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Anticancer Activity of diosgenin and Its Molecular Mechanism

Chinese Journal of Integrative Medicine 2023年第8期29卷 738-749页

作者： REN Qun-li WANG Qian ZHANG Xin-qun WANG Miao HU Huan TANG Jun-jie YANG Xiong-tong RAN Ying-hui LIU Huan-huan SONG Zhi-xing LIU Jian-guo LI Xiao-lan Special Key Laboratory of Microbial Resources and Drug Development of Guizhou Higher Education Institution Zunyi Medical UniversityZunyiGuizhou Province(563000)China School of Stomatology Zunyi Medical UniversityZunyiGuizhou Province(563000)China Institute of Life Sciences Zunyi Medical UniversityZunyiGuizhou Province(563000)China Zheng'an County People's Hospital ZunyiGuizhou Province(563000)China School of Basic Medicine Zunyi Medical UniversityZunyiGuizhou Province(563000)China

diosgenin, a steroidal sapogenin, obtained from Trigonella foenum-graecum, Dioscorea, and Rhizoma polgonati, has shown high potential and interest in the treatment of various cancers, such as oral squamous cell carcinoma, laryngeal cancer, esophageal cancer, liver cancer, gastric cancer, lung cancer, cervical cancer, prostate cancer, glioma, and leukemia. This article aims to provide an overview of the in vivo, in vitro,and clinical studies reporting the diosgenin’s anticancer effects. Preclinical studies have shown promising effects of diosgenin on inhibiting tumor cell proliferation and growth, promoting apoptosis, inducing differentiation and autophagy, inhibiting tumor cell metastasis and invasion, blocking cell cycle, regulating immunity and improving gut microbiome. Clinical investigations have revealed clinical dosage and safety property of diosgenin. Furthermore, in order to improve the biological activity and bioavailability of diosgenin, this review focuses on the development of diosgenin nano drug carriers, combined drugs and the diosgenin derivatives. However, further designed trials are needed to unravel the diosgenin’s deficiencies in clinical application.

关键词： diosgenin steroidal sapogenin anticancer molecular mechanism biological activity

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Network pharmacology and molecular docking analysis reveal insights into the molecular mechanism of Gualou Qumai Wan in clear cell renal cell carcinoma

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TMR Modern Herbal Medicine 2024年第2期7卷 11-18页

作者： Zhi-Qiang Wang Zhen-Yu Mu Bo Yang Tao Wang Zhi-Yong Su Shan-Chun Guo Jiang-Xia Yin Department of Urology Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China Medical Insurance Office Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China Intensive Care Unit Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China Department of Anal Surgery Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China Department of Neurosurgery Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China RCMI Cancer Research Center Xavier University of LouisianaLA 1870125USA Department of Medical Oncology Shouguang Hospital of Traditional Chinese MedicineShouguang 262700China

Background:To initially clarify the potential therapeutic targets and pharmacological mechanism regarding Gualou Qumai Wan(GQW),a kind of traditional Chinese medicine(TCM),in clear cell renal cell carcinoma(ccRCC)by virtue of the network pharmacology analysis and molecular docking analysis.Methods:The screening of bioactive components and targets of GQW was based on the Traditional Chinese Medicine System Pharmacology(TCMSP)and the UniProt platform served for standardizing their targets.Online Mendelian Inheritance in Man(OMIM),PharmGkb,TTD,DrugBank and GeneCards databases were searched to collect the disease targets of ccRCC.Cytoscape assisted in constructing herb-compound-target(H-C-T)networks.The STRING database was searched for constructing the target protein-protein interaction(PPI)networks,while the R programming language served for analyzing GO functional terms and the KEGG pathways related to potential targets.Analyses of core genes related to survival and tumor microenvironment(TME)were conducted respectively based on the GEPIA2 database and TIMER 2.0 database.Human Protein Atlas(HPA)and The Cancer Genome Atlas(TCGA)helped to obtain core genes’protein expression as well as transcriptome expression level.Autodock Vina software validated the molecular docking regarding GQW components and pivotal targets.Results:The constructed H-C-T networks mainly had 33 compounds and 65 targets.A topological analysis of the PPI network identified that ESR1,AKT1,HIF1A,PTGS2,TP53 and VEGFA serve as core targets in the way GQW affects ccRCC.According to the GO and KEGG pathway enrichment analyses,the effects of GQW are mediated by genes related to hypoxia and oxidative stress as well as the Chemical carcinogenesis-receptor activation and PI3K-Akt signaling pathways.AKT1 shows a close relation to the recruitment of various immune cells and can remarkably affect disease prognosis according to reports.Molecular docking and molecular dynamics simulations showed that diosgenin has higher affinity with core targets.Conclusion:The

