CHEMISTRY & BIODIVERSITY
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2022
·Vol. 19
·期 11
·e202200414
·
IF 2.745
Xin-Yu Lei,Shao-Huan Liu,Ya-Xian Zhao,Meng-Jia Guo,Ling Tao,Xiang-Chun Shen,Nen-Ling Zhang
A pair of new lignan conformers ( 1 – 2 ), one new flavonoid glycoside ( 3 ), as well as nineteen known compounds were purified from the twigs and leaves of Cajanus cajan (L.) Millsp.. The planar structures of the unknown compounds were determined via NMR and high-resolution mass spectrometry, while their absolute configurations were elucidated via comparison between their experimental and calculated electronic circular dichroism (ECD) values. All the isolated compounds were assayed for their α -glucosidase inhibitory activities. The results demonstrated that compounds 8 – 12 , 15 – 16 , 18 – 19 , 21 – 22 had strong inhibition activities, with compound 10 (IC 50 =0.4±0.21 μM) most active. The structure-activity relationships were preliminarily summarized. Enzyme kinetics showed that compounds 8 , 9 , 15 – 16 , 18 – 19 , 21 – 22 were non-competitive inhibitors and compounds 10 – 12 were anti-competitive ones. Graphical
研究领域:
植物化学
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药理学
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天然产物研究
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DOI
PubMed
高影响因子
NATURAL PRODUCT RESEARCH
·
2020
·
IF 2.158
Yu-Xi Wang,Bin Lin,Le Zhou,Zhi-Yang Yan,Han Zhang,Xiao-Xiao Huang,Shao-Jiang Song
The phytochemical investigation on the twigs and leaves of Archidendron clypearia (Jack) I.C.N. led to the isolation of three pairs of furolactone-type lignans enantiomers, including a pair of new compounds (1R,5S,6S)-Kachiranol (1a) and (1S,5R,6R)-Kachiranol (1b) and four known compounds (2a/2b and 3a/3b). Separation of the furolactone-type lignans enantiomeric mixtures was achieved using chiral HPLC for the first time. Their structures were determined by spectroscopic analysis and comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. All optical pure compounds were evaluated for their inhibitory effects on β-amyloid aggregation by ThT assay. Among them, the inhibitory activity of the compound 1b (71.1%) was higher than the positive control (61.0%) and other compounds. In addition, molecular dynamics and molecular docking were employed to explore the binding relationship between the ligand and the receptor.
研究领域:
植物化学
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神经科学
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药物化学
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DOI
PubMed
高影响因子
JOURNAL OF ETHNOPHARMACOLOGY
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2025
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IF 5.4
Dongju Lin,Guangyao Li,Haoran Deng,Shuo Wang
Ethnopharmacological relevance Dictamnine (DIC) is the predominant pharmacological and hepatotoxic component of Cortex Dictamni (CD). CYP3A-mediated metabolic activation plays an important role in DIC-induced hepatotoxicity. Schisandra lignans (SCLs) are the major hepatoprotective ingredients of Schisandra chinensis (SC). CD and SC are frequently used as herb pairs in traditional Chinese medical formulas particularly for the treatment of eczema and urticarial. Our preliminary studies have shown that SC can protect against CD-induced liver injury. However, the underlying protective mechanism of SC against CD-induced liver injury has remained unknown. Aim of the study : This study aims to investigate the effects of SCLs on the hepatotoxicity and metabolic activation of DIC and elucidate the underlying hepatoprotective mechanism from the perspective of the inhibition of CYP3A-mediated metabolic activation. Material and methods The protective effect of SCLs against DIC-induced hepatotoxicity was evaluated by biochemical analysis and liver histological observation. The effect of SCLs on the in vitro metabolic activation of DIC was assessed by detecting the level of DIC-N-acetylcysteine (NAC) conjugates in mouse liver microsomal incubations. The effect of SCLs on the metabolic activation in vivo of DIC was examined by monitoring the toxicokinetic behaviors of DIC, DIC-induced hepatic GSH depletion, the cumulative urine excretion of DIC, the levels of DIC-NAC conjugates in urine and liver of mice, and the formation of DIC-derived cysteine-protein adducts. Results Our findings indicated that SCLs protected against DIC-induced hepatotoxicity in a dose-dependent manner. SCLs exhibited dose-dependent inhibitory effect on the formation of DIC-NAC conjugates in liver microsomal incubations, indicating SCLs inhibited the metabolic activation of DIC in vitro . SCLs increased C max and AUC s of DIC in the blood and liver of mice, leading to the enhancive accumulation of DIC in the circulation. Pretreatment with SCLs relieved hepatic GSH depletion induced by DIC, promoted the urinary excretion of DIC, inhibited the formation of reactive metabolite of DIC in urine and liver of mice, and reduced the production of DIC-derived cysteine-protein adducts, suggesting that SCLs influenced absorption, distribution, metabolism, and excretion (ADME) of DIC by suppressing the metabolic activation of DIC in vivo . Conclusions The study demonstrated the protective effect of SCLs against hepatotoxicity induced by DIC was related to the inhibition of CYP3A-mediated metabolic activation of DIC. Therefore, the study demonstrated that SCLs may serve as the candidate drugs for the intoxication of DIC. Moreover, our findings may interpret the protective mechanism of SC against CD-induced liver injury.
