Essential structural factors of annonaceous acetogenins as potent inhibitors of mitochondrial complex I

Biochimica et Biophysica Acta - Bioenergetics

Volumn 1365, Issue 3, 1998, Pages 443-452

  Miyoshi, Hideto ^a   Ohshima, Michiyo ^a   Shimada, Hiroko ^b   Akagi, Toshio ^c   Iwamura, Hajime ^a   McLaughlin, Jerry L ^b  

^a KYOTO UNIVERSITY   (Japan)

^b PURDUE UNIVERSITY   (United States)

^c ISHIHARA SANGYO KAISHA LTD   (Japan)

Author keywords

Acetogenin; NADH ubiquinone oxidoreductase; Structure activity relationship

Indexed keywords

ACETOGENIN; ANTIMYCIN A1; MITOCHONDRIAL COMPLEX I; UBIQUINOL CYTOCHROME C REDUCTASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; COW; DRUG CONFORMATION; ELECTRON TRANSPORT; ENZYME INHIBITION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATTLE; ENZYME INHIBITORS; FURANS; KINETICS; LACTONES; MITOCHONDRIA, HEART; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAD(P)H DEHYDROGENASE (QUINONE); PLANTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE;

EID: 0032551770     PISSN: 00052728     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0005-2728(98)00097-8     Document Type: Article

References (33)

1. [1] L. Zeng, Q. Ye, N.H. Oberlies, G. Shi, Z.-M. Gu, K. He, J.L. McLaughlin, Nat. Prod. Rep. 13 (1996) 275-306.
2. [2] Z.-M. Gu, G.-X. Zhao, N.H. Oberlies, J.L. McLaughlin in: J.T. Arnason, R. Mata, J.T. Romeo (Eds.), Recent Advances in Phytochemistry, Vol. 29, Plenum Press, New York, 1995, pp. 249-310.
3. [3] X.-P. Fang, M.J. Rieser, Z.-M. Gu, G.-X. Zhao, J.L. McLaughlin, Phytochem. Anal. 4 (1993) 27-67.
4. [4] J.L. McLaughlin, L. Zeng, N.H. Oberlies, D. Alfonso, H.A. Johnson, B.A. Cummings, in: P.A. Hedin, R.M. Hollingworth, E.P. Masler, J. Miyamoto, D.G. Thompson (Eds.), ACS Symposium Series, Phytochemicals for Pest Control, 658, American Chemical Society, Washington, DC, 1997, pp. 117-133.
5. [5] N.H. Oberlies, C.-J. Chang, J.L. McLaughlin, J. Med. Chem. 40 (1997) 2102-2106.
6. [6] M. Degli Esposti, A. Ghelli, M. Ratta, D. Cortes, E. Estornell, Biochem. J. 301 (1994) 161-167.
7. [7] R.M. Hollingworth, K.I. Ahammadsahib, G. Gadelhak, J.L. McLaughlin, Biochem. Soc. Trans. 22 (1994) 230-233.
8. [8] M.C. Gonzalez, J.R. Tormo, A. Bermejo, M.C. Zafra-Polo, E. Estornell, D. Cortes, Bioorg. Med. Chem. Lett. 7 (1997) 1113-1118.
9. [9] T. Friedrich, P. Van Heek, H. Leif, T. Ohnishi, E. Forche, B. Kunze, R. Jansen, W. Trowitzsch-Kienast, G. Höfle, H. Reichenbach, H. Weiss, Eur. J. Biochem. 219 (1994) 691-698.
10. [10] J.L. Landolt, K.I. Ahammadsahib, R.M. Hollingworth, F.L. Barr, N.L. Crane, N.L. Buerck, G.P. McCabe, J.L. McLaughlin, Chemico-Biol. Interact. 98 (1995) 1-13.
11. [11] E. Estornell, J.R. Tormo, D. Cortes, Biochem. Biophys. Res. Commun. 240 (1997) 234-238.
12. [12] D. Alfonso, H.A. Johnson, T. Colman-Saizarbitoria, C.P. Presley, G.P. McCabe, J.L. McLaughlin, Nat. Toxins 4 (1996) 181-188.
13. [13] H. Naito, E. Kawahara, K. Maruta, M. Maeda, S. Sasaki, J. Org. Chem. 60 (1995) 4419-4427.
14. [14] S.C. Sinha, A. Sinha, A. Yazbak, Z. Keinan, J. Org. Chem. 61 (1996) 7640-7641.
15. [15] J.A. Marshall, K.W. Hinkle, J. Org. Chem. 62 (1997) 5989-5995.
16. [16] J.A. Marshall, M. Chen, J. Org. Chem. 62 (1997) 5996-6000.
17. [17] H. Miyoshi, M. Inoue, S. Okamoto, M. Ohshima, K. Sakamoto, H. Iwamura, J. Biol. Chem. 272 (1997) 16176-16183.
18. [18] A. Matsuno-Yagi, Y. Hatefi, J. Biol. Chem. 260 (1985) 14424-14427.
19. [19] T. Akagi, Y. Takahashi, S. Sasaki, Quant. Struct.-Act. Relat. 15 (1996) 290-295.
20. [20] Y. Takahashi, T. Akagi, S. Sasaki, Tetrahedron Computer Methodology 3 (1990) 27-35.
21. [21] H. Shimada, J.B. Grutzner, J.F. Kozlowski, J.L. McLaughlin, Biochemistry 37 (1998) 854-866.
22. [22] N. Tokutake, H. Miyoshi, H. Nakazato, H. Iwamura, Biochim. Biophys. Acta 1142 (1993) 262-268.
23. [23] K.H. Chung, K.Y. Cho, Y. Asami, N. Takahashi, S. Yoshida, Z. Naturforsch. 44c (1989) 609-616.
24. [24] N. Tokutake, H. Miyoshi, T. Satoh, T. Hatano, H. Iwamura, Biochim. Biophys. Acta 1185 (1994) 271-278.
25. [25] H. Miyoshi, N. Tokutake, Y. Imaeda, T. Akagi, H. Iwamura, Biochim. Biophys. Acta 1229 (1995) 149-154.
26. [26] D.J. Horgan, H. Ohno, T.P. Singer, J.E. Casida, J. Biol. Chem. 243 (1968) 5967-5976.
27. [27] G. Thierbach, B. Kunze, H. Reichenbach, G. Höfle, Biochim. Biophys. Acta 765 (1984) 227-235.
28. [28] M. Degli Esposti, A. Ghelli, Biochim. Biophys. Acta 1187 (1994) 116-120.
29. [29] U. Brandt, Biochim. Biophys. Acta 1318 (1997) 79-81.
30. [30] K. He, L. Zeng, Q. Ye, G. Shi, N.H. Oberlies, G.-X. Zhao, J. Njoku, J.L. McLaughlin, Pestic. Sci. 49 (1997) 372-378.
31. [31] J. Morré, R. DeCabo, C. Farley, N.H. Oberlies, J.L. McLaughlin, Life Sci. 56 (1995) 343-348.
32. [32] S.M. Simon, M. Schindler, Proc. Natl. Acad. Sci. USA 91 (1994) 3497-3504.
33. [33] V. Ling, Cancer Res. 69 (1992) 2603-2609.