Beilstein J. Org. Chem.2023,19, 909–917, doi:10.3762/bjoc.19.69
order to scavenge iron from the environment. An example is the thiazoline-containing natural product massiliachelin, which is produced by Massilia sp. NR 4-1 under iron-deficient conditions. Based on experimental evidence and genome analysis, it was suspected that this bacterium synthesizes further iron
biosynthetic intermediates or shunt products of massiliachelin. Their bioactivity was tested against one Gram-positive and three Gram-negative bacteria.
Keywords: Massilia; massiliachelin; siderophore; structure elucidation; Introduction
Iron is crucial for many important biological processes, such as
], the cyclic guanidine alkaloid massinidine [17], and the siderophore massiliachelin [18]. An antiSMASH analysis [19] of the genome of Massilia sp. NR 4-1 revealed the presence of additional biosynthetic gene clusters, including another putative metallophore gene cluster (ACZ75_RS05545–ACZ75_RS06020
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Graphical Abstract
Figure 1:
Selected siderophores from β-proteobacteria.
Beilstein J. Org. Chem.2019,15, 1298–1303, doi:10.3762/bjoc.15.128
product, which was named massiliachelin, corresponds to the assembly line encoded by the identified siderophore locus.
Keywords: agrochelin; genome mining; Massilia; massiliachelin; siderophore; stereochemistry; Introduction
In recent years, chemical investigations as well as genomics led to the
increased in the extract from the iron-deficient culture (Figure 1C). The corresponding metabolite, which is in the following referred to as massiliachelin (1), was subsequently isolated by HPLC.
High-resolution ESIMS of 1 yielded a pseudomolecular ion peak at m/z 467.2033 [M + H]+, which indicates a
S3, Supporting Information File 1).
Conclusion
In summary, Massilia sp. NR 4-1 was found to synthesize an epimer of the alkaloid agrochelin under iron-deficient conditions. The structure of massiliachelin is consistent with the architecture of a biosynthetic assembly line, which is encoded in the
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Graphical Abstract
Figure 1:
A) Organization of the micacocidin-type gene cluster from Massilia sp. NR 4-1 (top) and of the mic ...