Citation: Qiongqiong Wan, Yanan Xiao, Guifang Feng, Xin Dong, Wenjing Nie, Ming Gao, Qingtao Meng, Suming Chen. Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids[J]. Chinese Chemical Letters, ;2024, 35(4): 108775. doi: 10.1016/j.cclet.2023.108775 shu

Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids

The Institute for Advanced Studies, Renmin Hospital of Wuhan University, Wuhan University, Wuhan 430072, China

qtmeng@whu.edu.cn

sm.chen@whu.edu.cn

Received Date: 4 March 2023
Revised Date: 13 June 2023
Accepted Date: 5 July 2023
Available Online: 6 July 2023

Figures(4)

There is a close relationship between the biological functions of lipids and their structures, and various isomers greatly increases the complexity of lipid structures. The C=C bond location and sn-position are two of the essential attributes that determine the structures of unsaturated lipids. However, simultaneous identification of both attributes remains challenging. Here, we develop a visible-light-activated aziridination reaction system, which enables the dual-resolving of the C=C bond location and sn-position isomerism of in lipids when combines with liquid chromatography-mass spectrometry (LC-MS). Based on the derivatization of C=C bonds with PhI=NTs, their location in lipids could be easily identified by tandem MS. Especially, the sn-position isomers of unsaturated phosphatidylcholine (PC) can be separated and quantified by LC-MS after the derivatization. By using the proposed method, the significant changes of the sn-position isomers ratios of PC in mouse brain ischemia were revealed. This study offers a powerful tool for deep lipid structural biology.
- Aziridination,
- Lipid isomers,
- C=C bond location,
- sn-Position,
- Mass spectrometry
1. [1]
  M.P. Wymann, R. Schneiter, Nat. Rev. Mol. Cell Biol. 9 (2008) 162–176. doi: 10.1038/nrm2335
2. [2]
  X.L. Han, Nat. Rev. Endocrinol. 12 (2016) 668–679. doi: 10.1038/nrendo.2016.98
3. [3]
  Z. Wang, E. Klipfell, B.J. Bennett, et al., Nature 472 (2011) 57–63. doi: 10.1038/nature09922
4. [4]
  M.R. Wenk, Cell 143 (2010) 888–895. doi: 10.1016/j.cell.2010.11.033
5. [5]
  P. Xie, J. Zhang, P. Wu, et al., Chin. Chem. Lett. 34 (2023) 107349. doi: 10.1016/j.cclet.2022.03.072
6. [6]
  Y. Hao, Z. Zhang, G. Feng, et al., iScience 24 (2021) 102974. doi: 10.1016/j.isci.2021.102974
7. [7]
  B. Antonny, S. Vanni, H. Shindou, et al., Trends Cell Biol. 25 (2015) 427–436. doi: 10.1016/j.tcb.2015.03.004
8. [8]
  L.M. Bond, M. Miyazaki, L.M. O'Neill, F. Ding, J.M. Ntambi, Fatty acid desaturation and elongation in mammals, in: N.D. Ridgway, McLeod R.S. (Eds. ), Biochemistry of Lipids, Lipoproteins and Membranes, Elsevier, Netherlands, 2015, pp. 185–208.
9. [9]
  G. Feng, M. Gao, L. Wang, et al., Nat. Commun. 13 (2022) 2652. doi: 10.1038/s41467-022-30249-z
10. [10]
  G. Feng, Y. Hao, L. Wu, et al., Chem. Sci. 11 (2020) 7244–7251. doi: 10.1039/D0SC01149E
11. [11]
  C. Sun, C. Ma, L. Li, et al., Chin. Chem. Lett. 33 (2022) 2073–2076. doi: 10.1016/j.cclet.2021.08.034
12. [12]
  X. Ma, Y. Xia, Angew. Chem. Int. Ed. 53 (2014) 2592–2596. doi: 10.1002/anie.201310699
13. [13]
  M.C. Thomas, T.W. Mitchell, S.J. Blanksby, J. Am. Chem. Soc. 128 (2006) 58–59. doi: 10.1021/ja056797h
14. [14]
  P.E. Williams, D.R. Klein, S.M. Greer, et al., J. Am. Chem. Soc. 139 (2017) 15681–15690. doi: 10.1021/jacs.7b06416
15. [15]
  W. Cao, S. Cheng, J. Yang, et al., Nat. Commun. 11 (2020) 375. doi: 10.1038/s41467-019-14180-4
16. [16]
  N.S. Kelley, N.E. Hubbard, K.L. Erickson, J. Nutr. 137 (2007) 2599–2607. doi: 10.1093/jn/137.12.2599
17. [17]
  R. Bandu, H.J. Mok, K.P. Kim, Mass Spectrom. Rev. 37 (2018) 107–138. doi: 10.1002/mas.21510
18. [18]
  Q.Y. Cheng, J. Xiong, F. Wang, et al., Chin. Chem. Lett. 29 (2018) 115–118. doi: 10.1016/j.cclet.2017.06.009
19. [19]
  X.M. Tang, T.T. Ye, X.J. You, et al., Chin. Chem. Lett. 34 (2023) 107531. doi: 10.1016/j.cclet.2022.05.045
20. [20]
  T. Porta Siegel, K. Ekroos, S.R. Ellis, Angew. Chem. Int. Ed. 58 (2019) 6492–6501. doi: 10.1002/anie.201812698
21. [21]
  S. Tang, X. Chen, Y. Ke, et al., Anal. Chem. 94 (2022) 12750–12756. doi: 10.1021/acs.analchem.2c02375
22. [22]
  P. Müller, C. Fruit, Chem. Rev. 103 (2003) 2905–2920. doi: 10.1021/cr020043t
23. [23]
  M. Nakanishi, A.F. Salit, C. Bolm, Adv. Syn. Catal. 350 (2008) 1835–1840. doi: 10.1002/adsc.200700519
24. [24]
  Y. Zhao, H. Zhao, X. Zhao, et al., Anal. Chem. 89 (2017) 10270–10278. doi: 10.1021/acs.analchem.7b01870
25. [25]
  S. Masakado, Y. Kobayashi, Y. Takemoto, Chem. Pharm. Bull. 66 (2018) 688–690. doi: 10.1248/cpb.c18-00198
26. [26]
  G. Feng, M. Gao, R. Fu, et al., Biorxiv (2022) https://doi.org/10.1101/2022.04.24.489320. doi: 10.1101/2022.04.24.489320
1. [1]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
2. [2]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
3. [3]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
4. [4]
  Keqiang Shi , Xiujuan Hong , Dongyan Xu , Tao Pan , Huiwen Wang , Hongru Feng , Cheng Guo , Yuanjiang Pan . Analysis of RNA modifications in peripheral white blood cells from breast cancer patients by mass spectrometry. Chinese Chemical Letters, 2025, 36(3): 110079-. doi: 10.1016/j.cclet.2024.110079
5. [5]
  Yongyi Li , Jin Han , Xiangyu Wang , Zhenwei Wei . In-situ reaction monitoring and kinetics study of photochemical reactions by optical focusing inductive electrospray mass spectrometry. Chinese Chemical Letters, 2025, 36(9): 110708-. doi: 10.1016/j.cclet.2024.110708
6. [6]
  Rui Su , Xiaowei Fang , Peng Zeng , Yong Qian , Xuanzhu Li , Huiyu Xing , Jiamei Lin , Jiaquan Xu . Mass spectrometry for non-destructive detection of the average diameter of micro copper wires. Chinese Chemical Letters, 2025, 36(10): 110748-. doi: 10.1016/j.cclet.2024.110748
7. [7]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
8. [8]
  Yao-Hua Gu , Yu Chen , Qing Li , Neng-Bin Xie , Xue Xing , Jun Xiong , Min Hu , Tian-Zhou Li , Ke-Yu Yuan , Yu Liu , Tang Tang , Fan He , Bi-Feng Yuan . Metabolome profiling by widely-targeted metabolomics and biomarker panel selection using machine-learning for patients in different stages of chronic kidney disease. Chinese Chemical Letters, 2024, 35(11): 109627-. doi: 10.1016/j.cclet.2024.109627
9. [9]
  Yimin Guo , Yiting Luo , Shuwen Hua , Chuan-Fan Ding , Yinghua Yan . Application of magnetic nanomaterials in peptidomics: A review in the past decade. Chinese Chemical Letters, 2025, 36(6): 110070-. doi: 10.1016/j.cclet.2024.110070
10. [10]
  Xiaoli Zhong , Liangsheng Chen , Hao Xu , Tianhang Jiang , Zhengyi Hua , Fancheng Tan , Xiaoya Mao , Ziquan Fan , Zhiwei Li , Jun Zeng , Shu-Hai Lin . Development of a comprehensive computational pipeline for cardiolipin atlas in an intermittent fasting model. Chinese Chemical Letters, 2025, 36(12): 111027-. doi: 10.1016/j.cclet.2025.111027
11. [11]
  Shu-Yi Gu , Tian Feng , Fang-Yin Gang , Si-Yu Yu , Wan Chan , Zhao-Cheng Ma , Yao-Hua Gu , Bi-Feng Yuan . Persistent organic pollutant perfluorooctanoic acid induces alterations in epigenetic modifications of DNA and RNA. Chinese Chemical Letters, 2025, 36(12): 110957-. doi: 10.1016/j.cclet.2025.110957
12. [12]
  Peisi Xie , Jing Chen , Yongjun Xia , Zongwei Cai . MALDI and MALDI-2 mass spectrometry imaging contribute to revealing the alternations in lipid metabolism in germinating soybean seeds. Chinese Chemical Letters, 2025, 36(8): 110595-. doi: 10.1016/j.cclet.2024.110595
13. [13]
  Chao Zhao , Chenyu Gao , Zhiyi Yang , Tianyou Cao , Qian Luo , Zhijun Zhang . Whole brain lipid dyshomeostasis in depressive-like behavior young adult rats: Mapping by mass spectrometry imaging-based spatial omics. Chinese Chemical Letters, 2025, 36(10): 111089-. doi: 10.1016/j.cclet.2025.111089
14. [14]
  Wei Shao , Wanqun Zhang , Pingping Zhu , Wanqun Hu , Qiang Zhou , Weiwei Li , Kaiping Yang , Xisheng Wang . Design and Practice of Ideological and Political Cases in the Course of Instrument Analysis Experiment: Taking the GC-MS Experiment as an Example. University Chemistry, 2024, 39(2): 147-154. doi: 10.3866/PKU.DXHX202309048
15. [15]
  Lu Huang , Jiang Wang , Hong Jiang , Lanfang Chen , Huanwen Chen . On-line determination of selenium compounds in tea infusion by extractive electrospray ionization mass spectrometry combined with a heating reaction device. Chinese Chemical Letters, 2025, 36(1): 109896-. doi: 10.1016/j.cclet.2024.109896
16. [16]
  Yanhua Chen , Xian Ding , Jun Zhou , Zhaoying Wang , Yunhai Bo , Ying Hu , Qingce Zang , Jing Xu , Ruiping Zhang , Jiuming He , Fen Yang , Zeper Abliz . Plasma metabolomics combined with mass spectrometry imaging reveals crosstalk between tumor and plasma in gastric cancer genesis and metastasis. Chinese Chemical Letters, 2025, 36(1): 110351-. doi: 10.1016/j.cclet.2024.110351
17. [17]
  Haiyan Lu , Jiayue Ye , Yiping Wei , Hua Zhang , Konstantin Chingin , Vladimir Frankevich , Huanwen Chen . Tracing molecular margins of lung cancer by internal extractive electrospray ionization mass spectrometry. Chinese Chemical Letters, 2025, 36(2): 110077-. doi: 10.1016/j.cclet.2024.110077
18. [18]
  Wen Su , Siying Liu , Qingfu Zhang , Zhongyan Zhou , Na Wang , Lei Yue . Temperature-controlled electrospray ionization tandem mass spectrometry study on protein/small molecule interaction. Chinese Chemical Letters, 2025, 36(5): 110237-. doi: 10.1016/j.cclet.2024.110237
19. [19]
  Chunmao Yuan , Yanrong Zeng , Lei Huang , Yu Mou , Jun Jin , Ping Yi , Yanmei Li , Xiaojiang Hao . Hymoins A–C, three unusual polycyclic polyprenylated acylphloroglucinols with lipid-lowering activity from Hypericum monogynum. Chinese Chemical Letters, 2025, 36(3): 109859-. doi: 10.1016/j.cclet.2024.109859
20. [20]
  Feng-Qing Huang , Yu Wang , Ji-Wen Wang , Dai Yang , Shi-Lei Wang , Yuan-Ming Fan , Raphael N. Alolga , Lian-Wen Qi . Chemical isotope labeling-assisted liquid chromatography-mass spectrometry enables sensitive and accurate determination of dipeptides and tripeptides in complex biological samples. Chinese Chemical Letters, 2024, 35(11): 109670-. doi: 10.1016/j.cclet.2024.109670

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1229)
HTML views(45)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142