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Genipin CAS:6902-77-8

2015-07-23

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Genipin CAS:6902-77-8

Product Name:Genipin

CAS No.:6902-77-8

Synonyms:(+)-Genipin

Chemical Name:Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate

Structure:6902-77-8.gif

Purity:≥98%

Molecular Formula:C11H14O5

Molecular Weight:226.2

Appearance:White to off-white solid

Solubility:Soluble in DMSO (50mg/ml), ethanol (5mg/ml), methanol or acetone. Slightly soluble in water

Biological Activity:

Genipin is a compound isolated from Gardenis jasminoides Ellis fruits which acts as a cell permeable inhibitor of UCP2 (uncoupling protein 2). Increases glucose-stimulated insulin secretion, mitochondrial membrane potential and ATP levels in pancreatic island cells. Genipin has been shown to induce apoptosis and is a protein cross-linking agent. Genipin, at 5 μM, increases glucose-stimulated insulin secretion in isolated pancreatic islets chronically exposed to high levels of glucose. Genipin also exhibits anti-inflammatory and anti-angiogenic properties by inducing apoptosis in FaO rat hepatoma cells and human hepatocarcinoma Hep3B cells.

References:

1. Tissue engineering of ureteral grafts: Preparation of biocompatible crosslinked ureteral scaffolds of porcine origin: H. Koch, et al.; Front. Bioeng. Biotechnol. 3, 89 (2015).

2. Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity: L.E. Parton, et al.; Nature449, 228 (2007).

3. Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity- and high glucose-induced beta cell dysfunction in isolated pancreatic islets: C.Y Zhang, et al.; Cell Metab. 3, 417 (2006).

4. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway: B.C. Kim, et al.; Biochem. Pharmacol. 70, 1398 (2005).