A new ceramide from Suillus luteus and its cytotoxic activity against human melanoma cells.

Abstract

A new phytosphingosine-type ceramide, suillumide (1), was isolated from the EtOH extract of the basidiomycete Suillus luteus (L.) S. F. Gray, along with ten known compounds: ergosta-4,6,8(14),22-tetraen-3-one, ergosterol, ergosterol peroxide, suillin, (E)-3,4,5-trimethoxycinnamic alcohol, 5 alpha,6 alpha-epoxyergosta-8,22-diene-3beta,7 beta-diol, (R)-1-palmitoylglycerol, ergosta-7,9(11),22-triene-3beta,5 alpha,6 beta-triol, cerevisterol, and 4-hydroxybenzoic acid. The structure of 1 was determined on the basis of spectroscopic and mass-spectrometric analyses, as well as by chemical methods. Compound 1 and its synthetic diacetyl derivative 2 were tested for their cytotoxic activities against the human melanoma cell line SK-MEL-1. Both drugs showed IC(50) values of ca. 10 microM after 72 h of exposure.

• Authors: Francisco León, Ignacio Brouard, Fernando Torres, José Quintana, Augusto Rivera, Francisco Estévez, Jaime Bermejo
• Journal: Chemistry & biodiversity (Chem Biodivers) Vol. 5 Issue 1 Pg. 120-5 (Jan 2008) ISSN: 1612-1880 [Electronic] Switzerland
• PMID: 18205114 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents
• Ceramides
• Furans
• N-(5-dodecyl-4-hydroxytetrahydrofuran-3-yl)-2-hydroxyheptadecanamide

Topics

• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Basidiomycota (chemistry)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Ceramides (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Furans (chemistry, isolation & purification, pharmacology)
• Humans
• Magnetic Resonance Spectroscopy (methods, standards)
• Melanoma (drug therapy)
• Molecular Conformation
• Reference Standards
• Spectrophotometry, Infrared (methods)
• Stereoisomerism
• Structure-Activity Relationship