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PubMed
高影响因子
BIOORGANIC CHEMISTRY
·
2018
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IF 3.929
Yu-Xi Wang,Le Zhou,Jie Wang,Bin Lin,Xiao-Bo Wang,Xiao-Xiao Huang,Shao-Jiang Song
To develop potential agents for slowing the progression of Alzheimer′s disease, two pairs of new enantiomeric lignans, including a couple of rarely 8′,9′-dinor-3′,7-epoxy-8,4′-oxyneolignanes named (7 S , 8 S )- and (7 R , 8 R )-pithecellobiumin A ( 1a / 1b ) and a pair of 2′,9′-epoxy-arylnaphthalenes named (7 R , 8 R , 8′ R )- and (7 S , 8 S , 8′ S )-pithecellobiumin B ( 2a / 2b ) were separated by chiral high performance liquid chromatography (HPLC). Their planar structures were elucidated by spectroscopic data analyses. The absolute configurations were determined by comparing of experimental and calculated electronic circular dichroism (ECD). The inhibitory activity on A β aggregation of all optical pure compounds was tested by ThT assay. Interestingly, enantiomeric inhibitors 1a (62.1%) and 1b (81.6%) exhibited different degrees of anti-A β aggregation activity. However, 2a (65.4%) and 2b (68.4%) showed similar inhibition rate. The different inhibition profiles were explained by molecular dynamics and docking simulation studies.
研究领域:
植物化学
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神经退行性疾病研究
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药物化学
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DOI
PubMed
高影响因子
JOURNAL OF FOOD COMPOSITION AND ANALYSIS
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2019
·
IF 2.994
Yan Liu,Zhenzhen Xia,Liyun Yao,Yang Wu,Yan Li,Shan Zeng,Hao Li
Near-infrared spectroscopy (NIRS) combined with chemometric methods were used to discriminate the sesame oils from different Chinese provinces and determinate the lignans (sesamin and sesamolin) in these sesame oils. The geographic discriminant model was constructed by principal component analysis (PCA) combining with linear discriminant analysis (LDA), and the quantitative analysis models of lignans were built using partial least squares (PLS) regression. Multiplicative scatter correction (MSC) and competitive adaptive reweighted sampling (CARS) were adopted to optimize the regression models. It was found that the discriminant model could recognize the sesame oils from different Chinese provinces correctly, and the contents of sesamin and sesamolin calculated from the optimized models and high-performance liquid chromatography (HPLC) analysis are rather close. Reasonable results proved the feasibility of near-infrared spectroscopy (NIRS) combined with chemometric methods for geographic origin of sesame oils and quantitate analysis of lignans in sesame oils.
