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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2020 · IF 3.721

Accumulation pattern of catechins and flavonol glycosides in different varieties and cultivars of tea plant in China

Zhou-Tao Fang,Wen-Ting Yang,Cun-Yu Li,Da Li,Jun-Jie Dong,Dong Zhao,Hai-Rong Xu,Jian-Hui Ye,Xin-Qiang Zheng,Yue-Rong Liang,Jian-Liang Lu

Flavonoids are important phenolic compounds in tea plant since they have a large number of physiological functions for plants themselves and human beings. Tea samples (n = 151) harvested from 3 varieties, 9 plantation areas and 107 cultivars were analyzed to describe the attributes of catechins and flavonol glycosides in China. A support vector machine (SVM) classifier was built to recognize the assamica variety with 94.2 % accuracy. Accumulation of (-)-epicatechin gallate (ECG) and flavonol di-glycosides was especially observed in assamica variety, while (-)-epigallocatechin gallate (EGCG) and flavonol tri-glycosides were obviously accumulated in sinensis variety. The ratios of ECG/EGCG and flavonol tri-glycosides/flavonol di-glycosides could be used as indicators for distinguishing the different varieties and cultivars. Accumulation pattern of catechins and flavonol glycosides were mainly dependent on the genetic background of the cultivars rather than plantation locations. The increased hydroxyl groups at the C-ring of catechins and the extended sugar chain at the B-ring of flavonol glycosides could be considered as important rules of metabolite change during tea plant evolution. The mechanism of accumulation of flavonoids in various varieties and cultivars was also discussed.

CAS / MDL: 64-18-6
研究领域: 植物学 · 代谢组学 · 食品科学
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PLANT PHYSIOLOGY AND BIOCHEMISTRY · 2025 · IF 5.7

Genome-wide identification of UDP-glycosyltransferases involved in flavonol glycosylation induced by UV-B irradiation in Eriobotrya japonica

Jiafei Qian,Chuanhong Ren,Fan Wang,Yunlin Cao,Yan Guo,Xiaoyong Zhao,Yilong Liu,Changqing Zhu,Xiaoying Li,Hongxia Xu,Junwei Chen,Kunsong Chen,Xian Li

Flavonol glycosides are secondary metabolites important for plant development and stress defense such as UV-B irradiation. UDP-glycosyltransferase (UGT) is the last enzyme step that catalyzes flavonol glycosides biosynthesis. Eriobotrya japonica is abundant in flavonol glycosides, but UGTs responsible for accumulation of flavonol glycosides remain unknown. Here, 13 flavonol glycosides including monoglycosides and diglycosides were characterized in different tissues of loquat by LC-MS/MS. UV-B irradiation significantly increased the accumulation of four quercetin glycosides and two kaempferol glycosides in loquat fruit. Based on UGT gene family analysis, transcriptome analysis, enzyme assays of recombinant proteins as well as transient overexpression assays in Nicotiana benthamiana , three UGTs were identified, i.e. EjUGT78T4 as flavonol 3- O -galactosyltransferase, EjUGT78S3 as flavonol 3- O -glucosyltransferase, and EjUGT91AK7 as flavonol 1→6 rhamnosyltransferase. This work elucidates the formation of flavonol glycosides in loquat through UGT-mediated glycosylation.

研究领域: 植物学 · 分子生物学 · 代谢组学
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CRYSTAL GROWTH & DESIGN · 2016 · IF 4.425

Insights into Cocrystal Polymorphic Transformation Mechanism of Ethenzamide–Saccharin: A Combined Experimental and Simulative Study

Yao Tong,Zhanzhong Wang,Entao Yang,Bochen Pan,Leping Dang,Hongyuan Wei

In this work, the solvent-mediated phase transformation of the metastable form (Form II) to the stable form (Form I) of ethenzamide–saccharin cocrystal in isopropanol was investigated. Solubility of Form I and Form II in pure isopropanol was also measured. The transformation mechanism from Form II to Form I was analyzed by some online and off-line tools including attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy, Raman spectroscopy, and polarizing microscopy. The results demonstrate that the transformation process consists of three steps, involving the dissolution of Form II, the nucleation of Form I, and the following growth of Form I. The ATR-FTIR and Raman results show that the polymorphic transformation from Form II to Form I is controlled by the nucleation and growth of Form I. Furthermore, the microscope photographs clearly reveal that the Form I preferably nucleates and grows on the (100) surface of Form II. The molecular simulation results indicate that higher adsorption energy and the exposure of more activity groups make the molecule adsorbed more strongly on the (100) surface, which is in agreement with the experimental observation. The results drawn in this work will be of great significance to control the formation of a desired polymorphic final product of ethenzamide–saccharin cocrystal.

