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. 2015 Mar 26;20(4):5423-37.
doi: 10.3390/molecules20045423.

Dereplication of known nucleobase and nucleoside compounds in natural product extracts by capillary electrophoresis-high resolution mass spectrometry

Junhui Chen  1 , Qian Shi  2   3 , Yanlong Wang  4 , Zhaoyong Li  5 , Shuai Wang  6
Affiliations

Dereplication of known nucleobase and nucleoside compounds in natural product extracts by capillary electrophoresis-high resolution mass spectrometry

Junhui Chen et al. Molecules. .

Abstract

Nucleobase and nucleoside compounds exist widely in various organisms. An often occurring problem in the discovery of new bioactive compounds from natural products is reisolation of known nucleobase and nucleoside compounds. To resolve this problem, a capillary electrophoresis-high resolution mass spectrometry (CE-HR-MS) method providing both rapid separation and accurate mass full-scan MS data was developed for the first time to screen and dereplicate known nucleobase and nucleoside compounds in crude extracts of natural products. Instrumental parameters were optimized to obtain optimum conditions for CE separation and electrospray ionization-time-of-flight mass spectrometry (ESI-TOF/MS) detection. The proposed method was verified to be precise, reproducible, and sensitive. Using this method, known nucleobase and nucleoside compounds in different marine medicinal organisms including Syngnathus acus Linnaeus; Hippocampus japonicus Kaup and Anthopleura lanthogrammica Berkly were successfully observed and identified. This work demonstrates that CE-HR-MS combined with an accurate mass database may be used as a powerful tool for dereplicating known nucleobase and nucleoside compounds in different types of natural products. Rapid dereplication of known nucleobase and nucleoside compounds allows researchers to focus on other leads with greater potential to yield new substances.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
CE-ESI-TOF/MS TIE and EIEs of 15 nucleobase and nucleoside standards. Peak 1. cytosine; 2. uracil; 3. thymine; 4. adenine; 5. hypoxanthine; 6. guanine; 7. xanthine; 8. thymidine; 9. cytidine; 10. uridine; 11. cordycepin; 12. adenosine; 13. 2'-deoxyguanosine; 14. inosine; 15. guanosine. Numbers in parentheses of each panel are the molecular masses of the singly charged ions [M+H]+. Peak 12 (adenosine) and peak 13 (2'-deoxyguanosine) in Figure 1 have the same mass.
Figure 2
Figure 2
CE-ESI-TOF/MS TIE and EIEs of nucleobase compounds in the extract of S. acus Linnaeus. For peak assignment, see Figure 1.
Figure 3
Figure 3
ESI-TOF/MS spectra of (a) uracil; (b) thymine; (c) hypoxanthine; (d) guanine; (e) xanthine in the crude extract of S. acus Linnaeus.
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