Статті в журналах: "Glycosides Analysis"

1

Zheng, Yunfeng, Weiping Duan, Jie Sun, Chenguang Zhao, Qizhen Cheng, Cunyu Li, and Guoping Peng. "Structural Identification and Conversion Analysis of Malonyl Isoflavonoid Glycosides in Astragali Radix by HPLC Coupled with ESI-Q TOF/MS." Molecules 24, no. 21 (October 31, 2019): 3929. http://dx.doi.org/10.3390/molecules24213929.

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In this study, four malonyl isoflavonoid glycosides (MIGs), a type of isoflavonoid with poor structural stability, were efficiently isolated and purified from Astragali Radix by a medium pressure ODS C18 column chromatography. The structures of the four compounds were determined on the basis of NMR and literature analysis. Their major diagnostic fragment ions and fragmentation pathways were proposed in ESI/Q-TOF/MS positive mode. Using a target precursor ions scan, a total of 26 isoflavonoid compounds, including eleven malonyl isoflavonoid glycosides coupled with eight related isoflavonoid glycosides and seven aglycones were characterized from the methanolic extract of Astragali Radix. To clarify the relationship of MIGs and the ratio of transformation in Astragali Radix under different extraction conditions, two MIGs (calycosin-7-O-glycoside-6″-O-malonate and formononetin-7-O-glycoside-6″-O-malonate) coupled with related glycosides (calycosin-7-O-glycoside and formononetin-7-O-glycoside) and aglycones (calycosin and formononetin) were detected by a comprehensive HPLC-UV method. Results showed that MIGs could convert into related glycosides under elevated temperature conditions, which was further confirmed by the conversion experiment of MIGs reference compounds. Moreover, the total contents of MIGs and related glycosides displayed no obvious change during the long-duration extraction. These findings indicated that the quality of Astragali Radix could be evaluated efficiently and accurately by using the total content of MIGs and related glycosides as the quality index.

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2

Caffrey, Andrew, and Susan E. Ebeler. "The Occurrence of Glycosylated Aroma Precursors in Vitis vinifera Fruit and Humulus lupulus Hop Cones and Their Roles in Wine and Beer Volatile Aroma Production." Foods 10, no. 5 (April 24, 2021): 935. http://dx.doi.org/10.3390/foods10050935.

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Volatile aroma compounds found in grapes and hops may be present as both free volatiles and bound glycosides. Glycosides found in the raw materials are transferred to their respective fermented beverages during production where the odorless compounds may act as a reservoir of free volatiles that may be perceived by the consumer if hydrolyzed. A review of the literature on grape and wine glycosides and the emerging literature for glycosides in hops is presented in order to demonstrate the depth of history in grape glycoside research and may help direct new research on hop glycosides. Focus is brought to the presence of glycosides in the raw materials, the effect that winemaking and brewing have on glycoside levels, and current methods for the analysis of glycosidically linked aroma compounds.

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3

Peng, Wenwen, Xiaoxiang Fu, Yuyan Li, Zhonghua Xiong, Xugen Shi, Fang Zhang, Guanghua Huo, and Baotong Li. "Phytochemical Study of Stem and Leaf of Clausena lansium." Molecules 24, no. 17 (August 28, 2019): 3124. http://dx.doi.org/10.3390/molecules24173124.

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Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

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Miyagawa, Yasuyuki, Takahito Mizukami, Hiroshi Kamitakahara та Toshiyuki Takano. "Synthesis and fundamental HSQC NMR data of monolignol β-glycosides, dihydromonolignol β-glycosides and p-hydroxybenzaldehyde derivative β-glycosides for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs)". Holzforschung 68, № 7 (1 жовтня 2014): 747–60. http://dx.doi.org/10.1515/hf-2013-0164.

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Abstract Twelve monolignol (coniferyl alcohol, sinapyl alcohol and p-coumaryl alcohol) β-glycosides (β-glucosides, β-galactosides, β-xylosides and β-mannosides) were synthesised to obtain fundamental NMR data for the analysis of phenyl glycoside type lignin-carbohydrate complexes (LCCs). That is, the 1,2-trans glycosides (the β-glucosides, β-galactosides and β-xylosides) and the 1,2-cis glycosides (the β-mannosides) were synthesized by means of Koenig-Knorr glycosylation and β-selective Mitsunobu glycosylation strategies, respectively. In addition, dihydromonolignol and p-hydroxybenzaldehyde derivative β-glycosides were also prepared from the corresponding monolignol glycosides and their intermediates, respectively. The correlation observed for the C1β-H1β bonds of the sugar moieties in the HSQC spectra of the all β-glycosides varied and were in the range of δC/δH 96–104/4.7–5.4 ppm. Especially, it was found that the correlations derived from the C1β-H1β bonds of the guaiacyl and p-hydroxyphenyl β-mannosides were close to those derived from the C1α-H1α bonds of the 4-O-methyl-α-D-glucuronic acid moieties described in the literature.

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5

Yokosuka, Akihito, and Yoshihiro Mimaki. "Steroidal Glycosides from the Underground Parts of Agapanthus inapertus and Their Cytotoxic Activity." Natural Product Communications 2, no. 1 (January 2007): 1934578X0700200. http://dx.doi.org/10.1177/1934578x0700200107.

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Phytochemical investigation of the underground parts of Agapanthus inapertus (Liliaceae) has resulted in the isolation of three new spirostanol glycosides (1, 3, and 4), along with a known spirostanol glycoside (2) and two known spirostanols (5 and 6). The structures of the new glycosides were determined by spectroscopic analysis and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells.

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6

Agzamova, Manzura Adkhamovna, Ravshanjon Muratjanovich Khalilov та Abdulaziz Adilkhanovich Janibekov. "СHROMATOGRAPHIC ANALYSIS OF СYCLOSIVERSIOSIDE F". chemistry of plant raw material, № 2 (10 червня 2021): 267–74. http://dx.doi.org/10.14258/jcprm.2021028314.

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The plants Astragalus pterocephalus growing in Uzbekistan are a source of triterpene glycosides. The main triterpene glycoside, in terms of content, is a cycloartan glycoside – cyclosiversioside F. To obtain an individual biologically active compound cyclosiversioside F with 95% purity, a proposed method involves extraction with methanol, concentration and dilution with an equal volume of water, then followed by a sequential extraction from the aqueous extract with chloroform, ethyl acetate and butanol. Then a chromatographic separation of the purified amount of extractives on a column with silica gel, isolation of the substance and precipitation from a solvent system must be performed, followed by recrystallization and drying. The optimal conditions for the isolation and separation of the amount of extractive substances have been developed in order to obtain an individual glycoside. Cyclosiversioside F was authenticated by TLC in comparison with an authentic sample. Quantitative analysis of the glycoside was carried out by HPLC. The purity of cyclosiversioside F was confirmed by taking 1H and 13C NMR spectra.

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7

Deng, Xuming, Hu Shang, Jiajia Chen, Jun Wu, Tao Wang, Yiqing Wang, Chensong Zhu, and Weijiang Sun. "Metabolomics Combined with Proteomics Provide a Novel Interpretation of the Changes in Flavonoid Glycosides during White Tea Processing." Foods 11, no. 9 (April 24, 2022): 1226. http://dx.doi.org/10.3390/foods11091226.

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In this study, nonvolatile metabolomics and proteomics were applied to investigate the change mechanism of flavonoid glycoside compounds during withering processing of white tea. With the extension of withering time, the content of the main flavonoid glycoside compounds significantly decreased, and then the flavonoid aglycones and water-soluble saccharides contents increased. However, the change trends of these compounds were inconsistent with the expression pattern of related biosynthesis pathway proteins, indicating that the degradation of flavonoid glycosides might exist in the withering process of white tea. One co-expression network that was highly correlated with variations in the flavonoid glycosides’ component contents during the withering process was identified via WGCNA. Further analysis revealed that the degradation of flavonoid glycosides may be related to the antioxidant action of tea leaves undergoing the withering process. Our results provide a novel characterization of white tea taste formation during processing.

