Enantiospecific semisynthesis of (+)-almuheptolide-A, a novel natural heptolide inhibitor of the mammalian mitochondrial respiratory chain

Journal of Medicinal Chemistry

Volumn 41, Issue 26, 1998, Pages 5158-5166

  Bermejo, Almudena ^a   Torino, José R ^a   Cabedo, Nuria ^a   Estornell, Ernesto ^b   Figadère, Bruno ^a   Cortes, Diego ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; ALMUHEPTOLIDE A; ETHARVENSIN; GONIOTHALENOL; HEPTOLIDE INHIBITOR; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHIRALITY; CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; MAMMAL; MITOCHONDRIAL RESPIRATION; PLANT;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CATTLE; ELECTRON TRANSPORT; ELECTRON TRANSPORT COMPLEX I; ENZYME INHIBITORS; KINETICS; MITOCHONDRIA, HEART; MODELS, MOLECULAR; NADH, NADPH OXIDOREDUCTASES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0032542392     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9706574     Document Type: Article

References (36)

1. Zafra-Polo, M. C.; Figadère, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Natural acetogenins from Annonaceae, synthesis and mechanisms of action. Phytochemlstry 1998, 48, 1087-1117.
2. Cave, A.; Figadère, B.; Laurens, A.; Cortes, D. Acetogenins from Annonaceae. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag; New York, 1997; pp 81288.
3. Gonzalez, M. C.; Tormo, J. R.; Bermejo, A.; Zafra-Polo, M. C.; Estornell, E.; Cortes, D. Rollimembrin, a novel acetogenin inhibitor of mammalian mitochondrial complex I. Bioorg. Med. Chem. Lett. 1997, 7, 1113-1118.
4. Zafra-Polo, M. C.; Gonzalez, M. C.; Tormo, J. R.; Estornell, E.; Cortes, D. Polyalthidin: new prenylated benzopyran inhibitor of the mammalian mitochondrial respiratory chain. J. Nat. Prod. 1996, 59, 913-916.
5. Bermejo, A.; Lora, M. J.; Blazquez, M. A.; Rao, K. S.; Cortes, D.; Zafra-Polo, M. C. (H-)-Goniotharvensin, a novel styryl-lactone from the stem bark of Goniothalamus ari-ensis. Nat. Prod. Lett. 1995, 7, 117-122.
6. Bermejo, A.; Blazquez, M. A.; Serrano, A.; Zafra-Polo, M. C.; Cortes, D. Preparation of 7-alkoxylated furano-pyrone skeletons: Semisynthesis of (-)-etharvensin, a new styryl-lactone from Goniothalamus arvensis. J. Nat. Prod. 1997, 60, 13381340.
7. Bermejo, A.; Blazquez, M. A.; Rao, K S.; Cortes, D. Styrylpyrones from Goniothalamus arvensis. Phytochemistry 1998,47, 1375-1380.
8. Fang, X. P.; Anderson, J. E.; Qiu, X. X.; Kozlowski, J. F.; Chang, C. J.; McLaughlin, J. L. Gonioheptolides-A and -B: novel eightmembered-ring lactoncs from Goniothalamus giganteus (Annonaceae). Tetrahedron 1993, 49, 1563-1570.
9. Tapiolas, D. M.; Roman, M.; Fenical, W.; Stout, T. J.; Clardy, J. Octalactins-A and -B: cytotoxic eight-membered-ring lactones from a marine bacterium, Streptomyces sp. J. Am. Chem. Soc. 1991, 113, 4682-4683.
10. Miyoshi, H.; Tokutake, N.; Imaeda, Y.; Akagi, T.; Iwamura, H. A model of antimycin A binding based on structure-activity studies of synthetic antimycin A analogues. Biochim. Biophys. Acta 1995, 1229, 149-154.
11. Ramsay, R. R.; Salach, J. I.; Dadgar, J.; Singer, T. P. Inhibition of mitochondria! NADH dehydrogenase by pyridine derivatives and its possible relatiorfto experimental and idiopathic parkinsonism. Biochem. Biophys. Res. Commun. 1986,135, 269-275.
12. Degli Esposti, M.; Ghelli, A.; Ratta, M.; Cortes, D.; Estornell, E. Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondria! NADH dehydrogenase (Complex I). Biochem. J. 1994, 307, 161-167.
13. Oberlies, N. H.; Croy, V. L.; Harrison, M. L.; McLaughlin, J. L. The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. Cancer Lett. 1997, 115, 73-79.
14. Hollingworth, R. M.; Ahammadsahib, K. L; Gadelhak, G.; "McLaughlin, J. L. New inhibitors of complex I of the mitochondrial electron transport chain with activity as pesticides. Biochem. Soc. Trans 1994, 22, 230-233.
15. Andrus, M. B.; Argade, A. B. Synthesis of octalactin lactone and side chain. Tetrahedron Lett. 1996, 37, 5049-5052.
16. Kodama, M.; Matsushita, M.; Terada, Y.; Takeuchi, A.; Yoshio, S.; Fukuyama, Y. Enantioselective synthesis of octalactin-A. Chem. Lett. 1997, 117-118.
