Genipin

SKU: orb1306097

Description

(+)-Genipin is the bioactive aglycone metabolite of geniposide, isolated from Gardenia jasminoides fruit. It is widely used in research for its cross-linking properties in biomaterials and is studied in vitro and in vivo for its effects on various biological pathways.

Research Area

Cell Biology

Key Properties

• CAS Number: 6902-77-8
• MW: 226.23
• Purity: 99.74% (May vary between batches)
• Formula: C₁₁H₁₄O₅
• SMILES: [H][C@]12CC=C(CO)[C@@]1([H])[C@H](O)OC=C2C(=O)OC
• Target: Autophagy
• Solubility: Ethanol:45 mg/mL (198.91 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:2 mg/mL (8.84 mM);H2O:1 mg/mL (4.42 mM);DMSO:252.5 mg/mL (1116.12 mM)

Bioactivity

• In Vitro:
  Genipin stimulats glucose uptake in a time- and dose-dependent manner. The maximal effect is achieved at 2 h with a concentration of 10 μM. In myotubes, genipin promotes glucose transporter 4 (GLUT4) translocation to the cell surface, which increases the phosphorylation of insulin receptor substrate-1 (IRS-1), AKT, and GSK3β. Meanwhile, genipin increases ATP levels, closed KATP channels, and then increases the concentration of calcium in the cytoplasm in C2C12 myotubes. Genipin-stimulated glucose uptake could be blocked by both the PI3-K inhibitor wortmannin and calcium chelator EGTA. Moreover, genipin increases the level of reactive oxygen species and ATP in C2C12 myotubes. Genipin increases mitochondrial membrane potential, which then increases ATP levels and closes KATP channels, thereby stimulating insulin secretion in pancreatic β-cells. Genipin activates glucose-excited POMC neurons. Cytochrome c content increases significantly in the cytosol of genipin-treated FaO cells. Activation of caspase-3 and caspase-7 is ultimately responsible for genipin-induced apoptotic process in hepatoma cells. ROS level notably increases in Hep3B cells treated with 200 μM genipin.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

crosslinking, DNMT1, diabetes, Cholagogues, Choleretics, antithrombosis, antitumor, anti-inflammation, Autophagy, (+)-Genipin, inhibit, immunosuppression, hippocampal, Genipin, Inhibitor, proteins, reagent, UCP2, type-2

Compound Identifiers

PubChem CID

442424