Genipin

Cayman Chemical Item Number 10010622

(+)-Genipin (CAS 6902-77-8)

Genipin (CAS 6902-77-8)

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Description

Uncoupling protein 2 (UCP2) is a mitochondrial carrier protein that is expressed in pancreatic islets and has been shown to negatively regulate glucose-stimulated insulin secretion.1,2 High levels of UCP2 expression can disrupt pancreatic β cell function and downregulate insulin secretion thereby contributing to the development of type 2 diabetes.3 Genipin, a compound isolated from Gardenis jasminoides Ellis fruits, was originally identified as a protein cross-linking agent. Genipin is a cell-permeable inhibitor of UCP2 activity.4 Genipin, at 5 µM, increases glucose-stimulated insulin secretion in isolated pancreatic islets chronically exposed to high levels of glucose.5 Genipin also exhibits anti-inflammatory and anti-angiogenic properties by inducing apoptosis in FaO rat hepatoma cells and human hepatocarcinoma Hep3B cells.6

1 Chan, C.B., De Leo, D., Joseph, J.W., et al. Increased uncoupling protein-2 levels in b-cells are associated with impaired glucose-stimulated insulin secretion mechanism of action. Diabetes 50 1302-1310 (2001).

2 Zhang, C., Baffy, G., Perret, P., et al. Uncoupling protein-2 negatively regulates insulin secretion and is a major link between obesity, b cell dysfunction, and type 2 diabetes. Cell 105 745-755 (2001).

3 Sesti, G., Cardellini, M., Marini, M.A., et al. A common polymorphism in the promoter of UCP2 contributes to the variation in insulin secretion in glucose-tolerant subjects. Diabetes 52 1280-1283 (2003).

4 Parton, L.E., Ye, C.P., Coppari, R., et al. Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity. Nature 449 228-232 (2007).

5 Zhang, C., Parton, L.E., Ye, C.P., et al. Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity-and high glucose-induced b cell dysfunction in isolated pancreatic islets. Cell Metab 3 417-427 (2006).

6 Kim, B., Kim, H., Lee, S., et al. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochem Pharmacol 70 1398-1407 (2005).

Synonyms
  • (+)-Genipin
Formal Name 1R,​4aS,​5,​7aS-​tetrahydro-​1-​hydroxy-​7-​(hydroxymethyl)-​cyclopenta[c]pyran-​4-​carboxylic acid,​ methyl ester
CAS Number 6902-77-8
Molecular Formula C11H14O5
Formula Weight 226.2
Formulation A crystalline solid
Purity ≥98%
λmax 240 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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COC(=O)​C1=COC(O)​C2C(=CCC12)​CO
InCHI Code
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​1S/C11H14O5/c1-15-10(13)​8-5-16-11(14)​9-6(4-12)​2-3-7(8)​9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7?,9?,11-/m1/s1
InCHI Key
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AZKVWQKMDGGDSV-LKXRVVKTSA-N

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Size Price Quantity Subtotal
5 mg $13.00 $0.00
10 mg $25.00 $0.00
25 mg $59.00 $0.00
50 mg $104.00 $0.00
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Pricing updated 2014-04-18. Prices are subject to change without notice.

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