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Research Article Rapid Identification of Chemical Constituents in Artemisia Argyi Le´Vi

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Research Article Rapid Identification of Chemical Constituents in Artemisia Argyi Le´Vi Hindawi Journal of Food Quality Volume 2021, Article ID 5597327, 7 pages https://doi.org/10.1155/2021/5597327 Research Article Rapid Identification of Chemical Constituents in Artemisia argyi Le´vi. et Vant by UPLC-Q-Exactive-MS/MS Lili Cui ,1,2 Xianzhong Wang ,1,3 Jie Lu ,1 Jing Tian ,1 Li Wang ,1 Jiaojiao Qu ,1 Zhenhua Liu ,1 and Jinfeng Wei 1,4 1National R and D Center for Edible Fungus Processing Technology, Henan University, Kaifeng 475004, Henan, China 2Kaifeng Key Laboratory of Functional Components,Health Food, Henan Province, Kaifeng 475004, China 3Zhumadian Xusheng Agricultural Technology Co.,Ltd., Zhumadian 463800, China 4Minsheng College, Henan University, Kaifeng 475004, Henan, China Correspondence should be addressed to Zhenhua Liu; [email protected] and Jinfeng Wei; weijinfeng20112011@ hotmail.com Received 5 February 2021; Revised 1 April 2021; Accepted 13 April 2021; Published 21 April 2021 Academic Editor: Wei Chen Copyright © 2021 Lili Cui et al. ,is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Artemisia argyi Levi.´ et Vant is a traditional Chinese medicine with a long history, and its buds and seedlings can be used as vegetables. However, the investigations on the chemical constituents of A. argyi are not sufficient. In this paper, ultra-high performance liquid chromatography tandem hybrid quadrupole-orbitrap mass spectrometry (UPLC-Q-Exactive-MS/MS) was used to identify the chemical constituents of A. argyi. ,e Q Exactive mass spectrometer was used to collect MS and MS2 data. Finally, 125 compounds were preliminarily identified in A. argyi by comparing the retention time and accurate molecular weight with standard databases such as MZVault, MZCloud, and BGI Library (self-built standard Library by BGI Co., Ltd), including flavonoids, phenylpropanoids, terpenoids, and organic acids. 1. Introduction oil, flavonoids, terpenoids, phenylpropanoids, organic acids, and steroids. Among them, more than 200 volatile oils from Artemisia argyi Levi.´ et Vant belongs to Asteraceae family, A. argyi leaves have been identified, and 182 nonvolatile widely distributed in China. A. argyi is a traditional Chinese components have been isolated and identified [2, 4]. medicine with a long history, and its buds and seedlings can Pharmacological studies have shown that A. argyi leaves be used as vegetables. According to flora of China, A. argyi has have many pharmacological effects, such as antibacterial, functions of warming menstrual cycle, removing dampness, antiviral, hemostatic, anti-tumor, protecting liver and gall- dispersing cold, hemostasis, anti-inflammation, relieving bladder, and anti-oxidation, relieving cough and asthma, asthma, relieving cough, calming fetus and anti-allergy with analgesia, anti-inflammatory, and immune regulation. whole grass as medicine [1, 2]. According to Chinese Phar- Moxibustion has the effect of warming and dispersing cold macopoeia (2020), Artemisiae argyi folium (A. argyi leaves) and treating all diseases [2, 4–6]. With the development of has minor poison, its nature and flavour are warm, pungent, the health industry, more and more attention has been paid and bitter, and its channel tropism is in liver, spleen, and to the study of A. argyi leaves and moxa [6]. In recent years, kidney. A. argyi leaves have warm meridian to stop bleeding, systematic studies on the chemical constituents of A. argyi disperse cold, and relieve pain and external clearing damp leaves or A. argyi have gradually increased [7, 8]. With the antipruritic effect [3]. mature application of LC-MS/MS technology in the rapid At present, research about chemical constituents of identification of plant and food stuff ingredients [9–11], A. argyi was focused on A. argyi leaves. Research showed that research studies on the rapid analysis of nonvolatile com- the chemical constituents of A. argyi leaves include volatile ponents of A. argyi leaves or A. argyi are gradually increasing 2 Journal of Food Quality [12–15], but there are few identified compounds. Ultra-high 2.5. Chromatographic Conditions. Hypersil GOLD aQ col- performance liquid chromatography tandem hybrid quadru- umn (100 mm × 2.1 mm, 1.9 μm) was used to do LC-MS ex- pole-orbitrap mass spectrometry (UPLC-Q-Exactive-MS/MS) periment. ,e mobile phase was 0.1% formic acid-water (liquid is a new type of liquid chromatography-mass spectrometry A) and 0.1% formic acid-acetonitrile (liquid B). ,e following developed in recent years, which has the characteristics of high gradients were used for elution: 0–2 min 5% B; 2–22 min 5%– resolution, good quality and precision, and strong qualitative 95% B; 22–27 min 95% B; 27.1–30 min 5% B. ,e flow rate was and quantitative ability [16, 17]. Samples can be separated 0.3 mL/min, the column temperature was 40°C, and