Advances in study of dioscin——a natural product

XU Li-na1 WEI Yong-li1 PENG Jin-yong1

(1.College of Pharmacy, Dalian Medical University, Dalian, China 116044)
【Knowledge Link】residue; hydrolysate; glycosidic bond

【Abstract】Dioscin, a typical saponin, is widely present in the family of Dioscoreaceae, Liliaceae, Caryophyllaceae and Rosaceae, especially in Dioscoreaceae, including Discorea nipponica Makino, Dioscorea zingiberensis C. H. Wright and Dioscorea panthaica Prain et Burkill. Traditional Chinese medicine reported that dioscin plays a role in expectorant, relaxing the muscles and stimulating the blood circulation, aiding digestion and diuresis. With the development of science and technology in recent years, some new extraction and separation techniques and methods have been applied to the study of dioscin, and more and more pharmacological effects were found. Modern pharmacology studies have confirmed that dioscin had some activities on desensitization, anti-inflammatory, lipid-lowering, anti-tumor, hepatoprotection and anti-viral. After oral administration, dioscin is metabolized to diosgenin, which is the true active ingredient and is an important raw material to synthesize steroid hormone drugs. Therefore, the studies on dioscin are valueable and promising. In this review, we make a summary on the researches of dioscin including the extraction technology, separation and preparation, chemical synthesis, drug metabolism, determination and pharmacological researches.

【Keywords】 dioscin; natural product; pharmacological activity; determination;

【DOI】

【Funds】 National Natural Science Foundation of China (No. 81274195) Program for Liaoning Innovative Research Team in University by Department of Education in Liaoning Province (LT2013018) Research Fund for the Doctoral Program of Higher Education of China (20122105110004) Program for New Century Excellent Talents in University of Ministry of Education of China (NCET-11-1007)

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    References

    [1]Zhang W F,Liu B S.World Journal of Integrated Traditional and Western Medicine,2010,5(6):543.

    [2]Wang X P,Lu X.International Journal of Traditional Chinese Medicine,2004,26(3):138.

    [3]Hou J,He W H,Wang M X,et al.Hebei Medical Journal,2004,26(1):71.

    [4]Viviane S P,Alemandre T C,Taketa G G.Saponins and sapogenins from Brachiaria decumbens Staph[J].J Brazilian Chem Soc,2002,13 (2 ):135 .

    [5]Luo M,Shu J,Lu Y.Journal of Nanjing University of Traditional Chinese Medicine,2009,25 (4 ):318 .

    [6]Zhang L,Liu Y D.Journal of Southwest University of Science and Technology,2006,2 (21 ):88 .

    [7]Xie C X,Zuo C F,Bai Y,et al.Chinese Archives of Traditional Chinese Medicine,2012,30 (9 ):2016.

    [8]Sun J,Xiao P Y.Journal of Shaanxi College of Traditional Chinese Medicine,2010,33 (4 ):98 .

    [9]Zhang X F,Liu J Q.Central South Pharmacy,2012,10 (5 ):321 .

    [10]Yoon K D,Chin Y W,Yang M H,et al.Application of highspeed countercurrent chromatography-evaporative light scattering detection for the separation of seven steroidal saponins from Dioscorea villosa[J].Phytochem Anal,2012,23 (5 ):462 .

    [11]Yoon K D,Kim J.Preparative separation of dioscin derivatives from Dioscorea villosa by centrifugal partition chromatography coupled with evaporative light scattering detection[J].J Sep Sci,2008,31 (13 ):2486.

    [12]Xiao X H,Yuan Z Q,Li G K.Separation and purification of steroidal saponins from Paris polyphylla by microwave-assisted extraction coupled with countercurrent chromatography using evaporative light scattering detection[J].J Sep Sci,2014,37 (6 ):635 .

    [13]Yin L H,Xu Y W,Qi Y,et al.A green and efficient protocol for industrial-scale preparation of dioscin from Dioscorea nipponica Makino by two-step macroporous resin column chromatography[J].Chem Eng J,2010,165 (1 ):281 .

    [14]Deng S J,Yu B,Hui Y.A facile synthetic approach to a group of structurally typical diosgenyl saponins[J].Tetrahedron Lett,1998,39 (36 ):6511.

