Structure and biosynthesis of mayamycin B, a new polyketide with antibacterial activity from Streptomyces sp. 120454


Mayamycin B, a new antibacterial type II polyketide, together with its known congener mayamycin A, were isolated from Streptomyces sp. 120454. The structure of new compound was elucidated by extensive spectroscopic analysis and comparison with literature data. Sequencing and bioinformatics analysis revealed the biosynthetic gene cluster for mayamycins A and B.

Access optionsAccess options

Rent or Buy article

Get time limited or full article access on ReadCube.


All prices are NET prices.

Fig. 1
Fig. 2
Fig. 3


  1. 1.

    Minotti G, et al. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacol Rev. 2004;56:185–229.

  2. 2.

    Kharel MK, et al. Angucyclines: biosynthesis, mode-of-action, new natural products and synthesis. Nat Prod Rep. 2012;29:264–325.

  3. 3.

    Das A, Khosla C. Biosynthesis of aromatic polyketides in bacteria. Acc Chem Res. 2009;42:631–639.

  4. 4.

    Moore BS, Hertweck C. Biosynthesis and attachment of novel bacterial polyketide synthase starter units. Nat Prod Rep. 2002;19:70–99.

  5. 5.

    Omura S, et al. New antitumor antibiotics, OS-4742A1, A2, B1 and B2 produced by a strain of Streptomyces. J Antibiot. 1997;30:908–16.

  6. 6.

    Martin GDA, et al. Marmycins A and B, cytotoxic pentacyclic C-glycosides from a marine sediment-derived actinomycete related to the genus Streptomyces. J Nat Prod. 2007;70:1406–9.

  7. 7.

    Shaaban KA, et al. 11-Deoxylandomycinone and landomycins X-Z, new cytotoxic angucyclin(on)es from a Streptomyces cyanogenus K62 mutant strain. J Antibiot. 2011;64:141–50.

  8. 8.

    Patrikainen P, et al. Structure-based engineering of angucyclinone 6-ketoreductases. Chem Biol. 2014;21:1381–1391.

  9. 9.

    Zhu XC, et al. Cytotoxic rearranged angucycline glycosides from deep sea-derived Streptomyces lusitanus SCSIO LR32. J Antibiot. 2017;70:819–22.

  10. 10.

    Imke S, et al. Mayamycin, a cytotoxic polyketide from a Streptomyces strain isolated from the marine sponge Halichondria panacea. J Nat Prod. 2010;73:1309–12.

  11. 11.

    Liang. Y, et al. Bioactive polycyclic quinones from marine Streptomyces sp. 182SMLY. Mar Drugs. 2016;14:10.

  12. 12.

    Han L, et al. Cloning and characterization of polyketide synthase genes for jadomycin B biosynthesis in Streptomyces venezuelae ISP5230. Microbiology. 1994;140:3379–89.

  13. 13.

    Rix U, et al. The oxidative ring cleavage in jadomycin biosynthesis: a multistep oxygenation cascade in a biosynthetic black box. ChemBioChem. 2005;6:838–45.

  14. 14.

    Chen YH, et al. Functional analyses of oxygenases in jadomycin biosynthesis and identification of JadH as a bifunctional oxygenase/dehydrase. J Biol Chem. 2005;280:22508–14.

  15. 15.

    Kulowski K, et al. Functional characterization of the jadI gene as a cyclase forming angucyclinones. J Am Chem Soc. 1999;121:1786–94.

  16. 16.

    Ichinose K, et al. Cloning, sequencing and heterologous expression of the medermycin biosynthetic gene cluster of Streptomyces sp. AM-7161: towards comparative analysis of the benzoisochromanequinone gene clusters. Microbiology. 2003;149:1633–45.

  17. 17.

    Ichinose K, et al. The granaticin biosynthetic gene cluster of Streptomyces violaceoruber Tü22: sequence analysis and expression in a heterologous host. Chem Biol. 1998;5:647–59.

  18. 18.

    Faust B, et al. Two new tailoring enzymes, a glycosyltransferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tü2717. Microbiology. 2000;146:147–54.

  19. 19.

    Trefzer A, et al. Biosynthetic gene cluster of simocyclinone, a natural multihybrid antibiotic. Antimicrob Agents Chemother. 2002;46:1174–82.

Download references


We thank Dr. Ben Shen (The Scripps Research Institute) for his generous gift of S. sp. 120454. This work was financially supported by Natural Science Foundation of China (81522042, 21572100, 81421091, 81500059, 81673333, and 21672101), and Jiangsu Provincial Key Medical Discipline (laboratory) (no. ZDXKA2016020).

Author information

Correspondence to Rui Hua Jiao or Hui Ming Ge.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interests.

Electronic supplementary material

Structure and biosynthesis of mayamycin B, a new polyketide with antibacterial activity from Streptomyces sp. 120454

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark