Talarazines A–E: Noncytotoxic Iron(III) Chelators from an Australian Mud Dauber Wasp-Associated Fungus, Talaromyces sp. (CMB-W045)

Chemical analysis of an Australian mud dauber wasp-associated fungus, Talaromyces sp. (CMB-W045), yielded five new coprogen siderophores, talarazines A–E (1–5), together with dimerumic acid (6), desferricoprogen (7), and elutherazine B (8). Structures inclusive of absolute configuration were assigne...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-03, Vol.80 (3), p.609-615
Main Authors: Kalansuriya, Pabasara, Quezada, Michelle, Espósito, Breno P, Capon, Robert J
Format: Article
Language:English
Subjects:
Animals
Australia
Chelating Agents
Diketopiperazines - chemistry
Hydroxamic Acids - chemistry
Iron - metabolism
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Siderophores - chemistry
Siderophores - isolation & purification
Talaromyces - chemistry
Wasps - microbiology
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Summary:Chemical analysis of an Australian mud dauber wasp-associated fungus, Talaromyces sp. (CMB-W045), yielded five new coprogen siderophores, talarazines A–E (1–5), together with dimerumic acid (6), desferricoprogen (7), and elutherazine B (8). Structures inclusive of absolute configuration were assigned on the basis of detailed spectroscopic analysis and application of the C3 Marfey’s method. We report on the noncytotoxic Fe­(III) chelation properties of 1–8 and demonstrate that biosynthesis is regulated by available Fe­(III) in culture media. We demonstrate a magnetic nanoparticule approach to extracting high-affinity Fe­(III) binding metabolites (i.e., 8) from complex extracts.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00889