ABSTRACT
From Penicillium janczewskii, obtained from a marine sample, two new diastereomeric quinolinones, 3S,4R-dihydroxy-4-(4'-methoxyphenyl)-3,4-dihydro-2(1H)-quinolinone (1) and 3R,4R-dihydroxy-4-(4'-methoxyphenyl)-3,4-dihydro-2(1H)-quinolinone (2), were identified, along with two known alkaloids, peniprequinolone (3) and 3-methoxy-4-hydroxy-4-(4'-methoxyphenyl)-3,4-dihydro-2(1H)-quinolinone (4). Cytotoxicity testing on eight tumor cell lines revealed a moderate specificity of 2 on SKOV-3 cells.
Subject(s)
Alkaloids/isolation & purification , Antineoplastic Agents/isolation & purification , Penicillium/chemistry , Quinolones/isolation & purification , Alkaloids/chemistry , Alkaloids/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Humans , Marine Biology , Molecular Structure , North Sea , Quinolones/chemistry , Quinolones/pharmacology , Stereoisomerism , Tumor Cells, CulturedABSTRACT
A strain of Penicillium brevicompactum derived from a specimen of the Mediterranean sponge Petrosia ficiformis was investigated for its secondary metabolites. Using fast centrifugal partitioning chromatography (FCPC) two previously unknown cyclodepsipeptides, petrosifungins A (1) and B (2), were isolated, both containing two neighboring units of the nonproteinogenic amino acid l-pipecolinic acid. The absolute configurations of all amino acids were established to be l using GITC derivatization and Marfey's method. Furthermore, the known metabolite brevianamide A (3) was isolated. The likewise known compounds mycophenolic acid (4) and asperphenamate (5) were identified from their spectroscopic properties directly in the extract using HPLC-UV, -MS, and -NMR coupling.
Subject(s)
Depsipeptides , Penicillium/chemistry , Peptides, Cyclic/isolation & purification , Phenylalanine/analogs & derivatives , Alkaloids/chemistry , Alkaloids/isolation & purification , Animals , Chromatography, High Pressure Liquid , Mediterranean Sea , Molecular Structure , Mycophenolic Acid/chemistry , Mycophenolic Acid/isolation & purification , Nuclear Magnetic Resonance, Biomolecular , Peptides, Cyclic/chemistry , Phenylalanine/chemistry , Phenylalanine/isolation & purification , Piperazines/chemistry , Piperazines/isolation & purification , Porifera , Spiro Compounds/chemistry , Spiro Compounds/isolation & purificationABSTRACT
The ethyl acetate extract of Penicillium sp., derived from the Mediterranean sponge Axinella verrucosa, yielded the known compound communesin B (1) and its new congeners communesins C (2) and D (3), as well as the known compounds griseofulvin, dechlorogriseofulvin, and oxaline. All structures were unambiguously established by 1D and 2D NMR and MS data. In several bioassays performed on different leukemia cell lines, the communesins exhibited moderate antiproliferative activity.
Subject(s)
Antineoplastic Agents/isolation & purification , Heterocyclic Compounds, 4 or More Rings/isolation & purification , Penicillium/chemistry , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Artemia/drug effects , Drug Screening Assays, Antitumor , Griseofulvin/isolation & purification , Heterocyclic Compounds, 4 or More Rings/chemistry , Heterocyclic Compounds, 4 or More Rings/pharmacology , Humans , Italy , Mediterranean Sea , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Porifera , Stereoisomerism , Tumor Cells, CulturedABSTRACT
From a strain of the fungus Emericella variecolor derived from the marine sponge Haliclona valliculata, two new natural products, evariquinone and isoemericellin, were isolated after HPLC-UV, -MS, and -NMR studies of the extract and their structures were elucidated by mass spectrometry and NMR experiments. Evariquinone showed antiproliferative activity towards KB and NCI-H460 cells at a concentration of 3.16 microg/ml. Furthermore, the fungus was found to produce the known metabolites stromemycin, shamixanthone, and 7-hydroxyemodin. Chemical degradation, NMR decoupling experiments, and spin-system simulation provided evidence for the double bonds in stromemycin to be all E-configured. ROESY experiments established the monosaccharide moiety to be glucose.
Subject(s)
Benzoquinones/isolation & purification , Benzyl Alcohols/isolation & purification , Emericella/chemistry , Animals , Antibiotics, Antineoplastic/chemistry , Antibiotics, Antineoplastic/isolation & purification , Antibiotics, Antineoplastic/pharmacology , Benzoquinones/chemistry , Benzoquinones/pharmacology , Benzyl Alcohols/chemistry , Benzyl Alcohols/pharmacology , Drug Screening Assays, Antitumor , Emericella/metabolism , Humans , Isomerism , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Porifera/microbiology , Tumor Cells, CulturedABSTRACT
Fungal isolates of Penicillium cf. montanense were obtained from the marine sponge Xestospongia exiguacollected from the Bali Sea, Indonesia. Culture filtrates of the fungi yielded three novel decalactone metabolites, xestodecalactones A, B, and C (1, 2a, and 2b), consisting of 10-membered macrolides with a fused 1,3-dihydroxybenzene ring. Online HPLC-NMR, ESI-MS/MS, and -CD spectra were acquired, and the structures of the new compounds were established and confirmed on the basis of offline NMR spectroscopic ((1)H, (13)C, COSY, ROESY, (1)H-detected direct and long-range (13)C-(1)H correlations) and mass spectrometric (EIMS) data. Quantum chemical calculations of the CD spectra proved to be difficult because of the conformational flexibility of the xestodecalactones. These compounds, of which 2a and 2b, due to the additional stereocenter at C-9, are diastereomeric compounds, are structurally related to a number of biologically active metabolites found in terrestrial fungal strains. Compound 2a was found to be active against the yeast Candida albicans.
