PHYTOCHEMISTRY
·
2022
·
IF 4.004
Xiu-Qing Song,Lin-Lin Tian,Tao Ye,Hu Liu,Hua Zhang
Eleven undescribed glycosylated C 21 steroids and nine known homologous glycosides with diverse acyl substituents, as well as their common steroid aglycone , have been obtained from the roots of Marsdenia tenacissima. Their structures were elucidated mainly by comprehensive spectroscopic analyses and comparison with previously reported analogues, with the absolute configuration assignment being supported by chemical degradation , X-ray crystallography and ECD exciton chirality method. Among them, two pairs of regioisomers were found to exist as inseparable equilibrium mixtures due to an interesting intramolecular transesterification , and nicotinoyl substitution was first reported for metabolites from the title plant. Screening of these compounds in a panel of bioassays revealed that two glycosides displayed mild inhibition against butyrylcholinesterase .
研究领域:
植物化学
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天然产物化学
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产品关联
DOI
PubMed
高影响因子
PHYTOCHEMISTRY
·
2020
·
IF 3.044
Cai-Ping Yao,Jing Li,Jian-Feng Liu,Zhen-Xing Zou,Feng-Hua Kang,Xiao-Min Li,Dai Li,Kang-Ping Xu,Ping-Sheng Xu,Gui-Shan Tan
Seven undescribed C 27 steroidal glycosides , Seladelicatulasine A–G, including six cholestanol glycosides and one spirostanol glycoside, were isolated from Selaginella delicatula. Their structures were elucidated by 1D/2D NMR spectra and HRESIMS analyses. The absolute configurations of the sugars were determined by enzymatic hydrolysis and GC/MS analyses. These cholestanol glycosides were isolated from the family Selaginellaceae for the first time. Seladelicatulasine F is characterized as a rare B-5,6-secosteroid. In addition, all the compounds were evaluated for their inhibitory activities against cholinesterase (AChE/BChE) and monoamine oxidase (MAO-A/MAO-B). These steroidal glycosides displayed selective inhibition activities on cholinesterase. Seladelicatulasine A, B and E inhibited the AChE activity with IC 50 values of 0.31, 0.09, and 0.04 μ M, respectively. Seladelicatulasine A and F showed the strongest inhibition activity on BChE with IC 50 values of 0.37 and 0.65 μ M, respectively.
研究领域:
药用植物学
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天然产物化学
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生物化学
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神经药理学
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产品关联
DOI
PubMed
高影响因子
Natural Product Communications
·
2024
·
IF 1.5
Yan Lei,Bing Wang,Guanglin Zhu,Guo Feng,Wei Li,Caiyao Han,Qian Qin,Xie-an Yu,Xueli Song,Zhengyan He,Ju Zhang,Hongmei Su,Wenjing Wang
Background: In the research of the pharmacological activity of modern Chinese medicine, a large number of traditional Chinese medicines show anti-inflammatory activity. Asparagi radix is one of the anti-inflammatory drugs. With the deepening of people's research on Asparagi radix, its anti-inflammatory pharmacological effects have been gradually explored, but its specific anti-inflammatory active ingredients are still unclear. Therefore, it is necessary to screen and identify its specific anti-inflammatory active ingredients from Asparagi radix. At present, COX-2 is an important target for the treatment of chronic inflammation, and many drugs targeting this target have been marketed. However, some drugs have serious side effects, so it is very meaningful to study new COX-2 inhibitors. Methods: In this experiment, the fractions of different time periods are separated by high performance liquid chromatography-separation-trapping system (HPLC-CAD-FC). Then, ultra-high performance liquid chromatography-quadrupole time-of-flight/mass spectrometry (UPLC-Q-TOF/MS) and biological activity analysis techniques are used to identify the chemical composition and in vitro anti-inflammatory activity of each fraction. Finally, the data is integrated to screen out the substances with potential anti-inflammatory activity in Asparagi radix. Results: The results showed that the method established in this experiment can successfully isolate the active components of Asparagi radix, and four saponins with potential anti-inflammatory activity are identified. Conclusion: In summary, the analysis method established in this study can quickly and effectively screen out its anti-inflammatory active substances, and its potential anti-inflammatory active ingredients are mainly steroidal saponins.
