Producción Científica Profesorado

Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circulardichroism



Torres Valencia, J. Jesús Martín

2011

Velázquez-Jiménez R, Torres-Valencia JM, Cerda-García-Rojas CM, Hernández-Hernández JD, Román-Marín LU, Manríquez-Torres JJ, Gómez-Hurtado MA, Valdez-Calderón A, Motilva V, García-Mauriño S, Talero E, Avila J, Joseph-Nathan P. Absolute configuration of podophyllotoxin related lignans from Bursera fagaroides using vibrational circulardichroism, Año: 2011, Volume: 72 Issue: 17 Pages: 2237-2243 DOI: 10.1016/j.phytochem.2011.07.017 ISSN: 0031-9422


Abstract


The ethanol extract from the dried exudate of Bursera fagaroides (Burseraceae) showed significant cytotoxicactivity in the HT-29 (human colon adenocarcinoma) test system. The extract provided four podophyllotoxin relatedlignans, identified as (7'R,8R,8'R)-(-)-deoxypodophyllotoxin (3), (7'R,8R,8'R)-(-)-morelensin (4), (8R,8'R)-(-)-yatein (5),and (8R,8'R)-(-)-5'-desmethoxyyatein (6), whose spectroscopic and chiroptical properties were compared with those of(7R,7'R,8R,8'R)-(-)-podophyllotoxin (1) and its acetyl derivative (2). Their absolute configurations were assigned bycomparison of the vibrational circular dichroism spectra of I and 3 with those obtained by density functional theorycalculations.



Producto de Investigación




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