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Communication

Standards-Based UPLC-Q-Exactive Orbitrap MS Systematically Identifies 36 Bioactive Compounds in Ampelopsis grossedentata (Vine Tea)

by
Rongxin Cai
1,2,
Xican Li
1,*,
Chunhou Li
1,
Jiayi Zhu
2,
Jingyuan Zeng
1,
Jianwu Li
3,
Boxu Tang
3,
Zheng Li
4,
Shuqin Liu
1 and
Yan Yan
3
1
School of Chinese Herbal Medicine, Guangzhou University of Chinese Medicine, Guangzhou Higher Education Mega Center, Waihuang East Road No. 232, Guangzhou 510006, China
2
Guangdong Food Industry Institute Co., Ltd., Guangzhou 511442, China
3
School of Pharmacy and Food Science, Zhuhai College Jilin University, Zhuhai 519040, China
4
College of Information Science and Engineering, Hunan Normal University, Changsha 410006, China
*
Author to whom correspondence should be addressed.
Separations 2022, 9(11), 329; https://doi.org/10.3390/separations9110329
Submission received: 17 September 2022 / Revised: 5 October 2022 / Accepted: 24 October 2022 / Published: 27 October 2022
(This article belongs to the Section Analysis of Food and Beverages)
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Versions Notes

Abstract

:
Ampelopsis grossedentata (vine tea) has been used as a detoxifying beverage in China for centuries. To systematically identify its bioactive compounds, the study adopted standards-based ultra-high-performance liquid chromatography coupled with quadrupole/electrostatic field orbitrap high-resolution mass spectrometry (UPLC-Q-Exactive Orbitrap MS) analysis. The analysis was conducted under a negative ion model and the data were collected using the Xcalibur 4.1 software package. Based on comparisons with authentic standards, 36 bioactive compounds were putatively identified by four parameters: retention time, molecular ion peak, MS/MS profile, and characteristic fragments. These bioactive compounds include two chromones (noreugenin and 3,5,7-trihydroxychromone), 15 flavonoids (S-eriodictyol, S-naringenin, luteolin, ampelopsin, taxifolin, myricetin, quercetin, viscidulin I, kaempferol, myricetin 3-O-galactoside, myricitrin, avicularin, quercitrin, isorhamnetin-3-O-β-D-glucoside, and afzelin), four phenolic acids (gallic acid, 3,4-dihydroxy-5-methoxybenzoic acid, syringic acid, and ellagic acid), five tea polyphenols (epigallocatechin, epigallocatechin gallate, gallocatechin gallate, epicatechin gallate, and catechin gallate), three chalcones (phloridzin, phloretin, and naringenin chalcone), one stilbene (polydatin), two lipids (myristic acid and ethyl stearate), one sugar (D-gluconic acid), one amino acid (L-tryptophan), one triterpenoid (oleanolic acid) and one alkaloid (jervine). Notably, the jervine identification is the first report regarding the occurrence of alkaloid in the plant. Two chromones may be the parent skeleton to biosynthesize the flavonoid in A. grossedentata.