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8

Deng, Xuming, Hu Shang, Jiajia Chen, Jun Wu, Tao Wang, Yiqing Wang, Chensong Zhu, and Weijiang Sun. "Metabolomics Combined with Proteomics Provide a Novel Interpretation of the Changes in Flavonoid Glycosides during White Tea Processing." Foods 11, no. 9 (April 24, 2022): 1226. http://dx.doi.org/10.3390/foods11091226.

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In this study, nonvolatile metabolomics and proteomics were applied to investigate the change mechanism of flavonoid glycoside compounds during withering processing of white tea. With the extension of withering time, the content of the main flavonoid glycoside compounds significantly decreased, and then the flavonoid aglycones and water-soluble saccharides contents increased. However, the change trends of these compounds were inconsistent with the expression pattern of related biosynthesis pathway proteins, indicating that the degradation of flavonoid glycosides might exist in the withering process of white tea. One co-expression network that was highly correlated with variations in the flavonoid glycosides’ component contents during the withering process was identified via WGCNA. Further analysis revealed that the degradation of flavonoid glycosides may be related to the antioxidant action of tea leaves undergoing the withering process. Our results provide a novel characterization of white tea taste formation during processing.

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9

Perrone, Angela, Milena Masullo, Alberto Plaza, Arafa Hamed, and Sonia Piacente. "Flavone and Flavonol Glycosides from Astragalus eremophilus and Astragalus Vogelii." Natural Product Communications 4, no. 1 (January 2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400117.

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Two new rhamnocitrin glycosides (1 and 2) were isolated from the aerial parts of Astragalus vogelii, along with one known rhamnocitrin glycoside (3). Two known flavonol glycosides (4 and 5) and four known flavone derivatives (6-9) were isolated from the aerial parts of Astragalus eremophilus. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis.

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10

Kırmızıbekmez, Hasan, Carla Bassarello, Sonia Piacente, Galip Akaydın, and İhsan Çalış. "Flavonoid, Phenylethanoid and Iridoid Glycosides from Globularia aphyllanthes." Zeitschrift für Naturforschung B 64, no. 2 (February 1, 2009): 252–56. http://dx.doi.org/10.1515/znb-2009-0217.

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A new flavone glycoside, 6-hydroxyluteolin 7-O-[6m-benzoyl-β -D-glucopyranosyl-(1 → 2)]-β - D-glucopyranoside (aphyllanthoside, 1) was isolated from the MeOH extract of the aerial parts of Globularia aphyllanthes. Besides this new compound, two flavonoid glycosides (6-hydroxyluteolin 7-O-[6m-(E)-caffeoyl-β -D-glucopyranosyl-(1 → 2)]-β -D-glucopyranoside and isoquercitrin), three phenylethanoid glycosides (verbascoside, rossicaside A, and trichosanthoside A), and 11 iridoid glycosides (aucubin, catalpol, 10-O-benzoylcatalpol, globularin, asperuloside, besperuloside, asperulosidic acid, daphylloside, scandoside, alpinoside and baldaccioside) were also obtained and characterized. Identification of the isolated compounds was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as HRMS

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11

Kim, Jin-Man, Jong-Ho Koh, and Jung-Min Park. "Validation of an HPLC Method for Pretreatment of Steviol Glycosides in Fermented Milk." Foods 10, no. 10 (October 14, 2021): 2445. http://dx.doi.org/10.3390/foods10102445.

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Steviol glycosides are used in food and beverages worldwide as natural sweeteners, serving as a low-calorie sugar substitute. The acceptable daily intake of steviol is 0–4 mg/kg body weight. The rising demand for dairy products has led to a corresponding increase in the use of steviol glycosides in such products. Therefore, it is important to analyze the levels of steviol glycosides in dairy products. Dairy products have high fat contents and unique emulsion characteristics, conferred by a mixture of fat globules, casein micelles, whey proteins, and numerous other small molecules. These characteristics may interfere with the estimation of steviol glycoside levels; therefore, dairy samples require pretreatment. We aimed to develop an objective test for measuring the levels of steviol glycosides through the development of an efficient pretreatment method. In this study, the steviol glycoside content in dairy products was evaluated by using various methods, and an optimal pretreatment method was determined. We used high-performance liquid chromatography to assess the selectivity, linearity, limit of detection, limit of quantification, accuracy, precision, and recovery rate. Calibration curves were linear in the range of 1–50 mg/kg, with a coefficient of determination of ≥0.999. The limit of detection and limit of quantification were in the ranges of 0.11–0.56 and 0.33–1.69 mg/kg, respectively. The relative standard deviation (%) represents the precision of a measurement. The RSD relative standard deviationof recovery varied between 0.16% and 2.83%, and recovery of the analysis varied between 83.57% and 104.84%. These results demonstrate the reliability of the method for measuring the steviol glycoside content. This method can be used for the simple pretreatment of steviol glycosides and can provide an accurate determination of steviol glycoside content in emulsified food matrices, such as dairy products.

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Wei, Guanhua, Honghong Da, Kaixue Zhang, Junmin Zhang, Jianguo Fang, and Zhigang Yang. "Glycoside Compounds From Glycyrrhiza uralensis and Their Neuroprotective Activities." Natural Product Communications 16, no. 2 (February 2021): 1934578X2199298. http://dx.doi.org/10.1177/1934578x21992988.

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This paper concerns the study of the roots and rhizomes of Glycyrrhiza uralensis where one new alkaloid glycoside, 3,4-dihydroxyquinoline 4- O-β-d-glucopyranoside, along with 13 known compounds (12 phenolic glycosides and one triterpene glycoside) were isolated and identified. The structure of the new compound and the known ones were identified on the basis of nuclear magnetic resonance (NMR) and mass spectrometric (MS) analysis. All the glycosides were tested for their anti-neuroinflammatory activities by inhibiting nitric oxide (NO) release in lipopolysaccharide (LPS)-induced murine microglial BV-2 cells. Several compounds were tested for their antioxidant activities in rat adrenal pheochromocytoma PC12 cells. A structure–activity relationship (SAR) analysis was carried out and revealed that the position and amount of sugar moieties have significant impact on antioxidant activities.

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13

Whaley, Andrey Kennet, Anastasiya Olegovna Ponkratova, Anastasiya Andreyevna Orlova, Evgeni Borisovich Serebryakov, Stanislav Ivanovich Selivanov, Sergey Vladimirovich Krivoshchekov, Mikhail Valer'yevich Belousov, Peter Proksch, and Владимир Геннадьевич Luzhanin. "ANALYSIS OF FLAVONES C-GLYCOSIDES AND AND STEPWISE HYDROLYSIS OF THEIR ACETATES IN THE LEAVES OF RUBUS CHAMAEMORUS L." chemistry of plant raw material, no. 2 (June 10, 2021): 257–65. http://dx.doi.org/10.14258/jcprm.2021029185.

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The C-glycoside embinin and its mono- and diacetate derivatives have immunotropic and cardiotonic activity, which makes the search for plants that contain them interesting. Embinin and its acetate derivatives were previously isolated only from some plants of the genus Iris, the habitat and growing conditions of which are very different from those of the genus Rubus. As a result of the study, the structure of seven C-glycosides, embinin derivatives, isolated from the leaves of Rubus chamaemorus L. (Rosaceae) was established. Using HR-ESI-MS, HPLC-MS, as well as one- and two-dimensional NMR spectroscopy, the structure of three substances isolated in individual form was established: embinin (1) and its diacetyl derivatives – 2''',3'''-diacetylembinin (5) and 3''',4'''-diacetylembinin (7). The method of stepwise hydrolysis of C-glycoside acetate residues proposed in this study, followed by HPLC analysis of the resulting hydrolysis products, made it possible to establish the structure of minor flavone C-glycosides contained in the leaves of Rubus chamaemorus L.: 2'''-acetylembinin (2), 3'''-acetylembinin (3), 4'''-acetylembinin (4) and 2''',4'''-diacetylembinin (6). All these compounds were found in the leaves of Rubus chamaemorus L. for the first time. The C-glycosides - embinin and its acetate derivatives are rare metabolites of higher plants, the presence of which is determined by the peculiarity of their physiology, and the biological activity determines the prospects for medical use.

