A new ceramide from Suillus luteus and its cytotoxic activity against human melanoma cells.
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.
León
Francisco
F
Instituto de Productos Naturales y Agrobiología, CSIC, Instituto Universitario de Bio-Orgánica Antonio González, Av. Astrofísico F. Sánchez 3, E-38206 La Laguna, Tenerife.
Brouard
Ignacio
I
Torres
Fernando
F
Quintana
José
J
Rivera
Augusto
A
Estévez
Francisco
F
Bermejo
Jaime
J
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001487:Basidiomycota / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002518:Ceramides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008545:Melanoma / Q000188:drug therapy*; D008968:Molecular Conformation; D012015:Reference Standards; D013055:Spectrophotometry, Infrared / Q000379:methods; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D002518:Ceramides; D005663:Furans; C527653:N-(5-dodecyl-4-hydroxytetrahydrofuran-3-yl)-2-hydroxyheptadecanamide