MOLECULES
·
2015
·Vol. 20
·期 5
·7683-7699
·
IF 2.416
Ying Zhou,Datong Wu,Pengfei Cai,Guifang Cheng,Chaobiao Huang,Yuanjiang Pan
A microwave-assisted extraction approach based on ionic liquids of different chain lengths was successfully applied to the extraction of ten flavonoid glycosides from the flowering heads ofChrysanthemum morifoliumRamat. The pretreated sample was quantified by HPLC-ESI-MSn. The main components were identified as flavonoid glycosides, including three luteolin glycosides, three apigenin glycosides, three kaempferide glycosides, and one acacetin glycoside according to the characteristics of the corresponding CID mass spectrometric patterns. Eight ionic liquids from the imidazolium family with different chain lengths, namely, 1-alkyl-3-methylimidazolium bromide, [Cnmim]Br, (n = 2–16) were studied as extraction medium in water. Results indicated that alkyl chain length had an irregular impact on the extraction efficiency. Moreover, the best extraction efficiency was achieved by 1-dodecyl-3-methylimidazolium bromide aqueous solution ([C12mim]Br). Besides the alkyl chain length of the cations, other factors influencing extraction efficiency were systematically investigated, including concentration of the IL solutions, extraction time, matrix-to-solvent ratio and irradiation power.Keywords:ionic liquids;flavonoid glycosides;microwave-assisted extraction;Chrysanthemum morifoliumRamat
研究领域:
植物化学
·
分析化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Horticultural Plant Journal
·
2017
·Vol. 3
·期 4
·165-171
·
IF 0
Yanhui ZHANG,Peiying LIU,Qianqian KONG,Shiyan XING,Xiaojing LIU,Limin SUN
Flavonoids and terpene trilactones, especially, ginkgo flavonglycosides, ginkgolides and bilobalides in leaves of ginkgo trees, need to be studied for effective application of these active components with high medical and health-care values. This study was aimed to provide scientific bases for genealogies selection and harvest season confirmation for Ginkgo biloba . A high-performance liquid chromatographic method (HPLC-ELSD) was developed to determine the contents of terpene trilactone and flavonoid of 36 ancient G. biloba genealogies from 19 provinces in China. The study indicated that the content gradually increased from April to August, and thereafter declined. Analysis of variance indicated that the contents of terpene trilactone, flavonoids, and their respective components had significant difference among 36 genealogies. The cluster analysis showed that No. 72 (Xing'an, Guangxi), No. 58 (Youyang, Chongqing), No. 82 (Rugao, Jiangsu), No. 123 (Huixian, Gansu), No. 99 (Dujun, Guizhou), No. 10 (Tai'an, Shandong) and No. 133 (Mentougou, Beijing) genealogies have higher content of terpene trilactone and flavonoid. These results can help us to select superior variety containing high content of terpene trilactone and flavonoid.
研究领域:
植物化学
·
药用植物学
·
天然产物化学
·
林木遗传育种
·
药物代谢
✓ 已验证
DOI
MOLECULES
·
2016
·Vol. 21
·期 9
·1148
·
IF 2.465
Shuxia Yan,Xianan Zhang,Xin Wen,Qiang Lv,Changjie Xu,Chongde Sun,Xian Li
Chinese bayberry (Morella rubraSieb. et Zucc.) fruit have a diverse flavonoid composition responsible for the various medicinal activities, including anti-diabetes. In the present study, efficient simultaneous purification of four flavonoid glycosides, i.e., cyanidin-3-O-glucoside (1), myricetin-3-O-rhamnoside (2), quercetin-3-O-galactoside (3), quercetin-3-O-rhamnoside (4), from Chinese bayberry pulp was established by the combination of solid phase extract (SPE) by C18 Sep-Pak®cartridge column chromatography and semi-preparative HPLC (Prep-HPLC), which was followed by HPLC and LC-MS identification. The purified flavonoid glycosides, as well as different fractions of fruit extracts of six bayberry cultivars, were investigated for α-glucosidase inhibitory activities. The flavonol extracts (50% methanol elution fraction) of six cultivars showed strong α-glucosidase inhibitory activities (IC50= 15.4–69.5 μg/mL), which were higher than that of positive control acarbose (IC50= 383.2 μg/mL). Four purified compounds1–4exerted α-glucosidase inhibitory activities, with IC50values of 1444.3 μg/mL, 418.8 μg/mL, 556.4 μg/mL, and 491.8 μg/mL, respectively. Such results may provide important evidence for the potential anti-diabetic activity of different cultivars of Chinese bayberry fruit and the possible bioactive compounds involved.Keywords:Morella rubrafruit;α-glucosidase inhibitory activity;flavonoid glycosides;purification
研究领域:
药理学
·
植物学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
RAPID COMMUNICATIONS IN MASS SPECTROMETRY
·
2017
·Vol. 32
·期 3
·262-268
·
IF 1.998
Xiafen Xu,Xinhui Li,Xianrui Liang
