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Volumn 71, Issue , 2014, Pages 137-226

Chemical synthesis of saponins

Author keywords

Glycoside; Glycosylation; Protecting groups; Saponin; Steroid; Triterpene

Indexed keywords

AGLYCONE; ARABINOSE; CANDICANOSIDE A; CARBOHYDRATE; CARDENOLIDE; CHIKUSETSU SAPONIN; CHOLESTAN; CIWUJIANOSIDE C3; DAMMARANE DERIVATIVE; DIGITOXIN; FUROSTAN; LUPANE; OLEANANE; OLEANOLIC ACID; OSLADIN; OUABAIN; PAVONININ 4; POLYPHYLLIN D; QS 21; RHODEXIN A; SAPONIN DERIVATIVE; SARSASAPOGENIN; SPIROSTAN DERIVATIVE; STEROID; TETRABUTYLAMMONIUM; TIGOGENIN TRIGLYCOSIDE; TIMOSAPONIN; TRITERPENE; UNCLASSIFIED DRUG; UNINDEXED DRUG; URSANE; GLYCOSIDE; PLANT EXTRACT; POLYSACCHARIDE; SAPONIN;

EID: 84918830000     PISSN: 00652318     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-800128-8.00002-9     Document Type: Chapter
Times cited : (76)

References (290)
  • 1
    • 0004108162 scopus 로고
    • Cambridge University Press, Cambridge, UK
    • Hostettmann K., Marston A. Saponins 1995, Cambridge University Press, Cambridge, UK.
    • (1995) Saponins
    • Hostettmann, K.1    Marston, A.2
  • 2
    • 0035003037 scopus 로고    scopus 로고
    • Advances in structural determination of saponins and terpenoid glycosides
    • Sahu N.P., Achari B. Advances in structural determination of saponins and terpenoid glycosides. Curr. Org. Chem. 2001, 5:315-334.
    • (2001) Curr. Org. Chem. , vol.5 , pp. 315-334
    • Sahu, N.P.1    Achari, B.2
  • 3
    • 0037118920 scopus 로고    scopus 로고
    • Chromatographic determination of plant saponins
    • Oleszek W.A. Chromatographic determination of plant saponins. J. Chromatogr. A 2002, 967:147-162.
    • (2002) J. Chromatogr. A , vol.967 , pp. 147-162
    • Oleszek, W.A.1
  • 4
    • 4344587843 scopus 로고    scopus 로고
    • Biological activities and distribution of plant saponins
    • Sparg S.G., Light M.E., van Staden J. Biological activities and distribution of plant saponins. J. Ethnopharmacol. 2004, 94:219-243.
    • (2004) J. Ethnopharmacol. , vol.94 , pp. 219-243
    • Sparg, S.G.1    Light, M.E.2    van Staden, J.3
  • 5
    • 33846219958 scopus 로고    scopus 로고
    • Saponins, classification and occurrence in the plant kingdom
    • Vincken J.-P., Heng L., de Groot A., Gruppen H. Saponins, classification and occurrence in the plant kingdom. Phytochemistry 2007, 68:275-297.
    • (2007) Phytochemistry , vol.68 , pp. 275-297
    • Vincken, J.-P.1    Heng, L.2    de Groot, A.3    Gruppen, H.4
  • 6
    • 62649109381 scopus 로고    scopus 로고
    • Cytotoxic asterosaponins capable of promoting polymerization of tubulin from the starfish Culcita novaeguineae
    • Tang H.-F., Cheng G., Wu J., Chen X.-L., Zhang S.-Y., Wen A.-D., Lin H.-W. Cytotoxic asterosaponins capable of promoting polymerization of tubulin from the starfish Culcita novaeguineae. J. Nat. Prod. 2009, 72:284-289.
    • (2009) J. Nat. Prod. , vol.72 , pp. 284-289
    • Tang, H.-F.1    Cheng, G.2    Wu, J.3    Chen, X.-L.4    Zhang, S.-Y.5    Wen, A.-D.6    Lin, H.-W.7
  • 7
    • 76149086185 scopus 로고    scopus 로고
    • Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean
    • Van Dyck S., Gerbaux P., Flammang P. Qualitative and quantitative saponin contents in five sea cucumbers from the Indian ocean. Mar. Drugs 2010, 8:173-189.
    • (2010) Mar. Drugs , vol.8 , pp. 173-189
    • Van Dyck, S.1    Gerbaux, P.2    Flammang, P.3
  • 8
    • 0002705849 scopus 로고    scopus 로고
    • Saponins and plant defence-A soap story
    • Osbourn A. Saponins and plant defence-A soap story. Trends Plant Sci. 1996, 1:4-9.
    • (1996) Trends Plant Sci. , vol.1 , pp. 4-9
    • Osbourn, A.1
  • 10
    • 0037158709 scopus 로고    scopus 로고
    • A saponin-detoxifying enzyme mediates suppression of plant defences
    • Bouarab K., Melton R., Peart J., Baulcombe D., Osbourn A. A saponin-detoxifying enzyme mediates suppression of plant defences. Nature 2002, 418:889-892.
    • (2002) Nature , vol.418 , pp. 889-892
    • Bouarab, K.1    Melton, R.2    Peart, J.3    Baulcombe, D.4    Osbourn, A.5
  • 11
    • 65649154085 scopus 로고    scopus 로고
    • Plant-microbe interactions: Chemical diversity in plant defense
    • Bednarek P., Osbourn A. Plant-microbe interactions: Chemical diversity in plant defense. Science 2009, 324:746-748.
    • (2009) Science , vol.324 , pp. 746-748
    • Bednarek, P.1    Osbourn, A.2
  • 13
    • 0034521898 scopus 로고    scopus 로고
    • The bioactivity of saponins: Triterpenoid and steroidal glycosides
    • Rao A.V., Gurfinkel D.M. The bioactivity of saponins: Triterpenoid and steroidal glycosides. Drug Metabol. Drug Interact. 2000, 17:211-235.
    • (2000) Drug Metabol. Drug Interact. , vol.17 , pp. 211-235
    • Rao, A.V.1    Gurfinkel, D.M.2
  • 15
    • 80052059686 scopus 로고    scopus 로고
    • The saponins-Polar isoprenoids with important and diverse biological activities
    • Osbourn A., Goss R.J.M., Field R.A. The saponins-Polar isoprenoids with important and diverse biological activities. Nat. Prod. Rep. 2011, 28:1261-1268.
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 1261-1268
    • Osbourn, A.1    Goss, R.J.M.2    Field, R.A.3
  • 16
    • 0003697253 scopus 로고    scopus 로고
    • Saponins Used in Traditional and Modern Medicine
    • Plenum Press, New York, G.R. Waller, K. Yamasaki (Eds.)
    • Saponins Used in Traditional and Modern Medicine. Advances in Experimental Medicine and Biology 1996, Vol. 404. Plenum Press, New York. G.R. Waller, K. Yamasaki (Eds.).
