Methylenolactocin, a novel antitumor antibiotic from Penicillium sp.

Abstract

A novel antitumor antibiotic, methylenolactocin, was isolated from the culture nitrate of a new isolate of fungus identified as Penicillium sp. The fermentation yield reached about 100 mg per liter of the broth. Methylenolactocin has the molecular formula of CnHi6O4 and possess an exomethylene lactone structure. Its structure was determined to be 3-carboxy-2-methylene-4-nonanolide by spectroscopic data. It is active against some Gram-positive bacteria and it prolongs the life span of mice inoculated with Ehrlich carcinoma.

Catalytic, asymmetric reactions of ketenes and ketene enolates

“…Analogously, γ-lactones have been employed as novel antibacterial and antitumor agents 125. This structural unit frequently occurs in natural products including classes of alkaloids,126 macrocyclic antibiotics,127 and pheromones 128.…”

The Orthoester Johnson–Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates – Recent Advances

“…In a stereodivergent approach using both diastereomeric lactones obtained from Johnson-Claisen rearrangement of an acetonide-containing allyl alcohol, Fernandes [155] later disclosed the total syntheses of (-)-methylenolactocin (275, Scheme 52) [152] and (-)-phaseolinic acid (276). [156] The hydroxy alkynoate 271, obtained from hexanal, was transformed into allyl alcohol 272.…”

Recent advances in the discovery and development of stilbenes and lactones in anticancer therapy

“…Methylenolactocin shows antitumour activity against Ehrlich carcinoma in mice and prolongs the lifespan of the treated mice bearing tumour cells [68]. Another type of lactone, aliphatic acid, which is called C75, inhibits mammalian fatty acid synthase and inhibits fatty acid synthesis in human cancer cells and normal liver cells [69].…”