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Indole Alkaloids from the Cigar Tobacco-Derived Endophytic Fungus Aspergillus oryzae and Their Antibacterial Activity

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Chemistry of Natural Compounds Aims and scope

Two new indole alkaloids, 6-(4-methoxyphenoxy)-4-methoxy-2-methyl-1H-indole (1) and 6-(3,5-dimethoxyphenoxy)-4-methoxy-2-methyl-1H-indole (2), along with four known ones (3–6), were isolated from the fermentation products of the cigar tobacco-derived endophytic fungus Aspergillus oryzae. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were evaluated for their antibacterial and antioxidant activities. The results showed that compounds 1 and 2 exhibited good anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity with IZD of 22.4 ± 2.4 and 24.6 ± 2.2 mm, respectively.

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References

  1. S. Gupta, P. Chaturvedi, M. G. Kulkarni, and J. Van Staden, Biotechnol. Adv., 39, 107462 (2019).

    Article  PubMed  Google Scholar 

  2. I. T. Malik and H. Brotz-Oesterhelt, Nat. Prod. Rep., 34, 815 (2017).

    Article  CAS  PubMed  Google Scholar 

  3. C. Schinke, T. Martins, S. C. N. Queiroz, I. S. Melo, and F. G. R. Reyes, J. Nat. Prod., 80, 121 (2017).

    Article  Google Scholar 

  4. T. T. Liu, L. P. Wang, L. Zhang, H. Y. Jiang, Y. N. Zhang, and L. G. Mao, Nat. Prod. Res., 34, 1430 (2020).

    Article  PubMed  Google Scholar 

  5. F. Bongomin, C. R. Batac, M. D. Richardson, and D. W. Denning, Mycopathologia, 183, 485 (2018).

    Article  PubMed  Google Scholar 

  6. J. M. Restrepo-Florez, A. Bassi, and M. R. Thompson, Int. Biodeterior. Biodegrad., 88, 83 (2014).

    Article  CAS  Google Scholar 

  7. S. Skanda and B. S. Vijayakumar, Curr. Microbiol., 78, 1317 (2021).

    Article  CAS  PubMed  Google Scholar 

  8. M. Y. Deng, X. Chen, Z. Y. Shi, and S. S. Xie, Fitoterapia, 151, 104882 (2021).

    Article  CAS  PubMed  Google Scholar 

  9. G. M. Daba, W. A. Elkhateeb, and F. A. Mostafa, Bioresour. Bioprocess., 8, 52 (2021).

    Article  Google Scholar 

  10. M. Zhou, K. Zhou, P. He, K. M. Wang, R. Z. Zhu, Y. D. Wang, W. Dong, G. P. Li, H. Y. Yang, Y. Q. Ye, G. Du, X. M. Li, and Q. F. Hu, Planta. Med., 82, 414 (2016).

    Article  CAS  PubMed  Google Scholar 

  11. R. Orfali, S. Perveen, M. F. Khan, A. F. Ahmed, M. A. Wadaan, A. M. Al-Taweel, A. S. Alqahtani, F. A. Nasr, S. Tabassum, P. Luciano, G. Chianese, J. H. Sheu, and O. Taglialatela-Scafati, Mar. Drugs., 19, 333 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. R. Ren, C. J. Chen, S. S. Hu, H. M. Ge, W. Y. Zhu, R. X. Tan, and R. H. Jiao, Chem. Biodiv., 12, 371 (2015).

    Article  CAS  Google Scholar 

  13. W. G. Wang, L. Q. Du, S. L. Sheng, A. Li, Y. P. Li, G. G. Cheng, G. P. Li, G. L. Sun, Q. F. Hu, and Y. Matsuda, Org. Chem. Front., 6, 571 (2019).

    Article  CAS  Google Scholar 

  14. C. W. Liu, A. Minami, T. Ozaki, T, J. Wu, H. Kawagishi, J. I. Maruyama, and H. Oikawa, J. Am. Chem. Soc., 141, 15519 (2019).

  15. L. Liu, L. Bao, L. Wang, K. Ma, J. J. Han, Y. L. Yang, R. X. Liu, J. W. Ren, W. B. Yin, W. Z. Wang, and H. W. Liu, J. Org. Chem., 83, 812 (2018).

