Research progress on chemical constituents in Sophora alopecuroides L.and their pharmacological activities

Sophora alopecuroides L.,a perennial plant belonging to Leguminosae family,is used as medicinal materials to treat a variety of skin diseases.Its chemical components are complex and diverse,mainly including alkaloids and flavonoids.Modern pharmacological studies have found that the isolated compounds from S.alopecuroides have a variety of pharmacological activities.In particular,alkaloids represented by matrine,aloperine and oxymatrine have significant anti-inflammatory,anti-viral,anti-tumor,anti-bacterial and immunomodulatory activities.This paper summarized the chemical constituents and pharmacological activities of S.alopecuroides,aiming to provide the basis for further research.

Sophaloseedlines A-G: Diverse Matrine-Based Alkaloids from Sophora alopecuroides with Potential Anti-Hepatitis B Virus Activities

Sophaloseedlines A-G(1-7),seven new matrine-based alkaloids along with two known analogues,were isolated from the seeds of Sophora alopecuroides.The new structures were determined based on extensive spectroscopic data,electronic circular dichroism calculations,and X-ray crystallography.Notably,sophaloseedline A(1)represents a novel rearranged 6(5→17)-abeo-matrine alkaloid featuring unprecedented highly constructed 7/6/5/6 tetracyclic fused ring skeleton.The hypothetical biosynthetic pathways for sophaloseedli nes A-F were proposed based on co-existing precursors.Additionally,all the isolated alkaloids were screened for their antiviral activities against hepatitis B virus,and new alkaloids 1 and 2 displayed more potent activities than those of matrine(a parent alkaloid of title plant)and positive control(lamivudine).

Structurally Diverse Matrine-Based Alkaloids with Anti-inflam-matory Effects from Sophora alopecuroides

A phytochemical investigation on the seeds of Sophora alopecuroides led to obtaining fourteen structurally diverse matrine-based alkaloids(1-14),including eight new ones(1,6,8-12,14).Notably,alopecuroide F(1)represents the first dimeric matrine-type skeleton assembled via unprecedent C-13-C-12'connection.The new structures were determined through extensive spectroscopic data(UV,OR,HRESIMS,1D,and 2D NMR),ECD calculations,and three instances,verified by X-ray crystallography.Biologically,all alkaloids were evaluated for cytotoxicity against four human cancer cell lines(HepG2,A549,THP-1,and MCF-7)and anti-inflammatory activities for two pro-inflammatory cytokines(TNF-αand IL-6).Alopecuroide F(1)can inhibit TNF-αand IL-6 productions in a dose-dependent manner with IC50 values of 35.6±0.5 and 41.7±0.8μmol/L,respectively.

Simultaneous Determination of Multiple Bioactive Constituents in Total Alkaloid of Sophora alopecuroides by HPLC-DAD

Objective To develop a qualitative and quantitative simultaneous determination of multiple bioactive constituents in total alkaloid in Sophora alopecuroides(TASA).Methods In the experiment,a new and simple HPLC-DAD method for the simultaneous determination of multiple constituents in TASA was developed.The separation was performed on a Kromasil C18 column(250 mm×4.6 mm,5.0μm)eluted with 0.02 mol/L potassium dihydrogen phosphate(adjusted pH 4.3 using 1%glacial acetic acid)and acetonitrile(75:25)at a flow-rate of 0.7 mL/min.The detection wavelength was set at 210 nm.Results Five constituents(sophoridine,matrine,oxymatrine,aloperine,and lehmannine)were simultaneously analyzed in this study.Four of them were identified and determinated by the developed method.The calibration curves exhibited linear regressions(r 2 >0.9995).The injection precision,the intra-day precision,and the analysis repeatability were validated with the RSD values less than 5.0%.The mean recoveries of the four constituents were ranged from 98.62%to 100.20%,and the RSD values were all less than 3.37%.Conclusion This method is convenient,fast,accurate,and is applicable to analyze the multi-constituents in TASA.

