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Kinanthraquinone, a new anthraquinone carboxamide isolated from Streptomyces reveromyceticus SN-593-44

The Journal of Antibioticsvolume 71pages480482 (2018) | Download Citation


A new anthraquinone derivative, kinanthraquinone (1) was isolated from Streptomyces reveromyceticus SN-593-44. Its structure was determined by the combination of spectroscopic methods including NMR and MS. Kinanthraquinone had a characteristic carboxamide group and was a rare class of metabolite as an anthraquinone derivative isolated from microbes. It showed moderate cytotoxocity against HL-60 and srcts-NRK cell with IC50 value of 7.9 and 10 μM, respectively.

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  1. 1.

    Larsson J, Gottfries J, Muresan S, Backlund A. ChemGPS-NP: tuned for navigation in biologically relevant chemical space. J Nat Prod. 2007;70:789–94.

  2. 2.

    Osada H. Trends in bioprobe research. In: Osada H, editor. Bioprobes. Berlin: Springer; 2000. p. 1–14.

  3. 3.

    Kakeya H, et al. Cytotrienin A, a novel apoptosis inducer in human leukemia HL-60 cells. J Antibiot. 1997;50:370–2.

  4. 4.

    Kakeya H, et al. Epoxyquinol A, a highly functionalized pentaketide dimer with antiangiogenic activity isolated from fungal metabolites. J Am Chem Soc. 2002;124:3496–7.

  5. 5.

    Asami Y, et al. Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org Lett. 2002;4:2845–8.

  6. 6.

    Osada H, Koshino H, Isono K, Takahashi H, Kawanishi G. Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor. J Antibiot. 1991;44:259–61.

  7. 7.

    Woo JT, et al. Reveromycin A, an agent for osteoporosis, inhibits bone resorption by inducing apoptosis specifically in osteoclasts. Proc Natl Acad Sci USA. 2006;103:4729–34.

  8. 8.

    Takahashi S, et al. Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation. Nat Chem Biol. 2011;7:461–8.

  9. 9.

    Takahashi S, et al. Structure-function analyses of cytochrome P450revI involved in reveromycin A biosynthesis and evaluation of the biological activity of its substrate, reveromycin T. J Biol Chem. 2014;289:32446–58.

  10. 10.

    Miyazawa T, et al. Identification of middle chain fatty Acyl-CoA ligase responsible for the biosynthesis of 2-alkylmalonyl-CoAs for polyketide extender unit. J Biol Chem. 2015;290:26994–7011.

  11. 11.

    Panthee S, et al. Furaquinocins I and J: novel polyketide isoprenoid hybrid compounds from Streptomyces reveromyceticus SN-593. J Antibiot. 2011;64:509–13.

  12. 12.

    Osada H, Nogawa T. Systematic isolation of microbial metabolites for natural products depository (NPDepo). Pure Appl Chem. 2012;81:1407–20.

  13. 13.

    Nogawa T, et al. Verticilactam, a new macrolactam isolated from a microbial metabolite fraction library. Org Lett. 2010;12:4564–7.

  14. 14.

    Nogawa T, et al. Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library. J Antibiot. 2012;65:123–8.

  15. 15.

    Nogawa T, et al. Pyrrolizilactone, a new pyrrolizidinone metabolite produced by a fungus. J Antibiot. 2013;66:621–3.

  16. 16.

    Nogawa T, et al. Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058. J Antibiot. (2017).

  17. 17.

    Finlay AC, Hobby GL, et al. Terramycin, a new antibiotic. Science. 1950;111:85.

  18. 18.

    Lesnik U, et al. Construction of a new class of tetracycline lead structures with potent antibacterial activity through biosynthetic engineering. Angew Chem Int Ed Engl. 2015;54:3937–40.

  19. 19.

    Changsheng WU, Young-Hae C, Wezel V, Phillippus, G. Novel polyketides, methods of use and preparation. WO/2016/195495/A2, 8 December (2016).

  20. 20.

    Wang P, Gao X, Chooi YH, Deng Z, Tang Y. Genetic characterization of enzymes involved in the priming steps of oxytetracycline biosynthesis in Streptomyces rimosus. Microbiology. 2011;157:2401–9.

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We thank Dr. M. Uramoto for useful discussion about the structural identification. We also thank Ms A. Okano and H. Aono for an evaluation of biological activity.

Author information


  1. RIKEN Center for Sustainable Resource Science, Natural Product Biosynthesis Research Unit, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    • Hiroshi Takagi
    •  & Shunji Takahashi
  2. RIKEN Center for Sustainable Resource Science, Chemical biology Research Group, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan

    • Toshihiko Nogawa
    • , Yushi Futamura
    •  & Hiroyuki Osada


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The authors declare that they have no conflict of interest.

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Correspondence to Hiroyuki Osada.

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