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Diosgenin
Molecular Catalysis · 2024 · IF 3.9

Strong Lewis acid MOF material for efficient and clean diosgenin extraction from total saponins in D. zingiberensis C. H. Wright

XiaoNing Gao,YanXiao Zhang,Wei Fu,Hong Zhou,Lu Feng

Conventional hydrolysis of total saponins for the extraction of diosgenin, an essential ingredient in the production of steroid hormones, has caused significant ecological pollution, making efficient and clean extraction methods necessary. Here, UiO-66-NH 2 with defect sites containing Zr-coordinated hydroxide and water groups was synthesized using concentrated HCl as a crystal modulator, which was further treated with trimethylsilyl trifluoromethanesulfonate (Me 3 SiOTf) to afford UiO-66-NH 2 OTf using the oxygen affinity of the Me 3 Si group. The strong Lewis acid UiO-66-NH 2 OTf was used to extract diosgenin from the total saponin, and the extraction temperature, extraction time and amount of addition were optimized using single-factor experiments and the response surface method. In addition, high-resolution mass spectrometry has been used to analyze the resulting compounds, thus suggesting an alcoholysis pathway and an alcoholysis mechanism for the total saponins.

研究领域: 药用植物化学 · 环境科学 · 药物化学
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Food Biophysics · 2020 ·Vol. 15 ·期 4 ·452-462 · IF 2.387

Structure and Properties of Organogels Developed by Diosgenin in Canola Oil

Zeng Chaoxi,Wan Zheng,Xia Huiping,Zhao Haiyang,Guo Shiyin

In this study, naturally occurring ingredient diosgenin was utilized as an organogelator for structuring canola oil. Results show that stable diosgenin-based organogel can be obtained at only 2% of diosgenin concentration when the gel preparation temperature is 100 °C. Oil binding capacity and rheological properties of the organogel were investigated. Results demonstrate that these two macroscopic characteristics of the organogels can be significantly modified by simply changing the gel preparation temperature or diosgenin concentration. When the preparation temperature was 120 °C and the diosgenin concentration higher than 4%, oil binding capacity of at least 90% were obtained. Furthermore, higher gel preparation temperature resulted in higher G′values of the diosgenin-based organogels. According to the results analyzed by polarized light microscopy, XRD and FT-IR, it can be found that the possible gelation mechanism of the diosgenin-based organogels is formation of supramolecular structures by self-assembly of diosgenin molecule crystals via hydrogen bonding interaction. Varying gel preparation conditions of the organogels lead to self-assembly of diosgenin molecules to form different microstructures. Therefore, diosgenin can be considered as a good organogelator for producing functional organogel from canola oil. The novel diosgenin-based organogel is expected to be widely used in bio-related fields such as food and pharmaceutical industries.

研究领域: 食品科学 · 材料科学
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IRISH JOURNAL OF MEDICAL SCIENCE · 2015 ·Vol. 185 ·期 3 ·581-587 · IF 0.827

Diosgenin prevents bone loss on retinoic acid-induced osteoporosis in rats

Zhao S.,Niu F.,Xu C.-Y.,Liu Y.,Ye L.,Bi G.-B.,Chen L.,Tian G.,Nie T.-H.