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14

Morris, Sandra A., Peter T. Northcote, and Raymond J. Andersen. "Triterpenoid glycosides from the Northeastern Pacific marine sponge Xestospongia vanilla." Canadian Journal of Chemistry 69, no. 9 (September 1, 1991): 1352–64. http://dx.doi.org/10.1139/v91-201.

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Isoxestovanin A (6), xestovanin B (7), xestovanin C (8), dehydroxestovanin A (9), epidehydroxestovanin A (10), dehydroxestovanin C (11), and secodehydroxestovanin A (12), seven new triterpenoid glycosides, have been isolated from the Northeastern Pacific sponge Xestospongia vanilla. The structures of the metabolites were determined by a combination of spectroscopic analysis and chemical degradation. The aglycone of 6 has the new isoxestovanane triterpenoid carbon skeleton. Compounds 7, 8, and 11 are the first X. vanilla triterpenoid glycosides known to contain three monosaccharide subunits. Key words: triterpenoid, glycoside, sponge, Xestospongia.

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15

Royik, M., I. Kuznetsova, V. Holodniak, and V. Mazayeva. "Determining the quality of diterpene glycosides, obtained from stevia leaves." Agricultural Science and Practice 3, no. 2 (July 15, 2016): 19–25. http://dx.doi.org/10.15407/agrisp3.02.019.

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Aim. To determine the quality of diterpene glycoside powders, produced in Ukraine using the stevia leaves of plants of domestic and foreign origin. Methods. Differential scanning calorimetry and thermographic analy- sis. Results. It was demonstrated that the increase in the production of powders of diterpene glycosides in the world results in stepping up the requirements to the selection material of stevia and the quality of powders, obtained from its leaves as a fi nal product. The quality of diterpene glycoside powders, produced in Ukraine us- ing the stevia leaves of plants of domestic and foreign origin, was investigated. Conclusions. It was determined that special attention in the analysis of the powder samples of diterpene glycosides should be paid to the sample preparation: increased humidity of the sample promotes a weakening of carbohydrate bonds and rapid decline in their quality. Differential scanning calorimetry allows determining the content of additives, the degree of moisture saturation, and may further be used in the screening of selection samples and forecasting the shelf life of powders of diterpene glycosides.

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Watanabe, Kazuki, Yoshihiro Mimaki, Haruhiko Fukaya, and Yukiko Matsuo. "Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica." Molecules 24, no. 1 (December 25, 2018): 69. http://dx.doi.org/10.3390/molecules24010069.

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Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

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Jin, Jing, Yi-Qing Lv, Wei-Zhong He, Da Li, Ying Ye, Zai-Fa Shu, Jing-Na Shao, et al. "Screening the Key Region of Sunlight Regulating the Flavonoid Profiles of Young Shoots in Tea Plants (Camellia sinensis L.) Based on a Field Experiment." Molecules 26, no. 23 (November 26, 2021): 7158. http://dx.doi.org/10.3390/molecules26237158.

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Both UV and blue light have been reported to regulate the biosynthesis of flavonoids in tea plants; however, the respective contributions of the corresponding regions of sunlight are unclear. Additionally, different tea cultivars may respond differently to altered light conditions. We investigated the responses of different cultivars (‘Longjing 43’, ‘Zhongming 192’, ‘Wanghai 1’, ‘Jingning 1’ and ‘Zhonghuang 2’) to the shade treatments (black and colored nets) regarding the biosynthesis of flavonoids. For all cultivars, flavonol glycosides showed higher sensitivity to light conditions compared with catechins. The levels of total flavonol glycosides in the young shoots of different tea cultivars decreased with the shade percentages of polyethylene nets increasing from 70% to 95%. Myricetin glycosides and quercetin glycosides were more sensitive to light conditions than kaempferol glycosides. The principal component analysis (PCA) result indicated that shade treatment greatly impacted the profiles of flavonoids in different tea samples based on the cultivar characteristics. UV is the crucial region of sunlight enhancing flavonol glycoside biosynthesis in tea shoots, which is also slight impacted by light quality according to the results of the weighted correlation network analysis (WGCNA). This study clarified the contributions of different wavelength regions of sunlight in a field experiment, providing a potential direction for slightly bitter and astringent tea cultivar breeding and instructive guidance for practical field production of premium teas based on light regimes.

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Hong, Yan, Zhihong Gui, Xiaoping Cai, and Lejian lan. "Clinical efficacy and safety of tripterygium glycosides in treatment of stage IV diabetic nephropathy: A meta-analysis." Open Medicine 11, no. 1 (January 1, 2016): 611–17. http://dx.doi.org/10.1515/med-2016-0099.

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AbstractThe aim of this meta-analysis was to evaluate the clinical efficacy and safety of tripterygium glycosides in treatment of stage IV diabetic nephropathy. Methods Through searching the PubMed and CNKI databases, the open published clinically controlled trials related to efficacy and safety of tripterygium glycosides in the treatment of stage IV diabetic nephropathy were collected. The pooled total efficacy, 24h urinary protein, serum creatinine and tripterygium glycosides related toxicity were calculated using Stata 11.0 software. Results Fourteen publications including 992 subjects (512 in the experimental group and 480 in the control group) were included in this study. Eight studies reported the total clinical efficacy comparing the experiment and control groups. No significant statistical heterogeneity was found in total efficacy (I2=24.9%, p>0.05). Thus, the combined odds ratio (OR) was pooled by fixed effect model. The pooled OR=4.16 with its 95% CI 2.71~6.37 (p<0.05), which indicated the total efficacy in the experiment group, was significant higher than that of control group (p<0.05); Thirteen studies reported the post-treatment 24h urinary protein value. Statistical heterogeneity analysis indicated significant heterogeneity across studies (I2=91.1%, p<0.05); that data was pooled by a random effects model. The combined standardized mean difference (SMD) was -1.55 with its 95% I -2.06~1.03, (p<0.05). The results indicated that post-treatment 24h urinary protein in the experiment group was significant lower than that in control group (p<0.05); Ten studies reported the post-treatment serum creatinine. Significant heterogeneity existed across those studies (I2=82.3%, p<0.05). Thereafter, the data was pooled by a random effect model. The combined standardized mean difference (SMD) was −0.24 with its 95%CI −0.40~0.09, (p<0.05). The results indicated that the post-treatment serum creatinine in experiment group was significant lower than that of control group (p<0.05); Eight studies reported tripterygium glycoside-associated toxicity such as liver function damage, gastrointestinal reactions and menstrual disorders. With no statistical heterogeneity among the studies, the data was pooled by fixed effect model. The pooled OR=6.42 (95%CI 2.23~18.48, p<0.05). The pooled results showed the tripterygium glycoside- associated toxicity incidence rate was significant higher in the experiment group than that of the control group (p<0.05); There were no publication bias for effect size of total efficacy, 24h urinary protein, and serum creatinine. However, for tripterygium glycoside-related toxicity, the publication bias was significant (t=-3.55, p<0.05). Conclusion The present evidence shows that tripterygium glycosides can improve clinical efficacy, reduce the 24h urinary protein and serum creatinine, but that they increase the tripterygium glycoside-related toxicity in treatment of stage IV diabetic nephropathy.

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19

Brandle, Jim. "Genetic control of rebaudioside A and C concentration in leaves of the sweet herb, Stevia rebaudiana." Canadian Journal of Plant Science 79, no. 1 (January 1, 1999): 85–91. http://dx.doi.org/10.4141/p98-048.

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Stevia rebaudiana Bertoni produces steviol glycoside sweeteners in its leaves that are up to 240 times sweeter than sugar. Understanding the genetic basis of glycoside proportions will aid in their manipulation through plant breeding. The experiments conducted in this study were focused on the genetic control of the proportions of two of those glycosides, rebaudioside A and rebaudioside C. The study was conducted using F2 population from crosses between two sets of parents with divergent glycoside profiles. Segregation in the first set of F2s showed that the presence/absence of rebaudioside A is controlled by a single dominant gene, but that the actual proportions of rebaudioside A may be controlled by multiple loci or alleles. In a second cross, proportions of rebaudioside A and rebaudioside C were found to co-segregate and were shown to be controlled by a single additive gene. This result suggests that both rebaudioside A and C are synthesized by the same enzyme. The results were used to propose a model for glycosylation of steviol glycosides. Key words: Diterpene glycoside, genetic analysis, glycosylation, biosynthetic model

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20

Bejarano, Natividad, Leticia Lafuente, Juliana Esteche, Cintia C. Santiago, Agustín H. Rojas, and Agustín Ponzinibbio. "Synthesis and Structure of Novel Potentially Bioactive Amphiphilic -O-(N)-Glycosides." Chemistry Proceedings 3, no. 1 (November 14, 2020): 100. http://dx.doi.org/10.3390/ecsoc-24-08286.

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Herein we present the synthesis and structural analysis of novel -O-(N)-glycosides. The biphasic reaction of NHS and acetobromo-α-d-glucose or d-galactose gives the β anomer glycoside in a straightforward manner. Further hydrazinolysis and condensation with decanal afforded the desired products. Their complete structures, including the anomeric and E/Z double bond configurations, were determined by spectroscopic analysis.

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Burda, Nadiia, Iryna Zhuravel, Moeen F. Dababneh, Andrii Kotov, Elina Kotova, and Andrii Popyk. "Identification and quantitative analysis of furostanol glycosides in caltrop." Pharmacia 67, no. 4 (October 2, 2020): 187–91. http://dx.doi.org/10.3897/pharmacia.67.e37433.

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This study describes the identification and quantitative determination of furostanol glycosides in caltrop herb harvested in the fructification period. Furostanol glycosides were identified by thin-layer chromatography (TLC) and quantified by UV-vis spectrophotometry. The furostanol glycosides were visualized on the TLC plate as pink spots after treatment with dimethylamine benzaldehyde solution. UV-vis spectrophotometry quantified these substances to the amount of at least 0.4 %. The data on the identification and quantification of furostanol glycosides obtained in the course of this research was implemented in the development of the Ukrainian State Pharmacopoeia for caltrop herb.

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de GRAAF, Michelle, Irene C. van VEEN, Ida H. van der MEULEN-MUILEMAN, Winald R. GERRITSEN, Herbert M. PINEDO та Hidde J. HAISMA. "Cloning and characterization of human liver cytosolic β-glycosidase". Biochemical Journal 356, № 3 (8 червня 2001): 907–10. http://dx.doi.org/10.1042/bj3560907.

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Cytosolic β-glucosidase (EC 3.2.1.21) from mammalian liver is a member of the family 1 glycoside hydrolases and is known for its ability to hydrolyse a range of β-d-glycosides, including β-d-glucoside and β-d-galactoside. We therefore refer to this enzyme as cytosolic β-glycosidase. We cloned the cDNA encoding the human cytosolic β-glycosidase by performing PCR on cDNA prepared from total human liver RNA. Specific primers were based on human expressed sequence tags found in the expressed sequence tag database. The cloned cDNA contained 1407nt with an open reading frame encoding 469 amino acid residues. Amino acid sequence analysis indicates that human cytosolic β-glycosidase is most closely related to lactase phlorizin hydrolase and klotho protein. The enzyme was characterized by using cell lysates of COS-7 cells transfected with a eukaryotic expression vector containing the cDNA. The biochemical, kinetic and inhibition properties of the cloned enzyme were found to be identical with those reported for the enzyme purified from human liver.

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23

Zhang, Feng-Mei, Min-Jie Zheng, Yan-Qun Xu, Chun-Ping Xu, Zhi-Hua Liu, Zhen-Jie Li, and Zhi-Gang Tai. "Temperature-Responsive Glycosides for Controlled Release of Decanol Towards Sustainable Disinfect Effect." Journal of Biobased Materials and Bioenergy 16, no. 4 (August 1, 2022): 603–10. http://dx.doi.org/10.1166/jbmb.2022.2215.

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Controlling the release of decanol with temperature is a reliable way to improve the utilization of decanol. In this paper, a temperature-controlling release decyl glycoside was synthesized using method of Koenigs-Knorr acetyl glycoside synthesis. Thereafter, the resultant decyl glycoside was characterized in terms of thermogravimetric analysis, differential scanning calorimetry and pyrolysis analysis, respectively. Moreover, both the temperature-responsive responsive in vitro release and disinfection activities were also assessed. Finally, the results showed that the yield of decyl glycoside was 81%, which was higher than that conventional formulation. The decyl glycoside possessed outstanding performance of thermostabilization and controlled release properties with temperature. The release of decanol from decyl glycoside could be well described by mechanism of the case II transport and fickian diffusion. Disinfect effect studies have shown a positive correlation between long-term disinfection decyl glycosides and temperature-induced changes in release rate. Based on these results, decyl glycoside could improve stability and long-term disinfection of decanol by controlling temperature, which could be bound to drug, food, and other industry.

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24

Segurel, Marie A., Raymond L. Baumes, Christine Riou, and Alain Razungles. "Role of Glycosidic Aroma Precursors on the odorant profiles of Grenache noir and Syrah Wines from the Rhone valley. Part 1: sensory study." OENO One 43, no. 4 (December 31, 2009): 199. http://dx.doi.org/10.20870/oeno-one.2009.43.4.793.

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Aims: The aim of this study was to demonstrate the impact of the volatile compounds, arising from glycosidic precursors contained in the berries of Vitis vinifera L.cv Syrah and Grenache noir varieties, on wine aromas from these varieties.Methods and results: The sensory analysis was used to compare Grenache noir and Syrah wines. The role played by the glycosidic precursors on the future odorant profile of the wines from both varieties was demonstrated in an experiment by increasing their natural content in glycosides. Then, odorant compounds were generated by aging treatments, heating at 45 °C for 3 weeks, preceded or not by enzyme addition, or natural aging for 18 months. The wines were then submitted to a selected and trained panel. Samples were compared using triangular test. Furthermore, a quantitative descriptive analysis was carried out to determine the aroma attributes describing and discriminating the wines from the two varieties.Conclusion: The glycoconjugates increased the global aromatic complexity, and enhanced the fruity aromas in Grenache wines and the leather or olive aromas in Syrah wines. The use of glycosidase enzymes led to a stewed fruit character in Grenache wines, whereas in Syrah wines, the samples enriched with glycosides differed according to the « terroir ».Significance and impact of study: This study showed the impact of the glycosidic fraction of the grapes on the varietal aroma of wines. Furthermore, comparisons of the results obtained by both aging techniques highlight the experimental interest of the aging model but also its limits.

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Li, Chunbao, Wenjiao Yuan та Yali Liu. "A Rapid and Diastereoselective Synthesis of 2-Deoxy-2-iodo-α-glycosides and its Mechanism for Diastereoselectivity". Synlett 28, № 15 (24 травня 2017): 1975–78. http://dx.doi.org/10.1055/s-0036-1588440.

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Reductive deiodination of 2-deoxy-2-iodo-glycoside is an efficient and practical approach for the synthesis of 2-deoxyglycosides, which are moieties of bioactive compounds. However, inseparable diastereoisomers are usually formed in the preparation of 2-deoxy-2-iodo-glycosides via glycosylation of glycals with alcohols using current methods. To overcome this problem, a rapid and diastereoselective transformation of glycals and alcohols into 2-deoxy-2-iodo-α-glycosides enabled by I2/PhI(OAc)2 has been developed. 14 glycals, derived from 13 monosaccharides and one disaccharide, diastereoselectively yielded α-glycosides. Only in two cases the diastereoselectivity of the glycosylation was poor. The yields of glycosylation range from 73% to 95%, and the reactions are finished in only five minutes. Investigations for better diastereoselectivity by comparing I2/Ph(OAc)2- with I2/Cu(OAc)2-mediated glycosylations using UV analysis have been conducted.

