spirostans

Summary

Summary: Cholestane derivatives containing a fused lactone ring at the 16,17-position and a spiroglycosidic linkage at C-22. Members include sarsaponin, DIOSGENIN and yamogenin.

Top Publications

  1. Fu Y, Yu Z, Tang X, Zhao Y, Yuan X, Wang S, et al. Pennogenin glycosides with a spirostanol structure are strong platelet agonists: structural requirement for activity and mode of platelet agonist synergism. J Thromb Haemost. 2008;6:524-33 pubmed publisher
    ..var. yunnanensis in promoting hemostasis in vivo. Their mode of their action on platelets suggests that they represent a new type of platelet agonist. ..
  2. Ma D, Zhang J, Sugahara K, Sagara Y, Kodama H. Effect of sarsasapogenin and its derivatives on the stimulus coupled responses of human neutrophils. Clin Chim Acta. 2001;314:107-12 pubmed
    ..Of the sapogenins tested, sarsasapogenin may have the most clinical use as it suppresses superoxide generation. ..
  3. Bao W, Pan H, Lu M, Ni Y, Zhang R, Gong X. The apoptotic effect of sarsasapogenin from Anemarrhena asphodeloides on HepG2 human hepatoma cells. Cell Biol Int. 2007;31:887-92 pubmed
    ..Flow cytometry analysis showed that sarsasapogenin-induced cell apoptosis was through arrest of cell cycle in G(2)/M phase. Hence we proposed that sarsasapogenin could be used as an anti-liver cancer drug for future studies...
  4. Liu N, Wen X, Liu J, Liang M, Zeng H, Lin Y, et al. Determination of ruscogenin in crude Chinese medicines and biological samples by immunoassay. Anal Bioanal Chem. 2006;386:1727-33 pubmed
    ..The assay was successfully used for the measurement of ruscogenin concentrations in crude Chinese medicines and in biological samples from a pharmacokinetics study of ruscogenin...
  5. Ren L, Luo Y, Li X, Zuo D, Wu Y. Antidepressant-like effects of sarsasapogenin from Anemarrhena asphodeloides BUNGE (Liliaceae). Biol Pharm Bull. 2006;29:2304-6 pubmed
    ..Moreover, sarsasapogenin showed a monoamine oxidase inhibitory activity in the mouse brain. These findings suggest that the antidepressant activity of sarsasapogenin may involve the central monoaminergic neurotransmitter systems...
  6. Hu Y, Xia Z, Sun Q, Orsi A, Rees D. A new approach to the pharmacological regulation of memory: Sarsasapogenin improves memory by elevating the low muscarinic acetylcholine receptor density in brains of memory-deficit rat models. Brain Res. 2005;1060:26-39 pubmed
    ..Therefore, ZMS seems to represent a new approach to the pharmacological regulation of learning and memory and appears to be not simply palliative but may modify the progression of the disease. ..
  7. Yoon K, Kim J. Preparative separation of dioscin derivatives from Dioscorea villosa by centrifugal partition chromatography coupled with evaporative light scattering detection. J Sep Sci. 2008;31:2486-91 pubmed publisher
    ..9, 97.4, 99.2 and 99.5%, respectively. Their chemical structures were determined by spectroscopic data of ESI-MS, 1H NMR and 13C NMR and comparing with those of previously reported values. ..
  8. Candra E, Matsunaga K, Fujiwara H, Mimaki Y, Sashida Y, Yamakuni T, et al. Two steroidal saponins from Camassia cusickii induce L1210 cell death through the apoptotic mechanism. Can J Physiol Pharmacol. 2001;79:953-8 pubmed
    ..1 microM) are the most powerful apoptotic saponins known. These results suggest that TGHS-1 and TGHS-2 induce apoptotic cell death through caspase-3 activation. ..