    Article  CAS  PubMed  Google Scholar 

  16. X. Hu, Q. W. Xia, Y. Y. Zhao, Q. H. Zheng, Q. Y. Liu, L. Chen, and Q. Q. Zhang, Chem. Pharm. Bull., 46, 942 (2015).

    Google Scholar 

  17. M. Shaaban, M. M. El-Metwally, and H. Nasr, Nat. Prod. Res., 28, 86 (2014).

    Article  CAS  PubMed  Google Scholar 

  18. D. Nikolic, T. Godecke, S. N. Chen, J. White, D. C. Lankin, G. F. Pauli, and R. B. van Breemen, Fitoterapia, 83, 441 (2012).

    Article  CAS  PubMed  Google Scholar 

  19. P. L. Wu, Y. L. Hsu, and C. W. Jao, J. Nat. Prod., 69, 1467 (2006).

    Article  CAS  PubMed  Google Scholar 

  20. H. Chen, J. Bai, Z. F. Fang, S. S. Yu, S. G. Ma, S. Xu, Y. Li, J. Qu, J. H. Ren, L. Li, Y. K. Si, and X. G. Chen, J. Nat. Prod., 74, 2438 (2011).

    Article  CAS  PubMed  Google Scholar 

  21. F. Tabassum, C. M. Hasan, M. M. Masud, S. Jamshidi, K. M. Rahman, and M. Ahsan, Phytochemistry, 186, 112744 (2021).

    Article  CAS  PubMed  Google Scholar 

  22. M. P. Epplin, A. Mohan, L. D. Harris, Z. J. Zhu, K. L. Strong, J. Bacsa, P. Le, D. S. Menaldino, S. F. Traynelis, and D. C. Liotta, J. Med. Chem., 63, 7569 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. D. R. Beukes, M. T. Davies-Coleman, M. Kelly-Borges, M. K. Harper, and D. J. Faulkner, J. Nat. Prod., 61, 699 (1998).

    Article  CAS  PubMed  Google Scholar 

  24. H. Tanak, A. Agar, and M. Yavuz, J. Mol. Model., 16, 577 (2010).

    Article  CAS  PubMed  Google Scholar 

  25. F. D. Kong, S. L. Zhang, S. Q. Zhou, Q. Y. Ma, Q. Y. Xie, J. P. Chen, J. H. Li, L. M. Zhou, J. Z. Yuan, Z. Hu, H. F. Dai, X. L. Huang, and Y. X. Zhao, J. Nat. Prod., 82, 3456 (2019).

    Article  CAS  PubMed  Google Scholar 

  26. K. Xu, X. L. Yuan, C. Li, and X. D. Li, Mar. Drugs., 18, 54 (2020).

    Article  CAS  PubMed Central  Google Scholar 

  27. M. L. Wang, R. Chen, F. J. Sun, P. R. Cao, X. R. Chen, and M. H. Yang, Tetrahedron Lett., 68, 152914 (2021).

    Article  CAS  Google Scholar 

  28. Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, Vol. 32, Clinical and Laboratory Standards Institute, Wayne, Pa, USA, 9th Edition, 2012.

Download references

Acknowledgment

This project was supported financially by the Foundation of Chemical and Biological Innovation Studio of Yunnan Industrial Co., Ltd., the Foundation of Yunnan Tobacco Industry Co., Ltd. (No. 2020JC02), the National Natural Science Foundation of China (No. 21967021), and the Foundation of Yunnan Innovative Research Team (2019HC020).

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Authors and Affiliations

  1. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, 650031, Kunming, P. R. China

    Man-fei Li, Lu Liu, Jun-Na Zheng, Xue-Jiao Gu, Ya-Ning Zhu, Jia-Meng Dai, Qiu-Fen Hu & Yin-Ke Li

  2. Key Laboratory of Tobacco Chemistry of Yunnan Province, China Tobacco Yunnan Industrial Co., Ltd., 650231, Kunming, P. R. China

    Dong Xiao, Ling-Chao Zhu, Jiao Xie, Xu Wang, Jia-Meng Dai, Qi-Li Mi, Ye-Kun Yang & Jian-Quan Shi

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  1. Man-fei Li
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  2. Dong Xiao
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  3. Ling-Chao Zhu
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  4. Lu Liu
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  14. Yin-Ke Li
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Corresponding authors

Correspondence to Yin-Ke Li or Jian-Quan Shi.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2022, pp. 920–923.

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Li, Mf., Xiao, D., Zhu, LC. et al. Indole Alkaloids from the Cigar Tobacco-Derived Endophytic Fungus Aspergillus oryzae and Their Antibacterial Activity. Chem Nat Compd 58, 1093–1097 (2022). https://doi.org/10.1007/s10600-022-03872-x

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