ANALYTICAL AND BIOANALYTICAL CHEMISTRY
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2023
·Vol. 415
·期 10
·1855-1863
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IF 4.3
Fang Xiaoting,Wang Jing,Chen Jiamin,Guo Hongyu,Yang Fafu
Although various fluorescent sensors for biomolecules had been extensively reported, the effective fluorescent sensor was seldom reported for detecting oleanolic acid up to now. This work reports the first color-change fluorescence sensor for oleanolic acid based on a bridging bis-cyanostilbene derivative with chiral camphanic groups ( C-BCS ). C-BCS possessed the chartreuse fluorescence in aqueous media, which transferred to strong blue fluorescence in the presence of oleanolic acid. This sensing ability of C-BCS for oleanolic acid exhibited the high selectivity among all kinds of biomolecules and ions. The good linearity between the fluorescence intensity and concentration of oleanolic acid was acquired in the range of 0.2 × 10 −6 to 8.0 × 10 −6 M with the detecting limitation of 0.0582 μM. The 1:1 binding process was clarified as oleanolic acid located in the opening cavity composed of two bridging cyanostilbene units and two chiral camphanic groups based on multiple hydrogen bonds and hydrophobic interaction. The detecting ability of C-BCS was applied on sensing oleanolic acid in thin-layer chromatography analysis, imprinting experiment, tap water, and tea samples, suggesting the effective on-site sensing abilities of C-BCS for oleanolic acid in real samples and daily life. Graphical Abstract
研究领域:
分析化学
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材料科学
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生物技术
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环境科学
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DOI
PubMed
高影响因子
JOURNAL OF NATURAL PRODUCTS
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2010
·
IF 3.159
Shan Qian,Haijiao Li,Yin Chen,Weiyu Zhang,Shengyong Yang,Yong Wu
Protein tyrosine phosphatase 1B (PTP1B) is a negative regulator in the process of insulin signaling and a promising drug target for diabetes and obesity. Derivatives of oleanolic acid were synthesized and evaluated as PTP1B inhibitors. Several derivatives exhibited moderate to good inhibitory activities against PTP1B, with 25f displaying the most promising inhibition (IC50 = 3.12 μM). Structure−activity relationship analyses of these derivatives demonstrated that the integrity of the A ring and 12-ene moieties was important in the retention of PTP1B enzyme inhibitory activities. In addition, hydrophilic and acidic groups as well as the distance between the oleanene and acid moieties were associated with PTP1B inhibitory activities. Possible binding modes of 25f were explored by molecular docking simulations.
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高影响因子
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
·
2021
·
IF 5.051
Hao He,Huifang Li,Toyosi Akanji,Shengli Niu,Zhujun Luo,Dongli Li,Navindra P. Seeram,Panpan Wu,Hang Ma
Oleanolic acid (OA) is a natural cosmeceutical compound with various skin beneficial activities including inhibitory effect on hyaluronidase but the anti-hyaluronidase activity and mechanisms of action of its synthetic analogues remain unclear. Herein, a series of OA derivatives were synthesised and evaluated for their inhibitory effects on hyaluronidase. Compared to OA, an induction of fluorinated (6c) and chlorinated (6g) indole moieties led to enhanced anti-hyaluronidase activity (IC50 = 80.3 vs. 9.97 and 9.57 µg/mL, respectively). Furthermore, spectroscopic and computational studies revealed that 6c and 6g can bind to hyaluronidase protein and alter its secondary structure leading to reduced enzyme activity. In addition, OA indole derivatives showed feasible skin permeability in a slightly acidic environment (pH = 6.5) and 6c exerted skin protective effect by reducing cellular reactive oxygen species in human skin keratinocytes. Findings from the current study support that OA indole derivatives are potential cosmeceuticals with anti-hyaluronidase activity.
