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Chemical Compound Review

apigenin     5,7-dihydroxy-2-(4- hydroxyphenyl)chromen-4...

Synonyms: Apigenol, Spigenin, Versulin, Apigenine, Chamomile, ...
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Disease relevance of apigenin

  • By week 33 after DMBA initiation, 48% of DMBA/TPA-treated mice developed carcinomas, while none occurred in DMBA/apigenin/TPA-treated groups [1].
  • In the first study, 20 mumol of apigenin was applied topically and no effect on body weight was observed [1].
  • The papilloma incidence for 0, 5, and 20 mumol apigenin at 26 weeks after DMBA was 93.3, 58, and 39.3%, and papilloma numbers per mouse were 7.5, 2.5, and 1.8, respectively [1].
  • Apigenin is a low toxicity and non-mutagenic phytopolyphenol and protein kinase inhibitor [2].
  • However, the one or more molecular mechanisms of apigenin-induced apoptosis in HER2/neu-overexpressing breast cancer cells remained to be elucidated [2].

Psychiatry related information on apigenin


High impact information on apigenin


Chemical compound and disease context of apigenin

  • Rhizobium leguminosarum biovars viciae, trifolii, and phaseoli have been grown in the presence and absence of 4',5,7-trihydroxyflavonone (naringenin) or 4',5,7-trihydroxyflavone (apigenin), which induce the expression of nodulation genes of the bacteria [11].
  • Apigenin, a common dietary flavonoid abundantly present in fruits and vegetables, may have the potential for prevention and therapy for prostate cancer [12].
  • These findings indicate that the inhibition of tumor cell metastasis by Apigenin or Quercetin may significantly depend on the ability of these compounds to alter the host's microenvironment, further substantiating the role of the intravascular processes in the metastatic cascade [13].
  • CONCLUSIONS: Chlorpromazine and apigenin might reduce the replication of adenovirus, which could provide a safety switch in case replication-associated side effects are encountered in patients [14].
  • Intraperitoneal administration of quercetin, apigenin, (-)-epigallocathechin-3-gallate (EGCG), resveratrol, and the anti-estrogen tamoxifen, at the time of i.m. injection of B16-BL6 cells into syngeneic mice, resulted in a significant, dose-dependent delay of tumor growth, without toxicity [15].

Biological context of apigenin


Anatomical context of apigenin

  • Exposure to UVB strongly increased COX-2 protein expression in mouse 308 keratinocytes, and this induction was inhibited by apigenin, a nonmutagenic bioflavonoid that has been shown to prevent mouse skin carcinogenesis induced by both chemical carcinogens and UV exposure [7].
  • Here we examined several human breast cancer cell lines having different levels of HER2/neu expression and found that apigenin exhibited potent growth-inhibitory activity in HER2/neu-overexpressing breast cancer cells but was much less effective for those cells expressing basal levels of HER2/neu [2].
  • Adhesion of leukocytes to cytokine-treated endothelial cells was blocked in endothelial cells cotreated with apigenin [19].
  • In addition, exposure of apigenin and kaempferol to cultured hepatocytes, mimicking first pass metabolism, greatly diminished the inhibitory effect of flavonoids on endothelial intercellular adhesion molecule 1 expression [20].
  • However, inhibition of lysosomal acidification with NH(4)Cl or chloroquine, or treating the cells with the hyaluronidase inhibitor apigenin increased intracellular hyaluronan staining, suggesting that it resided in prelysosomal endosomes [21].

Associations of apigenin with other chemical compounds


Gene context of apigenin

  • The steps in the ERK1/2 pathway relevant to the cytotoxic effects of apigenin, as well as the contribution of other signaling pathways, were investigated [24].
  • The effects of apigenin did not involve p38-MAPK or JNK1/2, and were not simply due to inhibition of PI3kinase or protein kinase CK2 [24].
  • In our efforts to understand the signaling pathway that mediates VEGF transcriptional activation, we found that apigenin inhibited AKT and p70S6K1 activation [25].
  • The inhibitory effects of apigenin and luteolin on ICAM-1 expression are mediated by the sequential attenuation of the three MAPKs activities, the c-fos and c-jun mRNA expressions, and the AP-1 transcriptional activity [26].
  • In the present study, we investigated the influence of apigenin on gtfB, gtfC, and gtfD expression in S. mutans UA159 [27].
  • P.o. administration of apigenin further resulted in increased levels of E-cadherin and decreased levels of nuclear beta-catenin, c-Myc, and cyclin D1 in the dorsolateral prostates of TRAMP mice [28].

