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Identification of Polyphenol Glucuronide Conjugates In molecules Article Identification of Polyphenol Glucuronide Conjugates in Glechoma hederacea var. longituba Hot Water Extracts by High-Performance Liquid Chromatography-Tandem Mass Spectrometry (HPLC-MS/MS) Kun Cho 1 , Yoon-Ji Choi 2 and Yeong Hee Ahn 3,* 1 Center for research equipment, Korea basic science institute, Cheongju 28119, Korea; [email protected] 2 Graduate School of Analytical Science and Technology, Chungnam National University, Daejeon 34134, Korea; [email protected] 3 Department of Biomedical Science, Cheongju University, Cheongju 28160, Korea * Correspondence: [email protected]; Tel.: +82-43-229-8565 Received: 17 September 2020; Accepted: 12 October 2020; Published: 14 October 2020 Abstract: Glechoma hederacea var. longituba (GHL) is one of many herbal plants distributed worldwide and is known to contain various biologically useful antioxidant constituents. GHL has been used in folk remedies for various treatments and as favorable tea beverages. However, research on the precise analysis of ingredients in GHL extracts remains insufficient. In this study, compositional analysis has been conducted on polyphenolic ingredients in GHL hot water extracts. GHL samples collected from growing regions were incubated in hot water at 100 ◦C for 1 h. The polyphenolic constituents in the hot water extracts were analyzed using high performance liquid chromatography-high resolution mass spectrometry (HPLC-HR MS) and tandem mass spectrometry (HPLC-MS/MS) in negative ion mode. As a result, a total of seven compounds were identified as the major polyphenolic constituents. Interestingly, four constituents out of the identified substances were confirmed to be polyphenol glucuronide conjugates, in which glucuronidation was known to be an important metabolic process in polyphenol aglycone along with methylation and sulphation. This study can be applied for the quality control and standardization of GHL herbal samples and the monitoring of metabolic processes involved in the polyphenolic conjugates. Keywords: Glechoma hederacea; polyphenol glucuronide conjugate; tandem mass spectrometry 1. Introduction Herbal plants used as food ingredients and medical treatments have gained much attention because of their various profitable activities due to antioxidant phytochemicals such as flavonoids and other polyphenolic substances. Among such plants, Glechoma hederacea var. longituba (GHL) has been distributed worldwide from Northeast China [1], to the eastern and western coasts of the United States [2], and widespread throughout Europe and Asia [3]. GHL has been used in folk remedies for centuries to treat gallstones, cholecystitis, jaundice, urinary tract stones [4], and in various treatments for asthma, diabetes, bronchitis, colds and inflammation [5]. More recently, various studies have been published on GHL for antioxidants [6,7], anti-inflammatory agents [6,8], biliary excretion and cholelithiasis [9], antihypertensives [10], hypoglycemia [11], cancer cell suppression [12], and bone necrosis treatment [13]. Recently, as human lifespan and health interests have increased, functional bioactive substances for inhibiting aging and maintaining health have been extensively studied in various aspects [14,15]. As Molecules 2020, 25, 4713; doi:10.3390/molecules25204713 www.mdpi.com/journal/molecules Molecules 2019, 24, x FOR PEER REVIEW 2 of 9 Recently, as human lifespan and health interests have increased, functional bioactive substances Moleculesfor inhibiting2020, 25, aging 4713 and maintaining health have been extensively studied in various aspects [14,15].2 of 9 As a cause of aging in vivo, hydroxyl radicals, singlet oxygen and H2O2, which are derived from reactive oxygen species, have seen increased interest in their removal method [16]. Phenolic acompounds cause of aging widelyin vivo distributed, hydroxyl in radicals, fruit and singlet vegetabl oxygene medicinal and H2O 2plants, which have are derivedbeen recognized from reactive to be oxygenuseful species,substances have showing seen increased antioxidant interest and in theiranticanc removaler effects method [17–20]. [16]. Phenolic Typically, compounds Rosmarinic widely acid distributed(RA) and caffeic in fruit acid and (CA) vegetable prepared medicinal from GHL plants extr haveacts have been been recognized studied to widely be useful to observe substances their showingbeneficial antioxidant effects [17,18]. and anticancer The major eff constituentsects [17–20]. of Typically, GHL have Rosmarinic been reported acid (RA) to andcontain caffeic various acid (CA)polyphenols, prepared fromflavonoids, GHL extracts triterpenoids, have been and studied essential widely oils to observe[19–23]. their Among beneficial them, eff ectshydrophilic [17,18]. Thesubstances major