  9. Acharya D, Mitaine Offer A, Kaushik N, Miyamoto T, Paululat T, Mirjolet J, et al. Cytotoxic spirostane-type saponins from the roots of Chlorophytum borivilianum. J Nat Prod. 2009;72:177-81 pubmed publisher
    ..The cytotoxicity of borivilianosides F (2), G (3), and H (4) and three known compounds was evaluated using two human colon cancer cell lines (HT-29 and HCT 116). ..

More Information

Publications62

  1. Valadares Y, Brandão a G, Kroon E, Filho J, Oliveira A, Braga F. Antiviral activity of Solanum paniculatum extract and constituents. Z Naturforsch C. 2009;64:813-8 pubmed
    ..8 +/- 1.7) microg/ml] and antivaccinia virus effects [EC50 = (177.0 +/- 3.3) microg/ml], with low cytotoxicity (CC50 > 400 microg/ml). The results corroborate Solanum paniculatum as a source of cytotoxic and antiviral compounds. ..
  2. Wang Q, Hou Q, Guo Z, Zou K, Xue Y, Huang N, et al. Three new steroidal glycosides from roots of Reineckia carnea. Nat Prod Res. 2013;27:85-92 pubmed publisher
    ..The structures of three new compounds were elucidated by spectroscopic methods including 1-D NMR, 2-D NMR and MS spectrums, and their anticancer activities were evaluated by MTT method. ..
  3. Zhang H, Sydara K, Tan G, Ma C, Southavong B, Soejarto D, et al. Bioactive constituents from Asparagus cochinchinensis. J Nat Prod. 2004;67:194-200 pubmed
    ..The structures were determined by spectroscopic and chemical methods...
  4. Mimaki Y, Kuroda M, Ide A, Kameyama A, Yokosuka A, Sashida Y. Steroidal saponins from the aerial parts of Dracaena draco and their cytostatic activity on HL-60 cells. Phytochemistry. 1999;50:805-13 pubmed
    ..The isolated saponins were evaluated for their cytostatic activity on leukemia HL-60 cells. ..
  5. Yoon K, Chin Y, Yang M, Choi J, Kim J. Application of high-speed countercurrent chromatography-evaporative light scattering detection for the separation of seven steroidal saponins from Dioscorea villosa. Phytochem Anal. 2012;23:462-8 pubmed publisher
    ..Subsquent normal-phase HSCCC of the spirostanol-rich extract led to the separation of four spirostanol saponins: zingiberensis saponin I (15.2?mg), deltonin (31.5?mg), dioscin (7.7?mg) and prosapogenin A of dioscin (3.4?mg). ..
  6. Nawłoka P, Kalinowska M, Paczkowski C, Wojciechowski Z. Evidence for essential histidine and dicarboxylic amino-acid residues in the active site of UDP-glucose : solasodine glucosyltransferase from eggplant leaves. Acta Biochim Pol. 2003;50:567-72 pubmed
    ..Reagents modifying serine and arginine residues have no effect on the enzyme activity. ..
  7. Liu J, Chen T, Yu B, Xu Q. Ruscogenin glycoside (Lm-3) isolated from Liriope muscari inhibits lymphocyte adhesion to extracellular matrix. J Pharm Pharmacol. 2002;54:959-65 pubmed
    ..These results suggest that the blockade of lymphocyte adhesion to extracellular matrix through interference with the protein kinase C pathway may be one of the mechanisms by which Lm-3 exerts anti-inflammatory activity...
  8. Huang X, Lin Y, Kong L. Steroids from the roots of Asparagus officinalis and their cytotoxic activity. J Integr Plant Biol. 2008;50:717-22 pubmed publisher
    ..Among them, eight compounds displayed significant cytotoxicities against human A2780, HO-8910, Eca-109, MGC-803, CNE, LTEP-a-2, KB and mouse L1210 tumor cells...
  9. You W, Zhou T, Ma Z, Liang Q, Xiao C, Tang X, et al. Ophiopogonin D maintains Ca2+ homeostasis in rat cardiomyocytes in vitro by upregulating CYP2J3/EETs and suppressing ER stress. Acta Pharmacol Sin. 2016;37:368-81 pubmed publisher
    ..OPD is a novel CYP2J3 inducer that may offer a therapeutic benefit in treatment of cardiovascular diseases related to disturbance of Ca(2+) homeostasis and ER stress. ..
