Original Article

Quadoctomycin, a 48-membered macrolide antibiotic from Streptomyces sp. MM168-141F8

  • The Journal of Antibiotics volume 71, pages 9196 (2018)
  • doi:10.1038/ja.2017.140
  • Download Citation


Drug-resistant bacteria are still emerging, and screening of new skeletal antibiotics is important. During our continuous screening for antimicrobial agents, we discovered a new antimicrobial, named quadoctomycin, from solid culture of Streptomyces sp. MM168-141F8. The substance was purified by solvent extraction, silica gel chromatography and HPLC. Structural elucidation of quadoctomycin was performed by MS and NMR analyses and chemical degradation. Quadoctomycin possesses a 48-membered polyol macrolide skeleton in which an α-D-mannoside is connected to C-22 by an O-glycosidic linkage. The structure of quadoctomycin was found to be related to that of monazomycin A based on the analyses of NMR spectra in the same solvent (pyridine-d5). Quadoctomycin showed potent antibacterial activity against Staphylococcus aureus, including methicillin-resistant S. aureus, and other Gram-positive pathogenic bacteria such as Enterococcus faecalis and E. faecium (including drug-resistant strains), but did not show activity toward Gram-negative bacteria or Candida albicans.

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  1. 1.

    World Health Organization World Health Day – 7 April 2011 (2011).

  2. 2.

    United States Centers for Disease Control and Prevention. Antibiotic resistance threats in the United States 2013 (2013).

  3. 3.

    , , & New tuberculosis drug leads from naturally occurring compounds. Int. J. Infect. Dis. 56, 212–220 (2017).

  4. 4.

    Targeting mycobacterial enzymes with natural products. Chem. Biol. 22, 1288–1300 (2015).

  5. 5.

    , & Tuberculosis: clinical trials and new drug regimens. Curr. Opin. Pulm. Med. 20, 280–286 (2014).

  6. 6.

    First-line chemotherapy in the retreatment of bacteriological relapses of pulmonary tuberculosis following a shortcourse regimen. Lancet 307, 162–163 (1976).

  7. 7.

    , , & Structure of monazomycin, A new ionophohous antibiotic. Tetrahedron Lett. 22, 5217–5220 (1981).

  8. 8.

    , , , & Monazomycin, a new antibiotic produced by a Streptomyces. J. Antibiot. Ser. A 16, 127–131 (1963).

  9. 9.

    , , & Structure of a novel 60-membered macrolide, quinolidomicin A1. J. Am. Chem. Soc. 115, 3014–3015 (1993).

  10. 10.

    , , & Quinolidomicins A1, A2 and B1, novel 60-membered macrolide antibiotics. II. Structure elucidation. J. Antibiot. 46, 1563–1569 (1993).

  11. 11.

    et al. Monazomycin B, a new macrolide antibiotic of the monazomycin family. J. Antibiot. 43, 438–440 (1990).

  12. 12.

    & Simplified approach to identification of aerobic actinomycetes by thin-layer chromatography. Appl. Microbiol. 28, 226–231 (1974).

  13. 13.

    , , & Complete nucleotide sequence of a 16S ribosomal RNA gene from Escherichia coli. Proc. Natl Acad. Sci. USA 75, 4801–4805 (1978).

  14. 14.

    Introducing EzTaxon-e: a prokaryotic 16S rRNA gene sequence database with phylotypes that represent uncultured species. Int. J. Syst. Evol. Microbiol. 62, 716–721 (2012).

  15. 15.

    Clinical and Laboratory Standards InstituteMethods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically; Approved Standard-Eighth Edition M07-A8 CLSI (2009).

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We thank Dr K Furihata, University of Tokyo, for providing NMR spectra of monazomycin A. We thank Ms N Kinoshita, Ms R Arisaka and Ms Y Shibuya, Institute of Microbial Chemistry (BIKAKEN), Tokyo for providing technical assistance.

Author information


  1. Institute of Microbial Chemistry (BIKAKEN), Tokyo, Japan

    • Ryuichi Sawa
    • , Yumiko Kubota
    • , Maya Umekita
    • , Masaki Hatano
    • , Chigusa Hayashi
    •  & Masayuki Igarashi


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Competing interests

The authors declare no conflict of interest.

Corresponding authors

Correspondence to Ryuichi Sawa or Masayuki Igarashi.

Supplementary information

Supplementary Information accompanies the paper on The Journal of Antibiotics website (http://www.nature.com/ja)