Cytotoxic grifolin derivatives isolated from the wild mushroom Boletus pseudocalopus (Basidiomycetes).
Activity-guided purification of a MeOH extract of the Korean wild mushroom Boletus pseudocalopus afforded three new grifolin derivatives, 1-3, along with four known phenolic compounds 4-7. Their structures were established by a combination of 1H- and 13C-NMR, NOESY, and extensive two-dimensional NMR spectroscopic experiments such as gCOSY, gHSQC, gHMBC, and ROESY. The major metabolites 4 and 5 were subjected to reduction to provide the side chain-reduced compounds 8 and 9 for biological testing. All of the compounds except compound 6 showed anticancer activities in the range of IC(50) 3.5-11.0 microg/ml against human lung carcinoma A549 and mouse melanoma B16F1 cell lines. In addition, all compounds showed moderate radical-scavenging activities determined by DPPH assay.
Song
Junsik
J
Department of Chemistry, Kongju National University, Kongju 314-701, Republic of Korea.
Manir
Md Maniruzzaman
MM
Moon
Surk-Sik
SS
D000363:Agaricales / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D001487:Basidiomycota / Q000737:chemistry*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D013559:Symbiosis; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity
C546096:(2R*,4R*)-3,4-dihydro-4,5-dimethyl-8-((2E,6E)-3,7,11-trimethyldodec-2,6,10-trienyl-2H-(1)benzopyran-2,7-diol); C546095:4-(1-ethoxyethyl)-5-methyl-2-((2E,6E)-3,7,11-trimethyldodec-2,6,10-trienyl)benzene-1,3-diol; C546094:4-(1-methoxyethyl)-5-methyl-2-((2E,6E)-3,7,11-trimethyldodec-2,6,10-trienyl)benzene-1,3-diol; D000970:Antineoplastic Agents; D013729:Terpenes; C058858:grifolin