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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

AC1LEL6Z     4-[(2R,3R)-4-(3,4- dihydroxyphenyl)-2,3...

Synonyms: CTK0D8681, ZINC00056474, 103185-28-0
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  • In this report, we evaluated the growth-inhibitory effects of sulindac sulfide, a COX-1 and COX-2 inhibitor; exisulind (sulindac sulfone), a novel proapoptotic agent that does not inhibit COX enzymes; and nordihydroguaiaretic acid (NDGA), a lipoxygenase inhibitor on human lung cancer cell lines [1].
  • We conclude that the inhibitors of eicosanoid biosynthesis, NDGA and 5,8,11,14-eicosatetraynoic acid, not only suppress glioblastoma cell proliferation, but also induce increased astrocytic differentiation [2].
  • The inhibited glioma cells demonstrated an increase in the number and length of astrocytic processes containing greater numbers of glial filaments, and the NDGA-treated cells also demonstrated extensive lateral pseudopod formation along the processes [2].
  • The present procedure, implemented in Fortran 90 and named TGSA-Flex, is deeply detailed and tested over four molecular sets: amino acids, nordihydroguaiaretic acid (NDGA) derivatives, HIV-1 protease inhibitors, and 1-[2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) derivatives [3].
  • Induction of PCA by Escherichia coli was similarly inhibited (E. coli 10(6) alone = 518 +/- 130; with NDGA 3 microM = 234 +/- 100, n = 2) [4].

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Chemical compound and disease context of NORDIHYDROGUAIARETIC ACID






Associations of NORDIHYDROGUAIARETIC ACID with other chemical compounds



  • To rule out the possibility that NDGA will induce apoptosis because of the effects on proteins other than AP-1, we investigated the effect of another AP-1 inhibitor, SP600125, which is specific to Jun-N-terminal kinase [26].
  • Further evaluation of the apoptotic process revealed that NDGA and BFA induced a rapid dephosphorylation of BAD and decrease expression of Bcl-2 [27].
  • Pretreatment for 15 min with the lipoxygenase inhibitor nordihydroguaiaretic acid (NDGA; 50 microM), but not the cyclooxygenase inhibitor indomethacin (10 microM) or the epoxygenase inhibitor SKF525A (100 microM) inhibited the sustained response to CRF by 48% and the initial spike response to AVP by 38% [28].
  • Our results indicate that treatment of cells with NDGA enhances c-myc, p53, and bax protein levels [26].
  • In addition, volume regulation was inhibited by the lipoxygenase pathway antagonist nordihydroguaiaretic acid (NDGA, 10 microM), the 5 lipoxygenase antagonists AA-861 (5 microM) and curcumin (20 microM), and by the 5-lipoxygenase activating protein inhibitor L-655,298 (5 microM) [29].

