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Identification of Alkaloids in Stephania hainanensis by Liquid Chromatography Coupled with Quadrupole Time-of-flight Mass Spectrometry. 2016

Jiayong He, and Ying Liu, and Yun Kang, and Ping Yang, and Yaqin Wang, and Jixian Guo, and Jianming Huang
Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, 201203, China.

BACKGROUND Plants in the genus Stephania can produce diverse bioactive alkaloids. Stephania hainanensis is a medicinal plant that contains effective alkaloids. However, only 10 alkaloids have been reported in this species. OBJECTIVE To characterise the alkaloids in Stephania hainanensis using liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (LC-QTOF-MS/MS). METHODS An LC-QTOF-MS/MS method was developed for structural characterisation of the alkaloids in Stephania hainanensis. The chromatographic separation was performed on a phenyl column with gradient elution, and the tandem mass spectra were obtained by using an electrospray ionisation (ESI) interface in positive ionisation mode. Compound identification was based on the exact masses, fragmentation pathways, retention behaviours and related botanical biogenesis. RESULTS A total of 37 tetrahydroprotoberberine-, quaternary protoberberine-, aporphine-, proaporphine-, benzylisoquinoline- or bisbenzylisoquinoline-type alkaloids were identified or tentatively identified in a single LC run. Twenty-seven of these alkaloids, including the benzylisoquinoline-type of alkaloids, have not been previously reported in Stephania hainanensis. The possible fragmentation pathways of different types of alkaloids were proposed. Besides the general fragmentations, the characteristic losses of CH3 N = CH2 were observed for the benzylisoquinoline and aporphine alkaloids with two methyl groups on the nitrogen. CONCLUSIONS The LC-QTOF-MS/MS method enabled profiling and rational, but tentative, identification of diverse alkaloids in Stephania hainanensis. The results obtained may be helpful for understanding the bioactivity of S. hainanensis and evaluating the quality of this plant. Copyright © 2016 John Wiley & Sons, Ltd.

UI MeSH Term Description Entries
D010946 Plants, Medicinal Plants whose roots, leaves, seeds, bark, or other constituent parts possess therapeutic, tonic, purgative, curative or other pharmacologic attributes, when administered to man or animals. Herbs, Medicinal,Medicinal Herbs,Healing Plants,Medicinal Plants,Pharmaceutical Plants,Healing Plant,Herb, Medicinal,Medicinal Herb,Medicinal Plant,Pharmaceutical Plant,Plant, Healing,Plant, Medicinal,Plant, Pharmaceutical,Plants, Healing,Plants, Pharmaceutical
D002853 Chromatography, Liquid Chromatographic techniques in which the mobile phase is a liquid. Liquid Chromatography
D000470 Alkaloids Organic nitrogenous bases. Many alkaloids of medical importance occur in the animal and vegetable kingdoms, and some have been synthesized. (Grant & Hackh's Chemical Dictionary, 5th ed) Alkaloid,Plant Alkaloid,Plant Alkaloids,Alkaloid, Plant,Alkaloids, Plant
D001060 Aporphines Dibenzoquinolines derived in plants from (S)-reticuline (BENZYLISOQUINOLINES).
D001600 Berberine Alkaloids A group of related plant alkaloids that contain the BERBERINE heterocyclic ring structure. Berbines,Alkaloids, Berberine
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D044182 Benzylisoquinolines ISOQUINOLINES with a benzyl substituent. Benzyl-Isoquinoline,Benzylisoquinoline,Bis-Benzyl-Isoquinoline,Bis-Benzylisoquinoline,Bisbenzylisoquinoline,Bisbenzylisoquinolines,Benzyl-Isoquinolines,Bis-Benzyl-Isoquinolines,Bis-Benzylisoquinolines,Benzyl Isoquinoline,Benzyl Isoquinolines,Bis Benzyl Isoquinoline,Bis Benzyl Isoquinolines,Bis Benzylisoquinoline,Bis Benzylisoquinolines
D053719 Tandem Mass Spectrometry A mass spectrometry technique using two (MS/MS) or more mass analyzers. With two in tandem, the precursor ions are mass-selected by a first mass analyzer, and focused into a collision region where they are then fragmented into product ions which are then characterized by a second mass analyzer. A variety of techniques are used to separate the compounds, ionize them, and introduce them to the first mass analyzer. For example, for in GC-MS/MS, GAS CHROMATOGRAPHY-MASS SPECTROMETRY is involved in separating relatively small compounds by GAS CHROMATOGRAPHY prior to injecting them into an ionization chamber for the mass selection. Mass Spectrometry-Mass Spectrometry,Mass Spectrometry Mass Spectrometry,Mass Spectrometry, Tandem
D031607 Stephania A plant genus of the family MENISPERMACEAE. Members contain cycleanine. Stephanias

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