Online citations, reference lists, and bibliographies.
← Back to Search

Chemoreactive Natural Products That Afford Resistance Against Disparate Antibiotics And Toxins.

Lin Du, J. You, K. Nicholas, R. Cichewicz
Published 2016 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Microorganisms use chemical inactivation strategies to circumvent toxicity caused by many types of antibiotics. Yet in all reported cases, this approach is limited to enzymatically facilitated mechanisms that each target narrow ranges of chemically related scaffolds. The fungus-derived shikimate analogues, pericoxide and pericosine A, were identified as chemoreactive natural products that attenuate the antagonistic effects of several synthetic and naturally derived antifungal agents. Experimental and computational studies suggest that pericoxide and pericosine A readily react via SN 2' mechanisms against a variety of nucleophilic substances under both in vitro aqueous and in situ co-culture conditions. Many of the substitution products from this reaction were highly stable and exhibited diminished toxicities against environmental fungal isolates, including the Tolypocladium sp. strain that produced pericoxide and pericosine A.
This paper references
10.1126/science.1219385
Ecological Populations of Bacteria Act as Socially Cohesive Units of Antibiotic Production and Resistance
O. X. Cordero (2012)
10.1016/S0040-4020(01)87202-1
Cyathiformines A-D, new chorismate-derived metabolites from the fungus Clitocybe cyathiformis
A. Arnone (1993)
10.1021/np800627f
Isolation of 2-pyridone alkaloids from a New Zealand marine-derived penicillium species.
E. D. de Silva (2009)
10.1021/ol100525r
Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors.
D. Boyd (2010)
10.1021/ol9008188
Facile and efficient synthesis of naturally occurring carbasugars (+)-pericosines A and C.
Y. Usami (2009)
10.1098/rsif.2014.0172
Chemical warfare and survival strategies in bacterial range expansions
M. Weber (2014)
10.1038/nrmicro3380
Molecular mechanisms of antibiotic resistance
J. Blair (2015)
Co-treatment of fungi
(2016)
10.1038/ismej.2013.175
Sympatric inhibition and niche differentiation suggest alternative coevolutionary trajectories among Streptomycetes
L. Kinkel (2014)
10.1021/CR9700989
Organic Chemical Reactions in Supercritical Water.
P. Savage (1999)
10.1073/pnas.1318021111
Chemical-biogeographic survey of secondary metabolism in soil
Z. Charlop-Powers (2014)
10.1073/pnas.012399899
Chemical warfare between microbes promotes biodiversity
T. Czárán (2002)
10.1002/9780470988817.CH8
Nucleophilic Additions and Substitutions in Water
D. Sinou (2007)
10.1038/ja.2009.54
Two new members of mycophenolic acid family from Penicillium brevicompactum Dierckx
X. Lu (2009)
10.1021/cr800448q
Organic synthesis "on water".
Arani Chanda (2009)
10.1038/ismej.2014.106
Improved annotation of antibiotic resistance determinants reveals microbial resistomes cluster by ecology
Molly K. Gibson (2015)
10.1002/anie.201306549
Crowdsourcing natural products discovery to access uncharted dimensions of fungal metabolite diversity.
Lin Du (2014)
10.1073/pnas.1504076112
Socially mediated induction and suppression of antibiosis during bacterial coexistence
Monica I. Abrudan (2015)
10.3389/fmicb.2013.00145
Novel resistance functions uncovered using functional metagenomic investigations of resistance reservoirs
Erica C. Pehrsson (2013)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar