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Confirmative Structural Annotation for Metabolites of (R)-7,3′-Dihydroxy-4′-methoxy-8-methylflavane, A Natural Sweet Taste Modulator, by Liquid Chromatography-Three-Dimensional Mass Spectrometry
Pengwei, Guan1; Song, Qingqing1; Li, Ting1; Cao, Libo1; Tang, Huiting1; Wang, Yitao2; Tu, Pengfei1; Zheng, Jiao1; Song, Yuelin1; Li, Jun1
2020-10-21
Source PublicationJournal of Agricultural and Food Chemistry
ISSN0021-8561
Volume68Issue:44Pages:12454-12466
Abstract

Flavonoids occupy the largest family of natural products and possess a broad spectrum of health benefits. Their metabolites are sometimes the truly effective molecules in vivo. It is still challenging, however, to unambiguously identify flavonoid metabolites using conventional LC-MS/MS. Herein, we aimed to pursue auxiliary structural clues to m/z values in both MS1 and MS2 spectra through LC coupled to three-dimensional MS (LC-3D MS). MS1, as the first dimension, was in charge of suggesting theoretical molecular formulas, MS2, the as second dimension, was responsible for offering substructures, and exactly, online energy-resolved MS (ER-MS), as the third dimension, provided optimal collision energies (OCEs) that reflected the linkage manners among the substructures. Metabolic characterization of a natural sweet taste modulator, namely, (R)-7,3′-dihydroxy-4′-methoxy-8-methylflavane (DHMMF), was conducted as a proof-of-concept. Extensive efforts, such as full MS1 and MS2 scans on IT-TOF-MS and predictive selected-reaction monitoring mode on Qtrap-MS, were made for in-depth metabolite mining. Seventeen metabolites (M1-M17) were captured from DHMMF-treated biological samples, including 17 (M1-M17), 10 (M4-M9, M11, M13, M14, and M16), and 2 (M5 and M10) metabolites from urine, plasma, and feces, respectively. Their structures were configured by integrating MS1, MS2, and OCE information. Except M10, all metabolites were new compounds. LC-MS/MS-guided chromatographic purification yielded three glucuronyl-conjugated metabolites (M5, M8, and M11), and NMR spectroscopic assays consolidated the structures transmitted from LC-3D MS. Demethylation, glucuronidation, and sulfation occurred as the primary metabolic pathways of DHMMF. Above all, LC-3D MS bridged LC-MS/MS from putatively structural annotation toward confidence-enhanced identification, beyond the metabolite characterization of flavonoids.

Keyword(r)-8-methyl-4′-methoxyl-7,3′-dihydroxylflavane Flavonoids Online Energy-resolved Mass Spectrometry Optimal Collision Energy Regio-isomers
DOI10.1021/acs.jafc.0c05154
URLView the original
Indexed BySCIE ; IC
Language英語English
WOS Research AreaAgriculture ; Food Science & Technology ; Chemistry
WOS SubjectAgriculture, Multidisciplinary ; Chemistry, Applied ; Food Science & Technology
WOS IDWOS:000589379300027
Scopus ID2-s2.0-85095673152
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Cited Times [WOS]:1   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorZheng, Jiao; Song, Yuelin; Li, Jun
Affiliation1.Modern Research Center for Traditional Chinese Medicine, School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, 100029, China
2.State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Taipa, 999078, Macao
Recommended Citation
GB/T 7714
Pengwei, Guan,Song, Qingqing,Li, Ting,et al. Confirmative Structural Annotation for Metabolites of (R)-7,3′-Dihydroxy-4′-methoxy-8-methylflavane, A Natural Sweet Taste Modulator, by Liquid Chromatography-Three-Dimensional Mass Spectrometry[J]. Journal of Agricultural and Food Chemistry,2020,68(44):12454-12466.
APA Pengwei, Guan,Song, Qingqing,Li, Ting,Cao, Libo,Tang, Huiting,Wang, Yitao,Tu, Pengfei,Zheng, Jiao,Song, Yuelin,&Li, Jun.(2020).Confirmative Structural Annotation for Metabolites of (R)-7,3′-Dihydroxy-4′-methoxy-8-methylflavane, A Natural Sweet Taste Modulator, by Liquid Chromatography-Three-Dimensional Mass Spectrometry.Journal of Agricultural and Food Chemistry,68(44),12454-12466.
MLA Pengwei, Guan,et al."Confirmative Structural Annotation for Metabolites of (R)-7,3′-Dihydroxy-4′-methoxy-8-methylflavane, A Natural Sweet Taste Modulator, by Liquid Chromatography-Three-Dimensional Mass Spectrometry".Journal of Agricultural and Food Chemistry 68.44(2020):12454-12466.
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