研究领域:
食品科学
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分析化学
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高影响因子
JOURNAL OF ETHNOPHARMACOLOGY
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2019
·
IF 3.414
Shicheng Fan,Conghui Liu,Yiming Jiang,Yue Gao,Yixin Chen,Kaili Fu,Xinpeng Yao,Min Huang,Huichang Bi
Ethnopharmacological relevance Cholestasis is a clinical syndrome caused by toxic bile acid retention that will lead to serious liver diseases. Ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) are the only two FDA-approved drugs for its treatment. Thus, there is a clear need to develop new therapeutic approaches for cholestasis. Here, anti-cholestasis effects of the lignans from a traditional Chinese herbal medicine, Schisandra sphenanthera , were investigated as well as the involved mechanisms. Materials and methods Adult male C57BL/6J mice were randomly divided into 9 groups including the control group, LCA group, LCA with specific lignan treatment of Schisandrin A (SinA), Schisandrin B (SinB), Schisandrin C (SinC), Schisandrol A (SolA), Schisandrol B (SolB), Schisantherin A (StnA) and Schisantherin B (StnB), respectively. Mice were treated with each drug (qd) for 7 days, while the administration of lithocholic acid (LCA) (bid) was launched from the 4th day. Twelve hours after the last LCA injection, mice were sacrificed and samples were collected. Serum biochemical measurement and histological analysis were conducted. Metabolomics analysis of serum, liver, intestine and feces were performed to study the metabolic profile of bile acids. RT-qPCR and Western blot analysis were conducted to determine the hepatic expression of genes and proteins related to bile acid homeostasis. Dual-luciferase reporter gene assay was performed to investigate the transactivation effect of lignans on human pregnane X receptor (hPXR). RT-qPCR analysis was used to detect induction effects of lignans on hPXR-targeted genes in HepG2 cells. Results Lignans including SinA, SinB, SinC, SolA, SolB, StnA, StnB were found to significantly protect against LCA-induced intrahepatic cholestasis , as evidenced by significant decrease in liver necrosis , serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), and alkaline phosphatase (ALP) activity. More importantly, serum total bile acids (TBA) and total bilirubin (Tbili) were also significantly reduced. Metabolomics analysis revealed these lignans accelerated the metabolism of bile acids and increased the bile acid efflux from liver into the intestine or feces. Gene analysis revealed these lignans induced the hepatic expressions of PXR-target genes such as Cyp3a11 and Ugt1a1 . Luciferase reporter gene assays illustrated that these bioactive lignans can activate hPXR. Additionally, they can all upregulate hPXR-regulate genes such as CYP3A4 , UGT1A1 and OATP2 . Conclusion These results clearly demonstrated the lignans from Schisandra sphenanthera exert hepatoprotective effects against LCA-induced cholestasis by activation of PXR. These lignans may provide an effective approach for the prevention and treatment of cholestatic liver injury.
研究领域:
药理学
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肝病学
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分子生物学
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民族药理学
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DOI
PubMed
高影响因子
CHEMISTRY AND PHYSICS OF LIPIDS
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2019
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IF 2.536
Yuan Gao,Shimin Wu,Renhuai Cong,Junyong Xiao,Fangli Ma
Schisandra chinensis is a medicinal and edible plant that contains various bioactive compounds. Among these, lignans are the major functional compounds. Nevertheless, detailed information about lignans in Schisandra chinensis oil remains scarce. A powerful UPLC-Q/TOF-MS method was established for the rapid identification of the lignan constituents of Schisandra chinensis oils. The results showed that 21 lignans have been unambiguously identified, and four lignans have been tentatively identified in the Schisandra chinensis oils. In addition, semi-quantitative analysis indicated that the total lignan content in the Schisandra chinensis oils was distributed from 67.73 ± 0.06 to 87.61 ± 1.83 mg/g. Schisandrin and schisandrin B were the most abundant lignans in the Schisandra chinensis oils, their content ranging from 15.85 ± 0.09 to 20.57 ± 0.38 mg/g. Additionally, this study provided a systematic characterization of lignans in Schisandra chinensis oil and indicated that the oil might be used as lignan-related functional foods.
研究领域:
植物化学
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分析化学
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药理学
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PubMed
高影响因子
JOURNAL OF FOOD SCIENCE
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2023
·Vol. 88
·期 12
·5278-5290
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IF 3.9
Xin-Yue Yang,Dan-Dan Wu,Cong-Cong Zhuang,Chao-Mei Ma
Secoisolariciresinol diglucoside ( SDG ) and tracheloside ( TCL ) are the main lignan components of flaxseed cake and safflower seed cake, which are by-products of oil extraction. Both SDG and TCL are metabolized into mammalian lignan enterolactone ( EL ) with the involvement of intestinal bacteria. In this research, we evaluated the anti-osteoporosis effects of SDG and the in vivo metabolites EL and enterodiol ( ED ) prepared in our previous work, as well as the newly isolated chemical constituents from safflower seed, including TCL , the lactone ring opening product of TCL ( OTCL ) and two alkaloids on the alloxan-induced zebrafish model. All the compounds showed significant anti-osteoporosis effects at 80 µM, with p < 0.05 for EL and p < 0.001 for other compounds compared with the model. SDG and TCL showed the most significant and concentration-dependent effects, with p < 0.001 compared with model at 20 µM. The alkaloids, N -coumaroylserotonin glucoside and N -feruloylserotonin glucoside, also showed anti-osteoporosis at 20 µM with p < 0.01, whereas EL , ED , and OTCL showed no significant effects. Quantitative real-time polymerase chain reaction revealed that SDG and TCL upregulated the expression of osteogenic genes Runx2, SP7, OPG, Col1a1a, Alp, ON, OPN , and OCN in alloxan-treated zebrafish. The in vivo metabolite of lignans, EL , showed significant anti-inflammatory effect ( p < 0.01) at 20 µM, which might also help to combat osteoporosis and other complications caused by excessive immune response in the body. The results provided scientific data for using the oil extraction by-products as sources of anti-osteoporosis compounds. Practical Application This study found that lignans in flaxseed cake and safflower seed cake exhibited anti-osteoporosis effects by upregulating the expression of osteogenic genes, making the oil extraction by-products sources of anti-osteoporosis compounds.