1. Introduction

Ampelopsis grossedentata is distributed in southern China (especially Hubei, Hunan, Guangxi, Guangdong and Fujian) and other countries [1]. Its dried tender leaf is called “Vine tea” or “Berry tea” in Chinese [2,3,4] (Figure 1). The tea has been used as a detoxifying beverage by China’s Tujia population for many years. In 2013, it was approved by Chinese authorities as an edible material [5]. With the onset of the COVID-19 pandemic, the tea has become widely consumed by Chinese people (including the Han population) to enhance virus prevention measures.
Two years into the pandemic, vine tea was reported to be able to inhibit SARS-CoV-2 virus in vivo, and the antivirus effect was suggested to be attributed to the presence of flavonoids [6]. This is because these flavonoids usually contain pyrogallol moiety, and thus can be easily oxidized into ortho-quinone to covalently bind the active domain of the SARS-CoV-23CLpro enzyme [2,6]. If so, the previous conclusion that the bioactivity originates from flavonoids may be incorrect [6]. This is because other phenolics may also contain pyrogallol moiety, and thus play a role in the inhibition of SARS-CoV-2.
According to the Folin–Ciocalteu assay, vine tea has twice the total phenolic level of green tea, and thus the highest of all non-Camellia teas and Camellia teas [2]. As of now, scientists have identified at least 10 phenolics from vine tea, including ampelopsin (dihydromyricetin) [5,7,8,9], myricetin [6,10], taxifolin [6], myricetin 3-O-rhamnoside [10], 5,7,8,3,4-pentahydroxyisoflavone [10], dihydroquercetin [10], 6,8-dihydroxykaempferol [10], myricitrin [6], isodihydromyricetin [6] and ellagic acid glucoside [10]. Nevertheless, these are insufficient to characterize the phenolics in vine tea. This is because other phenolics may also comprise pyrogallol moiety, such as tea polyphenols [11,12].
This study tried to use ultra-high-performance liquid chromatography coupled with quadrupole electrostatic field orbitrap high-resolution mass spectrometry (UPLC-Q-Exactive Orbitrap MS), a leading-edge technology, to systematically identify various compounds in vine tea. The UPLC-Q-Exactive Orbitrap MS can obtain the m/z values via rapid scanning, and the MS spectra of all compounds can be recorded in the total ion chromatogram (TIC). Therefore, it can offer systematic information regarding bioactive compounds. This, of course, is much more effective than the conventional LC-MS, HPLC or LC-ESI-Q-TOF/MS [2,9,10].
UPLC-Q-Exactive Orbitrap MS identification should be assessed according to authentic standards. However, previous UPLC-Q-Exactive Orbitrap MS users have not established a library of authentic standards for identification, and thus can provide only tentative identification results [13]. The present study, however, has already established a standards library covering various bioactive compounds. As a result, it can systematically identify different types of bioactive compounds. Through comparison with authentic standards, the bioactive compounds can be putatively identified. This standards-based UPLC-Q-Exactive Orbitrap MS strategy can provide reliable information regarding the systematical identification of A. grossedentata. Furthermore, this information can help us to understand the beneficial effects of vine tea [1,14,15].

