Journal of Natural Products · 2016 · 22 citations · 6 references
Life SciencesBiochemistryChemistryBioorganic ChemistryMycologyOrganic ChemistryFungal BiochemistryFungal Secondary MetabolitesAbsolute Configuration AssignmentAbsolute Configuration DeterminationFungal Bioactive CompoundsStructure Elucidation Of Fungal MetabolitesTime-dependent Density Functional TheoryX-ray Spectral Analysis
Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher's method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively.
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J. A. Barltrop, Terence C. Owen, Ann H. Cory et al. · Bioorganic & Medicinal Chemistry Letters · 1991 · 451 citations