TY  - JOUR
U1  - Zeitschriftenartikel, wissenschaftlich - begutachtet (reviewed)
A1  - Kemkemer, Ralf
A1  - Schmid, Julian
A1  - Frey, Kerstin
A1  - Schreiner, Matthias
A1  - Guerrero Garzón, Jaime Felipe
A1  - Stafforst, Luise
A1  - Fricke, Jan-Niklas
A1  - Schuppe, Michaela
A1  - Schiewe, Hajo
A1  - Zeeck, Axel
A1  - Weber, Tilmann
A1  - Usón, Isabel
A1  - Decker, Michael
A1  - Grond, Stephanie
T1  - The structure of cyclodecatriene collinolactone, its biosynthesis, and semisynthetic analogues: Effects of monoastral phenotype and protection from intracellular oxidative stress
JF  - Angewandte Chemie : a journal of the Gesellschaft Deutscher Chemiker. International edition
N2  - Recently described rhizolutin and collinolactone isolated from Streptomyces Gç 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 rhizolutins 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 Alzheimerprotective 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.
Y1  - 2021
UN  - https://nbn-resolving.org/urn:nbn:de:bsz:rt2-opus4-33439
SN  - 1433-7851
SS  - 1433-7851
U6  - https://doi.org/10.1002/anie.202106802
DO  - https://doi.org/10.1002/anie.202106802
VL  - 60
IS  - 43
SP  - 23212
EP  - 23216
S1  - 5
PB  - Wiley
CY  - Weinheim
ER  -