    • (1996) Advances in Experimental Medicine and Biology , vol.404
  • 17
    • 0031774970 scopus 로고    scopus 로고
    • Some progress on chemical studies of triterpenoid saponins from Chinese medicinal plants
    • Qin G.-W. Some progress on chemical studies of triterpenoid saponins from Chinese medicinal plants. Curr. Org. Chem. 1998, 2:613-625.
    • (1998) Curr. Org. Chem. , vol.2 , pp. 613-625
    • Qin, G.-W.1
  • 18
    • 0035992781 scopus 로고    scopus 로고
    • Traditional Chinese medicine (TCM): Are polyphenols and saponins the key ingredients triggering biological activities?
    • Liu J., Henkel T. Traditional Chinese medicine (TCM): Are polyphenols and saponins the key ingredients triggering biological activities?. Curr. Med. Chem. 2002, 9:1483-1485.
    • (2002) Curr. Med. Chem. , vol.9 , pp. 1483-1485
    • Liu, J.1    Henkel, T.2
  • 20
    • 0034002325 scopus 로고    scopus 로고
    • Isolation of the pharmacologically active saponin ginsenoside Rb1 from ginseng by immunoaffinity column chromatography
    • Fukuda N., Tanaka H., Shoyama Y. Isolation of the pharmacologically active saponin ginsenoside Rb1 from ginseng by immunoaffinity column chromatography. J. Nat. Prod. 2000, 63:283-285.
    • (2000) J. Nat. Prod. , vol.63 , pp. 283-285
    • Fukuda, N.1    Tanaka, H.2    Shoyama, Y.3
  • 21
    • 0034127877 scopus 로고    scopus 로고
    • Saponins isolated from Allium chinense G. Don and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug
    • Baba M., Ohmura M., Kishi N., Okada Y., Shibata S., Peng J., Yao S.-S., Nishino H., Okuyama T. Saponins isolated from Allium chinense G. Don and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug. Biol. Pharm. Bull. 2000, 23:660-662.
    • (2000) Biol. Pharm. Bull. , vol.23 , pp. 660-662
    • Baba, M.1    Ohmura, M.2    Kishi, N.3    Okada, Y.4    Shibata, S.5    Peng, J.6    Yao, S.-S.7    Nishino, H.8    Okuyama, T.9
  • 22
    • 61349084783 scopus 로고    scopus 로고
    • Advances in saponin-based adjuvants
    • Sun H.X., Xie Y., Ye Y.P. Advances in saponin-based adjuvants. Vaccine 2009, 27:1787-1796.
    • (2009) Vaccine , vol.27 , pp. 1787-1796
    • Sun, H.X.1    Xie, Y.2    Ye, Y.P.3
  • 23
    • 33947415314 scopus 로고    scopus 로고
    • Saponins: Properties, applications and processing
    • Guclu-Ustundag O., Mazza G. Saponins: Properties, applications and processing. Crit. Rev. Food Sci. Nutr. 2007, 47:231-258.
    • (2007) Crit. Rev. Food Sci. Nutr. , vol.47 , pp. 231-258
    • Guclu-Ustundag, O.1    Mazza, G.2
  • 25
    • 79952900480 scopus 로고    scopus 로고
    • Molecular activities, biosynthesis and evolution of triterpenoid saponins
    • Augustin J.M., Kuzina V., Andersen S.B., Bak S. Molecular activities, biosynthesis and evolution of triterpenoid saponins. Phytochemistry 2011, 72:435-457.
    • (2011) Phytochemistry , vol.72 , pp. 435-457
    • Augustin, J.M.1    Kuzina, V.2    Andersen, S.B.3    Bak, S.4
  • 27
    • 0034872489 scopus 로고    scopus 로고
    • Glycosides in medicine: The role of glycosidic residue in biological activity
    • Kren V., Martinkova L. Glycosides in medicine: The role of glycosidic residue in biological activity. Curr. Med. Chem. 2001, 8:1303-1328.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1303-1328
    • Kren, V.1    Martinkova, L.2
  • 28
    • 0031127564 scopus 로고    scopus 로고
    • The role of carbohydrates in biologically active natural products
    • Weymouth-Wilson A.C. The role of carbohydrates in biologically active natural products. Nat. Prod. Rep. 1997, 14:99-110.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 99-110
    • Weymouth-Wilson, A.C.1
  • 30
    • 12044254693 scopus 로고
    • Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes
    • Abe I., Rohmer M., Prestwich G.C. Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem. Rev. 1993, 93:2189-2206.
    • (1993) Chem. Rev. , vol.93 , pp. 2189-2206
    • Abe, I.1    Rohmer, M.2    Prestwich, G.C.3
  • 31
    • 33751524122 scopus 로고    scopus 로고
    • Structure-activity relationships of oleanane- and ursane-type triterpenoids
    • Sun H., Fang W.-S. Structure-activity relationships of oleanane- and ursane-type triterpenoids. Bot. Stud. 2006, 47:339-368.
    • (2006) Bot. Stud. , vol.47 , pp. 339-368
    • Sun, H.1    Fang, W.-S.2
  • 32
    • 0001363322 scopus 로고    scopus 로고
    • Chemical synthesis of bioactive steroidal saponins
    • Marcel Dekker, New York, P. Wang, C.R. Bertozzi (Eds.)
    • Yu B., Hui Y. Chemical synthesis of bioactive steroidal saponins. Glycochemistry: Principles, Synthesis and Application 2001, 167-174. Marcel Dekker, New York. P. Wang, C.R. Bertozzi (Eds.).
    • (2001) Glycochemistry: Principles, Synthesis and Application , pp. 167-174
    • Yu, B.1    Hui, Y.2
  • 33
    • 84865345061 scopus 로고    scopus 로고
    • Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods
    • Yu B., Sun J., Yang X. Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods. Acc. Chem. Res. 2012, 45:1227-1236.
    • (2012) Acc. Chem. Res. , vol.45 , pp. 1227-1236
    • Yu, B.1    Sun, J.2    Yang, X.3
  • 34
    • 33751021311 scopus 로고    scopus 로고
    • CRC, Boca Raton, FL, D.E. Levy, P. Fügedi (Eds.)
    • The Organic Chemistry of Sugars 2006, CRC, Boca Raton, FL. D.E. Levy, P. Fügedi (Eds.).
    • (2006) The Organic Chemistry of Sugars
  • 35
    • 61849111654 scopus 로고    scopus 로고
    • New principles for glycoside-bond formation
    • Zhu X., Schmidt R.R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. Engl. 2009, 48:1900-1934.
    • (2009) Angew. Chem. Int. Ed. Engl. , vol.48 , pp. 1900-1934
    • Zhu, X.1    Schmidt, R.R.2
  • 36
    • 2542475310 scopus 로고    scopus 로고
    • The glycosylation of steroids
    • Pellissier H. The glycosylation of steroids. Tetrahedron 2004, 60:5123-5162.
