Ion Mobility Mass Spectrometry as an Efficient Tool for Identification of Streptorubin B in Streptomyces coelicolor M145

Andrew P. Marshall; Andrew R. Johnson; Marvin M. Vega; Regan J. Thomson; Erin E. Carlson

doi:10.1021/acs.jnatprod.9b00828

Ion Mobility Mass Spectrometry as an Efficient Tool for Identification of Streptorubin B in Streptomyces coelicolor M145

Andrew P. Marshall, Andrew R. Johnson, Marvin M. Vega, Regan J. Thomson, Erin E. Carlson^*

^*Corresponding author for this work

Chemistry

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

3 Scopus citations

Abstract

Ion mobility spectrometry was utilized to corroborate the identity of streptorubin B (2) as the natural product produced by Streptomyces coelicolor. Natural product 2 was initially assigned as butylcycloheptylprodigiosin (3), and only relatively recently was this assignment clarified. We present additional evidence of this assignment by comparing collisional cross sections (ω) of synthetic standards of 2, 3, and metacycloprodigiosin (4) to the cyclic prodiginine produced by S. coelicolor. Calculated theoretical ω values demonstrate that cyclic prodiginines could be identified without standards. This work highlights ion mobility as an efficient tool for the dereplication of natural products.

Original language	English (US)
Pages (from-to)	159-163
Number of pages	5
Journal	Journal of Natural Products
Volume	83
Issue number	1
DOIs	https://doi.org/10.1021/acs.jnatprod.9b00828
State	Published - Jan 24 2020

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.9b00828

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title = "Ion Mobility Mass Spectrometry as an Efficient Tool for Identification of Streptorubin B in Streptomyces coelicolor M145",

abstract = "Ion mobility spectrometry was utilized to corroborate the identity of streptorubin B (2) as the natural product produced by Streptomyces coelicolor. Natural product 2 was initially assigned as butylcycloheptylprodigiosin (3), and only relatively recently was this assignment clarified. We present additional evidence of this assignment by comparing collisional cross sections (ω) of synthetic standards of 2, 3, and metacycloprodigiosin (4) to the cyclic prodiginine produced by S. coelicolor. Calculated theoretical ω values demonstrate that cyclic prodiginines could be identified without standards. This work highlights ion mobility as an efficient tool for the dereplication of natural products.",

author = "Marshall, {Andrew P.} and Johnson, {Andrew R.} and Vega, {Marvin M.} and Thomson, {Regan J.} and Carlson, {Erin E.}",

note = "Funding Information: This work was supported by an NSF CAREER Award (to E.E.C.), a Sloan Research Fellow Award (to E.E.C.), the National Institutes of Health (R01GM085322 and R01GM124089 to R.J.T.), and the University of Minnesota. Funding Information: Mass spectrometry analysis was performed, in part, at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota. The content of this paper is the sole responsibility of the authors and does not represent endorsement by the MSL. Publisher Copyright: {\textcopyright} 2020 American Chemical Society and American Society of Pharmacognosy.",

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doi = "10.1021/acs.jnatprod.9b00828",

language = "English (US)",

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AU - Marshall, Andrew P.

AU - Johnson, Andrew R.

AU - Vega, Marvin M.

AU - Thomson, Regan J.

AU - Carlson, Erin E.

N1 - Funding Information: This work was supported by an NSF CAREER Award (to E.E.C.), a Sloan Research Fellow Award (to E.E.C.), the National Institutes of Health (R01GM085322 and R01GM124089 to R.J.T.), and the University of Minnesota. Funding Information: Mass spectrometry analysis was performed, in part, at The University of Minnesota Department of Chemistry Mass Spectrometry Laboratory (MSL), supported by the Office of the Vice President of Research, College of Science and Engineering, and the Department of Chemistry at the University of Minnesota. The content of this paper is the sole responsibility of the authors and does not represent endorsement by the MSL. Publisher Copyright: © 2020 American Chemical Society and American Society of Pharmacognosy.

PY - 2020/1/24

Y1 - 2020/1/24

N2 - Ion mobility spectrometry was utilized to corroborate the identity of streptorubin B (2) as the natural product produced by Streptomyces coelicolor. Natural product 2 was initially assigned as butylcycloheptylprodigiosin (3), and only relatively recently was this assignment clarified. We present additional evidence of this assignment by comparing collisional cross sections (ω) of synthetic standards of 2, 3, and metacycloprodigiosin (4) to the cyclic prodiginine produced by S. coelicolor. Calculated theoretical ω values demonstrate that cyclic prodiginines could be identified without standards. This work highlights ion mobility as an efficient tool for the dereplication of natural products.

AB - Ion mobility spectrometry was utilized to corroborate the identity of streptorubin B (2) as the natural product produced by Streptomyces coelicolor. Natural product 2 was initially assigned as butylcycloheptylprodigiosin (3), and only relatively recently was this assignment clarified. We present additional evidence of this assignment by comparing collisional cross sections (ω) of synthetic standards of 2, 3, and metacycloprodigiosin (4) to the cyclic prodiginine produced by S. coelicolor. Calculated theoretical ω values demonstrate that cyclic prodiginines could be identified without standards. This work highlights ion mobility as an efficient tool for the dereplication of natural products.

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Ion Mobility Mass Spectrometry as an Efficient Tool for Identification of Streptorubin B in Streptomyces coelicolor M145

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