New method for the determination of the absolute stereochemistry in antitumoral annonaceous acetogenins

6533b7ddfe1ef96bd1275132

RESEARCH PRODUCT

New method for the determination of the absolute stereochemistry in antitumoral annonaceous acetogenins

Catherine Lavaud M. Carmen Zafra-polo Teresa Gallardo Diego Cortes M. Carmen González

subject

Rollinia membranacea Chemistry Stereochemistry Organic Chemistry Membranacin Diastereomer Rollimembrin Biochemistry chemistry.chemical_compound Drug Discovery Acetogenin Annonaceous Acetogenins Desacetyluvaricin Mitochondrial Complex I

description

Abstract The absolute configurations at the carbinol centers in several acetogenins were determined through p-bromophenylurethane derivatives and subsequent Mosher ester methodology. This method has been applied on α,α′-dihydroxylated adjacent bis-THF acetogenins with a threo/cis/threo/cis/erythro relative configuration membrarollin (1), a new acetogenin isolated from Rollinia membranacea seeds, rollimembrin (2), membranacin (3) and rolliniastatin-1 (4), and a threo/trans/threo/translerythro relative configuration motrilin (5), squamocin (6), and desacetyluvaricin (7). 1 was found to be the most potent inhibitor of the mammalian mitochondrial complex I.

year	journal	country	edition	language
1998-05-01	Tetrahedron

https://doi.org/10.1016/s0040-4020(98)00301-9

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