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Chemical Compound Review

SureCN9609096     methyl2-hydroxy-9- (hydroxymethyl)-3...

Synonyms: NSC-49633, NSC49633, LS-58154, AKOS015902656, AC1L2M4Y, ...
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Disease relevance of Genipin

  • CONCLUSIONS: TJ-135 may be useful for treatment of liver fibrosis and portal hypertension through suppression of activated hepatic stellate cell function by genipin, an absorbed form of its component [1].
  • Our observations imply that genipin signaling to apoptosis of hepatoma cells is mediated via NADPH oxidase-dependent generation of ROS, which leads to downstream of JNK [2].
  • On the other hand, no apparent degradation or thrombus formation was observed on the surfaces of the genipin-fixed valvular leaflet and conduit [3].
  • Media extracted from crosslinked genipin solder showed negligible toxicity to fibroblast cells under the culture conditions examined here [4].
  • Genipin exhibited significant topical antiinflammatory effect shown as an inhibition of croton oil-induced ear edema in mice [5].

High impact information on Genipin

  • Genipin also suppressed in vitro Fas-mediated apoptosis in primary-cultured murine hepatocytes [6].
  • Activation of caspase 3 and 8 in the liver homogenate and rapid reduction of triangle uppsi(m) of hepatocytes isolated from Jo2-treated mice were inhibited by genipin preadministration [6].
  • Genipin, a metabolite derived from the herbal medicine Inchin-ko-to, and suppression of Fas-induced lethal liver apoptosis in mice [6].
  • The resistance to Ca(2+)-induced MPT was enhanced in liver mitochondria of genipin-treated mice [6].
  • Biliary secretion of Mrp2 substrates and the protein mass, subcellular localization, and messenger RNA (mRNA) level of Mrp2 were assessed in rat liver after infusion of genipin, an intestinal bacterial metabolite of geniposide, a major ingredient of ICKT [7].

Chemical compound and disease context of Genipin


Biological context of Genipin


Anatomical context of Genipin

  • In immunoelectron microscopic studies, a marked increase in Mrp2 density in the canalicular membrane (CM) and microvilli was observed in the genipin-treated liver tissue sections when compared with the vehicle-treated liver tissue sections [7].
  • On the other hand, an inhibitor of soluble guanylate cyclase (SGC), which is known to be a stimulatory target of NO, abolished greatly the genipin-induced neurite outgrowth [9].
  • Such attenuation was not found in the cells cultured with geniposide, an iridoid compound of TJ-135, but genipin, an aglycone of geniposide formed in the gut by action of bacterial flora, markedly decreased stellate cell activation without affecting synthesis of proteins other than collagen [1].
  • The present study further investigates the crosslinking characteristics and mechanical properties of a genipin-fixed bovine pericardium [12].
  • An in vivo evaluation of a biodegradable genipin-cross-linked gelatin peripheral nerve guide conduit material [13].

Associations of Genipin with other chemical compounds


Gene context of Genipin

  • Activation of the mitogen-activated protein kinase cascade through nitric oxide synthesis as a mechanism of neuritogenic effect of genipin in PC12h cells [9].
  • Consistently, the stable expression of Nox1-C, a C-terminal region of Nox1 unable to generate ROS, blocked the formation of TUNEL-positive apoptotic cells, and activation of caspase-3 and JNK in FaO cells treated with genipin [2].
  • We examined the effects of genipin on production of TNF-alpha in vivo and in vitro [19].
  • In conclusion, the present findings suggest that genipin, a metabolite derived form the herbal medicine Inchinko-to improved acute liver dysfunction by suppressive effect of TNF-alpha production [19].
  • Genipin enhances Mrp2 (Abcc2)-mediated bile formation and organic anion transport in rat liver [7].

