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Glucuronic acid metabolites of phenolic acids target AKT-PH domain to improve glucose metabolism

Chinese Herbal Medicines 2023年第3期15卷 398-406页

作者： Jie Gao Manqian Zhang Xingwang Zu Xue Gu Erwei Hao Xiaotao Hou Gang Bai State Key Laboratory of Medicinal Chemical Biology College of Pharmacy and Tianjin Key Laboratory of Molecular Drug ResearchNankai UniversityTianjin 300353China Guangxi Key Laboratory of Efficacy Study on Chinese Materia Medica Guangxi Collaborative Innovation Center for Research on Functional Ingredients of Agricultural ResiduesGuangxi University of Chinese MedicineNanning 530200China

Objective:phenolic acids widely exist in the human diet and exert beneficial effects such as improving glucose metabolism.It is not clear whether phenolic acids or their metabolites play a major role in vivo.In this study,caffeic acid(CA)and ferulic acid(FA),the two most ingested phenolic acids,and their glucuronic acid metabolites,caffeic-4’-O-glucuronide(CA4G)and ferulic-4’-O-glucuronide(FA4G),were investigated.Methods:Three insulin resistance models in vitro were established by using TNF-a,insulin and palmitic acid(PA)in HepG2 cells,respectively.We compared the effects of FA,FA4G,CA and CA4G on glucose metabolism in these models by measuring the glucose consumption levels.The potential targets and related pathways were predicted by network pharmacology.Fluorescence quenching measurement was used to analyze the binding between the compounds and the predicted target.To investigate the binding mode,molecular docking was performed.Then,we performed membrane recruitment assays of the AKT pleckstrin homology(PH)domain with the help of the PH-GFP plasmid.AKT enzymatic activity was determined to compare the effects between the metabolites with their parent compounds.Finally,the downstream signaling pathway of AKT was investigated by Western blot analysis.Results:The results showed that CA4G and FA4G were more potent than their parent compounds in increasing glucose consumption.AKT was predicted to be the key target of CA4G and FA4G by network pharmacology analysis.The fluorescence quenching test confirmed the more potent binding to AKT of the two metabolites compared to their parent compounds.The molecular docking results indicated that the carbonyl group in the glucuronic acid structure of CA4G and FA4G might bind to the PH domain of AKT at the key Arg-25 site.CA4G and FA4G inhibited the translocation of the AKT PH domain to the membrane,while increasing the activity of AKT.Western blot analysis demonstrated that the metabolites could increase the phosphorylation of AKT and downstream glycogen synthase kinase 3βin th

关键词： AKT glucuronic acid glucose metabolism metabolite phenolic acid PH domain

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Theoretical and experimental cocrystal screening of temozolomide with a series of phenolic acids, promising cocrystal coformers

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Chinese Chemical Letters 2024年第5期35卷 407-417页

作者： Hongmei Yu Baoxi Zhang Meiju Liu Cheng Xing Guorong He Li Zhang Ningbo Gong Yang Lu Guanhua Du Beijing Key Laboratory of Polymorphic Drugs Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China Beijing City Key Laboratory of Drug Target Identification and Drug Screening Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

The virtual cocrystal screening approach based on molecular electrostatic potential surface(MEPS)maps is a fast and feasible computational method to estimate the probability of cocrystal formation by calculating the difference in the interaction site pairing energies of monomers and that of their assemblies prior to experimental screening.In this paper,we report 12 cocrystal forms of temozolomide with mono-,di-,and trihydroxy benzoic acids,namely,3-hydroxy-,2,4-dihydroxy-,2,5-dihydroxy-,2,6-dihydroxy-,3,4-dihydroxy-,and 3,4,5-trihydroxy-benzoic acids,as well as benzoic acid,as pharmaceutical coformers for the first time.10 single crystals out of the 12 cocrystal forms were obtained and unequivocally determined by single-crystal X-ray diffraction,which clarified spatial arrangements,molecular conformations,and supramolecular synthons.MEPS further gains some insights into the sites of hydrogen bonding interactions for exploring combination patterns in these assemblies.Modulated stability of TMZ was successfully achieved by cocrystallization with these acids.

关键词： Virtual Cocrystal Temozolomide Supramolecular synthon phenolic acid Stability

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Improvement of Selectivity with Boric acid in Separating phenolic acids by Capillary Zone Electrophoresis

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Chinese Chemical Letters 1998年第1期9卷 87-91页

作者： Hong LONG Ai Jin HUANG Yi Liang SUN(Department of Chemistry, Peking University, Beijing 100871) Department of Chemistry Peking University Beijing 100871 China

It was shown that in capillary electrophoresis (CE) the addition of boric acid as a complexing agent in phosphate buffer can modulate the separation selectivity of phenolic acids.

