Affiliation:
1. State Key Laboratory of Southwestern Chinese Medicine Resources School of Pharmacy Chengdu University of Traditional Chinese Medicine Chengdu P. R. China
2. Center for Natural Products Research Chengdu Institute of Biology Chinese Academy of Sciences Chengdu P. R. China
3. School of Pharmaceutical Sciences Peking University Beijing P. R. China
4. Department of Functional Food Research Sichuan Jinhong Keyou Biotechnology Co., Ltd Chengdu P. R. China
Abstract
Terpene‐conjugated curcuminoids are conjugates of curcuminoids and bisabolanes in the rhizomes of Curcuma longa L. The fragmentation pathways of known three terpene‐conjugated curcuminoids (bisabolocurcumin‐ether, bisabocurcumin, and demethoxybisabolocurcumin ether) and curcumin, demethoxycurcumin, and bisdemethoxycurcumin were investigated using high‐performance liquid chromatography‐electrospray ionization tandem mass spectrometry in negative mode to rapidly search and discover similar unknown compounds of the acetone fraction of turmeric. Subsequently, compounds 1–3 were founded in the acetone fraction based on molecular weight and above fragmentation pathways (the characteristic fragment ions, the most and second most abundant fragment ions produced in MS2 spectra). Terpecurcumin X (1) and terpecurcumin Y (3) were further separated by liquid chromatography–tandem mass spectrometry guided isolation technique to verify their structures by nuclear magnetic resonance, electrospray ionization high‐resolution mass spectroscopy, ultraviolet and visible spectra and infrared spectra. Interestingly, 1 and 3 were new compounds. The results indicate the feasibility and significant advantages of liquid chromatography–tandem mass spectrometry for the rapid discovery and analysis of new constituents in traditional Chinese medicine. In vitro, Terpene‐conjugated curcuminoids had better nitric oxide inhibitory activity than the other seven curcuminoids (demethoxycurcumin, bisdemethoxycurcumin, curdione, curcumenone, bisacurone, curcumenol, and germacron).
Funder
National Natural Science Foundation of China
Subject
Filtration and Separation,Analytical Chemistry