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Ma, Zhong-Lian, Zhi-Pu Yu, Yao-Yao Zheng, Na Han, Ya-Hui Zhang, Shu-Yue Song, Jun-Qiu Mao, Jiao-Jiao Li, Guang-Shan Yao, and Chang-Yun Wang. "Bioactive Alpha-Pyrone and Phenolic Glucosides from the Marine-Derived Metarhizium sp. P2100." Journal of Fungi 9, no. 1 (December 23, 2022): 28. http://dx.doi.org/10.3390/jof9010028.

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Glycoside compounds have attracted great interest due to their remarkable and multifarious bioactivities. In this study, four hitherto unknown 4-methoxy-β-D-glucosyl derivatives were obtained and identified from the marine-derived fungus Metarhizium sp. P2100, including three alpha-pyrone glycosides (1–3) and one phenolic glycoside (4). Their planar structures were elucidated by comprehensive spectroscopic analysis, including 1D/2D NMR and HRESIMS. The absolute configurations of 1–3 were determined by a single-crystal X-ray crystallographic experiment, a comparison of the experimental, and a calculated electronic circular dichroism (ECD) spectra, respectively. Compounds 2 and 3 are a pair of rare epimeric pyranoside glycosides at C-7 with a core of aglycone as 2H-pyrone. Compounds 1–4 exhibited weak anti-inflammatory activities. In particular, compounds 1–3 displayed inhibitory activities against α-amylase, showing a potential for the development of a new α-amylase inhibitor for controlling diabetes.

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Takahashi, Naoki, Tomoki Iguchi, Minpei Kuroda, Masaki Mishima, and Yoshihiro Mimaki. "Novel Oleanane-Type Triterpene Glycosides from the Saponaria officinalis L. Seeds and Apoptosis-Inducing Activity via Mitochondria." International Journal of Molecular Sciences 23, no. 4 (February 12, 2022): 2047. http://dx.doi.org/10.3390/ijms23042047.

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Saponaria officinalis L., commonly known as “Soapwort”, is a rich source of triterpene glycosides; however, the chemical constituents of S. officinalis seeds have not been fully identified. In this study, we conducted a systematic phytochemical investigation of the seeds of S. officinalis and obtained 17 oleanane-type triterpene glycosides (1–17), including seven new glycosides (1–7). The structures of 1–7 were determined based on a detailed analysis of NMR spectroscopic data and chromatographic and spectroscopic analyses following specific chemical transformation. The cytotoxicities of the isolated compounds were evaluated against HL-60 human promyelocytic leukemia cells, A549 human adenocarcinoma lung cancer cells, and SBC-3 human small-cell lung cancer cells. The cytotoxicities of 1, 4, and 10 toward HL-60 cells and SBC-3 cells were nearly as potent as that of cisplatin. Compound 1, a bisdesmosidic triterpene glycoside obtained in good yield, arrested the cell cycle of SBC-3 cells at the G2/M phase, and induced apoptosis through an intrinsic pathway, accompanied by ROS generation. As a result of the mitochondrial dysfunction induced by 1, mitochondria selective autophagy, termed mitophagy, occurred in SBC-3 cells.

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Sarma, Sai Koteswar, D. Umamaheswari, B. S. Venkateswaralu, and M. Kumar. "PRELIMINARY PHYTOCHEMICAL ANALYSIS OF ANTIFERTILITY PLANTS." YMER Digital 21, no. 07 (July 29, 2022): 1218–24. http://dx.doi.org/10.37896/ymer21.07/a1.

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The objective of this study was to investigate the presence of various phytochemicals obtained from ethanol (E), ethyl acetate (ET), methanol (M), and chloroform (C) extracts of the Datura Stramonium and Musa Paradasica. Methods: The freshly collected plant materials were subjected to successive extraction separately using E,ET, M and C with soxhlet apparatus. Using the standard protocols, the leaf extracts obtained were subjected to preliminary phytochemical analysis to detect the presence of carbohydrates, proteins, steroids, flavonoids, tannins, and alkaloids. Results: The phytochemical analysis showed the presence of tannins, flavonoids, alkaloids, terpenoids, glycosides, saponins, resins, carbohydrates and proteins. The Datura Stramonium and Musa Paradasica plants showed the presence of flavonoids, terpenoids, glycosides, carbohydrates and proteins. Flavonoids, alkaloids, terpenoids, glycosides, resins, carbohydrates and proteins are found in the leaves of Datura Stramonium. Flavonoids, glycosides and resins were found in the leaves of Musa Paradasica. Ethanol and methanol leaf extracts from Datura Stramonium and Musa Paradasica indicated that they contained most of thephytochemicalcompounds. Conclusion: The different extracts of plants have clearly indicated the presence of all the major phytochemicals; hence, these plants can be used for the extraction of bioactive compounds. Keywords: Phytochemicals,Datura Stramonium and Musa Paradasica

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Mauri, Pierluigi, Giovanna Catalano, Claudio Gardana, and Piergiorgio Pietta. "Analysis ofStevia glycosides by capillary electrophoresis." Electrophoresis 17, no. 2 (1996): 367–71. http://dx.doi.org/10.1002/elps.1150170213.

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Onlom, Churanya, Nitra Nuengchamnong, Watoo Phrompittayarat, Waraporn Putalun, Neti Waranuch, and Kornkanok Ingkaninan. "Quantification of Saponins in Asparagus racemosus by HPLC-Q-TOF-MS/MS." Natural Product Communications 12, no. 1 (January 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200103.

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Asparagus racemosus Willd. or Shatavari (Asparagaceae family) is an important medicinal plant in Ayurvedic medicine as a rejuvenate for women. A method for quantitative analysis of saponin glycosides bioactive constituents in A. racemosus is reported. A high performance liquid chromatography quadrupole time of flight mass spectrometry (HPLC-Q-TOF-MS/MS) method was developed and validated for simultaneous determination of five saponin glycosides, asparacoside, shatavarin IX, shatavarin IV, asparanin A and shatavarin V in A. racemosus extracted with 70% MeOH. The method was validated through intra-and inter-day precision, with the relative standard deviation (RSD) less than 6%, limits of detection (LOD) and limits of quantification (LOQ) <10 and 50 ng, respectively. Overall recoveries ranged from 95% to 105%, with RSD ranging from 0.7% to 4.5%. The method was applied to saponin glycoside contents in the leaves, stems, and roots of A. racemosus sourced from different geographical locations, including four provinces in Thailand, and a sample from India. Saponin glycosides were detected predominantly in the roots, the part used in traditional medicines and these showed wide variations in saponin glycoside profiles from undetectable to 12 mg/g dry weight. The quality control of A. racemosus is crucial for reliable and predictable therapies and only methods like the one developed has the necessary flexibility, sensitivity, accuracy, and selectivity for reliable routine quality control.

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Yin, Qiang, Rahima Abdulla, Gulmira Kahar, Haji Akber Aisa, Chunting Li, and Xuelei Xin. "Mass Defect Filtering-Oriented Identification of Resin Glycosides from Root of Convolvulus scammonia Based on Quadrupole-Orbitrap Mass Spectrometer." Molecules 27, no. 11 (June 6, 2022): 3638. http://dx.doi.org/10.3390/molecules27113638.

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This work aimed to develop and evaluate a post-acquisition data processing strategy, referred to as a mass defect filter (MDF), for rapid target the resin glycosides in root of Convolvulus scammonia by setting mass rang and mass defect range from high-resolution MS data. The full-scan mass data were acquired by high-performance liquid chromatography coupled with Q Exactive Plus hybrid quadrupole-orbitrap mass spectrometer that featured high resolution, mass accuracy, and sensitivity. To screen resin glycosides, three parent filter m/z 871, m/z 853, and m/z 869 combined with diagnostic fragment ions (DFIs) approach were applied to remove the interference from complex herbal extract. The targeted components were characterized based on detailed fragment ions. Using this approach, 80 targeted components, including 22 glycosidic acids and 58 resin glycosides were tentatively identified. The present results suggested that the proposed MDF strategy would be adaptable to the analysis of complex system in relevant filed.

