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1.
Diosgenin is an important precursor for synthesis of more than 200 steroidal hormone medicines. Rhizome of Dioscorea zingiberensis C. H. Wright (RDZ) contained the highest content of diosgenin in Dioscorea plant species. Diosgenin is traditionally extracted by acid hydrolysis from RDZ. However, the acid hydrolysis process produces massive wastewater which caused serious environment pollution. In this study, diosgenin extraction by direct biotransformation with Penicillium dioscin was investigated. The spawn cultivation conditions were optimized as: Czapeks liquid culture medium without sugar and agar (1,000 ml) + 6.0 g dioscin/6.0 g DL, 30 °C, 36 h; solid fermentation of RDZ: mycelia/RDZ of 0.05 g/kg, 30 °C, 50 h; the yield of diosgenin was over 90 %. Spawn cultivation was crucial for the direct biotransformation. In the spawn cultivation, amount and ratio of dioscin/DL were the key factors to promote biotransformation activity of P. dioscin. This biotransformation method was environment-friendly, simple and energy saving, and might be a potential substitute for acid hydrolysis in diosgenin extraction industry. 相似文献
2.
Atropurosides A-G (1-7), seven new steroidal saponins, which possess new polyhydroxylated aglycones, were isolated from the rhizomes of Smilacina atropurpurea (Convallariaceae), together with a known saponin, dioscin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR techniques and chemical methods. Antifungal testing of the eight compounds indicated that atropurosides B (2) and F (6) were fungicidal against Candida albicans, Candida glabrata, Cryptococcus neoformans, and Aspergillus fumigatus with minimum fungicidal concentrations (MFCs) < or = 20 microg/ml, while dioscin (8) was selectively active against C. albicans and C. glabrata (MFC < or = 5.0 microg/ml). Furthermore, the antifungal saponins 2, 6, and 8 were evaluated for their in vitro cytotoxicities in a panel of human cancer cell lines (SK-MEL, KB, BT-549, SK-OV-3, and HepG2) and non-cancerous Vero cells. All showed moderate cytotoxicities. It appears that the antifungal activity of these steroidal saponins correlates with their cytotoxicity against mammalian cells. 相似文献
3.
Won-Chul Lim Hyunhee Kim Young-Joo Kim Kyung-Chul Choi In Ho Lee Ki Heon Lee Mi Kyung Kim Hyeonseok Ko 《Bioorganic & medicinal chemistry letters》2017,27(15):3342-3348
Epithelial-to-mesenchymal transition (EMT), an important cellular process, occurs during cancer development and progression, has a crucial role in metastasis by enhancing the motility of tumor cells. Dioscin is a polyphenolic component isolated from Phyllanthus amarus, which exhibits a wide range of pharmacological and physiological activities, such as anti-tumor, anti-inflammatory, anti-obesity, anti-fungal, and anti-viral activities. However, the possible role of dioscin in the EMT is unclear. We investigated the suppressive effect of dioscin on the EMT. Transforming growth factor-beta 1 (TGF-β1) is known to induce EMT in a number of cancer cell types and promote lung adenocarcinoma migration and invasion. To verify the inhibitory role of dioscin in lung cancer migration and invasion, we investigated the use of dioscin as inhibitors of TGF-β1-induced EMT in A549 lung cancer cells in vitro. Here, we found that dioscin prominently increased expression of the epithelial marker E-cadherin and expression of the mesenchymal marker N-cadherin and Snail during the TGF-β1-induced EMT. In addition, dioscin inhibited the TGF-β1-induced increase in cell migration and invasion of A549 lung cancer cells. Also, dioscin remarkably inhibited TGF-β1-regulated activation of MMP-2/9, Smad2, and p38. Taken together, our findings provide new evidence that dioscin suppresses lung cancer migration, and invasion in vitro by inhibiting the TGF-β1-induced EMT. 相似文献
4.
3-O-beta-Chacotriosyl-26-O-beta-D-glucopyranosyl-(25R)-furost-5-en (1), a mimic of the antitumor active proto-dioscin, was concisely synthesized from diosgenin in a linear nine steps and in 17% overall yield. Its congeners with a alpha-l-rhamnopyranosyl, beta-lactosyl, or without a substituent at the 26-OH (13-15) were also prepared. Compound 1, as well as 13-15, did not show any inhibition against tumor cells, implying that proto-dioscin might be also inactive, but readily converted into the antitumor active dioscin. 相似文献
5.
Zhu S Zhang Y Li M Yu J Zhang L Li Y Yu B 《Bioorganic & medicinal chemistry letters》2006,16(21):5629-5632
Two series of dioscin derivatives (4a-o and 5a-o) with selected modifications at the 6' and 4' positions of the chacotriosyl residue, respectively, were synthesized. All the 6'-N-acyl-dioscin derivatives did not show considerable inhibitory activities at 10 microM, while most of the 4'-O-(2-N-acyl)ethyl-dioscin derivatives behaved as potent as dioscin, against the growth of tumor cells. 相似文献
6.
