JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES
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2025
·
IF 2.8
Changhai Sun,Mengxin Xiao,Biyue Cui,Liting Mu,Shuting Zhang,Xinran Zhang,Shushuang Shen
In the current research on Scutellaria baicalensis, a substantial number of flavonoid isomers were identified. Given the limitations of existing analytical methods to accurately identify these isomers, the present study was conducted to determine the flavonoid isomers in Scutellaria baicalensis by combining the mass spectrometry database and stepwise multiple linear regression QSRR model of flavonoids established by the research group in the previous phase. The UHPLC-Q-Exactive Orbitrap-MS technique with isocratic elution injection was employed, and compositional analysis of Scutellaria baicalensis was conducted utilizing the mass spectrometry database to identify two groups of flavonoids and their isomers. The QSRR model was calibrated using standards, and the two groups of flavonoids and their isomers in Scutellaria baicalensis were distinguished and identified utilizing the QSRR model and calibration equation. In this investigation, two groups of flavonoids and their isomers in Scutellaria baicalensis were successfully identified and differentiated. The findings suggest that this QSRR model can be utilized to identify flavonoid isomers, providing a viable method for differentiating isomers of chemical components.
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CHEMISTRY OF NATURAL COMPOUNDS
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2023
·Vol. 59
·期 6
·1067-1074
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IF 0.8
Chen Yi-Fang,Luo Ji-Feng,Zhang Yan-Ni,Wang Yue-Hu
Four flavonoid C -glycosides, including two new diglycosides, dendrodiglycosides A ( 1 ) and B ( 2 ), along with known isoviolanthin ( 3 ) and apigenin 6- C - β -D-glucopyranosyl-(1→2)-α-L-arabinopyranoside ( 4 ), were isolated from the leaves of Dendrobium officinale (Orchidaceae). Their structures were elucidated by NMR and MS. Apigenin 6- C - β -D-glucopyranosyl-(1→2)-α-L-arabinopyranoside exhibited an inhibitory effect against tyrosinase with an IC 50 value of 146.5 μg/mL.
研究领域:
植物化学
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药理学
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MOLECULES
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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
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高影响因子
Separations
·
2022
·Vol. 9
·期 12
·388
·
IF 3.344
Yulin You,Dongxiao Guo,Weiliang Cui,Zhifan Wang,Chunguo Yang,Yongqiang Lin,Shuqi Wang
Matrix-assisted diffusion-ordered spectroscopy (MA DOSY) technology enables efficient the virtual separation of components in a mixture according to their coefficients (D). In the current research, MA DOSY technology was applied for the analysis of a flavonoid mixture. To establish the method, five representative active flavonoid ingredients, including baicalein, baicalin, quercetin, puerarin and rutinum, were selected for the mixture model. The effects of the type and concentration of the matrix, solvent polarity, and nuclear magnetic resonance (NMR) experimental conditions on the resolution of the DOSY spectrum were investigated. It turned out that sodium dodecyl sulfate (SDS) showed the best performance in increasing the resolution of different analytes, which initially increased to the peak below the added amount of 9 mg, and decreased upon the addition of more SDS. In addition, the five flavonoids showed higher resolution in DMSO–d6than in MeOD. Experimental parameters of DOSY, including the number of scans (NS), dummy scans (DS), and value of the FID data points (TD), were also optimized. Finally, the above optimized method was used for the qualitative analysis of the total flavonoid mixture extracted fromScutellaria baicalensisGeorgi. A total of nine compounds were identified and confirmed by comparing them with mass spectrometry data, which further verifies the practical value of this method upon analyzing flavonoid mixtures and provides some reference significance for the follow-up research.Keywords:NMR;MA-DOSY;flavonoids;mixture separation
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FOOD CHEMISTRY
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2014
·
IF 3.259
Yinghua Xie,Yunxia Zheng,Xiling Dai,Quanxi Wang,Jianguo Cao,Jianbo Xiao
The seasonal dynamics of the total flavonoid contents in various parts of Dryopteris erythrosora , a traditional Chinese medicinal fern, and their antioxidant activity were investigated. The total flavonoids content in various parts of D. erythrosora showed an obvious seasonal dynamic change. The total flavonoid contents in stems (from 4.3% to 12.5%) were much higher than that in leaves with an average content of 2.01%. In spring, the total flavonoid contents in stems were relatively low, but increased rapidly from summer to winter. However, the seasonal dynamics of total flavonoid contents in leaves showed different model. The total flavonoid contents in the stems showed a negative correlation with that in the leaves from January to July. The correlation coefficient of about −0.7 was obtained. The antioxidant activity of the extracts also altered in proportion to the change of total flavonoid contents. In general, the extracts from stems always showed highest antioxidant potentials and it was suggested that the stems can be used as crude medicine.