研究领域:
营养学
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药理学
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分子生物学
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PubMed
高影响因子
Food Science and Human Wellness
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2023
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IF 7
Zhenhua Liu,Mengke Wang,Lijun Meng,Yixiao Chen,Qiuyi Wang,Yan Zhang,Xuefeng Xi,Wenyi Kang
Patrinia scabiosaefolia , is used as wild vegetable in China for more than 2 000 years, with a variety of pharmacological activities, including anti-inflammatory, anti-tumor and hypoglycemic. Based on our ongoing research on chemical constituents and hypoglycemic activity of P. scabiosaefolia , 4 lignan compounds, (+)-isolariciresinol ( 1 ), 7 R ,7' R ,8 S ,8' S -(+)-neo-olivil-4- O - β - D -glucopyranoside ( 2 ), 4- O- methylcedrusin ( 3 ) and patrinian A ( 4 ), were isolated and identified. The hypoglycemic activity showed that compounds 2 and 3 could extremely significantly improve insulin resistance at 100 ( P < 0.001), 50 ( P < 0.001) and 25 µmol/L ( P < 0.01) in IR 3T3-L1 cells. While compound 4 only promoted glucose uptake by IR 3T3-L1 cells at 100 µmol/L ( P < 0.01). Western blotting experiments showed that compounds 2 and 4 up-regulated the protein expressions of p-IRS, PI-3K, p-AKT and glucose transporter 4 (GLUT4), and promoted the transcription of GLUT4 mRNA. Therefore, the mechanisms of compounds 2 and 4 were presumed to improve IR by activating PI-3K/AKT signaling pathway.
研究领域:
药理学
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分子生物学
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内分泌学
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高影响因子
PHYTOMEDICINE
·
2024
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IF 6.7
Jinyu Wang,Aijuan Zheng,Fei Lin,Xiaozhuo Zhang,Kaifang Shi,Tingxu Yan,Ying Jia
Background Schisandra chinensis lignan (SCL), a major active component of the traditional functional Chinese medicine Schisandra chinensis , has been reported to have antidepressant effects. Its mechanisms include alleviating intestinal barrier injury (IBI) by resolving intestinal microflora, anti-inflammation, and neuroprotection. SCL also regulates endogenous cannabinoid system, and it is closely related to the onset and development of depression. Purpose We investigated a new treatment strategy for depression, i.e., alleviating IBI by regulating the endogenous cannabinoid system for antidepressant effects, as well as conducted in-depth research to explore the specific mechanism. Methods Behavioral analysis was conducted to detect the occurrence of depressive-like behavior in C57BL/6 mice. We used hematoxylin-eosin staining, periodic acid-Schiff staining, and immunofluorescence to evaluate IBI. Network pharmacology and Western blotting (WB) were used to predict and confirm that the amelioration effect of SCL was associated with anti-inflammation and anti-apoptosis. Combined with the levels of anandamide (AEA) and 2-arachidonoylglycerol (2-AG), we conducted the Pearson analysis between the AEA, 2-AG levels and the major targets identified and validated by network pharmacology and WB. Subsequently, URB-597, a fatty acid amide hydrolase (FAAH) antagonist with an AEA hydrolase-inhibiting effect, was administered to the mice, and behavioral analysis and apoptotic proteins were verified. Plasma endocannabinoid levels after URB-597 supplementation were measured via 6470 Triple Quadrupole LC/MS. Finally, the cannabinoid receptor type 2 (CB2R) antagonist AM630 was administered to mice, and immunofluorescence and WB were performed to assess the proteins of IBI and anti-inflammation. Results The study demonstrated that SCL alleviated depressive-like behaviours and ameliorated IBI. Network pharmacology and WB confirmed that the improvement of IBI was related to the anti-inflammatory and anti-apoptotic pathways. Pearson results showed that AEA levels were positively correlated with inflammation and apoptosis, with a greater contribution to apoptosis. In-depth studies validated that the URB-597 administration reversed the positive effects of SCL on depressive-like behavior and anti-apoptosis. Similarly, URB-597 counteracted AEA levels reduced by SCL and decreased 2-AG levels. Furthermore, AM630 supplementation antagonized SCL's effect of improving IBI by reactivating the MAPK/NF-κB inflammation pathway. Conclusion Overall, SCL, in collaboration with the endogenous cannabinoid system regulated by SCL, alleviates depression associated IBI. The specific mechanism involes SCL decreasing AEA levels to inhibit colon tissue cell apoptosis by up-regulating FAAH. Simultaneously, it directly triggers CB2R to reduce inflammation responses, further alleviating IBI.
