Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 35, Pages 10278-10282Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604126
Keywords
antimicrobial activity; combined; cultures; natural products; structure elucidation; total synthesis
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Funding
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science, and Technology of Japan (MEXT)
- Japan Agency for Medical Research and Development (AMED)
- Institute for Fermentation, Osaka (IFO)
- Grants-in-Aid for Scientific Research [25702048, 16K18673, 15K14721] Funding Source: KAKEN
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A series of lipidic spirohemiaminals, designated streptoaminals, is reported. These were discovered by surveying the unique molecular signatures identified in the mass spectrometry data of the combined-culture broth of Streptomyces nigrescens HEK616 and Tsukamurella pulmonis TP-B0596. Mass spectrometry analysis showed that streptoaminals appeared as a cluster of ion peaks, which were separated by 14 mass unit intervals, implying the presence of alkyl chains of different lengths. The chemical structures of these compounds were elucidated by spectroscopic analysis and total synthesis. Streptoaminals with globular structures showed broad antimicrobial activities, whereas the planar structures of the 5-alkyl-1,2,3,4-tetrahydroquinolines found in the same combined-culture did not. This work shows the application of microbes as reservoirs for a range of chemical scaffolds.
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