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Geninthiocins E and F, two new cyclic thiopeptides with antiviral activities from soil-derived Streptomyces sp. CPCC 200267 using OSMAC strategy

The Journal of Antibiotics volume 76, pages 101–104 (2023)Cite this article

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Abstract

On the basis of the one strain-many compounds (OSMAC) strategy, two new cyclic thiopeptides, geninthiocins E and F, together with four known geninthiocin derivatives, geninthiocins A, B, C, and val-geninthiocin were isolated from Streptomyces sp. CPCC 200267. Their structures and absolute configurations were elucidated by extensive spectroscopic analyses and Marfey’s method. Geninthiocin E (1), val-geninthiocin (3), geninthiocin A (4), and geninthiocin B (5) exhibited significant anti-influenza A virus activities with the IC50 values of 28.7, 15.3, 7.3, and 18.3 μM, respectively. Compounds 3 and 4 showed moderate antibacterial activities against Staphylococcus aureus.

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References

  1. Shen X, Mustafa M, Chen Y, Gao Y, Gao J. Natural thiopeptides as a privileged scaffold for drug discovery and therapeutic development. Med Chem Res. 2019;28:1063–98.

    Article  CAS  Google Scholar 

  2. Kohno J, Kameda N, Nishio M, Kinumaki A, Komatsubara K. The structures of sulfomycins II and III. J Antibiot. 1996;49:1063–5.

    Article  CAS  Google Scholar 

  3. Mukai A, Fukai T, Hoshino Y, Yazawa K, Harada KI, Mikami Y. Nocardithiocin, a novel thiopeptide antibiotic, produced by pathogenic Nocardia pseudobrasiliensis IFM 0757. J Antibiot. 2009;62:613–9.

    Article  CAS  Google Scholar 

  4. Puar MS, Chan TM, Hegde V, Patel M, Bartner P, Ng KJ, Pramanik BN, MacFarlane RD. Sch 40832: a novel thiostrepton from Micromonospora carbonacea. J Antibiot. 1998;51:221–4.

    Article  CAS  Google Scholar 

  5. Rogers MJ, Cundliffe E, McCutchan TF. The antibiotic micrococcin is a potent inhibitor of growth and protein synthesis in the malaria parasite. Antimicrob Agents Chemother. 1998;42:715–6.

    Article  CAS  Google Scholar 

  6. Zhang C, Occi J, Masurekar P, Barrett JF, Zink DL, Smith S, Onishi R, Ha S, Salazar O, Genilloud O, Basilio A, Vicente F, Gill C, Hickey EJ, Dorso K, Motyl M, Singh SB. Isolation, structure, and antibacterial activity of philipimycin, a thiazolyl peptide discovered from Actinoplanes philippinensis MA7347. J Am Chem Soc. 2008;130:12102–10.

    Article  CAS  Google Scholar 

  7. Zhang C, Herath K, Jayasuriya H, Ondeyka JG, Zink DL, Occi J, Birdsall G, Venugopal J, Ushio M, Burgess B, Masurekar P, Barrett JF, Singh SB. Thiazomycins, thiazolyl peptide antibiotics from Amycolatopsis fastidiosa. J Nat Prod. 2009;72:841–7.

    Article  CAS  Google Scholar 

  8. Del Carratore F, Iorio M, Pérez-Bonilla M, Schmidt K, Pérez-Redondo R, Sosio M, Macdonald SJ, Gyulev IS, Tsigkinopoulou A, Thomas GH, Genilloud O, Rodríguez-García A, Donadio S, Breitling R, Takano E. Multi-omics study of Planobispora rosea, producer of the thiopeptide antibiotic GE2270A. mSystems. 2021;6:e0034121.

    Article  Google Scholar 

  9. Bagley MC, Dale JW, Merritt EA, Xiong X. Thiopeptide antibiotics. Chem Rev. 2005;105:685–714.

    Article  CAS  Google Scholar 

  10. Vinogradov AA, Suga H. Introduction to thiopeptides: biological activity, biosynthesis, and strategies for functional reprogramming. Cell Chem Biol. 2020;27:1032–51.

    Article  CAS  Google Scholar 

  11. Bowers AA, Walsh CT, Acker MG. Genetic interception and structural characterization of thiopeptide cyclization precursors from Bacillus cereus. J Am Chem Soc. 2010;132:12182–4.

    Article  CAS  Google Scholar 

  12. Li S, Hu X, Li L, Liu H, Yu L, You X, Jiang B, Wu L. Geninthiocins C and D from Streptomyces as 35-membered macrocyclic thiopeptides with modified tail moiety. J Antibiot. 2019;72:106–10.

    Article  CAS  Google Scholar 

  13. Zhang D, Wang Y, Hu X, Wang X, Li L, Gu G, Zhang B, Cen S, You X, Yu L. Cyclic and linear thiopeptides from soil-derived Streptomyces sp. CPCC 203702 with antiviral and antibacterial activities. Chin J Chem. 2021;39:3277–84.

    Article  CAS  Google Scholar 

  14. Vijayasarathy S, Prasad P, Fremlin LJ, Ratnayake R, Salim AA, Khalil Z, Capon RJ. C3 and 2D C3 Marfey’s methods for amino acid analysis in natural products. J Nat Prod. 2016;79:421–7.

    Article  CAS  Google Scholar 

  15. Sajid I, Shaaban KA, Frauendorf H, Hasnain S, Laatsch H. Val-geninthiocin: structure elucidation and MSn fragmentation of thiopeptide antibiotics produced by Streptomyces sp. RSF18 Z Naturforsch B. 2008;63b:1223–30.

    Article  Google Scholar 

  16. Schneider O, Simic N, Aachmann FL, Aachmann FL, Rückert C, Kristiansen KA, Kalinowski J, Jiang Y, Wang L, Jiang CL, Lake R, Zotchev SB. Genome mining of Streptomyces sp. YIM 130001 isolated from lichen affords new thiopeptide antibiotic. Front Microbiol. 2018;9:3139.

    Article  Google Scholar 

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Acknowledgements

The authors thank the mass spectrometry facility of National Center for Protein Sciences at Peking University and Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College for assistance with NMR spectrometer and Dr. Xiaogang Niu for help with NMR spectroscopic data analyses.

Funding

The work was financially supported by the National Natural Science Foundation of China (82073744), CAMS Innovation Fund for Medical Sciences (2021-I2M-1-055), the Non-profit Central Research Institute Fund of CAMS (2021-PT350-001), and the National Microbial Resource Center (No. NMRC-2022-3).

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Authors and Affiliations

  1. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China

    Yuan Fang, Jing Wang, Yan Tang, Zhe Guo, Jinglin Bai, Linzhuan Wu, Jing Su, Shan Cen, Liyan Yu & Dewu Zhang

  2. School of Pharmacy, Yantai University, Yantai, China

    Yan Tang

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  1. Yuan Fang
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Correspondence to Liyan Yu or Dewu Zhang.

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Fang, Y., Wang, J., Tang, Y. et al. Geninthiocins E and F, two new cyclic thiopeptides with antiviral activities from soil-derived Streptomyces sp. CPCC 200267 using OSMAC strategy. J Antibiot 76, 101–104 (2023). https://doi.org/10.1038/s41429-022-00580-0

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