NOTES

Discovery of Germicidin Glucuronides from Streptomyces sp. LZ35

  • Haixia Shi ,
  • Yaoyao Li ,
  • Jing Zhu ,
  • Haoxin Wang ,
  • Yuemao Shen
Expand
  • a State Key Laboratory of Microbial Technology, Shandong University, Qingdao, Shandong 266237
    b Key Laboratory of Chemical Biology, Ministry of Education, School of Pharmaceutical Sciences, Shandong University, Jinan 250012
*Corresponding author.E-mail:

Received date: 2021-01-21

  Revised date: 2021-02-10

  Online published: 2021-02-26

Supported by

National Key Research and Development Program(2019YFA0905400); Young Scholars Program of Shandong University(2016WLJH31); Program for Changjiang Scholars and Innovative Research Team in University(IRT_17R68)

Abstract

Two new germicidin glucuronides were isolated from the metabolites of Streptomyces sp. SR111, which is derived from Streptomyces sp. LZ35 through deletion of eight biosynthetic gene clusters by screening of culture media. The chemicla structures of 1 and 2 were determined to be germicidin A-4-O-β-D-glucuronide and germicidin D-4-O-β-D-glucuronide, respectively, by analysis of 1-D and 2-D NMR data and high resolution mass spectrometry. The antibacterial and antifungal activities of 1 and2were eveluated by disc diffusion assay, and they showed no inhibitory activity at 20 μg/disc. The cytotoxic activities of 1 and 2 were tested by methyl thiazolyl tetrazolium (MTT) colorimetric method, and they were inactive against the HepG2 (liver cancer) and HeLa (cervical cancer) cell lines. Remarkably, compounds 1 and 2 represent the first two germicidins with a glucuronic acid moiety, which expands the structural diversity of germicidins

Cite this article

Haixia Shi , Yaoyao Li , Jing Zhu , Haoxin Wang , Yuemao Shen . Discovery of Germicidin Glucuronides from Streptomyces sp. LZ35[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2502 -2506 . DOI: 10.6023/cjoc202101036

References

[1]
Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2020, 83,770.
[2]
Kalkreuter, E.; Pan, G. H.; Cepeda, A. J.; Shen, B. Trends Pharmacol. Sci. 2020, 41,13.
[3]
Bode, H. B.; Bethe, B.; Hofs, R.; Zeeck, A. ChemBioChem 2002, 3,619.
[4]
Zhang, J.; Li, S.; Wu, X.; Guo, Z.; Lu, C.; Shen, Y. Org. Lett. 2017, 19,2442.
[5]
Liu, M.; Lu, C.; Shen, Y. RSC Adv. 2016, 6,49792.
[6]
Liu, C.; Zhu, J.; Li, Y.; Zhang, J.; Lu, C.; Wang, H.; Shen, Y. ChemBioChem 2015, 16,998.
[7]
Li, S.; Li, Y.; Lu, C.; Zhang, J.; Zhu, J.; Wang, H.; Shen, Y. Org. Lett. 2015, 17,3706.
[8]
Zhu, J.; Chen, W.; Li, Y.; Deng, J.; Zhu, D.; Duan, J.; Liu, Y.; Shi, G.; Xie, C.; Wang, H.; Shen, Y. Gene 2014, 546,352.
[9]
Zhao, G.; Li, S.; Wang, Y.; Hao, H.; Shen, Y.; Lu, C. Drug Discoveries Ther. 2013, 7,185.
[10]
Li, Y.; Wang, H.; Liu, Y.; Jiao, Y.; Li, S.; Shen, Y.; Du, L. Angew. Chem., Int. Ed. 2018, 57,6221.
[11]
Zhang, H.; Saurav, K.; Yu, Z.; Mandi, A.; Kurtan, T.; Li, J.; Tian, X.; Zhang, Q.; Zhang, W.; Zhang, C. J. Nat. Prod. 2016, 79,1610.
[12]
Chemler, J. A.; Buchholz, T. J.; Geders, T. W.; Akey, D. L.; Rath, C. M.; Chlipala, G. E.; Smith, J. L.; Sherman, D. H. J. Am. Chem. Soc. 2012, 134,7359.
[13]
Wilson, M. C.; Moore, B. S. Nat. Prod. Rep. 2012, 29,72.
Outlines

/