    • (2004) Tetrahedron , vol.60 , pp. 5123-5162
    • Pellissier, H.1
  • 37
    • 35848954322 scopus 로고    scopus 로고
    • Carbohydrate chemistry in the total synthesis of saponins
    • Yu B., Zhang Y., Tang P. Carbohydrate chemistry in the total synthesis of saponins. Eur. J. Org. Chem. 2007, 5145-5161.
    • (2007) Eur. J. Org. Chem. , pp. 5145-5161
    • Yu, B.1    Zhang, Y.2    Tang, P.3
  • 38
    • 67649090347 scopus 로고    scopus 로고
    • Current synthesis of triterpene saponins
    • Yu B., Sun J. Current synthesis of triterpene saponins. Chem. Asian. J. 2009, 4:642-654.
    • (2009) Chem. Asian. J. , vol.4 , pp. 642-654
    • Yu, B.1    Sun, J.2
  • 39
    • 70350131097 scopus 로고    scopus 로고
    • Recent progress in the synthesis of naturally occurring triterpenoid saponins
    • Gauthier C., Legault J., Pichette A. Recent progress in the synthesis of naturally occurring triterpenoid saponins. Mini-Rev. Org. Chem. 2009, 6:321-344.
    • (2009) Mini-Rev. Org. Chem. , vol.6 , pp. 321-344
    • Gauthier, C.1    Legault, J.2    Pichette, A.3
  • 40
    • 84855868741 scopus 로고    scopus 로고
    • Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins
    • Gauthier C., Legault J., Piochon-Gauthier M., Pichette A. Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins. Phytochem. Rev. 2011, 10:521-544.
    • (2011) Phytochem. Rev. , vol.10 , pp. 521-544
    • Gauthier, C.1    Legault, J.2    Piochon-Gauthier, M.3    Pichette, A.4
  • 41
    • 79952026605 scopus 로고    scopus 로고
    • Synthesis, biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases
    • Sheng H., Sun H. Synthesis, biology and clinical significance of pentacyclic triterpenes: A multi-target approach to prevention and treatment of metabolic and vascular diseases. Nat. Prod. Rep. 2011, 28:543-593.
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 543-593
    • Sheng, H.1    Sun, H.2
  • 43
    • 85077634689 scopus 로고
    • The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products
    • Mitsunobu O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1-28.
    • (1981) Synthesis , pp. 1-28
    • Mitsunobu, O.1
  • 44
    • 4143084064 scopus 로고    scopus 로고
    • Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation
    • Dembinski R. Recent advances in the Mitsunobu reaction: Modified reagents and the quest for chromatography-free separation. Eur. J. Org. Chem. 2004, 2763-2772.
    • (2004) Eur. J. Org. Chem. , pp. 2763-2772
    • Dembinski, R.1
  • 45
    • 0027238602 scopus 로고
    • Chemical synthesis of 15-ketosterols
    • Kim H.S., Oh S.H. Chemical synthesis of 15-ketosterols. Bioorg. Med. Chem. Lett. 1993, 3:1339-1342.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 1339-1342
    • Kim, H.S.1    Oh, S.H.2
  • 46
    • 0033534604 scopus 로고    scopus 로고
    • First total synthesis of an exceptionally potent antitumor saponin, OSW-1
    • Deng S., Yu B., Lou Y., Hui Y. First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J. Org. Chem. 1999, 64:202-208.
    • (1999) J. Org. Chem. , vol.64 , pp. 202-208
    • Deng, S.1    Yu, B.2    Lou, Y.3    Hui, Y.4
  • 47
    • 33644528891 scopus 로고
    • Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • Dess D.B., Martin J.C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 1983, 48:4155-4156.
    • (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
    • Dess, D.B.1    Martin, J.C.2
  • 48
    • 42949178501 scopus 로고    scopus 로고
    • Total synthesis of Lobatoside E, a potent antitumor cyclic triterpene saponin
    • Zhu C., Tang P., Yu B. Total synthesis of Lobatoside E, a potent antitumor cyclic triterpene saponin. J. Am. Chem. Soc. 2008, 130:5872-5873.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 5872-5873
    • Zhu, C.1    Tang, P.2    Yu, B.3
  • 49
    • 0001199505 scopus 로고
    • Functionalisation of unactivated methyl groups through cyclopalladation reactions
    • Baldwin J.E., Jones R.H., Najera C., Yus M. Functionalisation of unactivated methyl groups through cyclopalladation reactions. Tetrahedron 1985, 41:699-711.
    • (1985) Tetrahedron , vol.41 , pp. 699-711
    • Baldwin, J.E.1    Jones, R.H.2    Najera, C.3    Yus, M.4
  • 50
    • 34247557958 scopus 로고    scopus 로고
    • Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A
    • Garcia-Granados A., Lopez P.E., Melguizo E., Parra A., Simeo Y. Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A. J. Org. Chem. 2007, 72:3500-3509.
    • (2007) J. Org. Chem. , vol.72 , pp. 3500-3509
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 51
    • 0000626006 scopus 로고
    • Peracid oxidation of trimethylsilyl enol ethers: A facile α-hydroxylation procedure
    • Rubottom G.M., Vazquez M.A., Pelegrina D.R. Peracid oxidation of trimethylsilyl enol ethers: A facile α-hydroxylation procedure. Tetrahedron Lett. 1974, 15:4319-4322.
    • (1974) Tetrahedron Lett. , vol.15 , pp. 4319-4322
    • Rubottom, G.M.1    Vazquez, M.A.2    Pelegrina, D.R.3
  • 52
    • 0345246228 scopus 로고
    • De novo synthesis of carbohydrates and related natural products
    • Schmidt R.R. De novo synthesis of carbohydrates and related natural products. Pure Appl. Chem. 1987, 59:415-424.
    • (1987) Pure Appl. Chem. , vol.59 , pp. 415-424
    • Schmidt, R.R.1
  • 53
    • 84888178768 scopus 로고    scopus 로고
    • De novo asymmetric synthesis of the pyranoses: From monosaccharides to oligosaccharides
    • Aljahdali A.Z., Shi P., Zhong Y., O'Doherty G.A. De novo asymmetric synthesis of the pyranoses: From monosaccharides to oligosaccharides. Adv. Carbohydr. Chem. Biochem. 2013, 69:55-123.
    • (2013) Adv. Carbohydr. Chem. Biochem. , vol.69 , pp. 55-123
    • Aljahdali, A.Z.1    Shi, P.2    Zhong, Y.3    O'Doherty, G.A.4
  • 54
    • 84981757672 scopus 로고
    • On some derivatives of dextrose and galactose
    • Koenigs W., Knorr E. On some derivatives of dextrose and galactose. Ber. Dtsch. Chem. Ges. 1901, 34:957-981.
    • (1901) Ber. Dtsch. Chem. Ges. , vol.34 , pp. 957-981
    • Koenigs, W.1    Knorr, E.2
  • 55
    • 0001425870 scopus 로고
    • Some derivatives of milk sugars and the maltose and two new glucosides
    • Fischer E., Fisher H. Some derivatives of milk sugars and the maltose and two new glucosides. Ber. Dtsch. Chem. Ges. 1910, 43:2521-2536.
