Geniposide
Geniposide is an iridoid glycoside found in species of Gardenia that exhibits antioxidative, anti-diabetic, anti-inflammatory, neuroprotective, antiviral, and antithrombotic activities. Geniposide induces phase II enzymes and increases expression of glutathione and glutathione peroxidase. Geniposide also inhibits phosphorylation of GSK-3β and stimulates expression of GLUT2, increasing insulin secretion in β cells. In LPS-stimulated epithelial cells, geniposide decreases production of toll-like receptor 4 (TLR4), IL-1β, IL-6, and TNF-α and downregulates activation of p38 MAPK, ERK, and NF-κB. In diabetic animal models of Alzheimer’s disease, geniposide decreases hippocampal levels of amyloid-β (Aβ). This compound also decreases enterovirus yields, infectious activity, and ribosomal entry by inhibiting viral protein translation. In vitro, geniposide inhibits collagen-induced platelet aggregation and activity of phospholipase A2 (PLA2).
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18926548
| Cas No. |
24512-63-8 |
|---|---|
| Purity |
≥98% |
| Formula |
C17H24O10 |
| Formula Wt. |
388.37 |
| IUPAC Name |
methyl(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate |
| Melting Point |
163-164°C |
| Solubility |
Soluble in water, methanol and ethanol. 24512-63-8 |
| Appearance |
White to off white powder |
Guo LX, Liu JH, Yin F. Regulation of insulin secretion by geniposide: possible involvement of phosphatidylinositol 3-phosphate kinase. Eur Rev Med Pharmacol Sci. 2014;18(9):1287-94. PMID: 24867506.
Song X, Zhang W, Wang T, et al. Geniposide Plays an Anti-inflammatory Role via Regulating TLR4 and Downstream Signaling Pathways in Lipopolysaccharide-Induced Mastitis in Mice. Inflammation. 2014 Apr 27. [Epub ahead of print]. PMID: 24771071.
Liu J, Guo L, Yin F, et al. Geniposide regulates glucose-stimulated insulin secretion possibly through controlling glucose metabolism in INS-1 cells. PLoS One. 2013 Oct 22;8(10):e78315. Erratum in: PLoS One. 2014;9(1). PMID: 24167617.
Liu J, Zhang Y, Deng X, et al. Geniposide decreases the level of Aβ1-42 in the hippocampus of streptozotocin-induced diabetic rats.
cta Biochim Biophys Sin (Shanghai). 2013 Sep;45(9):787-91. PMID: 23803411.
Suzuki Y, Kondo K, Ikeda Y, et al. Antithrombotic effect of geniposide and genipin in the mouse thrombosis model. Planta Med. 2001 Dec;67(9):807-10. PMID: 11745015.
Tseng T, Chu C, Wang C. Comparison of geniposide and its acetylated derivative for the inhibition of aflatoxin b1-induced DNA-repair synthesis in rat primary hepatocyte. Oncol Rep. 1994 Jan;1(1):165-8. PMID: 21607329.