关键词： Gualou Qumai Wan AKT1 PI3K-Akt signaling pathway network pharmacology diosgenin clear cell renal cell carcinoma

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Induction of antiproliferative effect by diosgenin through activation of p53, release of apoptosis-inducing factor (AIF) and modulation of caspase-3 activity in different human cancer cells

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Cell Research 2004年第3期14卷 188-196页

作者： Cecile CORBIERE Bertrand LIAGRE Faraj TERRO Jean-Louis BENEYTOUT Faculté de Pharmacie rue du Docteur Marcland France Laboratoire de Biochimie UPRES EA 1085 87025 Limoges Cedex Service d’Histologie et Biologic Cellulaire Faculte de Medecine

Previously, we demonstrated that a plant steroid, diosgenin, altered cell cycle distribution and induced apoptosis in the human osteosarcoma 1547 cell line. The objective of this study was to investigate if the antiproliferative effect of diosgenin was similar for different human cancer cell lines such as laryngocarcinoma HEp-2 and melanoma M4Beu cells. Moreover, this work essentially focused on the mitochondrial pathway. We found that diosgenin had an important and similar antiproliferative effect on different types of cancer cells. In addition, our new results show that diosgenin-induced apoptosis is caspase-3 dependent with a fall of mitochondrial membrane potential, nuclear localization of AIF and poly (ADP-ribose) polymerase cleavage. diosgenin treatment also induces p53 activation and cell cycle arrest in the different cell lines studied.

关键词： diosgenin apoptosis p53 AIF caspase cancer cells.

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Advances in the pharmacological activities and mechanisms of diosgenin

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Chinese Journal of Natural Medicines 2015年第8期13卷 578-587页

作者： CHEN Yan TANG You-Mei YU Su-Lan HAN Yu-Wei KOU Jun-Ping LIU Bao-Lin YU Bo-Yang Jiangsu Key Laboratory of TCM Evaluation and Translational Research Department of Complex Prescription of TCM China Pharmaceutical University

diosgenin, a well-known steroid sapogenin derived from plants, has been used as a starting material for production of steroidal hormones. The present review will summarize published literature concerning pharmacological potential of diosgenin, and the underlying mechanisms of actions. diosgenin has shown a vast range of pharmacological activities in preclinical studies. It exhibits anticancer, cardiovascular protective, anti-diabetes, neuroprotective, immunomodulatory, estrogenic, and skin protective effects, mainly by inducing apoptosis, suppressing malignant transformation, decreasing oxidative stress, preventing inflammatory events, promoting cellular differentiation/proliferation, and regulating T-cell immune response, etc. It interferes with cell death pathways and their regulators to induce apoptosis. diosgenin antagonizes tumor metastasis by modulating epithelial-mesenchymal transition and actin cytoskeleton to change cellular motility, suppressing degradation of matrix barrier, and inhibiting angiogenesis. Additionally, diosgenin improves antioxidant status and inhibits lipid peroxidation. Its anti-inflammatory activity is through inhibiting production of pro-inflammatory cytokines, enzymes and adhesion molecules. Furthermore, diosgenin drives cellular growth/differentiation through the estrogen receptor(ER) cascade and transcriptional factor PPARγ. In summary, these mechanistic studies provide a basis for further development of this compound for pharmacotherapy of various diseases.