关键词： capillary electrophoresis boric acid separation phenolic acid

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A New phenolic acid from Rhizomes of Abacopteris penangiana

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Chinese Herbal Medicines 2010年第3期2卷 165-167页

作者： ZHAO Zhong-xiang1,2, RUAN Jin-lan2, JIN Jing3, CAI Ya-ling2, ZHU Chen-chen1, YU Yang1 1. School of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510006, China 2. Tongji College of Pharmacy, Huazhong University of Science and Technology, Wuhan 430030, China 3. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510275, China School of Chinese Materia Medica Guangzhou University of Chinese MedicineGuangzhou 510006China Tongji College of Pharmacy Huazhong University of Science and TechnologyWuhan 430030China Tongji College of Pharmacy Huazhong University of Science and TechnologyWuhan 430030China School of Pharmaceutical Sciences Sun Yat-sen UniversityGuangzhou 510275China School of Chinese Materia Medica Guangzhou University of Chinese MedicineGuangzhou 510006China

Objective To study the chemical constituents of Abacopteris penangiana. Methods The compounds were separated and purified by various chromatographic techniques and their structures were elucidated on the basis of physiochemical properties and spectroscopic methods. Results Seven compounds were purified and their structures were identified as: (7′Z)-3-O-(3,4-dihydroxy phenylethenyl)-caffeic acid (1), caffeicin B (2), matteucinol (3), protocatechuic acid (4), p-methoxybenzoic acid (5), β-sitosterol (6), and daucosterol (7). Conclusion Compound 1 is a new phenolic acid compound named abacopteric acid, and the other compounds are isolated from the plant for the first time.

关键词： Abacopteris penangiana abacopteric acid phenolic acid

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Rapid Profiling and Characterization of the Multicomponents from the Root and Rhizome of Salvia miltiorrhiza by Ultra-High Performance Liquid Chromatography/Ion Mobility-Quadrupole Time-of-Flight Mass Spectrometry in Combination with Computational Peak Annotation Workflows

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Phyton-International Journal of Experimental Botany 2022年第5期91卷 1073-1088页

作者： Boxue Chen Hongda Wang Meiyu Liu Wandi Hu Yuexin Qian Jiali Wang Jie Liu Xue Li Jing Wang Wenzhi Yang State Key Laboratory of Component-Based Chinese Medicine&Tianjin Key Laboratory of TCM Chemistry and Analysis Tianjin University of Traditional Chinese MedicineTianjin301617China Waters Technology Co. Ltd.Beijing101102China

Herbal components characterization represents a challenging task because of the co-existing of multiple classes of naturally occurring compounds with wide spans of polarity,molecular mass,and the ubiquitous isomerism.The root and rhizome of Salvia miltiorrhiza have been utilized as a reputable traditional Chinese medicine Salviae Miltiorrhizae Radix et Rhizoma(Dan-Shen)in the treatment of cardiovascular disease.Herein,a dimensionenhanced ultra-high performance liquid chromatography/ion mobility/quadrupole time-of-flight mass spectrometry approach in combination with intelligent peak annotation workflows was established aimed to rapidly characterize the multicomponents from S.miltiorrhiza.Due to the sufficient optimization,satisfactory chromatography separation was enabled on an HSS T3 column within 33 min using 0.1%formic acid in water(A)and acetonitrile(B)as the mobile phase,while the data-independent HDMS^(E) in both the negative and positive electrospray ionization modes was utilized for the high-coverage MS^(2) data acquisition.Streamlined automatic peak annotation by searching an in-house library(recording 198 known compounds)followed by the subsequent confirming steps(e.g.,comparison with the reference compounds,fragmentation pathways analysis,and retention behavior comparison,etc.),allowed us to identify or tentatively characterize a total of 86 components(including 50 terpenoids,21 phenolic acids,and 15 others)from S.miltiorrhiza.Importantly,three-dimensional structure information,such as the retention time,MS^(1) and MS^(2) data,and collision cross section(CCS),was provided,which can facilitate the more reliable characterization of herbal components.