    • (1910) Ber. Dtsch. Chem. Ges. , vol.43 , pp. 2521-2536
    • Fischer, E.1    Fisher, H.2
  • 56
    • 84982061877 scopus 로고
    • Synthetic application of iodotrimethylsilane and bromotrimethylsilane in saccharide chemistry
    • Thiem J., Meyer B. Synthetic application of iodotrimethylsilane and bromotrimethylsilane in saccharide chemistry. Chem. Ber. 1980, 113:3075-3085.
    • (1980) Chem. Ber. , vol.113 , pp. 3075-3085
    • Thiem, J.1    Meyer, B.2
  • 57
    • 0002796399 scopus 로고
    • An efficient method for glucosylation of hydroxyl compounds using glucopyranosyl fluoride
    • Mukaiyama T., Murai Y., Shoda S. An efficient method for glucosylation of hydroxyl compounds using glucopyranosyl fluoride. Chem. Lett. 1981, 431-432.
    • (1981) Chem. Lett. , pp. 431-432
    • Mukaiyama, T.1    Murai, Y.2    Shoda, S.3
  • 58
    • 84985624827 scopus 로고
    • Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharides
    • Schmidt R.R., Michel J. Facile synthesis of α- and β-O-glycosyl imidates; preparation of glycosides and disaccharides. Angew. Chem. Int. Ed. Engl. 1980, 19:731-732.
    • (1980) Angew. Chem. Int. Ed. Engl. , vol.19 , pp. 731-732
    • Schmidt, R.R.1    Michel, J.2
  • 59
    • 0035906067 scopus 로고    scopus 로고
    • Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors
    • Yu B., Tao H. Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors. Tetrahedron Lett. 2001, 42:2405-2407.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2405-2407
    • Yu, B.1    Tao, H.2
  • 60
    • 77953890252 scopus 로고    scopus 로고
    • Glycosylation with glycosyl N-phenyl trifluoroacetimidates (PTFAI) and a perspective of the future development of new glycosylation methods
    • Yu B., Sun J. Glycosylation with glycosyl N-phenyl trifluoroacetimidates (PTFAI) and a perspective of the future development of new glycosylation methods. Chem. Commun. 2010, 46:4668-4679.
    • (2010) Chem. Commun. , vol.46 , pp. 4668-4679
    • Yu, B.1    Sun, J.2
  • 62
    • 85027946122 scopus 로고    scopus 로고
    • Thioglycosides in Carbohydrate Research
    • Lian G., Zhang X., Yu B. Thioglycosides in Carbohydrate Research. Carbohydr. Res. 2014, 10.1016/j.carres.2014.06.009.
    • (2014) Carbohydr. Res.
    • Lian, G.1    Zhang, X.2    Yu, B.3
  • 64
    • 0007821714 scopus 로고
    • Products of Prévost reaction on d-glucal triacetate
    • Lemieux R.U., Levine S. Products of Prévost reaction on d-glucal triacetate. Can. J. Chem. 1962, 40:1926-1932.
    • (1962) Can. J. Chem. , vol.40 , pp. 1926-1932
    • Lemieux, R.U.1    Levine, S.2
  • 65
    • 0029739240 scopus 로고    scopus 로고
    • Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence
    • Danishefsky S.J., Bilodeau M.T. Glycals in organic synthesis: The evolution of comprehensive strategies for the assembly of oligosaccharides and glycoconjugates of biological consequence. Angew. Chem. Int. Ed. Engl. 1996, 35:1380-1419.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 1380-1419
    • Danishefsky, S.J.1    Bilodeau, M.T.2
  • 66
    • 37049086359 scopus 로고
    • A rapid and efficient synthesis of 1,2-trans-beta-linked glycosides via benzyl-protected or benzoyl-protected glycopyranosyl phosphates
    • Hashimoto S., Honda T., Ikegami S. A rapid and efficient synthesis of 1,2-trans-beta-linked glycosides via benzyl-protected or benzoyl-protected glycopyranosyl phosphates. J. Chem. Soc. Chem., Commun. 1989, 613-619.
    • (1989) J. Chem. Soc. Chem., Commun. , pp. 613-619
    • Hashimoto, S.1    Honda, T.2    Ikegami, S.3
  • 67
    • 0000576352 scopus 로고
    • β-Sialyl phosphite and phosphoramidite: Synthesis and application to the chemoenzymatic synthesis of CMP-sialic acid and sialyl oligosaccharides
    • Kondo H., Ichikawa Y., Wong C.H. β-Sialyl phosphite and phosphoramidite: Synthesis and application to the chemoenzymatic synthesis of CMP-sialic acid and sialyl oligosaccharides. J. Am. Chem. Soc. 1992, 114:8748-8750.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8748-8750
    • Kondo, H.1    Ichikawa, Y.2    Wong, C.H.3
  • 68
    • 0026658833 scopus 로고
    • Efficient sialylation with phosphite as leaving group
    • Martin T.J., Schmidt R.R. Efficient sialylation with phosphite as leaving group. Tetrahedron Lett. 1992, 33:6123-6126.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6123-6126
    • Martin, T.J.1    Schmidt, R.R.2
  • 69
    • 85172016941 scopus 로고
    • A new method on the synthesis of glycosides of phenols
    • Helferich B., Schmitz-Hillebrecht E. A new method on the synthesis of glycosides of phenols. Chem. Ber. 1933, 66:378-383.
    • (1933) Chem. Ber. , vol.66 , pp. 378-383
    • Helferich, B.1    Schmitz-Hillebrecht, E.2
  • 70
    • 0030761432 scopus 로고    scopus 로고
    • Direct glycosylations with 1-hydroxy glycosyl donors using trifluoromethanesulfonic anhydride and diphenyl sulfoxide
    • Garcia B.A., Poole J.L., Gin D.Y. Direct glycosylations with 1-hydroxy glycosyl donors using trifluoromethanesulfonic anhydride and diphenyl sulfoxide. J. Am. Chem. Soc. 1997, 119:7597-7598.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7597-7598
    • Garcia, B.A.1    Poole, J.L.2    Gin, D.Y.3
  • 71
    • 46049086192 scopus 로고    scopus 로고
    • Stereoselective direct glycosylation with anomeric hydroxy sugars by activation with phthalic anhydride and trifluoromethanesulfonic anhydride involving glycosyl phthalate intermediates
    • Kim K.S., Baburao F.D., Baek J.Y., Lee B.Y., Jeon H.B. Stereoselective direct glycosylation with anomeric hydroxy sugars by activation with phthalic anhydride and trifluoromethanesulfonic anhydride involving glycosyl phthalate intermediates. J. Am. Chem. Soc. 2008, 130:8537-8547.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8537-8547
    • Kim, K.S.1    Baburao, F.D.2    Baek, J.Y.3    Lee, B.Y.4    Jeon, H.B.5
  • 72
    • 0008629278 scopus 로고
    • A chemical synthesis of sucrose. A conformational analysis of the reactions of 1,2-anhydro-α-d-glucopyranose triacetate
    • Lemieux R.U., Huber G. A chemical synthesis of sucrose. A conformational analysis of the reactions of 1,2-anhydro-α-d-glucopyranose triacetate. J. Am. Chem. Soc. 1956, 78:4117-4119.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 4117-4119
    • Lemieux, R.U.1    Huber, G.2
  • 76
    • 84890545039 scopus 로고    scopus 로고
    • Mechanistic insights into the gold(I)-catalyzed activation of glycosyl ortho-alkynylbenzoates for glycosidation
    • Tang Y., Li J., Zhu Y., Li Y., Yu B. Mechanistic insights into the gold(I)-catalyzed activation of glycosyl ortho-alkynylbenzoates for glycosidation. J. Am. Chem. Soc. 2013, 135:18396-18405.