关键词： diosgenin Steroid sapogenin Pharmacological activities Multiple targets

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Designing and optimizing a parallel neural network model for predicting the solubility of diosgenin in n-alkanols

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Chinese Journal of Chemical Engineering 2021年第1期34卷 288-294页

作者： Huichao Lv Dayong Tian School of Chemical&Environmental Engineering Anyang Institute of TechnologyAnyang 455000China

Accurate estimation of the solubility of a chemical compound is an important issue for many industrial proce sses.To overcome the defects of some thermodynamic models and simple correlations,a parallel neural network(PNN) model was conceived and optimized to predict the solubility of diosgenin in seven n-alkanols(C_(1)-C_(7)).The linear regression analysis of the parity plots indicates that the PNN model can give more accurate descriptions of the solubility of diosgenin than the ordinary neural network(ONN) model.The comparison of the average root mean square deviation(RMSD) shows that the suggested model has a slight advantage over the thermodynamic NRTL model in terms of the calculating precision.Moreover,the PNN model can reflect the effects of the temperature and the chain length of the alcohol solvent on the solution behavior of diosgenin correctly and can estimate its solubility in the n-alkanols with more carbon atoms.

关键词： Solubility diosgenin Parallel neural network model NRTL model

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Inhibitory Effect of diosgenin on Experimentally Induced Benign Prostatic Hyperplasia in Rats

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Journal of Huazhong University of Science and Technology(Medical Sciences) 2016年第6期36卷 806-810页

作者：陈静章怀奋熊朝梅阮金兰 Department of Pharmacy the First People's Hospital of Yueyang School of Pharmacy Tongji Medical CollegeHuazhong University of Science and Technology

This study investigated the effect of diosgenin,a natural sapogenin possessing various pharmacological activities,on benign prostatic hyperplasia（BPH） in rats and the possible mechanisms.BPH was established in the castrated rats by subcutaneous injection of testosterone propionate.Animals were randomly divided into four groups（n=10 each）：model group（0.5% sodium carboxymethyl cellulose）;positive control group（3 mg/kg finasteride）;two diosgenin groups（50 and 100 mg/kg）.The drugs were intragastricaly given in each group for consecutive 3 weeks.Another 10 rats with no testicles cut off served as negative controls and they were subcutaneously injected with 0.1 m L olive oil per day and then treated with 0.5% sodium carboxymethylcellulose.After 3-week administration,the prostate index and serum PSA level were determined,and histopathological examination was carried out.The levels of MDA,SOD and GPx in prostates were also measured.Additionally,the expression of Bcl-2,Bax and p53 was examined using Western blotting.The results showed that the prostate index and serum PSA level were significantly decreased,and the pathological changes of the prostate gland were greatly improved in diosgenin groups as compared with the model group.Elevated activities of SOD and GPx,and reduced MDA level were also observed in diosgenin-treated rats.In addition,the expression of Bcl-2 in prostates was down-regulated,whereas that of Bax and p53 was up-regulated in diosgenin-treated rats.These results indicated that diosgenin was effective in inhibiting testosterone propionate-induced prostate enlargement and may be a candidate agent for the treatment of BPH.

关键词： diosgenin benign prostatic hyperplasia oxidative stress apoptosis

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Syntheses and Anti-cancer Activities of Glycosylated Derivatives of diosgenin

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Chemical Research in Chinese Universities 2017年第1期33卷 80-86页

作者： TAN Yonghua XIAO Xiao YAO Jianing HAN Fei LOU Huayong LUO Heng LIANG Guangyi BEN-DAVID Yaacov PAN Weidong Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences Guiyang 550002 P R. China Key Laboratory of Chemistry for Natural Products of Guizhou Medical University Guiyang 550001 P. R. China

In order to obtain better anti-cancer compounds, nine glycosylated derivatives were designed and synthe- sized using diosgenin as starting material. Their structures were confn-med by 1H NMR, 13C NMR and MS spectra. The anti-cancer activities of intermediate compounds 5a-5i and the target compounds 6a-6i were investigated against human leukemia HEL, K562, HL60 and melanoma WM9 cell lines via MTT method. The bioassay results show that these derivatives possess good inhibitory activities against the four cancer cell lines. Furthermore, these derivatives show better inhibitory activities against K562 than against other cell lines, and most derivatives show better inhibitory activities than the parental material. Moreover, compounds 6a--6i are more active than their inter- mediates 5a--5i when against these ceils. The above results demonstrate the effects of glycosylation on 3-OH of di- osgenin and acetylation of the sugar moiety on their antitumor activities.

