Citation: Ningning Zhao, Zhiqiang Liu, Junpeng Xing, Zhong Zheng, Fengrui Song, Shu Liu. A novel strategy for high-specificity, high-sensitivity, and high-throughput study for gut microbiome metabolism of aromatic carboxylic acids[J]. Chinese Chemical Letters, ;2022, 33(6): 3031-3034. doi: 10.1016/j.cclet.2021.09.022 shu

A novel strategy for high-specificity, high-sensitivity, and high-throughput study for gut microbiome metabolism of aromatic carboxylic acids

Ningning Zhao ^{a, b} ,
Zhiqiang Liu ^{a, b, c} ,
Junpeng Xing ^a ,
Zhong Zheng ^a ,
Fengrui Song ^a ,
Shu Liu ^{a, *,}

a.
National Center of Mass Spectrometry in Changchun and Jilin Provincial Key Laboratory of Chinese Medicine Chemistry and Mass Spectrometry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
Institute of Applied Chemistry and Engineering, University of Science and Technology of China, Hefei 230029, China
c.
State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

mslab20@ciac.ac.cn

1985liushu@163.com

Received Date: 16 April 2021
Revised Date: 10 August 2021
Accepted Date: 6 September 2021
Available Online: 10 September 2021

Figures(4)

Aromatic carboxylic acids (ACAs) may be as transformed key metabolites via gut microbiome for playing better pharmacological effects. However, it's rare to achieve high-specificity, high-sensitivity, and high-throughput detection simultaneously, especially, for tracing trace ACAs in gut microbiome. In this work, firstly, a novel dual-template and double-shelled molecularly imprinted 96-well microplates (DDMIPs) was designed and amplified signal for p-hydroxybenzoic acid (PBA) and 3, 4, 5-trimethoxycinnamic acid (TMA). Additionally, the DDMIPs and a stable isotope labeling derivatization (SILD) method combined with the ultra-high performance liquid chromatography triple quadrupole tandem mass spectrometry (UHPLC-TQ MS) was firstly stepwise integrated, achieving high-effective, high-sensitive, and high-throughput study of gut microbiome metabolism. The whole strategy showed lower limits of detections (LODs) up to 1000 folds than the traditional method, and revealed a more real metabolism-time profile of PBA and TMA by 3-step signal amplification. The platform also laid the foundation for fast, simple, high-selective, high-effective, and high-throughput metabolism and pharmacological research.
1. [1]
  V. Ridaura, Y. Belkaid, Cell 161 (2015) 193-194. doi: 10.1016/j.cell.2015.03.033
2. [2]
  Z. Yang, J. Li, X. Gui, et al., Mol. Psychiatry 25 (2020) 2759-2772. doi: 10.1038/s41380-020-0729-1
3. [3]
  L. Pan, P. Han, S. Ma, et al., Acta Pharm. Sin. B 10 (2020) 249-261. doi: 10.1016/j.apsb.2019.10.007
4. [4]
  Z.X. Zhao, J. Fu, S.R. Ma, et al., Theranostics 8 (2018) 5945-5959. doi: 10.7150/thno.28068
5. [5]
  J.B. Yu, Z.X. Zhao, R. Peng, et al., Front. Pharmacol. 10 (2019) 268. doi: 10.3389/fphar.2019.00268
6. [6]
  Q. Cui, Y. Pan, X. Xu, et al., Fitoterapia 109 (2016) 67-74. doi: 10.1016/j.fitote.2015.12.011
7. [7]
  Y. Li, G. Zhou, S. Xing, P. Tu, X. Li, J. Agric. Food Chem. 63 (2015) 6764-6771. doi: 10.1021/acs.jafc.5b02881
8. [8]
