Journal of Chinese Pharmaceutical Sciences ›› 2014, Vol. 23 ›› Issue (9): 631-641.DOI: 10.5246/jcps.2014.09.081

• Original articles • Previous Articles     Next Articles

Investigations of the fragmentation behavior of 11 isoflavones with ESI-IT-TOF-MSn

Yazhou Zhang1,2, Feng Xu3, Jianye Zhang1, Tao Yi1, Yina Tang1, Jun Xu1, Wanling Peng1, Hubiao Chen1*    

  1. 1. School of Chinese Medicine, Hong Kong Baptist University, Hong Kong Special Administrative Region 999077, China
    2. Guizhou College of Technology, Guiyang 550003, China
    3. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Sciences Center, Beijing 100191, China
  • Received:2014-04-18 Revised:2014-04-30 Online:2014-09-23 Published:2014-05-10
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  • Supported by:
    Hong Kong Baptist University Faculty Research Foundation (Grant No. FRG2/12-13/058), and the Key Program of Guangxi Natural Science Foundation of China (Grant No. 2013-GXNSFBA019187).


The fragmentation behavior of isoflavones was studied using electrospray ionization-ion trap-time of flight mass spectrometry (ESI-IT-TOF-MSn). It was found that the isoflavone glycoside bond was easily broken. The fragmentation occurred mostly on the C-ring, and the fragment ions of A1,3+ produced bythe RDA cracking will predict the hydroxylation replacement on A-ring or B-ring. In addition, four carbonyl groups on the C-ring were fragmented through neutral loss of 28 (-CO). A and B-rings primarily lose substituents which including a neutral losses of 32 (-CH3OH), 16 (-CH4), or 16 (-O), and 18 (-H2O). A-ring in the presence of adjacent hydroxylation, also easily made to be a neutral losses of 28 (-CO) or 18 (-H2O). It is likewise common to see methoxy replaced with a neutral losses of 16 (-CH4) or 32 (-CH3OH) in B-ring, also the hydroxylation on benzene ring can occasionally results with the neutral loss of 28 (-CO).

Key words: Isoflavone, Fragmentation behavior, ESI-IT-TOF-MSn

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