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

Schmid, Julian C.; Frey, Kerstin; Scheiner, Matthias; Garzón, Jaime Felipe Guerrero; Stafforst, Luise; Fricke, Jan-Niklas; Schuppe, Michaela; Schiewe, Hajo; Zeeck, Axel; Weber, Tilmann; Usón, Isabel; Kemkemer, Ralf; Decker, Michael; Grond, Stephanie

doi:10.1002/anie.202106802

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/persons/resource/persons75667

Kemkemer, Ralf
Cellular Biophysics, Max Planck Institute for Medical Research, Max Planck Society;

External Resource

https://onlinelibrary.wiley.com/doi/10.1002/anie.202106802
(Any fulltext)

https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fanie.202106802&file=anie202106802-sup-0001-JCSchmid_Collazulen.cif
(Supplementary material)

https://onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fanie.202106802&file=anie202106802-sup-0001-misc_information.pdf
(Supplementary material)

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

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.

Cite as: https://hdl.handle.net/21.11116/0000-0010-0A80-2

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.