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Genipin & Cancer

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Genipin & Cancer

Product Abstract:

Genipin is extracted from gardenia fruit.The white crystal can be used as material in researching of treating cancer.


Product Description

GENERAL INFORMATION

Genipin is an aglycone derived from geniposide, which is found in the fruit of Gardenia jasminoides Ellis.  Djerassi and his colleagues discovered the structure of Genipin in the 1960’s using NMR spectroscopic data and chemical degradation experiments.  It possesses the molecular formula C11H14Oand contains a dihydropyran ring.1  Genipin itself is colorless but it reacts spontaneously with amino acids to form blue pigments.2  The blue pigments are edible and are currently being used as a blue food colorant in East Asia.3  The structure of Genipin is shown in Figure 1 along with other characteristics. 

Molecular Formula: C11H14O51

Molecular Weight: 226.227 4

Melting Point: 120-121 °C 2

Systematic Name: Cyclopenta(c) pyran-4-carboxylic acid, 1,4a-alpha,5,7a-alpha-tetrahydro-1-hydroxy-7-(hydroxymethyl)-, methyl ester4

Registry Number: 6902-77-8

Application:   Genipin & Cancer

1.Du G, Sun T, Zhang Y, Lin H, Li J, Liu W, Wang Y, Zhao B, Li H, Liu Y. The mitochondrial dysfunction plays an important role ?in urethane-induced lung carcinogenesis. Eur J Pharmacol. 2013 Sep 5;715(1-3):395-404. doi: 10.1016/j.ejphar.2013.04.031. Epub 2013 May 22.

PMID:23707353

 

 

2. Zhang Q, Dong P, Chen L, Wang X, Lu S.Genipin-cross-linked thermosensitive silk sericin/poly(N-isopropylacrylamide) hydrogels for cell proliferation and rapid detachment.

J Biomed Mater Res A. 2013 Apr 18. doi: 10.1002/jbm.a.34670. [Epub ahead of print]

PMID:23606462

 

3. Yang X, Yao J, Luo Y, Han Y, Wang Z, Du L.P38 MAP kinase mediates apoptosis after genipin treatment in non-small-cell lung cancer H1299 cells via a mitochondrial apoptotic cascade. J Pharmacol Sci. 2013;121(4):272-81.

PMID:23603895

 

4. Nam MK, Shin HA, Han JH, Park DW, Rhim H.Essential roles of mitochondrial depolarization in neuron loss through microglial activation and attraction toward neurons. Brain Res. 2013 Apr 10;1505:75-85. doi: 10.1016/j.brainres.2013.02.005. Epub 2013 Feb 12.

PMID:23415650

 

5. Elzoghby AO, Helmy MW, Samy WM, Elgindy NA.Spray-dried casein-based micelles as a vehicle for solubilization and controlled delivery of flutamide: formulation, characterization, and in vivo pharmacokinetics. Eur J Pharm Biopharm. 2013 Aug;84(3):487-96. doi: 10.1016/j.ejpb.2013.01.005. Epub 2013 Feb 9.

PMID:23403015

 

6. Dando I, Fiorini C, Pozza ED, Padroni C, Costanzo C, Palmieri M, Donadelli M. UCP2 inhibition triggers ROS-dependent nuclear translocation of GAPDH and autophagic cell death in pancreatic adenocarcinoma cells.Biochim Biophys Acta. 2013 Mar;1833(3):672-9. doi: 10.1016/j.bbamcr.2012.10.028. Epub 2012 Nov 2.

PMID:23124112

 

7. Wang N, Zhu M, Tsao SW, Man K, Zhang Z, Feng Y.Up-regulation of TIMP-1 by genipin inhibits MMP-2 activities and suppresses the metastatic potential of human hepatocellular carcinoma. PLoS One. 2012;7(9):e46318. doi: 10.1371/journal.pone.0046318. Epub 2012 Sep 28.

PMID:23029478

 

8. Liu Y, Jiang H, Xing FQ, Huang WJ, Mao LH, He LY. Uncoupling protein 2 expression affects androgen synthesis in polycystic ovary syndrome.Endocrine. 2013 Jun;43(3):714-23. doi: 10.1007/s12020-012-9802-0. Epub 2012 Sep 25.

PMID: 23008094

 

9. Chung EY, Kim HM, Lee GH, Kwak BK, Jung JS, Kuh HJ, Lee J. Design of deformable chitosan microspheres loaded with superparamagnetic iron oxide nanoparticles for embolotherapy detectable by magnetic resonance imaging. Carbohydr Polym. 2012 Nov 6;90(4):1725-31. doi: 10.1016/j.carbpol.2012.07.058. Epub 2012 Jul 31.

PMID: 22944439

 

10. Dalla Pozza E, Fiorini C, Dando I, Menegazzi M, Sgarbossa A, Costanzo C, Palmieri M, Donadelli M.  Role of mitochondrial uncoupling protein 2 in cancer cell resistance to gemcitabine. Biochim Biophys Acta. 2012 Oct;1823(10):1856-63. doi: 10.1016/j.bbamcr.2012.06.007. Epub 2012 Jun 15.

PMID:22705884

 

11. Kim ES, Jeong CS, Moon A. Genipin, a constituent of Gardenia jasminoides Ellis, induces apoptosis and inhibits invasion in MDA-MB-231 breast cancer cells.Oncol Rep. 2012 Feb;27(2):567-72. doi: 10.3892/or.2011.1508. Epub 2011 Oct 20.

PMID:22020372

 

12. Ayyasamy V, Owens KM, Desouki MM, Liang P, Bakin A, Thangaraj K, Buchsbaum DJ, LoBuglio AF, Singh KK. Cellular model of Warburg effect identifies tumor promoting function of UCP2 in breast cancer and its suppression by genipin. PLoS One. 2011;6(9):e24792. doi: 10.1371/journal.pone.0024792. Epub 2011 Sep 15.

PMID: 21935467

 

13. Moura MJ, Faneca H, Lima MP, Gil MH, Figueiredo MM. In situ forming chitosan hydrogels prepared via ionic/covalent co-cross-linking. Biomacromolecules. 2011 Sep 12;12(9):3275-84. doi: 10.1021/bm200731x. Epub 2011 Jul 28.

PMID:21774479

 

14. Feng Q, Cao HL, Xu W, Li XR, Ren YQ, Du LF. Apoptosis induced by genipin in human leukemia K562 cells: involvement of c-Jun N-terminal kinase in G?/M arrest.Acta Pharmacol Sin. 2011 Apr;32(4):519-27. doi: 10.1038/aps.2010.158. Epub 2011 Mar 14.

PMID: 21399655

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