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

Pabasara Kalansuriya; Michelle Quezada; Breno P Espósito; Robert J Capon

doi:10.1021/acs.jnatprod.6b00889

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

J Nat Prod. 2017 Mar 24;80(3):609-615. doi: 10.1021/acs.jnatprod.6b00889. Epub 2017 Jan 6.

Authors

Pabasara Kalansuriya¹, Michelle Quezada¹, Breno P Espósito², Robert J Capon¹

Affiliations

¹ Division of Chemistry and Structural Biology, Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
² Institute of Chemistry, University of São Paulo , São Paulo 05508-000, Brazil.

PMID: 28058837
DOI: 10.1021/acs.jnatprod.6b00889

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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*

Substances

Chelating Agents
Diketopiperazines
Hydroxamic Acids
Siderophores
dimerumic acid
coprogen
Iron
desferricoprogen