Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I

Zeng, 1996, Nat. Prod. Rep., 13, 275, 10.1039/np9961300275 Alali, 1999, J. Nat. Prod., 62, 504, 10.1021/np980406d Bermejo, 2005, Nat. Prod. Rep., 22, 269, 10.1039/B500186M Lannuzel, 2003, Neuroscience, 121, 287, 10.1016/S0306-4522(03)00441-X Escobar-Khondiker, 2007, J. Neurosci., 27, 7827, 10.1523/JNEUROSCI.1644-07.2007 Takada, 2000, Biochim. Biophys. Acta, 1460, 302, 10.1016/S0005-2728(00)00156-0 Hoppen, 2000, Angew. Chem., Int. Ed., 39, 2099, 10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO;2-Y Torm, 2001, Bioorg. Med. Chem. Lett., 11, 681, 10.1016/S0960-894X(01)00036-1 Torm, 2003, Bioorg. Med. Chem. Lett., 13, 4101, 10.1016/j.bmcl.2003.08.045 Yabunaka, 2003, Bioorg. Med. Chem. Lett., 13, 2385, 10.1016/S0960-894X(03)00439-6 Degli Esposti, 1994, Biochem. J., 301, 161, 10.1042/bj3010161 Miyoshi, 1998, Biochim. Biophys. Acta, 1365, 443, 10.1016/S0005-2728(98)00097-8 Makabe, 2004, Tetrahedron Lett., 45, 973, 10.1016/j.tetlet.2003.11.109 Makabe, 2004, Tetrahedron, 60, 10651, 10.1016/j.tet.2004.09.011 Abe, 2004, Bioorg. Med. Chem. Lett., 14, 779, 10.1016/j.bmcl.2003.11.021 Motoyama, 2002, Bioorg. Med. Chem. Lett., 12, 2089, 10.1016/S0960-894X(02)00374-8 Kuwabara, 2000, Eur. J. Biochem., 267, 2538, 10.1046/j.1432-1327.2000.01263.x Abe, 2005, Biochemistry, 44, 14898, 10.1021/bi051568t Abe, 2008, Biochemistry, 47, 6260, 10.1021/bi800506s Kojima, 2011, Bioorg. Med. Chem. Lett., 21, 5745, 10.1016/j.bmcl.2011.08.011 Kojima, 2009, Molecules, 14, 3621, 10.3390/molecules14093621 Cecil, 2004, J. Org. Chem., 69, 3368, 10.1021/jo049909g Maezaki, 2006, Synlett, 993 Kojima, 2004, Yakugaku Zasshi, 124, 673, 10.1248/yakushi.124.673 Kojima, 2004, Chem. Eur. J., 10, 672, 10.1002/chem.200305459 Kojima, 2003, Chem. Eur. J., 9, 4980, 10.1002/chem.200305185 Maezaki, 2003, Org. Lett., 5, 1411, 10.1021/ol034131r Maezaki, 2002, Org. Lett., 4, 2977, 10.1021/ol026393j Kojima, 2009, Heterocycles, 79, 387, 10.3987/COM-08-S(D)45 Kojima, 2008, Bioorg. Med. Chem. Lett., 18, 6451, 10.1016/j.bmcl.2008.10.069 Kojima, 2008, Bioorg. Med. Chem. Lett., 18, 1637, 10.1016/j.bmcl.2008.01.057 Maezaki, 2007, Heterocycles, 73, 159, 10.3987/COM-07-S(U)1 Tominaga, 2006, Eur. J. Org. Chem., 1422, 10.1002/ejoc.200500850 Maezaki, 2005, Chem. Eur. J., 11, 6237, 10.1002/chem.200500462 Maezaki, 2004, Chem. Commun., 406, 10.1039/b312362f Kojima, 2010, Bioorg. Med. Chem., 18, 8630, 10.1016/j.bmc.2010.10.004 Frantz, 2000, J. Am. Chem. Soc., 122, 1806, 10.1021/ja993838z Müller, 1881, Science, 2007, 317 Hagmann, 2008, J. Med. Chem., 51, 4359, 10.1021/jm800219f Ichimaru, 2005, Biochemistry, 44, 816, 10.1021/bi0479003 Murai, 2006, Biochemistry, 45, 9778, 10.1021/bi060713f Murai, 2007, Biochemistry, 46, 6409, 10.1021/bi7003697 Kakutani, 2010, Biochemistry, 49, 4794, 10.1021/bi100454b Nakanishi, 2011, Biochim. Biophys. Acta, 1807, 1170, 10.1016/j.bbabio.2011.05.012