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

Francisco León, Ignacio Brouard, Augusto Rivera, Fernando Torres, Sara Rubio, José Quintana, Francisco Estévez, Jaime Bermejo

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)5830-5839
Number of pages10
JournalJournal of Medicinal Chemistry
Volume49
Issue number19
DOIs
Publication statusPublished - Sep 21 2006

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells'. Together they form a unique fingerprint.

Cite this