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 18396-18405
    • Tang, Y.1    Li, J.2    Zhu, Y.3    Li, Y.4    Yu, B.5
  • 77
    • 84878560594 scopus 로고    scopus 로고
    • Total synthesis of starfish saponin goniopectenoside B
    • Xiao G., Yu B. Total synthesis of starfish saponin goniopectenoside B. Chem. Eur. J. 2013, 19:7708-7712.
    • (2013) Chem. Eur. J. , vol.19 , pp. 7708-7712
    • Xiao, G.1    Yu, B.2
  • 79
    • 84986701213 scopus 로고
    • Synthesis of the pentasaccharide moiety of an asterosaponin
    • Bing H.X., Schmidt R.R. Synthesis of the pentasaccharide moiety of an asterosaponin. Liebigs Ann. Chem. 1992, 817-823.
    • (1992) Liebigs Ann. Chem. , pp. 817-823
    • Bing, H.X.1    Schmidt, R.R.2
  • 80
    • 0034630891 scopus 로고    scopus 로고
    • Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization
    • McDonald F.E., Reddy K.S., Diaz Y. Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization. J. Am. Chem. Soc. 2000, 122:4304-4309.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4304-4309
    • McDonald, F.E.1    Reddy, K.S.2    Diaz, Y.3
  • 81
    • 33749022998 scopus 로고    scopus 로고
    • A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation
    • Zhou M., O'Doherty G.A. A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation. Org. Lett. 2006, 8:4339-4342.
    • (2006) Org. Lett. , vol.8 , pp. 4339-4342
    • Zhou, M.1    O'Doherty, G.A.2
  • 82
    • 34047220599 scopus 로고    scopus 로고
    • De novo approach to 2-deoxy-β-glycosides: Asymmetric syntheses of digoxose and digitoxin
    • Zhou M., O'Doherty G.A. De novo approach to 2-deoxy-β-glycosides: Asymmetric syntheses of digoxose and digitoxin. J. Org. Chem. 2007, 72:2485-2493.
    • (2007) J. Org. Chem. , vol.72 , pp. 2485-2493
    • Zhou, M.1    O'Doherty, G.A.2
  • 83
    • 0029879373 scopus 로고    scopus 로고
    • Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture
    • Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture. J. Am. Chem. Soc. 1996, 118:2521-2522.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2521-2522
    • Fujii, A.1    Hashiguchi, S.2    Uematsu, N.3    Ikariya, T.4    Noyori, R.5
  • 84
    • 24944541990 scopus 로고    scopus 로고
    • De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation
    • Guo H., O'Doherty G.A. De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation. Org. Lett. 2005, 7:3921-3924.
    • (2005) Org. Lett. , vol.7 , pp. 3921-3924
    • Guo, H.1    O'Doherty, G.A.2
  • 85
    • 82155203463 scopus 로고    scopus 로고
    • Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates
    • Ma Y., Li Z., Shi H., Zhang J., Yu B. Assembly of digitoxin by gold(I)-catalyzed glycosidation of glycosyl o-alkynylbenzoates. J. Org. Chem. 2011, 76:9748-9756.
    • (2011) J. Org. Chem. , vol.76 , pp. 9748-9756
    • Ma, Y.1    Li, Z.2    Shi, H.3    Zhang, J.4    Yu, B.5
  • 86
    • 4544384105 scopus 로고    scopus 로고
    • Synthesis of the trisaccharide and tetrasaccharide moieties of the potent immunoadjuvant QS-21
    • Zhu X., Yu B., Hui Y., Schmidt R.R. Synthesis of the trisaccharide and tetrasaccharide moieties of the potent immunoadjuvant QS-21. Eur. J. Org. Chem. 2004, 965-973.
    • (2004) Eur. J. Org. Chem. , pp. 965-973
    • Zhu, X.1    Yu, B.2    Hui, Y.3    Schmidt, R.R.4
  • 87
    • 0005700016 scopus 로고    scopus 로고
    • Synthesis of benzyl O-(2,3,3'-tri-O-acetyl-β-d-apiofuranosy1)-(1→3)-2,4-di-O-benzoyl-α-d-xylopyranoside and its X-ray structure
    • Zhu X., Yu B., Hui Y. Synthesis of benzyl O-(2,3,3'-tri-O-acetyl-β-d-apiofuranosy1)-(1→3)-2,4-di-O-benzoyl-α-d-xylopyranoside and its X-ray structure. Chin. J. Chem. 2000, 18:72-75.
    • (2000) Chin. J. Chem. , vol.18 , pp. 72-75
    • Zhu, X.1    Yu, B.2    Hui, Y.3
  • 88
    • 36849012451 scopus 로고    scopus 로고
    • Protecting groups in carbohydrate chemistry profoundly influence all selectivities in glycosyl couplings
    • American Chemical Society, Washington, DC, A.V. Demchenko (Ed.) Frontiers in Modern Carbohydrate Chemistry
    • Fraser-Reid B., Jayaprakash K.N., Lopez J.C., Gomez A.M., Uriel C. Protecting groups in carbohydrate chemistry profoundly influence all selectivities in glycosyl couplings. ACS Symposium Series 960 2007, 91-117. American Chemical Society, Washington, DC. A.V. Demchenko (Ed.).
    • (2007) ACS Symposium Series 960 , pp. 91-117
    • Fraser-Reid, B.1    Jayaprakash, K.N.2    Lopez, J.C.3    Gomez, A.M.4    Uriel, C.5
  • 89
    • 84892369027 scopus 로고    scopus 로고
    • Recent advances in the synthesis of chitooligosaccharides and congeners
    • Yang Y., Yu B. Recent advances in the synthesis of chitooligosaccharides and congeners. Tetrahedron 2014, 70:1023-1046.
    • (2014) Tetrahedron , vol.70 , pp. 1023-1046
    • Yang, Y.1    Yu, B.2
  • 90
    • 2442684643 scopus 로고    scopus 로고
    • Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins
    • Ple K., Chwalek M., Voutquenne-Nazabadioko L. Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins. Eur. J. Org. Chem. 2004, 1588-1603.
    • (2004) Eur. J. Org. Chem. , pp. 1588-1603
    • Ple, K.1    Chwalek, M.2    Voutquenne-Nazabadioko, L.3
  • 91
    • 84918806276 scopus 로고    scopus 로고
    • PhD Thesis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, China
    • Peng W. Synthesis of Some Saponins and Flavonoid Glycosides 2006, PhD Thesis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, China.