2. Results and Discussion

In the study, a TIC diagram was obtained using Xcalibur 4.1 software (Figure 2). The corresponding retention time (R.T.), [M-H] peak, mass error and fragments were listed in Table 1. The putative identification was achieved via multiple comparisons with the corresponding authentic standards. The parameters included R.T. value, molecular ion peak, MS/MS profile and characteristic fragments. Through these comparisons, 36 bioactive compounds were putatively identified. They are listed in Figure 3. One compound, ampelopsin, was identified from evidence set out in Figure 4 and Figure 5.
Table
Table 1. The main experimental results of 36 putatively identified bioactive compounds.
Table 1. The main experimental results of 36 putatively identified bioactive compounds.
NoNameR.T.
min		Formula[M-H]
m/z		Fragments
m/z		Error (ppm)Activity or Application
1D-gluconic acid0.51C6H12O7195.0501177.0395, 159.0287, 129.0182, 111.0079, 99.0075, 75.0075−4.25metabolism [16]
2gallic acid0.87C7H6O5169.0132125.0232, 107.0127, 97.0283, 83.1264, 79.0176, 69.0333−4.68anticancer, antioxidant [17,18],
3L-tryptophan1.75C11H12N2O2203.0817186.0554, 159.0917, 142.0652, 130.0647, 116.0494, 74.0234−3.33metabolism [19]
43,4-dihydroxy-5-methoxybenzoic acid2.19C8H8O5183.0289168.0053, 139.0389, 124.0154, 107.0128, 95.0127−4.88anticancer [20]
5epigallocatechin2.75C15H14O7305.0663219.0663, 179.0334, 167.0336, 147.0441, 137.0229, 125.0232, 109.0282, 96.9587, 81.0332−0.41nutrition [21]
6ampelopsin4.46C15H12O8319.0457301.0346, 257.0448, 193.0134, 175.0027, 151.0056, 137.0223, 125.0233−1.88cytoprotection [3,22,23]
7syringic acid6.55C9H10O5198.1730182.0210, 166.9976, 153.0545, 138.0311, 123.0076, 106.0051, 95.0126, 78.9576, 67.0176−3.57antioxidant [24]
8epigallocatechin gallate7.98C22H18O11457.0768331.0469, 305.0669, 287.0564, 219.0647, 193.0135, 169.0132, 125.0233, 109.0284−0.45antioxidant [12,18]
93,5,7-trihydroxychromone7.64C9H6O5193.0100175.0026, 165.0183, 147.0076, 137.0233, 121.0283, 109.0283, 91.0177, 67.0177−4.34antioxidant [25]
10gallocatechin gallate7.99C22H18O11457.0761331.0454, 305.06659, 251.0342, 193.0135, 169.0131, 137.0234, 125.0232−0.25antioxidant [12]
11taxifolin8.57C15H12O7303.0511285.0403, 259.0609, 241.0499, 217.0498, 199.0396, 175.0391, 150.0313, 125.0232−0.42cytoprotection [26,27]
12epicatechin gallate8.64C22H18O10441.0821289.0716, 203.0705, 169.0132, 137.0231, 125.0233, 109.0283, 97.0281−0.25antioxidant [28,29]
13polydatin8.70C20H22O8389.1719253.6727, 227.0705, 185.0597, 159.0806, 143.0491, 115.0541−0.43nutrition [30]
14catechin gallate8.85C22H18O10441.0837331.0442, 289.0718, 245.0455, 203.0705, 169.0132, 125.0233, 109.0284−0.39cytoprotection [12]
15myricetin 3-O-galactoside8.85C21H20O13479.0821316.0218, 287.0194, 271.0244, 242.0214, 214.0264, 185.0235, 151.0025, 124.0154−0,72osteomodulation [31]
16myricitrin9.30C21H20O12463.0877316.0218, 287.0195, 271.0244, 259.0245, 242.0211, 214.0264, 185.0235, 151.0025, 124.0154−0.34anti-inflammation [32,33]
17ellagic acid9.45C14H6O8300.9986283.9958, 257.0088, 229.0133, 200.0107, 172.0155, 145.0284, 133.0283, 117.0334−0.59antioxidant [34]
