Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Induction of the Anticarcinogenic Marker Enzyme, Quinone Reductase, by Dalbergiae Lignum

  • Published : 2004.09.01
Download PDF
⟨ Previous Next ⟩

Abstract

The effect of an extract of Dalbergiae Lignum and four components that were isolated from the extract on the anticarcinogenic phase II marker enzyme, quinone reductase (QR), was investi-gated. Of the solvent extracts of Dalbergiae Lignum, the CH$_2$CI$_2$ fraction was the most potent in inducing QR activity, with a CD value (the concentration required to double the QR activity) of 29.5 $\mu$/mL. The CH$_2$CI$_2$ extract was further separated into six compounds, four of which were identified as 4-methoxydalbergione, latifolin, 4＇,6-dihydroxy-7-methoxyflavanone, and obtusafu-ran. Obtusafuran ［CD ＝ 1.1 $\mu$M； chemopreventive index (CI) ＝ 101.9］ and latifolin (CD ＝ 1.7 $\mu$M； CI ＝ 154.6) displayed potent QR inducing activity and high chemopreventive indices. Lati-folin and 4-methoxydalbergione were identified as strong DPPH-scavengers with half-maximal free radical scavenging concentrations of 15.9 and 17.2 $\mu$M, respectively.

Keywords

References

  1. Chan, S. C., Chang, Y. S., Wang, J. P., Chen, S. C., and Kuo, S. C., Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med., 64,153-158 (1998) https://doi.org/10.1055/s-2006-957394
  2. De Long, M. J., Prochaska, H. J., and Talalay, P., Induction of NAD(P)H:quinone reductase in murine hepatoma cells by phenolic antioxidants, azo dyes, and other chemoprotectors: a model system for the study of anticarcinogens. Proc. Natl. Acad. Sci. U.S.A., 83, 787-791 (1986) https://doi.org/10.1073/pnas.83.3.787
  3. De Long, M. J., Prochaska, H. J., and Talalay, P., Tissuespecific induction patterns of cancer-protective enzymes in mice by tert-butyl-4-hydroxyanisole and related substituted phenols. Cancer Res., 45, 546-551 (1995)
  4. Garhauser, C., You, M., Liu, J., Moriarty, R. M., Hawthorne, M., Metha, R. G., Moon, R. C., and Pezzuto, J. M., Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Cancer Res., 57, 272-278 (1997)
  5. Graham, S., Results of case-control studies of diet and cancer in Buffalo, New York. Cancer Res., 43, 2409s-2413s (1983)
  6. Le Marchand, L., Yoshizawa, C. N., Kolonel, L. N., Hankin, J. H., and Goodman, M. T., Vegetable consumption and lung cancer risk: a population-based case-control study in Hawaii. J. Natl. Caner Inst., 81, 1158-1164 (1989) https://doi.org/10.1093/jnci/81.15.1158
  7. Mehta, R. G. and Pezzuto, J. M., Discovery of cancer preventive agents from natural products: from plants to prevention. Curr. Oncol. Rep., 4, 478-486 (2002) https://doi.org/10.1007/s11912-002-0059-2
  8. Primiano, T., Sutter, T. R., and Kensler, T. W., Redox regulation of genes that protect against carcinogens. Camp. Biochem. Physiol., 118, 487-497 (1997) https://doi.org/10.1016/S0305-0491(97)00221-6
  9. Prochaska, H. J. and Santamaria, A. B., Direct measurement of NAD(P)H:quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal. Biachem., 169, 328-336 (1988) https://doi.org/10.1016/0003-2697(88)90292-8
  10. Prochaska, H. J. and Talalay, P., Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res., 48, 4776-4782 (1988)
  11. Prochaska, H. J. and Talalay, P., The role of NAD(P)H:quinone reductase in protection against the toxicity of quinones and related agents. In Sies, H. (Eds), Oxidative Stress: Oxidants and Antioxidants, Academic Press, London, pp. 195-211, (1991)
  12. Radjendirane, V., Joseph, P., Lee, Y. H., Kimura, S., Klein-Szanto, A. J., Gonzalez, F. J., and Jaiswal, A. K., Disruption of the DT diaphorase (NQO1) gene in mice leads to increased menadione toxicity. J. Biol. Chem., 273, 7382-7389 (1998) https://doi.org/10.1074/jbc.273.13.7382
  13. Ratty, A. K., Sunamoto, J., and Das, N. P., Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical liposomal membranes and soyabean lipoxygenase 1. Biochem. Pharmacol., 37, 989-995 (1998) https://doi.org/10.1016/0006-2952(88)90499-6
  14. Spencer, S. R., Wilczak, C. A., and Talalay, P., Induction of glutathione transferases and NAD(P)H:quinone reductase by fumaric acid derivatives in rodent cells and tissues. Cancer Res., 50, 7871-7875 (1990)
  15. Talalay, P., De Long, M. J., and Prochaska, H. J., Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl. Acad. Sci. U.S.A., 85, 8261-8265 (1988) https://doi.org/10.1073/pnas.85.21.8261
  16. You, W. C., Blot, W. J., Chang, Y. S., Ershow, A, Yang, Z. T, An, Q., Henderson, B. E., Fraumeni Jr., J. F., and Wang, T. G., Allium vegetables and reduced risk of stomach cancer. J. Natl. Cancer Inst., 81, 162-164 (1989) https://doi.org/10.1093/jnci/81.2.162
  17. Yu, S. M., Cheng, Z. J., and Kuo, S. C., Endothelium-dependent relaxation of rat aorta by butein, a novel cyclic AMP-specific phosphodiesterase inhibitor. Eur. J. Pharmacol., 280, 69-77 (1995) https://doi.org/10.1016/0014-2999(95)00190-V
  18. Yu, S. M. and Kuo, S. C., Vasorelaxant effect of isoliquiritigenin, a novel soluble guanylate cyclase activator, in rat aorta. Br. J. Pharmacol., 114, 1587-1594 (1995) https://doi.org/10.1111/j.1476-5381.1995.tb14943.x
  19. Zhang, Y., Kensler, T. W., Cho, C. G., Posner, G. H., and Talalay, P., Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc. Natl. Acad. Sci. U.S.A., 91, 3147-3150 (1994) https://doi.org/10.1073/pnas.91.8.3147