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:

Three new nonenes from culture broth of marine-derived fungus Albifimbria verrucaria and their cytotoxic and anti-viral activities

Abstract

Three new nonenes, verrucanonenes A‒C (13), were isolated from culture broth of marine-derived fungus Albifimbria verrucaria. These compounds were isolated using silica gel column chromatography, reversed-phase medium pressure liquid chromatography, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were determined using a spectroscopic method. Cytotoxicities of these isolated compounds to A549, DU145, HCT116, and HT1080 cancer cell lines were assessed. Compounds 13 exhibited cytotoxicities to DU145 cancer cell line, with IC50 values of 23.4, 28.6, and 20.1 µM, respectively. Compound 2 decreased H1N1-induced cytopathic effects on MDCK cells in a dose-dependent manner.

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

Access options

Buy this article

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

Fig. 1
Fig. 2
Fig. 3

References

  1. Gilardi G, Matic S, Luongo I, Gullino ML, Garibaldi A. First report of stem necrosis and leaf spot of tomato caused by Albifimbria verrucaria in Italy. Plant Dis. 2020;104:2026.

    Article  Google Scholar 

  2. Chen Y, Ran SF, Dai DQ, Wang Y, Hyde KD, Wu YM, et al. Mycosphere essays 2. Myrothecium. Mycosphere. 2016;7:64–80.

    Article  CAS  Google Scholar 

  3. Zhang CC, Ding SS, Shi WS, Cao F, Zhu HJ, Wen ML. A new quinolinone from freshwater lake-derived fungus Myrothecium verrucaria. Nat Prod Res. 2017;31:99–103.

    Article  CAS  PubMed  Google Scholar 

  4. Zou XW, Niu SB, Ren JW, Li EW, Liu XZ, Che YS. Verrucamides A–D, antibacterial cyclopeptides from Myrothecium verrucaria. J Nat Prod. 2011;74:1111–6.

    Article  CAS  PubMed  Google Scholar 

  5. Nguyen MV, Han JW, Kim H, Choi GJ. Curvicollide D, a new modified γ-lactone from the culture broth of Albifimbria verrucaria and its antifungal activity against plant pathogenic fungi. J Antibiot. 2022;75:514–8.

    Article  CAS  Google Scholar 

  6. Fang ST, Song YP, Miao FP, Yin XL, Ji NY. Myrochromanol analogues and trichothecene derivatives from the shellfish-derived fungus Albifimbria verrucaria. Phytochemistry. 2023;209:113645.

    Article  CAS  PubMed  Google Scholar 

  7. Nguyen LTT, Jang JY, Kim TY, Yu NH, Park AR, Lee S, et al. Nematicidal activity of verrucarin A and roridin A isolated from Myrothecium verrucaria against Meloidogyne incognita. Pestic Biochem Physiol. 2018;148:133–43.

    Article  CAS  PubMed  Google Scholar 

  8. de Carvalho MP, Weich H, Abraham WR. Macrocyclic trichothecenes as antifungal and anticancer compounds. Curr Med Chem. 2016;23:23–35.

    Article  PubMed  Google Scholar 

  9. Liu L, Tang MX, Sang XN, Chen SF, Lu XJ, Wang YB, et al. Three new tetralol analogs from soil-derived fungus Myrothecium verrucaria with anti-inflammatory activity. J Asian Nat Prod Res. 2019;21:33–42.

    Article  CAS  PubMed  Google Scholar 

  10. Hoshino S, Ozeki M, Wong CP, Zhang H, Hayashi F, Awakawa T, et al. Mirilactams C–E, Novel polycyclic macrolactams isolated from combined-culture of Actinosynnema mirum NBRC 14064 and mycolic acid-containing bacterium. Chem Pharm Bull. 2018;66:660–7.

    Article  CAS  Google Scholar 

  11. Lim HJ, Bae J, Bak SG, Chandimali N, Park EH, Park SI, et al. Limocitrin Suppresses Breast Cancer Through Inducing Apoptotic-Cell Death Signaling and Inhibiting the PI3K/AKT/mTOR/S6K Cell Survival Signaling. J Med Food. 2023;26:749–59.

    Article  CAS  Google Scholar 

  12. Nguyen NH, Ha TKQ, Choi S, Eum S, Lee CH, Bach TT, et al. Chemical constituents from Melicope pteleifolia leaves. Phytochemistry. 2016;130:291–300.

    Article  CAS  PubMed  Google Scholar 

  13. Lee BW, Ha TKQ, Cho HM, An JP, Kim SK, Kim CS, et al. Antiviral activity of furanocoumarins isolated from Angelica dahurica against influenza a viruses H1N1 and H9N2. J Ethnopharmacol. 2020;259:112945.

    Article  CAS  PubMed  Google Scholar 

  14. Bang S, Li W, Ha TKQ, Lee C, Oh WK, Shim SH. Anti-influenza effect of the major flavonoids from Salvia plebeia R.Br. via inhibition of influenza H1N1 virus neuraminidase. Nat Prod Res. 2018;32:1224–8.

    Article  CAS  PubMed  Google Scholar 

  15. Dai WJ, Wu J, Han Z, Mei WL, Dai HF. Metabolites from endophytic fungus S20 of Cephalotaxus hainanensis. J Asian Nat Prod Res. 2009;11:704–9.

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF-2021R1A2C1094267) and the authors thank Ms. Ji-Young Oh, Center for University-wide Research Facilities (CURF) at Jeonbuk National University, for performing NMR measurements.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to In-Kyoung Lee or Bong-Sik Yun.

Ethics declarations

Conflict of interest

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

Kim, YH., Choi, DC., Ki, DW. et al. Three new nonenes from culture broth of marine-derived fungus Albifimbria verrucaria and their cytotoxic and anti-viral activities. J Antibiot (2024). https://doi.org/10.1038/s41429-024-00735-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1038/s41429-024-00735-1

Search

Quick links