Objective To observe the preventive and therapeutic effects of diosgenin on retinoic acid-induced osteoporosis in rats. Methods A total 50 Sprague-Dawley rats were randomly divided into 5 groups: control group, model group (osteoporosis rats), low (10 mg kg −1 ), middle (30 mg kg −1 ), and high-dose diosgenin (90 mg kg −1 )-treated groups. The osteoporosis rats model was induced by retinoic acid. The BMD and physical parameters of femoral including length, wet weight, and dry weight in each group were measured. The hematoxylin–eosin staining was used for bone histomorphology analysis. Besides, the bone calcium (Ca) and phosphorus (P) contents were measured. In order to detect the biochemical index in different treatment groups, the serum tartrate-resistant acid phosphatase (TRAP), alkaline phosphatase (ALP), estradiol, and osteocalcin were compared among different groups. Results The osteoporosis rat model was successfully induced by retinoic acid. Compared with the model group, the lessening of femoral length and weight and the loss of BMD were significantly improved in diosgenin groups. Both contents of Ca and P were much more increased when induced by retinoic acid ( p  < 0.05). The estradiol and osteocalcin levels in the middle and high-dose treatment groups were significantly higher than that of the model group, while the ALP and TRAP levels were much lower than the model group ( p  < 0.05). Conclusion Diosgenin can prevent the loss of bone in experimental rats. The mechanism may be that it improves the level of estrogenic hormone of estradiol and inhibits the high bone turnover.

研究领域: 药理学 · 内分泌学 · 骨科 · 动物模型研究
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JOURNAL OF APPLIED POLYMER SCIENCE · 2021 ·Vol. 139 ·期 6 ·51596 · IF 3.125

Polymer-based solid acid catalyst for the green production of diosgenin

Hui Yuan,Xuejun Yu,Wenxiu Jiang,Bowei Shen,Farong Zhang,Zhiquan Pan,Hong Zhou

In this study, a novel polymer-based solid acid catalyst was prepared by free radical polymerization of N, N′-methylenebisacrylamide (MBA) and allyl sodium sulfonate (SAS), followed by acidifying of diluted hydrochloric acid. The prepared solid acid was fully characterized by FTIR, solid-state 13 C-NMR, TGA, XPS, element analysis, and SEM. In addition, the prepared solid acid poly(MBA-SAA) was used as a catalyst to extract diosgenin from Dioscorea zingiberensis C.H.Wright (DZW) under solvethermal condition using ethanol as a solvent. And the optimal conditions of temperature (104.02°C), alcoholysis time (5.87 h) and solid acid dosage (0.39 g), were obtained by response surface analysis based on the results of single factor experiments. The yield of diosgenin (14.53%) obtained in the alcoholysis is higher than that of the traditional sulfuric acid hydrolysis method. The alcoholysis products were analyzed by high performance liquid chromatography-mass spectrometry (LC–MS) and UV–vis, respectively. The results showed that the solid acid with higher catalytic activity and good reusability can replace sulfuric acid to extract diosgenin, which has a great potential for the clean production of diosgenin in industry.

研究领域: 化学工程 · 植物化学 · 药物化学
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FREE RADICAL RESEARCH · 2014 · IF 2.989

Diosgenin inhibits superoxide generation in FMLP-activated mouse neutrophils via multiple pathways

Y. Lin,R. Jia,Y. Liu,Y. Gao,X. Zeng,J. Kou,B. Yu

Diosgenin possesses anti-inflammatory and anticancer properties. Activated neutrophils produce high concentrations of the superoxide anion which is involved in the pathophysiology of inflammation-related diseases and cancer. In the present study, the inhibitory effect and possible mechanisms of diosgenin on superoxide generation were investigated in mouse bone marrow neutrophils. Diosgenin potently and concentration-dependently inhibited the extracellular and intracellular superoxide anion generation in Formyl-Met-Leu-Phe (FMLP)- activated neutrophils, with IC50 values of 0.50 ± 0.08 μM and 0.66 ± 0.13 μM, respectively. Such inhibition was not mediated by scavenging the superoxide anion or by a cytotoxic effect. Diosgenin inhibited the phosphorylation of p47phox and membrane translocation of p47phox and p67phox, and thus blocking the assembly of nicotinamide adenine dinucleotide phosphate oxidase. Moreover, cellular cyclic adenosine monophosphate (cAMP) levels and protein kinase A (PKA) expression were also effectively increased by diosgenin. It attenuated FMLP-induced increase of phosphorylation of cytosolic phospholipase A (cPLA2), p21-activated kinase (PAK), Akt, p38 mitogen-activated protein kinase (p38MAPK), extracellular signal-regulated kinase (ERK1/2), and c-Jun N-terminal kinase (JNK). Our data indicate that diosgenin exhibits inhibitory effects on superoxide anion production through the blockade of cAMP, PKA, cPLA2, PAK, Akt and MAPKs signaling pathways. The results may explain the clinical implications of diosgenin in the treatment of inflammation-related disorders.