研究领域:
植物学
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药理学
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FOOD HYDROCOLLOIDS
·
2026
·
IF 13.8
Zhiyan Lai,Xin Li,Xiaotian Liu,Siyi Li,Tao Liu
The combination of proteins and flavonoids has been proven to enhance protein stability, increase small molecule solubility, and exhibit additional advantageous properties. However, traditional experimental methods for studying protein-flavonoid binding are inefficient due to complex influencing factors. To address multivariate nonlinear interactions and improve mechanistic reliability, this study established an integrated framework combining machine learning, molecular docking, and systematic experimental validation using phycocyanin—a natural blue pigment with significant bioactivity but prone to degradation under heat, light, and pH variations, limiting its food applications—and two structurally similar flavonoids (rutin and hesperidin) for experimental validation. LightGBM was identified as the optimal predictive model (R 2 > 0.84), revealing key determinants such as molecular weight. The model quantitatively identified structure–property relationships, which were subsequently verified through spectroscopic, physicochemical, and stability analyses. Experimental results demonstrated that both flavonoids induced significant fluorescence quenching in phycocyanin. FT-IR analysis confirmed enhanced hydrogen bonding and hydrophobic interactions, which tightened local protein structures. Surface hydrophobicity measurements further demonstrated reduced exposure of hydrophobic patches after complexation. The complexes exhibited uniformly dispersed particle sizes consistent with model predictions. Critically, rutin and hesperidin improved phycocyanin's UV stability, heat resistance, and color retention. Molecular docking further indicated their binding to critical phycocyanin domains via hydrogen bonding, van der Waals forces, and other interactions. This bidirectional strategy, in which machine learning guides experimental interpretation and experimental results validate predictive outcomes, provides a robust framework for rational design of optimized protein-flavonoid systems in food science.
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PHYTOCHEMISTRY
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2021
·
IF 4.072
Xudong Zhang,Xing Huang,Yan Li,Faqing Tao,Qinshi Zhao,Weiqi Li
Polar auxin transport (PAT) is essential to control root growth. Flavonoids are widely thought to be PAT inhibitors leading to short root developments. However, we found that the flavonoids scutellarin and scutellarein , which both have a 6-hydroxyl group unlike the structure of known flavonoid-PAT-inhibitors, promote PAT in roots. They increase root length; rescue the short roots induced by the PAT-specific inhibitor TIBA; enhance the expression of the PAT mediators PIN1 , PIN2 and AUX1 ; increase the auxin concentration at the quiescent center; and change the distribution of the meristem organizer WOX5. In contrast, rutin and naringenin , which have no 6-hydroxyl group and have different structural features in B-ring, shows the opposite/no effects. Our evidence suggests that flavonoids with and without a 6-hydroxyl group might result in opposite effects on root growth and thus act as chemical switches in regulating PAT.
研究领域:
植物学
·
分子生物学
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LWT-FOOD SCIENCE AND TECHNOLOGY
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2019
·
IF 3.714
Meihui Fan,Huafang Ding,Guowen Zhang,Xing Hu,Deming Gong
Flavonoids possess the inhibition ability against tyrosinase. Here, the effects of flavonoids structure on inhibitory activity and binding affinity of tyrosinase were investigated. The results showed that the hydroxy groups of 5C−OH, 4′C−OH and 5′C−OH of flavonoids were in favor of forming hydrogen bond with the amino acid residues of tyrosinase, which played a crucial role in the binding and interaction between flavonoids and tyrosinase. Different groups of flavonoids exhibited different influences on tyrosinase inhibitory activity and binding affinity. The hydroxylation at C3′ position of flavonoids increased affinities for tyrosinase, whereas the inhibitory activities went downward and upward for flavone and flavonol, respectively. The hydrogenation of the C2 = C3 double bond of flavones weakened inhibitory activities and strengthened affinities, which increased affinities of flavonols with downward and upward inhibitions. The decreased inhibitory activities and affinities can be realized by the hydroxylation of the C4′ and C5′ of flavonoids. Methylation of flavonoids decreased the inhibition while methoxylation of 5′C increased affinity and methylation of 4’−OH led to an increase in affinity. Glycosylation mainly induced the decline in both inhibitory activities and affinities of flavonoids. These findings may provide useful information for the structural modification of flavonoids as effective tyrosinase inhibitors.