18avicularin9.72C20H18O11433.0772300.0271, 271.0244, 255.0293, 243.0293, 227.0345, 199.0393, 171.0441, 135.0077−1.25antidiabetic [35]
19myricetin9.83C15H10O8317.0296288.0235, 271.0247, 227.0345, 178.9976, 151.0026, 137.0233, 117.0333, 109.0283, 83.0125, 65.0020−1.11antioxidant [36,37]
20phloridzin9.95C21H24O10435.1314273.0766, 229.0867, 179.0339, 167.0398, 151.0024, 123.0440, 93.0333, 81.0333−0.63anti-inflammation [38]
21quercitrin10.01C21H20O11447.0926300.0269, 271.0244, 255.0293, 243.0290, 199.0391, 187.0390, 171.0441, 151.0026, 121.0284, 109.0283−0.59anti-inflammation [39,40,41]
22noreugenin10.05C10H8O4191.0341176.0106, 163.0386, 151.0021, 147.0439, 132.0205, 119.0490, 105.0333, 81.0333, 63.0227−4.19healthcare [42]
23isorhamnetin-3-O-β-D-Glucoside10.07C22H22O12477.1029315.0144, 299.0193, 271.0246, 243.0293, 215.0340, 187.0392, 143.0491, 131.0489−0.89metabolomics [43]
24S-eriodictyol10.28C15H12O6287.0561259.0245, 203.0341, 151.0026, 135.0441, 125.0232, 117.0332, 107.0127, 83.0126, 65.0021−0.28antiobesity [44]
25afzelin10.52C21H20O10431.0976285.0401, 255.0294, 227.0342, 211.0392, 199.0392, 183.0441, 167.0492, 155.0492, 107.0126−0.59renoprotection [45]
26quercetin10.68C15H10O7301.0347245.0460, 227.0339, 211.0396, 187.0395, 178.9976, 151.0026, 145.0283, 139.0391, 121.0283, 107.01262−0.74antiferroptosis [46]
27viscidulin I10.69C15H10O7301.0347273.0392, 227.0339, 211.0396, 178.9976, 151.0029, 121.0283, 107.0126, 93.0333, 83.0125, 65.0020−0.74glucosidase inhibitor [47]
28S-naringenin10.90C15H12O5271.0609187.0388, 177.0185, 151.0026, 119.0491, 107.0126, 93.0333, 83.0126−0.27antioxidant [48,49]
29naringenin chalcone10.90C15H12O5271.0609227.0706, 187.0388, 177.0185, 165.0188, 151.0026, 119.0491, 107.0126, 83.0126−0.27anti-inflammatory [50]
30luteolin10.92C15H10O6285.0401267.0288, 241.0497, 199.0397, 175.0390, 151.0026, 133.0283, 121.0284, 107.0125−0.51cytoprotection [51,52]
31phloretin11.06C15H14O5273.0766229.0863, 189.0551, 179.0337, 167.0339, 151.0027, 119.0491, 107.0490, 81.03320.31antimicrobial [53]
32kaempferol11.33C15H10O6285.0402255.0307, 239.0342, 211.0390, 183.0441, 159.0442, 143.0491, 117.0334, 93.0333−0.19anti-inflammatory [54,55]
33jervine12.33C27H39NO3424.2853248.1651, 179.1072, 163.1118, 147.0803, 133.1012, 117.06930.18anti-inflammatory [56,57]
34myristic acid15.12C14H28O2227.2012190.4671, 176.1224, 100.2251, 92.1639, 70.3649, 62.0709−2.51anti-# apoptosis [58]
35oleanolic acid15.20C30H48O3455.3530407.3330, 128.5021, 84.7155, 75.67210.58anticancer [59]
36ethyl stearate16.19C20H40O2311.1685293.2842, 197.0269, 183.0112, 155.9873, 133.0649, 119.0491, 79.9561−0.55neuroprotection [60]
Note: The original MS spectra and identification process were detailed in Supplementary Files S1–S36. The m/z value in bold refers to the characteristic fragments. Peaks with m/z < 50 were still found by the Xcalibur 4.1 software package, despite the scan mode range being set to m/z 100–1200 in the mass spectra.
