title: Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells.
abstract: Two new long-chain ceramides, trametenamides A (1) and B (2), were isolated from the methanolic extract of the fruiting body of the fungus Trametes menziesii. The structures were elucidated by spectroscopic analyses and chemical transformations, and the absolute stereochemistry of trametenamide B (2) was determined by stereoselective total synthesis of four possible diastereomers. The acetyl derivative of the natural ceramide (1a) and synthetic ceramides (24-27) showed cytotoxicity on the human melanoma cell line SK-MEL-1, which was caused by induction of apoptosis as determined by DNA fragmentation, poly(ADP-ribose) polymerase cleavage, and procaspase-9 and -8 processing.
authors.affiliation: Instituto de Productos Naturales y Agrobiología, C.S.I.C., Instituto Universitario de Bio-Organica Antonio Gonzalez, Avda. Astrofísico F. Sanchez 3, 38206 La Laguna, Tenerife, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: León
authors.forename: Ignacio
authors.initials: I
authors.lastname: Brouard
authors.forename: Augusto
authors.initials: A
authors.lastname: Rivera
authors.forename: Fernando
authors.initials: F
authors.lastname: Torres
authors.forename: Sara
authors.initials: S
authors.lastname: Rubio
authors.forename: José
authors.initials: J
authors.lastname: Quintana
authors.forename: Francisco
authors.initials: F
authors.lastname: Estévez
authors.forename: Jaime
authors.initials: J
authors.lastname: Bermejo
mesh_terms: D045744:Cell Line, Tumor; D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008545:Melanoma; D011124:Polyporaceae / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002518:Ceramides; C514174:trametenamide A; C514173:trametenamide B