Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium

Noel M. Lacerna; Bailey W. Miller; Albebson L. Lim; Jortan O. Tun; Jose Miguel D. Robes; Mark Jeremiah B. Cleofas; Zhenjian Lin; Lilibeth A. Salvador-Reyes; Margo G. Haygood; Eric W. Schmidt; Gisela P. Concepcion

doi:10.1021/acs.jnatprod.8b00979

Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium

Noel M. Lacerna, Bailey W. Miller, Albebson L. Lim, Jortan O. Tun, Jose Miguel D. Robes, Mark Jeremiah B. Cleofas, Zhenjian Lin, Lilibeth A. Salvador-Reyes, Margo G. Haygood, Eric W. Schmidt, Gisela P. Concepcion

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21 Scopus citations

Abstract

Three new pyoluteorin analogues, mindapyrroles A-C (1-3), were purified from Pseudomonas aeruginosa strain 1682U.R.0a.27, a gill-associated bacterium isolated from the tissue homogenate of the giant shipworm Kuphus polythalamius. Mindapyrroles B and C inhibit the growth of multiple pathogenic bacteria, with mindapyrrole B (2) showing the most potent antimicrobial activity and widest selectivity index over mammalian cells. Preliminary structure-activity relationship analysis showed that dimerization of the pyoluteorin moiety through a C-C linkage is detrimental to the antimicrobial activity, but addition of an aerugine unit in the methylene bridge is favorable for both the antimicrobial activity and selectivity index.

Original language	English (US)
Pages (from-to)	1024-1028
Number of pages	5
Journal	Journal of Natural Products
Volume	82
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.8b00979
State	Published - Apr 26 2019

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.8b00979

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title = "Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium",

abstract = "Three new pyoluteorin analogues, mindapyrroles A-C (1-3), were purified from Pseudomonas aeruginosa strain 1682U.R.0a.27, a gill-associated bacterium isolated from the tissue homogenate of the giant shipworm Kuphus polythalamius. Mindapyrroles B and C inhibit the growth of multiple pathogenic bacteria, with mindapyrrole B (2) showing the most potent antimicrobial activity and widest selectivity index over mammalian cells. Preliminary structure-activity relationship analysis showed that dimerization of the pyoluteorin moiety through a C-C linkage is detrimental to the antimicrobial activity, but addition of an aerugine unit in the methylene bridge is favorable for both the antimicrobial activity and selectivity index.",

author = "Lacerna, {Noel M.} and Miller, {Bailey W.} and Lim, {Albebson L.} and Tun, {Jortan O.} and Robes, {Jose Miguel D.} and Cleofas, {Mark Jeremiah B.} and Zhenjian Lin and Salvador-Reyes, {Lilibeth A.} and Haygood, {Margo G.} and Schmidt, {Eric W.} and Concepcion, {Gisela P.}",

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doi = "10.1021/acs.jnatprod.8b00979",

language = "English (US)",

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AU - Lacerna, Noel M.

AU - Miller, Bailey W.

AU - Lim, Albebson L.

AU - Tun, Jortan O.

AU - Robes, Jose Miguel D.

AU - Cleofas, Mark Jeremiah B.

AU - Lin, Zhenjian

AU - Salvador-Reyes, Lilibeth A.

AU - Haygood, Margo G.

AU - Schmidt, Eric W.

AU - Concepcion, Gisela P.

PY - 2019/4/26

Y1 - 2019/4/26

N2 - Three new pyoluteorin analogues, mindapyrroles A-C (1-3), were purified from Pseudomonas aeruginosa strain 1682U.R.0a.27, a gill-associated bacterium isolated from the tissue homogenate of the giant shipworm Kuphus polythalamius. Mindapyrroles B and C inhibit the growth of multiple pathogenic bacteria, with mindapyrrole B (2) showing the most potent antimicrobial activity and widest selectivity index over mammalian cells. Preliminary structure-activity relationship analysis showed that dimerization of the pyoluteorin moiety through a C-C linkage is detrimental to the antimicrobial activity, but addition of an aerugine unit in the methylene bridge is favorable for both the antimicrobial activity and selectivity index.

AB - Three new pyoluteorin analogues, mindapyrroles A-C (1-3), were purified from Pseudomonas aeruginosa strain 1682U.R.0a.27, a gill-associated bacterium isolated from the tissue homogenate of the giant shipworm Kuphus polythalamius. Mindapyrroles B and C inhibit the growth of multiple pathogenic bacteria, with mindapyrrole B (2) showing the most potent antimicrobial activity and widest selectivity index over mammalian cells. Preliminary structure-activity relationship analysis showed that dimerization of the pyoluteorin moiety through a C-C linkage is detrimental to the antimicrobial activity, but addition of an aerugine unit in the methylene bridge is favorable for both the antimicrobial activity and selectivity index.

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Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium

Abstract

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