  10. Ni Y, Gong X, Lu M, Chen H, Wang Y. Mitochondrial ROS burst as an early sign in sarsasapogenin-induced apoptosis in HepG2 cells. Cell Biol Int. 2008;32:337-43 pubmed publisher
    ..These findings show that a mitochondrial ROS burst is an early upstream apoptotic signal which may trigger the mitochondrial apoptotic pathway and play a vital role in sarsasapogenin-induced HepG2 cell apoptosis. ..
  11. Sharma P, Chauhan P, Dutt P, Amina M, Suri K, Gupta B, et al. A unique immuno-stimulant steroidal sapogenin acid from the roots of Asparagus racemosus. Steroids. 2011;76:358-64 pubmed publisher
    ..1 was tested against the type of immune responses generated during treatment in normal and immune-suppressed animals and detailed biological activity evaluation suggests it to be a potent immunostimulator. ..
  12. Qing L, Shan X, Xu X, Xue Y, Deng W, Li B, et al. Rapid probe and isolation of bioactive compounds from Dioscorea panthaica using human serum albumin functionalized magnetic nano-particles (HSA-MNPs)-based ligand fishing coupled with electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom. 2010;24:3335-9 pubmed publisher
  13. Wang B, Ji S, Zhang H, Zhao L, Lv L, Li Y, et al. Liquid chromatography tandem mass spectrometry in study of the pharmacokinetics of six steroidal saponins in rats. Steroids. 2013;78:1164-70 pubmed publisher
    ..polyphylla extract in Sprague-Dawley rats. ..
  14. Zhang R, Wang Z, Howson P, Zhou S, Wu E, Xia Z, et al. Smilagenin attenuates beta amyloid (25-35)-induced degeneration of neuronal cells via stimulating the gene expression of brain-derived neurotrophic factor. Neuroscience. 2012;210:275-85 pubmed publisher
  15. Yu H, Ma B, Kang L, Zhang T, Jiang F, Zhang J, et al. Saponins from the processed rhizomes of Polygonatum kingianum. Chem Pharm Bull (Tokyo). 2009;57:1011-4 pubmed
    ..Compounds 3 and 5 were first reported from the genus Polygonatum. Compounds 4, 6 and 7 are reported for the first time from the processed Polygonatum kingianum...
  16. Wu X, Wang L, Wang G, Wang H, Dai Y, Ye W, et al. New steroidal saponins and sterol glycosides from Paris polyphylla var. yunnanensis. Planta Med. 2012;78:1667-75 pubmed publisher
    ..2, 4.7, 11.1, and 2.7?µM, respectively...
  17. Pérez Labrada K, Méndez Y, Brouard I, Rivera D. Multicomponent ligation of steroids: creating diversity at the linkage moiety of bis-spirostanic conjugates by Ugi reactions. ACS Comb Sci. 2013;15:320-30 pubmed publisher
    ..Overall, the method comprises the rapid generation of molecular diversity at the bis-steroid linkage moiety and, consequently, shows promise toward the production of combinatorial libraries of bis-spirostanes for biological screening. ..
  18. Nakanishi T. [Search for and structural elucidation of medicinal products from the vegetable kingdom (crude drugs and plant materials)]. Yakugaku Zasshi. 2007;127:1975-96 pubmed
    ..terpenoids (mono-, sesqui-, di-, and triterpenoids), steroids, glycosides, saponins, tannins, phenylpropanoids, lignans, flavonoids (flavones, flavonols, flavanones, biflavones, flavan-3-ols, etc.), etc. are dealt with and referred to. ..
  19. Flåøyen A, Wilkins A, Deng D, Brekke T. Ovine metabolism of saponins: evaluation of a method for estimating the ovine uptake of steroidal saponins from Narthecium ossifragum. Vet Res Commun. 2001;25:225-38 pubmed
    ..The absorption of free sapogenins appeared to occur in the jejunum. The concentration of sapogenins in faeces reached a plateau 108 h after dosing started. ..