关键词： diosgenin Glycosylation Anti-cancer activity

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Crystal Structures, Stability, and Solubility Evaluation of a 2:1 diosgenin-Piperazine Cocrystal

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Natural Products and Bioprospecting 2020年第4期10卷 261-267页

作者： Ningbo Gong Hongmei Yu Ying Wang Cheng Xing Kun Hu Guanhua Du Yang Lu Beijing Key Laboratory of Polymorphic Drugs Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China Beijing City Key Laboratory of Drug Target Identification and Drug Screening Institute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050China

A cocrystal of diosgenin with piperazine in 2:1 stoichiometry was successfully synthesized.The solid form was prepared by liquid assisted grinding,slurry and crystallization methods.The cocrystal was characterized by powder X-ray diffraction,differential scanning calorimetry,thermogravimetric analysis,Fourier transform infrared spectroscopy,and structure determined by single crystal X-ray diffraction,the hydrogen bonds formed into fish bone structure along the[010]direction and all the molecules packed into 3D layer structure along a axis.After formation of cocrystal,the solubility of diosgenin was improved,and the solubility value in 0.2%SDS solution was approximately 1.5 times as large as that of the parent material.

关键词： diosgenin Piperazine Cocrystal Characterization Solubility

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Hairy Root Induction in Helicteres isora L.and Production of diosgenin in Hairy Roots

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Natural Products and Bioprospecting 2014年第2期4卷 107-112页

作者： Vinay Kumar Dnyanada Desai Varsha Shriram Department of Biotechnology Modern CollegeGaneshkhindPune 411016India Department of Botany Prof.Ramkrishna More CollegeAkurdiPune 411044India

Mature seeds of Helicteres isora L.were collected from seven geographical locations of Maharashtra and Goa(India)and evaluated for diosgenin(a bioactive steroidal sapogenin of prime importance)extraction and quantification.Chemotypic variations were evidenced with diosgenin quantity ranging from 33 lg g^(-1)seeds(Osmanabad forests)to 138 lg g^(-1)(Khopoli region).Nodal and leaf explants from in vitro-raised seedlings were used for callus and Agrobacterium-mediated transformation,respectively.Compact,hard,whitish-green callus(2.65 g explant-1)was obtained on MS?13.32 lM BAP?2.32 lM Kin after 30 days of inoculation.Various parameters including types of explant and Agrobacterium strain,culture density,duration of infection and various medium compositions were optimized for hairy root production.A.rhizogenes strain ATCC-15834 successfully induced hairy roots from leaf explants(1 cm2)with 42%efficiency.Transgenic status of the roots was confirmed by PCR using rolB and VirD specific primers.Hairy roots showed an ability to synthesize diosgenin.diosgenin yield was increased*8 times in hairy roots and*5 times in callus than the seeds of wild plants.Enhanced diosgenin content was associated with proline accumulation in hairy roots.This is the first report on induction of hairy roots in H.isora.

关键词： diosgenin Helicteres isora Hairy roots

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Oxidation of Hecogenin and diosgenin Derivatives with Dimethyldioxirane

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Chinese Chemical Letters 2005年第2期16卷 143-146页

作者： BaoKunZHU HongBinZHANG YuShunZHANG HuiMinZHONG JianPingLIU TheSchoolofPharmacy CenterforAdvancedStudiesofMedicinalandOrganicChemistryYunnanUniversityKunming650091 TheSchoolofChemistry QingdaoSci.＆Techn.Univ.Qingdao266042

Diacetyl derivative of hecogenin 1 was oxidized to unsaturated ketone 5 via allylic alcohol 3 when it reacted with dimethyldioxirane (DMDO). The structure of 3 was confirmed by X-ray crystal analysis and the highly regioselectivity of DMDO to different olefin bonds was also observed when diosgenin derivative 6 was treated with DMDO.

关键词： Oxidation dimethyldioxirane hecogenin diosgenin derivative.

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