Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Xiachang Wang; Sherif I. Elshahawi; Wenlong Cai; Yinan Zhang; Larissa V. Ponomareva; Xiabin Chen; Gregory C. Copley; James C. Hower; Chang Guo Zhan; Sean Parkin; Jürgen Rohr; Steven G. Van Lanen; Khaled A. Shaaban; Jon S. Thorson

doi:10.1021/acs.jnatprod.7b00108

Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Xiachang Wang, Sherif I. Elshahawi, Wenlong Cai, Yinan Zhang, Larissa V. Ponomareva, Xiabin Chen, Gregory C. Copley, James C. Hower, Chang Guo Zhan, Sean Parkin, Jürgen Rohr, Steven G. Van Lanen, Khaled A. Shaaban, Jon S. Thorson

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

26 Scopus citations

Abstract

The structures of 12 new “enantiomeric”-like abyssomicin metabolites (abyssomicins M-X) from Streptomyces sp. LC-6-2 are reported. Of this set, the abyssomicin W (11) contains an unprecedented 8/6/6/6 tetracyclic core, while the bicyclic abyssomicin X (12) represents the first reported naturally occurring linear spirotetronate. Metabolite structures were determined based on spectroscopic data and X-ray crystallography, and Streptomyces sp. LC-6-2 genome sequencing also revealed the corresponding putative biosynthetic gene cluster.

Original language	English
Pages (from-to)	1141-1149
Number of pages	9
Journal	Journal of Natural Products
Volume	80
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.7b00108
State	Published - Apr 28 2017

Bibliographical note

Publisher Copyright:
© 2017 The American Chemical Society and American Society of Pharmacognosy.

Funding

This work was supported by National Institutes of Health grants R01 GM115261 (J.S.T.) and T32 DA016176 (Y.Z.), the University of Kentucky College of Pharmacy, the University of Kentucky Markey Cancer Center, and the National Center for Advancing Translational Sciences (UL1TR001998).

Funders	Funder number
University of Kentucky
National Institutes of Health (NIH)	R01 GM115261
National Institute on Drug Abuse	T32DA016176
National Center for Advancing Translational Sciences (NCATS)	UL1TR001998
University of Kentucky Markey Cancer Center

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.7b00108

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Wang, X., Elshahawi, S. I., Cai, W., Zhang, Y., Ponomareva, L. V., Chen, X., Copley, G. C., Hower, J. C., Zhan, C. G., Parkin, S., Rohr, J., Van Lanen, S. G., Shaaban, K. A., & Thorson, J. S. (2017). Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2. Journal of Natural Products, 80(4), 1141-1149. https://doi.org/10.1021/acs.jnatprod.7b00108

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abstract = "The structures of 12 new “enantiomeric”-like abyssomicin metabolites (abyssomicins M-X) from Streptomyces sp. LC-6-2 are reported. Of this set, the abyssomicin W (11) contains an unprecedented 8/6/6/6 tetracyclic core, while the bicyclic abyssomicin X (12) represents the first reported naturally occurring linear spirotetronate. Metabolite structures were determined based on spectroscopic data and X-ray crystallography, and Streptomyces sp. LC-6-2 genome sequencing also revealed the corresponding putative biosynthetic gene cluster.",

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AU - Elshahawi, Sherif I.

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AU - Zhang, Yinan

AU - Ponomareva, Larissa V.

AU - Chen, Xiabin

AU - Copley, Gregory C.

AU - Hower, James C.

AU - Zhan, Chang Guo

AU - Parkin, Sean

AU - Rohr, Jürgen

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AU - Shaaban, Khaled A.

AU - Thorson, Jon S.

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Bi- and Tetracyclic Spirotetronates from the Coal Mine Fire Isolate Streptomyces sp. LC-6-2

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

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