  20. Aquino R, Conti C, De Simone F, Orsi N, Pizza C, Stein M. Antiviral activity of constituents of Tamus communis. J Chemother. 1991;3:305-9 pubmed
    ..The results were of some interest mainly for the phenanthrene derivatives. ..
  21. Nakata N, Tokudome A, Yanai H, Nohara T. Conversion of spirostane and solanidane into pregnane (1)introduction of oxygen function into C-23. Chem Pharm Bull (Tokyo). 2012;60:150-3 pubmed
    ..However, in solasodine, we obtained a 23-nitroso derivative by the reaction in AcOH and 23,24-bisnorcholanic acid 22-16 lactone, or vespertilin, in AcOH and CHCl(3). ..
  22. Cammarata A, Upadhyay S, Jursic B, Neumann D. Antifungal activity of 2?,3?-functionalized steroids stereoselectively increases with the addition of oligosaccharides. Bioorg Med Chem Lett. 2011;21:7379-86 pubmed publisher
  23. Ji H, Ding X, Tao G. [Screening of steroidal saponins from the bulbs of Lilium brownii var. colchesteri by combination of high performance liquid chromatography-electrospray ionization mass spectrometry and electron impact mass spectrometry]. Se Pu. 2001;19:403-6 pubmed
    ..The combination of HPLC/ESI-MS and EI-MS is well suitable for rapidly screening steroidal saponins from plants. ..
  24. Eskander J, Lavaud C, Harakat D. Steroidal saponins from the leaves of Agave macroacantha. Fitoterapia. 2010;81:371-4 pubmed publisher
    ..The (1)H and (13)C resonances of the four compounds were assigned using a combination of 1D and 2D NMR techniques including (1)H, (13)C, COSY, TOCSY, ROESY, HSQC and HMBC NMR and confirmed by mass spectrometry. ..
  25. Upadhyay S, Creech C, Bowdy K, Stevens E, Jursic B, Neumann D. Synthesis and antifungal activity of functionalized 2,3-spirostane isomers. Bioorg Med Chem Lett. 2011;21:2826-31 pubmed publisher
  26. Hu H, Zhang R, Zhang Y, Xia Z, Hu Y. Role of CREB in the regulatory action of sarsasapogenin on muscarinic M1 receptor density during cell aging. FEBS Lett. 2010;584:1549-52 pubmed publisher
    ..Furthermore, the results support the hypothesis that pCREB regulates M(1) receptor gene expression through heterodimer formation. ..
  27. Xiang L, Wang Y, Yi X, Zheng G, He X. Bioactive spirostanol saponins from the rhizome of Tupistra chinensis. Steroids. 2016;108:39-46 pubmed publisher
    ..7. Compounds 2 and 12 showed significant inhibition on NO production with IC50 values of 16.1±1.8 and 13.5±1.2 μM, respectively. ..
  28. Li Y, Hu L, Lou F, Hong J, Li J, Shen Q. Furostanoside from Asparagus filicinus. J Asian Nat Prod Res. 2005;7:43-7 pubmed
    ..The structure of 1 has been elucidated on the basis of spectral data. ..
  29. Macias Alonso M, Flores Alamo M, Iglesias Arteaga M. On the reactivity of 23-methoxycarbonyl furospirostanes. Steroids. 2011;76:1021-31 pubmed publisher
  30. Yada H, Kimura T, Suzuki M, Ohnishi Kameyama M, Shinmoto H. New steroidal saponin from Hosta sieboldiana. Biosci Biotechnol Biochem. 2010;74:861-4 pubmed
  31. Hernández Linares M, Sandoval Ramírez J, Meza Reyes S, Montiel Smith S, Fernández Herrera M, Bernès S. Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes. Steroids. 2010;75:240-4 pubmed publisher
    ..In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields. ..
