ABSTRACT
Two novel cyclopeptides with special skeleton, namely, dolyemycins A (1) and B (2) were isolated from Streptomyces griseus subsp. griseus HYS31 by bio-guided isolation. Their structures were elucidated by detailed analysis of spectroscopic data. These two compounds were cyclopeptides containing eleven amino acids including five unusual amino acids (hydroxyglycine, 3-hydroxyleucine, 3-phenylserine, ß-hydroxy-O-methyltyrosine, 2,3-diaminobutyric acid) in both of them and an extra nonprotein amino acids (3-methylaspartic acid) in Dolyemycin B only. Dolyemycins A and B performed antiproliferative activity against human lung cancer A549 cells with IC50 values of 1.0 and 1.2 µM, respectively.
Subject(s)
Peptides, Cyclic/chemistry , Streptomyces griseus/chemistry , A549 Cells , Amino Acid Sequence , Antineoplastic Agents/chemistry , Antineoplastic Agents/metabolism , Antineoplastic Agents/pharmacology , Humans , Models, Molecular , Peptides, Cyclic/metabolism , Peptides, Cyclic/pharmacology , Protein Conformation , Streptomyces griseus/metabolismABSTRACT
Two novel γ-butyrolactones ghanamycins A (1) and B (2) were isolated from the fermentation broth of marine-derived Streptomyces ghanaensis TXC6-16. Their structures were elucidated by spectroscopic analysis. These two novel compounds exhibited antimicrobial activities against some phytopathogens. The minimum IC (MIC) of 2 against Pseudomonas syringae and Erwinia sp. were 50 µg ml-1.
Subject(s)
4-Butyrolactone/analogs & derivatives , 4-Butyrolactone/isolation & purification , Anti-Infective Agents/isolation & purification , Streptomyces/metabolism , 4-Butyrolactone/chemistry , 4-Butyrolactone/pharmacology , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Erwinia/drug effects , Fermentation , Microbial Sensitivity Tests , Pseudomonas syringae/drug effects , Spectrum AnalysisABSTRACT
This research was aimed at establishing the pilot-scale purification technology of lipopeptide from marine-derived Bacillus marinus. We studied lipopeptide surfactivity interferences on scale-up unit technologies including acid precipitation, methanol extraction, solvent precipitation, salting out, extraction, silica gel column chromatography and HZ806 macroporous absorption resin column chromatography. Then, the unit technologies were combined in a certain order, to remove the impurities gradually, and to gain purified lipopeptide finally, with high recovery rate throughout the whole process. The novel pilot-scale purification technology could effectively isolate and purify lipopeptide with 87.51% to 100% purity in hectograms from 1 ton of Bacillus marinus B-9987 fermentation broth with more than 81.73% recovery rate. The first practical hectogram production of highly purified lipopeptide derived from Bacillus marinus was achieved. With this new purification method, using complex media became possible in fermentation process to reduce the fermentation cost and scale-up the purification for lipopeptide production. For practicability and economy, foaming problem resulting from massive water evaporation was avoided in this technology.
Subject(s)
Bacillus/chemistry , Industrial Microbiology , Lipopeptides/isolation & purification , Chromatography , Fermentation , Seawater/microbiology , SolventsABSTRACT
Fradcarbazoles A-C (1-3), three new indolocarbazoles, were isolated from a mutant strain of the marine-derived actinomycete Streptomyces fradiae 007M135. Their structures were established by spectroscopic analysis, quantum chemical calculation, CD spectra, and chemical transformation. Fradcarbazole A (1) possessed a unique skeleton consisting of a staurosporine core, a thiazole ring, and an indole fragment. Compounds 1-3 displayed significant cytotoxicity against HL-60, K562, A-549, and BEL-7402 cell lines and inhibitory effects on the kinase PKC-α with IC(50) values of 0.001-4.58 µM.
