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Chemical Compound Review

Nobiletin     2-(3,4-dimethoxyphenyl)- 5,6,7,8...

Synonyms: CHEMBL76447, S2333_Selleck, SureCN244029, CCRIS 9012, AG-K-18756, ...
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Disease relevance of C10112

  • Nobiletin inhibited the tumor-invasive activity of human fibrosarcoma HT-1080 cells in the Matrigel model, whereas a similar inhibition was observed upon exogenously adding tissue inhibitors of metalloproteinases (TIMPs)-1 and -2 [1].
  • Here we describe that nobiletin itself induces neurite outgrowth in PC12D cells, a rat pheochromocytoma cell line, like NGF, and the molecular mechanism of its neurotrophic action [2].
  • CONCLUSIONS: Although the effective dose and administration route of nobiletin require further investigation, our study represents a potential successful linking of this compound with the treatment of gastric cancer [3].
  • Furthermore, topical treatment of nobiletin on the skin of the back prevented the UVB-induced increase of transepidermal water loss and hyperplasia of the epidermis in hairless mice [4].
  • In this study, we examine the effects of tangeretin and its structure-related compound, nobiletin, on the expression of cyclooxygenases-2 (COX-2) in human lung epithelial carcinoma cells, A549, and human non-small cell lung carcinoma cells, H1299 [5].

Psychiatry related information on C10112


High impact information on C10112

  • In contrast, the gene expression and production of TIMP-1, but not TIMP-2, were enhanced by nobiletin [1].
  • The gene expression and production of pro-matrix metalloproteinase 9 (proMMP-9)/progelatinase B and proMMP-1/interstitial procollagenase were specifically suppressed by nobiletin in 12-O-tetradecanoylphorbol 13-acetate-stimulated HT-1080 cells [1].
  • These results suggest that nobiletin inhibits tumor cell invasive activity not only by suppressing the expression of MMPs but also augmenting TIMP-1 production in tumor cells, and that the nobiletin-mediated inhibition of activator protein-1 binding activity is at least partly involved in the suppression of MMP expression [1].
  • Furthermore, a phosphatidylinositol 3-kinase inhibitor, LY-294002, was found to mimic the different actions of nobiletin on the production of proMMP-9 and TIMP-1 [1].
  • Inhibitory effect of citrus nobiletin on phorbol ester-induced skin inflammation, oxidative stress, and tumor promotion in mice [8].

Chemical compound and disease context of C10112


Biological context of C10112


Anatomical context of C10112

  • Nobiletin significantly inhibited two distinct stages of skin inflammation induced by double TPA application [first stage priming (leukocyte infiltration) and second stage activation (oxidative insult by leukocytes)] by decreasing the inflammatory parameters [8].
  • Nobiletin-induced neurite outgrowth was inhibited by PD98059 and U0126 but not K252a [2].
  • As cultured in the presence of nobiletin or NGF for 48 h and then assayed using a scanning electron microscope, PC12D cells treated with nobiletin showed morphology with flatter and larger cell bodies than the cells cultured with NGF [2].
  • In addition, nobiletin downregulated the IL-1-induced gene expression and production of proMMP-1/procollagenase-1 and proMMP-3/prostromelysin-1 in human synovial fibroblasts [14].
  • Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro [4].

Associations of C10112 with other chemical compounds


Gene context of C10112


Analytical, diagnostic and therapeutic context of C10112

  • Nevertheless, nobiletin did not affect SR-A protein expression, as measured by Western blot analysis, nor was cell surface expression of SR-A affected as measured by 4 degrees C binding studies using [125I]acLDL [17].
  • Furthermore, a 11-day oral administration of nobiletin rescued impaired memory in olfactory-bulbectomized mice documented to be accompanied by a cholinergic neurodegeneration [20].
  • Because of the antimutagenic properties the Citrus flavonoids tested, especially tangeretin and nobiletin, might play a role in the chemoprevention of cancer [21].
  • The enzymatic activity of MMP-9 expressed in culture medium obtained from a co-culture of TMK-1 and mouse fibroblastic cells was inhibited by nobiletin in a concentration-dependent manner [22].
  • However, conventional normal-phase silica gel chromatography and C(18)-reverse-phase separation methods cannot satisfy the requirement of pure and gram scale nobiletin in a timely manner [23].