研究领域:
中药学
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药理学
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产品关联
DOI
高影响因子
MOLECULES
·
2022
·Vol. 28
·期 1
·295
·
IF 4.927
Mengyu Li,Hui Luo,Zhen Huang,Jin Qi,Boyang Yu
Erdong Gao (EDG), consisting equally of roots of Asparagi Radix and Ophiopogonis Radix, is a well-known traditional Chinese formulation that has been used to treat cough and throat pain for centuries. However, the bioactive components in EDG remain to be elucidated. In this study, a rapid and effective method involving live cell bio-specific extraction and HPLC-Q-TOF-MS/MS was established to rapidly screen and identify the anti-inflammatory compounds of an EDG extract. One hundred and twenty-four components were identified in EDG extract using HPLC-Q-TOF-MS/MS analysis. After co-incubation with 16HBE, HPAEpiCs and HUVECs, which have been validated as the key target cells for pulmonary diseases, sixteen components were demonstrated to exhibit an affinity for binding to them. Furthermore, fifteen components were subsequently verified to exert anti-inflammatory effects on lipopolysaccharide (LPS)-induced 16HBE, HPAEpiCs and HUVECs via inhibiting the release of TNF-α and IL-6, indicating that nine steroidal saponins may possess potential for the treatment of lung-related diseases. Taken together, our study provides evidence that live cell biospecific extraction combined with the HPLC-Q-TOF-MS/MS technique was an efficient method for rapid screening potential bioactive components in traditional Chinese medicines and the structure activity relationship of steroidal saponins in EDG was summarized for the first time.Keywords:Erdong Gao;anti-inflammatory;steroidal saponins;structure activity relationship;cell extraction
研究领域:
药理学
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中药学
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分析化学
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细胞生物学
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产品关联
DOI
PubMed
高影响因子
WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY
·
2025
·Vol. 41
·期 5
·1-10
·
IF 4.2
Bi Yingjing,Han Yun,Bi Yanlan,Zhang Linshang,Sun Shangde
Sterol esters are naturally present in the by-product of edible oil processing, which is generally converted to sterols through saponification. Steroid intermediates play a crucial role in the production of pharmaceuticals, and these intermediates are predominantly synthesized via fermentation of sterol. This research explored the direct conversion of sterol esters into steroid intermediates using Mycobacterium sp. as a fermentation agent. The results demonstrated the successful identification of four steroid intermediates: androstenedione, 1,4-androstadienedione, 22-hydroxy-23,24-bisnorchol-4-ene-3-one, and 22-hydroxy-23,24-bisnorchol-1,4-dien-3-one, their individual intermediate concentrations were as follows: 144.2, 176.2, 30.8, 53.6 mg/L, with a total yield of 404.8 mg/L and a conversion rate of 29.5%. The optimized fermentation conditions included soybean oil at 3%, an initial pH of 7.0, a nitrogen source of 4.5 g/L, and hydroxypropyl-β-cyclodextrin of 15.0 g/L. Proteomic analysis revealed that sterol esters conversion pathway mirrors that of sterol, with an additional hydrolysis process. This work significantly expands our understanding of steroid intermediates production and offers valuable insights for the bioproduction industry. Graphical
研究领域:
生物化学
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制药工程
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微生物学
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2020
·Vol. 21
·期 5
·1665
·
IF 4.556
Shijun Wang,Xiaorong Yuan,Hao Qian,Na Li,Junru Wang
Background: Increasingly, different heterocyclic systems have been introduced into the steroid nucleus to significantly enhance the antitumor activities of steroid molecules. However, in this study, few literature precedents describing the pyrazine heterocyclic-condensed modification to an A-ring of steroid monomers were found, although the pyrazine group is thought to be essential for the potent anticancer activity of clinically relevant drugs and natural steroid dimers. Methods and Results: Two series of novel A-ring fused steroidal pyrazines were designed and efficiently synthesized from commercially available progesterone via key α-ketoenol intermediates. Through a cell counting kit-8 cytotoxic assay of 36 derivatives for three tumor cells, 14 compounds displayed significant antiproliferative activity compared to 5-fluorouracil, especially for human prostatic tumor cells (PC-3) in vitro. Further mechanistic studies indicated that the most active compound,12n(IC50, 0.93 μM; SI, 28.71), could induce the cell apoptosis of PC-3 cells in a dose-dependent manner and cause cell cycle arrest in the G2/M phase. The molecular docking study suggested that compound12nfitted the active sites of cytochrome P450 17A1 (6CIZ) well. Conclusions:12nmight serve as a promising lead compound for the development of novel anticancer drugs. This facile ring-closing strategy may provide a novel and promising avenue for the cycloaddition reaction of the steroidal skeleton throughα-ketoenol intermediates.Keywords:synthesis;fused steroids;pyrazines;anticancer activity;mechanism;docking
研究领域:
药物化学
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肿瘤学
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药理学
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产品关联