the in- quickly by ultra-high performance liquid chromatography, and jection volume was 5 μL. accurate molecular weight can be determined by high-reso- lution mass spectrometry to obtain molecular formula of 2.6. Mass Spectrometry Conditions. ,e mass range was compounds. Zhumadian region is abundant with A. argyi; 6 however, research about chemical components of A. argyi from 150–1500, the MS resolution was 70000, the AGC was 1e , Zhumadian region was less. ,erefore, in this study, UPLC-Q- and the maximum injection time was 100 ms. According to the strength of the MS ions, TOP3 was selected for frag- Exactive-MS/MS combined with standard substance database 2 5 was used to rapidly identify the nonvolatile chemical com- mentation. ,e MS resolution was 35000, AGC is 2e , the ponents of A. argyi from Zhumadian region. maximum injection time was 50 ms, and the fragmentation energy were set as 20, 40, and 60 eV. Ion source (ESI) pa- rameter settings: sheath gas flow rate was 40, aux gas flow rate 2. Materials and Methods was 10, spray voltage (|KV|) of positive ion mode was 3.80, spray voltage (|KV|) of negative ion mode was 3.20, ion 2.1. Instrument. Rotary evaporator (N-1300) was purchased capillary temp was 320°C, and aux gas heater temp was 350°C. from EYELA. Ultra-performance liquid chromatograph (Waters 2D UPLC) was purchased from Waters, USA. High- resolution mass spectrometer (Q Exactive) was purchased 2.7. Data Analysis. UPLC-MS/MS technology was used to from ,ermo Fisher Scientific, USA. Hypersil GOLD aQ systematically analyze the chemical constituents of column (100 mm × 2.1 mm, 1.9 μm) was purchased from A. argyi. High-resolution mass spectrometer Q Exactive ,ermo Fisher Scientific, USA. Low temperature high speed (,ermo Fisher Scientific, USA) was used to collect data centrifuge (Centrifuge 5430) was purchased from Eppendorf. in positive and negative ion modes, respectively, to im- Vortex finder (QL-901) was purchased from Qilinbeier In- prove the chemical constituent coverage. Raw mass spectrum strument Manufacturing Co., Ltd. Pure water meter (Milli-Q) data collected by UPLC-MS/MS were imported into Com- was purchased from Integral Millipore Corporation, USA. pound Discoverer 3.1 (,ermo Fisher Scientific, USA) for data processing. It mainly includes peak extraction, retention time correction within and between groups, additive ion 13 2.2. Reagent. d3-Leucine, C9-Phenylalanine, d5-Trypto- merging, missing value filling, background peak labeling, and 13 phan, and C3-Progesterone were used as internal standard. metabolite identification. Finally, the molecular weight, re- Methanol (A454-4) and acetonitrile (A996-4) were both in tention time, peak area, and identification results of the mass grade, which were purchased from ,ermo Fisher compound were derived. ,e compounds were identified by Scientific, USA. Ammonium formate (17843–250G) was ob- comparing the retention time, accurate molecular weight, and tained from Honeywell Fluka, USA. Formic acid MS2 data with standard databases such as MZVault, (50144–50 mL) was obtained from DIMKA, USA. 95% ethanol MZCloud, and BGI Library (self-built standard Library by (20190320) was obtained from Tianjin Fuyu Fine Chemicals BGI Co., Ltd). Co., Ltd. Water was supplied by a pure water meter. 3. Results 2.3. Plants. A. argyi was collected in July 2020 in Wanhei 3.1. Total Ion Chromatogram. Total ion chromatogram of Village, Shangcai County, Zhumadian City, and identified as A. argyi is shown in Figures 1 and 2. the aerial part of A. argyi by professor Li Changqin of Henan University. ,e specimens (No. 2020-08-10) were saved in National Research and Development Center of Edible Fungi 3.2. Identification Results of Chemical Composition. In this Processing Technology, Henan University. study, UPLC-Q-Exactive-MS/MS technology was used to rapidly identify the chemical constituents in A. argyi. ,e identification of compounds was based on the retention 2.4. Preparation of Sample. 10 g of A. argyi powder was time, MS data, and MS2 data compared with the standard accurately weighed and impregnated with 25 times 70% database (MZVault, MZCloud and BGI Library (self-built ethanol for 2 times at room temperature, each time for 2 standard Library by BGI Co., Ltd)). Most flavonoids, phe- days. ,e extraction was filtered, and filtrate was combined nylpropanoids, and organic acids were easily deprotonated and concentrated. ,e extract was added with 70% ethanol and responded in negative ion mode. Most steroids and to 1 g/mL of the original materials and then reserved. 200 μL terpenoids were easily protonated and responded in pos- was sent to BGI Co., Ltd., for chemical composition itive ion mode. ,e identification results are shown in Ta- identification. ble 1. A total of 125 chemical constituents were identified in Journal of Food Quality 3 3.00E + 009 2.50E + 009 2.00E + 009 1.50E + 009 Intensity 1.00E + 009 5.00E + 008 0.00E + 000 0 510 15 20 25 30 Retention time (min) Figure 1: Total ion chromatogram of A.
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