Analytical, diagnostic and therapeutic context of NORDIHYDROGUAIARETIC ACID


  1. Synergistic effects of new chemopreventive agents and conventional cytotoxic agents against human lung cancer cell lines. Soriano, A.F., Helfrich, B., Chan, D.C., Heasley, L.E., Bunn, P.A., Chou, T.C. Cancer Res. (1999) [Pubmed]
  2. Ultrastructural evidence for differentiation in a human glioblastoma cell line treated with inhibitors of eicosanoid metabolism. Wilson, D.E., Anderson, K.M., Seed, T.M. Neurosurgery (1990) [Pubmed]
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  5. Inhibitors of PLA2 and NO synthase cooperate in producing amnesia of a spatial task. Hölscher, C., Canevari, L., Richter-Levin, G. Neuroreport (1995) [Pubmed]
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  8. Endogenous non-cyclooxygenase metabolites of arachidonic acid modulate growth and mRNA levels of immediate-early response genes in rat mesangial cells. Sellmayer, A., Uedelhoven, W.M., Weber, P.C., Bonventre, J.V. J. Biol. Chem. (1991) [Pubmed]
  9. Phospholipase A2 inhibition prevents mucosal damage associated with small intestinal ischaemia in rats. Otamiri, T., Lindahl, M., Tagesson, C. Gut (1988) [Pubmed]
  10. Recurrence of microbial keratitis concomitant with antiinflammatory treatment in an animal model. Gritz, D.C., Kwitko, S., Trousdale, M.D., Gonzalez, V.H., McDonnell, P.J. Cornea (1992) [Pubmed]
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  12. Antioxidants stimulate transcriptional activation of the c-fos gene by multiple pathways in human fetal lung fibroblasts (WI-38). Keogh, B., Allen, R.G., Tresini, M., Furth, J.J., Cristofalo, V.J. J. Cell. Physiol. (1998) [Pubmed]
  13. Involvement of glycogen synthase kinase-3beta and tau phosphorylation in neuronal Golgi disassembly. Elyaman, W., Yardin, C., Hugon, J. J. Neurochem. (2002) [Pubmed]
  14. Arachidonic acid protects against hypoxic injury in rat proximal tubules. Alkhunaizi, A.M., Yaqoob, M.M., Edelstein, C.L., Gengaro, P.E., Burke, T.J., Nemenoff, R.A., Schrier, R.W. Kidney Int. (1996) [Pubmed]
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  16. Reversible inhibition of lymphokine-activated killer cell activity by lipoxygenase-pathway inhibitors. Sibbitt, W.L., Imir, T., Bankhurst, A.D. Int. J. Cancer (1986) [Pubmed]
  17. Modulation of ion transport in cultured rabbit tracheal epithelium by lipoxygenase metabolites. Egan, M.E., Wagner, M.H., Zeitlin, P.L., Guggino, W.B. Am. J. Respir. Cell Mol. Biol. (1992) [Pubmed]
  18. Biotransformation of aflatoxin B1 in human lung. Donnelly, P.J., Stewart, R.K., Ali, S.L., Conlan, A.A., Reid, K.R., Petsikas, D., Massey, T.E. Carcinogenesis (1996) [Pubmed]
  19. Endotoxin provocation of experimental renal cystic disease. Gardner, K.D., Reed, W.P., Evan, A.P., Zedalis, J., Hylarides, M.D., Leon, A.A. Kidney Int. (1987) [Pubmed]
  20. A comparative study on the effects of inhibitors of the lipoxygenase pathway on neutrophil function. Inhibitory effects on neutrophil function may not be attributed to inhibition of the lipoxygenase pathway. Ozaki, Y., Ohashi, T., Niwa, Y. Biochem. Pharmacol. (1986) [Pubmed]
  21. Reductive inactivation of soybean lipoxygenase 1 by catechols: a possible mechanism for regulation of lipoxygenase activity. Kemal, C., Louis-Flamberg, P., Krupinski-Olsen, R., Shorter, A.L. Biochemistry (1987) [Pubmed]
  22. The regulation of mitogenesis and apoptosis in response to the persistent stimulation of alpha1-adrenoceptors: a possible role of 15-lipoxygenase. Nishio, E., Watanabe, Y. Br. J. Pharmacol. (1997) [Pubmed]
  23. Inhibitory effects of MK-886 on arachidonic acid metabolism in human phagocytes. Ménard, L., Pilote, S., Naccache, P.H., Laviolette, M., Borgeat, P. Br. J. Pharmacol. (1990) [Pubmed]
  24. Cyclooxygenase- and lipoxygenase-dependent relaxation to arachidonic acid in rabbit small mesenteric arteries. Zhang, D.X., Gauthier, K.M., Chawengsub, Y., Holmes, B.B., Campbell, W.B. Am. J. Physiol. Heart Circ. Physiol. (2005) [Pubmed]
  25. Comparison of the effects of intra-arterial and aerosol administration of endothelin-1 (ET-1) in the guinea-pig isolated lung. Pons, F., Touvay, C., Lagente, V., Mencia-Huerta, J.M., Braquet, P. Br. J. Pharmacol. (1991) [Pubmed]
  26. Inhibition of AP-1 transcription activator induces myc-dependent apoptosis in HL60 cells. Park, S., Hahm, E.R., Lee, D.K., Yang, C.H. J. Cell. Biochem. (2004) [Pubmed]
  27. BAD and Bcl-2 regulation are early events linking neuronal endoplasmic reticulum stress to mitochondria-mediated apoptosis. Elyaman, W., Terro, F., Suen, K.C., Yardin, C., Chang, R.C., Hugon, J. Brain Res. Mol. Brain Res. (2002) [Pubmed]
  28. Role of lipoxygenase metabolites of arachidonic acid in the regulation of adrenocorticotropin secretion by perifused rat anterior pituitary cells. Won, J.G., Orth, D.N. Endocrinology (1994) [Pubmed]
  29. 5-Lipoxygenase metabolites of arachidonic acid regulate volume decrease by mudpuppy red blood cells. Light, D.B., Mertins, T.M., Belongia, J.A., Witt, C.A. J. Membr. Biol. (1997) [Pubmed]
  30. The release of a non-prostanoid inhibitory factor from rabbit bronchus detected by co-axial bioassay. Spina, D., Page, C.P. Br. J. Pharmacol. (1991) [Pubmed]
  31. Cyclooxygenase and lipoxygenase inhibitors act differently on oxidative product formation by immune mononuclear cells: a flow cytometric investigation. Rouahi, N., Levallois, C., Favier, F., Mani, J.C. Int. J. Immunopharmacol. (1989) [Pubmed]
  32. Group IIA secretory phospholipase A2 is a unique 12/15-lipoxygenase-regulated gene in cytokine-stimulated rat fibroblastic 3Y1 cells. Kuwata, H., Yamamoto, S., Takekura, A., Murakami, M., Kudo, I. Biochim. Biophys. Acta (2004) [Pubmed]
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