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liquiritigenin promotes osteogenic differentiation and prevents bone loss via inducing auto-lysosomal degradation and inhibiting apoptosis

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Genes & Diseases 2023年第1期10卷 284-300页

作者： Yu Qiu Yueyang Zhao Zhimin Long Aijia Song Peng Huang Kejian Wang Ling Xu David Paul Molloy Guiqiong He College of Stomatology Chongqing Medical UniversityChongqing Key Laboratory of Oral Diseases and Biomedical SciencesChongqing Municipal Key Laboratory of Oral Biomedical Engineering of Higher EducationChongqing400016China Chongqing Key Laboratory of Neurobiology Chongqing Medical UniversityChongqing 400016China Department of Anatomy Chongqing Medical UniversityChongqing 400016China Laboratory of Medical Experiment Technology Institute of Life ScienceChongqing Medical UniversityChongqing 400016China Department of Biochemistry and Molecular Biology Chongqing Medical UniversityChongqing 400016China

Osteoporosis(OP)is a debilitating skeletal abnormality involving bone remodeling and bone cell homeostasis characterized by decreased bone strength and high fracture risk.A novel therapeutic intervention for OP by manipulating cellular autophagy-apoptosis processes to promote skeletal homeostasis is *** effects of the naturally occurring plant extract liquiritigenin(LG)were demonstrated in an ovariectomy(OvX)-OP mouse model and preosteoblast MC3T3-E1 ***-CT and histological staining assessments of skeletal phenotype were applied alongside detection of autophagy activity in osteocytes and MC3T3-E1 cells by transmission electron microscopy(TEM).The effects of LG on chloroquine(CQ)-and the apoptosis-inducing TS-treated osteogenic differentiations and status of lysosomes within MC3T3-E1 cells were analyzed by Neutral red,Alizarin red S and alkaline phosphatase(ALP)staining and Western blot *** with LG prevented bone loss,increased osteogenic differentiation in vivo and in vitro,and inhibited osteoclast formation to some *** analyses revealed that LG can improve auto-lysosomal degradation within osteocytes from OVX mice and MC3T3-E1 *** abnormal status of lysosomes associated with CQ and TS treatments was notably alleviated by LG which also reduced levels of apoptosis-induced inhibition of osteogenic differentiation and averted abnormal osteogenic differentiation as a consequence of a blockage in autolysosome ***,LG stimulates bone growth in Oovx mice through increased osteogenic differentiation and regulation of autophagyapoptosis mechanisms,presenting an auspicious natural therapy for Op.

关键词： Apoptosis Auto-lysosomal degradation liquiritigenin Osteogenic differentiation Osteoporosis

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Development of liquiritigenin-phospholipid complex with the enhanced oral bioavailability

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Chinese Journal of Natural Medicines 2020年第12期18卷 916-921页

作者： SHI Chang-Can QIN Kun-Ming XU Ke CHEN An CAI Ting CAI Bao-Chang School of Pharmacy Nanjing University of Chinese MedicineNanjing 210046China School of Pharmacy China Pharmaceutical UniversityNanjing 210009China Nanjing Haichang Chinese Medicine Group Corporation Nanjing 210061China

In the present study,liquiritigenin-phospholipid complex(LPC)was developed and evaluated to increase the oral bioavailability of liquiritigenin.A single-factor test methodology was applied to optimize the formulation and process for preparing *** effects of solvent,drug concentration,reaction time,temperature and drug-to-phospholipid ratio on encapsulation efficiency were *** were characterized by UV-visible spectroscopy,differential scanning calorimetry(DSC),fourier transform infrared spectroscopy(FTIR),and powder X-ray diffractometry(PXRD).The apparent solubility and n-octanol/water partition coefficient were *** pharmacokinetic characteristics and bioavailability of the LPC were investigated after oral administration in rats in comparison with liquiritigenin *** LPC was successfully *** optimum level of various parameters for liquiritigeninphospholipid complex was obtained at the drug concentration of 8 mg·mL-1,reaction time for 15 min,reaction temperature of 30℃,a ratio of 1∶4.5(W/W)drug-to-phospholipid and anhydrous ethanol as reaction *** to liquiritigenin,the AUC0-t of the LPC was increased by 239%.The liquiritigenin-phospholipid complex significantly increase the lipid solubility and bioavailability of liquiritigenin,suggesting that it is an effective formulation for further development and clinical applications.

关键词： liquiritigenin liquiritigenin-phospholipid complex Solubility Characterization Cioavailability

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Development of a monolithic polymer pipette for solid-phase extraction of liquiritigenin in rat plasma

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Chinese Chemical Letters 2012年第6期23卷 723-726页

作者： Hong Wu Zhang Kang Li Zhi Xian Liang Feng YangWang Qi Wen Lu School of Pharmacy Guangdong Pharmaceutical College Guangzhou 510006 China

A monolithic polymer column with mixed-mode interaction was prepared by in situ polymerization in a 1000μL pipette. Two kinds of monomers, butyl methacrylate （BMA） and 2-（dimethylamino）ethyl methacrylate （DMAM） were applied to constructing the mixed-mode interaction of monolithic polymer column. Its solid-phase extraction properties for liquiritigenin （LQG） were evaluated by high performance liquid chromatography （HPLC） with a gradient elution procedure. After the extraction procedure was optimized, the maximum binding capacity and extraction recovery following the optimal extraction procedure were investigated. Calibration curve was expressed as A = 65.9C ＋ 4.53 （r2 = 0.998） with a linear range of 0.151-1.80μg/mL. The experimental results indicate that the monolithic polymer pipette presents good extraction efficiency for LQG. It can be envisaged that the developed monolithic polymer pipette possesses the potential for its application to the enrichment of other flavonoids compounds being similar to the structure of LQG.

关键词： Monolithic polymer pipette Solid phase extraction High performance liquid chromatography liquiritigenin

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LC–MS/MS Method for Quantification of liquiritigenin in Rat Plasma: Application to Pharmacokinetic Study of Liquiritin

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Chinese Herbal Medicines 2016年第1期8卷 53-60页

作者： Shi-qi Dong Hui-rong Fan Quan-sheng Li Guang-li Wei Ya-zhuo Li Chang-xiao Liu Duan-yun Si School of Chemical Engineering and Technology Tianjin University State Key Laboratory of Drug Delivery Technology and Pharmacokinetics Tianjin Institute of Pharmaceutical Research

Objective A simple, sensitive, and rapid LC-MS/MS method has been established and validated for the determination of liquiritigenin （LG） in rat plasma. Methods Naringenin was chosen as internal standard （IS）. LG and IS were separated on a Diamonsil C18 analytical column with a mobile phase of methanol-10% methanol in water containing 0.5 mmol/L ammonium formate and 0.2% formic acid （55：45） at the isocratic flow rate of 0.6 mL/min for 10 min. The multiple reaction monitoring （MRM） was performed on a mass spectrometer in the negative ion mode with electro-spray ionization （ESI） source and the transition from precursor ion to product ion was m/z255.0~119.0 for LG and m/z 271.04151.0 for IS, respectively. Results The linearity was acceptable in the range of 5-5000 ng/mL （r= 0.9973）. The inter-day and intra-day accuracies were in the ranges of -0.09%-3.25% and -5.02%-9.21%, respectively. The precision was in the ranges of 3.60%-12.4% and 0.909%-6.89%, respectively. LG was stable in the course of anarysis and storage. Conclusion The LC-MS/MS method was successfully applied to the pharmacokinetic study for the first time in rats after ig and iv administration of liquiritin （LQ）, a glycoside of LG, at pharmacologically effective levels.

关键词： LC-MS/MS liquiritigenin liquiritin pharmacokinetics

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Development of a monolithic polymer pipette for solid-phase extraction of liquiritigenin in rat plasma

Development of a monolithic polymer pipette for solid-phase ...

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全国生物医药色谱及相关技术学术交流会（2012）

作者：张红武 School of Pharmacy Guangdong Pharmaceutical University

A monolithic polymer column with mixed-mode function was prepared by in situ polymerization in a 1000μL *** kinds of monomers,butyl methacrylate（BMA） and 2-（dimethylamino）ethyl methacrylate（DMAM）,were applied to constructing the mixed-mode function for the synthesized polymer *** solid-phase extraction properties for liquiritigenin（LQG） were evaluated by high performance liquid chromatography（HPLC） with a gradient elution *** extraction procedure was optimized in *** then,the maximum binding capacity and extraction recovery following the optimal extraction procedure were also *** curve was expressed as A=65.9C+4.53（r 2 =0.998） with a linear range of 0.151～1.80μg/*** limit of quantification（LOQ） was estimated as 0.015μg/ml and the limit of detection（LOD） as 0.0045μg/*** experimental results indicate that the monolithic polymer pipette presents good extraction efficiency for *** monolithic polymer envisages the potential for application to the enrichment of other flavonoids compounds being similar to the structure of LQG.