As seen in Figure 3, the 36 bioactive compounds (1–36) can be classified into 11 types: chromone, flavonoid, phenolic acid, tea polyphenol, chalcone, stilbene, lipid, sugar, amino acid, triterpenoid and alkaloid. The flavonoids, however, can be further classified into two subtypes: one was flavone; while another was flavonol (including flavonol glucoside). Interestingly, the parent skeleton of flavone was actually noreugenin (22), while the parent skeleton of flavonol was 3,5,7-trihydroxychromone (9). This means that the plant A. grossedentata may utilize two chromones as parents to biosynthesize the corresponding flavones and flavonols.
The characteristic compound of A. grossedentata is ampelopsin (dihydromyricetin). Ampelopsin was presumed to have four stereoisomers, (2R, 3R; 2R, 3S; 2S, 3R; 2S, 3S) [4]. However, the naturally occurring ampelopsin has only one stereo-configuration, 2R, 3R. Therefore, peak 6 was identified as ampelopsin (dihydromyricetin).
Structurally, chromone, flavonoid, phenolic acid, tea polyphenol, chalcone and stilbene comprised phenolic OH group in their molecules [61]. Therefore, they can also be considered as total phenolics and are responsible for the high level of total phenolics in vine tea. Among these total phenolics, at least nine bioactive phenolics contained pyrogallol moiety, including ampelopsin (6), myricetin (19), myricetin 3-O-galactoside (15), myricitrin (16), epigallocatechin (EGC, 5), epigallocatechin gallate (EGG, 8), gallocatechin gallate (GCG, 10), epicatechin gallate (ECG, 12) and catechin gallate (CG, 14). This implies that there may be eight bioactive phenolics that trigger SARS-CoV-2 inhibitory action, in addition to ampelopsin (6), the main bioactive compound [6].
In addition to phenolics, an alkaloid jervine (33) was successfully identified in the study. This, of course, is an impressive finding. The is because (1) alkaloids are known to possess strong bioactivity. In fact, jervine was reported to possess anti-tumor, anti-inflammatory and cytotoxic effects [56,62,63]. (2) The previous studies have not found alkaloids (e.g., caffeine) [4,5].
As mentioned above, the detection of the alkaloid jervine was based on a negative model in the UPLC-Q-Exactive Orbitrap MS analysis. In order to try to find more alkaloids, the study also conducted a positive-model analysis. However, no other alkaloid or other bioactive compounds were found. This may be because positive models are not suitable for identifying bioactive compounds in vine tea. Because of this, the study did not provide positive experimental results.
Nevertheless, such standards-based UPLC-Q-Exactive Orbitrap MS systematic identification has offered much more information regarding bioactive compounds than any analysis methods used previously. Information about bioactive compounds can help us to understand the metabolomics of A. grossedentata. On the other hand, the systematic identification of these bioactive compounds can also help us to understand the pharmacological effects (particularly the detoxifying effect) of vine tea. More importantly, it may facilitate a standard of quality controls for vine tea.

