PUBLICATION
Bonnevillamides, Linear Heptapeptides Isolated from a Great Salt Lake-Derived Streptomyces sp
- Authors
- Wu, G., Nielson, J.R., Peterson, R.T., Winter, J.M.
- ID
- ZDB-PUB-170705-8
- Date
- 2017
- Source
- Marine drugs 15(7): (Journal)
- Registered Authors
- Peterson, Randall
- Keywords
- Great Salt Lake, Streptomyces sp., azetidine, heptapeptide, hypersaline environment, zebrafish
- MeSH Terms
-
- Animals
- Dose-Response Relationship, Drug
- Embryo, Nonmammalian/drug effects
- Lakes/chemistry
- Larva/drug effects
- Models, Molecular
- Molecular Structure
- Peptides/chemistry*
- Peptides/metabolism
- Streptomyces/metabolism*
- Utah
- Zebrafish
- PubMed
- 28672784 Full text @ Mar. Drugs
Citation
Wu, G., Nielson, J.R., Peterson, R.T., Winter, J.M. (2017) Bonnevillamides, Linear Heptapeptides Isolated from a Great Salt Lake-Derived Streptomyces sp. Marine drugs. 15(7).
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.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping