Citation: Shin-ichi Kawano, Yusuke Inohana, Yuki Hashi, Jin-Ming Lin. Analysis of keto-enol tautomers of curcumin by liquid chromatography/mass spectrometry[J]. Chinese Chemical Letters, ;2013, 24(8): 685-687. shu

Analysis of keto-enol tautomers of curcumin by liquid chromatography/mass spectrometry

1.
a Department of Chemistry, Beijing Key Laboratory of Microanalytical Methods and Instrumentation, Tsinghua University, Beijing 100084, China;
b Shimadzu Global COE for Application & Technical Development, Shimadzu (China) Co.
b Shimadzu Global COE for Application & Technical Development, Shimadzu (China) Co., Ltd., Shanghai 200052, China;
3.
c Global Application Development Center, Shimadzu Corporation, Kyoto 604-8511, Japan

Corresponding author: Jin-Ming Lin,
Received Date: 4 March 2013
Available Online: 23 April 2013

Keto-enol tautomers of curcumin were confirmed by reversed-phase liquid chromatography (RPLC)/ hybrid quadrupole ion trap/time-of-flight mass spectrometry (QIT/TOFMS). Tautomers gave different MS/MS spectra in negative mode. Different mass spectra were also obtained by hydrogen/deuterium exchange LC/MS/MS in positive mode. Our results suggest that enol form is the major form in the solution (water/acetonitrile).
- Keto-enol tautomer,
- Curcumin,
- Liquid chromatography/mass spectrometry
1. [1]
  [1] B.B. Aggarwal, K.B. Harikumar, Potential therapeutic effects of curcumin, the antiinflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases, Int. J. Biochem. Cell Biol. 41 (2009) 40-59.
2. [2]
  [2] R.A. Sharma, A.J. Gescher, W.P. Steward, Curcumin: the story so far, Eur. J. Cancer 41 (2005) 1955-1968.
3. [3]
  [3] S. Bengmark, M.D. Mesa, A. Gil, Plant-derived health: the effect of turmeric and curcuminoids, Nutr. Hosp. 24 (2009) 273-281.
4. [4]
  [4] K. Balasubramanian, Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease, J. Agric. Food Chem. 54 (2006) 3512-3520.
5. [5]
  [5] H. Hatcher, R. Planalp, J. Cho, F.M. Torti, S.V. Torti, Curcumin: from ancient medicine to current clinical trials, Cell. Mol. Life Sci. 65 (2008) 1631-1652.
6. [6]
  [6] R.F. Tayyem, D.D. Heath, W.K. Al-Delaimy, C.L. Rock, Curcumin content of turmeric and curry powders, Nutr. Cancer 55 (2006) 126-131.
7. [7]
  [7] W. Wichitnithad, N. Jongaroonngamsang, S. Pummangura, P. Rojsitthisak, A simple isocratic HPLC method for the simultaneous determination of curcuminoids in commercial turmeric extracts, Phytochem. Anal. 20 (2009) 314-319.
8. [8]
  [8] J. Zhang, S. Jinnai, R. Ikeda, M. Wada, S. Hayashida, K. Nakashima, A simple HPLCfluorescence method for quantitation of curcuminoids and its application to turmeric products, Anal. Sci. 25 (2009) 385-388.
9. [9]
  [9] A. Liu, H. Lou, L. Zhao, P. Fan, Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin, J. Pharm. Biomed. Anal. 40 (2006) 720-727.
10. [10]
  [10] K. Yang, L. Lin, T. Tseng, S. Wang, T. Tsai, Oral bioavailability of curcumin in rat and the herbal analysis from Curcuma longa by LC-MS/MS, J. Chromatogr. B 853 (2007) 183-189.
11. [11]
  [11] J. Li, Y. Jiang, J. Wen, G. Fan, Y. Wu, C. Zhang, A rapid and simple HPLC method for the determination of curcumin in rat plasma: assay development, validation and application to a pharmacokinetic study of curcumin liposome, Biomed. Chromatogr. 23 (2009) 1201-1207.
12. [12]
  [12] J.R. Fuchs, B. Pandit, D. Bhasin, et al., Structure-activity relationship studies of curcumin analogues, Bioorg. Med. Chem. Lett. 19 (2009) 2065-2069.
13. [13]
  [13] D. Yanagisawa, N. Shirai, T. Amatsubo, et al., Relationship between the tautomeric structures of curcumin derivatives and their Ab-binding activities in the context of the therapies for Alzheimer's disease, Biomaterials 31 (2010) 4179-4185.
14. [14]
  [14] T.J. Novak, R. Helmy, I. Santos, Liquid chromatography-mass spectrometry using the hydrogen/deuterium exchange reaction as a tool for impurity identification in pharmaceutical process development, J. Chromatogr. B 825 (2005) 161-168.
15. [15]
  [15] D.Q. Liu, L. Wu, M. Sun, P.A. MacGregor, On-line H/D exchange LC-MS strategy for structural elucidation of pharmaceutical impurities, J. Pharm. Biomed. Anal. 44 (2007) 320-329.
16. [16]
  [16] T.M. Kolev, E.A. Velcheva, B.A. Stamboliyska, M. Spiteller, DFT and experimental studies of the structure and vibrational spectra of curcumin, Int. J. Quantum Chem. 102 (2005) 1069-1079.
17. [17]
  [17] H. Jiang, Á. Somogyi, N.E. Jacobsen, B.N. Timmermann, D.R. Gang, Analysis of curcuminoids by positive and negative electrospray ionization and tandem mass spectrometry, Rapid Commun. Mass Spectrom. 20 (2006) 1001-1012.
18. [18]
  [18] F. Payton, P. Sandusky, W.L. Alworth, NMR study of the solution structure of curcumin, J. Nat. Prod. 70 (2007) 143-146.
1. [1]
  Ying Xu , Chengying Shen , Hailong Yuan , Wei Wu . Mapping multiple phases in curcumin binary solid dispersions by fluorescence contrasting. Chinese Chemical Letters, 2024, 35(9): 109324-. doi: 10.1016/j.cclet.2023.109324
2. [2]
  Haijiao Li , Mingzu Zhang , Jinlin He , Jian Liu , Xingwei Sun , Peihong Ni . Synthesis of curcumin polyprodrug via click chemistry and construction of dual-drug-loaded nano platform for highly efficient tumor treatment. Chinese Chemical Letters, 2025, 36(8): 110615-. doi: 10.1016/j.cclet.2024.110615
3. [3]
  Qi Huang , Jun Liao , Jingjing Li , Zhengyan Gu , Xinkang Zhang , Mingxue Sun , Wenqi Meng , Guanchao Mao , Zhipeng Pei , Shanshan Zhang , Songling Li , Chuan Zhang , Yunqin Wang , Jihao Liu , Tingbin Shu , Min Tao , Ying Lu , Kai Xiao , Qingqiang Xu , Jincai Lu . Curcumin-loaded ceria nanoenzymes for dual-action suppression of inflammation and alleviation of oxidative damage in the treatment of acute lung injury. Chinese Chemical Letters, 2025, 36(4): 109914-. doi: 10.1016/j.cclet.2024.109914
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
8. [8]
  Wangyan Hu , Ke Li , Xiangnan Dou , Ning Li , Xiayan Wang . Nano-sized stationary phase packings retained by single-particle frit for microchip liquid chromatography. Chinese Chemical Letters, 2024, 35(4): 108806-. doi: 10.1016/j.cclet.2023.108806
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Haoyang Wang , Ronghao Zhang , Yanlun Ren , Li Zhang . A convenient method for measuring gas-liquid volumetric mass transfer coefficient in micro reactors. Chinese Chemical Letters, 2024, 35(4): 108833-. doi: 10.1016/j.cclet.2023.108833
17. [17]
  Fangqing Zhang , Yu Wang , Zhenda Tan , Yangbin Liu , Lijuan Song , Xiaoming Feng . Catalytic asymmetric inverse-electron-demand Diels–Alder reaction of 2-pyrones with aryl enol ethers. Chinese Chemical Letters, 2025, 36(7): 110581-. doi: 10.1016/j.cclet.2024.110581
18. [18]
  Jindong Hao , Yufen Lv , Shuyue Tian , Chao Ma , Wenxiu Cui , Huilan Yue , Wei Wei , Dong Yi . Additive-free synthesis of β-keto phosphorodithioates via geminal hydro-phosphorodithiolation of sulfoxonium ylides with P₄S₁₀ and alcohols. Chinese Chemical Letters, 2024, 35(9): 109513-. doi: 10.1016/j.cclet.2024.109513
19. [19]
  Xiaoyu Du , Huan Wang . Tailoring mass transfer on electrochemical fixation of air-abundant molecules. Chinese Chemical Letters, 2025, 36(8): 110276-. doi: 10.1016/j.cclet.2024.110276
20. [20]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1100)
HTML views(37)

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