研究领域: 材料科学 · 化学工程
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2017 ·Vol. 98 ·期 4 ·1574-1583 · IF 2.463

Characterization of steryl glycosides in marine microalgae by gas chromatography–triple quadrupole mass spectrometry (GC–QQQ-MS)

Shanshan Yu,Yufan Zhang,Yun Ran,Wenyi Lai,Zhaoshou Ran,Jilin Xu,Chengxu Zhou,Xiaojun Yan

BACKGROUND Steryl glycosides (SGs) are sterol conjugates found in various plants, especially in those making up human diets. It has been demonstrated that SGs have potential health benefits, and they could be used as food supplements in a variety of food matrixes. Marine microalgae are a potential resource for human food and ingredients. In this study, gas chromatography–triple quadrupole mass spectrometry (GC–QQQ-MS) was used to characterize unknown SGs in eight microalgae belonging to different classes ( Isochrysis galbana 3011, Pavlova viridis , Platymonas helgolandica , Conticribra weissflogii , Thalassiosira pseudonana , Nitzschia closterium , Gymnodinium sp., and Karlodinum veneficum ). RESULTS The SGs were first extracted from lyophilized algae with chloroform–methanol, purified by solid-phase extraction and analyzed as trimethylsilyl derivatives. Nine SGs have been identified. In particular, new SGs like occelasteryl glycoside and stellasteryl glycoside were found in Gymnodinium sp., 24-methylene cholesteryl glycoside was detected in P. helgolandica , and 4,24-dimethylcholestan-3-yl glycoside was identified as the main constituent of microalga K. veneficum . The results also showed that the compositions of SGs in different microalgae varied, with a range of 5.234 to 0.036 g kg −1 , and microalga P. viridis contained the most abundant SGs. CONCLUSION GC–QQQ-MS is a powerful tool to detect SGs with different structures from a variety of microalgae. The compositions of SGs in different microalgae varied greatly. Microalgae are a good source of highly valued SGs. © 2017 Society of Chemical Industry

CAS / MDL: 110-54-3
研究领域: 海洋生物学 · 分析化学 · 食品科学
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NATURAL PRODUCT RESEARCH · 2020 · IF 2.158

Two new chemical constituents from the rhizomes of Actaea dahurica

Sen-Ju Ma,Hai-Bo Li,Jun-Ran Shao,Qian-Qian Pang,Ting Li,Xin-Sheng Yao,Yang Yu

A new phenylpropanoid allopyranoside (1) and a new indolinone alkaloid (2) were isolated from the rhizomes of Actaea dahurica (syn. Cimicifuga dahurica). The structures of those two compounds were deduced as cimicifugaside F (1) and 3E,11E-(3-methyl-2-butenylidene acid)-2-indolinone-1-O-β-d-glucopyranoside (2) by detailed analysis of their MS, 1D and 2D NMR data and comparison with literatures. Additionally, the isolates were evaluated for their inhibitory effects on the production of NO by LPS-stimulated RAW 264.7 macrophages.

CAS / MDL: 298-93-1
研究领域: 植物化学 · 药理学
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FOOD RESEARCH INTERNATIONAL · 2023 · IF 8.1

Impact of molecular interactions between hydrophilic phytosterol glycosyl derivatives and bile salts on the micellar solubility of cholesterol