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Ren, Chaoxiang, Chao Chen, Shuai Dong, Rui Wang, Bin Xian, Tianlei Liu, Ziqing Xi, Jin Pei, and Jiang Chen. "Integrated metabolomics and transcriptome analysis on flavonoid biosynthesis in flowers of safflower (Carthamus tinctorius L.) during colour-transition." PeerJ 10 (June 22, 2022): e13591. http://dx.doi.org/10.7717/peerj.13591.

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Background Safflower (Carthamus tinctorius L.), well known for its flower, is widely used as a dye and traditional Chinese medicine. Flavonoids, especially flavonoid glycosides, are the main pigments and active components. However, their biosynthesis is largely unknown. Interestingly, the colour of flowers in safflower changed from yellow to red during flower development, while much of the gene and chemical bases during colour transition are unclear. Methods In this research, widely targeted metabolomics and transcriptomics were used to elucidate the changes in flavonoid biosynthesis from the gene and chemical points of view in flowers of safflower during colour transition. The screening of differential metabolites depended on fold change and variable importance in project (VIP) value. Differential expressed genes (DEGs) were screened by DESeq2 method. RT-PCR was used to analyse relative expressions of DEGs. Results A total of 212 flavonoid metabolites, including hydroxysafflor yellow A, carthamin and anthocyanins, were detected and showed a large difference. The candidate genes of glycosyltransferases and flavonoid hydroxylase that might participate in flavonoid glycoside biosynthesis were screened. Ten candidate genes were screened. Through integrated metabolomics and transcriptome analysis, a uridine diphosphate glucose glycosyltransferase gene, CtUGT9 showed a significant correlation with flavonoid glycosides in safflower. In addition, expression analysis showed that CtUGT9 was mainly expressed in the middle development of flowers and was significantly upregulated under MeJA treatment. Our results indicated that CtUGT9 might play an important role in flavonoid glycoside biosynthesis during colour-transition in safflower.

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Ouyang, Dan, Lan-Chun Wang, Ting Tang, and Hong Feng. "Genomic-Wide Identification and Characterization of the Uridine Diphosphate Glycosyltransferase Family in Eucommia ulmoides Oliver." Plants 10, no. 9 (September 17, 2021): 1934. http://dx.doi.org/10.3390/plants10091934.

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Eucommia ulmoides Oliver is a woody plant with great economic and medicinal value. Its dried bark has a long history of use as a traditional medicinal material in East Asia, which led to many glycosides, such as aucubin, geniposide, hyperoside, astragalin, and pinoresinol diglucoside, being recognized as pharmacologically active ingredients. Uridine diphosphate glycosyltransferases (UGTs) catalyze a glycosyl-transferring reaction from the donor molecule uridine-5′-diphosphate-glucose (UDPG) to the substrate, which plays an important role in many biological processes, such as plant growth and development, secondary metabolism, and environmental adaptation. In order to explore the biosynthetic pathways of glycosides in E. ulmoides, 91 putative EuUGT genes were identified throughout the complete genome of E. ulmoides through function annotation and an UDPGT domain search. Phylogenetic analysis categorized them into 14 groups. We also performed GO annotations on all the EuUGTs to gain insights into their functions in E. ulmoides. In addition, transcriptomic analysis indicated that most EuUGTs showed different expression patterns across diverse organs and various growing seasons. By protein–protein interaction predication, a biosynthetic routine of flavonoids and their glycosides was also proposed. Undoubtedly, these results will help in future research into the biosynthetic pathways of glycoside compounds in E. ulmoides.

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Dong, Yongzhe, Jingya Ruan, Zhijuan Ding, Wei Zhao, Mimi Hao, Ying Zhang, Hongyu Jiang, Yi Zhang, and Tao Wang. "Phytochemistry and Comprehensive Chemical Profiling Study of Flavonoids and Phenolic Acids in the Aerial Parts of Allium Mongolicum Regel and Their Intestinal Motility Evaluation." Molecules 25, no. 3 (January 29, 2020): 577. http://dx.doi.org/10.3390/molecules25030577.

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To clarify whether flavonoids and phenols in Allium mongolicum Regel have the effect of improving gastrointestinal function and analyze its quality, this study was designed to isolate and identify them from the aerial parts of A. mongolicum by using various chromatographic and spectrophotometric methods, a bioassay on motility of mouse isolated intestine tissue, as well as qualitative analysis using liquid chromatography/mass spectrometry (LC-MS) analysis. As a result, 31 flavonoids and phenolic acids were obtained and identified, including six new flavonoid glycosides, mongoflavonosides A1 (1), A2 (2), A3 (3), A4 (4), B1 (5), B2 (6), and four new phenolic acid glycosides, mongophenosides A1 (7), A2 (8), A3 (9), B (10). Among them, eleven flavonoids and three phenolic acids showed significant increase in the height of mouse small intestinal muscle. It was a first systematic bioactive constituents’ study for A. mongolicum on gastrointestinal tract. Furthermore, according to the retention time (tR) and the exact mass-to-charge ratio (m/z), thirty-one compounds were unambiguously identified by comparing to the standard references by using LC-MS. Then, on the basis of generalized rules of MS/MS fragmentation pattern, chromatographic behaviors, as well as biosynthetic laws of the 31 isolates, five flavonoid glycosides and one phenolic acid glycoside were tentatively speculated. On the basis of the study, a fast analysis method for flavonoids and phenolic acids in A. mongolicum was established.

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Marchenko, Alexandra, Pavel Kintia, Natalia Mashcenco, Carla Bassarello, Sonia Piacente, and Cosimo Pizza. "Phenylethanoid and Iridoid Glycosides from Veronica Chamaedrys L." Chemistry Journal of Moldova 3, no. 2 (December 2008): 101–4. http://dx.doi.org/10.19261/cjm.2008.03(2).08.

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Three phenylethanoid glycosides (1, 2, 3) and one iridoid glycoside (4) were isolated from aerial parts of Veronica chamaedrys L. (Scrophulariaceae) for the first time. On the basis of spectral analysis, the structures of these compounds were determined to be acteoside (3,4-dihydroxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside) (1), ehrenoside (3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-β-D-glucopyranoside) (2), chamaedroside (3,4-dihydroxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-α-L-arabinopyranoside) (3) and aucuboside (4).

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Park, Kyoung Jin, Won Se Suh, Da Hye Yoon, Chung Sub Kim, Sun Yeou Kim, and Kang Ro Lee. "Phenolic constituents from twigs of Aleurites fordii and their biological activities." Beilstein Journal of Organic Chemistry 17 (September 7, 2021): 2329–39. http://dx.doi.org/10.3762/bjoc.17.151.

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Three new neolignan glycosides (1–3), a new phenolic glycoside (15), and a new cyanoglycoside (16) were isolated and characterized from the twigs of Aleurites fordii together with 14 known analogues (4–14 and 17–19). The structural elucidation of the new compounds was performed through the analysis of their NMR, HRMS, and ECD spectra and by chemical methods. All isolated compounds were tested for their antineuroinflammatory and neuroprotective activities.

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Parris, Cheryl A., Clinton C. Shock, and Michael Qian. "Soil Water Tension Irrigation Criteria Affects Stevia rebaudiana Leaf Yield and Leaf Steviol Glycoside Composition." HortScience 52, no. 1 (January 2017): 154–61. http://dx.doi.org/10.21273/hortsci11352-16.

