Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8

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

doi:10.1021/acs.orglett.5b01203

Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8

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

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

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.

Original language	English
Pages (from-to)	2796-2799
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01203
State	Published - Jun 5 2015

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Wang, X., Reynolds, A. R., Elshahawi, S. I., Shaaban, K. A., Ponomareva, L. V., Saunders, M. A., Elgumati, I. S., Zhang, Y., Copley, G. C., Hower, J. C., Sunkara, M., Morris, A. J., Kharel, M. K., Van Lanen, S. G., Prendergast, M. A., & Thorson, J. S. (2015). Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8. Organic Letters, 17(11), 2796-2799. https://doi.org/10.1021/acs.orglett.5b01203

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title = "Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8",

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.",

author = "Xiachang Wang and Reynolds, {Anna R.} and Elshahawi, {Sherif I.} and Shaaban, {Khaled A.} and Ponomareva, {Larissa V.} and Saunders, {Meredith A.} and Elgumati, {Ibrahim S.} and Yinan Zhang and Copley, {Gregory C.} and Hower, {James C.} and Manjula Sunkara and Morris, {Andrew J.} and Kharel, {Madan K.} and {Van Lanen}, {Steven G.} and Prendergast, {Mark A.} and Thorson, {Jon S.}",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jun,

day = "5",

doi = "10.1021/acs.orglett.5b01203",

language = "English",

volume = "17",

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Wang, X, Reynolds, AR, Elshahawi, SI, Shaaban, KA, Ponomareva, LV, Saunders, MA, Elgumati, IS, Zhang, Y, Copley, GC, Hower, JC, Sunkara, M, Morris, AJ, Kharel, MK, Van Lanen, SG , Prendergast, MA & Thorson, JS 2015, 'Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8', Organic Letters, vol. 17, no. 11, pp. 2796-2799. https://doi.org/10.1021/acs.orglett.5b01203

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T1 - Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8

AU - Wang, Xiachang

AU - Reynolds, Anna R.

AU - Elshahawi, Sherif I.

AU - Shaaban, Khaled A.

AU - Ponomareva, Larissa V.

AU - Saunders, Meredith A.

AU - Elgumati, Ibrahim S.

AU - Zhang, Yinan

AU - Copley, Gregory C.

AU - Hower, James C.

AU - Sunkara, Manjula

AU - Morris, Andrew J.

AU - Kharel, Madan K.

AU - Van Lanen, Steven G.

AU - Prendergast, Mark A.

AU - Thorson, Jon S.

PY - 2015/6/5

Y1 - 2015/6/5

N2 - 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.

AB - 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.

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ER -

Terfestatins B and C, new p -terphenyl glycosides produced by streptomyces sp. RM-5-8

Abstract

Bibliographical note

ASJC Scopus subject areas

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