关键词： Monolithic polymer pipette Solid phase extraction High performance liquid chromatography liquiritigenin

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Adsorption and desorption of isoliquiritigenin and liquiritigenin to carbon nanotubes

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Journal of Chinese Pharmaceutical Sciences 2010年第6期19卷 443-450页

作者：赵海娇慕春海李超鹏韩博王新春陈文新疆特种植物药资源教育部重点实验室新疆石河子832000

The adsorption and desorption of isoliquiritigenin and liquiritigenin to different types of carbon nanotubes （CNTs） were comparatively studied in this study. The pore structure, specific surface area, surface morphologies and functional groups of the CNTs were tested by N2 adsorption, scanning electron microscope （SEM） and infrared spectra （IR）. The investigation of dynamic adsorption, isothermal equilibrium adsorption and desorption of isoliquiritigenin and liquiritigenin to CNTs demonstrated that the adsorption amount on oxidized multi-walled carbon nanotubes （o-MWCNTs） was greater than that on raw multi-walled carbon nanotubes （r-MWCNTs）, especially the adsorption of isoliquiritigenin to o-MWCNTs. The data of equilibrium adsorption were better represented by the Freundlich isotherm model. In addition, the adsorbed amount per unit CNTs was decreased when the temperature got higher. From the results of isothermal equilibrium adsorption and desorption to CNTs, it could be inferred that o-MWCNTs had higher adsorption to isoliquiritigenin and liquiritigenin than r-MWCNTs. Additionally, o-MWCNTs had a better desorption efficiency to isoliquiritigenin and liquiritigenin （about 48.57% and 32.86%） than r-MWCNTs （about 24.56% and 17.46%）.

关键词： Carbon nanotubes Isoliquiritigenin liquiritigenin Adsorption and desorption

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De novo biosynthesis of liquiritin in Saccharomyces cerevisiae

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Acta Pharmaceutica Sinica B 2020年第4期10卷 711-721页

作者： Yan Yin Yanpeng Li Dan Jiang Xianan Zhang Wei Gao Chunsheng Liu School of Chinese Pharmacy Beijing University of Chinese MedicineBeijing 102488China School of Traditional Chinese Medicine Capital Medical UniversityBeijing 100069China School of Pharmaceutical Sciences Advanced Innovation Center for Human Brain ProtectionCapital Medical UniversityBeijing 100069China Pharmacy Department Beijing Longfu HospitalBeijing 100010China

liquiritigenin(LG),isoliquiritigenin(Iso-LG),together with their respective glycoside derivatives liquiritin(LN)and isoliquiritin(Iso-LN),are the main active flavonoids of Glycyrrhiza uralensis,which is arguably the most widely used medicinal plant with enormous demand on the market,including Chinese medicine prescriptions,preparations,health care products and even *** studies have shown that these ingredients have broad medicinal value,including anti-cancer and antiinflammatory *** the biosynthetic pathway of glycyrrhizin,a triterpenoid component from ***,has been fully analyzed,little attention has been paid to the biosynthesis of the flavonoids of this *** obtain the enzyme-coding genes responsible for the biosynthesis of LN,analysis and screening were carried out by combining genome and comparative transcriptome database searches of *** and homologous genes of known flavonoid biosynthesis *** catalytic functions of candidate genes were determined by in vitro or in vivo *** work characterized the complete biosynthetic pathway of LN and achieved the de novo biosynthesis of liquiritin in Saccharomyces cerevisiae using endogenous yeast metabolites as precursors and cofactors for the first time,which provides a possibility for the economical and sustainable production and application of *** flavonoids through synthetic biology.

关键词： Glycyrrhiza uralensis Liquiritin Isoliquiritin liquiritigenin Isoliquiritigenin Heterologous synthesis Saccharomyces cerevisiae

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Combined treatment with valproic acid and estrogen has neuroprotective effects in ovariectomized mice with Alzheimer’s disease

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Neural Regeneration Research 2021年第10期16卷 2078-2085页

作者： Yan-Zhen Li Yuan-Jie Liu Wei Zhang Shi-Fang Luo Xin Zhou Gui-Qiong He Chongqing Key Laboratory of Neurobiology Chongqing Medical UniversityChongqingChina Department of Anatomy Chongqing Medical UniversityChongqingChina Department of Galactophore Chongqing University Cancer HospitalChongqingChina