17. McNaughton-Smith, G. A.; Taylor, R. J. H. The preparation of 9-substituted A5-octenolides: synthesis of 8-deoxy-pseudo-ascidiatrienolide-C. Tetrahedron 1996, 52, 2113-2124.
18. Doyle, M. P.; Protopopova, M. N. Macrocyclic lactones from dirhodium (ID-catalyzed intramolecular cyclopropanation and carbon-hydrogen insertion. J. Am. Chem. Soc. 1995,117,72817282.
19. Miyoshi, H.; Inoue, M.; Okamoto, S.; Ohshima, M.; Sakamoto, K.; Iwamura, H. Probing the ubiquinone reduction site of mitochondria! complex I using novel cationic inhibitors. J. Biol. Chem. 1997, 272, 16176-16183.
20. Gluck, M. R.; Krueger, M. J.; Ramsay, R. R.; Sablin, S. O.; Singer, T. P.; Nicklas, W. J. Characterization of the inhibitory mechanism of l-methyl-4-phenyIpyridinium and 4-phenylpyridine analogues in inner membrane preparations. J. Biol. Chem. 1994, 269, 3167-3174.
21. Friedrich, T.; Van Heck, P.; Leif, H.; Ohnishi, T.; Forche, E.; Kunze, B.; Jansen, R.; Trowitzsch-Kienast, W.; Höfle, G.; Reichenbach, H.; Weiss, H. Two binding sites of inhibitors in NADH: ubiquinone oxidoreductase (complex I). Relationship of one site with the ubiquinone-binding site of bacterial glucose: ubiquinone oxidoreductase. Eur. J. Biochem. 1994, 279, 691-698.
22. Singer, T. P.; Ramsay, R. R. The reaction sites of rotenone and ubiquinone with mitochondrial NADH dehydrogenase. Biochim. Biophys. Acta 1994, 1187, 198-202.
23. Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Ghelli, A.; Ratta, M.; Benelli, B.; Degli Esposti, M. Thienylimidazo[2,l-b]thiazoles as inhibitors of mitochondrial NADH dehydrogenase. J. Med. Chem. 1995, 38, 1090-1097.
24. Fato, R.; Estornell, E.; Di Bernardo, S.; Pallotti, F.; ParentiCastelli, G.; Lenaz, G. Steady-state kinetics of the reduction of coenzyme Q analogues by complex I (NADH:ubiquinone oxidoreductase) in bovine heart mitochondria and submitochondrial particles. Biochemistry 1996, 35, 2705-2716.
25. Degli Esposti, M. Inhibitors of NADH-ubiquinone reductase: an overview. Biochim. Biophys. Acta 1998, 7364, 222-235.
26. Brandt, U. Proton-translocation by membrane-bound NADH: ubiquinone-oxidoreductase (complex I) through redox-gated ligand conduction. Biochim. Biophys. Ada 1997, 1318, 79-91.
27. Degli Esposti, M.; Ghelli, A. The mechanism of proton and electron transport in mitochondrial complex I. Biochim. Biophys. Acta 1994, 1187, 116-120.
28. Estornell, E.; Tormo, J. R.; Cortes, D. Cherimolin-1, new selective inhibitor of the first energy-coupling site of the NADH: ubiquinone oxidoreductase (complex I). Biochem. Biophys. Res. Commun. 1997,240, 234-238.
29. Cornelissen, J.; Van Kuilenburg, A. B. P.; Voûte, P. A.; Van Gennip, A. H. The effect of the neuroblastoma-seeking agent meta-iodobenzylguanidine (MIGB) on NADH-driven Superoxide formation and NADH-driven lipid peroxidation in beef heart submitochondrial particles. Eur. J. Cancer 1997, 33, 421-424.
30. Turrens, J. F.; Boveris, A. Generation of Superoxide anion by the NADH dehydrogenase of bovine heart mitochondria. Biochem. J. 1980, 797, 421-427.
31. Degli Esposti, M.; Ngo, A.; Ghelli, A.; Benelli, B.; Carelli, V.; McLennan, H.; Linnane, A. W. The interaction of Q analogues, particularly hydroxydecyl benzoquinone (idebenone), with the respiratory complexes of heart mitochondria. Arch. Biochem. Biophys. 1996, 330, 395-400.
32. Turrens, J. F. Superoxide production by the mitochondrial respiratory chain. Biosci. Rep. 1997, 17, 3-8.
33. Oberlies, N. H.; Chang, C.; McLaughlin, J. R. Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. J. Med. Chem. 1997, 40, 2102-2106.
34. Estornell, E.; Fato, R.; Pallotti, F.; Lenaz, G. Assay conditions for the mitochondrial NADH: coenzyme Q oxidoreductase. FEBS Lett. 1993, 332, 127-131.
35. Estornell, E.; Fato, R.; Catelluccio, C.; Cavazzoni, M.; ParentiCastelli, G.; Lenaz, G. Saturation kinetics of coenzyme Q in NADH and succinate oxidation in beef heart mitochondria. FEBS Lett. 1992,311, 107-109.
36. Estornell, E.; Tormo, J. R.; Barber, T. A deficiency in respiratory complex I in heart mitochondria from vitamin A-deficient rats is counteracted by an increase in coenzyme Q. Biochem. Biophys. Res. Commun. 1997, 233, 451-454.