3. Materials and Methods

3.1. Plants, Materials and Chemicals

Vine tea (Q/ZSHK 00015) was purchased from Nonglian Agriculture Developing Co., Ltd. (Enshi, Hubei, China). Gallic acid (C7H6O5, M.W. 170.12, CAS 149-91-7, 98%), taxifolin (C15H12O7, M.W. 304.25, CAS 480-18-2, 98%), myricetin 3-O-galactoside (C21H20O13, M.W. 480.37, CAS 15648-86-9, 98%), avicularin (C20H18O11, M.W. 434.35, CAS 572-30-5, 98%), phloridzin (C21H24O10, M.W. 436.41, CAS 60-81-1, 98%), quercitrin (C21H20O11, M.W. 448.38, CAS 522-12-3, 98%) and jervine (C27H39NO3, M.W. 425.61, CAS 469-59-0, 98%) were obtained from Biopurify Phytochemicals, Ltd. (Chengdu, China). L-Tryptophan (C11H12N2O2, M.W. 204.23, CAS 73-22-3, 98%) and 3,4-dihydroxy-5-methoxybenzoic acid (C8H8O5, M.W. 184.15 CAS 3934-84-7, 98%) were from J&K Scientific Co., Ltd. (Beijing, China). Epigallocatechin (C15H14O7, M.W. 306.27, CAS 970-74-1, 98%), epigallocatechin gallate (C22H18O11, M.W. 458.38, CAS 989-51-5, 98%), gallocatechin gallate (C22H18O11, M.W. 458.37, CAS 4233-96-9, 98%), polydatin (C20H22O8, M.W. 390.39, CAS 27208-80-6, 98%), epicatechin gallate (C22H18O10, M.W. 442.37, CAS 1257-08-5, 98%), quercetin (C15H10O7, M.W. 302.23, CAS 117-39-5, 98%), S-naringenin (C15H12O5, M.W. 272.25, CAS 480-41-1, 98%) and phloretin (C15H14O5, M.W. 274.27, CAS 60-82-2, 98%) were purchased from Sichuan Weikeqi Biological Technology Co., Ltd. (Chengdu, China). Dihydromyricetin (C15H12O8, M.W. 320.26, CAS 27200-12-0, 98%), myricitrin (C21H20O12, M.W. 464.38, CAS 17912-87-7, 98%), isorhamnetin-3-O-β-D-glucoside (C22H22O12, M.W. 478.41, CAS 5041-82-7, 98%), S-eriodictyol (C15H12O6, M.W. 288.25, CAS 552-58-9, 98%), viscidulin I (C15H10O7, M.W. 302.24, CAS 92519-95-4, 98%), luteolin (C15H10O6, M.W. 286.24, CAS 491-70-3, 98%), noreugenin (C10H8O4, M.W. 192.17, CAS 1013-69-0, 98%) and 3,5,7-trihydroxychromone (C9H6O5, M.W.194.14, CAS 31721-95-6, 98%) were purchased from BioBioPha Co., Ltd. (Kunming, China). Catechin gallate (C22H18O10, M.W. 442.38, CAS 130405-40-2, 98%), ellagic acid (C14H6O8, M.W. 302.28, CAS 476-66-4, 98%), myricetin (C15H10O8, M.W. 318.24, CAS 529-44-2, 98%), naringenin chalcone (C15H12O5, M.W. 272.25, CAS 73692-50-9, 98%), afzelin (C21H20O10, M.W. 432.38, CAS 482-39-3, 98%) and kaempferol (C15H10O6, M.W. 286.24, CAS 520-18-3, 98%) were obtained from Chengdu Alfa Biotech. Ltd. (Chengdu, China). Ethyl stearate (C20H40O2, M.W. 312.53, CAS 111-61-5, 98%), D-gluconic acid (C6H11O7, M.W.195.15, CAS 526-95-4, 98%), syringic acid (C9H10O5, M.W.197.17, CAS 530-57-4, 98%), oleanolic acid (C30H48O3, M.W. 450.670, CAS 508-02-1, 98%) and myristic acid (C14H28O2, M.W. 228.37, CAS 544-63-8, 98%) were from TCI Chemical Co. (Shanghai, China). Methanol and water were of mass spectra purity grade. All other reagents used in this study were purchased as analytical grade from the Guangzhou Chemical Reagent Factory (Guangzhou, China).

3.2. Preparation of Lyophilized Aqueous Extract of Vine Tea

According to the previous method [64,65], the lyophilized aqueous extract of vine tea was prepared through four steps: decoction, filtration, concentration and lyophilization. Subsequently, the lyophilized aqueous extract was redissolved in methanol and filtered through a 0.45 μm membrane, in line with the method [66,67]. The whole preparation process of lyophilized aqueous extract of vine tea is summarized in Figure 6.

3.3. UPLC-Q-Exactive Orbitrap MS Analysis and Data Acquisition

3.3.1. Analysis Apparatus and Conditions

The extract sample solution (~30 mg/mL, Figure 6B) was analyzed using an ultraperformance liquid chromatography–tandem mass (UPLC-Q-Exactive Orbitrap MS) spectrometer. The spectrometer was combined with quadrupole ion selection and Orbitrap high-resolution scanning (Thermo Fisher Scientific, Waltham, MA, USA). The chromatographic separation was carried out on an Accucore RP-MS LC C18 column (100 mm × 2.1 mm, 2.6 μm, Thermo Fisher), operating at a flow rate of 0.4 mL/ min throughout the gradient. The column temperature was 40 °C, and the injection volume was 3 uL. Eluent A was 0.1% formic acid in water, and eluent B was methanol. The ultraperformance liquid chromatography was conducted under the following conditions: 0–5 min, 10% B; 5–14.5 min, 10–100% B; 14.5–16 min, 100% B; in 16.1min, switched to 10% B and kept up to 4 min to equilibrate the system.
For the MS analysis, the Q-Exactive Orbitrap mass spectrometer was combined with heat electrospray ionization (HEST) and operated in full scan mode ranged m/z 100–1200. The auxiliary gas, sheath gas, and sweep gas were set to flow rates of 10, 40 and 0 (arbitrary units), respectively. The spray voltage was set at 4.5 kV under negative mode. Both the auxiliary gas heater and capillary were set at 450°C. Nitrogen was used for spray stabilization and the damping gas in the C-trap. The analysis was performed in full scan mode with a negative ion swing. The full MS resolution was 70,000 and dd-MS2 was 17,500, while the AGC target was set as 2 × 105. The stepped NCE (normalized collision energy) was set to 20, 50 and 90 V for MS/MS acquisition.