研究领域: 药理学 · 免疫学 · 细胞生物学 · 炎症 · 癌症研究
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CATALYSIS LETTERS · 2022 ·Vol. 152 ·期 11 ·3453-3464 · IF 2.936

Catalytic Alcoholysis to Prepare Diosgenin with a Solid Acid Based on Nano TiO2

Zhao Mengqi,Pan Zhiquan,Chen Qingrong,Zhou Hong

Diosgenin is an important intermediate of drugs, the special structure similar to hormone determines its important position in drug synthesis. Diosgenin was generally obtained by sulfuric acid hydrolysis of dioscorea, which produced too much acid wastewater, and caused environmental issues. A new solid acid based on TiO 2 was designed and synthesized through the sulfonation of the prepared TiO 2 , the structure was fully characterized by FTIR, SEM, EDX, XPS and XRD. Under the optimized conditions, the yield of diosgenin reached 30.75%, the value was much higher than that of H 2 SO 4 of the same quality. To explore the factors that affect the yield, the usage amount of the solid acid, the temperature, the solvent volume and the extraction time were taken into the analysis, and the results of the recycling experiments indicated that the prepared solid acid can be used for three time and maintain its high activity. A highly efficient solid acid catalyst for diosgenin extraction from saponins was successfully synthesized, and the extraction method was environmentally friendly. Graphical Abstract

研究领域: 药物化学 · 环境科学
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JOURNAL OF NANOPARTICLE RESEARCH · 2019 ·Vol. 21 ·期 12 ·1-11 · IF 2.009

Hydrolysis extraction of diosgenin from Dioscorea nipponica Makino by sulfonated magnetic solid composites

Zhang Farong,Shen Bowei,Jiang Wenxiu,Yuan Hui,Zhou Hong

Extraction of diosgenin from the rhizome of Dioscorea by catalytic hydrolysis over recyclable solid acids is one of the most enviromentally friendly ways for the conversion of biomass into chemicals. In this paper, a magnetic solid acid, Fe 3 O 4 @SiO 2 @NH-(CH 2 ) 2 -NH 2 @SO 3 H with the particle size of about 80 nm, was synthesized by using Fe 3 O 4 (~ 20 nm) as a magnetic core and then coated orderly with tetraethyl orthosilicate (TEOS) and N-{3-(Trimethoxysilyl) propyl} ethylenediamine (TMPED) by sol-gel reactions in water/ethanol solution, followed by the sulfonation of chlorosulfonic acid. The solid acid was characterized by Fourier transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA), scanning electron microscope (SEM), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), and X-ray photoelectron spectroscopy (XPS). The content of acidic sites on the surface of the solid acid was 1.01 mmol/g, measured by back titration method. The prepared solid acid was used to hydrolyze and extract diosgenin from Dioscorea nipponica Makino (DNM). The results show that the magnetic solid acid has higher hydrolysis activity than 2.5 M hydrochloric acid under same hydrolysis conditions, at 110 °C for 5 h. In addition, the magnetic solid acid can be easily separated from the reaction mixture by the application of a magnet and reused several times without significant activity loss. This work has a potential application value for the extraction of diosgenin from plants.