研究领域:
药理学
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神经科学
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免疫学
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分子生物学
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PubMed
高影响因子
Waste and Biomass Valorization
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2024
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IF 2.6
Zhao Zijia,Gao Yan,Yuan Min,Ye Cai,Guo Yingxue,Zhao Yanli,Li Jinlian,Cui Jiwen,Dong Tianwei,Wu Dongmei
A significant quantity of residues will produce when volatile oil in Schisandra chinensis fruit is extracted by steam distillation. It is important to investigate the residues for potential use. Currently, there is an increasing demand for anti-photoaging products due to the skin damage caused by UV radiation. In this paper, the ingredients of the residues were investigated, and the anti-photoaging activities of residues extracts were studied. The results showed that the residues still contained notable amounts of lignans, flavonoids, and organic acids. In the extracted fraction of dichloromethane (DE), the residues contained higher amounts of schizandrol B and schisantherin A compared to the fresh fruit. The levels were particularly high at 17.39 ± 0.02 and 52.58 ± 0.04 mg/ml, respectively. By lowering the amount of matrix metalloproteinase-1 (MMP-1), reactive oxygen species (ROS) accumulation, and type I collagen (COL-I) loss in fibroblasts, the residues showed targeted benefits in the fight against skin photoaging. In particular, the DE-R phase of residues was very successful in raising the level of COL-I, matching or even exceeding that of retinol (ROL) and undistilled fresh fruits. Protocatechuic acid, schizandrol A, schizandrol B, schisantherinA, schisandrin A and schizandrin B were found to have a significant correlation with the anti-photoaging ability of residues. Particularly, there was a strong and significant correlation between an increase in COL-I and schizandrol B (|ρ| = 0.829*) and schisantherin A (|ρ| = 0.928**), and the distillation procedure has the potential to increase the amount of schizandrol B and schisantherin A in the residues. Graphical
研究领域:
药理学
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化妆品科学
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植物学
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生物化学
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DOI
高影响因子
MICROCHEMICAL JOURNAL
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2024
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IF 4.9
Defeng Liu,Hongxiu Liu,Xiaomin Fu,Shujing Guo,Shengci Fan,Xinsheng Fang
Deep eutectic solvents (DESs) are showing broad application prospects in separation of bioactive components from natural products because of their eco-friendly advantages. In this study, a green method for effective extraction and reThe ultrasound-assisted extraction is optimized using Box-Behnken designcovery of three bioactive lignans from the leaves of Forsythia suspensa was developed for the first time using ultrasound-assisted deep eutectic solvents extraction (UAE-DES) and macroporous resin enrichment. Choline chloride-ethylene glycol (molar ratio of 1:3) with 20 % (v/v)water was confirmed as the optimal solvent. The optimized conditions were obtained by response surface methodology: liquid to solid ratio of 30 mL/g, extraction temperature of 30℃, ultrasound power of 200 W and extraction time of 30 min. The extraction yields of phillyrin, pinoresinol and phylligenin were 6.70, 9.65 and 45.77 mg/g, respectively, which were significantly higher than those of conventional organic solvents. Furthermore, the target compounds were recovered and purified from DES extracts using macroporous resin of HPD100. The recovery efficiency of phillyrin, pinoresinol and phylligenin was 87.9 %, 95.0 % and 91.7 %, respectively. After purification by the resin the content of phillyrin, pinoresinol and phylligenin in the recovered dry extract was 10.6 %, 12.8 %, and 64.8 %, respectively. This study provided an efficient and green approach for extraction and preparative separation of active lignans from natural products.
研究领域:
植物化学
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天然产物化学
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分离科学
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环境科学
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产品关联
DOI
高影响因子
危险品化学品经营许可证（带存储）