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Stevia (Stevia rebaudiana Bertoni) is of interest for the production of steviol glycosides due to their noncaloric sweetening properties. Commercial stevia leaf production to date has focused on rebaudioside A and stevioside. Relatively little is known about the cultural practices necessary for the efficient production of stevia leaf and steviol glycosides. Irrigation management is an important agronomic technique that growers can use to obtain high yield while also pursuing water use efficiency (WUE). This trial investigated the effect that irrigation onset criteria measured as soil water tension (SWT) had on dry stevia leaf yields, steviol glycoside content and yield, and steviol glycoside ratios. Two stevia cultivars, SW 107 and SW 129 (S&W Seed Company Inc., Fresno, CA), were subjected to SWT irrigation criteria of 10, 20, 40, 60, and 80 kPa over a 57-day trial period at the Oregon State University (OSU) Malheur Experiment Station, Ontario, OR. Harvested plant material was evaluated for dry leaf yield and content of several steviol glycosides. Analysis of variance (ANOVA) showed significant cultivar differences in leaf yield, leaf stevioside and rebaudioside A content and yield, and steviol glycoside ratios (P = 0.05). Examining the data by ANOVA, dry leaf yield, stevioside percent, rebaudioside C percent, total steviol glycoside (TSG) percent, rebaudioside C yield, and TSG yield were significantly greater among the wetter (closer to 10 kPa) compared with the drier (closer to 80 kPa) SWT criteria treatments, yet a preferred treatment regime was not clearly evident. When comparing cultivars by regression analysis, there was a highly significant decrease in the stevioside content, and an increase in the ratio of rebaudioside A to stevioside from wetter to drier irrigation onset criteria (due to lower stevioside), whereas the rebaudioside A content did not respond significantly to differing irrigation criteria. Increasing dry leaf productivity with wetter irrigation criteria (closer to 10 kPa), directly increased the total rebaudioside A yield also, which in turn could provide increased crop value to the grower. Irrigating near 10 kPa produced higher dry leaf yield and total rebaudioside A yield, than irrigating at drier criteria.

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Karapandzova, Marija, Gjose Stefkov, Ivana Cvetkovikj, Jasmina Petreska Stanoeva, Marina Stefova, and Svetlana Kulevanova. "Flavonoids and Other Phenolic Compounds in Needles of Pinus peuce and Other Pine Species from the Macedonian Flora." Natural Product Communications 10, no. 6 (June 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000647.

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Flavonoids and other phenolic compounds in young needles of four pine species, Pinus peuce, P. nigra, P. mugo and P. sylvestris from the Macedonian flora were investigated. The amount of total phenols and total flavonoids were determined using Folin-Ciocalteau and aluminum chloride assay, respectively. The obtained results revealed that the total phenolic content (TPC) and total flavonoids content (TFC) varied among different pine species ranging from 9.8 to 14.0 mg GAE/g and from 3.3 to 7.2 mg CE/g of dried plant material, respectively. Qualitative analysis of flavonoids and other phenolic components was made by a LC-DAD/ESI-MSn optimized chromatographic method. A total of 17 phenolic components were identified and classified as: acids (2), procyanidins (2) and flavonoid glycosides (13). The most prevalent components were flavonoid glycosides, especially flavonols and methylated flavonols (9). Additionally, 3 components were found as acylated flavonol glycosides with ferulic and p-coumaric acid. The last one was found not only in esterified form but also in the free form. Only one flavone-apigenin glycoside was detected. Procyanidins were identified as catechin derivatives, both dimers and trimers.

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Liang, Qingrong, He Qian, and Weirong Yao. "Identification of Flavonoids and Their Glycosides by High-Performance Liquid Chromatography with Electrospray Ionization Mass Spectrometry and with Diode Array Ultraviolet Detection." European Journal of Mass Spectrometry 11, no. 1 (February 2005): 93–101. http://dx.doi.org/10.1255/ejms.710.

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Identification of flavonoids and flavonoid glycosides was carried out on Psidium guajava Linn leaves by means of high-performance liquid chromatography ultraviolet (HPLC-UV) analysis and HPLC mass spectrometry. By using HPLC-UV, two known phenolics (gallic acid and quercetin) and five newly reported ones (procatechuic acid, chlorogenic acid, caffeic acid, kaempferol and ferulic acid) were identified in alcohol guava leaf extract. Structural information about the compounds was obtained from the retention times, the UV spectra and mass spectra without the need to isolate the individual compounds. Two flavonoids (quercetin and kaempferol) and four flavonoid glycosides (three known components, quercetin 3-O-alpha-L-arabinoside, quercetin 3-O-beta-D-glucoside and quercetin 3-O-beta-D-galactoside, along with one novel compound, kaempferol-glycoside) and three other unknown compounds have been identified in the fractions.

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Murkovic, M., U. Adam, and W. Pfannhauser. "Analysis of anthocyane glycosides in human serum." Fresenius' Journal of Analytical Chemistry 366, no. 4 (February 25, 2000): 379–81. http://dx.doi.org/10.1007/s002160050077.

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41

Napoli, R. M., B. S. Middleditch, N. M. Cintron, and Y. M. Chen. "Isolation and quantitative analysis of hydroxylysine glycosides." Chromatographia 28, no. 9-10 (November 1989): 497–501. http://dx.doi.org/10.1007/bf02261068.

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42

Lunga, Irina, Pavel Chintea, Stepan Shvets, Anna Favelb, and Cosimo Pizza. "Steroidal Glycosides from the Seeds of Hyoscyamus Niger L. and their Antifungal Activity." Chemistry Journal of Moldova 2, no. 1 (December 2007): 108–13. http://dx.doi.org/10.19261/cjm.2007.02(1).05.

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Phytochemical analysis of the seeds of Hyocyamus niger L. (Solonaceae) resulted in the isolation of six steroidal glycosides, two furostanol (1, 2) and four spirostanol saponins (3, 4, 5, 6), which were found in this plant for the first time. The structures of these compounds were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy and MS spectroscopy. The antifungal activity of a crude steroidal glycoside extract, fractions of spirostanoles and individual glicosides was investigated in vitro against a panel of human pathogenic fungi, yeasts as well as dermatophytes and filamentous species.

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43

Yoneyama, Tatsuro, Kanako Iseki, Masaaki Noji, Hiroshi Imagawa, Toshihiro Hashimoto, Sachiko Kawano, Masaki Baba, et al. "Marylosides A-G, Norcycloartane Glycosides from Leaves of Cymbidium Great Flower ‘Marylaurencin’." Molecules 24, no. 13 (July 9, 2019): 2504. http://dx.doi.org/10.3390/molecules24132504.

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Seven novel norcycloartane glycosides, maryloside A–G (1–7), were isolated from the leaves of Cymbidium Great Flower ‘Marylaurencin’, along with a known norcycloartane glycoside, cymbidoside (8). These structures were determined on the basis of mainly NMR experiments as well as chemical degradation and X-ray crystallographic analysis. The isolated compounds (1–6 and 8) were evaluated for the inhibitory activity on lipopolysaccharide (LPS) and interferon-γ (IFN-γ)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Consequently, 1 and 3 exhibited moderate activity.

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Cheng, Lee-Chuen, Vikneswaran Murugaiyah, and Kit-Lam Chan. "Developing a Validated HPLC Method for the Phytochemical Analysis of Antihyperuricemic Phenylethanoid Glycosides and Flavonoids in Lippia nodiflora." Natural Product Communications 12, no. 11 (November 2017): 1934578X1701201. http://dx.doi.org/10.1177/1934578x1701201105.

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The phenylethanoid glycosides and flavonoids of Lippia nodiflora were reported as xanthine oxidase inhibitors that possessed antihyperuricemic effects in chemically-induced hyperuricemic rats. The present study developed a validated high performance liquid chromatography method for the simultaneous phytochemical analysis of five isolated antihyperuricemic constituents in L. nodiflora, comprising two phenylethanoid glycosides, arenarioside (1) and verbascoside (2), and three flavonoids, 6-hydroxyluteolin (3), 6-hydroxyluteolin-7- O-glycoside (4) and nodifloretin (5). These compounds were analysed at 340 nm, using gradient elution of 0.1 % aqueous acetic acid and acetonitrile. The limits of detection were 78.1 ng/mL for 3 and 39.1 ng/mL for the other compounds at a signal-to-noise ratio of 3. The limits of quantification were 312.5 ng/mL for 3 and 156.3 ng/mL for the rest at a signal-to-noise ratio of 12. The intra-day and inter-day accuracy for the five bioactive constituents were between 98.60 % and 100.97 % while their precision values were below 2.11 %. The method was then successfully applied for the quantification of 1-5 in the methanolic extract of L. nodiflora whole plant and its fractions (F1-F4), the methanolic plant part extracts (leaves, stems, roots, and flowers), and water extract of the L. nodiflora whole plant at room temperature.