Postmenopausal women with Alzheimer’s disease exhibit dramatically reduced sensitivity to estrogen replacement therapy,which is though to be related to an estrogen receptor(ER)α/ERβratio imbalance arising from a significantly decreased level of ERs of the *** aim of our study was to investigate whether valproic acid(VPA)can enhance the beneficial effects of estrogen on cognitive function through restoration of ERαand ERβexpression in the *** removed the ovaries of female APP/PS1 mice to simulate the low estrogen levels present in postmenopausal women and then administered VPA(30 mg/kg,intraperitoneal injection,once daily),17β-estradiol(E2)(2.4μg,intraperitoneal injection,once daily),liquiritigenin(LG)(50μg/kg,intragastric infusion,once daily),VPA+E2,or VPA+LG for 4 successive *** with treatment with a single drug,treatment with VPA+E2 or VPA+LG significantly increased the level of glycogen synthase kinase 3β,increased the expression of estrogen receptorα,reduced the expression of small ubiquitin-like modifiers,and increased the level of estrogen receptorβ.This resulted in enhanced sensitivity to estrogen therapy,reduced amyloidβaggregation,reduced abnormal phosphorylation of the tau protein,reduced neuronal loss,increased dendritic spine and postsynaptic density,and significantly alleviated memory loss and learning impairment in Alzheimer’s *** study was approved by the Chongqing Medical University Animal Protection and Ethics Committee,China on March 6,2013.

关键词： 17β-estradiol amyloidβ dementia estrogen receptorα estrogen receptorβ glycogen synthase kinase-3β liquiritigenin menopause neuron loss tau

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Cancer therapy using natural ligands that target estrogen receptor beta

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Chinese Journal of Natural Medicines 2015年第11期13卷 801-807页

作者： Gangadhara R Sareddy Ratna K.Vadlamudi Department of Obstetrics and Gynecology University of Texas Health Science Center at San Antonio Cancer Therapy & Research Center University of Texas Health Science Center at San Antonio

Estrogen receptor beta(ERβ) is one of the two key receptors(ERα, ERβ) that facilitate biological actions of 17β-estradiol(E2). ERβ is widely expressed in many tissues, and its expression is reduced or lost during progression of many tumors. ERβ facilitates estrogen signaling by both genomic(classical and non-classical) and extra-nuclear signaling. Emerging evidence suggests that ERβ functions as a tissue-specific tumor suppressor with anti-proliferative actions. Recent studies have identified a number of naturally available selective ERβ agonists. Targeting ERβ using its naturally available ligands is an attractive approach for treating and preventing cancers. This review presents the beneficial actions of ERβ signaling and clinical utility of several natural ERβ ligands as potential cancer therapy.

关键词： Estrogen receptor Estrogen receptor beta Tumor suppressor ER beta agonists liquiritigenin S-equol Genistein

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HPLC–MS and HPLC–MS/MS analysis of seven active constituents of Xiao-Xu-Ming decoction and application to a pharmacokinetic study after oral administration to rat

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Acta Pharmaceutica Sinica B 2012年第2期2卷 188-197页

作者： Yilin Wang Chunguang Ding Caisheng Wu Kehe Du Jinlan Zhangn Hailin Qin Jinfeng Hou Guanhua Du State Key Laboratory of Bioactive Substances and Functions of Natural Medicines Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

Xiao-xu-ming decoction(XXMD)is a traditional Chinese medicine that has been widely used to treat theoplegia and its *** paper reports the development of three separate assays based on reversed phase high-performance liquid chromatography–mass spectrometry(HPLC–MS)and HPLC–MS/MS for the determination of seven active constituents of XXMD viz oroxylin A-7-O-glucuronide,wogonoside,liquiritigenin,cimifugin,5-O-methylvisammiol,glycyrrhizic acid and glycyrrhetinic acid in rat *** calibration curves were linear(r >0.99)with lower limits of quantitation(LLOQs)<12.4 ng/***-and inter-day precisions(as relative standard deviation)were all <10.7% with recoveries in the range of 88.7–113%.In addition,the seven analytes were shown to be stable in rat plasma samples under relevant storage *** validated methods were successfully applied to a pharmacokinetic study in rat after oral administration of XXMD.

关键词： Xiao-Xu-Ming decoction HPLC-MS HPLC-MS/MS Pharmacokinetics Oroxylin A-7-O-glucuronide Wogonoside liquiritigenin Cimifugin 5-O-methylvisammiol Glycyrrhizic acid Glycyrrhetinic acid

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