    • (2006) Synthesis of Some Saponins and Flavonoid Glycosides
    • Peng, W.1
  • 92
    • 1242296140 scopus 로고    scopus 로고
    • Facile synthesis of ginsenoside Ro
    • Peng W., Sun J., Lin F., Han X., Yu B. Facile synthesis of ginsenoside Ro. Synlett 2004, 2:259-262.
    • (2004) Synlett , vol.2 , pp. 259-262
    • Peng, W.1    Sun, J.2    Lin, F.3    Han, X.4    Yu, B.5
  • 94
    • 0001068345 scopus 로고
    • Structure-activity relationships of the saponins dioscin and dioscinin
    • Takechi M., Shimada S., Tanaka Y. Structure-activity relationships of the saponins dioscin and dioscinin. Phytochemistry 1991, 30:3943-3944.
    • (1991) Phytochemistry , vol.30 , pp. 3943-3944
    • Takechi, M.1    Shimada, S.2    Tanaka, Y.3
  • 96
    • 0032171509 scopus 로고    scopus 로고
    • A facile synthetic approach to a group of structurally typical diosgenyl saponins
    • Deng S., Yu B., Hui Y. A facile synthetic approach to a group of structurally typical diosgenyl saponins. Tetrahedron Lett. 1998, 39:6511-6514.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6511-6514
    • Deng, S.1    Yu, B.2    Hui, Y.3
  • 97
    • 0032777770 scopus 로고    scopus 로고
    • Synthesis of three diosgenyl saponins: Dioscin, polyphyllin D, and balanitin 7
    • Deng S., Yu B., Hui Y., Yu H., Han X. Synthesis of three diosgenyl saponins: Dioscin, polyphyllin D, and balanitin 7. Carbohydr. Res. 1999, 317:53-62.
    • (1999) Carbohydr. Res. , vol.317 , pp. 53-62
    • Deng, S.1    Yu, B.2    Hui, Y.3    Yu, H.4    Han, X.5
  • 98
    • 0037073937 scopus 로고    scopus 로고
    • Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and Xiebai saponin I
    • Yu B., Tao H. Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and Xiebai saponin I. J. Org. Chem. 2002, 67:9099-9102.
    • (2002) J. Org. Chem. , vol.67 , pp. 9099-9102
    • Yu, B.1    Tao, H.2
  • 99
    • 0037418788 scopus 로고    scopus 로고
    • The synthesis of gracillin and dioscin: Two typical representatives of spirostanol glycosides
    • 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, 338:721-727.
    • (2003) Carbohydr. Res. , vol.338 , pp. 721-727
    • Zou, C.1    Hou, S.2    Shi, Y.3    Lei, P.4    Liang, X.5
  • 100
    • 28444436675 scopus 로고    scopus 로고
    • Facile synthesis of dioscin and its analogues
    • Hou S., Zou C., Zhou L., Lei P., Yu D. Facile synthesis of dioscin and its analogues. Chem. Lett. 2005, 34:1220-1221.
    • (2005) Chem. Lett. , vol.34 , pp. 1220-1221
    • Hou, S.1    Zou, C.2    Zhou, L.3    Lei, P.4    Yu, D.5
  • 101
    • 34548158405 scopus 로고    scopus 로고
    • Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety
    • Miyashita H., Ikeda T., Nohara T. Synthesis of neosaponins and neoglycolipids containing a chacotriosyl moiety. Carbohydr. Res. 2007, 342:2182-2191.
    • (2007) Carbohydr. Res. , vol.342 , pp. 2182-2191
    • Miyashita, H.1    Ikeda, T.2    Nohara, T.3
  • 102
    • 42949160020 scopus 로고    scopus 로고
    • Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity
    • Miyashita H., Kai Y., Nohara T., Ikeda T. Efficient synthesis of α- and β-chacotriosyl glycosides using appropriate donors, and their cytotoxic activity. Carbohydr. Res. 2008, 343:1309-1315.
    • (2008) Carbohydr. Res. , vol.343 , pp. 1309-1315
    • Miyashita, H.1    Kai, Y.2    Nohara, T.3    Ikeda, T.4
  • 103
    • 0035172063 scopus 로고    scopus 로고
    • Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins
    • Mimaki Y., Yokosuka A., Kuroda M., Sashida Y. Cytotoxic activities and structure-cytotoxic relationships of steroidal saponins. Biol. Pharm. Bull. 2001, 24:1286-1289.
    • (2001) Biol. Pharm. Bull. , vol.24 , pp. 1286-1289
    • Mimaki, Y.1    Yokosuka, A.2    Kuroda, M.3    Sashida, Y.4
  • 106
    • 40949083890 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of diosgenyl saponin analogues
    • Kaskiw M.J., Tassotto M.L., Th'ng J., Jiang Z.-H. Synthesis and cytotoxic activity of diosgenyl saponin analogues. Bioorg. Med. Chem. 2008, 16:3209-3217.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 3209-3217
    • Kaskiw, M.J.1    Tassotto, M.L.2    Th'ng, J.3    Jiang, Z.-H.4
  • 109
    • 0142011136 scopus 로고    scopus 로고
    • Synthesis of saponins using partially protected glycosyl donors
    • Du Y., Gu G., Wei G., Hua Y., Linhardt R.J. Synthesis of saponins using partially protected glycosyl donors. Org. Lett. 2003, 5:3627-3630.
    • (2003) Org. Lett. , vol.5 , pp. 3627-3630
    • Du, Y.1    Gu, G.2    Wei, G.3    Hua, Y.4    Linhardt, R.J.5
  • 110
    • 3543025117 scopus 로고    scopus 로고
    • Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors
    • Gu G., Du Y., Linhardt R.J. Facile synthesis of saponins containing 2,3-branched oligosaccharides by using partially protected glycosyl donors. J. Org. Chem. 2004, 69:5497-5500.
    • (2004) J. Org. Chem. , vol.69 , pp. 5497-5500
    • Gu, G.1    Du, Y.2    Linhardt, R.J.3
  • 111
    • 0033521135 scopus 로고    scopus 로고
    • Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation
    • Yu B., Yu H., Hui Y., Han X. Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation. Tetrahedron Lett. 1999, 40:8591-8594.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 8591-8594
    • Yu, B.1    Yu, H.2    Hui, Y.3    Han, X.4
  • 112
    • 0034616467 scopus 로고    scopus 로고
    • Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors
    • Yu H., Yu B., Wu X., Hui Y., Han X. Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors. J. Chem. Soc., Perkin Trans. 2000, 1:1445-1453.
