Skip to main content

Advertisement

Log in

Epoxyquinophomopsins A and B from endophytic fungus Phomopsis sp. and their activity against tyrosine kinase

  • Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

Abstract

Two new quinone derivatives, epoxyquinophomopsins A (1) and B (2), were purified from the EtOAc extract of endophytic fungus Phomopsis sp isolated from Morus cathayana. The structures of both compounds were determined based on 1D and 2D NMR and mass spectral data, as well as by x-ray diffraction analysis for 1. Compounds 1 and 2 were screened against eight receptor- (RTKs) and eight non-receptor tyrosine kinases (nRTKs). Both compounds showed strong inhibitory properties against Bruton’s Tyrosine Kinase (nRTK) with their kinase activity were 19% and 20%, respectively. Only compound 1 that showed strong inhibitory properties against RTKs EGFR and HER-4 with its kinase activity were 16 and 15%, respectively. Thus, both compounds have potential as tyrosine kinase inhibitors.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

References

  1. Yu JS (2019) From discovery of tyrosine phosphorylation to targeted cancer therapies: the 2018 tang prize in biopharmaceutical science. Biomed J 42:80–83

    Article  Google Scholar 

  2. Ségaliny AI, Tellez-Gabriel M, Heyman M-F (2015) Receptor tyrosine kinases: characterisation, mechanism of action and therapeutic interests for bone cancers. J Bone Oncol 4:1–12

    Article  Google Scholar 

  3. Gocek E, Moulas AN, Studzinski GP (2014) Non-receptor protein tyrosine kinases signaling pathways in normal and cancer cells. Crit Rev Clin Lab Sci 51:125–137

    Article  CAS  Google Scholar 

  4. Jiao Q, Bi L, Ren Y, Song S, Wang Q, Wang Y-S (2018) Advances in studies of tyrosine kinase inhibitors and their acquired resistance. Mol Cancer 17:36

    Article  Google Scholar 

  5. Hermawati E, Juliawaty LD, Hakim EH (2017) A quinone derivative from an endophytic fungus Phomopsis sp. from Morus cathayana. Rec Nat Prod 11:315–317

    CAS  Google Scholar 

  6. Piggott MJ (2005) Naphtho[2,3-c]furan-4,9-diones and related compounds: theoretically interesting and bioactive natural and synthetic products. Tetrahedron 61:9929–9954

    Article  CAS  Google Scholar 

  7. Qian-Cutrone J, Gao Q, Huang S, Klohr SE, Veitch JA, Shu Y-Z (1994) Arthrinone, a novel fungal metabolite from Arthrinium sp. FA 1744. J Nat Prod 57:1656–1660

    Article  CAS  Google Scholar 

  8. Whyte AC, Gloer KB, Gloer JB, Koster B, Malloch D (2017) New antifungal metabolites from the coprophilous fungus Cercophora sordariodes. Can J Chem 75:768–772

    Article  Google Scholar 

  9. Pearson M, García-Echeverría C, Fabbro D (2006) Protein tyrosine kinases as targets for cancer. In: Fabbro D, McCormick F (eds) Protein tyrosine kinase: from inhibitors to useful drugs. Humana Press Inc., Totowa New Jersey, pp 1–30

    Google Scholar 

  10. Russo A, Paret C, Alt F, Burhenne J, Fresnais M, Wagner W, Glaser M, Bender H, Huprich S, Harter PN, Filipski K, Lehmann N, Backes N, Roth L, Seidmann L, Sommer C, Brockmann MA, Pietsch T, Neu MA, Wingerter A, Faber J (2019) Ceritinib-induced regression of an insulin-like growth factor-driven neuroepithelial brain tumor. Int J Mol Sci 20:4267. https://doi.org/10.3390/ijms20174267

  11. Dobrovolsky D, Wang ES, Morrow S, Leahy C, Faust T, Nowak RP, Donovan KA, Yang G, Li Z, Fischer ES, Treon SP, Weinstock DM, Gray NS (2019) Bruton tyrosine kinase degradation as a therapeutic strategy for cancer. Blood 133:952–961

    Article  CAS  Google Scholar 

  12. Zhang J, Yang PL, Gray NS (2009) Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 9:28–39

    Article  Google Scholar 

  13. Yin B, Fang D-M, Zhou X-L, Gao F (2019) Natural products as important tyrosine kinase inhibitors. Eur J Med Chem 182:111664

    Article  CAS  Google Scholar 

  14. Kawakami Y, HArtman SE, Kinoshita E, Suzuki H, Kitaura J, Yao L, Inagaki N, Franco A, Hata D, Maeda-Yamamoto M, Fukamachi H, Nagai R, Kawakami T (1999) Terreic acid, a quinone epoxide inhibitor of Bruton’s tyrosine kinase. Proc Natl Acad Sci. USA 96:2227–2232

    Article  CAS  Google Scholar 

  15. White TJ, Bruns T, Lee S, Taylor J (1990) Amplification and direct sequencing of fungal Ribosomal RNA genes for phylogenetics. PCR Protocols: a guide to methods and applications. Academic Press, San Diego, pp 315–322

    Google Scholar 

  16. Hennek J, Alves J, Yao E, Goueli SA, Zegzouti H (2016) Bioluminescent kinase strips: a novel approach to targeted and flexible kinase inhibitor profiling. Anal Biochem 495:9–20

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We acknowledge the Grant of P3MI 2020, Institut Teknologi Bandung, for financial support to this research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Elvira Hermawati.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 961 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hermawati, E., Ellita, S.D., Juliawaty, L.D. et al. Epoxyquinophomopsins A and B from endophytic fungus Phomopsis sp. and their activity against tyrosine kinase. J Nat Med 75, 217–222 (2021). https://doi.org/10.1007/s11418-020-01454-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-020-01454-1

Keywords

Navigation