Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp.

Peng Sun; Katherine N. Maloney; Sang Jip Nam; Nina M. Haste; Ritesh Raju; William Aalbersberg; Paul R. Jensen; Victor Nizet; Mary E. Hensler; William Fenical

doi:10.1016/j.bmc.2011.06.053

Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp.

Peng Sun, Katherine N. Maloney, Sang Jip Nam, Nina M. Haste, Ritesh Raju, William Aalbersberg, Paul R. Jensen, Victor Nizet, Mary E. Hensler, William Fenical

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

56 Scopus citations

Abstract

Three new depsipeptides, fijimycins A-C (1-3), together with the known etamycin A (4), were isolated and identified from the fermentation broth of strain CNS-575, a Streptomyces sp. cultured from a marine sediment sample collected off Nasese, Fiji. The planar structures of the new fijimycins were assigned by combined interpretation of NMR and MS/MS spectroscopic data. These assignments were complicated by the fact that 1-3 occurred as complex amide conformational mixtures. The absolute configurations of the component amino acids were established using the Marfey's method. Fijimycins A-C, and etamycin A, were shown to possess significant in vitro antibacterial activity against three methicillin-resistant Staphylococcus aureus (MRSA) strains with MIC ₁₀₀ values between 4 and 16 μg mL ^-1.

Original language	English
Pages (from-to)	6557-6562
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	19
Issue number	22
DOIs	https://doi.org/10.1016/j.bmc.2011.06.053
State	Published - 15 Nov 2011

Bibliographical note

Funding Information:
This research is a result of financial support from the National Institutes of Health/Fogarty Center International Cooperative Biodiversity Groups program (grant U01-TW007401-01 ) and NIH award RO1 GM084350-01 . We thank the people of Fiji for their hospitality and the government and local resource owners for permission to collect samples in their local offshore waters. We thank C. A. Kauffman for fermentation assistance and S. Kelly for performing the 16S RNA analysis. We also thank A. Mrse (UCSD) for assistance with NMR experiments and Y. Su (UCSD) for HRMS and MS/MS data.

Keywords

Antibacterial depsipeptides
Etamycin class antibacterials
MRSA activity

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title = "Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp.",

abstract = "Three new depsipeptides, fijimycins A-C (1-3), together with the known etamycin A (4), were isolated and identified from the fermentation broth of strain CNS-575, a Streptomyces sp. cultured from a marine sediment sample collected off Nasese, Fiji. The planar structures of the new fijimycins were assigned by combined interpretation of NMR and MS/MS spectroscopic data. These assignments were complicated by the fact that 1-3 occurred as complex amide conformational mixtures. The absolute configurations of the component amino acids were established using the Marfey's method. Fijimycins A-C, and etamycin A, were shown to possess significant in vitro antibacterial activity against three methicillin-resistant Staphylococcus aureus (MRSA) strains with MIC 100 values between 4 and 16 μg mL -1.",

keywords = "Antibacterial depsipeptides, Etamycin class antibacterials, MRSA activity",

author = "Peng Sun and Maloney, {Katherine N.} and Nam, {Sang Jip} and Haste, {Nina M.} and Ritesh Raju and William Aalbersberg and Jensen, {Paul R.} and Victor Nizet and Hensler, {Mary E.} and William Fenical",

note = "Funding Information: This research is a result of financial support from the National Institutes of Health/Fogarty Center International Cooperative Biodiversity Groups program (grant U01-TW007401-01 ) and NIH award RO1 GM084350-01 . We thank the people of Fiji for their hospitality and the government and local resource owners for permission to collect samples in their local offshore waters. We thank C. A. Kauffman for fermentation assistance and S. Kelly for performing the 16S RNA analysis. We also thank A. Mrse (UCSD) for assistance with NMR experiments and Y. Su (UCSD) for HRMS and MS/MS data. ",

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AU - Haste, Nina M.

AU - Raju, Ritesh

AU - Aalbersberg, William

AU - Jensen, Paul R.

AU - Nizet, Victor

AU - Hensler, Mary E.

AU - Fenical, William

N1 - Funding Information: This research is a result of financial support from the National Institutes of Health/Fogarty Center International Cooperative Biodiversity Groups program (grant U01-TW007401-01 ) and NIH award RO1 GM084350-01 . We thank the people of Fiji for their hospitality and the government and local resource owners for permission to collect samples in their local offshore waters. We thank C. A. Kauffman for fermentation assistance and S. Kelly for performing the 16S RNA analysis. We also thank A. Mrse (UCSD) for assistance with NMR experiments and Y. Su (UCSD) for HRMS and MS/MS data.

PY - 2011/11/15

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Fijimycins A-C, three antibacterial etamycin-class depsipeptides from a marine-derived Streptomyces sp.

Abstract

Bibliographical note

Keywords

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