  32. Lu Y, Luo J, Xu D, Huang X, Kong L. Characterization of spirostanol saponins in Solanum torvum by high-performance liquid chromatography/evaporative light scattering detector/electrospray ionization with multi-stage tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008;22:2447-52 pubmed publisher
  33. Lin J, Chang Y, Lu M, Yang D. Simultaneous Determination of Furostanol, Pennogenyl, and Diosgenyl Glycosides in Taiwanese Rhizoma Paridis ( Paris formosana Hayata) by high-performance liquid chromatography with evaporative light scattering detection. J Agric Food Chem. 2011;59:1587-93 pubmed publisher
    ..04-0.90 ?g, respectively, for these saponins. Moreover, 203 nm UV detection was also used for comparison. The saponins in P. formosana Hayata gathered from various areas of Taiwan were determined by applying the established method. ..
  34. De Marino S, Festa C, Zollo F, Iorizzi M. Novel steroidal components from the underground parts of Ruscus aculeatus L. Molecules. 2012;17:14002-14 pubmed publisher
    ..along with four known furostanol and one spirostanol saponins 5–9 and three free sterols. All of the structures have been elucidated on the basis of spectroscopic data 1D and 2D NMR experiments, MS spectra and GC analyses...
  35. González M, Zamilpa A, Marquina S, Navarro V, Alvarez L. Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships. J Nat Prod. 2004;67:938-41 pubmed
    ..rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed. ..
  36. Li M, Yu B. Facile conversion of spirostan saponin into furostan saponin: synthesis of methyl protodioscin and its 26-thio-analogue. Org Lett. 2006;8:2679-82 pubmed
    ..reaction: see text] A facile approach for the conversion of a spirostan saponin into its furostan counterpart, as illustrated by the transformation of dioscin to methyl protodioscin (and its 26-thio-analogue), has been developed. ..
  37. Berglöf E, Plantman S, Johansson S, Stromberg I. Inhibition of proteoglycan synthesis affects neuronal outgrowth and astrocytic migration in organotypic cultures of fetal ventral mesencephalon. J Neurosci Res. 2008;86:84-92 pubmed
    ..To conclude, inhibition of PG synthesis affects glial-associated TH-positive nerve fiber formation in ventral mesencephalic cultures, which might be an indirect effect of impaired astrocytic migration. ..
  38. Ohno M, Murakami K, El Aasr M, Zhou J, Yokomizo K, Ono M, et al. New spirostanol glycosides from Solanum nigrum and S. jasminoides. J Nat Med. 2012;66:658-63 pubmed publisher
    ..jasminoides. ..
  39. Lee B, Trinh H, Jung K, Han S, Kim D. Inhibitory effects of steroidal timosaponins isolated from the rhizomes of Anemarrhena asphodeloides against passive cutaneous anaphylaxis reaction and pruritus. Immunopharmacol Immunotoxicol. 2010;32:357-63 pubmed publisher
    ..On the basis of these findings, antiallergic effect of AA may be due to those of its steroidal constituents, and that of timosaponin AIII may be activated by using intestinal microflora...
  40. Zhang L, Liu J, Xu L, Yang S. Chantriolide C, a new withanolide glucoside and a new spirostanol saponin from the rhizomes of Tacca chantrieri. Chem Pharm Bull (Tokyo). 2009;57:1126-8 pubmed
    ..The structures of the new saponins were determined by detailed analysis of their 1 dimensional (1D) and 2D NMR spectra, and chemical evidences...
  41. López Y, Santillan R, Farfán N. New bisfuran derivative from sarsasapogenin. An X-ray and NMR analysis. Steroids. 2006;71:12-7 pubmed
  42. Ali Z, Smillie T, Khana I. 7-Oxodioscin, a new spirostan steroid glycoside from the rhizomes of Dioscorea nipponica. Nat Prod Commun. 2013;8:319-21 pubmed
  43. Wang Y, Zhang Y, Yu B. The cytotoxicity of saponins correlates with their cellular internalization. ChemMedChem. 2007;2:288-91 pubmed
  44. Lee C, Hwang T, He W, Tsai Y, Yen C, Yen H, et al. Anti-neutrophilic inflammatory steroidal glycosides from Solanum torvum. Phytochemistry. 2013;95:315-21 pubmed publisher
    ..66 and 3.59 ?M, while two others inhibited both inflammatory mediators with IC50 values of 0.66-3.49 ?M. Structure-activity relationships are discussed...
