A Novel Neuronal Cell Protecting Substance, Naphthomycinol, Produced byStreptomyces sp. PF7.

The Journal of Antibiotics
1996.0

Abstract

The neuronal degeneration which results from cerebral ischemia is thought to be due to an overexcretion of the excitatory amino acid, L-glutamic acid, which acts as a neurotransmitter in the major part of brain. Brain ischemia injury maybe expected to be overcome by L-glutamate toxicity suppressors. In the course of our screening for substances that protect neuronal hybridoma N18-RE-105 cells from L-glutamate toxicity, we isolated carquinostatin A, lavanduquinocin, aestivophoenins A and B, and 4-demethoxymichigazone. Further investigation has resulted in the isolation of a novel neuronal cell protecting substance, naphthomycinol (1). We report herein the fermentation, isolation and structure determination of 1. The naphthomycinol producing organism, identified as Streptomyces sp. PF7, was cultivated in a 50-liter jar fermenter under specific conditions. The mycelial acetone extract was processed through solvent extraction and various chromatographic methods to purify 1. The molecular formula of 1 was established as C40H49NO9 by high-resolution FAB-MS. The 1H and 13C NMR spectral data indicate that the structure of 1 is very similar to those of naphthomycins except for the presence of an additional oxymethine. Naphthomycinol, a member of the naphthomycins series, is the first compound which has a hydroxyl function at C-ll so far reported. In the evaluation system we employed, 1 decreased the L-glutamate toxicity in N18-RE-105 cells with EC50 value 400 nM. Since the L-glutamate toxicity in N18-RE-105 cells was thought to be caused by glutathione depletion, we assessed buthionine sulfoximine (BSO) toxicity which directly inhibits gliutathione synthesis. Antioxidants such as vitamin E suppress both the L-glutamate and the BSO toxicities in N18-RE-105 cells. Naphthomycinol, however, did not suppress the BSO toxicity. This result strongly suggests that the mode of action of naphthomycinol is not based on the antioxidative activity.

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