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Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain

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    Hytramycins V and I, Anti-Mycobacterium tuberculosis Hexapeptides from a Streptomyces hygroscopicus Strain
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    † †Institute for Tuberculosis Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, United States
    § Center for Nutraceutical and Pharmaceutical Materials, Myongji University, Cheoin-gu, Yongin, Gyeonggi-Do 449-728, Korea
    ⊥ Division of Bioscience and Bioinformatics, College of Natural Science, Myongji University, Cheoin-gu, Yongin, Gyeonggi-Do 449-728, Korea
    *(G. F. Pauli) E-mail: [email protected]. Tel: +1 (312) 355-1949. Fax: +1 (312) 355-2693.
    *(S. Cho) E-mail: [email protected]. Tel: +1 (312) 771-7679.
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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2013, 76, 11, 2009–2018
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    https://doi.org/10.1021/np400145u
    Published November 13, 2013
    Copyright © 2013 The American Chemical Society and American Society of Pharmacognosy
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    Abstract

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    Thirty-five thousand actinomycete extracts were screened for anti-Mycobacterium tuberculosis (M. tb) activity, followed by C18 cartridge fractionation of 37 prioritized extracts. Based on MICs against replicating and nonreplicating M. tb, and IC50 values against Vero cells to generate selectivity indices, seven fractions from seven different strains were selected for further examination. When cultured in G.S.S. media and extracted with ethyl acetate, the Streptomyces hygroscopicus strain ECUM 14046 yielded an extract with promising anti-M. tb activity and a well-defined chromatographic profile. Fractionation by preparative HPLC and subsequent structure elucidation of two active fractions using 1D- and 2D-NMR and MS methods revealed the presence of two cyclohexapeptides, hytramycins V and I, each containing three unusual piperazic acid moieties. The use of 1H iterative full spin analysis (HiFSA) on both hytramycins confirmed that quantum mechanics-simulated spectra match the experimental data, and all JH,H and δH values are consistent with the proposed structures. The absolute configuration of each amino acid moiety was determined by Marfey’s method. The MICs against replicating and, more importantly, nonreplicating M. tb fall into the range of some existing second-line anti-TB drugs, such as streptomycin and capreomycin, respectively. The activities were maintained against M. tb strains that represent the major global clades, as well as H37Rv-isogenic strains that are resistant to individual clinical anti-TB drugs.

    Copyright © 2013 The American Chemical Society and American Society of Pharmacognosy

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    Accurate mass, MS/MS, IR, 1H NMR, 13C NMR, COSY, HSQC, and HMBC spectra of 1 and 2 and DEPT-135, TOCSY, NOESY, and semiselective HMBC spectra of 1. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Journal of Natural Products

    Cite this: J. Nat. Prod. 2013, 76, 11, 2009–2018
    Click to copy citationCitation copied!
    https://doi.org/10.1021/np400145u
    Published November 13, 2013
    Copyright © 2013 The American Chemical Society and American Society of Pharmacognosy
    Request reuse permissions

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