Journal
MOLECULES
Volume 24, Issue 24, Pages -Publisher
MDPI
DOI: 10.3390/molecules24244591
Keywords
prenylated flavonoids; Artocarpus heterophyllus; Q-TOF-MS; LTQ-Orbitrap-MS; fragmentation rules; identification
Funding
- National Natural Science Foundation of China [81160509, 81360475]
- Young Scientist Development Program of Jiangxi Province [20142BCB23024]
- Jiangxi provincial natural science fund project [20151BAB205074]
- Double First-class Discipline of Jiangxi Province [JXSYLXK-ZHYAO027, JXSYLXK-ZHYAO064]
- Graduate student innovation special fund project of Jiangxi University of Traditional Chinese Medicine [JZYC19S47]
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In this study, a combination of quadrupole time-of-flight mass spectrometry (Q-TOF-MS) and linear trap quadrupole orbitrap mass spectrometry (LTQ-Orbitrap-MS) was performed to investigate the fragmentation behaviors of prenylated flavonoids (PFs) from Artocarpus plants. Fifteen PFs were selected as the model molecules and divided into five types (groups A-E) according to their structural characteristics in terms of the position and existing form of prenyl substitution in the flavone skeleton. The LTQ-Orbitrap-MSn spectra of the [M - H](-) ions for these compounds provided a wealth of structural information on the five different types of compounds. The main fragmentation pathways of group A were the ortho effect and retro Diels-Alder (RDA), and common losses of C4H10, CO, and CO2. The compounds in group B easily lose C6H12, forming a stable structure of a 1,4-dienyl group, unlike those in group A. The fragmentation pathway for group C is characterized by obvious (1,4)A(-), B-1,4(-) cracking of the C ring. The diagnostic fragmentation for group D is obvious RDA cracking of the C ring and the successive loss of CH3 and H2O in the LTQ-Orbitrap-MSn spectra. Fragmentation with successive loss of CO or CO2, center dot CH3, and CH4 in the LTQ-Orbitrap-MSn spectra formed the characteristics of group E. The summarized fragmentation rules were successfully exploited to identify PFs from Artocarpusheterophyllus, a well-known Artocarpus plant, which led to the identification of a total of 47 PFs in this plant.
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