Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Brief Communication
  • Published:

6,9-Dihydroxytetrangulol, a novel angucyclinone antibiotic accumulated in kiqO gene disruptant in the biosynthesis of kinanthraquinone

The Journal of Antibiotics volume 74, pages 593–595 (2021)Cite this article

Subjects

Abstract

A novel angucyclinone, 6,9-dihydroxytetrangulol, was isolated from Streptomyces lividans TK23 transformed with a kinanthraquinone biosynthetic gene cluster in which the kiqO gene was disrupted. The chemical structure was elucidated by spectroscopic analyses. It showed significant antibacterial activities with an IC50 value of 1.9 μM against Staphylococcus aureus and moderate anticancer activities against HL-60 cells.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Fig. 1

References

  1. Rohr J, Thiericke R. Angucycline group antibiotics. Nat Prod Rep. 1992;9:103–37.

    Article  CAS  Google Scholar 

  2. Kharel MK, Pahari P, Shepherd MD, Tibrewal N, Nybo SE, Shaaban KA, et al. Angucyclines: biosynthesis, mode-of-action, new natural products, and synthesis. Nat Prod Rep. 2012;29:264–325.

    Article  CAS  Google Scholar 

  3. Hertweck C, Luzhetskyy A, Rebets Y, Bechthold A. Type II polyketide synthases: gaining a deeper insight into enzymatic teamwork. Nat Prod Rep. 2007;24:162–90.

    Article  CAS  Google Scholar 

  4. Takagi H, Nogawa T, Futamura Y, Takahashi S, Osada H. Kinanthraquinone, a new anthraquinone carboxamide isolated from Streptomyces reveromyceticus SN-593-44. J Antibiot. 2018;71:480–2.

    Article  CAS  Google Scholar 

  5. Panthee S, Kito N, Hayashi T, Shimizu T, Ishikawa J, Hamamoto H, et al. Beta-carboline chemical signals induce reveromycin production through a LuxR family regulator in Streptomyces sp. SN-593. Sci Rep. 2020;10:10230.

    Article  CAS  Google Scholar 

  6. Takao R, Sakai K, Koshino H, Osada H, Takahashi S. Identification of the kinanthraquinone biosynthetic gene cluster by expression of an atypical response regulator. Biosci Biotechnol Biochem. 2021;85:714–21.

    Article  Google Scholar 

  7. Jiang X, Zhang Q, Zhu Y, Nie F, Wu Z, Yang C, et al. Isolation, structure elucidation and biosynthesis of benzo[b]fluorene nenestatin a from deep-sea derived Micromonospora echinospora SCSIO 04089. Tetrahedron. 2017;73:3585–90.

    Article  CAS  Google Scholar 

  8. Gould PJSaSJ. Kinamycin biosynthesis. derivation by excision of an acetate unit from a single-chain decaketide intermediate. J Am Chem Soc. 1987;109:5282–4.

    Article  Google Scholar 

  9. Yamashita N, Harada T, Shin-ya K, Seto H. 6-Hydroxytetrangulol, a new CPP32 protease inducer produced by Streptomyces sp. J Antibiot. 1998;51:79–81.

    Article  CAS  Google Scholar 

  10. Fang Z, Jiang X, Zhang Q, Zhang L, Zhang W, Yang C, et al. S-bridged thioether and structure-diversified angucyclinone derivatives from the South China sea-derived Micromonospora echinospora SCSIO 04089. J Nat Prod. 2020;83:3122–30.

    Article  CAS  Google Scholar 

  11. Fotso S, Mahmud T, Zabriskie TM, Santosa DA, Proteau PJ. Rearranged and unrearranged angucyclinones from Indonesian Streptomyces spp. J Antibiot. 2008;61:449–56.

    Article  CAS  Google Scholar 

  12. Carr G, Derbyshire ER, Caldera E, Currie CR, Clardy J. Antibiotic and antimalarial quinones from fungus-growing ant-associated Pseudonocardia sp. J Nat Prod. 2012;75:1806–9.

    Article  CAS  Google Scholar 

  13. Hu Z, Qin L, Wang Q, Ding W, Chen Z, Ma Z. Angucycline antibiotics and its derivatives from marine-derived actinomycete Streptomyces sp. A6H. Nat Prod Res. 2016;30:2551–8.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank Prof. Haruo Ikeda and Prof. Hiroyasu Onaka for providing the pKU592 and pTYM19 vectors, respectively. This work was supported by JSPS KAKENHI Grant Number 20H00416 to (ST).

Author information

Author notes

  1. These authors contributed equally: Katsuyuki Sakai, Risa Takao

Authors and Affiliations

  1. Natural Product Biosynthesis Research Unit, RIKEN Centre for Sustainable Resource Science, Wako, Saitama, Japan

    Katsuyuki Sakai, Risa Takao & Shunji Takahashi

  2. Graduate School of Science and Engineering, Saitama University; Shimo-Okubo 255, Sakura-ku, Saitama-shi, Saitama, Japan

    Risa Takao & Shunji Takahashi

  3. Molecular Structure Characterization Unit, Technology Platform Division, RIKEN Center for Sustainable Resource Science, Wako, Saitama, Japan

    Hiroyuki Koshino

  4. Chemical Biology Research Group, RIKEN Centre for Sustainable Resource Science, Wako, Saitama, Japan

    Yushi Futamura & Hiroyuki Osada

Authors
  1. Katsuyuki Sakai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Risa Takao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hiroyuki Koshino
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yushi Futamura
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hiroyuki Osada
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shunji Takahashi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shunji Takahashi.

Ethics declarations

Competing interests

The authors declare no competing interests.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sakai, K., Takao, R., Koshino, H. et al. 6,9-Dihydroxytetrangulol, a novel angucyclinone antibiotic accumulated in kiqO gene disruptant in the biosynthesis of kinanthraquinone. J Antibiot 74, 593–595 (2021). https://doi.org/10.1038/s41429-021-00442-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-021-00442-1

Search

Advanced search

Quick links