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.

  • Article
  • Published:

Pestalotinones A–D, new benzophenone antibiotics from endophytic fungus Pestalotiopsis trachicarpicola SC-J551

The Journal of Antibiotics volume 75, pages 207–212 (2022)Cite this article

Subjects

Abstract

Four new pestalone-type benzophenones, pestalotinones A–D (1−4), along with six known congeners, pestalone, pestalone E–F, SB87-Cl, SB87-H, and pestalachloride B, were isolated from the endophytic fungus Pestalotiopsis trachicarpicola SC-J551 cultivated on rice grains. Their structures were established by extensive spectroscopic analysis. Compounds 1−3 exhibited potent activity against Staphylococcus aureus and MRSA (MIC: 1.25–2.5 μg ml−1) while no cytotoxicity against Vero cells (IC50 > 50 μM). The activity profile of this group of compounds suggested that replacement of the C-14 aldehyde with an oxymethyl greatly increases their activity and selectivity towards the bacteria and chlorine substitutions result in the increase of antibacterial activity and slight decrease of cytotoxicity against the mammalian cells.

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

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

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

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Cueto M, Jensen PR, Kauffman C, Fenical W, Lobkovsky E, Clardy J. Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. J Nat Prod. 2001;64:1444–6.

    Article  CAS  Google Scholar 

  2. Li E, Jiang L, Guo L, Zhang H, Che Y. Pestalachlorides A-C, antifungual metabolites from the plant endophytic fungus Pestalotiopsis adusta. Bioorg Med Chem. 2008;16:7894–9.

    Article  CAS  Google Scholar 

  3. Wei MY, Li D, Shao CL, Deng DS, Wang CY. (±)-Pestalachloride D, an antibacterial racemate of chlorinated benzophenone derivative from a soft coral-derived fungus Pestalotiopsis sp. Mar Drug. 2013;11:1050–60.

    Article  CAS  Google Scholar 

  4. Xing Q, Gan LS, Mou XF, Wang W, Wang CY, Wei MY, et al. Isolation, resolution and biological evaluation of pestalachlorides E and F containing both point and axial chirality. RSC Adv. 2016;6:22653–8.

    Article  CAS  Google Scholar 

  5. Song RY, Liu Y, Liu RH, Wang XB, Li TX, Kong LY, et al. Benzophenone derivatives from the plant endophytic fungus, Pestalotiopsis sp. Phyto Lett. 2017;22:189–93.

    Article  CAS  Google Scholar 

  6. Wang W, Park C, Oh E, Sung Y, Lee J, Park KH, et al. Benzophenone compounds, from a marine-derived strain of the fungus Pestalotiopsis neglecta, inhibit proliferation of pancreatic cancer cells by targeting the MEK/ERK pathway. J Nat Prod. 2019;82:3357–65.

    Article  CAS  Google Scholar 

  7. Lei H, Niu H, Song C, Fu X, Luo Y, Chen S, et al. Chlorinated benzophenone derivatives as chemotaxonomic markers for the genus of Pestalotiopsis. Biochem Syst Ecol. 2020;91:104072.

    Article  CAS  Google Scholar 

  8. Wachi Y, Yamashita T, Komatsu K, Yoshida S. JP Patent JKXXAF JP 07061950 A2 19950307, 1995.

  9. Slavov N, Cvengroš J, Neudӧfrl J-M, Schmalz H-G. Total synthesis of the marine antibiotic pestalone and its surprisingly facile conversion into pestalalactone and pestalachloride. A. Angew Chem Int Ed. 2010;49:7588–91.

    Article  CAS  Google Scholar 

  10. Augner D, Krut O, Slavov N, Gerbino DC, Sahl H-G, Benting J, et al. On the Antibiotic and antifungal activity of pestalone, pestalachloride A, and structurally related compounds. J Nat Prod. 2013;76:1519–22.

    Article  CAS  Google Scholar 

  11. Wezeman T, Bräse S, Masters K-S. Xanthone dimers: a compound family which is both common and privileged. Nat Prod Rep. 2015;32:6–28.

    Article  CAS  Google Scholar 

  12. Fu Y, Wu P, Xue J, Wei X. Cytotoxic and antibacterial quinone sesquiterpenes from a Myrothecium Fungus. J Nat Prod. 2014;77:1791–9.

    Article  CAS  Google Scholar 

  13. Shi J-F, Wu P, Jiang Z-H, Wei X-Y. Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. Eur J Med Chem. 2014;71:219–28.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank Prof. Songzhen Yang, Guangdong Institute of Microbiology, for morphological authentication of the producing actinomycete, Mr. Yunfei Yuan, South China Botanical Garden, Chinese Academy of Sciences, for NMR spectroscopic measurements, Ms. Aijun Sun, South China Sea Institute of Oceanology, Chinese Academy of Sciences, for HRESIMS measurements, and Mr. Kang Liao, The First Affiliate Hospital, Sun Yat-sen University, for providing the drug-resistant bacteria, VRE and VSE.

Funding

This work was supported by NSFC grants (Nos. 81872773 and 82073732).

Author information

Authors and Affiliations

  1. Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Xingke Road 723, Tianhe District, Guangzhou, 510650, People’s Republic of China

    Zhiming Jiang, Ping Wu, Hanxiang Li, Jinghua Xue & Xiaoyi Wei

  2. School of Life Sciences, University of Chinese Academy of Sciences, Yuquanlu 19A, Beijing, 100049, People’s Republic of China

    Zhiming Jiang

Authors
  1. Zhiming Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ping Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hanxiang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jinghua Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xiaoyi Wei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ping Wu.

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

Jiang, Z., Wu, P., Li, H. et al. Pestalotinones A–D, new benzophenone antibiotics from endophytic fungus Pestalotiopsis trachicarpicola SC-J551. J Antibiot 75, 207–212 (2022). https://doi.org/10.1038/s41429-022-00510-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-022-00510-0

This article is cited by

Search

Advanced search

Quick links