Inhibitors of DNA polymerase β from Schoepfia californica

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Jie Chen, Yu-Huan Zhang, Li-Kai Wang, Steven J. Sucheck, Angela M. Snow and Sidney M. Hecht


Abstract

Fractionation of a hexane extract prepared from the plant Schoepfiacalifornica was carried out by bioassay guided fractionation, affording five inhibitors of DNA polymerase β; four of these were shown to be anacardic acid and structurally related derivatives, while the fifth was oleic acid.


References

  1. See, e.g. T. S.-F. Wang, Annu. Rev. Biochem., 1991, 60, 513 Search PubMed; Y. Matsumoto and K. Kim, Science, 1995, 269, 699 CrossRef CAS; A. Sancar, Annu. Rev. Biochem., 1996, 65, 43 CAS.
  2. B. N. Ames, M. K. Shigenaga and T. M. Hagen, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 7915 CAS.
  3. M. R. Miller and D. N. Chinault, J. Biol. Chem., 1982, 257, 10204 CAS.
  4. J. A. DiGiuseppe and S. L. Dresler, Biochemistry, 1989, 28, 9515 CrossRef CAS.
  5. R. K. Singhal, R. Prasad and S. H. Wilson, J. Biol. Chem., 1995, 270, 949 CrossRef CAS.
  6. S. Seki and T. Oda, Carcinogensis, 1988, 9, 2239 Search PubMed.
  7. A. J. Fornace, Jr., B. Zmudzka, M. C. Hollander and S. H. Wilson, Mol. Cell. Biol., 1989, 9, 851 CAS.
  8. J.-S. Hoffmann, M.-J. Pillaire, G. Maga, V. Podust, U. Hübscher and G. Villani, Proc. Natl. Acad. Sci. U.S.A., 1995, 92, 5356 CAS.
  9. Polymerase β inhibitors of moderate potency have been reported, although none has been used to potentiate the action of DNA damaging antitumor agents. See K. Ono, H. Nakane and M. Fukushima, Eur. J. Biochem., 1988, 172, 349 Search PubMed; Y. Mizushina, H. Yagi, N. Tanaka, T. Kurosawa, H. Seto, K. Katsumi, M. Onoue, H. Ishida, A. Iseki, T. Nara, K. Morohashi, T. Horie, Y. Onomura, M. Narusawa, N. Aoyagi, K. Takami, M. Yamaoka, Y. Inoue, A. Matsukage, S. Yoshida and K. Sakaguchi, J. Antibiot., 1996, 49, 491 CrossRef CAS; H.-D. Sun, S.-X. Qiu, L.-Z. Lin, Z.-Y. Wang, Z.-W. Lin, T. Pengsuparp, J. M. Pezzuto, H. H. S. Fong, G. A. Cordell and N. R. Farnsworth, J. Nat. Prod., 1996, 59, 525 CAS; H. Ishiyama, M. Ishibashi, A. Ogawa, S. Yoshida and J. Kobayashi, J. Org. Chem., 1997, 62, 3831 CrossRef CAS; N. Tanaka, A. Kitamura, Y. Mizushina, F. Sugawa and K. Sakaguchi, J. Nat. Prod., 1998, 61, 193 CrossRef CAS.
  10. T. Date, M. Yamaguchi, F. Hirose, Y. Nishimoto, K. Tanihara and A. Matsukage, Biochemistry, 1988, 27, 2983 CrossRef CAS.
  11. S. G. Widen, P. Kedar and S. H. Wilson, J. Biol. Chem., 1988, 263, 16992 CAS.
  12. A. M. Snow, Ph.D. Thesis, University of Virginia, 1995.
  13. J. G. Batchelor, R. J. Cushley and J. H. Prestegard, J. Org. Chem., 1974, 39, 1698 CrossRef CAS.
  14. H. Itokawa, N. Totsuka, K. Nakahara, K. Takeya, J.-P. Lepoittevin and Y. L. Asakawa, Chem. Pharm. Bull., 1987, 35, 3016 CAS.
  15. D. F. Ewig, Org. Magn. Reson., 1979, 12, 499 Search PubMed.
  16. See, e.g. F. D. Gustone, M. R. Pollard, C. M. Scrimgeour and H. S. Vedanayagam, Chem. Phys. Lipids, 1977, 18, 115 Search PubMed; J. W. deHaan and L. J. M. de Ven, Org. Magn. Reson., 1979, 5, 147 CrossRef CAS; R. Rossi, A. Carpita, M. G. Quirici and C. A. Varacini, Tetrahedron, 1982, 38, 639 Search PubMed.
  17. See, e.g. J. R. Barr, R. T. Scannell and K. Yamaguchi, J. Org. Chem., 1989, 54, 494 Search PubMed.
  18. F. M. Hauser and S. A. Pogany, Synthesis, 1980, 814 CrossRef CAS.
  19. E. J. Corey, J.-L. Gras and P. Ulrich, Tetrahedron Lett., 1976, 11, 809 CrossRef.
  20. P. L. Creger, J. Am. Chem. Soc., 1970, 92, 1396 CrossRef CAS; The bromide itself was accessible from the corresponding commercially available alcohol by treatment with Ph3PBr2(P. E. Sonner, Synth. Commun., 1976, 6, 21) Search PubMed.
  21. See, e.g. Y. Yamagiwa, K. Ohashi, Y. Sakamoto, S. Hirakawa, T. Kamikawa and I. Kubo, Tetrahedron, 1987, 43, 3387 Search PubMed; R. Zehnter and H. Gerlach, Liebigs Ann., 1995, 2209 CrossRef CAS.
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