3.3.2. Software, Data Acquisition and Putative Identification

All the data operation, acquisition and analysis was controlled by the Xcalibur 4.1 package, which comprised a TraceFinder General Quan (Thermo Fisher Scientific Inc., Waltham, MA, USA). The original UPLC-Q-Exactive Orbitrap MS data of each sample were exported, and their background was subtracted from mass spectrum data of the blank solvent using Xcalibur for negative ion data. The processed data were then imported to TraceFinder General Quan to extract peaks and align chromatograms manually. The processing parameters were as follows. Mass range: 100–1200 Da; mass tolerance: 5 ppm; S/N threshold: 5; RT Window Override [sec]: 10; minimum number of fragments: 4; isotopic pattern fit threshold: 90%. The relative atomic masses of isotopic atoms are C (12.0000), H (1.007825), O (15.994915), and N (14.003074) [68]. Then, all the aligned MS data of vine tea samples were obtained without interfering peaks.
Using the Xcalibur 4.1, the mass spectrums and corresponding top 5 secondary spectrum were screened and checked by comparing the detected formula and MS fragments with the compound library of authentic standards. Then their structures were putatively identified by comparing with the aforementioned four parameters: retention time, molecular ion peak, MS/MS profile and characteristic fragments.

4. Conclusions

Through systematic identification by a standards-based UPLC-Q-Exactive Orbitrap MS strategy, Ampelopsis grossedentata (vine tea) is shown to comprise 36 bioactive compounds, including two chromones (noreugenin and 3,5,7-trihydroxychromone), 15 flavonoids (S-eriodictyol, S-naringenin, luteolin, ampelopsin, taxifolin, myricetin, quercetin, viscidulin I, kaempferol, myricetin 3-O-galactoside, myricitrin, avicularin, quercitrin, isorhamnetin-3-O-β-D-glucoside and afzelin), four phenolic acids (gallic acid, 3,4-dihydroxy-5-methoxybenzoic acid, syringic acid and ellagic acid), five tea polyphenols (epigallocatechin, epigallocatechin gallate, gallocatechin gallate, epicatechin gallate and catechin gallate), three chalcones (phloridzin, phloretin and naringenin chalcone), one stilbene (polydatin), two lipids (myristic acid and ethyl stearate), one sugar (D-gluconic acid), one amino acid (L-tryptophan), one triterpenoid (oleanolic acid) and one alkaloid (jervine). Notably, the jervine identification is the first report of alkaloid in the plant. Two chromones are presumed to comprise the parent skeleton of flavonoid biosynthesis in A. grossedentata.

Supplementary Materials

The following supplementary materials can be downloaded at: https://www.mdpi.com/article/10.3390/separations9110329/s1. Supplementary Files S1–S36: UPLC-Q-Orbitrap-MS spectra and identification of 1–36.

Author Contributions

Conceptualization, X.L., J.L., and Y.Y.; methodology, X.L. and R.C.; software, R.C., Z.L.; validation, B.T.; formal analysis, R.C., C.L., J.Z. (Jiayi Zhu), J.Z. (Jingyuan Zeng); investigation, R.C., C.L.; resources, J.L. and B.T.; data curation, S.L.; writing—original draft preparation, X.L. and R.C.; writing—review and editing, X.L.; supervision, X.L. and Y.Y.; funding acquisition, Y.Y. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by Undergraduate Innovation and Entrepreneurship Training Program of Zhuhai College of Science and Technology (10201126).