研究领域:
化妆品科学
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药物化学
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生物化学
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DOI
PubMed
高影响因子
JOURNAL OF SEPARATION SCIENCE
·
2016
·Vol. 39
·期 8
·1592-1602
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IF 2.741
Zonggui Tang,Changbin Liu,Jing Wang,Hongmin Li,Yong Ji,Guohong Wang,Chunxia Lu
Monodisperse molecularly imprinted polymers for oleanolic acid were successfully prepared by a precipitation polymerization method using oleanolic acid as a template, methacrylic acid as a functional monomer, and divinylbenzene/ethylene glycol dimethacrylate as a crosslinker in a mixture of acetonitrile and ethanol (3:1, v/v). The imprinted polymers and nonimprinted polymers were characterized by using scanning electron microscopy, Fourier transform infrared spectroscopy, and thermogravimetric analysis. The resulting imprinted polymers had average diameters of 3.15 μm and monodispersity values of 1.024. The results clearly demonstrate that use of ethanol as a cosolvent is indeed exceedingly effective in promoting the dissolution of oleanolic acid and in obtaining uniform microspheres. Molecular recognition properties and binding capability to oleanolic acid were evaluated by adsorption testing, which indicated that the imprinted polymers displayed optimal binding performance with a maximum adsorption capacity of 17.3 mg/g and a binding saturation time of 80 min. Meanwhile, the produced imprinted polymers exhibited higher selectivity to oleanolic acid than that for ursolic acid and rhein. Herein, the studies can provide theoretical and experimental references for the oleanolic acid molecular imprinted system.
研究领域:
高分子科学
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分析化学
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分离科学
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药物化学
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材料科学
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DOI
高影响因子
MEDICINAL CHEMISTRY RESEARCH
·
2019
·Vol. 28
·期 8
·1212-1222
·
IF 1.72
Sheng Li-xin,Huang Jia-yan,Liu Chun-mei,Zhang Ju-zheng,Cheng Ke-guang
A total of 25 targeted hydrogen sulfide donor–pentacyclic triterpene hybrids were designed, synthesized and evaluated on the basis of inspiring reports about hydrogen sulfide donor molecules and oleanolic acid derivatives on anti-tumor activity. The results revealed that only some hybrids ( 10a , 10b , 12a , 12b , 13a , and 15b ) showed moderate anti-proliferation activity against K562 cell line. It indicated that oleanane-type, ( R )-lipoic acid and TBZ groups were much more favorable to the anti-proliferation activity. Furthermore, C-3 OH was more beneficial than C-28/29 COOH in the oleanane-type to the antitumor activity of the batch of ( R )-lipoic acid derivatives. And among them, only compound 13a exhibited moderate anti-proliferation activity against both K562 and K562/ADR cell lines, while it exhibited no anti-proliferation activity against BEL-7402 and L-O2 cell lines. Therefore, it suggested that it was not suitable for hybridization of hydrogen sulfide donors attached to oleanolic acid, ursolic acid and glycyrrhetinic acid in the field of anti-tumor.
研究领域:
药物化学
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肿瘤学
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分子生物学
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药理学
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天然产物化学
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DOI
高影响因子
Molecular Medicine Reports
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2017
·Vol. 16
·期 6
·8413-8419
·
IF 1.692
Qian An,Qian Hu,Bing Wang,Wenjun Cui,Fei Wu,Yu Ding
The overexpression of inflammasome components is correlated with diabetes‑associated complications. Oleanolic acid is a triterpenoid compound which is important in arterial injury. The present study evaluated whether oleanolic acid improved diabetic rat carotid artery injury through the inhibition of nucleotide‑binding domain, leucine‑rich‑containing family, pyrin domain‑containing‑3 (NLRP3) inflammasomes signaling pathways. A diabetic rat model was induced using streptozotocin (60 mg/kg) and underwent carotid artery injury. Morphometric analysis was performed using hematoxylin and eosin staining. The mRNA and protein levels were assayed by reverse transcription‑quantitative polymerase chain reaction and western blotting, respectively. It was found that oleanolic acid (100 mg/kg/day) improved body weight, glucose metabolic disorders, neointimal hyperplasia and endothelial dysfunction in diabetic rats with carotid artery injury. In addition, oleanolic acid administration significantly downregulated the mRNA and protein expression levels of endothelin 1 in diabetic rats. Oleanolic acid decreased the intimal area and the ratio of neointima to media in diabetic rats. Serum levels of tumor necrosis factor‑α, interleukin (IL)‑1β, IL‑6 and IL‑18 in the oleanolic acid‑treated diabetic rats were downregulated. Consistent with the serum results, it was demonstrated that oleanolic acid administration caused a significant decrease in the levels of NLRP3, caspase‑1 and IL‑1β in the carotid arteries of diabetic rats. Taken together, these observations suggested that oleanolic acid attenuated carotid artery injury in diabetic rats and the underlying mechanism was mediated, at least partially, through the suppression of NLRP3 inflammasome signaling pathways.