    • (2000) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1445-1453
    • Yu, H.1    Yu, B.2    Wu, X.3    Hui, Y.4    Han, X.5
  • 113
    • 33847666515 scopus 로고    scopus 로고
    • Exploration of the correlation between the structure, hemolytic activity, and cytotoxicity of steroid saponins
    • Wang Y., Zhang Y., Zhu Z., Zhu S., Li Y., Li M., Yu B. Exploration of the correlation between the structure, hemolytic activity, and cytotoxicity of steroid saponins. Bioorg. Med. Chem. 2007, 15:2528-2532.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 2528-2532
    • Wang, Y.1    Zhang, Y.2    Zhu, Z.3    Zhu, S.4    Li, Y.5    Li, M.6    Yu, B.7
  • 115
    • 84895814177 scopus 로고    scopus 로고
    • BEC5 topical combination therapies of solasodine rhamnosyl glycosides derived from the eggplant or Devil's Apple result in rapid removal of large skin cancers. Methods of treatment compared
    • BEC5 topical combination therapies of solasodine rhamnosyl glycosides derived from the eggplant or Devil's Apple result in rapid removal of large skin cancers. Methods of treatment compared. Int. J. Clin. Med. 2012, 3:115-124.
    • (2012) Int. J. Clin. Med. , vol.3 , pp. 115-124
    • Cham, B.E.1
  • 117
    • 84879832541 scopus 로고    scopus 로고
    • Convergent synthesis and cytotoxic activities of 26-thio- and selenodioscin
    • Chen P., Wang P., Song N., Li M. Convergent synthesis and cytotoxic activities of 26-thio- and selenodioscin. Steroids 2013, 78:959-966.
    • (2013) Steroids , vol.78 , pp. 959-966
    • Chen, P.1    Wang, P.2    Song, N.3    Li, M.4
  • 118
    • 84895820056 scopus 로고    scopus 로고
    • Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F
    • Zan X., Gao J., Gu G., Liu S., Sun B., Liu L., Lou H.-X. Synthesis and cytotoxic effect of pseudodiosgenyl saponins with thio-ring F. Bioorg. Med. Chem. Lett. 2014, 24:1600-1604.
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 1600-1604
    • Zan, X.1    Gao, J.2    Gu, G.3    Liu, S.4    Sun, B.5    Liu, L.6    Lou, H.-X.7
  • 119
    • 0035533871 scopus 로고    scopus 로고
    • A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids
    • Jona H., Mandai H., Mukaiyama T. A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids. Chem. Lett. 2001, 30:426-427.
    • (2001) Chem. Lett. , vol.30 , pp. 426-427
    • Jona, H.1    Mandai, H.2    Mukaiyama, T.3
  • 121
    • 0023829545 scopus 로고
    • Digitalis-Mechanisms of action and clinical use
    • Smith T.W. Digitalis-Mechanisms of action and clinical use. N. Engl. J. Med. 1988, 318:358-365.
    • (1988) N. Engl. J. Med. , vol.318 , pp. 358-365
    • Smith, T.W.1
  • 122
    • 0000532319 scopus 로고
    • Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: The first synthesis of a complex saponin
    • Randolph J.T., Danishefsky S.J. Application of the glycal assembly strategy to the synthesis of a branched oligosaccharide: The first synthesis of a complex saponin. J. Am. Chem. Soc. 1993, 115:8473-8474.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 8473-8474
    • Randolph, J.T.1    Danishefsky, S.J.2
  • 123
    • 0029030310 scopus 로고
    • First synthesis of a digitalis saponin. Demonstration of the scope and limitations of a convergent scheme for branched oligosaccharide synthesis by the logic of glycal assembly
    • Randolph J.T., Danishefsky S.J. First synthesis of a digitalis saponin. Demonstration of the scope and limitations of a convergent scheme for branched oligosaccharide synthesis by the logic of glycal assembly. J. Am. Chem. Soc. 1995, 117:5693-5700.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5693-5700
    • Randolph, J.T.1    Danishefsky, S.J.2
  • 124
    • 84887567317 scopus 로고    scopus 로고
    • Efficient one-pot synthesis of tigogenin saponins and their antitumor activities
    • Gu G., An L., Fang M., Guo Z. Efficient one-pot synthesis of tigogenin saponins and their antitumor activities. Carbohydr. Res. 2014, 383:21-26.
    • (2014) Carbohydr. Res. , vol.383 , pp. 21-26
    • Gu, G.1    An, L.2    Fang, M.3    Guo, Z.4
  • 125
    • 80053941493 scopus 로고    scopus 로고
    • Concise synthesis and antitumor activities of trisaccharide steroidal saponins
    • Gu G., Fang M., Liu J., Gu L. Concise synthesis and antitumor activities of trisaccharide steroidal saponins. Carbohydr. Res. 2011, 346:2406-2413.
    • (2011) Carbohydr. Res. , vol.346 , pp. 2406-2413
    • Gu, G.1    Fang, M.2    Liu, J.3    Gu, L.4
  • 128
    • 84860240223 scopus 로고    scopus 로고
    • The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1→3)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside
    • Luo X.-F., Lei F., He Y., Pei S.-C., Hai L., Qian S., Wu Y. The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1→3)-[α-l-rhamnopyranosyl-(1→2)]-β-d-glucopyranoside. J. Asian Nat. Prod. Res. 2012, 14:314-321.
    • (2012) J. Asian Nat. Prod. Res. , vol.14 , pp. 314-321
    • Luo, X.-F.1    Lei, F.2    He, Y.3    Pei, S.-C.4    Hai, L.5    Qian, S.6    Wu, Y.7
  • 130
    • 0025148631 scopus 로고
    • Comparative studies on the constituents of Ophiopogonis tuber and its congeners. VI. Studies on the constituents of the subterranean part of Liriope spicata var. prolifera and L. muscari.
    • Yu B.-Y., Hirai Y., Shoji J., Xu G.-J. Comparative studies on the constituents of Ophiopogonis tuber and its congeners. VI. Studies on the constituents of the subterranean part of Liriope spicata var. prolifera and L. muscari. Chem. Pharm. Bull. 1990, 38:1931-1935.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 1931-1935
    • Yu, B.-Y.1    Hirai, Y.2    Shoji, J.3    Xu, G.-J.4
  • 132
    • 0032576835 scopus 로고    scopus 로고
    • First total synthesis of 25(R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside, an Ophiopogonis saponin from the tuber of Liriope muscari (Decne.)
    • Liu M., Yu B., Hui Y. First total synthesis of 25(R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside, an Ophiopogonis saponin from the tuber of Liriope muscari (Decne.). Tetrahedron Lett. 1998, 39:415-418.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 415-418
    • Liu, M.1    Yu, B.2    Hui, Y.3
  • 133
    • 0034500931 scopus 로고    scopus 로고
    • Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside
    • Liu M., Yu B., Wu X., Hui Y., Fung K.-P. Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside. Carbohydr. Res. 2000, 329:745-754.
