ABSTRACT
New nine insecticidal antibiotics designated yaequinolones were isolated from the culture broth of the fungal strain Penicillium sp. FKI-2140 by solvent extraction, centrifugal partition chromatography and HPLC. Yaequinolones showed growth inhibitory activity against brine shrimp (Artemia salina). Among them, yaequinolone F has the most potent activity with MIC value of 0.19 microg/ml.
Subject(s)
Insecticides/metabolism , Insecticides/pharmacology , Penicillium/classification , Penicillium/metabolism , Quinolones/metabolism , Quinolones/pharmacology , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/metabolism , Anti-Bacterial Agents/pharmacology , Artemia/drug effects , Fermentation , Insecticides/isolation & purification , Larva/drug effects , Microbial Sensitivity Tests , Quinolones/classification , Quinolones/isolation & purification , Spores, Fungal/ultrastructureABSTRACT
The structure and relative stereochemistry of yaequinolones, fungal insecticidal antibiotics, were elucidated by spectroscopic studies, including NMR spectral analyses. Yaequinolones possess a p-methoxyphenylquinolinone skeleton modified with different isoprenyl-derived side chains.
Subject(s)
Insecticides/chemistry , Penicillium/classification , Penicillium/metabolism , Quinolones/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/metabolism , Insecticides/metabolism , Penicillium/chemistry , Quinolones/metabolismABSTRACT
[chemical reaction: see text]. Two novel insecticidal antibiotics with a p-methoxyphenylquinolinone skeleton fused with a pyran ring, yaequinolones J1 (1) and J2 (2), have been isolated from Penicillium sp. FKI-2140, and structures were elucidated by spectroscopic studies including various NMR experiments. The relative stereochemistries were assigned by NOE experiments. Yaequinolones J1 and J2 showed toxicity against Artemia salina (brine shrimp) with the MIC value of 6.25 microg/mL.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Artemia/drug effects , Insecticides/isolation & purification , Penicillium/chemistry , Pyrans/isolation & purification , Quinolones/isolation & purification , Animals , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Insecticides/chemistry , Insecticides/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Pyrans/chemistry , Pyrans/pharmacology , Quinolones/chemistry , Quinolones/pharmacologyABSTRACT
Four new antibiotics, sesquicillins B to E were isolated from the culture broth of Albophoma sp. FKI-1778 together with known sesquicillin (sesquicillin A in this paper). The structures of sesquicillins were elucidated by spectroscopic studies including various NMR experiments. All sesquicillins have a common pyrano-diterpene skeleton. Sesquicillins showed moderate inhibitory activity against the growth of Artemia salina (brine shrimps) and Jurkat cells.
Subject(s)
Anti-Bacterial Agents/pharmacology , Fungi/metabolism , Insecticides/pharmacology , Naphthalenes/pharmacology , Animals , Anti-Bacterial Agents/biosynthesis , Artemia , Cell Survival/drug effects , Chemical Phenomena , Chemistry, Physical , Chromatography, High Pressure Liquid , Culture Media , Drug Screening Assays, Antitumor , Fermentation , Fungi/chemistry , Humans , Insecta , Insecticides/metabolism , Jurkat Cells , Magnetic Resonance Spectroscopy , Molecular Conformation , Naphthalenes/metabolismABSTRACT
New insecticidal antibiotics designated hydroxyfungerins A and B were isolated from the culture broth of a fungal strain Metarhizium sp. FKI-1079 together with a known compound, fungerin. The structures of hydroxyfungerins A and B were elucidated by spectroscopic studies including various NMR experiments. Hydroxyfungerins A and B showed growth inhibitory activity against brine shrimps, Artemia salina.