研究领域:
药理学
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心血管疾病
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糖尿病
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DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2020
·
IF 10.652
Yi Zhang,Jian Li,Zhen Wang,Ming-Ze Xu,Zhi Zeng,Jin-peng Huang,Yan-Qing Guan
Exogenous insulin administration is still the most used treatment for diabetes (mainly used for type-1 diabetes in clinic), however type 2 diabetes (T2D) with the characteristics of insulin resistance accounts for the vast majority proportion (90–95%) of diabetic population, which makes insulin function failure. Currently, many efforts have been devoted to insulin delivery with nanomedicine means, whereas the treatment of insulin resistance in T2D using nanotechnology strategy is rarely reported. In this study, we transformed a plant-derived natural insulin sensitizer into biocompatible nano-transport system, where the natural insulin sensitizer oleanolic acid (OA) was conjugated onto natural polymer polygalacturonic acid (PGA) to form self-assembled micelles as oral administrated nanomedcine for insulin resistance treatment in T2D. In vitro and in vivo investigation demonstrated that OA loaded PGA-OA micelles possess stability to cross the gastrointestinal barriers and improve drug intestinal absorption, remarkably maintaining plasma drug concentration for a longer time. Therefore, this formulation manifested good reversal effect on insulin resistance in the T2D rat model, and thereby exhibited long-term outcomes in glucose level control even after drug withdrawal. Additionally, the molecular mechanism of OA loaded PGA-OA mediated insulin-resistant reversal was found that it was probable mediated by promoting IRS-1/PI3K/AKT signaling pathway and inhibiting the activity of PTP1B enzyme simultaneously. In this regard, such a facile, safe and potent nanomedicine strategy may be promising alternative for long-acting insulin-resistant treatment in T2D therapy.
研究领域:
药剂学
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纳米技术
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糖尿病
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药物递送系统
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产品关联
DOI
高影响因子
International Journal of Nanomedicine
·
2013
·
IF 3.463
Kunchi Zhang,Shaowa Lv,Xiuyan Li,Yufei Feng,Xin Li,Lu Liu,Shuang Li,Yongji Li
Background The purpose of this work was to develop nanostructured lipid carriers (NLCs) loaded simultaneously with oleanolic acid and gentiopicrin.Methods An aqueous dispersion of NLCs was prepared successfully using a film-ultrasonic method, with glycerin monostearate as the solid lipid and oleic acid as the liquid lipid. Poloxamer 188 was used as the surfactant. A central composite design was used to optimize the technologic parameters. The characteristics of the NLCs were then investigated.Results The encapsulation efficiency was 48.34% ± 2.76%, drug loading was 8.06% ± 0.42%, particle size was 111.0 ± 1.56 nm, polydispersity index was 0.287 ± 0.01, and zeta potential was −23.8 ± 0.36 mV for the optimized NLCs. The other physicochemical properties were characterized by transmission electron microscopy and differential scanning calorimetry. Drug release followed first-order kinetics and release studies confirmed that oleanolic acid and gentiopicrin fitted a sustained-release model. Compared with NLCs loaded with oleanolic acid or gentiopicrin alone, NLCs loaded with both oleanolic acid and gentiopicrin produced drug concentrations which persisted for a significantly longer time in plasma, with a linear decrement following second-order kinetics. Aspartate and alanine aminotransferase levels were significantly lower on exposure to NLCs loaded with both oleanolic acid and gentiopicrin than in negative controls.Conclusion The results of this study confirm that oleanolic acid and gentiopicrin can be loaded simultaneously into NLCs. Compared with oleanolic acid and gentiopicrin loaded alone, sustained release and protective effects against hepatic injury were observed using NLCs loaded with both oleanolic acid and gentiopicrin.
