Bisbenzyltetrahydroisoquinolines, a new class of inhibitors of the mitochondrial respiratory chain complex I

Planta Medica

Volumn 70, Issue 3, 2004, Pages 266-268

  Granell, Susana ^a   Andreu, Inmaculada ^a   Martí, Daniel ^a   Cavé, Adrién ^b   Aragón, Raúl ^c   Estornell, Ernesto ^a   Cortes, Diego ^a   Zafra Polo, M Carmen ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

^b CENTRE DE BIOCHIMIE STRUCTURALE   (France)

^c UNIVERSIDAD DEL VALLE   (Colombia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; ANTIOQUINE; AROMOLINE; DIBENZYLTETRAHYDROISOQUINOLINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; ISOTETRANDRINE; MEDELLINE; OBAMEGINE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); THALIGRISINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACETYLATION; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; FRUIT; LIPOPHILICITY; MEDICINAL PLANT; MITOCHONDRIAL RESPIRATION; STRUCTURE ACTIVITY RELATION; XYLOPIA COLUMBIANA;

ANIMALS; ANNONACEAE; BENZYLISOQUINOLINES; CATTLE; ELECTRON TRANSPORT; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MITOCHONDRIA, HEART; NADH, NADPH OXIDOREDUCTASES; PHYTOTHERAPY; PLANT EXTRACTS;

MAMMALIA; XYLOPIA;

EID: 1842484263     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-818921     Document Type: Article

References (14)

1. Degli Esposti M. Inhibitors of NADH-ubiquinone reductase: an overview. Biochim Biophys Acta 1998; 1364: 222-35
2. Miyoshi H. Structure-activity relationship of some complex 1 inhibitors. Biochim Biophys Acta 1998; 1364: 236-44
3. Lümmen P. Complex I inhibitors as insecticides and acaricides. Biochim Biophys Acta 1998; 1364: 287-96
4. Cortes D, Sáez J, Hocquemiller R, Cavé Ad, Cavé A. Medelline, first bisbenzylisoquinoline alkaloid with a methylenedioxy bridge. Heterocycles 1986; 24: 607-10
5. Cortes D, Sáez J, Hocquemiller R, Cavé Ad. Alcaloïdes des Annonacées, LIII. Alcaloïdes du Pseudoxandra aff. lucida. Étude de l'antioquine et de ses derivés. J Nat Prod 1985; 48: 76-85
6. Guha KP, Mukherjee B, Mukherjee R. Bisbenzylisoquinoline alkaloids. A review. J Nat Prod 1979; 42: 1-84
7. Schiff PL. Bisbenzylisoquinoline alkaloids. J Nat Prod 1991; 54: 645-749
8. Schiff PL. Bisbenzylisoquinoline alkaloids. J Nat Prod 1983; 46: 1-43
9. Cortes D, Hocquemiller R, Cavé A, Sáez J. Alcaloïdes des Annonacées. Alcaloïdes mineurs des écorces de Pseudoxandra sclerocarpa. J Nat Prod 1986; 49: 854-8
10. Degli Esposti M, Ghelli A, Ratta M, Cortes D, Estornell E. Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (complex I). Biochem J 1994; 301: 161-7
11. Andreu I, Cabedo N, Tormo JR, Bermejo A, Mello R et al. Synthesis of N-diisopropylphosphorylbenzyltetrahydroisoquinoline, a new class of mitochondrial complexes I and III inhibitors. Bioorg Med Chem Lett 2000; 10: 1491-4
12. Hunte C. Insights from the structure of the yeast cytochrome bc1 complex: crystallization of membrane proteins with antibody fragments. FEBS Lett 2001; 504: 126-32
13. Tormo JR, Gallardo T, Aragón R, Cortes D, Estornell E. Specific interactions of monotetrahydrofuranic annonaceous acetogenins as inhibitors of mitochondrial complex I. Chemico-Biol Interact 1999; 122: 171-83
14. Gallardo T, Zafra-Polo MC, Tormo JR, González MC, Franck X et al. Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I. J Med Chem 2000; 43: 4793-800