New anti-inflammatory metabolites produced by Streptomyces violaceoruber isolated from Equus burchelli feces

Abstract

Three new metabolites (24), together with one known compound, GTRI-02, (1) were isolated from a fermentation broth of Streptomyces violaceoruber derived from Equus burchelli feces. The structures of the new compounds 24 were established using comprehensive NMR spectroscopic data analysis as well as UV, IR and MS data. The anti-inflammatory activity of compounds 14 was tested by examining their ability to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells. Compound 2 showed a moderate inhibition of NO production with IC50 value of 51.2 μm.

Access options

Rent or Buy article

Get time limited or full article access on ReadCube.

from$8.99

All prices are NET prices.

Figure 1
Figure 2
Figure 3
Figure 4

References

  1. 1

    Savage, D. C. Microbial ecology of the gastrointestinal tract. Annu. Rev. Microbiol. 31, 107–133 (1977).

    CAS  Article  Google Scholar 

  2. 2

    Jiang, Y. et al. Diversity and bioactivity of cultivable animal fecal actinobacteria. Adv. Microbiol. 3, 1–13 (2013).

    CAS  Article  Google Scholar 

  3. 3

    Jiang, Y. et al. Diversity of cultivable actinomycetes in 6 species of herbivore feces. Int. J. Microbiol. Res. 2, 110–117 (2013).

    Google Scholar 

  4. 4

    Chen, X. et al. Enteractinococcus lamae sp. nov. and Enteractinococcus viverrae sp. nov., isolated from animal faeces. Antonie Van Leeuwenhoek 108, 1477–1483 (2015).

    CAS  Article  Google Scholar 

  5. 5

    Chen, X. et al. Corynebacterium faecale sp. nov. isolated from the faeces of Assamese macaque. Int. J. Syst. Evol. Microbiol. 66, 2478–2483 (2016).

    CAS  Article  Google Scholar 

  6. 6

    Zhang, J. et al. Violapyrones A–G, α-pyrone derivatives from Streptomyces violascens isolated from Hylobates hoolock feces. J. Nat. Prod. 76, 2126–2130 (2013).

    CAS  Article  Google Scholar 

  7. 7

    Ding, N. et al. Bafilomycins and odoriferous sesquiterpenoids from Streptomyces albolongus isolated from Elephas maximus feces. J. Nat. Prod. 79, 799–805 (2016).

    CAS  Article  Google Scholar 

  8. 8

    Yeo, W. H. et al. GTRI-02, a new lipid peroxidation inhibitor from Micromonospora sp. SA246. J. Antibiot. 51, 952–953 (1998).

    CAS  Article  Google Scholar 

  9. 9

    Abdalla, M. A. et al. Khatmiamycin, a motility inhibitor and zoosporicide against the grapevine downy mildew pathogen Plasmopara viticola from Streptomyces sp. ANK313. J. Antibiot. 64, 655–659 (2011).

    CAS  Article  Google Scholar 

  10. 10

    Maskey, R. P. et al. Juglomycins G-J: isolation from streptomycetes and structure elucidation. Z. Naturforsch. B 60, 183–188 (2005).

    CAS  Article  Google Scholar 

  11. 11

    Husain, S. M., Schätzle, M. A., Rör, C., Lüdeke, S. & Müller, M. Biomimetic asymmetric synthesis of (R-GTRI-02 and (3 S, 4 R-3,4-dihydroxy-3,4-dihydronaphthalen-1(2H-ones. Org. Lett. 14, 3600–3603 (2012).

    CAS  Article  Google Scholar 

  12. 12

    Ozaki, T., Nishiyama, M. & Kuzuyama, T. Novel tryptophan metabolism by a potential gene cluster that is widely distributed among actinomycetes. J. Biol. Chem. 288, 9946–9956 (2013).

    CAS  Article  Google Scholar 

  13. 13

    Bari, L. D., Pescitelli, G., Pratelli, C., Pini, D. & Salvadori, P. Determination of absolute configuration of acyclic 1,2-diols with Mo2(OAc)4. 1. Snatzke’s method revisited. J. Org. Chem. 66, 4819–4825 (2001).

    Article  Google Scholar 

  14. 14

    Zhang, H., Xiao, X., Conte, M. M., Khalil, Z. & Capon, R. J. Spiralisones A–D: acylphloroglucinol hemiketals from an Australian marine brown alga Zonaria spiralis. Org. Biomol. Chem. 10, 9671–9676 (2012).

    CAS  Article  Google Scholar 

  15. 15

    Liu, F. et al. Phloroglucinol derivatives with protein tyrosine phosphatase 1B inhibitory activities from Eugenia jambolana seeds. J. Nat. Prod. 80, 544–550 (2017).

    CAS  Article  Google Scholar 

  16. 16

    Wu, Q. et al. Varioxiranols A–G and 19-O-methyl-22-methoxypre-shamixanthone, PKS and hybrid PKS-derived metabolites from a sponge-associated Emericella variecolor fungus. J. Nat. Prod. 78, 2461–2470 (2015).

    CAS  Article  Google Scholar 

  17. 17

    Jarvis, B. B., Wang, S. & Ammon, H. L. Trichoverroid stereoisomers. J. Nat. Prod. 59, 254–261 (1996).

    CAS  Article  Google Scholar 

  18. 18

    Du, L., Zhu, T., Fang, Y., Gu, Q. & Zhu, W. Unusual C25 steroid isomers with bicyclo[4.4.1] A/B rings from a volcano ash-derived fungus Penicillium citrinum. J. Nat. Prod. 71, 1343–1351 (2008).

    CAS  Article  Google Scholar 

  19. 19

    Ma, Q. et al. Structures and biological activities of the triterpenoids and sesquiterpenoids from Alisma orientale. Phytochemistry 131, 150–157 (2016).

    CAS  Article  Google Scholar 

Download references

Acknowledgements

This work was funded by National Natural Science Foundation of China (Nos 81573327 and 31460005), Basic Scientific Research Fund of Northeastern University, China (No N142002001).

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Yi Jiang or Li Han.

Ethics declarations

Competing interests

The authors declare no conflict of interest.

Additional information

Supplementary Information accompanies the paper on The Journal of Antibiotics website

Supplementary information

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Ma, J., Lei, H., Chen, X. et al. New anti-inflammatory metabolites produced by Streptomyces violaceoruber isolated from Equus burchelli feces. J Antibiot 70, 991–994 (2017). https://doi.org/10.1038/ja.2017.75

Download citation

Further reading

Search

Quick links