Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 108, Issue 39, Pages 16410-16415Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.1113908108
Keywords
structure elucidation; actinomycetes; intercellular communications; microbial hormones
Categories
Funding
- Noda Institute for Scientific Research
- Japan Society for the Promotion of Science (JSPS)
- National Research Council of Thailand
- National Science and Technology Development Agency of Thailand
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- Institute for Fermentation, Osaka
- Grants-in-Aid for Scientific Research [21360404, 22108006] Funding Source: KAKEN
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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.-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-10methyl-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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