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Cytochalasins from coastal saline soil-derived fungus Aspergillus flavipes RD-13 and their cytotoxicities

The Journal of Antibiotics volume 75, pages 410–414 (2022)Cite this article

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Abstract

Chemical investigation of coastal saline soil-derived fungus Aspergillus flavipes RD-13 led to the isolation of two new seco-cytochalasins (1) and (2) along with nine known analogs. Their structures were elucidated by comprehensive spectral analysis, and the absolute configurations of these two new ones were determined through Rh2(OCOCF3)4-induced CD experiment and chemical interconversions. Moreover, the absolute configuration of a known compound named cytochalasins Z18 (3) was also determined for the first time. Structurally, compounds 1, 2 and 3 were the open ring derivatives of compounds 5, 8, and 4, respectively. All compounds were evaluated for their cytotoxic activities on A549, H1299 and H520 cells and 4 exhibited the strongest inhibitory activities towards the above cell lines with IC50 values of 0.15, 0.23 and 0.43 μg/mL, respectively. Preliminary structure-activity relationship analysis suggested the importance of macrocyclic ring in cytochalasins to confer cytotoxicity.

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References

  1. Fu P, Liu P, Qu H, Wang Y, Chen D, Wang H, et al. α-Pyrones and diketopiperazine derivatives from the marine-derived actinomycete Nocardiopsis dassonvillei HR10-5. J Nat Prod. 2011;74:2219–23.

    Article  CAS  Google Scholar 

  2. Liu D, Yan L, Ma L, Huang Y, Pan X, Liu W, et al. Diphenyl derivatives from coastal saline soil fungus Aspergillus iizukae. Arch Pharm Res. 2015;38:1038–43.

    Article  CAS  Google Scholar 

  3. Liu W, Ma L, Liu D, Huang Y, Wang C, Shi S, et al. Peniciketals A–C, New spiroketals from saline soil derived Penicillium raistrichii. Org Lett. 2014;16:90–3.

    Article  Google Scholar 

  4. Liu R, Gu Q, Zhu W, Cui C, Fan G, Fang Y, et al. 10-Phenyl-[12]-cytochalasins Z7, Z8, and Z9 from the marine-derived fungus Spicaria elegans. J Nat Prod 2006;69:871–5.

    Article  CAS  Google Scholar 

  5. Xin X, Chen Y, Zhang H, Li Y, Yang MKong L. Cytotoxic seco-cytochalasins from an endophytic Aspergillus sp. Harbored in Pinellia ternata tubers. Fitoterapia 2019;132:53–9.

    Article  CAS  Google Scholar 

  6. Orfali R, Perveen S, Khan MF, Ahmed AF, Tabassum S, Luciano P, et al. Asporychalasin, a bioactive cytochalasan with an unprecedented 6/6/11 skeleton from the Red Sea sediment Aspergillus oryzae. Phytochemistry 2021;192:112952.

    Article  CAS  Google Scholar 

  7. Scherlach K, Boettger D, Remme N, Hertweck C. The chemistry and biology of cytochalasans. Nat Prod Rep. 2010;27:869.

    Article  CAS  Google Scholar 

  8. Liu R, Lin Z, Zhu T, Fang Y, Gu Q, Zhu W. Novel open-chain cytochalsins from the marine-derived fungus Spicaria elegans. J Nat Prod. 2008;71:1127–32.

    Article  CAS  Google Scholar 

  9. Lin Z, Zhang G, Zhu T, Liu R, Wei H, Gu Q. Bioactive cytochalasins from Aspergillus flavipes, an endophytic fungus associated with the mangrove plant Acanthus ilicifolius. Helv Chim Acta. 2009;92:1538–44.

    Article  CAS  Google Scholar 

  10. Wang F, Wei H, Zhu T, Li D, Lin Z, Gu Q. Three new cytochalasins from the marine-derived fungus Spicaria elegans KLA03 by supplementing the cultures with L- and D-tryptophan. Chem Biodivers. 2011;8:887–94.

    Article  CAS  Google Scholar 

  11. Chen G, Wang H, Pei Y. Secondary metabolites from marine-derived microorganisms. J Asian Nat Prod Res. 2014;16:105–22.

    Article  CAS  Google Scholar 

  12. Zhang Q, Xiao J, Sun Q, Qin J, Pescitelli G, Gao J. Characterization of cytochalasins from the endophytic Xylaria sp. and their biological functions. J Agr Food Chem. 2014;62:10962–9.

    Article  CAS  Google Scholar 

  13. Steyn PS, van Heerden FR, Rabie CJ. Cytochalasins E and K, toxic metabolites from Aspergmus clavatus. J Chem Soc Perkin Trans. 1982;1:541–4.

    Article  Google Scholar 

  14. Wagenaar MM, Corwin J, Strobel G, Clardy J. Three new cytochalasins produced by an endophytic fungus in the Genus Rhinocladiella. J Nat Prod. 2000;63:1692–5.

    Article  CAS  Google Scholar 

  15. Zhang HW, Zhang J, Hu S, Zhang ZJ, Zhu CJ, Ng SW, et al. Ardeemins and cytochalasins from Aspergillus terreus residing in Artemisia annua. Planta Med. 2010;76:1616–21.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (81903537, 81903102 and 82173737), Natural Science Foundation of Shandong Province (ZR2018BB024 and ZR2019MC026), Traditional Chinese Medicine Technology Development Foundation of Shandong (2019-0521), Science and Technology Development Foundation of Binzhou (2015ZC0304), and Research Foundation of Binzhou Medical University (BY2015KYQD31, BY2017KJ17).

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  1. These authors contributed equally: Shuang Miao, Mengshan Liu

Authors and Affiliations

  1. Medical Research Center, Binzhou Medical University Hospital, Yellow River Second Road 661, Binzhou, 256603, China

    Shuang Miao, Mengshan Liu, Shizhou Qi, Yan Wu, Zhen Zhang, Guowei Cai & Kaikai Gong

  2. Zhejiang Provincial Engineering Technology Research Center of Marine Biomedical Products, School of Food and Pharmacy, Zhejiang Ocean University, Zhoushan, 316022, China

    Kunlai Sun

  3. Shandong Key Laboratory of Biochemical Analysis, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, 266042, China

    Kongkai Zhu

  4. Clinical Drug Trials Institution, Binzhou Medical University Hospital, Yellow River Second Road 661, Binzhou, 256603, China

    Guowei Cai

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  1. Shuang Miao
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Miao, S., Liu, M., Qi, S. et al. Cytochalasins from coastal saline soil-derived fungus Aspergillus flavipes RD-13 and their cytotoxicities. J Antibiot 75, 410–414 (2022). https://doi.org/10.1038/s41429-022-00527-5

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