DOI
PubMed
高影响因子
MOLECULAR AND CELLULAR BIOCHEMISTRY
·
2015
·Vol. 411
·期 1
·161-171
·
IF 2.393
Peng Haibo,Wu Xia,Zhao Lifang,Feng Yifan
Abstract Through studying the changes of the total phospholipid components in mouse macrophages under the inflammatory status and the drug intervention status, we found the targets of non-steroidal anti-inflammatory drugs on phospholipids, thus providing the basis for the targets of in vitro anti-inflammatory effects of non-steroidal anti-inflammatory drugs. After RAW264.7 cells were pretreated with common non-steroidal anti-inflammatory drugs (aspirin and ibuprofen) and, respectively, stimulated with KLA for various periods (0.5, 4, 12, 16, and 24 h), the phospholipids were extracted. The dynamic changes of phospholipids in cells under various stimulations were analyzed with UPLC-Q-TOF–MS technique. Through the statistical analysis of Simca-P, we explored the potential targets of non-steroidal anti-inflammatory drugs on phospholipids. Through the dynamic analysis of phospholipids, we found two biomarkers (PC(17:1/18:1), PA(18:0/18:4)) which might be in vitro intervention inflammatory response targets of non-steroidal anti-inflammatory drugs. The analysis results show that in anti-inflammatory effects, non-steroidal anti-inflammatory drugs can inhibit COX, induce the cellular fatty acid desaturation and the changes of phospholipid components, stimulate free fatty acids, activate calcium ion channels of endoplasmic reticulum, and promote cell endocytosis, thus controlling inflammation and activating cells. Non-steroidal anti-inflammatory drugs can promote endocytosis, alter cell inflammatory response, and activate the process cells, thus realizing the anti-inflammatory effects. Graphical Abstract
研究领域:
药理学
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生物化学
·
炎症研究
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2022
·Vol. 27
·期 21
·7380
·
IF 4.927
Yaoyao Zhu,Liling Wang,Meixu Chen,Yifeng Zhou,Jun Huang
ZhejiangOphiopogonjaponicus(ZOJ) is a specific variety ofOphiopogon japonicuswith characteristic steroidal saponins and homoisoflavonoids, which are also main pharmacodynamic constituents with clinical effects, including curing inflammation and cardiovascular diseases. However, few analysis methods were applied to simultaneously and quantitatively determine two kinds of its constituents, and hazardous organic solvents are mostly used for extraction. In this study, a new validated simultaneous extraction and determination method for four characteristic steroidal saponins and homoisoflavonoids in ZOJ was established by ionic liquid–ultrasonic extraction (IL-UAE) combined with HPLC-DAD-ELSD analysis, which can be used for the quality control of ZOJ. Chromatographic separation was performed with a DAD wavelength at 296 nm, and the ELSD parameters of the drift tube temperature (DTT), atomizer temperature (AT), and nitrogen gas pressure (NGP) were set at 20% heating power, 70 °C, and 25 psi, respectively. The optimal IL-UAE conditions were 1 mol/L [Bmim]CF3SO3aqueous solution, a liquid–material ratio of 40 mL/g, and an ultrasonic time of 60 min. The proposed method is reliable, reproducible, and accurate, which were verified with real sample assays. Consequently, this work will be helpful for the quality control of ZOJ. It can also present a promising reference for the simultaneous extraction and determination of different kinds of constituents in other medicinal plants.Keywords:ionic liquid (IL);ZhejiangOphiopogonjaponicus(ZOJ);steroidal saponins;homoisoflavonoids;HPLC-DAD-ELSD
研究领域:
药用植物学
·
分析化学
·
药用植物
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产品关联
DOI
PubMed
高影响因子
Journal of Cleaner Production
·
2023
·
IF 11.1
Yakun Wang,Ziwei Song,Liwen Zhang,Deming Dong,Zhuojuan Li,Heyang Sun,Liting Wang,Zhiyong Guo
In surface waters at middle and high latitudes during winter, the coexistence of ice and water is a natural phenomenon. Nonsteroidal anti-inflammatory drugs (NSAIDs) as emerging contaminants have been found frequently in aquatic environments, including waters that are seasonally covered in ice. However, little is available for the environmental behaviors and fate of NSAIDs in ice, particularly in the system where ice and water coexist. In this study, the distribution and photodegradation of model NSAIDs naproxen (NPX), diclofenac (DCF), and acetaminophen (APAP) in an ice-water system were investigated. The findings demonstrated a 66.7%, 60.5%, and 66.7% increase in the ice-water distribution coefficient K iw of NPX, DCF, and APAP with initial concentrations of 10 ng L −1 relative to 500 ng L −1 . The K iw values were in decreased order of DCF, NPX, and APAP. The photodegradation rate constants of NPX, DCF, and APAP in ice increased by 27.0%, 35.6%, and 56.6% relative to those in water. With the increase in freezing time, the contribution ratios of distribution to the mass loss of NPX, DCF, and APAP increased by 19.9%, 21.1%, and 16.1%, respectively. The ratios of photodegradation to the mass loss of NPX, DCF, and APAP decreased by 5.0%, 5.7%, and 0.9%, respectively. An ice cover as the predominant factor could affect the distribution and photodegradation of drugs in the surface water. This study can close a knowledge gap regarding the transport and transformation of NSAIDs in the ice-water system and provide fresh insights into the behaviors and fate of emerging contaminants in seasonally ice-covered waters.
