AdipoGen Life Sciences

Genipin

CHF 70.00
In stock
AG-CN2-0481-M02525 mgCHF 70.00
AG-CN2-0481-M100100 mgCHF 210.00
AG-CN2-0481-M500500 mgCHF 490.00
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Product Details
Synonyms (+)-Genipin; Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Product Type Chemical
Properties
Formula

C11H14O5

MW 226.2
CAS 6902-77-8
RTECS GY5828000
Source/Host Chemicals Isolated from Gardenia jasminoides Ellis fruits.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in DMSO (50mg/ml), ethanol (5mg/ml), methanol or acetone. Slightly soluble in water.
InChi Key AZKVWQKMDGGDSV-BCMRRPTOSA-N
Smiles [H][C@]12CC=C(CO)[C@@]1([H])[C@H](O)OC=C2C(=O)OC
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Cell permeable inhibitor of uncoupling protein 2 (UCP2).
  • Increases glucose-stimulated insulin secretion, mitochondrial membrane potential and ATP levels in pancreatic island cells.
  • Anticancer, antimetastatic and anti-angiogenic agent. Increases Bax/Bcl-2 ratio and induces PARP cleavage and caspase-3- and caspase-9-mediated apoptosis in non-small cell lung cancer (NSCLC) cells. Sensitizes multidrug-resistant cancer cells to cytotoxic agents through UCP2 inhibition. Suppresses the tumor promoting function of UCP2 in a cellular model of Warburg effect.
  • Anti-inflammatory agent. Upregulates nNOS (neuronal nitric oxide synthase/NOS I) and decreases acute inflammation through inhibition of LPS-induced NF-κB activity. Inhibits toll-like receptor (TLR) signaling and the production of pro-inflammatory cytokines, preventing sepsis and increasing survival in animal models of infection.
  • Modulates NLRP3 inflammasome activation and ATP- or H2O2-mediated IL-1β release. Inhibits NLRP3 and NLRC4 inflammasome activation via autophagy suppression.
  • Antiviral compound. Chemical promoter of Epstein-Barr virus (EBV) lytic cycle activation and suppressor of EBV infection.
  • Shown to have wound healing, neuroprotective, antidepressant, anti-osteoporotic and antioxidative activities.
  • Protein, collagen, gelatin and chitosan natural cross-linking agent. 5,000-10,000 times less cytotoxic than any other crosslinking agents, with favorable properties of use in the range of pH 7.4-8.5 and temperatures between 25-45°C.
  • Shown to be useful in the construction of novel drug delivery systems, as the raw material for gardenia blue pigment preparation and as the intermediate for alkaloid syntheses.
  • Produces blue colored pigments by binding to amino acids. Simple, safe, sensitive and stable alternative for colorimetric determination of amino acids.
  • Shown in forensic research to be a novel fingerprint reagent with colorimetric and fluorogenic activity.
Product References
  1. Naturally occurring oxygen heterocyclics. IX. Isolation and characterization of genipin: C. Djerassi, et al.; J. Org. Chem. 25, 2174 (1960)
  2. Prevention of the neurotoxicity of the amyloid beta protein by genipin: M. Yamazaki, et al.; Biol. Pharm. Bull. 24, 1454 (2001)
  3. Colorimetric determination of amino acids using genipin from Gardenia jasminoides: S.W. Lee, et al.;  Anal. Chim. Acta 480, 267 (2003)
  4. Genipin-a novel fingerprint reagent with colorimetric and fluorogenic activity: J. Almog, et al.; J. Forensic Sci. 49, 255 (2004)
  5. Cyclic GMP-dependent neurite outgrowth by genipin and nerve growth factor in PC12h cells: M. Yamazaki, et al.; Eur. J. Pharmacol. 488, 35 (2004)
  6. Antiinflammatory effects of genipin, an active principle of gardenia: H.J. Koo, et al.; Eur. J. Pharmacol. 495, 201 (2004)
  7. 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)
  8. Genipin exhibits neurotrophic effects through a common signaling pathway in nitric oxide synthase-expressing cells: M. Yamazaki & K. Chiba; Eur. J. Pharmacol. 581, 255 (2008)
  9. Neuroprotective action of genipin on tunicamycin-induced cytotoxicity in neuro2a cells: M. Tanaka, et al.; Biol. Pharm. Bull. 32, 1220 (2009)
  10. Antidepressant-like effect of genipin in mice: J.S. Tian, et al.; Neurosci. Lett. 479, 236 (2010)
  11. Genipin induced apoptosis associated with activation of the c-Jun NH2-terminal kinase and p53 protein in HeLa cells: H. Cao, et al.; Biol. Pharm. Bull. 33, 1343 (2010)
  12. Genipin-induced inhibition of uncoupling protein-2 sensitizes drug-resistant cancer cells to cytotoxic agents: R.J. Mailloux, et al.; PLoS One 5, e13289 (2010)
  13. Cellular model of Warburg effect identifies tumor promoting function of UCP2 in breast cancer and its suppression by genipin: V. Ayyasamy, et al.; PLoS One 6, e24792 (2011)
  14. Genipin attenuates sepsis by inhibiting Toll-like receptor signalling: T.H. Kim, et al.; Mol. Med. 18, 455 (2012)
  15. Up-regulation of TIMP-1 by genipin inhibits MMP-2 activities and suppresses the metastatic potential of human hepatocellular carcinoma: N. Wang, et al.; PLoS One 7, e46318 (2012)
  16. Genipin - the natural water soluble cross-linking agent and its importance in the modified drug delivery systems: an overview: B. Manickam, et al.; Curr. Drug Deliv. 11, 139 (2014) (Review)
  17. Genipin inhibits RANKL-induced osteoclast differentiation through proteasome-mediated degradation of c-Fos protein and suppression of NF-κB activation: C.H. Lee, et al.; J. Pharmacol. Sci. 124, 344 (2014)
  18. Genipin as a novel chemical activator of EBV lytic cycle: M. Son, et al.; J. Microbiol. 53, 155 (2015)
  19. Genipin suppresses NLRP3 inflammasome activation through uncoupling protein-2: V. Rajanbabu, et al.; Cell Immunol. 297, 40 (2015)
  20. Genipin inhibits NLRP3 and NLRC4 inflammasome activation via autophagy suppression: S.X. Yu, et al.; Sci. Rep. 5, 17935 (2015)
  21. Improved Physiochemical Properties of Chitosan@PCL Nerve Conduits by Natural Molecule Crosslinking: M. Bianchini, et al.; Biomolecules 13, 1712 (2023)
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