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Food & Function
·
2023
·Vol. 14
·期 3
·1357-1368
·
IF 6.1
Min Fu,Lizhi Gao,Qin Geng,Ti Li,Taotao Dai,Chengmei Liu,Jun Chen
The interaction of flavonoid glycosides with milk protein and effects on the functional properties of flavonoid glycoside-β-lactoglobulin complexes are still inexplicit. The noncovalent interactions between flavonoid glycosides including quercetin (QE), quercitrin (QI), and rutin (RU) with β-lactoglobulin (β-LG) were determined by computer molecular docking and multispectral technique analysis. The fluorescence quenching results indicated that the flavonoid glycosides formed stable complexes with β-LG by the static quenching mechanism. The computer molecular docking and thermodynamic parameters analysis conclude that the main interaction of β-LG-QE was via hydrogen bonding, while for β-LG-QI and β-LG-RU it is via hydrophobic forces. The order of binding affinity to β-LG was QE (37.76 × 104 L mol−1) > RU (16.80 × 104 L mol−1) > QI (11.17 × 104 L mol−1), which indicated that glycosylation adversely affected the colloidal complex binding capacity. In this study, the physicochemical properties of the protein-flavonoid colloidal complex were determined. The analysis by circular dichroism spectroscopy demonstrated that flavonoid glycosides made the protein structure looser by inducing the secondary structure of β-LG to transform from the α-helix and β-sheet to random coils. The hydrophobicity of β-LG decreased due to binding with flavonoid glycosides, while functional properties including foaming, emulsification, and antioxidant capacities of β-LG were improved due to the noncovalent interactions. This study presents a part of the insight and guidance on the interactive mechanism of flavonoid glycosides and proteins and is helpful for developing functional protein-based foods.
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
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2020
·
IF 5.162
Jiali Yang,Ting Zhou,Yueming Jiang,Bao Yang
Prenylated flavonoids are good drug candidates due to multiple biological activities and health benefits. Prenyltransferase is an important enzyme involved in the biosynthesis of prenylated flavonoids. In this work, a flavonoid prenyltransferase (AhPT1) from Artocarpus heterophyllus showed an unexpectedly metal ion-induced specificity to flavonoid substrates. AhPT1 could catalyse 6- C -prenylation of genistein when Mg 2+ serving as cofactor. Its catalytic activity to 6-hydroxyflavone was undetectable. However, when Mn 2+ was used instead of Mg 2+ , 5- C -prenylated 6-hydroxyflavone was generated with a high conversion rate. Mn 2+ altered the regiospecificity of AhPT1 and turned it into a 5- C -prenyltransferase. 2′-Hydroxyl could improve the conversion rate of 6-hydroxyflavone, whereas 3′- or 4′-hydroxyl impaired the catalysis efficiency of AhPT1. NQIFDADID174 and DLTDVEGD305 were active motifs involved in substrate binding and catalysis. Asn166, Asp170, Asp174, Asp298, Asp301 and Asp305 in the active center were critical to the prenylation reaction.
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PLANT MOLECULAR BIOLOGY
·
2025
·Vol. 115
·期 4
·1-21
·
IF 3.8
Xu Yao,Li En,Cao Weiping,Zhang Yingchao,Zhang Xinfang,Liu Zhaoyu,Cai Shanshan,Wang Jiayu,Cheng Fansheng,Chen Ruibing,Gao Ting
Scutellaria baicalensis , a traditional medicinal plant originating in China, is widely cultivated for its therapeutic properties. The main bioactive substances in S. baicalensis are flavonoids, which exhibit extensive antibacterial and antiviral activities. However, the contents of these valuable natural product ingredients are relatively low in the plant. MYB transcription factors play crucial roles in regulating plant secondary metabolism, including flavonoid biosynthesis. While the regulation of MYB transcription factors has been extensively studied in various species, research on their role in S. baicalensis remains relatively scarce. In this study, we identified SbMYB111, belonging to the S7 subgroup of R2R3-MYB transcription factors, which functions as a transcriptional activator and is localized in the nucleus. Through heterologous overexpression of SbMYB111 in Arabidopsis thaliana and suppression expression in S. baicalensis , we demonstrated that SbMYB111 acts as a positive regulator in the biosynthesis of flavonoids. Furthermore, the yeast one-hybrid and dual-luciferase reporter gene assays validated that SbMYB111 activates the expression of SbC4H2 , a key enzyme gene in the flavonoid biosynthesis pathway. This study provides a theoretical basis for understanding the transcriptional regulation mechanism of flavonoid synthesis and further developing medicinal resources of S. baicalensis .
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Results in Chemistry
·
2026
·
IF 4.2
Mengqi Wang,Zibo Wu
In this work, we found the flavonoid molecules: quercitrin and hyperoside have potentiality as ultraviolet (UV) filters for the first time. The steady state spectra and time-dependent density functional theory (TDDFT) were used to prove the excited state intramolecular proton transfer (ESIPT) of the non-radiative relaxation. They are excellent potential UVA sunscreens, and they can also provide some UVB protection. We demonstrated the deactivation via ESIPT can be facilitated by the hydrogen bond strengthening in S 1 . In particular, when UV excited, the enol conformation can cross a small barrier to the keto conformation, then the proton transfer process can consumes energy through non-radiative path, and the other small part dissipates through the fluorescence path. Quercetin and hyperoside with a substituent caused 10 nm wavelength change, which opens up a way for the design of new broad-spectrum sunscreens: the adjustable absorption wavelength of sunscreen molecules can be achieved by adjusting the position and number of substituents.
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