Total alkaloids of Sophora alopecuroides-and matrine-induced reactive oxygen species impair biofilm formation of Staphylococcus epidermidis and increase bacterial susceptibility to ciprofloxacin

Objective:To investigate the mechanism by which total alkaloids of Sophora alopecuroides(TASA)and matrine(MT)impair biofilm to increase the susceptibility of Staphylococcus epidermidis(S.epidermidis)to ciprofloxacin.Methods:The minimum biofilm inhibitory concentration(mBIC)was determined using a 2-fold dilution method.Structure of biofilm of S.epidermidis was examined by Confocal Laser Scanning Microscope(CLSM).The cellular reactive oxygen species(ROS)was determined using a DCFH-DA assay.The key factors related to the regulation of ROS were accessed using respective kits.Results:TASA and MT were more beneficial to impair biofilm of S.epidermidis than ciprofloxacin(CIP)(P<0.05).TASA and MT were not easily developed resistance to biofilm-producing S.epidermidis.The mBIC of CIP decreased by 2-6-fold following the treatment of sub-biofilm inhibitory concentration(sub-BIC)TASA and MT,whereas the mBIC of CIP increased by 2-fold following a treatment of sub-BIC CIP from the first to sixth generations.TASA and MT can improve the production of ROS in biofilmproducing S.epidermidis.The ROS content was decreased 23%-33%following the treatment of submBIC CIP,whereas ROS content increased 7%-24%following treatment with TASA+CIP and MT+CIP combination from the first to sixth generations.Nitric oxide(NO)as a ROS,which was consistent with the previously confirmed relationship between ROS and drug resistance.Related regulatory factorssuperoxide dismutase(SOD)and glutathione peroxidase(GSH)could synergistically maintain the redox balance in vivo.Conclusion:TASA and MT enhanced reactive oxygen species to restore the susceptibility of S.epidermidis to ciprofloxacin.

Alopecuroidines A-C, three matrine-derived alkaloids from the seeds of Sophora alopecuroides

Three matrine-derived alkaloids, alopecuroidine A(1), alopecuroidine B(2 a) and alopecuroidine C(2 b)were isolated from the seeds of Sophora alopecuroides. Their structures were elucidated by extensive spectroscopic analyses and X-ray diffraction. Three compounds possess an unprecedented rearranged fused7/6/5/6 tetracyclic skeleton with a diazacycloheptane structure. Their plausible biosynthetic pathway was also proposed. The anti-proliferative activities of compounds 1 and 2 a were examined by the MTT assay.Compound 1 inhibited the viability of human lung cancer A549 cells, having a half maximal inhibitory concentration(IC50) of 7.58 ± 2.47 μmol/L at 72 h. The flow cytometric analysis suggested that 1 inhibited A549 cell growth by inducing apoptosis and cell-cycle arrest. Additionally, 1 induced the loss of mitochondrial membrane potential, elevated intracellular reactive oxygen species, increased the Bax/Bcl-2 ratio, stimulated cleaved-caspase-3 and P53 protein levels, and suppressed the pro-caspase-3 level. Thus,1 appeared to induce A549 cells apoptosis through a mitochondria-mediated apoptotic pathway.

Three quinolizidine dimers from the seeds of Sophora alopecuroides and their hepatoprotective activities

Sophoralines A–C,three novel[2+2]cycloaddition dimers of matrine-based alkaloids with an unprecedented 6/6/6/6/4/6/6/6/6 nonacyclic skeleton containing 11 stereogenic centers,were isolated from Sophora alopecuroides.Their structures were determined by spectroscopic methods,and the absolute configurations were further determined by single-crystal X-ray diffraction analysis for 1 and quantum chemical calculations of electronic circular dichroism(ECD)spectra for 2 and 3.Moreover,1 exhibited excellent hepatoprotective activities in acetaminophen-induced liver injury in vitro and in vivo.

苦豆子绿肥的腐解和养分释放研究

以营养期至初花期苦豆子(Sophora alopecuroides)为试验材料,用尼龙袋法研究苦豆子绿肥在土壤中的腐解规律和C、N、P、K养分的释放规律。结果表明,经过118 d的腐解,绿肥中N、P矿化率逐步增加,C矿化率为66.59%;K在0~7 d矿化迅速,矿化率为55.46%,至118 d共矿化79.06%。C/N在0~14 d呈下降趋势,14~118 d逐渐平稳,养分矿化率表现为K>C>P>N。在118 d苦豆子绿肥干物质(DM)腐解量达65.2%,C、N、P、K矿化率分别达62.75%、44.93%、52.54%和79.06%,其中,0~14 d为快速分解阶段、14~28 d为减慢分解阶段、28~118 d为缓慢分解阶段。苦豆子绿肥的干物质降解与养分释放基本同步,且呈正相关。