constituents like polyphenols, of GHL flavonoids have been and reported their toderivatives contain various generally polyphenols, show physiochemical flavonoids, triterpenoids,properties that and are essentialeasily extractable oils [19– using23]. Amongaqueous them, media. hydrophilic Because the substances total aqueous like extracts polyphenols, of GHL flavonoidsgenerally andcontain their many derivatives constituents generally and show their physiochemicalcompositional ratios properties can also that affect are easily some extractable profitable usingbiological aqueous effects media. obtainable Because thefrom total the aqueous plant extractsextracts, of a GHL compositional generally contain analysis many of constituentsthe various andconstituents their compositional consisting ratios of the can extracts also aff ectis import some profitableant in not biological only verifying effects obtainable the quality from of thethe plantplant extracts,materials, a compositional but also using analysis the plant of as the food various or medicine. constituents consisting of the extracts is important in not onlyLC-MS verifying provides the quality higher of levels the plant of sensitivity, materials, butthus also making using possible the plant the as foodstructural or medicine. analysis of compoundsLC-MS providesin complex higher matrices levels even of sensitivity, if they are thuspresent making at very possible low concentrations. the structural analysisThis feature of compoundsallows us to in obtain complex a matricescomplete evenoverview if they of are th presente metabolic at very profile low concentrations.of our sample and This provides feature allowsimportant usto mechanistic obtain a complete information overview for what of concerns the metabolic sample profile biochemistry of our sample[24]. In andthis study, provides the importantmass spectrometric mechanistic analysis information of polyphenolic for what concerns ingredients sample from biochemistry GHL hot water [24]. extracts In this study,was conducted. the mass spectrometricThe hot water analysis extracts ofcan polyphenolic be directly useable ingredients as favorable from GHL tea beverages. hot water extractsHigh performance was conducted. liquid Thechromatography hot water extracts coupled can beto high-resolution directly useable and as favorable tandem mass tea beverages. spectrometry High (HPLC-HR performance MS/MSMS) liquid chromatographywill be used for coupledthe efficient to high-resolution identification of and hydrophilic tandem mass polypheno spectrometrylic constituents (HPLC-HR in the MS hot/MSMS) water willextracts be used and for structural the efficient confirmation identification of the of identified hydrophilic major polyphenolic constituents. constituents in the hot water extracts and structural confirmation of the identified major constituents. 2. Results and Discussion 2. Results and Discussion 2.1. Screening and Identification of Polyphenolic Compounds 2.1. Screening and Identification of Polyphenolic Compounds Figure 1 shows the HPLC chromatogram obtained from the analysis of the GHL extracts (GS), Figure1 shows the HPLC chromatogram obtained from the analysis of the GHL extracts (GS), harvested from the Goesan province of South Korea and prepared by hot water extraction. The HPLC harvested from the Goesan province of South Korea and prepared by hot water extraction. The HPLC chromatogram measured at UV 280 nm showed several peaks. High-resolution and tandem mass chromatogram measured at UV 280 nm showed several peaks. High-resolution and tandem mass analysis data of each of the seven identified peaks are summarized in Table 1 and Figure 2. analysis data of each of the seven identified peaks are summarized in Table1 and Figure2. Figure 1. HPLC chromatogram of the hot water extracts of the GHL plant (GS). Figure 1. HPLC chromatogram of the hot water extracts of the GHL plant (GS). MoleculesMolecules 20202019,, 2524,, 4713x FOR PEER REVIEW 33 ofof 99 Table 1. Identification of the molecular formula of the GS extracts by SYNAPT G2, HR-ESI mass Table 1. Identification of the molecular formula of the GS extracts by SYNAPT G2, HR-ESI mass spectrometer in negative ion mode. spectrometer in negative ion mode. RMS Mass Rt Theo. [M − H]− Exp. [M − H]− RMS Mass PeakPeak No. Identified Compound Formula Theo. [M Exp. [M Accuracy Identified Compound Rt (Min)(Min) Formula (m/z) − (m/z−) Accuracy No. H] (m/z) H] (m/z) (ppm) − − (ppm) {[(2E)-3-(3,4- {[(2E)-3-(3,4-Dihydroxyphenyl)-2- 1 Dihydroxyphenyl)-2- 17.37 C12H10O8 281.0292 281.0294 0.238 1 propenoyl]oxy}malonic 17.37 C H O 281.0292 281.0294 0.238 propenoyl]oxy}malonic 12 10 8 acid acid 2 Trans-caffeic acid 22.77 C9H8O4 179.0339 179.0341 0.373 2 Trans-caffeic acid 22.77 C9H8O4 179.0339 179.0341 0.373 Luteolin-7-Luteolin-7-O-di-O-di-
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