Heronapyrroles A-C: farnesylated 2-nitropyrroles from an Australian marine-derived Streptomyces sp

Ritesh Raju; Andrew M Piggott; Leticia X Barrientos Diaz; Zeinab Khalil; Robert J Capon

doi:10.1021/ol102162d

Heronapyrroles A-C: farnesylated 2-nitropyrroles from an Australian marine-derived Streptomyces sp

Org Lett. 2010 Nov 19;12(22):5158-61. doi: 10.1021/ol102162d. Epub 2010 Oct 15.

Authors

Ritesh Raju¹, Andrew M Piggott, Leticia X Barrientos Diaz, Zeinab Khalil, Robert J Capon

Affiliation

¹ Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia.

PMID: 20949971
DOI: 10.1021/ol102162d

Abstract

Chemical analysis of a marine-derived Streptomyces sp. (CMB-M0423) isolated from beach sand off Heron Island, Australia, yielded three new members of the rare pyrroloterpene biosynthetic structure class. Identified by detailed spectroscopic analysis as the first reported examples of naturally occurring 2-nitropyrroles, heronapyrroles A-C (1-3) displayed promising biological activity-with low to submicromolar IC(50) activity against Gram-positive bacteria but no cytotoxicity toward mammalian cell lines.

Publication types

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

MeSH terms

Australia
Bacillus subtilis / drug effects
Drug Screening Assays, Antitumor
Escherichia coli / drug effects
Female
Gram-Positive Bacteria / drug effects
HT29 Cells
Humans
Inhibitory Concentration 50
Marine Biology
Microbial Sensitivity Tests
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Prenylation
Pseudomonas aeruginosa / drug effects
Pyrroles / chemistry
Pyrroles / isolation & purification*
Pyrroles / pharmacology
Staphylococcus aureus / drug effects
Streptomyces / chemistry*

Substances

Pyrroles
heronapyrrole A
heronapyrrole B
heronapyrrole C