Rationale Metabolites of isoflavones have attracted much attention in recent years due to their potential bioactivities. However, the complex constituents of the metabolic system and the low level of metabolites make them difficult to analyze. A mass spectrometry (MS) method was applied in our identification of metabolites and study of their fragmentation pathways due to the advantages of rapidity, sensitivity, and low level of sample consumption. Methods Three isoflavone glycosides and their metabolites were identified using ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry (UPLC/QTOF-MS). These metabolites were obtained by anaerobically incubating three isoflavone glycosides with human intestinal flora. The characteristic fragments of isoflavone glycosides and their metabolites were used for the identification work. Results Two metabolites from ononin, three metabolites from irilone-4′- O -β-D-glucoside, and five metabolites from sissotrin were identified respectively by the retention time (RT), accurate mass, and mass spectral fragmentation patterns. The losses of the glucosyl group, CO from the [M+H] + ion were observed for all the three isoflavone glycosides. The characteristic retro-Diels-Alder (RDA) fragmentation patterns were used to differentiate the compounds. The metabolic pathways of the three isoflavone glycosides were proposed according to the identified chemical structures of the metabolites. Conclusions A selective, sensitive and rapid method was established for detecting and identifying three isoflavone glycosides and their metabolites using UPLC/QTOF-MS. The established method can be used for further rapid structural identification studies of metabolites and natural products. Furthermore, the proposed metabolic pathways will be helpful for understanding the in vivo metabolic process of isoflavone.
研究领域:
分析化学
·
药理学
·
营养学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
CARBOHYDRATE RESEARCH
·
2021
·
IF 2.104
Ting Zhou,Wei Guo,Shengchao Ren,Yuming Li,Jinming Wu,Bao Yang
The peel of Citrus reticulate ‘Chachiennsis’ (Chachi) is a well-known functional food with multiple health benefits in Asia. There is an old saying “the longer time Chachi is stored, the better health benefits it has”. Is it convincible? What are the critical bioactive compounds in Chachi? To answer these questions, gas chromatography-mass spectrometry (GC-MS) and ultrahigh performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) were used to qualify and quantify the flavonoid glycosides and other bioactive compounds of Chachi with storage time of 5–20 years. Limonene was the representative volatile compound . The level of most volatile compounds decreased along with storage. Sixteen flavonoids glycosides and twenty flavonoids were identified. Nobiletin , hesperitin, tetramethoxy flavone and pentamethoxy flavone were characteristic bioactive compounds for Chachi. Most of them accumulated during 10-year storage, thereafter decreased. Ten years could be the optimal storage time. These results indicated that the old saying should be corrected.
研究领域:
食品科学
·
植物化学
✓ 已验证
DOI
高影响因子
INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY
·
2024
·Vol. 59
·期 9
·6462-6472
·
IF 2.6
Tian Siyi,Chang Guoli,Xiang Yannan,Cai Chenggang,Luo Xinyu,Zhu Ruiyu,Yang Hailong,Gao Haiyan
In order to investigate the hypoglycaemic mechanism and potential applications of four hypoglycaemic flavonoid glycosides, namely myricitrin, Cyanidin-3-O-glucoside (C3G), hyperoside and quercitrin in Myrica rubra pomace, the stability of these four flavonoid glycosides and their binding mechanisms were studied using molecular docking. The results demonstrated that pH value affects on the stability of these four components in M. rubra pomace. C3G exhibited the most significant inhibitory effect on α-glucosidase at pH 5, with myricitrin, hyperoside and quercitrin showing the highest inhibitory effect at pH 7. Moreover, an increase in temperature and storage time reduced the inhibitory effect of these four glycosidic components on α-glucosidase. Molecular docking analysis revealed that myricitrin formed hydrogen bonds with the active site residues of α-glucosidase, namely Phe550, Ile552, Asp555, Ser574 and Arg576, and also engaged in hydrophobic interactions with Lys551. Hyperoside formed hydrogen bonds with α-glucosidase, formed hydrophobic interactions with Lys50 and exhibited π-cation interaction with Lys53. Quercitrin formed hydrogen bonds with α-glucosidase, formed hydrophobic interactions with Lys500 and established salt bridges with Lys50. C3G formed hydrogen bonds and hydrophobic interactions with α-glucosidase and showed π-π interactions with Phe301. These findings will provide valuable insights for the application of these four chemicals.