关键词： Ultra-high perform liquid chromatography/ion mobility/quadrupole time-of-flight mass spectrometry highdefinition MS^(E) automatic peak annotation Salvia miltiorrhiza phenolic acid tanshinone

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MYB Transcription Factors as Regulators of Phenylpropanoid Metabolism in Plants

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Molecular Plant 2015年第5期8卷 689-708页

作者： Jingying Liu Anne Osbourm Pengda Ma College of Life Sciences Northwest A&F University Yangling 712100 China Department of Metabolic Biology John Innes Centre Norwich NR4 7UH UK

Phenylpropanoid-derived compounds represent a diverse family of secondary metabolites that originate from phenylalanine. These compounds have roles in plant growth and development, and in defense against biotic and abiotic stress. Many of these compounds are also beneficial to human health and welfare. V-myb myeloblastosis viral oncogene homolog （MYB） proteins belong to a large family of transcription factors and are key regulators of the synthesis of phenylpropanoid-derived compounds. This review summarizes the current understanding of MYB proteins and their roles in the regulation of phenylpropanoid metabolism in plants.

关键词： MYB monolignol flavonoid phenolic acid stilbene

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Nutritional composition and antioxidant activity of twenty mung bean cultivars in China

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The Crop Journal 2016年第5期4卷 398-406页

作者： Zhenxing Shi Yang Yao Yingying Zhu Guixing Ren Institute of Crop Science Chinese Academy of Agricultural Sciences Animal Science Unit Gembloux Agro-Bio Tech University of Liège

Interest in mung bean(Vigna radiata L.) as a functional food is growing; however, studies on the nutritional composition of major mung bean cultivars planted in China are limited.Twenty Chinese mung bean cultivars were collected and their nutritional compositions including starch, fat, protein, and phytochemicals were analyzed. The cultivars were found to have a high amount of resistant starch, accounting for 16.1%–22.3% of total starch, and balanced amino acid constitutions. Palmitic acid and linoleic acid were the two dominant fatty acids, accounting for respectively 32.4% and 36.1% of all of the assayed fatty acids. Four bound phenolic acids(syringic, caffeic, p-coumaric, and ferulic acids) and two free phenolic acids(caffeic and ferulic acids) were identified by HPLC. The antioxidant activity of 70%ethanol extracts from the 20 mung bean cultivars was evaluated. Their DPPH and ABTS+free-radical-scavenging capacity ranged from 28.13 ± 2.24 to 35.68 ± 0.71 μmol g-1and from3.82 ± 0.25 to 13.44 ± 1.76 μmol g-1, respectively. Significant positive correlations of ABTS+free-radical-scavenging capacity with total phenolic acids and total flavonoid contents were observed. These results suggest that Chinese mung bean cultivars are rich in balanced nutrients and that their phytochemicals should be considered as potential sources of natural antioxidants.

关键词： Antioxidant phenolic acid Amino acid Flavonoid

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A High-Performance Liquid Chromatography Method for the Simultaneous Determination of Five Index Components in Danhong Injection

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American Journal of Analytical Chemistry 2023年第11期14卷 481-492页

作者： Yun An Tian Tian Qinglin Wang Xingchu Gong Chenchen Zhang Heze Medical College Heze China College of Pharmaceutical Engineering of Traditional Chinese Medicine Tianjin University of Traditional Chinese Medicine Tianjin China Innovation Institute for Artificial Intelligence in Medicine Zhejiang University Hangzhou China Pharmaceutical Informatics Institute College of Pharmaceutical Sciences Zhejiang University Hangzhou China Shandong Danhong Pharmaceutical Co. Ltd. Heze China

The purpose of this study was to establish a high-performance liquid chromatography (HPLC) method for the simultaneous determination of sodium danshensu, protocatechuic aldehyde, rosmarinic acid, salvianolic acid B, and 4-coumaric acid in Danhong injection. The chromatographic method employed was as follows: the column was a Welch Ultimate XB-C18 column (250 mm × 4.6 mm, 10 μm), the mobile phase was a gradient elution of 0.4% formic acid aqueous solution (A) and acetonitrile (B), the detection wavelengths were 280 nm for sodium danshensu, protocatechuic aldehyde, and salvianolic acid B and 326 nm for 4-coumaric acid and rosmarinic acid, the sample volume was 10 μL, the flow rate was 1.0 mL/min, and the column temperature was 35°C. This method can realize the separation and determination of sodium danshensu, protocatechuic aldehyde, rosmarinic acid, salvianolic acid B, and 4-coumaric acid within 50 minutes. The linear relationships of the five peak areas and their concentrations are good (R2> 0.9997). The precision RSD values are all less than 1.0%. The reproducibility RSD values are all less than 1.3%. The stability RSD values are all less than 2.2%. The recovery values ranged from 92.4% to 99.4%. This method is simple, accurate, and reproducible. It can be used for the determination of sodium danshensu, protocatechuic aldehyde, rosmarinic acid, salvianolic acid B, and 4-coumaric acid in Danhong injection.

