Borrelidins F–I, cytotoxic and cell migration inhibiting agents from mangrove-derived Streptomyces rochei SCSIO ZJ89
[Display omitted] •Four new compounds (2–5) were isolated from Streptomyces rochei SCSIO ZJ89.•New cytotoxic SARs were identified.•Borrelidin H (4) is selective against cancer cells than non-malignant cells.•Borrelidin H (4) inhibits migration of cancer cells. Borrelidin A (1) is produced by several...
Gespeichert in:
Veröffentlicht in: | Bioorganic & medicinal chemistry 2018-05, Vol.26 (8), p.1488-1494 |
---|---|
Hauptverfasser: | , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | [Display omitted]
•Four new compounds (2–5) were isolated from Streptomyces rochei SCSIO ZJ89.•New cytotoxic SARs were identified.•Borrelidin H (4) is selective against cancer cells than non-malignant cells.•Borrelidin H (4) inhibits migration of cancer cells.
Borrelidin A (1) is produced by several species of Streptomyces and within its bioactive scaffold, the vinylic nitrile moiety is essential for activity. We report herein newly discovered members of the borrelidin family, borrelidin F (2), borrelidin G (3), borrelidin H (4) and borrelidin I (5); all were isolated from Streptomyces rochei SCSIO ZJ89 originating from a mangrove-derived sediment sample. These structurally diverse metabolites enabled a number of new structure-activity relationships (SARs) to be identified, especially with respect to the different configurations at the C11-OH and C12–C15 double bonds for which the absolute configurations were determined using spectroscopic methods. Importantly, borrelidin H (4) was found to have a therapeutic window superior to that of borrelidin A (1) in vitro and could inhibit migration of cancer cells. |
---|---|
ISSN: | 0968-0896 1464-3391 |
DOI: | 10.1016/j.bmc.2018.01.010 |