Genipin
Genipin is an iridoid glycoside compound found in zhishi or Gardenia jasminoides; it is most well known for its protein cross-linking ability. Genipin displays anti-amnestic, wound healing, anticancer, neuroprotective, cognition enhancing, anti-inflammatory, and antioxidative activities. In animal models, genipin inhibits acetylcholine esterase (AChE) , attenuating scopolamine-induced memory impairment. In ex vivo and in vivo models, genipin increases would healing by inducing cross-linking of collagen. Genipin also exerts anticancer activity, as it increases the Bax/Bcl-2 ratio and induces PARP cleavage and caspase-3- and caspase-9-mediated apoptosis in non-small cell lung cancer (NSCLC) cells. In animal models, this compound upregulates nNOS and decreases acute inflammation through inhibition of LPS-induced NF-κB activity. Additionally, genipin inhibits Toll-like receptor (TLR) signaling and the production of pro-inflammatory cytokines, preventing sepsis and increasing survival in animal models of infection. Genipin also upregulates mitochondrial uncoupling protein 2 (UCP2) levels in the kidney, postponing progression of diabetic neuropathy in vivo.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18926488
| Cas No. |
6902-77-8 |
|---|---|
| Purity |
≥98% |
| Formula |
C11H14O5 |
| Formula Wt. |
226.23 |
| IUPAC Name |
methyl(1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate |
| Appearance |
White Crystal Powder |
Liu TX, Wang Z. Collagen crosslinking of porcine sclera using genipin. Acta Ophthalmol. 2013 Jun;91(4):e253-7. PMID: 23710671.
Nam Y, Lee D. Ameliorating effect of zhizi (Fructus gardeniae) extract and its glycosides on scopolamine-induced memory impairment. J Tradit Chin Med. 2013 Apr;33(2):223-7. PMID: 23789221.
Yang X, Yao J, Luo Y, et al. 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.
Aramwit P, Siritienthong T, Srichana T, et al. Accelerated healing of full-thickness wounds by genipin-crosslinked silk sericin/PVA scaffolds. Cells Tissues Organs. 2013;197(3):224-38. PMID: 23307034.
Mu C, Zhang K, Lin W, et al. Ring-opening polymerization of genipin and its long-range crosslinking effect on collagen hydrogel. J Biomed Mater Res A. 2013 Feb;101(2):385-93. PMID: 22847997.
Qiu W, Zhou Y, Jiang L, et al. Genipin inhibits mitochondrial uncoupling protein 2 expression and ameliorates podocyte injury in diabetic mice. PLoS One. 2012;7(7):e41391. PMID: 22848482.
Li CC, Hsiang CY, Lo HY, et al. Genipin inhibits lipopolysaccharide-induced acute systemic inflammation in mice as evidenced by nuclear factor-κB bioluminescent imaging-guided transcriptomic analysis. Food Chem Toxicol. 2012 Sep;50(9):2978-86. PMID: 22687549.
Kim TH, Yoon SJ, Lee SM. Genipin attenuates sepsis by inhibiting Toll-like receptor signaling. Mol Med. 2012 May 9;18:455-65. PMID: 22252713.
