ABSTRACT
A new xanthone compound named retymicin (1) was isolated together with galtamycin B (2) and saquayamycin Z (3), new members of the galtamycin and saquayamycin families, respectively, and the new lumichrome derivative 1-(alpha-ribofuranosyl)-lumichrome (4) from Micromonospora strain Tü 6368, isolated from a soil sample collected in Romania. Retymicin, galtamycin B and saquayamycin Z show cytostatic effects to various human tumor cell lines whereas saquayamycin Z is also active against Gram-positive bacteria.
Subject(s)
Anthracyclines/isolation & purification , Anthracyclines/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Antibiotics, Antineoplastic/isolation & purification , Antibiotics, Antineoplastic/pharmacology , Micromonospora/chemistry , Xanthones/isolation & purification , Bacteria/drug effects , Carbohydrate Sequence , Cell Line, Tumor , Chemical Phenomena , Chemistry, Physical , Chromatography, High Pressure Liquid , Drug Screening Assays, Antitumor , Fermentation , Humans , Microbial Sensitivity Tests , Microscopy, Electron, Scanning , Molecular Sequence Data , Romania , Soil Microbiology , Xanthones/pharmacologyABSTRACT
A detailed screening of the secondary metabolite pattern from Micromonospora sp. strain Tü 6368 resulted in the isolation of ten compounds belonging to five different structural families. The structures of the novel compounds 1-(alpha-ribofuranosyl)-lumichrome (3), retymicin (7), galtamycin B (11) and saquayamycin Z (14) were assigned by spectroscopic methods and chemical transformations. This strain fits our hypothesis that the metabolite analysis of biosynthetically talented strains leads readily to novel compounds.
Subject(s)
Anthracyclines/chemistry , Anthraquinones/chemistry , Anti-Bacterial Agents/chemistry , Antibiotics, Antineoplastic/chemistry , Flavins/chemistry , Micromonospora/chemistry , Monosaccharides/chemistry , Xanthones/chemistry , Carbohydrate Sequence , Magnetic Resonance Spectroscopy , Mass Spectrometry , Molecular Sequence Data , Spectrophotometry, UltravioletABSTRACT
The methanolic extract of the flowering stems of Vitex agnus-castus yielded three new iridoids: 6'-O-foliamenthoylmussaenosidic acid (agnucastoside A), 6'-O-(6,7-dihydrofoliamenthoyl)mussaenosidic acid (agnucastoside B) and 7-O-trans-p-coumaroyl-6'-O-trans-caffeoyl-8-epiloganic acid (agnucastoside C) in addition to four known iridoids (aucubin, agnuside, mussaenosidic acid and 6'-O-p-hydroxybenzoylmussaenosidic acid) and one known phenylbutanone glucoside (myzodendrone). The structure elucidations were mainly done by spectroscopic methods (1D and 2D NMR spectra) and MS data interpretation. The purified compounds were tested for biological activities against various microorganisms and cancer cell lines.
Subject(s)
Glycosides/isolation & purification , Vitex/chemistry , Anti-Infective Agents/chemistry , Anti-Infective Agents/isolation & purification , Anti-Infective Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Bacillus subtilis/drug effects , Candida albicans/drug effects , Escherichia coli/drug effects , Glycosides/chemistry , Glycosides/pharmacology , Humans , Iridoids/chemistry , Magnetic Resonance Spectroscopy , Plant Stems/chemistry , Spectrometry, Mass, Electrospray Ionization , Staphylococcus aureus/drug effects , Tumor Cells, CulturedABSTRACT
The new iridoid glycosides, 4'-deoxykanokoside A and 4'-deoxykanokoside C, were isolated from the methanolic root extract of Centranthus longiflorus ssp. longiflorus. They were accompanied by the three known iridoid glycosides, kanokoside A, kanokoside C and valerosidatum, and two known phenylpropanoid glycosides, coniferin and isoconiferinoside. The structures were elucidated mainly by spectroscopic methods. The presence of 4-deoxy glucose as a part of plant glycosides is rather unusual. Cytotoxic effects of the isolated compounds were also investigated.
