Next Article in Journal
Comprehensive Expression Profiling and Functional Network Analysis of Porphyra-334, One Mycosporine-Like Amino Acid (MAA), in Human Keratinocyte Exposed with UV-radiation
Next Article in Special Issue
Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies
Previous Article in Journal
Isolation and Selection of Microalgal Strains from Natural Water Sources in Viet Nam with Potential for Edible Oil Production
Previous Article in Special Issue
Interpreting Microbial Biosynthesis in the Genomic Age: Biological and Practical Considerations
Article Menu
Issue 7 (July) cover image

Export Article

Open AccessArticle
Mar. Drugs 2017, 15(7), 195; doi:10.3390/md15070195

Bonnevillamides, Linear Heptapeptides Isolated from a Great Salt Lake-Derived Streptomyces sp.

1
Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA
2
Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, UT 84112, USA
*
Author to whom correspondence should be addressed.
Received: 2 June 2017 / Revised: 13 June 2017 / Accepted: 19 June 2017 / Published: 24 June 2017
(This article belongs to the Special Issue Connecting Marine Microbial Natural Products to Biosynthetic Pathways)
View Full-Text   |   Download PDF [2188 KB, uploaded 24 June 2017]   |  

Abstract

Streptomyces sp. GSL-6B was isolated from sediment collected from the Great Salt Lake and investigation of its organic extract led to the isolation of three new linear heptapeptides, bonnevillamides A (1), B (2), and C (3). The bonnevillamides represent a new class of linear peptides featuring unprecedented non-proteinogenic amino acids. All three peptides contain the newly characterized bonnevillic acid moiety (3-(3,5-dichloro-4-methoxyphenyl)-2-hydroxyacrylic acid), as well as a heavily modified proline residue. Moreover, in bonnevillamide A, the terminal proline residue found in bonnevillamides B and C is replaced with 4-methyl-azetidine-2-carboxylic acid methyl ester. The structures of the three heptapeptides were elucidated by NMR, high-resolution electrospray ionization mass spectroscopy (HRESIMS), and LC-MS/MS, and the absolute configuration of all proteinogenic amino acid residues were determined by advanced Marfey’s method. Bonnevillamides A, B and C were evaluated for their effects on zebrafish embryo development. All three heptapeptides were shown to modulate heart growth and cardiac function, with bonnevillamide B having the most pronounced effect. View Full-Text
Keywords: Great Salt Lake; hypersaline environment; heptapeptide; azetidine; Streptomyces sp.; zebrafish Great Salt Lake; hypersaline environment; heptapeptide; azetidine; Streptomyces sp.; zebrafish
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Wu, G.; Nielson, J.R.; Peterson, R.T.; Winter, J.M. Bonnevillamides, Linear Heptapeptides Isolated from a Great Salt Lake-Derived Streptomyces sp.. Mar. Drugs 2017, 15, 195.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Mar. Drugs EISSN 1660-3397 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top