Analytical, diagnostic and therapeutic context of apigenin


  1. Inhibitory effect of apigenin, a plant flavonoid, on epidermal ornithine decarboxylase and skin tumor promotion in mice. Wei, H., Tye, L., Bresnick, E., Birt, D.F. Cancer Res. (1990) [Pubmed]
  2. Apigenin induces apoptosis through proteasomal degradation of HER2/neu in HER2/neu-overexpressing breast cancer cells via the phosphatidylinositol 3-kinase/Akt-dependent pathway. Way, T.D., Kao, M.C., Lin, J.K. J. Biol. Chem. (2004) [Pubmed]
  3. Pharmacological profile of apigenin, a flavonoid isolated from Matricaria chamomilla. Avallone, R., Zanoli, P., Puia, G., Kleinschnitz, M., Schreier, P., Baraldi, M. Biochem. Pharmacol. (2000) [Pubmed]
  4. Medicinal plants for insomnia: a review of their pharmacology, efficacy and tolerability. Wheatley, D. J. Psychopharmacol. (Oxford) (2005) [Pubmed]
  5. Biologically active phenols from Saussurea medusa. Fan, C.Q., Yue, J.M. Bioorg. Med. Chem. (2003) [Pubmed]
  6. Phosphorylation on Thr-55 by TAF1 mediates degradation of p53: a role for TAF1 in cell G1 progression. Li, H.H., Li, A.G., Sheppard, H.M., Liu, X. Mol. Cell (2004) [Pubmed]
  7. Apigenin prevents UVB-induced cyclooxygenase 2 expression: coupled mRNA stabilization and translational inhibition. Tong, X., Van Dross, R.T., Abu-Yousif, A., Morrison, A.R., Pelling, J.C. Mol. Cell. Biol. (2007) [Pubmed]
  8. NKX3.1 is regulated by protein kinase CK2 in prostate tumor cells. Li, X., Guan, B., Maghami, S., Bieberich, C.J. Mol. Cell. Biol. (2006) [Pubmed]
  9. Regulatory effects of stem cell factor and interleukin-4 on adhesion of human mast cells to extracellular matrix proteins. Lorentz, A., Schuppan, D., Gebert, A., Manns, M.P., Bischoff, S.C. Blood (2002) [Pubmed]
  10. Flavonoids, dietary-derived inhibitors of cell proliferation and in vitro angiogenesis. Fotsis, T., Pepper, M.S., Aktas, E., Breit, S., Rasku, S., Adlercreutz, H., Wähälä, K., Montesano, R., Schweigerer, L. Cancer Res. (1997) [Pubmed]
  11. The degree of esterification and points of substitution by O-acetyl and O-(3-hydroxybutanoyl) groups in the acidic extracellular polysaccharides secreted by Rhizobium leguminosarum biovars viciae, trifolii, and phaseoli are not related to host range. O'Neill, M.A., Darvill, A.G., Albersheim, P. J. Biol. Chem. (1991) [Pubmed]
  12. Involvement of nuclear factor-kappa B, Bax and Bcl-2 in induction of cell cycle arrest and apoptosis by apigenin in human prostate carcinoma cells. Gupta, S., Afaq, F., Mukhtar, H. Oncogene (2002) [Pubmed]
  13. Flavonoids inhibit melanoma lung metastasis by impairing tumor cells endothelium interactions. Piantelli, M., Rossi, C., Iezzi, M., La Sorda, R., Iacobelli, S., Alberti, S., Natali, P.G. J. Cell. Physiol. (2006) [Pubmed]
  14. Chlorpromazine and apigenin reduce adenovirus replication and decrease replication associated toxicity. Kanerva, A., Raki, M., Ranki, T., S??rkioja, M., Koponen, J., Desmond, R.A., Helin, A., Stenman, U.H., Isoniemi, H., H??ckerstedt, K., Ristim??ki, A., Hemminki, A. The journal of gene medicine (2007) [Pubmed]
  15. Flavonoids apigenin and quercetin inhibit melanoma growth and metastatic potential. Caltagirone, S., Rossi, C., Poggi, A., Ranelletti, F.O., Natali, P.G., Brunetti, M., Aiello, F.B., Piantelli, M. Int. J. Cancer (2000) [Pubmed]
  16. Inducible IkappaB kinase/IkappaB kinase epsilon expression is induced by CK2 and promotes aberrant nuclear factor-kappaB activation in breast cancer cells. Eddy, S.F., Guo, S., Demicco, E.G., Romieu-Mourez, R., Landesman-Bollag, E., Seldin, D.C., Sonenshein, G.E. Cancer Res. (2005) [Pubmed]