  45. Shu D, Qing Y, Tong Q, He Y, Xing Z, Zhao Y, et al. Deltonin isolated from Dioscorea zingiberensis inhibits cancer cell growth through inducing mitochondrial apoptosis and suppressing Akt and mitogen activated protein kinase signals. Biol Pharm Bull. 2011;34:1231-9 pubmed
  46. Sidiq T, Khajuria A, Suden P, Singh S, Satti N, Suri K, et al. A novel sarsasapogenin glycoside from Asparagus racemosus elicits protective immune responses against HBsAg. Immunol Lett. 2011;135:129-35 pubmed publisher
    ..Effect of immunoside on red blood cell haemolysis was determined. The results have suggested that immunoside potentially enhanced anti-HBsAg immune response via augmenting Th1/Th2 response in a dose dependent manner...
  47. Zhang S, He Y, Tong Q, Chen Q, Wu X, Huang W. Deltonin induces apoptosis in MDA?MB?231 human breast cancer cells via reactive oxygen species?mediated mitochondrial dysfunction and ERK/AKT signaling pathways. Mol Med Rep. 2013;7:1038-44 pubmed publisher
    ..Therefore, deltonin may be a potential chemotherapeutic agent for the treatment of breast cancer. ..
  48. Zou C, Hou S, Shi Y, Lei P, Liang X. The synthesis of gracillin and dioscin: two typical representatives of spirostanol glycosides. Carbohydr Res. 2003;338:721-7 pubmed
    ..A procedure using guanidine for the selective deblocking of acetyl while retaining benzoyl protecting groups is described. ..
  49. Nguyen V, Darbour N, Bayet C, Doreau A, Raad I, Phung B, et al. Selective modulation of P-glycoprotein activity by steroidal saponines from Paris polyphylla. Fitoterapia. 2009;80:39-42 pubmed publisher
    ..By contrast to a weak efficiency on BCRP, the three saponins displayed significant effects as inhibitors of P-glycoprotein-mediated drug efflux. ..
  50. Wang K, Ju X, Zhang L, Wang W, Shen L. [A novel C27-steroidal glycoside sulfate from Liriope graminifolia]. Yao Xue Xue Bao. 2012;47:619-23 pubmed
    ..Compound 1 has cytotoxic activities against K562 and HL60 cells with IC50 values of 18.6 microg x mL(-1) and 16.5 microg x mL(-1), respectively...
  51. Barile E, Zolfaghari B, Sajjadi S, Lanzotti V. Saponins of Allium elburzense. J Nat Prod. 2004;67:2037-42 pubmed
    ..The reported compounds have been isolated in large amounts, and this makes A. elburzense a prolific producer of saponins of the furostanol and spirostanol types...
  52. Sa F, Gao J, Fung K, Zheng Y, Lee S, Wang Y. Anti-proliferative and pro-apoptotic effect of Smilax glabra Roxb. extract on hepatoma cell lines. Chem Biol Interact. 2008;171:1-14 pubmed
    ..These results have identified, for the first time, the biological activity of SGRE in HepG2 and Hep3B cells and should lead to further development of SGR for liver disease therapy...
  53. Xia C, Sun J, Hao H, Wang G, Yan B, Gu S, et al. Quantitative determination of ophiopogonin d by liquid chromatography/electrospray ionization mass spectrometry and its pharmacokinetics in rat. Planta Med. 2008;74:1832-6 pubmed publisher
    ..007 +/- 0.002 L/min/kg) for the latter formulation, consistent with an inhibition by one or more other components in the formulation...