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Genipin

Genipin

Product ID G1853
Cas No. 6902-77-8
Purity ≥99%
Product Unit SizeCostQuantityStock
25 mg $102.90 In stock
100 mg $288.80 In stock
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  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
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  • Downloads
  • References
  • Custom Order

Description

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 wound 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.

Product Info

Cas No.

6902-77-8

Purity

≥99%

Formula

C11H14O5

Formula Wt.

226.23

Chemical Name

methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

IUPAC Name

methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5, 7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Appearance

White Crystal Powder

Shipping and Storage

Store Temp

Ambient

Ship Temp

Ambient

Downloads

MSDS

G1853 MSDS PDF

Info Sheet

G1853 Info Sheet PDF

References

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.

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