研究领域:
药剂学
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生物医学工程
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肝病治疗
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DOI
PubMed
高影响因子
TALANTA
·
2023
·
IF 6.1
Ying Wang,Xiaodan Wu,Guansong Shao,Bowen Zhai,Zihan Wang,Bingyang Qin,Tao Wang,Zhiguo Liu,Yujie Fu
An oleanolic acid (OA) surface molecularly imprinted polymer silylated porous composite aerogels (OA-MIP@Si-PC-aerogels) adsorbent material was successfully prepared and characterized. The material not only has a great selectivity for the target molecule OA but also has other noteworthy qualities including high stability, excellent repeatability, and a sizable adsorption capacity. via cellulose and sodium alginate as the main materials, the carrier Si-PC-aerogels were made through ionic cross-linking, chemical cross-linking, and silylation procedures. By adopting a surface molecular imprinting approach on Si-PC-aerogels, OA-MIP@Si-PC-aerogels were effectively created utilizing OA as the template molecule and MAA as the functional monomer . Due to the presence of a specific imprinted layer on the aerogel surface, the adsorption capacity of OA-MIP@Si-PC-aerogels for OA could reach 66.20 mg g −1 . OA-MIP@Si-PC-aerogels could achieve a 68.86% yield of OA from the extracts of lingonberry (Vaccinium Vitis-Idaea L .). The adsorption capacity remained at 90% after five consecutive adsorption-desorption cycles. HepG2 cells were exposed to OA that was effectively enriched with OA-MIP@Si-PC-aerogels in lingonberry (Vaccinium Vitis-Idaea L .) fruit homogenates. This OA significantly inhibited the growth of HepG2 cells in vitro. It further demonstrated that OA-MIP@Si-PC-aerogels could efficiently target OA enrichment and separation with good recovery.
研究领域:
材料科学
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生物化学
·
药学
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PubMed
高影响因子
CHEMICO-BIOLOGICAL INTERACTIONS
·
2024
·
IF 4.7
Shaofei Song,Hong Peng,Yuan Li,Tingting Zhao,Renjie Cao,Lei Zheng,Min Huang,Yiming Jiang
Liver regeneration after liver tumor resection or liver transplantation is crucial, the remaining liver frequently fails to regenerate in some patients. Oleanolic acid (OA), a pentacyclic triterpenoid compound which has been shown to protect against various liver diseases. However, the effect of OA on liver regeneration after partial hepatectomy (PHx) is still unclear. In this study, the results showed that OA (50 mg/kg, twice daily) treatment induced liver mass restoration and increased the liver-to-body weight ratio of mice following PHx. Meanwhile, OA promoted hepatocyte proliferation and increased the number of BrdU-, Ki67-and PCNA-positive cells. Furthermore, OA increased the nuclear accumulation of PXR and induced the expression of PXR downstream proteins such as CYP3A11, UGT1A1 and GSTM2 in mice, as well as in AML12 and HepRG cells. Luciferase reporter assay and nuclear localization of PXR further demonstrated the effect of OA on PXR activation in vitro . Molecular docking simulation showed that OA could interact with the PXR active sites. Moreover, OA inhibited the expression of FOXO1, RBL2 and CDKN1B, and increased the expression of PCNA, CCND1 and CCNE1 in vivo and in vitro . Silencing of Pxr further confirmed that OA-mediated upregulation of proliferation-related proteins depended on PXR. The current study illustrated that OA exhibited a significant promoting effect on liver regeneration following PHx, potentially through regulation of the PXR signaling pathway to accelerate liver recovery.