Analytical, diagnostic and therapeutic context of Genipin


  1. Japanese herbal medicine Inchin-ko-to as a therapeutic drug for liver fibrosis. Inao, M., Mochida, S., Matsui, A., Eguchi, Y., Yulutuz, Y., Wang, Y., Naiki, K., Kakinuma, T., Fujimori, K., Nagoshi, S., Fujiwara, K. J. Hepatol. (2004) [Pubmed]
  2. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Kim, B.C., Kim, H.G., Lee, S.A., Lim, S., Park, E.H., Kim, S.J., Lim, C.J. Biochem. Pharmacol. (2005) [Pubmed]
  3. Reconstruction of the right ventricular outflow tract with a bovine jugular vein graft fixed with a naturally occurring crosslinking agent (genipin) in a canine model. Chang, Y., Tsai, C.C., Liang, H.C., Sung, H.W. J. Thorac. Cardiovasc. Surg. (2001) [Pubmed]
  4. Albumin-genipin solder for laser tissue repair. Lauto, A., Foster, L.J., Ferris, L., Avolio, A., Zwaneveld, N., Poole-Warren, L.A. Lasers in surgery and medicine. (2004) [Pubmed]
  5. Antiinflammatory effects of genipin, an active principle of gardenia. Koo, H.J., Song, Y.S., Kim, H.J., Lee, Y.H., Hong, S.M., Kim, S.J., Kim, B.C., Jin, C., Lim, C.J., Park, E.H. Eur. J. Pharmacol. (2004) [Pubmed]
  6. Genipin, a metabolite derived from the herbal medicine Inchin-ko-to, and suppression of Fas-induced lethal liver apoptosis in mice. Yamamoto, M., Miura, N., Ohtake, N., Amagaya, S., Ishige, A., Sasaki, H., Komatsu, Y., Fukuda, K., Ito, T., Terasawa, K. Gastroenterology (2000) [Pubmed]
  7. Genipin enhances Mrp2 (Abcc2)-mediated bile formation and organic anion transport in rat liver. Shoda, J., Miura, T., Utsunomiya, H., Oda, K., Yamamoto, M., Kano, M., Ikegami, T., Tanaka, N., Akita, H., Ito, K., Suzuki, H., Sugiyama, Y. Hepatology (2004) [Pubmed]
  8. Antithrombotic effect of geniposide and genipin in the mouse thrombosis model. Suzuki, Y., Kondo, K., Ikeda, Y., Umemura, K. Planta Med. (2001) [Pubmed]
  9. Activation of the mitogen-activated protein kinase cascade through nitric oxide synthesis as a mechanism of neuritogenic effect of genipin in PC12h cells. Yamazaki, M., Chiba, K., Mohri, T., Hatanaka, H. J. Neurochem. (2001) [Pubmed]
  10. In vivo biocompatibility and degradability of a novel injectable-chitosan-based implant. Mi, F.L., Tan, Y.C., Liang, H.F., Sung, H.W. Biomaterials (2002) [Pubmed]
  11. Genipin suppression of fibrogenic behaviors of the alpha-TN4 lens epithelial cell line. Kitano, A., Saika, S., Yamanaka, O., Reinach, P.S., Ikeda, K., Okada, Y., Shirai, K., Ohnishi, Y. Journal of cataract and refractive surgery. (2006) [Pubmed]
  12. Crosslinking characteristics and mechanical properties of a bovine pericardium fixed with a naturally occurring crosslinking agent. Sung, H.W., Chang, Y., Chiu, C.T., Chen, C.N., Liang, H.C. J. Biomed. Mater. Res. (1999) [Pubmed]
  13. An in vivo evaluation of a biodegradable genipin-cross-linked gelatin peripheral nerve guide conduit material. Chen, Y.S., Chang, J.Y., Cheng, C.Y., Tsai, F.J., Yao, C.H., Liu, B.S. Biomaterials (2005) [Pubmed]
  14. Biocompatibility study of a biological tissue fixed with a naturally occurring crosslinking reagent. Huang, L.L., Sung, H.W., Tsai, C.C., Huang, D.M. J. Biomed. Mater. Res. (1998) [Pubmed]
  15. Effect of genipin-crosslinked chitin-chitosan scaffolds with hydroxyapatite modifications on the cultivation of bovine knee chondrocytes. Kuo, Y.C., Lin, C.Y. Biotechnol. Bioeng. (2006) [Pubmed]
  16. A novel pH-sensitive hydrogel composed of N,O-carboxymethyl chitosan and alginate cross-linked by genipin for protein drug delivery. Chen, S.C., Wu, Y.C., Mi, F.L., Lin, Y.H., Yu, L.C., Sung, H.W. Journal of controlled release : official journal of the Controlled Release Society. (2004) [Pubmed]
  17. Loading of a novel angiogenic agent, ginsenoside Rg1 in an acellular biological tissue for tissue regeneration. Liang, H.C., Chen, C.T., Chang, Y., Huang, Y.C., Chen, S.C., Sung, H.W. Tissue engineering. (2005) [Pubmed]
  18. Cyclic GMP-dependent neurite outgrowth by genipin and nerve growth factor in PC12h cells. Yamazaki, M., Chiba, K., Mohri, T., Hatanaka, H. Eur. J. Pharmacol. (2004) [Pubmed]
  19. Genipin prevents fulminant hepatic failure resulting in reduction of lethality through the suppression of TNF-alpha production. Takeuchi, S., Goto, T., Mikami, K., Miura, K., Ohshima, S., Yoneyama, K., Sato, M., Shibuya, T., Watanabe, D., Kataoka, E., Segawa, D., Endo, A., Sato, W., Yoshino, R., Watanabe, S. Hepatol. Res. (2005) [Pubmed]
  20. Fixation of biological tissues with a naturally occurring crosslinking agent: fixation rate and effects of pH, temperature, and initial fixative concentration. Sung, H.W., Chang, Y., Liang, I.L., Chang, W.H., Chen, Y.C. J. Biomed. Mater. Res. (2000) [Pubmed]
  21. Biological evaluation of chitosan salts cross-linked to genipin as a cell scaffold for disk tissue engineering. Mwale, F., Iordanova, M., Demers, C.N., Steffen, T., Roughley, P., Antoniou, J. Tissue engineering. (2005) [Pubmed]
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