7.
Koorbanally NA Koorbanally C Harilal A Mulholland DA Crouch NR 《Phytochemistry》2004,65(23):3069-3073
Two bufadienolides, 6beta-acetoxy-3beta,8beta,14beta-trihydroxy-12-oxobufa-4,20,22-trienolide and 14beta-hydroxybufa-3,5,20,22-tetraenolide were isolated from the dichloromethane extract of the bulbs of Drimia robusta and the methanol extract of the bulbs of Urginea epigea, respectively. The bulbs of Drimia robusta also yielded several known compounds, 6beta-acetoxy-3beta,8beta,12beta,14beta-tetrahydroxybufa-4,20,22-trienolide (12beta-hydroxyscillirosidin) from the dichloromethane extract and three common aromatic acids, 4-hydroxy-3-methoxybenzoic acid, 3,4-dihydroxybenzoic acid, and trans-3-(4'-hydroxyphenyl)-2-propenoic acid from the ethyl acetate extract. 相似文献
8.
YANG Fan HAN Yu CONG Tian-shen KANG Yi LI Yan SUN Kai YIN Yong-qiang LOU Jian-shi 《中国应用生理学杂志》2016,32(3):209-213
目的:观察薯蓣皂苷(Dio)对大鼠心肌收缩作用以及胞内Ca2+浓度的影响,并初步探讨其作用机制与Na+-Ca2+交换体(NCX)的关系。方法:采用Langendorff逆行主动脉灌流法对大鼠离体心脏进行灌流,利用压力感受器插管法测定左心室相关心功能参数,记录及其在应用NCX选择性抑制剂SEA0400情况下对左心室收缩压(LVSP)、左心室舒张末期压(LVEDP)、左心室内压最大上升/下降速率(±dp/dtmax)以及心率(HR)的影响;利用激光共聚焦显微观察薯蓣皂苷及SEA0400对大鼠心肌细胞H9c2细胞内Ca2+浓度的影响。结果:离体心脏灌流结果显示,1 μmol/L Dio可显著增加LVSP,增加约19.7%(P<0.01);增加左室内压最大上升速率(+dp/dtmax),增加约9.6%;激光共聚焦测定Ca2+荧光强度实验结果显示:1 μmol/L Dio可使H9c2细胞中Ca2+相对荧光强度增加(P<0.01);而在SEA0400存在的情况下,1 μmol/L的Dio使细胞内Ca2+相对荧光强度变为(17.09±0.63),给予Dio后差异有显著性(P<0.01)。在细胞液中无Ca2+或无Na+时,给予1 μmol/L的Dio使Ca2+相对荧光强度减小,与给予1 μmol/L的Dio差异有显著性(P<0.01)。结论:Dio可增加左心室收缩压和最大上升速率,表现正性肌力作用;Dio可使细胞内Ca2+浓度增加,其作用机制与增加Na+内流,促进NCX反向转运有关。 相似文献
9.
Hao Chen Lina Xu Lianhong Yin Youwei Xu Xu Han Yan Qi Yanyan Zhao Kexin Liu Jinyong Peng 《Proteomics》2014,14(1):51-73
Dioscin shows various pharmacological effects. However, its activity on colorectal cancer is still unknown. The present work showed that dioscin significantly inhibited cell proliferation on human HCT‐116 colon cancer cells, and affected Ca2+ release and ROS generation. The content of nitric oxide (NO) and its producer inducible NO synthase (iNOS) associated with DNA damage and aberrant cell signaling were assayed using the kits. DNA damage and cell apoptosis caused by dioscin were also analyzed through single‐cell gel electrophoresis and in situ terminal deoxynucleotidyl transferase dUTP nick‐end labeling assays. The results showed that dioscin increased the levels of NO and inducible NO synthase. The comet length in dioscin‐treated groups was much longer than that of the control group, and the number of terminal deoxynucleotidyl transferase dUTP nick‐end labeling positive cells (apoptotic cells) was significantly increased by the compound (p < 0.01). Furthermore, dioscin caused mitochondrial damage and G2/M cell cycle arrest through transmission electron microscopy and flow cytometry analysis, respectively. To study the cytotoxic mechanism of dioscin, an iTRAQ‐based proteomics approach was used. There were 288 significantly different proteins expressed in response to dioscin, which were connected with each other and were involved in different Kyoto Encyclopedia of Genes and Genomes pathways. Then, some differentially expressed proteins involved in oxidative phosphorylation, Wnt, p53, and calcium signaling pathways were validated by Western blotting and quantitative real‐time PCR assays. Our work elucidates the molecular mechanism of dioscin‐induced cytotoxicity in colon cancer cells, and the identified targets may be useful for treatment of colorectal cancer in future. 相似文献
10.
