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Antibacterial angucyclinone and α-pyrone derivatives from desert-derived Nocardiopsis dassonvillei HDN 154151

Abstract

One new angucyclinone derivative, Kanglemycin N (1), and two new biogenetically related α-Pyrones, nocapyrones U-V (2–3), were isolated from a desert-derived Actinomycete Nocardiopsis dassonvillei HDN 154151. Their structures, including absolute configurations, were elucidated by extensive NMR, MS, and ECD analyses. Compound 1 exhibited potent antibacterial activity against Bacillus subtilis, Proteus sp., Vibrio Parahaemolyticus, Escherichia coli and Methicillin-resistant Staphylococcus aureus (MRSA) with MIC values ranging from 0.39 μM to 1.56 μM, and notably the effect of 1 against MRSA significantly exceeded the positive control ciprofloxacin. In addition, compound 1 also showed moderate cytotoxic activity against H69AR, MDA-MB-231, ASPC-1 and K562 cell lines, with IC50 values of 10.46, 8.78, 9.28 and 8.61 μM, respectively.

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References

  1. Meyer J. Nocardiopsis, a new genus of the order Actinomycetales. Int J Syst Bacteriol. 1976;26:487–93.

    Article  Google Scholar 

  2. Genilloud O. Actinomycetes: still a source of novel antibiotics. Nat Prod Rep. 2017;34:1203–32.

    Article  CAS  Google Scholar 

  3. Fu P, Liu P, Qu H, Wang Y, Chen D, Wang H, Li J, Zhu W. Alpha-pyrones and diketopiperazine derivatives from the marine-derived actinomycete Nocardiopsis dassonvillei HR10-5. J Nat Prod. 2011;74:2219–23.

    Article  CAS  Google Scholar 

  4. Hiroshi T. Isolation of cytotoxic substance, kalafungin from an alkalophilic actinomycete, Nocardiopsis dassonvillei subsp. presina. Chem Pharm Bull. 1990;38:2299–2300.

    Article  Google Scholar 

  5. Chen HL, Wan CX, Zhang LL. A new diketopiperazine isolated from a Nocardiopsis strain TRM20105 guided by bioassay against Candida albicans. Nat Prod Res. 2019;33:3421–5.

    Article  CAS  Google Scholar 

  6. Tanida S, Takizawa M, Takahashi T, Tsubotani S, Harada S. TAN-999 and TAN-1030A, new indolocarbazole alkloids with macrophage-activting properties. J Antibiot. 1989;42:1619–30.

    Article  CAS  Google Scholar 

  7. Chang Y, Che Q, Xing L, Ma C, Han Y, Zhu T, Pfeifer BA, Peng J, Zhang G, Li D. Antibacterial p-Terphenyl with a rare 2,2’-Bithiazole substructure and related compounds isolated from the marine-derived actinomycete Nocardiopsis sp. HDN154086. J Nat Prod. 2021;84:1226–31.

    Article  CAS  Google Scholar 

  8. Zhao T, Chang Y, Zhu T, Li J, Gu Q, Li D, Che Q, Zhang G. alpha-Pyrone derivatives with cyto-protective activity from two Takla Makan desert soil derived actinomycete Nocardiopsis strains recovered in seawater based medium. Nat Prod Res. 2019;33:2498–506.

    Article  CAS  Google Scholar 

  9. Wang JX, Sun CX, Shah M, Zhang GJ, Gu QQ, Zhu TJ, Che Q, Li DH. New metabolites from a Mariana Trench-derived actinomycete Nocardiopsis sp. HDN 17-237. J Asian Nat Prod Res. 2020;22:1031–6.

    Article  CAS  Google Scholar 

  10. Zhou J, Sun C, Wang N, Gao R, Bai S, Zheng H, You X, Li R. Preliminary report on the biological effects of space flight on the producing strain of a new immunosuppressant, Kanglemycin C. J Ind Microbiol Biotechnol. 2006;33:707–12.

    Article  CAS  Google Scholar 

  11. Vanga DC, Kaliappan KP. A unified strategy for the syntheses of angucyclinone antibiotics: total syntheses of Tetrangulol, Kanglemycin M, X-14881-E, and Anhydrolandomycinone. Eur J Org Chem. 2012;2012:2250–9.