  X. Wang, X. Chang, X. Luo, et al., Front. Pharmacol. 10 (2019) 826. doi: 10.3389/fphar.2019.00826
9. [9]
  S. Chandra, A. Roy, M. Jana, K. Pahan, Neurobiol. Dis. 124 (2019) 379-395. doi: 10.1016/j.nbd.2018.12.007
10. [10]
  E. Mhillaj, S. Catino, F.M. Miceli, et al., Mol. Neurobiol. 55 (2018) 905-916. doi: 10.1007/s12035-017-0381-1
11. [11]
  M. Zhao, S. Huang, H. Xie, et al., Anal. Chem. 92 (2020) 10540-10547. doi: 10.1021/acs.analchem.0c01366
12. [12]
  K.Z. Chin, S.M. Chang, ACS Appl. Nano Mater. 2 (2019) 89-99. doi: 10.1021/acsanm.8b01706
13. [13]
  Q. Huang, Z. Zhao, D. Nie, et al., Anal. Chem. 91 (2019) 4116-4123. doi: 10.1021/acs.analchem.8b05791
14. [14]
  M. Liu, S.B. Torsetnes, C. Wierzbicka, et al., Anal. Chem. 91 (2019) 10188-10196. doi: 10.1021/acs.analchem.9b02211
15. [15]
  V. Pichon, N. Delaunay, A. Combes, Anal. Chem. 92 (2020) 16-33. doi: 10.1021/acs.analchem.9b04816
16. [16]
  J.J. BelBruno, Chem. Rev. 119 (2019) 94-119. doi: 10.1021/acs.chemrev.8b00171
17. [17]
  Y. Zhang, D. Liu, J. Peng, et al., Talanta 209 (2020) 120555. doi: 10.1016/j.talanta.2019.120555
18. [18]
  L. Guo, X. Ma, X. Xie, et al., Chem. Eng. J. 361 (2019) 245-255. doi: 10.1016/j.cej.2018.12.076
19. [19]
  H.Y. Wang, P.P. Cao, Z.Y. He, et al., Nanoscale 11 (2019) 17018-17030. doi: 10.1039/C9NR04655K
20. [20]
  C. Jia, M. Zhang, Y. Zhang, et al., ACS Appl. Mater. Interfaces 11 (2019) 32431-32440. doi: 10.1021/acsami.9b11533
21. [21]
  X. Bi, Z. Liu, Anal. Chem. 86 (2014) 12382-12389. doi: 10.1021/ac503778w
22. [22]
  X. Bi, Z. Liu, Anal. Chem. 86 (2014) 959-966. doi: 10.1021/ac403736y
23. [23]
  J. Yu, C. Zhang, P. Dai, S. Ge, Anal. Chim. Acta 651 (2009) 209-214. doi: 10.1016/j.aca.2009.08.018
24. [24]
  Y.Z. Zhang, B. Qin, B. Zhang, et al., Anal. Chim. Acta 1096 (2020) 193-202. doi: 10.1016/j.aca.2019.10.060
25. [25]
  X. Liu, F. Wu, C. Au, et al., J. Appl. Polym. Sci. 136 (2019) 46984. doi: 10.1002/app.46984
26. [26]
  H. Li, R. Long, C. Tong, et al., Talanta 194 (2019) 969-976. doi: 10.1016/j.talanta.2018.10.099
27. [27]
  J.B. Weon, H. Park, H.J. Yang, J.Y. Ma, C.J. Ma, J. Nat. Med. 65 (2011) 375-380. doi: 10.1007/s11418-010-0494-6
28. [28]
  J.B. Weon, H.J. Yang, J.Y. Ma, C.J. Ma, J. Nat. Med. 66 (2012) 510-515. doi: 10.1007/s11418-011-0617-8
29. [29]
  J. Guan, L. Wang, J. Jin, et al., J. Pharm. Biomed. Anal. 170 (2019) 1-7. doi: 10.1016/j.jpba.2019.03.022
30. [30]
  E. Lamy, L. Pilyser, C. Paquet, E. Bouaziz-Amar, S. Grassin-Delyle, Talanta 224 (2020) 121881. doi: 10.1016/j.talanta.2020.121881
31. [31]
  S. Zhu, Z. Zheng, H. Peng, et al., J. Chromatogr. A 1616 (2020) 460794. doi: 10.1016/j.chroma.2019.460794
32. [32]
  J. Leng, H. Wang, L. Zhang, et al., Anal. Chim. Acta 758 (2013) 114-121. doi: 10.1016/j.aca.2012.11.008
33. [33]
  Y. Xu, L. Sun, X. Wang, et al., Talanta 199 (2019) 97-106. doi: 10.1016/j.talanta.2019.02.011
34. [34]
  Q.F. Zhu, Z. Zhang, P. Liu, et al., J. Chromatogr. A 1460 (2016) 100-109. doi: 10.1016/j.chroma.2016.07.017
35. [35]
  N. Zhao, T. Zhao, M. Fan, et al., Talanta 224 (2020) 121791.
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