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Hygromycin A derivatives isolated from Streptomyces sp. PC-22 in the rhizosphere soil of Pulsatilla chinensis

Abstract

On the basis of the one strain-many compounds (OSMAC) strategy, two new hygromycin A derivatives (3, 4), together with six known compounds were isolated from a medicinal plant inter rhizospheric Streptomyces in Pulsatilla chinensis. The structures of 3 and 4 were elucidated using NMR and HRESIMS analyses. A plausible biosynthetic pathway for these compounds was discussed. All the compounds were evaluated for their antimicrobial and cytotoxic activities. Compound 5 exhibited potent inhibitory activity against S. aureus and B. subtilis with the MICs of 16 and 8 μg ml−1, while 4 showed weak inhibitory activity against S. aureus.

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References

  1. Zhang HW, Song YC, Tan RX. Biology and chemistry of endophytes. Nat Prod Rep. 2006;23:753–71.

    Article  CAS  Google Scholar 

  2. Strobel G, Daisy B, Castillo U, Harper J. Natural products from endophytic microorganisms. J Nat prod. 2004;67:257–68.

    Article  CAS  Google Scholar 

  3. Feng QM, Yu Y, Tang MX, Zhang TY, Zhang MY, Wang HF, et al. Four new hybrid polyketide-terpenoid metabolites from the Penicillium sp. SYPF7381 in the rhizosphere soil of Pulsatilla chinensis. Fitoterapia. 2018;125:249–57.

    Article  CAS  Google Scholar 

  4. Zhao HM, Yang AP, Zhang N, Li SY, Yuan TJ, Ding N, et al. Insecticidal endostemonines A−J produced by endophytic Streptomyces from Stemona sessilifolia. J Agric Food Chem. 2020;68:1588–95.

    Article  CAS  Google Scholar 

  5. Zhao HM, Yang AP, Liu J, Bao S, Peng R, Hu Y, et al. Chartspiroton, a tetracyclic spiro-naphthoquinone derivative from a medicinal plant endophytic Streptomyces. Org Lett. 2020;22:3739–43.

    Article  CAS  Google Scholar 

  6. Li YH, Zou M, Han Q, Deng LR, Weinshilboum RM. Therapeutic potential of triterpenoid saponin anemoside B4 from Pulsatilla chinensis. Pharm Res. 2020;160:105079.

    Article  CAS  Google Scholar 

  7. Palaniappan N, Dhote V, Ayers S, Starosta AL, Wilson DN, Reynolds KA, et al. Biosynthesis of the aminocyclitol subunit of hygromycin A in Streptomyces hygroscopicus NRRL 2388. Chem Biol. 2009;16:1180–9.

    Article  CAS  Google Scholar 

  8. Mann RL, Gale RM, Van Abeele RF. Hygromycin. II. isolation and properties. Antibiot Chemother (Northfield). 1953;3:1279–82.

    CAS  Google Scholar 

  9. Nakagawa A, Fujimoto T, Omura S, Walsh JC, Stotish RL, George B. Hygromycin A, an antitreponemal substance. II. therapeutic effect for swine dysentery. J Antibiot. 1987;40:1627–35.

    Article  CAS  Google Scholar 

  10. Hayashi SF, Norcia L, Seibel SB, Silvia A. Structure-activity relationships of hygromycin A and its analogs: protein synthesis inhibition activity in a cell free system. J Antibiot. 1997;50:514–21.

    Article  CAS  Google Scholar 

  11. Jaynes BH, Cooper CB, Hecker SJ, Blair KT, Elliott NC, Lilley SC, et al. Synthesis and vitro antibacterial activity of hygromycin A analogs modified at the C4′ aryl position. Bioorg Med Chem Lett. 1993;3:1531–6.

    Article  CAS  Google Scholar 

  12. Rateb ME, Houssen WE, Harrison WTA, Deng H, Okoro CK, Asenjo JA, et al. Diverse metabolic profiles of a Streptomyces strain isolated from a hyper-arid environment. J Nat Prod. 2011;74:1965–71.

    Article  CAS  Google Scholar 

  13. Wakisaka Y, Koizumi K, Nishimoto Y, Kobayashi M, Tsuji N. Hygromycin and epihygromycin from a bacterium, Corynebacterium equi No. 2841. J Antibiot. 1980;33:695–704.

    Article  CAS  Google Scholar 

  14. Yoshida M, Takahashi E, Uozumi T, Beppu T. Hygromycin A and methoxyhygromycin, novel inhibitors of K88 antigen synthesis of enterotoxic Escherichia coli strain. Agric Biol Chem. 1986;50:143–9.

    CAS  Google Scholar 

  15. Palaniappan N, Ayers S, Gupta S, Habib ES, Reynoldset KA. Production of hygromycin A analogs in Streptomyces hygroscopicus NRRL 2388 through identification and manipulation of the biosynthetic gene cluster. Chem Biol. 2006;13:753–64.

    Article  CAS  Google Scholar 

  16. Wang XC, Reynolds AR, Elshahawi SI, Shaaban KA, Ponomareva LV, Saunders MA, et al. Terfestatins B and C, new p-terphenyl glycosides produced by Streptomyces sp. RM-5-8. Org Lett. 2015;17:2796–9.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation (81803391), the Natural Science Foundation of Jiangsu (BK20180828), Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province (ARRLKF21-01), Jiangsu Provincial “Double Creation Talent Program” (202010528) and the Natural Science Foundation Youth Program of Nanjing University of Chinese Medicine (NZY81803391).

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Correspondence to Xiao Liu, Yang Hu or Lihong Hu.

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Ding, X., Yuan, T., Chen, W. et al. Hygromycin A derivatives isolated from Streptomyces sp. PC-22 in the rhizosphere soil of Pulsatilla chinensis. J Antibiot 75, 176–180 (2022). https://doi.org/10.1038/s41429-022-00506-w

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