    [15]Bi S R,Zhang Z F,Su C R.Natural Product Research and Development,1997,9 (4 ):1 .

    [16]Nakamura T,Komori C,Ejima A.Cytotoxic activities of solanum steroidal glycosides[J].Biol Pharm Bull,1996,19 (4 ):564 .

    [17]Park H J,Kwon S H,Lee J H.Kalopanaxsaponin A is a basic saponin structure for the antitumor activity of hederagenin monodesmosides[J].Planta Med,2001,67 (2 ):118 .

    [18]Zhu S,Zhang Y,Li M,et al.Synthesis and cytotoxicities of dioscin derivatives with decorated chacotriosyl residues[J].Bioorg Med Chem Lett,2006,16 (21 ):5629.

    [19]Li W,Qiu Z Z,Wang Y B,et al.Synthesis,cytotoxicity,and hemolytic activity of 6'-O-substituted dioscin derivatives[J].Carbohyd Res,2007,342 (18 ):2705.

    [20]Wang Y H,Kang A L,Fan B J,et al.Chinese Journal of Pharmaceutical Analysis,2009,29 (5 ):739 .

    [21]Li K M,Dong Y,Zhang Y W.Chinese Journal of Pharmaceutical Analysis,2004,24 (6 ):640.

    [22]Liu C Z,Zhou H Y,Yan Q.Fingerprint analysis of Dioscorea nipponica by high-performance liquid chromatography with evaporative light scattering detection[J].Anal Chim Acta,2007,582 (1 ):61 .

    [23]Kwon H J,Choi S H,Yoo C S,et al.Development of an analytical method for yam saponins using HPLC with pulsed amperometric detection at different column temperatures[J].J Sep Sci,2013,36 (4 ):690 .

    [24]Qing L S,Shan X Q,Xu X M,et al.Rapid probe and isolation of bioactive compounds from Dioscorea panthaica using human serum albumin functionalized magnetic nano-particles(HSAMNPs)-based ligand fishing coupled with electrospray ionization mass spectrometry[J].Rapid Commun Mass Spectrom,2010,24 (22 ):3335.

    [25]Li K M,Chen Y W,Guo J Z,et al.Journal of China-Japan Friendship Hospital,2005,19 (3 ):188 .

    [26]Li F L,Zuo H X,Wang W.Jilin Journal of Traditional Chinese Medicine,2007,27 (4 ):58 .

    [27]Yuan C Q,Chen Z X.China Pharmaceuticals,2011,20 (2 ):34 .

    [28]Cheng X L,Qi L W,Wang Q,et al.Highly efficient sample preparation and quantification of constituents from traditional Chinese herbal medicines using matrix solid-phase dispersion extraction and UPLC-MS/MS[J].Analyst,2013,138 (8 ):2279.

    [29]Li K,Tang Y B,Fawcett J P,et al.Characterization of the pharmacokinetics of dioscin in rat[J].Steroids,2005,70 (8 ):525 .

    [30]Wang B,Ji S,Zhang H,et al.Liquid chromatography tandem mass spectrometry in study of the pharmacokinetics of six steroidal saponins in rats[J].Steroids,2013,78 (12 -13):1164.

    [31]Zhang A,Wang C,Liu Q,et al.Involvement of organic aniontransporting polypeptides in the hepatic uptake of dioscin in rat and human[J].Drug Metab Dispos,2013,41 (5 ):994 .

    [32]Wang L,Meng Q,Wang C,et al.Dioscin restores the activity of the anticancer agent adriamycin in multidrug-resistant human leukemia K562/adriamycin cells by down-regulating MDR1 via a mechanism involving NF-κB signaling inhibition[J].J Nat Prod,2013,76 (5 ):909 .

    [33]Wang L,Wang C,Peng J,et al.Dioscin enhances methotrexate absorption by down-regulating MDR1 in vitro and in vivo[J].Toxicol Appl Pharmacol,2014,277 (2 ):146 .

    [34]Zhang N,Zhang J,Li Z L,et alChinese Journal of Integrative Medicine on Cardio-/Cerebrovascular Disease,2009,7 (3 ):255 .

    [35]Yang R F,Pan W,Zhang G,et al.Chinese Journal of Integrative Medicine on Cardio-/Cerebrovascular Disease,2005,3 (1 ):14 .

