Terfestatins B and C, New p-terphenyl Glycosides Produced by Streptomyces sp. RM-5-8

Authors

Xiachang Wang, University of Kentucky
Anna R. Reynolds, University of Kentucky
Sherif Elshahawi, Chapman UniversityFollow
Khaled A. Shaaban, University of Kentucky
Larissa V. Ponomareva, University of Kentucky
Meredith A. Saunders, University of Kentucky
Ibrahim S. Elgumati, University of Kentucky
Yinan Zhang, University of Kentucky
Gregory C. Copley, University of Kentucky
James C. Hower, University of Kentucky
Manjula Sunkara, University of Kentucky
Andrew J. Morris, University of Kentucky
Madan K. Kharel, University of Kentucky
Steven G. Van Lanen, University of Kentucky
Mark A. Prendergast, University of Kentucky
Jon S. Thorson, University of Kentucky

Document Type

Article

Publication Date

5-11-2015

Abstract

Terfestatins B (1) and C (2), new p-terphenyls bearing a novel unsaturated hexuronic acid (4-deoxy-α-l-threo-hex-4-enopyranuronate), a unique β-d-glycosyl ester of 5-isoprenylindole-3-carboxylate (3) and the same rare sugar, and two new hygromycin precursors, were characterized as metabolites of the coal mine fire isolate Streptomyces sp. RM-5–8. EtOH damage neuroprotection assays using rat hippocampal-derived primary cell cultures with 1, 2, 3 and echoside B (a terfestatin C-3′-β-d-glucuronide from Streptomyces sp. RM-5– 8) revealed 1 as potently neuroprotective, highlighting a new potential application of the terfestatin scaffold.

Comments

This article was originally published in Organic Letters, volume 17, issue 11, in 2015. https://doi.org/10.1021/acs.orglett.5b01203

Recommended Citation

Wang X, Reynolds AR, Elshahawi SI, et al. Terfestatins B and C, new p-terphenyl glycosides produced by Streptomyces sp. RM-5-8. Org Lett. 2015;17(11):2796-2799. https://doi.org/10.1021/acs.orglett.5b01203

Copyright

American Chemical Society