Avenolide, a Streptomyces hormone controlling antibiotic production in Streptomyces avermitilis

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Abstract

Gram-positive bacteria of the genus Streptomyces are industrially important microorganisms, producing >70% of commercially important antibiotics. The production of these compounds is often regulated by low-molecular-weight bacterial hormones called autoregulators. Although 60% of Streptomyces strains may use γ-butyrolactone-type molecules as autoregulators and some use furan- type molecules, little is known about the signaling molecules used to regulate antibiotic production in many other members of this genus. Here, we purified a signaling molecule (avenolide) from Streptomyces avermitilis - the producer of the important anthelmintic agent avermectin with annual world sales of $850 million - and determined its structure, including stereochemistry, by spectroscopic analysis and chemical synthesis as (4S,10R)-10-hydroxy-10- methyl-9-oxo-dodec-2-en-1,4-olide, a class of Streptomyces autoregulator. Avenolide is essential for eliciting avermectin production and is effective at nanomolar concentrations with a minimum effective concentration of 4 nM. The aco gene of S. avermitilis, which encodes an acyl-CoA oxidase, is required for avenolide biosynthesis, and homologs are also present in Streptomyces fradiae, Streptomyces ghanaensis, and Streptomyces griseoauranticus, suggesting that butenolide-type autoregulators may represent a widespread and another class of Streptomyces autoregulator involved in regulating antibiotic production.

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CITATION STYLE

APA

Kitani, S., Miyamoto, K. T., Takamatsu, S., Herawati, E., Iguchi, H., Nishitomi, K., … Nihira, T. (2011). Avenolide, a Streptomyces hormone controlling antibiotic production in Streptomyces avermitilis. Proceedings of the National Academy of Sciences of the United States of America, 108(39), 16410–16415. https://doi.org/10.1073/pnas.1113908108

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