    Article  CAS  Google Scholar 

  12. Zhang H, Saurav K, Yu Z, Mándi A, Kurtán T, Li J, Tian X, Zhang Q, Zhang W, Zhang C. alpha-Pyrones with diverse hydroxy substitutions from three marine-derived Nocardiopsis strains. J Nat Prod. 2016;79:1610–8.

    Article  CAS  Google Scholar 

  13. Elnaggar MS, Ebada SS, Ashour ML, Ebrahim W, Muller WEG, Mandi A, Kurtan T, Singab A, Lin W, Liu Z, Proksch P. Xanthones and sesquiterpene derivatives from a marine-derived fungus Scopulariopsis sp. Tetrahedron 2016;72:2411–9.

    Article  CAS  Google Scholar 

  14. Xu D, Nepal KK, Chen J, Harmody D, Zhu H, McCarthy PJ, Wright AE, Wang G. Nocardiopsistins A-C: new angucyclines with anti-MRSA activity isolated from a marine sponge-derived Nocardiopsis sp. HB-J378. Synth Syst Biotechnol. 2018;3:246–51.

    Article  Google Scholar 

  15. Sun CH, Wang Y, Wang Z, Zhou JQ, Jin WZ, You XF, Gao H, Zhao LX, Si SY, Li X. Chemomicin A, a new angucyclinone antibiotic produced by Nocardia mediterranei subsp. kanglensis 1747-64. J Antibiot. 2007;60:211–5.

    Article  CAS  Google Scholar 

  16. Jiang X, Zhang Q, Zhu Y, Nie F, Wu Z, Yang C, Zhang L, Tian X, Zhang C. 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 

  17. Andrews JM. Determination of minimum inhibitory concentrations. J Antimicrob Chemother. 2002;49:1049–1049.

    Article  Google Scholar 

  18. Pierce CG, Uppuluri P, Tristan AR, Wormley FL, Mowat E, Ramage G, Lopez-Ribot JL. A simple and reproducible 96-well plate-based method for the formation of fungal biofilms and its application to antifungal susceptibility testing. Nat Protoc. 2008;3:1494–1500.

    Article  CAS  Google Scholar 

  19. Alley MC, Scudiero DA, Monks A, Hursey ML, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker RH, Boyd MR. Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay. Cancer Res. 1988;48:589–601.

    CAS  PubMed  Google Scholar 

  20. Scudiero DA, Shoemaker RH, Paull KD, Monks A, Tierney S, Nofziger TH, Currens MJ, Seniff D, Boyd MR. Evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 1988;48:4827–33.

    CAS  PubMed  Google Scholar 

  21. Vichai V, Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc. 2006;1:1112–6.

    Article  CAS  Google Scholar 

  22. Halgren TA. MMFF VII. Characterization of MMFF94, MMFF94s, and other widely available force fields for conformational energies and for intermolecular-interaction energies and geometries. J Comput Chem. 1999;20:730–48.

    Article  CAS  Google Scholar 

  23. Jacquemin D, Wathelet V, Perpe TEA, Adamo C. Extensive TD-DFT benchmark: singlet-excited states of organic molecules. J Chem Theory Comput. 2009;5:2420–35.

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by National Natural Science Foundation of China (41976105, 81991522, 81973234, U1906212), the Fundamental Research Funds for the Central Universities (201941001, 202042005), the Marine S&T Fund of Shandong Province for Pilot National Laboratory for Marine Science and Technology (Qingdao) (2018SDKJ0401-2) and Taishan Scholar Youth Expert Program in Shandong Province (tsqn201812021, 202103153), Shandong Provincial Natural Science Foundation (ZR20119ZD18, 2019KJM004).

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Correspondence to Dehai Li or Guojian Zhang.

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Tang, Z., Chang, Y., Zhu, T. et al. Antibacterial angucyclinone and α-pyrone derivatives from desert-derived Nocardiopsis dassonvillei HDN 154151. J Antibiot 75, 380–384 (2022). https://doi.org/10.1038/s41429-022-00526-6

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