CAS / MDL: 512-04-9
研究领域: 植物化学 · 环境科学 · 材料科学
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PHYTOMEDICINE · 2025 · IF 8.3

Diosgenin ameliorates colitis by inhibiting mitochondrial DNA synthesis in macrophages via STAT2-CMPK2 pathway

Xin Qiao,Lei Zhang,Ting Wang,Xinyi Liang,Shenmeng Yao,Lei Wang,Gaoxiang Ma,Jie Yang,Xiaodong Wen

Background Ulcerative colitis (UC) is a chronic inflammatory bowel disease with rising global prevalence, posing ongoing therapeutic challenges. Diosgenin (DSG), a natural steroidal saponin, exhibits anti-inflammatory properties. However, its molecular mechanisms in UC are poorly understood. Purpose This study sought to clarify the molecular mechanisms and therapeutic targets responsible for DSG's protective effects against UC. Methods A murine colitis model induced by dextran sulfate sodium was used to assess DSG efficacy. Mechanistic insights were obtained from RNA sequencing analysis and confirmed in RAW264.7 and bone marrow-derived macrophages through Stat2 knockdown/overexpression experiment. Chromatin immunoprecipitation and surface plasmon resonance assays were used to investigate DSG-STAT2 interactions. Results DSG markedly alleviated colonic inflammation and tissue damage in DSS-treated mice. It significantly modulated macrophage polarization in colonic lamina propria lymphocytes. RNA-seq and Western blotting revealed that DSG selectively suppressed STAT2 phosphorylation and CMPK2 expression in macrophages, while attenuated LPS-induced mitochondrial DNA (mtDNA) synthesis and mitochondrial ROS (mtROS) production. STAT2 directly bound to the Cmpk2 promoter, and Stat2 silencing abolished LPS-driven Cmpk2 transcription and mtDNA synthesis. DSG interacted with STAT2 at Pro630 and Lys689 residues, and its inhibitory effects on CMPK2 and mtDNA were reversed by STAT2 overexpression. Conclusions DSG exerts its anti-colitis effects by selectively targeting STAT2 at Pro630 and Lys689, thereby suppressing CMPK2-mediated mtDNA overproduction. The discovery of a STAT2-dependent mechanism in DSG presents a potential therapeutic approach for UC.

CAS / MDL: 89-57-6
研究领域: 免疫学 · 分子生物学 · 药理学 · 胃肠病学
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Hydrogen bond regulation to promote the direct production of diosgenin from Dioscorea zingiberensis rhizomes

Yongxian Niu,Xi zhang,Wenbing Yu,Han Yin,Rui Lu,Zhenggang Liu,Fang Lu

Herein, a renewable system consisted of tartaric acid and isopropanol was developed to produce diosgenin efficiently from Dioscorea zingiberensis rhizomes. The yield of diosgenin reached 4.15% comparable to the highest value reported in previous researches. The combination of experiment and DFT calculation revealed that the acid-alcohol system could regulate the hydrogen bond interaction of each component in the rhizomes to disassemble the connection network and promote the release of saponin. Meanwhile, the intramolecular hydrogen bond of tartaric acid and the steric hindrance effect of isopropanol could prevent the esterification reaction and maintain the strong acidity of the system for the high yield of diosgenin. The scale-up experiment with a 100-fold feeding capacity was also conducted successfully. Furthermore, the technological process integrated with purification of diosgenin, recovery of organic acid and solvent and upgrading of residual solid to porous carbon materials has been established systematically to verify the prospective of industrialization.

研究领域: 植物化学 · 药物化学
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BIORESOURCE TECHNOLOGY · 2026 · IF 8.2

Efficient alcoholysis of saponins to diosgenin catalyzed by sulfonated biochar from Dioscorea zingiberensis residue