研究领域:
药理学
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肝脏病学
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分子生物学
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DOI
PubMed
高影响因子
Food Bioscience
·
2025
·
IF 5.9
Kangkang Zhi,Yi Shi,Weibing Lin,Huilan Yang,Yawen Zhu,Jiajia Cui,Wen Zhang,Junlong Wang,Ji Zhang
The present study developed a natural nano-assembled delivery system with curcumin (Cur)-synergistic bioactivity using natural oleanolic acid (OA). The OA self-assembled nanoparticles (OA NPs) were systematically prepared via region-limited self-assembly, with their size (20–600 nm) regulated by varying key preparation parameters. The XPS, FTIR, CAT, and MD revealed that the 3-hydroxy oxygen and 17-carboxyl oxygen of OA act as hydrogen bond donor and acceptor, respectively, to form hydrogen bonds. Together with van der Waals forces, these interactions drive the formation of hydrophilic surface-exposed nanoparticles. The OA NPs exhibited good biocompatibility, demonstrated by favorable blood safety (hemolysis rate <5 %) and low cytotoxicity (cell viability >90 %). The Cur was efficiently encapsulated into OA NPs, achieving a LC of 22.81 % and EE of 68.43 %. The encapsulated Cur showed significantly improved physicochemical properties, with a 29.02-fold increase in water solubility, a 3.64-fold enhancement in photostability, and a 2.77-fold improvement in thermal stability compared to free Cur. In vivo , OA NPs exhibited intestinal retention time three times longer than gastric retention, and release studies confirmed their intestinal-selective and sustained-release behavior, which followed the Korsmeyer–Peppas model. The Cur-OA NPs demonstrated optimal antioxidant activity, showing 2.45-fold higher potency (based on EC 50 values) than free Cur, attributable to the synergistic effect between Cur and OA NPs. This study highlights the potential of Cur-OA NPs as an oral antioxidant formulation and offers a promising strategy for developing natural nanocarriers with curcumin-synergistic bioactivity.
研究领域:
纳米技术
·
药剂学
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天然产物化学
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抗氧化研究
·
药物递送
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产品关联
DOI
高影响因子
ACS Nano
·
2026
·
IF 17.3
Ya Wang,Yuan Wang,Yan Sun,Xianbin Sun,Yuanming Li,Haijun Chen,Yu Gao
Ferrocene derivatives possess a typical “sandwich” structure that facilitates the formation of two-dimensional nanosheets (2D NSs), while their ferrous ions can effectively mediate chemodynamic therapy (CDT). However, conventional bottom-up synthesis methods for nanosheets often involve complex processes and stringent preparation conditions, limiting their therapeutic applications. In this study, we developed a simple yet efficient premix-dropwise-stir synthetic strategy to fabricate ultrathin oleanolic acid/perfluorocarbon-ferrocene (O/F-Fc) 2D NSs with considerable antitumor properties. The incorporation of oleanolic acid (OA) effectively inhibited F-Fc self-aggregation and facilitated the formation of ultrathin nanosheets (∼1.5 nm), while simultaneously enhancing the CDT efficacy of F-Fc through synergistic effects. Comprehensive in vitro and in vivo studies demonstrated that these carrier-free 2D NSs possess multifunctional capabilities, including oxygen self-supply to alleviate tumor hypoxia, generation of multiple reactive oxygen/nitrogen species to amplify oxidative stress and enhance CDT, antifibrotic activity, promotion of macrophage M1 polarization to activate immune responses, and enhanced deep tumor penetration, collectively enabling effective tumor microenvironment (TME) remodeling. This study not only presents an approach for preparing ultrathin ferrocene-based carrier-free 2D NSs, but also offers mechanistic insights into developing carrier-free organic 2D nanosystems for synergistic TME remodeling and enhanced CDT efficacy in cancer therapy.
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高影响因子
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