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

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Separations 09 00329 g001 550
Figure 1. A photo of Ampelopsis grossedentata. (A) Fresh tender leaf; (B) dried tender leaf (vine tea or berry tea).
Figure 1. A photo of Ampelopsis grossedentata. (A) Fresh tender leaf; (B) dried tender leaf (vine tea or berry tea).
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Figure 2. The total ion chromatogram (TIC) of vine tea in the UPLC-Q-Orbitrap-MS analysis.
Figure 2. The total ion chromatogram (TIC) of vine tea in the UPLC-Q-Orbitrap-MS analysis.
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Figure 3. The names and structures of 36 putatively identified bioactive compounds in vine tea. The identification process was detailed in Supplementary Files S1–S36. Compound 35 was at trace level.
Figure 3. The names and structures of 36 putatively identified bioactive compounds in vine tea. The identification process was detailed in Supplementary Files S1–S36. Compound 35 was at trace level.
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Figure 4. The typical chromatographic profile of standard ampelopsin (upper) and its MS/MS fragments (below).
Figure 4. The typical chromatographic profile of standard ampelopsin (upper) and its MS/MS fragments (below).
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Figure 5. The typical MS/MS spectra of R.T. 4.54 min peak from the lyophilized aqueous extract of vine tea (upper) and the proposed ampelopsin elucidation (below). The m/z values in purple are the calculated ones. The m/z calculation was based on the relative atomic masses of C (12.0000), H (1.007825), O (15.994915), and N (14.003074).
Figure 5. The typical MS/MS spectra of R.T. 4.54 min peak from the lyophilized aqueous extract of vine tea (upper) and the proposed ampelopsin elucidation (below). The m/z values in purple are the calculated ones. The m/z calculation was based on the relative atomic masses of C (12.0000), H (1.007825), O (15.994915), and N (14.003074).
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Figure 6. Preparation of lyophilized aqueous extract of vine tea (A) and its sample solution (B).
Figure 6. Preparation of lyophilized aqueous extract of vine tea (A) and its sample solution (B).
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Cai, R.; Li, X.; Li, C.; Zhu, J.; Zeng, J.; Li, J.; Tang, B.; Li, Z.; Liu, S.; Yan, Y. Standards-Based UPLC-Q-Exactive Orbitrap MS Systematically Identifies 36 Bioactive Compounds in Ampelopsis grossedentata (Vine Tea). Separations 2022, 9, 329. https://doi.org/10.3390/separations9110329

AMA Style

Cai R, Li X, Li C, Zhu J, Zeng J, Li J, Tang B, Li Z, Liu S, Yan Y. Standards-Based UPLC-Q-Exactive Orbitrap MS Systematically Identifies 36 Bioactive Compounds in Ampelopsis grossedentata (Vine Tea). Separations. 2022; 9(11):329. https://doi.org/10.3390/separations9110329

Chicago/Turabian Style

Cai, Rongxin, Xican Li, Chunhou Li, Jiayi Zhu, Jingyuan Zeng, Jianwu Li, Boxu Tang, Zheng Li, Shuqin Liu, and Yan Yan. 2022. "Standards-Based UPLC-Q-Exactive Orbitrap MS Systematically Identifies 36 Bioactive Compounds in Ampelopsis grossedentata (Vine Tea)" Separations 9, no. 11: 329. https://doi.org/10.3390/separations9110329

APA Style

Cai, R., Li, X., Li, C., Zhu, J., Zeng, J., Li, J., Tang, B., Li, Z., Liu, S., & Yan, Y. (2022). Standards-Based UPLC-Q-Exactive Orbitrap MS Systematically Identifies 36 Bioactive Compounds in Ampelopsis grossedentata (Vine Tea). Separations, 9(11), 329. https://doi.org/10.3390/separations9110329

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