Qiuyue Ding Wenda Zhang Cheng Cheng Fengbo Mo Lei Chen Guangfu Peng Xianyi Cai Jinglong Wang Shuhua Yang Xianzhe Liu 《Journal of cellular physiology》2020,235(3):2911-2924
Pyroptosis is a form of programmed cell death (PCD) that plays a vital role in immunity and diseases. Although it was recently reported that chemotherapy drugs can induce pyroptosis through caspase-3-dependent cleavage of gasdermin E (GSDME), the role of pyroptosis in osteosarcoma (OS) with dioscin is less understood. In this study, we explored the effects of dioscin on OS in vitro and in vivo and further elucidated the underlying molecular mechanisms and found that dioscin-triggered pyroptosis in GSDME-dependent cell death and that GSDME-N was generated by caspase-3. Furthermore, dioscin inhibited cancer cell growth by inducing G2/M arrest and apoptosis through the JNK/p38 pathway. In vivo, dioscin significantly inhibited OS proliferation. Taken together, our results demonstrate that dioscin can induce apoptosis through the JNK/p38 pathway and GSDME-dependent pyroptosis in OS, identifying it as a potential therapeutic drug for treatment of this disease. 相似文献
11.
Li W Qiu Z Wang Y Zhang Y Li M Yu J Zhang L Zhu Z Yu B 《Carbohydrate research》2007,342(18):2705-2715
Dioscin derivatives (1-12) with a variety of substitutions at the 6'-OH of the chacotriosyl residue and the 3',6'-anhydrosaponin derivatives (26, 30, and 32) were synthesized. All these derivatives showed much lower cytotoxicity than that of the parent dioscin, while their hemolytic activities were partially retained depending on the various 6'-O-substitutions. 相似文献
12.
Alpha-L-rhamnopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranose (chacotriose) is the oligosaccharide moiety of dioscin. Chacotriosyl trichloroacetimidate was synthesized from d-glucose and l-rhamnose, and glycosylated to mevalonate (diosgenin, cholesterol, and glycyrrhetic acid) to yield dioscin and neosaponins. In order to simplify the structure of the aglycone part, the mevalonate moiety was replaced with double-chain neoglycolipids that mimicked glycosyl ceramides. A cytotoxicity test revealed the importance of the glycosidic linkage of the naturally occurring beta-form and that dioscin and the neoglycolipid with the longest chain showed a moderate activity. 相似文献
13.
Luyun Cui Guangdie Yang Jiani Ye Yinan Yao Guohua Lu Junjun Chen Liangjie Fang Shan Lu Jianying Zhou 《Journal of cellular and molecular medicine》2020,24(16):9217-9230
Tumour‐associated macrophage (TAM) is an important component in tumour microenvironment. Generally, TAM exhibits the function of M2‐like macrophage, which was closely related to angiogenesis and tumour progression. Dioscin, a natural steroidal saponin, has shown its powerful anti‐tumour activity recently. However, the mechanism of dioscin involved in immune regulation is still obscure. Here, we observed dioscin induced macrophage M2‐to‐M1 phenotype transition in vitro and inhibited IL‐10 secretion. Meanwhile, the phagocytosis of macrophages was enhanced. In subcutaneous lung tumour models, dioscin inhibited the augmentation of M2 macrophage populations. Furthermore, dioscin down‐regulated STAT3 and JNK signalling pathways in macrophages in vitro. In BMDMs, activating JNK and inhibiting STAT3 induce macrophages to M1 polarization while inhibiting JNK and activating STAT3 to M2 polarization. Additionally, condition mediums from dioscin‐pre‐treated macrophages inhibited the migration of 3LL cells and the tube‐formation capacity of HUVECs. What's more, dioscin‐mediated macrophage polarization inhibited the in vivo metastasis of 3LL cells. In conclusion, dioscin may act as a new anti‐tumour agent by inhibiting TAMs via JNK and STAT3 pathways in lung cancer. 相似文献
14.
Bioassay-guided fractionation of MeOH extract from fenugreek (Trigonella foenum-graecum L.) seeds resulted in the isolation of two rat growth-hormone release stimulators in vitro, fenugreek saponin I (1) and dioscin (9), along with two new, i.e., 2 and 3, and five known analogues, i.e., 4-8. The structures of the new steroidal saponins, fenugreek saponins I, II, and III (1-3, resp.), were determined as gitogenin 3-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, sarsasapogenin 3-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, and gitogenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside, respectively. Fenugreek saponin I (1) and dioscin (9) caused ca. 12.5- and 17.7-fold stimulation of release, respectively, of rat growth hormone from rat pituitary cells, whereas gitogenin (5) showed moderate activity. To our knowledge, this is the first study to demonstrate that steroidal saponins stimulate rat growth-hormone release in rat pituitary cells. 相似文献
15.