Yuyuan Hu,Chuanguo Ma,Ruinan Yang,Shujing Guo,Tong Wang,Jun Liu

Hydrophilic phytosterol glycosyl derivatives are synthetic phytosterol analogues by coupling with the glycosyl moiety to improve the water solubility and bioaccessibility of free phytosterols. The aim of this study is to clarify the molecular interaction of phytosterol glycosyl derivatives with bile salts and the consequent impact on cholesterol solubilization. Sharp nonlinear decrease in the micellar solubility of cholesterol and accompanying changes in particle size, zeta potential and microtopography of mixed micelles were observed when phytosterol glycosyl derivatives were introduced in cholesterol-loaded bile salt micelles. These results suggested that β -sitosterol glycosyl derivatives molecules indeed participated in the formation of mixed micelles. Further, nuclear magnetic resonance showed that the structural change of mixed micelles was caused by the insertion of β -sitosterol glycosyl derivatives via hydrogen bonds with sodium taurocholate, which resulted in the low cholesterol solubilization. Moreover, the hydrogen-bond interactions were apparently influenced by the glycosyl moiety of β -sitosterol glycosyl derivatives. These molecular mechanisms may contribute to the development of cholesterol-absorption inhibitors.

CAS / MDL: 83-46-5
研究领域: 药学 · 化学 · 生物化学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

Simultaneous determination of the monosaccharide types and their absolute configurations in polysaccharides based on UPLC-MS/MS

Yongchun Huang,Jie Bai,Jinman Shui,Zhanhai Su,Chengzhu Cao,Haiyan Wang,Qiong Wu,Shoude Zhang

Analysing monosaccharide composition is an essential step in deciphering polysaccharide structures. However, it presents significant challenges due to the pronounced hydrophilicity and the vast array of monosaccharide isomers. Gas/liquid chromatography, coupled with an aldononitrile acetate derivatisation, has been widely used for monosaccharide composition analysis. However, it poses considerable difficulties in simultaneously determining the D/L configurations of these monosaccharides. In this study, a novel method that can simultaneously determine the composition of polysaccharides and their D/L configuration based on L-cysteine methyl ester derivatisation (CMED) and ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) is developed for the comprehensive analysis of monosaccharide types. This method enables the simultaneous characterization of aldoses, ketoses, alditols, and uronic acids. Furthermore, the reaction mechanisms and by-products were meticulously analysed, offering a robust theoretical basis for this novel methodology. Additionally, the developed method was employed to characterize the monosaccharide composition for six plant polysaccharides. Ultimately, the findings demonstrated that the proposed method is effective for confirming monosaccharide composition, encompassing both structural types and absolute configurations.

研究领域: 分析化学 · 碳水化合物化学 · 生物化学 · 植物科学
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Horticulture Research · 2022 · IF 7.291

Identification of UDP-rhamnosyltransferases and UDP-galactosyltransferase involved in flavonol glycosylation in Morella rubra

Ren Chuanhong,Guo Yan,Xie Linfeng,Zhao Zhikang,Xing Mengyun,Cao Yunlin,Liu Yilong,Lin Jing,Grierson Donald,Zhang Bo,Xu Changjie,Chen Kunsong,Li Xian

Flavonol glycosides are health-promoting phytochemicals important for human nutrition and plant defense against environmental stresses. Glycosylation modification greatly enriches the diversity of flavonols. Morella rubra, a member of the Myricaceae, contains high amounts of myricetin 3-O-rhamnoside (M3Rha), quercetin 3-O-rhamnoside (Q3Rha), and quercetin 3-O-galactoside (Q3Gal). In the present study, MrUGT78R1 and MrUGT78R2 were identified as two functional UDP-rhamnosyltransferases, while MrUGT78W1 was identified as a UDP-galactosyltransferase. Site-directed mutagenesis identified Pro143 and Asn386 as important residues for rhamnosyl transfer activity of MrUGT78R1, while the two corresponding positions in MrUGT78W1 (i.e. Ser147 and Asn370) also play important roles in galactosyl transfer activity. Transient expression data for these three MrUGTs in Nicotiana benthamiana tested the function of MrUGT78R1 and MrUGT78R2 as rhamnosyltransferases and MrUGT78W1 as a galactosyltransferase in glycosylation of flavonols. This work enriches knowledge of the diversity of UDP-rhamnosyltransferase in planta and identifies two amino acid positions important for both rhamnosyltransferase and galactosyltransferase.

研究领域: 植物科学 · 生物化学 · 分子生物学
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