Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1

• Main Authors: Jan Diettrich, Hirokazu Kage, Markus Nett
• Format: Article
• Language: English
• Published: Beilstein-Institut 2019-06-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: agrochelin; genome mining; Massilia; massiliachelin; siderophore; stereochemistry
• Online Access: https://doi.org/10.3762/bjoc.15.128

A putative siderophore locus was detected in the genome of the violacein-producing bacterium Massilia sp. NR 4-1 and predicted to direct the biosynthesis of a molecule that is structurally related to the thiazoline-containing siderophore micacocidin. In order to track this compound, we analyzed the metabolic profiles of Massilia cultures grown under different iron concentrations. A compound which was found to be predominantly produced under iron deficiency was subsequently isolated. Its structural characterization by spectroscopic and bioinformatic analyses revealed a previously not known diastereomer of the cytotoxic alkaloid agrochelin. The structure of this natural product, which was named massiliachelin, corresponds to the assembly line encoded by the identified siderophore locus.