16.
All possible eight monomethylated dioscin derivatives (1-8) were synthesized. Their inhibitory activities against P388 and A-549 cells were determined, and the results indicate that six of the eight hydroxyls of dioscin are the 'key polar groupings' for tumor inhibitory activities. 相似文献
17.
Dioscin (diosgenyl 2,4-di-O-alpha-l-rhamnopyranosyl-beta-d-glucopyranoside) is an important constituent of some traditional Chinese medicines with several bioactivities. We have investigated the pharmacokinetics of dioscin in rat after intravenous and oral administrations. Compartmental methods were used to perform pharmacokinetic data analysis. The dose-dependent pharmacokinetics of dioscin was characterized after intravenous administrations (0.064, 0.16, 0.4 and 1.0mg/kg) to rats. There was significant decrease in clearance with increasing dose (4.67+/-0.09 ml/min/kg (0.064 mg/kg) versus 3.49+/-0.23 ml/min/kg (1.0 mg/kg), P<0.05), and the plot of reciprocal clearance values versus the doses was linear (r=0.909, P<0.05). After an I.V. dose of 1mg/kg, simultaneous oral gavage of activated charcoal did not change the pharmacokinetic parameters indicating enterohepatic recycling of dioscin is not important in rat. The absolute oral bioavailability was very low (0.2%). In tissue distribution and bile excretion studies after I.V. and oral administrations, dioscin was shown to undergo a prolonged absorption from the intestinal tract and slow elimination from organs, and only a small amount of drug was recovered in bile. The cumulative amounts of dioscin in feces and urine indicated that the parent drug is mainly excreted in the feces. 相似文献
18.
Methyl protodioscin (MPD), a furostanol saponin, is a preclinical drug shown potent antiproliferative activities against most cell lines from leukemia and solid tumors. The metabolites of MPD in rats' urine after single oral doses of 80 mg/kg were investigated in this research. Ten metabolites were isolated and purified by liquid-liquid extraction, open-column chromatography, medium-pressure liquid chromatography, and preparative high-performance liquid chromatography. The structural identification of the metabolites was carried out by high resolution mass spectra, NMR spectroscopic methods including (1)H NMR, (13)C NMR and 2D NMR, as well as chemical ways. The 10 metabolites were elucidated to be dioscin (M-1), pregna-5,16-dien-3beta-ol-20-one-O-alpha-l-rhamnopyranosyl-(1-->2)-[alpha-l-rhamnopyranosyl-(1-->4)]-beta-d-glucopyranoside (M-2), diosgenin (M-3), protobioside (M-4), methyl protobioside (M-5), 26-O-beta-d-glucopyrannosyl(25R)-furan-5-ene-3beta, 22alpha, 26-trihydroxy-3-O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside(M-6),26-O-beta-d-glucopyranosyl(25R)-furan-5-ene-3beta,26-dihydroxy-22-methoxy-3-O-alpha-l-rhamnopyranosyl-(1-->4)-beta-d-glucopyranoside (M-7), prosapogenin A of dioscin (M-8), prosapogenin B of dioscin (M-9), and diosgenin-3-O-beta-d-glucopyranoside (M-10), respectively. M-1 was the main urinary metabolite of MPD in rats. Some metabolites showed potent antiproliferative activities against HepG2, NCI-H460, MCF-7 and HeLa cell lines in vitro. 相似文献
19.
Two new steryl esters with a polyhydroxylated ergostane-type nucleus, 3beta,5alpha-dihydroxy-(22E,24R)-ergosta-7,22-dien-6beta-yl oleate (1) and 3beta,5alpha-dihydroxy-(22E,24R)-ergosta-22-en-7-one-6beta-yl oleate (2), were isolated from the fruiting bodies of the basidiomycete Tricholomopsis rutilans along with three known sterols (3, 4, and 5). The structures of compounds 1 and 2 were established on the basis of spectroscopic means and chemical methods. 相似文献
20.
A novel steroid, 1alpha,3beta,5beta-trihydroxy-24-methylenecholestan-6-one (gibberoketosterol) (1), along with four known steroids, was isolated from the lipophilic extracts of a Taiwanese soft coral Sinularia gibberosa. The structure of the new metabolite was determined on the basis of extensive spectral analyses and chemical reaction. The relative stereochemistry of gibberoketosterol was established by the NOESY experiments and analysis of the pyridine-induced deshielding effect of the axial hydroxy groups. Gibberoketosterol is the first example of 1alpha,3beta,5beta-trihydroxy-6-oxosteroids isolated from natural sources and was found to exhibit a moderate cytotoxicity against the growth of Hepa59T/VGH cancer cells. 相似文献