=CC(O)=C1

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-43-51

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

2909.50.5000

isorhapontigenin Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Belamcanda chinensis.

Uses

Isorhapontigenin, an orally bioavailable dietary polyphenol isolated from the Chinese herb Gnetum cleistostachyum, displays anti-inflammatory effects. Isorhapontigenin induces autophagy and inhibits invasive bladder cancer formation[1][2].

Definition

ChEBI: Isorhapontigenin is a stilbenoid.

Biochem/physiol Actions

Isorhapontigenin or 4-methoxyresveratrol is a stilbene derivative isolated from a number of plants including Chinese medical herbs Gnetum Cleistostachyum and Iris Domestica (Belamcanda chinensis, leopard lily), and wine grapes. Similarly to resveratrol, isorhapontigenin is a potent antioxidant that attenuates ROS generation. Also, Isorhapontigenin exhibits pro-apoptopic and anti-cancer activities through downregulation of XIAP (X-linked inhibitor of apoptosis protein).

References

[1] Yeo SCM, et al. Isorhapontigenin, a bioavailable dietary polyphenol, suppresses airway epithelial cell inflammation through a corticosteroid-independent mechanism. Br J Pharmacol. 2017 Jul;174(13):2043-2059. DOI:10.1111/bph.13803
[2] Liang Y, et al. SESN2/sestrin 2 induction-mediated autophagy and inhibitory effect of isorhapontigenin (ISO) on human bladder cancers. Autophagy. 2016 Aug 2;12(8):1229-39. DOI:10.1080/15548627.2016.1179403
[3] Jiang G, et al. Isorhapontigenin (ISO) Inhibits Invasive Bladder Cancer Formation In Vivo and Human Bladder Cancer Invasion In Vitro by Targeting STAT1/FOXO1 Axis. Cancer Prev Res (Phila). 2016 Jul;9(7):567-80. DOI:10.1158/1940-6207.CAPR-15-0338

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