Wenbing Yu,Lishan Chen,Han Yin,Rui Lu,Zhenggang Liu,Fang Lu

Diosgenin represents a key precursor in the synthesis of steroidal pharmaceuticals, yet its conventional production relies on strong acid hydrolysis, which generates substantial acidic wastewater and poses serious environmental concerns. To circumvent these issues, a sustainable strategy for precise engineering of acid site in biochar catalysts derived from Dioscorea zingiberensis residues is presented. The carbon supports were prepared by direct calcination of the biomass residues across a controlled temperature range without exogenous additives, allowing tailored specific surface parameters. Subsequent sulfonation introduced sulfonic acid groups as the primary active sites, along with carboxylic acid groups and other weak acid species. A linear correlation was identified between the specific surface area and total acid site density, enabling rational regulation of acidic properties. Alcoholysis of saponins catalyzed by C-800-SO 3 H (derived from calcination at 800 °C with subsequent sulfonation) enabled a diosgenin yield of 23.26% based on crude saponins, equivalent to 4.39% relative to the raw rhizome mass. Catalytic performance correlated strongly with sulfonic acid density, indicating that sulfonic acid groups dominate the catalytic conversion. The catalyst also retained considerable activity over five reuse cycles. This work establishes a rational and eco-compatible route for designing high-performance solid acid catalysts from biomass waste, demonstrating promising potential for green production of pharmaceutical intermediates.

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FOOD RESEARCH INTERNATIONAL · 2021 · IF 6.475

Water-in-oil Pickering emulsions stabilized solely by a naturally occurring steroidal sapogenin: Diosgenin

Zheng Wan,Huiping Xia,Shiyin Guo,Chaoxi Zeng

In this study, stable water-in-oil emulsions stabilized solely by a naturally occurring steroidal sapogenin was reported for the first time. The results show that a concentrated emulsion with an internal water ratio of up to 60% can be obtained with only 3% of diosgenin concentration. The concentration of diosgenin had a significant effect on the microstructure and rheological properties of the emulsions. More importantly, the emulsion has excellent freeze/thaw stability and thermal stability. The results of polarized light microscopy, CLSM, and XRD indicate that the great structural properties and high stability of the emulsion can be attributed to the combined action of the diosgenin crystal shells on the droplet surface and needle-crystals in the continuous phase. That is, Pickering stabilization and network stabilization acting synergistically on stabilization of the emulsions. This novel food grade water-in-oil emulsions demonstrated great potential for application in food and biomedical-related fields.

CAS / MDL: 512-04-9 3625-57-8
研究领域: 食品科学 · 生物化学
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2024 ·Vol. 25 ·期 24 ·13399 · IF 4.9

Protective Effects of Dioscin and Diosgenin on Plateau Hyperuricemia by Attenuating Renal Inflammation via EPHX2

Wanyun Dang,Fangyang Li,Rong Gao,Cheng Zhang,Hongbo Cheng,Zhenhui Wu,Tingyu Yang,Jinchao Pan,Xianglin Tang,Yue Gao

Plateau hyperuricemia is a common disease in the plateau area, and the incidence is much higher than that in the plain area. Dioscin (DIO) and its active metabolite Diosgenin (DG) exert therapeutic effects on hyperuricemia through oxidative stress and inflammation. In this study, DIO and its active metabolite DG were taken as the research objects to explore their therapeutic effects on high-altitude hyperuricemia in rats. To evaluate the therapeutic effect of DIO on the rat model of high-altitude hyperuricemia, the evaluation indexes include blood biochemical indexes, renal histopathology, oil red O staining of the kidney, rat kidney index, and rat renal inflammatory factors. Transcriptomics was used to analyze the control group, model group, and drug-administered group to preliminarily explore the protective mechanism of DIO in rats with high-altitude hyperuricemia. An HK-2 high-altitude hyperuricemia cell injury model was established to verify the therapeutic mechanism of DIO in rats with high-altitude hyperuricemia. Western blot was used to detect the expression of related proteins in renal tissues and cell models. The results showed that DIO and its active metabolite DG regulate renal lipid metabolism through the EPHX2 gene, attenuate renal inflammatory reaction, and then promote the excretion of uric acid and reduce its reabsorption, which ultimately achieves the effect of treating plateau hyperuricemia.

CAS / MDL: 69-93-2
研究领域: 药理学 · 肾病学 · 分子生物学
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