New teleocidin metabolites from Streptoverticillium blastmyceticum.

Agricultural and Biological Chemistry
1985.0

Abstract

Teleocidins are known to be potent skin tumor promoters and Epstein-Barr virus early antigen (EBV-EA) inducers. We recently found a strain, Streptoverticillium blastmyceticum NA34-17, which produces EBV-EA-inducing indole alkaloids and is currently the only microorganism known to produce (-)-indolactam V, a structural fragment common to teleocidins. In a previous paper, we reported the occurrence of teleocidin B-4 and olivoretins in the mycelia of this strain. We examined the cultured broth and isolated new teleocidin-related compounds 3 and 4. This paper deals with their isolation and structure. Compound 3 was identified as N-acetyl-L-tryptophanol (molecular formula C13H16N2O2) by spectral data and is believed to be an important precursor of (-)-indolactam V. Compound 4 was deduced to be (-)-2-oxy-indolactam V (molecular formula C17H23N3O3) from spectral data. (-)-2-Oxyindolactam V did not show EBV-EA induction. Comparing (-)-2-oxy-indolactam V with 2-oxy-LSD suggests that similar detoxifying pathways for LSD may be available for teleocidin-related compounds. The metabolism of (-)-indolactam V is now being investigated using liver microsomes.

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