Bonnevillamides, Linear Heptapeptides Isolated from a Great Salt Lake-Derived Streptomyces sp.
| Autor: | Wu G; Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA. Guangwei.Wu@utah.edu., Nielson JR; Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, UT 84112, USA. Jason.Nielson@pharm.utah.edu., Peterson RT; Department of Pharmacology and Toxicology, University of Utah, Salt Lake City, UT 84112, USA. Randall.Peterson@pharm.utah.edu., Winter JM; Department of Medicinal Chemistry, University of Utah, Salt Lake City, UT 84112, USA. Jaclyn.Winter@utah.edu. |
|---|---|
| Jazyk: | angličtina |
| Zdroj: | Marine drugs [Mar Drugs] 2017 Jun 24; Vol. 15 (7). Date of Electronic Publication: 2017 Jun 24. |
| DOI: | 10.3390/md15070195 |
| Abstrakt: | 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. Competing Interests: The authors declare no conflict of interest. |
| Databáze: | MEDLINE |
| Externí odkaz: |
|