    [36]Ma H Y,Zhao Z T,Wang L J.China Journal of Chinese Materia Medica,2002,27 (7 ):528 .

    [37]Kamisako T,Ogawa H.Regulation of biliary cholesterol secretion is associated with abcg5 and bcg S expressions in the rats:efects of diosgenin and ethinyl estradiol[J].Hepatol Res,2003,26 (4 ):348 .

    [38]Hu M M,Xu L N,Yin L H,et al.Cytotoxicity of dioscin in human gastric carcinoma cells through death receptor and mitochondrial pathways[J].J Appl Toxicol,2013,33 (8 ):712 .

    [39]Gao L L,Li F R,Jiao P,et al.Apoptosis of human ovarian cancer cells induced by Paris chinensis dioscin via a Ca(2 +)-mediated mitochondrion pathway[J].Asian Pac J Cancer Prev,2011,12 (5 ):1361.

    [40]Li Z F,Ning Z,Zhou Y.Guangxi Medical Journal,2012,34 (3 ):272 .

    [41]Gao Z J,Chen X Y,Liu J T,et al.Chinese Journal of Information on Traditional Chinese Medicine,2005,12 (7 ):33 .

    [42]Cai J,Ju Y,Liu J M.Chinese Traditional and Herbal Drugs,2001,32 (Supplement):94 .

    [43]Wang Z,Cheng Y,Wang N,et al.Dioscin induces cancer cell apoptosis through elevated oxidative stress mediated by downregulation of peroxiredoxins[J].Cancer Biol Ther,2012,13 (3 ):138 .

    [44]Hsieh M J,Tsai T L,Hsieh Y S,et al.Dioscin-induced autophagy mitigates cell apoptosis through modulation of PI3K/Akt and ERK and JNK signaling pathways in human lung cancer cell lines[J].Arch Toxicol,2013,87 (11 ):1927.

    [45]Sun B T,Zheng L H,Bao Y L,et al.Reversal effect of dioscin on multidrug resistance in human hepatoma Hep G2/adriamycin cells[J].Eur J Pharm,2011,654 (2 ):129.

    [46]Wang Y,Che C M,Chiu J F,et al.Dioscin(saponin)-induced generation of reactive oxygen species through mitochondria dysfunction:a proteomic-based study[J].J Proteome Res,2007,6 (12 ):4703.

    [47]Zhang L H,Zhang Z S,Li C D,et al.Lishizhen Medicine and Materia Medica Research,2012,23 (5 ):1116.

    [48]Lu B N,Xu Y,Xu L,et al.Mechanism investigation of dioscin against CCl4 -induced acute liver damage in mice[J].Environ Toxicol Pharm,2012,34 (2 ):127 .

    [49]Zhao X M,Cong X N,Zheng L,et al.Dioscin,a natural steroid saponin,shows remarkable protective effect against acetaminophen-induced liver damage in vitro and in vivo[J].Toxicology Lett,2012,214 (1 ):69.

    [50]Ma M H,Wu X H,He Y,et al.Journal of Sichuan Agricultural University,2011,42 (4 ):494.

    [51]Xie S J,Song H R,Peng X R.Journal of Sichuan of Traditional Chinese Medicine,2007,25 (8 ):10 .

    [52]Liu C,Wang Y,Wu C,et al.Dioscin's antiviral effect in vitro[J].Virus Res,2013,172 (1 -2):9 .

    [53]Turchan J,Pocernich C B,Gairola C,et al.Oxidative stress in HIV demented patients and protection ex vivo with novel antioxidants[J].Neurology,2003,60 (2 ):307 .

    [54]Xu T T,Zhang S,Zheng L L,et al.A 90-day subchronic toxicological assessment of dioscin,a natural steroid saponin,in Sprague-Dawley rats[J].Food Chem Toxicol,2012,50 (5 ):1279.

This Article

ISSN:1001-5302

CN: 11-2272/R

Vol 40, No. 01, Pages 36-41

January 2015

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Knowledge

Abstract

  • 1 Chemical research
  • 2 Dioscin metabolisms
  • 3 Dioscin pharmacodynamics and molecular mechanism
  • 4 Dioscin toxicology
  • 5 Prospect
  • References