ABSTRACT
One new flavonoid derivative flavoside A (1), one new 5-hydroxyanthranilic acid derivative crassilin (2), along with the known angucyclinone PD116740 (3) and oxachelin (4), was isolated from the EtOAc extract of the fermentation broth of the sea urchin (Anthocidaris crassispina)-derived actinobacterium, Streptomyces sp. HD01. The structures of these compounds were established on the basis of their HR-ESI-MS and NMR spectroscopic data. All of these compounds were assessed for their antibacterial activity.
Subject(s)
Flavonoids/isolation & purification , Flavonoids/pharmacology , Sea Urchins/microbiology , Streptomyces/chemistry , Animals , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Structure , Spectrometry, Mass, Electrospray IonizationABSTRACT
An unusual benzoisoindole-deferoxamine hybrid, streptoxamine (1), has been isolated from the ethyl acetate crude extract of the fermentation broth of a locust-associated actinomycete, Streptomyces sp. HKHCa2, which was isolated from an insect, Oxya chinensis. The structure of this secondary metabolite was elucidated on the basis of its one-dimension, two-dimension NMR, and mass spectroscopic data. This natural product features a hybrid pattern of a benzoisoindole with an "iron carrier" deferoxamine B through C-N linkage. Compound 1 showed weak antibacterial activity against the gram-positive bacteria, Staphylococcus aureus and Mycobacterium smegmatis.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Deferoxamine/isolation & purification , Grasshoppers/microbiology , Indoles/isolation & purification , Streptomyces/chemistry , Animals , Anti-Bacterial Agents/pharmacology , Deferoxamine/pharmacology , Fermentation , Indoles/pharmacology , Microbial Sensitivity Tests , Molecular Structure , Mycobacterium smegmatis/drug effects , Staphylococcus aureus/drug effectsABSTRACT
Four new 5-hydroxyanthranilic acid related compounds, named anthocidins Aâ»D (1â»4), two known analogues n-lauryl 5-hydroxyanthranilate (5) and isolauryl 5-hydroxyanthranilate (6), together with benzamide (7), 3-hydroxy-4-methoxycinnamamide (8), and (3S-cis)-hexahydro-3-[(3,4-dihydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione (9), were isolated from the fermentation broth of the marine-derived actinomycete, Streptomyces sp. HDa1, which was isolated from the gut of a sea urchin, Anthocidaris crassispina, collected from Hainan Island, China. The structures of these secondary metabolites were elucidated on the basis of their 1D and 2D-NMR and mass spectroscopic data, and anthocidin A was confirmed by single-crystal X-ray diffraction with Cu Kα radiation. Anthocidins Aâ»D (1â»4) feature an acetyl group substitution at the amino group and varying alkyl side chains at the carboxyl group of 5-hydroxyanthranilic acid, and compound 5 was isolated as a natural product for the first time. The cytotoxic and antibacterial activity of compounds 1â»9 were evaluated.
Subject(s)
Actinobacteria/pathogenicity , Anti-Bacterial Agents/isolation & purification , Sea Urchins/microbiology , Streptomyces/pathogenicity , ortho-Aminobenzoates/isolation & purification , Actinobacteria/chemistry , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Cell Line, Tumor , Cell Survival , China , Crystallography, X-Ray , Fermentation , Models, Molecular , Molecular Structure , Streptomyces/chemistry , ortho-Aminobenzoates/chemistry , ortho-Aminobenzoates/pharmacologyABSTRACT
Three new γ-butenolide derivatives 1–3, named spiculisporic acids B–D, were isolated from the culture of Aspergillus sp. HDf2, a marine-derived fungus that resides in the sea urchin, Anthocidaris crassispina. The structures of 1–3 were elucidated on the basis of spectroscopic methods, including MS and 2D NMR techniques. Their in vitro cytotoxic activities against two cell lines (SGC-7901, human gastric adenocarcinoma and SPC-A-1, human lung adenocarcinoma) and inhibitory activities against Staphylococcus aureus ATCC 51650 were investigated.