Skip to main content
SpringerLink
Log in

Metabolites with Gram-negative bacteria quorum sensing inhibitory activity from the marine animal endogenic fungus Penicillium sp. SCS-KFD08

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Three new compounds named penicitor A, aculene E and penicitor B, as well as four known compounds, were isolated from the fermentation broth of Penicillium sp. SCS-KFD08 associated with a marine animal Sipunculus nudus from the Haikou bay of China. Their planar structures and absolute configurations were unambiguously elucidated by spectroscopic data, Mosher’s method, CD spectrum analysis along with quantum ECD calculation. Among them, compounds 2–7 showed quorum sensing inhibitory activity against Chromobacterium violaceum CV026, and could significantly reduce violacein production in N-hexanoyl-l-homoserine lactone (C6-HSL) induced C. violaceum CV026 cultures at sub-inhibitory concentrations.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Fukumoto A, Murakami C, Anzai Y, Kato F (2015) Maniwamycins: new quorum-sensing inhibitors against Chromobacterium violaceum CV026 were isolated from Streptomyces sp. TOHO-M025. J Antibiot. doi:10.1038/ja.2015.126

    PubMed  Google Scholar 

  • Huang SZ, Cheng BH, Ma QY, Wang Q, Kong FD, Dai HF, Qiu SQ, Zhao YX (2016) Anti-allergic prenylated hydroquinones and alkaloids from the fruiting body of Ganoderma calidophilum. RSC Adv 6:21139–21147

    Article  CAS  Google Scholar 

  • Jiao WH, Huang XJ, Yang JS, Yang F, Piao SJ, Gao H, Li J, Ye WC, Yao XS, Chen WS (2012) Dysidavarones A-D, new sesquiterpene quinones from the marine sponge Dysidea avara. Org Lett 14:202–205

    Article  CAS  PubMed  Google Scholar 

  • Kong FD, Wang Y, Liu PP, Dong TH, Zhu WM (2013) Thiodiketopiperazines from the marine-derived fungus Phoma sp. OUCMDZ-1847. J Nat Prod 77:132–137

    Article  PubMed  Google Scholar 

  • LaSarre B, Federle MJ (2013) Exploiting quorum sensing to confuse bacterial pathogens. Microbiol Mol Biol Rev 77:73–111

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Li SD, Wei MY, Chen GY, Lin YC (2012) Two new dihydroisocoumarins from the endophytic fungus Aspergillus sp. collected from the South China Sea. Chem Nat Compd 48:371–373

    Article  CAS  Google Scholar 

  • Merli M, Lucidi C, Di Gregorio V, Falcone M, Giannelli V, Lattanzi B, Giusto M, Ceccarelli GO, Riggio A, Venditti M (2015) The spread of multi drug resistant infections is leading to an increase in the empirical antibiotic treatment failure in cirrhosis: a prospective survey. PLoS One 10:e0127448

    Article  PubMed  PubMed Central  Google Scholar 

  • Petersen LM, Hoeck C, Frisvad JC, Gotfredsen CH, Larsen TO (2014) Dereplication guided discovery of secondary metabolites of mixed biosynthetic origin from Aspergillus aculeatus. Molecules 19:10898–10921

    Article  CAS  PubMed  Google Scholar 

  • Rasmussen TB, Skindersoe ME, Bjarnsholt T, Phipps RK, Christensen KB, Jensen PO, Andersen JB, Koch B, Larsen TO, Hentzer M, Eberl L, Hoiby N, Eberl L (2005) Identity and effects of quorum-sensing inhibitors produced by Penicillium species. Microbiology 151:1325–1340

    Article  CAS  PubMed  Google Scholar 

  • Stephens PJ, Pan JJ, Krohn KJ (2007) Determination of the absolute configurations of pharmacological natural products via density functional theory calculations of vibrational circular dichroism: the new cytotoxic iridoid prismatomerin. J Org Chem 72:7641–7649

    Article  CAS  PubMed  Google Scholar 

  • Tan NP, Donner CD (2009) Total synthesis and confirmation of the absolute stereochemistry of semiviriditoxin, a naphthopyranone metabolite from the fungus Paecilomyces variotii. Tetrahedron 65:4007–4012

    Article  CAS  Google Scholar 

  • Wang Y, Wang LP, Zhuang YB, Kong FD, Zhang CX, Zhu WM (2014) Phenolic polyketides from the co-cultivation of marine-derived Penicillium sp. WC-29-5 and Streptomyces fradiae 007. Marine Drugs 12:2079–2088

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Yada H, Sato H, Toshima H, Deura M, Ichihara A (2001) (−)-semivioxanthin, a new abscisic active compound against Hinoki cypress leaves isolated from Cryptosporiopsis abietina. Biosci Biotechnol Biochem 65:484–486

    Article  CAS  PubMed  Google Scholar 

  • Zhou LM, Zheng HD, Tang YD, Yu WG, Gong QH (2013) Eugenol inhibits quorum sensing at sub-inhibitory concentrations. Biotechnol Lett 35:631–637

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

This work was supported by Special Fund for Agro-Scientific Research in the Public Interest (201303117), Fundamental Scientific Research Funds for CATAS (ITBB2016) and Natural Science Foundation of Hainan Province (20152035).

Author information

Author notes

    Authors and Affiliations

    1. Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou, 571101, People’s Republic of China

      Fan Dong Kong, Li Man Zhou, Qing Yun Ma, Sheng Zhuo Huang, Pei Wang, Hao Fu Dai & You Xing Zhao

    Authors
    1. Fan Dong Kong
      View author publications

      You can also search for this author in PubMed Google Scholar

    2. Li Man Zhou
      View author publications

      You can also search for this author in PubMed Google Scholar

    3. Qing Yun Ma
      View author publications

      You can also search for this author in PubMed Google Scholar

    4. Sheng Zhuo Huang
      View author publications

      You can also search for this author in PubMed Google Scholar

    5. Pei Wang
      View author publications

      You can also search for this author in PubMed Google Scholar

    6. Hao Fu Dai
      View author publications

      You can also search for this author in PubMed Google Scholar

    7. You Xing Zhao
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding author

    Correspondence to You Xing Zhao.

    Ethics declarations

    Conflict of interest

    The authors declare that there are no conflicts of interest.

    Additional information

    Fan Dong Kong and Li Man Zhou are contributed equally to this work.

    Electronic supplementary material

    Below is the link to the electronic supplementary material.

    12272_2016_844_MOESM1_ESM.pdf

    The 2D NMR spectra of compounds 1−3, the 18S rRNA gene sequences of Penicillium sp. SCS-KFD08 and the quantum calculation detail were supplied. These materials are available free of charge via the. Supplementary material 1 (PDF 3214 kb)

    Rights and permissions

    Reprints and permissions

    About this article

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this article

    Kong, F.D., Zhou, L.M., Ma, Q.Y. et al. Metabolites with Gram-negative bacteria quorum sensing inhibitory activity from the marine animal endogenic fungus Penicillium sp. SCS-KFD08. Arch. Pharm. Res. 40, 25–31 (2017). https://doi.org/10.1007/s12272-016-0844-3

    Download citation

    • Received:

    • Accepted:

    • Published:

    • Issue Date:

    • DOI: https://doi.org/10.1007/s12272-016-0844-3

    Keywords

    Search

    Navigation