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45

Rui, Wen, Hongyuan Chen, Yuzhi Tan, Yanmei Zhong, and Yifan Feng. "Rapid Analysis of the Main Components of the Total Glycosides of Ranunculus japonicus by UPLC/Q-TOF-MS." Natural Product Communications 5, no. 5 (May 2010): 1934578X1000500. http://dx.doi.org/10.1177/1934578x1000500521.

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A rapid method for the analysis of the main components of the total glycosides of Ranunculus japonicus (TGOR) was developed using ultra-performance liquid chromatography with quadrupole-time-of-flight mass spectrometry (UPLC/Q-TOF-MS). The separation analysis was performed on a Waters Acquity UPLC system and the accurate mass of molecules and their fragment ions were determined by Q-TOF MS. Twenty compounds, including lactone glycosides, flavonoid glycosides and flavonoid aglycones, were identified and tentatively deduced on the basis of their elemental compositions, MS/MS data and relevant literature. The results demonstrated that lactone glycosides and flavonoids were the main constituents of TGOR. Furthermore, an effective and rapid pattern was established allowing for the comprehensive and systematic characterization of the complex samples.

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Venter, Pieter, Kholofelo Malemela, Vusi Mbazima, Leseilane J. Mampuru, Christo J. F. Muller, and Sylvia Riedel. "An RP-LC-UV-TWIMS-HRMS and Chemometric Approach to Differentiate between Momordicabalsamina Chemotypes from Three Different Geographical Locations in Limpopo Province of South Africa." Molecules 26, no. 7 (March 27, 2021): 1896. http://dx.doi.org/10.3390/molecules26071896.

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Momordica balsamina leaf extracts originating from three different geographical locations were analyzed using reversed-phase liquid chromatography (RP-LC) coupled to travelling wave ion mobility (TWIMS) and high-resolution mass spectrometry (HRMS) in conjunction with chemometric analysis to differentiate between potential chemotypes. Furthermore, the cytotoxicity of the three individual chemotypes was evaluated using HT-29 colon cancer cells. A total of 11 molecular species including three flavonol glycosides, five cucurbitane-type triterpenoid aglycones and three glycosidic cucurbitane-type triterpenoids were identified. The cucurbitane-type triterpenoid aglycones were detected in the positive ionization mode following dehydration [M + H − H2O]+ of the parent compound, whereas the cucurbitane-type triterpenoid glycosides were primarily identified following adduct formation with ammonia [M + NH4]+. The principle component analysis (PCA) loadings plot and a variable influence on projection (VIP) analysis revealed that the isomeric pair balsaminol E and/or karavilagen E was the key molecular species contributing to the distinction between geographical samples. Ultimately, based on statistical analysis, it is hypothesized that balsaminol E and/or karavilagen E are likely responsible for the cytotoxic effects in HT-29 cells.

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47

Li, Yuan, Xin-Lin Li, Chang-Jiang-Sheng Lai, Rui-Shan Wang, Li-Ping Kang, Ting Ma, Zhen-Hua Zhao, Wei Gao, and Lu-Qi Huang. "Functional characterization of three flavonoid glycosyltransferases from Andrographis paniculata." Royal Society Open Science 6, no. 6 (June 2019): 190150. http://dx.doi.org/10.1098/rsos.190150.

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Andrographis paniculata is an important traditional medicinal herb in South and Southeast Asian countries with diverse pharmacological activities that contains various flavonoids and flavonoid glycosides. Glycosylation can transform aglycones into more stable, biologically active and structurally diverse glycosides. Here, we report three glycosyltransferases from the leaves of A. paniculata (ApUFGTs) that presented wide substrate spectra for flavonoid glycosylation and exhibited multi-site glycosylation on the substrate molecules. They acted on the 7-OH position of the A ring and were able to glycosylate several other different types of compounds. The biochemical properties and phylogenetic analysis of these glycosyltransferases were also investigated. This study provides a basis for further research on the cloning of genes involved in glycosylation from A. paniculata and offers opportunities for enhancing flavonoid glycoside production in heterologous hosts. These enzymes are expected to become effective tools for drug discovery and for the biosynthesis of derivatives via flavonoid glycosylation.

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Kulkarni, Narendra Anant, and Jayashree Mane. "Phytochemical Analysis of Selected Medicinal plants of India." Plantae Scientia 2, no. 1 (May 15, 2019): 19–23. http://dx.doi.org/10.32439/ps.v2i1.19-23.

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The present study has revealed the presence of phytochemicals considered as active medicinal chemical constituents. Important medicinal phytochemicals such as terpenoids, flavonoids, phenols, tannins, steroids, glycosides were studied in the collected samples. Plant Aegle marmelos Corr. having all these phytochemicals. Saponin was found only in two plants out of nine plants i.e. Achyranthes aspera Linn. and Semecarpus anacardium Linn. Terpenoids were found in Aegle marmelos Corr., Calotropis gigantea Linn.R.Br., Mimosa pudica Linn. Terpenoids are reported to have anti-inflammatory, antiviral, antimalarial, inhibition of cholesterol synthesis and antibacterial. Cardiac glycosides content was found in Achyranthes aspera Linn., Aegle marmelos Corr., Mimosa pudica Linn., Tribulus terrestris Linn., Calotropis gigantea Linn.R.Br., Ricinus communis Linn.. Cardiac glycosides have been used for over two centuries as a stimulant in case of cardiac failure. The flavonoids were found in Achyranthes aspera Linn., Aegle marmelos Corr., Calotropis gigantea Linn., Mimosa pudica Linn., Cissus quadrangularis Linn. Mart., Tribulus terrestris Linn. The biological functions of flavonoids apart from its antioxidant properties include protection against allergies, inflammation, free radicals, platelet aggregation, microbes, ulcers, hepotoxins, viruses and tumors.

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Carretero, Cristina Recuero, Ana M. Díaz Lanza, Lidia Fernández Matellano, Angel Rumbero Sánchezb, and Lucinda Villaescusa Castillo. "Phytochemical Analysis of Phillyrea latifolia L., a New Source of Oleuropeoside." Zeitschrift für Naturforschung C 56, no. 5-6 (June 1, 2001): 353–56. http://dx.doi.org/10.1515/znc-2001-5-606.

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As a part of our studies on the biologically active substances from Spanish plants, we have undertaken an investigation of the chemical constituents of a typical mediterranean species, Phillyrea latifolia L. (Oleaceae). Two secoiridoid glycosides, three phenylpropanoid glycosides, one lignane and two triterpenic acids were isolated from the leaves of this species and identified. The phytochemical analysis of the aerial parts of P. latifolia revealed that it is a rich source of oleuropeoside.

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Borges, Endler Marcel, Dietrich A. Volmer, and Marcos N. Eberlin. "Comprehensive analysis of Ginkgo tablets by easy ambient sonic spray ionization mass spectrometry." Canadian Journal of Chemistry 91, no. 8 (August 2013): 671–78. http://dx.doi.org/10.1139/cjc-2013-0037.

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We report here that easy ambient sonic spray ionization − mass spectrometry (EASI−MS) allowed direct, rapid, and comprehensive analysis of active components (e.g., terpenetrilactones and intact flavonol glycosides) in Ginkgo tablets. Unlike conventional methods that hydrolyze flavonol glycosides to flavonoids prior to analysis, EASI−MS detects intact flavonol glycosides directly from the tablets enabling differentiation of these natural glycosides from the synthetic flavonoids. Adulteration of Ginkgo tablets is therefore readily recognized in less than 10 s measurement time. Sample preparation is simple and requires only 0.5 mL of methanol and a mortar and pestle. Additionally, no reference standards are needed and a comparison is made to a certified Ginkgo tablet. To demonstrate these abilities, 22 commercial Ginkgo tablets were analyzed by EASI−MS. The data revealed large variations of ingredients and strong deviations from the specified Ginkgo extract levels. These results emphasize the importance of monitoring Ginkgo products using appropriate methodologies as suggested in our work. The technique may replace more demanding LC−MS/MS methods, which can achieve comparable results but are considerably more labor-intensive. Importantly, the presented method is cheaper, faster, and much simpler to operate than chromatography-based mass spectrometric techniques.

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