  1. Inhibition of activator protein-1 binding activity and phosphatidylinositol 3-kinase pathway by nobiletin, a polymethoxy flavonoid, results in augmentation of tissue inhibitor of metalloproteinases-1 production and suppression of production of matrix metalloproteinases-1 and -9 in human fibrosarcoma HT-1080 cells. Sato, T., Koike, L., Miyata, Y., Hirata, M., Mimaki, Y., Sashida, Y., Yano, M., Ito, A. Cancer Res. (2002) [Pubmed]
  2. Mechanism of neurotrophic action of nobiletin in PC12D cells. Nagase, H., Yamakuni, T., Matsuzaki, K., Maruyama, Y., Kasahara, J., Hinohara, Y., Kondo, S., Mimaki, Y., Sashida, Y., Tank, A.W., Fukunaga, K., Ohizumi, Y. Biochemistry (2005) [Pubmed]
  3. Anti-tumour effects of nobiletin, a citrus flavonoid, on gastric cancer include: antiproliferative effects, induction of apoptosis and cell cycle deregulation. Yoshimizu, N., Otani, Y., Saikawa, Y., Kubota, T., Yoshida, M., Furukawa, T., Kumai, K., Kameyama, K., Fujii, M., Yano, M., Sato, T., Ito, A., Kitajima, M. Aliment. Pharmacol. Ther. (2004) [Pubmed]
  4. Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Tanaka, S., Sato, T., Akimoto, N., Yano, M., Ito, A. Biochem. Pharmacol. (2004) [Pubmed]
  5. Tangeretin suppresses IL-1beta-induced cyclooxygenase (COX)-2 expression through inhibition of p38 MAPK, JNK, and AKT activation in human lung carcinoma cells. Chen, K.H., Weng, M.S., Lin, J.K. Biochem. Pharmacol. (2007) [Pubmed]
  6. Nobiletin restoring beta-amyloid-impaired CREB phosphorylation rescues memory deterioration in Alzheimer's disease model rats. Matsuzaki, K., Yamakuni, T., Hashimoto, M., Haque, A.M., Shido, O., Mimaki, Y., Sashida, Y., Ohizumi, Y. Neurosci. Lett. (2006) [Pubmed]
  7. Pharmacological profile of gastric mucosal protection by marmin and nobiletin from a traditional herbal medicine, Aurantii fructus immaturus. Takase, H., Yamamoto, K., Hirano, H., Saito, Y., Yamashita, A. Jpn. J. Pharmacol. (1994) [Pubmed]
  8. Inhibitory effect of citrus nobiletin on phorbol ester-induced skin inflammation, oxidative stress, and tumor promotion in mice. Murakami, A., Nakamura, Y., Torikai, K., Tanaka, T., Koshiba, T., Koshimizu, K., Kuwahara, S., Takahashi, Y., Ogawa, K., Yano, M., Tokuda, H., Nishino, H., Mimaki, Y., Sashida, Y., Kitanaka, S., Ohigashi, H. Cancer Res. (2000) [Pubmed]
  9. A citrus flavonoid, nobiletin, suppresses production and gene expression of matrix metalloproteinase 9/gelatinase B in rabbit synovial fibroblasts. Ishiwa, J., Sato, T., Mimaki, Y., Sashida, Y., Yano, M., Ito, A. J. Rheumatol. (2000) [Pubmed]
  10. Antiproliferative effects of citrus flavonoids on a human squamous cell carcinoma in vitro. Kandaswami, C., Perkins, E., Soloniuk, D.S., Drzewiecki, G., Middleton, E. Cancer Lett. (1991) [Pubmed]
  11. Activation and inhibition of benzo(a)pyrene and aflatoxin B1 metabolism in human liver microsomes by naturally occurring flavonoids. Buening, M.K., Chang, R.L., Huang, M.T., Fortner, J.G., Wood, A.W., Conney, A.H. Cancer Res. (1981) [Pubmed]
  12. Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on p-glycoprotein-mediated transport of talinolol in caco-2 cells. Mertens-Talcott, S.U., Castro, W.V., Manthey, J.A., Derendorf, H., Butterweck, V. J. Agric. Food Chem. (2007) [Pubmed]
  13. Dietary administration of citrus nobiletin inhibits azoxymethane-induced colonic aberrant crypt foci in rats. Kohno, H., Yoshitani, S., Tsukio, Y., Murakami, A., Koshimizu, K., Yano, M., Tokuda, H., Nishino, H., Ohigashi, H., Tanaka, T. Life Sci. (2001) [Pubmed]
  14. Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Lin, N., Sato, T., Takayama, Y., Mimaki, Y., Sashida, Y., Yano, M., Ito, A. Biochem. Pharmacol. (2003) [Pubmed]
  15. Wogonin and fisetin induce apoptosis in human promyeloleukemic cells, accompanied by a decrease of reactive oxygen species, and activation of caspase 3 and Ca(2+)-dependent endonuclease. Lee, W.R., Shen, S.C., Lin, H.Y., Hou, W.C., Yang, L.L., Chen, Y.C. Biochem. Pharmacol. (2002) [Pubmed]
  16. In vitro and in vivo activation of oxidative drug metabolism by flavonoids. Lasker, J.M., Huang, M.T., Conney, A.H. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  17. Nobiletin, a citrus flavonoid isolated from tangerines, selectively inhibits class A scavenger receptor-mediated metabolism of acetylated LDL by mouse macrophages. Whitman, S.C., Kurowska, E.M., Manthey, J.A., Daugherty, A. Atherosclerosis (2005) [Pubmed]
  18. Effects of flavonoids on cytochrome P450-dependent acetaminophen metabolism in rats and human liver microsomes. Li, Y., Wang, E., Patten, C.J., Chen, L., Yang, C.S. Drug Metab. Dispos. (1994) [Pubmed]
  19. Activation of protein kinase C betaII/epsilon-c-Jun NH2-terminal kinase pathway and inhibition of mitogen-activated protein/extracellular signal-regulated kinase 1/2 phosphorylation in antitumor invasive activity induced by the polymethoxy flavonoid, nobiletin. Miyata, Y., Sato, T., Yano, M., Ito, A. Mol. Cancer Ther. (2004) [Pubmed]
  20. Nobiletin and its related flavonoids with CRE-dependent transcription-stimulating and neuritegenic activities. Nagase, H., Omae, N., Omori, A., Nakagawasai, O., Tadano, T., Yokosuka, A., Sashida, Y., Mimaki, Y., Yamakuni, T., Ohizumi, Y. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  21. Inhibition of bacterial mutagenesis by Citrus flavonoids. Calomme, M., Pieters, L., Vlietinck, A., Vanden Berghe, D. Planta Med. (1996) [Pubmed]
  22. The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Minagawa, A., Otani, Y., Kubota, T., Wada, N., Furukawa, T., Kumai, K., Kameyama, K., Okada, Y., Fujii, M., Yano, M., Sato, T., Ito, A., Kitajima, M. Jpn. J. Cancer Res. (2001) [Pubmed]
  23. Nobiletin: efficient and large quantity isolation from orange peel extract. Li, S., Yu, H., Ho, C.T. Biomed. Chromatogr. (2006) [Pubmed]
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