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:

Terphenyl derivatives and terpenoids from a wheat-born mold Aspergillus candidus

The Journal of Antibiotics volume 73, pages 189–193 (2020)Cite this article

Subjects

Abstract

A new p-terphenyl derivative aspergicandidusin A (1), a new cleistanthane diterpenoid 6-deoxyaspergiloid C (13), and 12 known compounds (2−12, and 14) were isolated from the mold Aspergillus candidus. The structures of the new compounds were elucidated by spectral analysis of NMR and MS data. The absolute configuration of C-1 in 13 was determined via the circular dichroism data of the [Rh2(OCOCF3)4] complex. Compounds 2−8 and 11 showed moderate inhibitory activity against K562 cell lines with the IC50 value in the range from 17.9 to 46.3 μM. Compound 13 exhibited moderate cytotoxicity against HepG2 cells with the IC50 value of 47.7 μM. Compounds 11 and 12 exhibited moderate activity against the growth of S. aureus with MIC value of 6.25 μM, respectively.

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

References

  1. Gonçalves A, et al. Pre- and postharvest strategies to minimize mycotoxin contamination in the rice food chain. Compr Rev Food Sci Food Saf. 2019. https://doi.org/10.1111/1541-4337.12420.

    Article  Google Scholar 

  2. Fredlund E, et al. Moulds and mycotoxins in rice from the Swedish retail market. Food Addit Contam Part A. 2009;26:527–33.

    Article  CAS  Google Scholar 

  3. Park JW, Choi SY, Hwang HJ, Kim YB. Fungal mycoflora and mycotoxins in Korean polished rice destined for humans. Int J Food Microbiol. 2005;103:305–14.

    Article  CAS  Google Scholar 

  4. Barron GL, Lichtwardt RW. Quantitative estimations of the fungi associated with deterioration of stored corn in Iowa. Iowa State J Sci. 1959;34:147–55.

    Google Scholar 

  5. Miller JD. Fungi and mycotoxins in grain: Implications for stored product research. J Stored Prod Res. 1995;31:1–16.

    Article  CAS  Google Scholar 

  6. Kamigauchi T, et al. Terprenins, novel immunosuppressants produced by Aspergillus candidus. J Antibiot. 1998;51:445–50.

    Article  CAS  Google Scholar 

  7. Munden JE, Butterworth D, Hanscomb G, Verrall MS. Production of chlorflavonin, an antifungal metabolite of Aspergillus candidus. Appl Microbiol. 1970;19:718–20.

    Article  CAS  Google Scholar 

  8. Ma J, et al. Aspergivones A and B, two new lavones isolated from a gorgonian-derived Aspergillus candidus fungus. Nat Prod Res. 2017;31:32–6.

    Article  CAS  Google Scholar 

  9. Buttachon S, et al. Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus Aspergillus candidus KUFA0062. Mar Drugs. 2018;16:119–31.

    Article  CAS  Google Scholar 

  10. Takahashi C, Yoshihira K, Natori S, Umeda M. The structures of toxic metabolites of Aspergillus candidus. I. The compounds A and E, cytotoxic p-terphenyls. Chem Pharm Bull. 1976;24:613–20.

    Article  CAS  Google Scholar 

  11. Lin YK, et al. Cytotoxic p-terphenyls from the deep-sea-derived Aspergillus candidus. Nat Prod Res. 2019;33:1–5.

  12. Rahbæk L, Frisvad JC, Christophersen C. An amendment of Aspergillus section Candidi based on chemotaxonomical evidence. Phytochemistry. 2000;53:581–6.

    Article  Google Scholar 

  13. Guo ZK, et al. p-Terphenyl and diterpenoid mtabolites from endophytic Aspergillus sp. YXf3. J Nat Prod. 2011;75:15–21.

    Article  CAS  Google Scholar 

  14. Cai S, et al. Prenylated polyhydroxy-p-terphenyls from Aspergillus taichungensis ZHN-7-07. J Nat Prod. 2011;74:1106–10.

    Article  CAS  Google Scholar 

  15. Wei H, et al. Prenylterphenyllin and its dehydroxyl analogs, new cytotoxic substances from a marine-derived fungus Aspergillus candidus IF10. J Antibiot. 2007;60:586–90.

    Article  CAS  Google Scholar 

  16. Kurobane I, Vining LC, Mcinnes AG, Smith DG. 3-Hydroxyterphenyllin, a new metabolite of Aspergillus candidus. Structure elucidation by 1H and 13C nuclear magnetic resonance spectroscopy. J Antibiot. 1979;32:559–64.

    Article  CAS  Google Scholar 

  17. Wu SH, Chen YW, Qin S, Huang R. A new spiroketal from Aspergillus terreus, an endophytic fungus in Opuntia ficusindica Mill. J Basic Micro. 2008;48:140–2.

    Article  CAS  Google Scholar 

  18. Frelek J, Szczepek WJ. [Rh2(OCOCF3)4] as an auxiliary chromophore in chiroptical studies on steroidal alcohols. Tetrahedron Asymmetry. 1999;10:1507–20.

    Article  CAS  Google Scholar 

  19. Shiono Y, Ogata K, Koseki T, Murayama T, Funakoshi T. A cleistanthane diterpene from a marine-derived Fusarium species under submerged fermentation. Z Für Naturforsch B. 2010;65:753–6.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support of the National Special Project for Key Science and Technology of Food Safety (grant no. 2017YFC1601302) and the National Natural Science Foundation of China (grant no. 21602247 and 21877124) are gratefully acknowledged.

Author information

Authors and Affiliations

  1. State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China

    JunJie Han, Li Bao, BaoSong Chen, ErWei Li & HongWei Liu

  2. State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China

    JunJie Han, YanFen Xue & YanHe Ma

  3. Savaid Medical School, University of Chinese Academy of Sciences, Beijing, 100049, China

    JunJie Han, Li Bao, BaoSong Chen, ErWei Li & HongWei Liu

  4. College of Life Sciences, Hebei University, Baoding, 071002, China

    FangMing Lu & HanYing Wang

  5. Department of Chemistry, Capital Normal University, Beijing, 100048, China

    ZhengDi Wang, LiPing Xie & ChangBin Guo

Authors
  1. JunJie Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. FangMing Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Li Bao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. HanYing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. BaoSong Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. ErWei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. ZhengDi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. LiPing Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. ChangBin Guo
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. YanFen Xue
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. YanHe Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. HongWei Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to YanHe Ma or HongWei Liu.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

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

Han, J., Lu, F., Bao, L. et al. Terphenyl derivatives and terpenoids from a wheat-born mold Aspergillus candidus. J Antibiot 73, 189–193 (2020). https://doi.org/10.1038/s41429-019-0266-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41429-019-0266-9

Search

Advanced search

Quick links