研究领域:
食品科学
·
药理学
✓ 已验证
DOI
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
·
2016
·
IF 3.169
Bo Zhuang,Li-Li Dou,Ping Li,E-Hu Liu
Deep eutectic solvents (DESs) are emerging as alternatives to conventional ionic liquids and organic solvents due to their unique advantages. In the present study, the tuneability of DESs as tailor-made solvents to efficiently extract polar and non-polar bioactive compounds from Platycladi Cacumen was detailedly investigated. Totally 12 types of choline chloride-, betaine-, and l-proline-based DESs were synthesized for initial screening, and extraction conditions was optimized by single-factor experiment. Experiments with different DESs and principal components analysis demonstrated that the extractability of both flavonoid glycosides and aglycones was greater with certain designed DESs than conventional solvents. In addition, the water content in DESs led to significantly different extraction yields of flavonoid compounds. The target compounds were recovered from DESs by macroporous resin LX-38 with a satisfactory yield between 77.44% and 98.92%. The knowledge acquired in this study could contribute to further DES application in extraction of bioactive compounds from natural sources.
研究领域:
植物化学
·
天然产物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2019
·Vol. 24
·期 16
·3016
·
IF 3.06
Ying Xue,Lin-Sen Qing,Li Yong,Xian-Shun Xu,Bin Hu,Ming-Qing Tang,Jing Xie
So far, there is no report on the quality evaluation of lemonade available in the market. In this study, a sample preparation method was developed for the determination of flavonoid glycosides by ultra-performance liquid chromatography–mass spectrometry (UPLC-MS) based on vortex-assisted dispersive liquid-liquid microextraction. First, potential flavonoids in lemonade were scanned and identified by ultra-performance liquid chromatography–time of flight mass spectrometry (UPLC-TOF/MS). Five flavonoid glycosides were identified as eriocitrin, narirutin, hesperidin, rutin, and diosmin according to the molecular formula provided by TOF/MS and subsequent confirmation of the authentic standard. Then, an ultra-performance liquid chromatography–triple quadrupole mass spectrometry (UPLC-QqQ/MS) method was developed to determine these five flavonoid glycosides in lemonade. The results showed that the content of rutin in some lemonade was unreasonably high. We suspected that many illegal manufacturers achieved the goal of low-cost counterfeiting lemonade by adding rutin. This suggested that it was necessary for relevant departments of the state to make stricter regulations on the quality standards of lemonade beverages.Keywords:vortex-assisted dispersive liquid-liquid microextraction;flavonoid glycoside;UPLC-MS;counterfeiting lemonade
研究领域:
分析化学
·
食品科学
·
药物分析
✓ 已验证
产品关联
DOI
PubMed
高影响因子
Journal of Chemistry
·
2021
·
IF 2.506
Xinxin Chen,Junmao Li,Renyikun Yuan,Youqiong Zhuo,Yangling Chen,Chenwei Zhang,Ming Chen,Hong-Wei Gao,Zhenjie Liu,Yulin Feng,Zheng-Tao Wang,Shilin Yang
Ilicis Rotundae Cortex (IRC) consists of the bark of Ilex rotunda Thunb, and its chemical constituents mainly include flavonoid glycosides, phenols, and triterpenoid saponins. In this study, a preliminary analysis was performed to identify and obtain the chemical components from IRC to better control the quality of the medicinal materials and provide a chemical basis for the study of the efficacy of the active components. Simple and efficient sample pretreatment and ultrasonic-assisted extraction methods were used to analyze the mass spectrum fragments and fracture modes in the anion mode by UPLC-Q-TOF-MS/MS. Using a two-step strategy, the neutral loss, diagnostic ions, and characteristic fragments were studied to screen diverse skeletons and substitutions, and the possible compounds were identified by comparison with databases. The representative compounds were compared with the standard, and the mass spectrogram was found to match perfectly. Thus, our findings reveal that this method is feasible and reliable and can be used to analyze the chemical components of IRC. We identified 105 compounds, including 22 triterpenoid saponins, 15 chlorogenic acids, 33 phenylpropanoids and phenylpropanosides, 3 iridoids, 1 flavonoid, 10 lignans, 12 glycosides, and 9 other compounds. This method lays the foundation for further elucidating the pharmacodynamics of IRC and provides a practical method for the identification of IRC.
