Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 9, 2006, Pages 3119-3130

  Makabe, Hidefumi ^a   Kimura, Yuka ^a   Higuchi, Masaharu ^a   Konno, Hiroyuki ^b   Murai, Masatoshi ^c   Miyoshi, Hideto ^c  

^a SHINSHU UNIVERSITY   (Japan)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Annonaceous acetogenin; Antitumor; Mitochondrial complex I; Stereoselective synthesis

Indexed keywords

BENZETHONIUM CHLORIDE; BULLATACIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; ROLLICOSIN; SQUAMOSTOLIDE; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HEART MITOCHONDRION; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKYNES; ANIMALS; CATTLE; ELECTRON TRANSPORT COMPLEX I; ENZYME INHIBITORS; FURANS; ISOMERISM; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MITOCHONDRIA, HEART; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

BOVINAE;

EID: 33644974479     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.12.015     Document Type: Article

References (32)

1. For recent reviews for Annonaceous acetogenins, see: A. Bermejo, B. Figadère, M.-C. Zafra-Polo, I. Barrachina, E. Estornell, and D. Cortes Nat. Prod. Rep. 22 2005 269 303
2. C.-C. Liaw, F.-R. Chang, M.-J. Wu, and Y.-C. Wu J. Nat. Prod. 66 2003 279 281
3. H.H. Xie, X.Y. Wei, J.D. Wang, M.F. Liu, and R.Z. Yang Chin. Chem. Lett. 14 2003 588 590
4. S.H. Myint, A. Laurens, R. Hocquemiller, A. Cavé, D. Davoust, and D. Cortes Heterocycles 31 1990 861 867
5. M.H. Woo, Q. Ye, Z.-M. Gu, G.-X. Zhao, and J.L. McLaughlin Bioorg. Med. Chem. Lett. 5 1995 1135 1140
6. S.H. Myint, D. Cortes, A. Laurens, R. Hocquemiller, M. Leboeuf, A. Cavé, J. Cotte, and A.-M. Quero Phytochemistry 30 1991 3335 3338
7. C. Gleye, P. Duret, A. Laurens, R. Hocquemiller, and A. Cavé J. Nat. Prod. 61 1998 576 579
8. For isolation: M.J. Rieser, J.F. Kozlowski, K.V. Wood, and J.L. McLaughlin Tetrahedron Lett. 32 1991 1137 1140 For synthesis:
9. E. Keinan, S. Sinha, S.B. Anjana, Z.M. Wang, X.L. Zhang, and K.B. Sharpless Tetrahedron Lett. 33 1992 6307 6410
10. H. Makabe, A. Tanaka, and T. Oritani Biosci. Biotechnol. Biochem. 57 1993 1028 1029
11. For preliminary communication of the synthesis of (4R,15R,16R,21S)- rollicosin (1), (4R,15S,16S,21S)-rollicosin (2) and their inhibitory action of mitochondrial complex I: H. Makabe, M. Higuchi, H. Konno, M. Murai, and H. Miyoshi Tetrahedron Lett. 46 2005 4671 4675
12. K.J. Quinn, A.K. Isaacs, B.A. DeChristopher, S.C. Szklarz, and R.A. Arvary Org. Lett. 7 2005 1243 1245
13. J.-L. Lee, C.-F. Lin, L.-Y. Hsieh, H.-F. Chiu, Y.-C. Wu, K.-S. Wang, and M.-J. Wu Tetrahedron Lett. 44 2003 7833 7835
14. C.-L. Lee, C.-F. Lin, W.-R. Lin, K.-S. Wang, Y. Chang, S.-R. Lin, Y.-C. Wu, and M.-J. Wu Bioorg. Med. Chem. 13 2005 5864 5872
15. J.D. White, T.C. Somers, and G.N. Reddy J. Org. Chem. 57 1992 4991 4998
16. K.B. Sharpless, W. Amberg, Y.L. Bennani, G.A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu, and X.-L. Zhang J. Org. Chem. 57 1992 2768 2771
17. H. Becker, and K.B. Sharpless Angew. Chem. Int. Ed. 35 1996 448 451
18. T.-S. Hu, Q. Yu, Y.-L. Wu, and Y. Wu J. Org. Chem. 66 2001 853 861
19. W.-Q. Yang, and T. Kitahara Tetrahedron Lett. 40 1999 7827 7830
20. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 1975 4467 4470
21. H. Makabe, A. Miyawaki, R. Takahashi, Y. Hattori, H. Konno, M. Abe, and H. Miyoshi Tetrahedron Lett. 45 2004 973 977
22. 13C NMR of 1 synthesized by us matched very well with those by K. J. Quinn and coworkers.
23. The discrepancy in the optical rotation value of the synthetic product with that reported for the natural product has been reported S.C. Sinha, S.C. Sinha, and E. Keinan J. Org. Chem. 64 1999 7067 7073
24. S. Takahashi, A. Kubota, and T. Nakata Org. Lett. 5 2003 1353 1356
25. Ref. 17.
26. 3) δ: 19.12, 21.17, 25.41, 25.55, 28.70, 29.41, 29.47, 31.98, 33.41, 33.46, 37.43, 69.99, 71.49, 77.98, 82.82, 131.23, 151.81, 174.59, 177.38.
27. D.W. Hart, and J. Schwartz J. Am. Chem. Soc. 96 1974 8115 8116
28. H. Miyoshi, M. Ohshima, H. Shimada, T. Akagi, H. Iwamura, and J.L. McLaughlin Biochim. Biophys. Acta 1365 1998 443 452
29. M. Abe, M. Murai, N. Ichimaru, A. Kenmochi, T. Yoshida, A. Kubo, Y. Kimura, A. Moroda, H. Makabe, T. Nishioka, and H. Miyoshi Biochemistry 44 2005 14898 14906
30. H. Makabe, Y. Hattori, Y. Kimura, H. Konno, M. Abe, H. Miyoshi, A. Tanaka, and T. Oritani Tetrahedron 60 2004 10651 10657
31. T. Motoyama, H. Yabunaka, and H. Miyoshi Bioorg. Med. Chem. Lett. 12 2002 2089 2092
32. A. Matsuno-Yagi, and Y. Hatefi J. Biol. Chem. 260 1985 14424 14427