研究领域:
环境科学
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药物化学
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产品关联
DOI
高影响因子
ACS Sustainable Chemistry & Engineering
·
2023
·
IF 8.4
De Bai,Jiahong Huang,Yiyang Bo,Mi Wang,Wen Yu,Zhenyuan Wang,Chengyu Wu,Jiaheng Zhang
In this study, we synthesized a supramolecular antibacterial ionic salt, [PHMB][Sal], based on poly(hexamethylene biguanide) hydrochloride (PHMB) and sodium salicylate (SS) to endow plastic membranes with antibacterial function. The antibacterial composites of polyelectrolyte-nonsteroidal ionic salt can be blended with polymer materials, such as polybutylene adipate terephthalate (PBAT), because the melting point of the salt can be coordinated with that of the polymer material. The properties of the prepared membranes containing polyelectrolyte-nonsteroidal ionic salts did not change significantly. The mechanical properties and antimicrobial activities of the prepared hydrophobic membranes were investigated. When 3% of [PHMB][Sal] was added, the antimicrobial activities against Gram-positive Staphylococcus aureus and Escherichia coli were 4.12 and 4.30, respectively, and the antibacterial rate was as high as 99.9%, exhibiting extremely excellent antimicrobial properties. Biodegradable [PHMB][Sal] membrane materials are expected to be used in medical environments as well as on packaging surfaces in logistics, which can effectively prevent bacterial cross-infection.
研究领域:
材料科学
·
生物医学工程
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产品关联
DOI
高影响因子
FITOTERAPIA
·
2021
·
IF 2.882
Meng-Ling Zhao,Shu-Jun Shan,Rong Tao,Le-Tian Cui,Qiu-Rong Li,Jun Luo,Yi Li
Vernoramyosides A-F ( 1 – 6 ), six new Δ 7,9(11) stigmastane-type steroid saponins , along with four known analogues ( 7 – 10 ) were isolated from the leaves of Vernonia amygdalina Delile (Compositae). Their structures were determined by the combination of NMR, ECD and HR-ESI-MS data. These compounds all possessed highly oxidized side chain and a γ-lactam or α , β -unsaturated five-membered lactone ring. All isolates were screened for their activities in reversing resistance in MCF/DOX cells.
研究领域:
植物化学
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药物化学
·
天然产物研究
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DOI
高影响因子
Phytochemistry Letters
·
2020
·
IF 1.459
Fang-Fang Chen,Jing Zhou,Yu-Wei Zhang,Ya-Ping Chen,Yin-Ru Wang,Yun-Fang Zhao,Wei Liu,Xue-Feng Huang
Two novel cholestane-type steroidal saponins , melongoside R-S ( 1 - 2 ) and three novel furostanol-type steroidal saponins , melongoside T-V ( 3 - 5 ), together with three known steroidal saponins ( 6 - 8 ) were isolated from the seeds of Solanum melongna L. The structures of these compounds were elucidated by extensive spectroscopic analysis such as HR-ESI-MS, ESI-MS and NMR.
研究领域:
植物化学
·
天然产物研究
·
药物化学
✓ 已验证
DOI
高影响因子
危险品化学品经营许可证（带存储）