ABSTRACT
Boshramycinones A-C (1-3), three new anthracyclinones, were isolated from the culture broth of the marine-derived Streptomyces sp. Mei 16-1,2 together with 2-acetyl-1,8-dihydroxy-3-methyl-anthraquinone (4) and bafilomycins B1, B2, and C1-amide. The isolated compounds were identified by NMR spectroscopy and mass spectrometry, the absolute configuration of 3 was determined by comparison of experimental and ab initio-calculated chiroptical data. The antimicrobial activity of the bacterial extract and the isolated compounds were assayed using a set of microorganisms, and cytotoxic activities were determined against 36 human cancer cell lines.
Subject(s)
Anthraquinones/chemistry , Anthraquinones/pharmacology , Anti-Infective Agents/pharmacology , Antineoplastic Agents/pharmacology , Streptomyces/metabolism , Anthraquinones/metabolism , Anti-Infective Agents/chemistry , Antineoplastic Agents/chemistry , Aquatic Organisms , Cell Line, Tumor , Drug Evaluation, Preclinical , Humans , Macrolides/chemistry , Macrolides/metabolism , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Structure , Streptomyces/chemistryABSTRACT
Chemical screening of the ethyl acetate extract from the marine-derived Streptomyces sp. isolate Mei37 resulted in five isoquinolinequinones, four new derivatives, mansouramycin A-D (1, 3-5), and the known 3-methyl-7-(methylamino)-5,8-isoquinolinedione (2). Their structures were elucidated by NMR and MS techniques and by comparison with related compounds. Cytotoxicity profiling of the mansouramycins in a panel of up to 36 tumor cell lines indicated significant cytotoxicity of several derivatives, with pronounced selectivity for non-small cell lung cancer, breast cancer, melanoma, and prostate cancer cells.
Subject(s)
Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Isoquinolines/isolation & purification , Isoquinolines/pharmacology , Antineoplastic Agents/chemistry , Drug Screening Assays, Antitumor , Female , Humans , Isoquinolines/chemistry , Male , Marine Biology , Microbial Sensitivity Tests , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Streptomyces/chemistryABSTRACT
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
During the last 10 years marine organisms have provided a large number of new natural products. Interesting compounds have mainly been derived from macroorganisms such as sponges, ascidians, corals and bryozoans. The number of secondary metabolites from marine microorganisms is smaller, but rapidly increasing. Because of the enormous difficulties involved in harvesting products from marine animals, and the fact that some of the bioactive compounds are produced by associated bacteria, the advantages of sustainable production of bioactive metabolites by bacteria or fungi, under the protection of natural resources, seem to be very attractive for the future. This review describes current progress in the isolation and identification of novel marine microorganisms, the discovery of new secondary metabolites, the biotechnological approaches to overproduce them, as well as the evaluation and characterization of their bioactivity.