研究领域:
中药学
·
分析化学
✓ 已验证
产品关联
DOI
高影响因子
FITOTERAPIA
·
2019
·
IF 2.431
Rui Li,Qing Wang,Menghao Zhao,Peiming Yang,Xiao Hu,Danwei Ouyang
Hippophae rhamnoides subsp. Sinensis is a famous traditional medicinal plant in Tibet and Mongolia of China. Three novel flavonoid glycosides and ten known analogues were obtained from the seeds of H. rhamnoides . The structures of new compounds were elucidated by spectroscopics, chemical methods as well as literature data. In vitro assay, compounds 5–9 , kaempferol and 70% ethanolic elution fraction showed prominent α -glucosidase inhibitory activities with IC 50 values ranging from 8.30 to 112.11 μM, better than that of the positive control, acarbose , whose IC 50 value was 1727.07 μM.
研究领域:
植物化学
·
药理学
✓ 已验证
DOI
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2025
·
IF 8
Zihao Chen,Min Fu,Jun Chen,Guowen Zhang,Qin Geng,Xing Hu,Yihui Wang,Ti Li,Ruihong Liang,Taotao Dai
Flavonoids offer various health benefits due to their chemical properties and non-covalent interactions with food nutrients. Despite extensive research on flavonoid-protein interactions, the effects of flavonoid glycosides on pea protein (PP) remained unclear. This study explored the non-covalent interactions of luteolin (Lu), isoorientin (Iso), and cynaroside (Cyn) with PP using molecular docking and multi-spectral techniques. Results showed that Lu interacted with PP mainly through hydrophobic forces, while Iso and Cyn interacted predominantly via hydrogen bonding. At 298 K, the binding affinity of flavonoids to PP was ranked as Lu (16.98 × 10 4 M −1 ) > Iso (7.41 × 10 4 M −1 ) > Cyn (6.31 × 10 4 M −1 ). Circular dichroism analysis showed that flavonoid glycosides loosened the protein structure by inducing a change in the secondary structure of PP from an α-helix to a random coil. This resulted in improved foaming, emulsification, and antioxidant properties of PP. This study provided insights into flavonoid-protein interactions and their potential applications in functional protein foods.
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
PHYTOCHEMICAL ANALYSIS
·
2024
·Vol. 35
·期 6
·1428-1442
·
IF 3
Sijie Zhang,Xingchu Gong,Haibin Qu
Introduction Previously reported preparation methods of Ginkgo biloba leaf extract (EGBL) have mainly focused on the enrichment of flavonoid glycosides (FG) and terpene trilactones (TT), which led to the underutilization of G. biloba leaves (GBL). Objectives To make full use of GBL, in this study, a comprehensive optimization strategy for preparing EGBL by macroporous resin column chromatography was proposed and applied to enrich FG, TT, and shikimic acid (SA) from GBL. Methodology Initially, the static adsorption and desorption were executed to select suitable resin. Then, the influences of solution pH were investigated by the static and dynamic adsorption. Subsequently, eight process parameters were systematically investigated via a definitive screening design (DSD). After verification experiments, scale-up enrichment was carried out, investigating the feasibility of the developed strategy for application on an industrial scale. Results It was found that XDA1 was the most appropriate adsorbent for the preparation of EGBL at solution pH 2.0. Furthermore, based on the constraints of the desired quality attributes, the optimized ranges of operating parameters were successfully acquired, and the verification experiments demonstrated the accuracy and reliability of using DSD to investigate the chromatography process for the preparation of EGBL. Finally, magnified experiments were successfully performed, obtaining the EGBL containing 26.54% FG, 8.96% TT, and 10.70% SA, which reached the SA level of EGB761, an international standard EGBL. Conclusion The present study not only provided an efficient and convenient approach for the preparation of EGBL enriched in SA but also accelerated efforts to high-value utilization of GBL.
研究领域:
植物化学
·
中药学
·
分离纯化技术
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）