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 Haygood, Eric W. Schmidt, Gisela P. Concepcion

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)1024-1028
Number of pages5
JournalJournal of Natural Products
Volume82
Issue number4
DOIs
StatePublished - Apr 26 2019
Externally publishedYes

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Bacteria
Dimerization
Structure-Activity Relationship
Pseudomonas aeruginosa
Cells
Tissue
Growth
pyoluteorin

ASJC Scopus subject areas

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

Cite this

Lacerna, N. M., Miller, B. W., Lim, A. L., Tun, J. O., Robes, J. M. D., Cleofas, M. J. B., ... Concepcion, G. P. (2019). Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium. Journal of Natural Products, 82(4), 1024-1028. https://doi.org/10.1021/acs.jnatprod.8b00979

Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium. / Lacerna, Noel M.; Miller, Bailey W.; Lim, Albebson L.; Tun, Jortan O.; Robes, Jose Miguel D.; Cleofas, Mark Jeremiah B.; Lin, Zhenjian; Salvador-Reyes, Lilibeth A.; Haygood, Margo; Schmidt, Eric W.; Concepcion, Gisela P.

In: Journal of Natural Products, Vol. 82, No. 4, 26.04.2019, p. 1024-1028.

Research output: Contribution to journalArticle

Lacerna, NM, Miller, BW, Lim, AL, Tun, JO, Robes, JMD, Cleofas, MJB, Lin, Z, Salvador-Reyes, LA, Haygood, M, Schmidt, EW & Concepcion, GP 2019, 'Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium', Journal of Natural Products, vol. 82, no. 4, pp. 1024-1028. https://doi.org/10.1021/acs.jnatprod.8b00979
Lacerna NM, Miller BW, Lim AL, Tun JO, Robes JMD, Cleofas MJB et al. Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium. Journal of Natural Products. 2019 Apr 26;82(4):1024-1028. https://doi.org/10.1021/acs.jnatprod.8b00979
Lacerna, Noel M. ; Miller, Bailey W. ; Lim, Albebson L. ; Tun, Jortan O. ; Robes, Jose Miguel D. ; Cleofas, Mark Jeremiah B. ; Lin, Zhenjian ; Salvador-Reyes, Lilibeth A. ; Haygood, Margo ; Schmidt, Eric W. ; Concepcion, Gisela P. / Mindapyrroles A-C, Pyoluteorin Analogues from a Shipworm-Associated Bacterium. In: Journal of Natural Products. 2019 ; Vol. 82, No. 4. pp. 1024-1028.
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