关键词： Danhong Injection High Performance Liquid Chromatography phenolic acid Flavonoids

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Induced Effects of Exogenous phenolic acids on Allelopathy of a Wild Rice Accession(Oryza longistaminata,S37)

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Rice science 2010年第2期17卷 135-140页

作者： Xu Gao-feng ZHANG Fu-dou LI Tian-lin Wu Di ZHANG Yu-hua Agricultural Environment ＆ Resource Research Institute Yunnan Academy of Agricultural Sciences Kunming 650205 China

Four exogenous phenolic acids, including salicylic acid, fumalic acid, p-coumaric acid and p-hydroxybenzonic acid, were used to investigate the regulatory effects on allelopathy of a wild rice accession of S37 （Oryza Iongistaminata）, which is a known allelopathic rice. The four exogenous phenolic acids induced the enhancement of the allelopathic potential of wild rice S37 in target weeds though the weed-suppressive activities were low, and the inducible effects were dependent on the specific phenolic acid, concentration and treatment time. After foliar application of exogenous phenolic acids, the inhibition rates for plant height, root length and fresh weight of barnyard grass （Echinochioa crus-galli） were significantly higher than those of the control. Especially at the concentration of 100 mg/L, the inhibition rates for plant height and fresh weight of barnyard grass by fumalic acid were 38.12% and 26.31% higher than those of the control, showing that fumalic acid was more effective compared with other phenolic acids in inhibiting monocotyledon weed growth. Furthermore, the weedsuppressive activity of aqueous extract from the leaves of wild rice S37 treated with exogenous phenolic acids was increased, and it peaked at 48 h after the treatment with the aqueous extract, and then gradually declined.

关键词： salicylic acid fumalic acid p-coumaric acid p-hydroxybenzoic acid phenolic acid allelopathy inducible effect Oryza Iongistaminata

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bHLH transcription factor SmbHLH92 negatively regulates biosynthesis of phenolic acids and tanshinones in Salvia miltiorrhiza

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Chinese Herbal Medicines 2020年第3期12卷 237-246页

作者： Jian-hong Zhang Hai-zhou Lv Wan-jing Liu Ai-jia Ji Xin Zhang Jing-yuan Song Hong-mei Luo Shi-lin Chen Engineering Research Center of Chinese Medicine Resource Ministry of EducationInstitute of Medicinal Plant DevelopmentChinese Academy of Medical Sciences&Peking Union Medical CollegeBeijing 100193China School of Pharmaceutical Sciences Guangzhou University of Chinese MedicineGuangzhou 510006China Institute of Chinese Materia Medica China Academy of Chinese Medical SciencesBeijing 100700China

Objective:Salvia miltiorrhiza is a valuable herbal medicine with tanshinone and phenolic acid as the main biological active ingredients.The biosynthetic regulation of these bioactive compounds is controlled by a set of transcription factors(TFs).The basic helix-loop-helix(bHLH)transcription factor plays an important role in various physiological and biochemical processes in plants.However,research on bHLH TFs regulating phenolic acid or tanshinone biosynthesis in S.miltiorrhiza is limited.Methods:qRT-PCR was used for gene expression analysis.The subcellular localization of SmbHLH92 was detected by SmbHLHg2-GFP transient transformation into tobacco leaves,and its fluorescence was observed using a confocal laser scanning microscope.The transcriptional activity of SmbHLH92 was confirmed in the AH109 yeast strain.RNA interference hairy roots of SmbHLH92-RNAi transgenic lines were obtained through Agrobacterium-mediated genetic transformation.Ultra performance liquid chromatography(UPLC)was used to detect the changes of phenolic acids and tanshinones.Results:SmbHLH92 is a bHLH transcription factor that is highly expressed in the root and phloem of S.miltiorrhiza.The subcellular localization and transcriptional activity of SmbHLH92 indicated that SmbHLH92 was located in the nucleus and may be a transcription factor.RNA interference(RNAi)of SmbHLH92 in hairy roots of S.miltiorrhiza significantly increased the accumulation of phenolic acid and tanshinone.Quantitative RT-PCR(RT-qPCR)analysis showed the transcription level of genes encoding the key enzymes involved in the phenolic acid and tanshinone biosynthetic pathways was increased in the hairy roots of the SmbHLH92-RNAi transgenic line,comparing with the control line.Conclusion:These data indicate that SmbHLH92 is a negative regulator involved in the regulation of phenolic acid and tanshinone biosynthesis in S.miltiorrhiza.

关键词： phenolic acid Salvia miltiorrhiza bunge SmbHLH92 tanshinone transcription factor

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