Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells.

Authors:
Francisco Leon
Francisco Leon
National Institutes of Health
United States
Ignacio Brouard
Ignacio Brouard
University of Pennsylvania
United States
Augusto Rivera
Augusto Rivera
Ciudad Universitaria
Colombia
Fernando Torres
Fernando Torres
University of Texas Southwestern Medical Center
United States
Sara Rubio
Sara Rubio
University of Las Palmas de Gran Canaria
Jose Quintana
Jose Quintana
Hospital Galdakao-Usansolo (Osakidetza)-Red de Investigación en Servicios de Salud en Enfermedades Crónicas
Spain
Francisco Estevez
Francisco Estevez
Juan Canalejo Hospital
Spain
Jaime Bermejo
Jaime Bermejo
Università di Ferrara
Italy

J Med Chem 2006 Sep;49(19):5830-9

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.

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.

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September 2006
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