  17. Apigenin Inhibition of Involucrin Gene Expression Is Associated with a Specific Reduction in Phosphorylation of Protein Kinase C{delta} Tyr311. Balasubramanian, S., Zhu, L., Eckert, R.L. J. Biol. Chem. (2006) [Pubmed]
  18. The neuroprotective effects of phytoestrogens on amyloid beta protein-induced toxicity are mediated by abrogating the activation of caspase cascade in rat cortical neurons. Wang, C.N., Chi, C.W., Lin, Y.L., Chen, C.F., Shiao, Y.J. J. Biol. Chem. (2001) [Pubmed]
  19. Flavonoids inhibit cytokine-induced endothelial cell adhesion protein gene expression. Gerritsen, M.E., Carley, W.W., Ranges, G.E., Shen, C.P., Phan, S.A., Ligon, G.F., Perry, C.A. Am. J. Pathol. (1995) [Pubmed]
  20. Dietary Flavonoids Attenuate Tumor Necrosis Factor {alpha}-induced Adhesion Molecule Expression in Human Aortic Endothelial Cells: STRUCTURE-FUNCTION RELATIONSHIPS AND ACTIVITY AFTER FIRST PASS METABOLISM. Lotito, S.B., Frei, B. J. Biol. Chem. (2006) [Pubmed]
  21. Hyaluronan enters keratinocytes by a novel endocytic route for catabolism. Tammi, R., Rilla, K., Pienimaki, J.P., MacCallum, D.K., Hogg, M., Luukkonen, M., Hascall, V.C., Tammi, M. J. Biol. Chem. (2001) [Pubmed]
  22. Protection by naringin and some other flavonoids of hepatocytic autophagy and endocytosis against inhibition by okadaic acid. Gordon, P.B., Holen, I., Seglen, P.O. J. Biol. Chem. (1995) [Pubmed]
  23. Polyphenols stimulate AMP-activated protein kinase, lower lipids, and inhibit accelerated atherosclerosis in diabetic LDL receptor-deficient mice. Zang, M., Xu, S., Maitland-Toolan, K.A., Zuccollo, A., Hou, X., Jiang, B., Wierzbicki, M., Verbeuren, T.J., Cohen, R.A. Diabetes (2006) [Pubmed]
  24. Unbalanced activation of ERK1/2 and MEK1/2 in apigenin-induced HeLa cell death. Llorens, F., Miró, F.A., Casañas, A., Roher, N., Garcia, L., Plana, M., Gómez, N., Itarte, E. Exp. Cell Res. (2004) [Pubmed]
  25. Apigenin inhibits expression of vascular endothelial growth factor and angiogenesis in human lung cancer cells: implication of chemoprevention of lung cancer. Liu, L.Z., Fang, J., Zhou, Q., Hu, X., Shi, X., Jiang, B.H. Mol. Pharmacol. (2005) [Pubmed]
  26. Flavonoids inhibit tumor necrosis factor-alpha-induced up-regulation of intercellular adhesion molecule-1 (ICAM-1) in respiratory epithelial cells through activator protein-1 and nuclear factor-kappaB: structure-activity relationships. Chen, C.C., Chow, M.P., Huang, W.C., Lin, Y.C., Chang, Y.J. Mol. Pharmacol. (2004) [Pubmed]
  27. Influence of apigenin on gtf gene expression in Streptococcus mutans UA159. Koo, H., Seils, J., Abranches, J., Burne, R.A., Bowen, W.H., Quivey, R.G. Antimicrob. Agents Chemother. (2006) [Pubmed]
  28. Blockade of beta-catenin signaling by plant flavonoid apigenin suppresses prostate carcinogenesis in TRAMP mice. Shukla, S., MacLennan, G.T., Flask, C.A., Fu, P., Mishra, A., Resnick, M.I., Gupta, S. Cancer Res. (2007) [Pubmed]
  29. Anaphylactic reaction after the ingestion of chamomile tea: a study of cross-reactivity with other composite pollens. Subiza, J., Subiza, J.L., Hinojosa, M., Garcia, R., Jerez, M., Valdivieso, R., Subiza, E. J. Allergy Clin. Immunol. (1989) [Pubmed]
  30. Suppression of constitutive and tumor necrosis factor alpha-induced nuclear factor (NF)-kappaB activation and induction of apoptosis by apigenin in human prostate carcinoma PC-3 cells: correlation with down-regulation of NF-kappaB-responsive genes. Shukla, S., Gupta, S. Clin. Cancer Res. (2004) [Pubmed]
  31. The chemopreventive flavonoid apigenin induces G2/M arrest in keratinocytes. Lepley, D.M., Li, B., Birt, D.F., Pelling, J.C. Carcinogenesis (1996) [Pubmed]
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