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  The structure of cyclodecatriene collinolactone, its biosynthesis, and semisynthetic analogues: effects of monoastral phenotype and protection from intracellular oxidative stress

Schmid, J. C., Frey, K., Scheiner, M., Garzón, J. F. G., Stafforst, L., Fricke, J.-N., et al. (2021). The structure of cyclodecatriene collinolactone, its biosynthesis, and semisynthetic analogues: effects of monoastral phenotype and protection from intracellular oxidative stress. Angewandte Chemie International Edition, 60(43), 23212-23216. doi:10.1002/anie.202106802.

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Item Permalink: https://hdl.handle.net/21.11116/0000-0010-0A80-2 Version Permalink: https://hdl.handle.net/21.11116/0000-0010-0A81-1
Genre: Journal Article

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 Creators:
Schmid, Julian C., Author
Frey, Kerstin, Author
Scheiner, Matthias, Author
Garzón, Jaime Felipe Guerrero, Author
Stafforst, Luise, Author
Fricke, Jan-Niklas, Author
Schuppe, Michaela, Author
Schiewe, Hajo, Author
Zeeck, Axel, Author
Weber, Tilmann, Author
Usón, Isabel, Author
Kemkemer, Ralf1, Author           
Decker, Michael, Author
Grond, Stephanie, Author
Affiliations:
1Cellular Biophysics, Max Planck Institute for Medical Research, Max Planck Society, ou_2364731              

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Free keywords: Alzheimer's disease; biosynthesis; natural products; neuroprotection; polyketide
 Abstract: Recently described rhizolutin and collinolactone isolated from Streptomyces Gö 40/10 share the same novel carbon scaffold. Analyses by NMR and X-Ray crystallography verify the structure of collinolactone and propose a revision of rhizolutin's stereochemistry. Isotope-labeled precursor feeding shows that collinolactone is biosynthesized via type I polyketide synthase with Baeyer-Villiger oxidation. CRISPR-based genetic strategies led to the identification of the biosynthetic gene cluster and a high-production strain. Chemical semisyntheses yielded collinolactone analogues with inhibitory effects on L929 cell line. Fluorescence microscopy revealed that only particular analogues induce monopolar spindles impairing cell division in mitosis. Inspired by the Alzheimer-protective activity of rhizolutin, we investigated the neuroprotective effects of collinolactone and its analogues on glutamate-sensitive cells (HT22) and indeed, natural collinolactone displays distinct neuroprotection from intracellular oxidative stress.

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Language(s): eng - English
 Dates: 2021-07-092021-05-202021-08-202021-09-212021-10-18
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: URI: https://pubmed.ncbi.nlm.nih.gov/34415670/
DOI: 10.1002/anie.202106802
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (43) Sequence Number: - Start / End Page: 23212 - 23216 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851