    • (2000) Carbohydr. Res. , vol.329 , pp. 745-754
    • Liu, M.1    Yu, B.2    Wu, X.3    Hui, Y.4    Fung, K.-P.5
  • 134
    • 0035192140 scopus 로고    scopus 로고
    • The first synthetic route to furostan saponins
    • Yu B., Liao J., Zhang J., Hui Y. The first synthetic route to furostan saponins. Tetrahedron Lett. 2001, 42:77-79.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 77-79
    • Yu, B.1    Liao, J.2    Zhang, J.3    Hui, Y.4
  • 137
    • 0041857788 scopus 로고    scopus 로고
    • The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro
    • Hu K., Yao X. The cytotoxicity of methyl protodioscin against human cancer cell lines in vitro. Cancer Invest. 2003, 21:389-393.
    • (2003) Cancer Invest. , vol.21 , pp. 389-393
    • Hu, K.1    Yao, X.2
  • 138
    • 33746176533 scopus 로고    scopus 로고
    • Facile conversion of spirostan saponin into furostan saponin: Synthesis of methyl protodioscin and its 26-thio-analogue
    • Li M., Yu B. Facile conversion of spirostan saponin into furostan saponin: Synthesis of methyl protodioscin and its 26-thio-analogue. Org. Lett. 2006, 8:2679-2682.
    • (2006) Org. Lett. , vol.8 , pp. 2679-2682
    • Li, M.1    Yu, B.2
  • 139
    • 3042616092 scopus 로고    scopus 로고
    • Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-β-chacotriosyl moiety
    • Zhang Y., Li Y., Zhu S., Guan H., Lin F., Yu B. Synthesis of bidesmosidic dihydrodiosgenin saponins bearing a 3-O-β-chacotriosyl moiety. Carbohydr. Res. 2004, 339:1753-1759.
    • (2004) Carbohydr. Res. , vol.339 , pp. 1753-1759
    • Zhang, Y.1    Li, Y.2    Zhu, S.3    Guan, H.4    Lin, F.5    Yu, B.6
  • 140
    • 0242354954 scopus 로고    scopus 로고
    • Synthesis of dihydrodiosgenin glycosides as mimetics of bidesmosidic steroidal saponins
    • Suhr R., Lahmann M., Oscarson S., Thiem J. Synthesis of dihydrodiosgenin glycosides as mimetics of bidesmosidic steroidal saponins. Eur. J. Org. Chem., 2003, 4003-4011.
    • (2003) Eur. J. Org. Chem., , pp. 4003-4011
    • Suhr, R.1    Lahmann, M.2    Oscarson, S.3    Thiem, J.4
  • 141
    • 33644973101 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of icogenin and its analogue
    • Hou S., Xu P., Zhou L., Yu D., Lei P. Synthesis and antitumor activity of icogenin and its analogue. Bioorg. Med. Chem. Lett. 2006, 16:2454-2458.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 2454-2458
    • Hou, S.1    Xu, P.2    Zhou, L.3    Yu, D.4    Lei, P.5
  • 142
    • 65449136347 scopus 로고    scopus 로고
    • Synthesis and cytotoxicities of icogenin analogues with disaccharide residues
    • Wang H., Su F., Zhou L., Chen X., Lei P. Synthesis and cytotoxicities of icogenin analogues with disaccharide residues. Bioorg. Med. Chem. Lett. 2009, 196:2796-2800.
    • (2009) Bioorg. Med. Chem. Lett. , vol.196 , pp. 2796-2800
    • Wang, H.1    Su, F.2    Zhou, L.3    Chen, X.4    Lei, P.5
  • 143
    • 78650516089 scopus 로고    scopus 로고
    • The synthesis of cholestane and furostan saponin analogues and the determination of sapogenin's absolute configuration at C-22
    • Wang H., Guo Y., Guan Y., Zhou L., Lei P. The synthesis of cholestane and furostan saponin analogues and the determination of sapogenin's absolute configuration at C-22. Steroids 2011, 76:18-27.
    • (2011) Steroids , vol.76 , pp. 18-27
    • Wang, H.1    Guo, Y.2    Guan, Y.3    Zhou, L.4    Lei, P.5
  • 144
    • 0027498953 scopus 로고
    • Isolation of pseudoprototimosaponin AIII from rhizomes of Anemarrhena asphodeloides and its hypoglycemic activity in streptozotocin-induced diabetic mice
    • Nakashima N., Kimura I., Kimura M. Isolation of pseudoprototimosaponin AIII from rhizomes of Anemarrhena asphodeloides and its hypoglycemic activity in streptozotocin-induced diabetic mice. J. Nat. Prod. 1993, 56:345-350.
    • (1993) J. Nat. Prod. , vol.56 , pp. 345-350
    • Nakashima, N.1    Kimura, I.2    Kimura, M.3
  • 145
    • 0032695244 scopus 로고    scopus 로고
    • Steroidal saponins from Anemarrhena asphodeloides and their effects on superoxide generation
    • Meng Z., Zhang J., Xu S., Sugahara K. Steroidal saponins from Anemarrhena asphodeloides and their effects on superoxide generation. Planta Med. 1999, 65:661-663.
    • (1999) Planta Med. , vol.65 , pp. 661-663
    • Meng, Z.1    Zhang, J.2    Xu, S.3    Sugahara, K.4
  • 146
    • 68949158398 scopus 로고    scopus 로고
    • Total synthesis of a furostan saponin, timosaponin BII
    • Cheng S., Du Y., Ma B., Tan D. Total synthesis of a furostan saponin, timosaponin BII. Org. Biomol. Chem. 2009, 7:3112-3118.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 3112-3118
    • Cheng, S.1    Du, Y.2    Ma, B.3    Tan, D.4
  • 147
    • 0001678648 scopus 로고
    • Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
    • Kubo S., Mimaki Y., Terao M., Sashida Y., Nikaido T., Ohmoto T. Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae. Phytochemistry 1992, 31:3969-3973.
    • (1992) Phytochemistry , vol.31 , pp. 3969-3973
    • Kubo, S.1    Mimaki, Y.2    Terao, M.3    Sashida, Y.4    Nikaido, T.5    Ohmoto, T.6
  • 148
    • 28644433853 scopus 로고    scopus 로고
    • Synthesis of a highly potent antitumor saponin OSW-1 and its analogues
    • Morzycki J.W., Wojtkielewicz A. Synthesis of a highly potent antitumor saponin OSW-1 and its analogues. Phytochem. Rev. 2005, 4:259-277.
    • (2005) Phytochem. Rev. , vol.4 , pp. 259-277
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 149
    • 67649286442 scopus 로고    scopus 로고
    • Chemistry of trisdecacyclic pyrazine antineoplastics: The cephalostatins and ritterazines
    • Lee S., LaCour T.G., Fuchs P.L. Chemistry of trisdecacyclic pyrazine antineoplastics: The cephalostatins and ritterazines. Chem. Rev. 2009, 109:2275-2314.
    • (2009) Chem. Rev. , vol.109 , pp. 2275-2314
    • Lee, S.1    LaCour, T.G.2    Fuchs, P.L.3
  • 150
    • 84880101962 scopus 로고    scopus 로고
    • Structure, bioactivity, and chemical synthesis of OSW-1 and other steroidal glycosides in the genus Ornithogalum
    • Tang Y., Li N., Duan J.-a., Tao W. Structure, bioactivity, and chemical synthesis of OSW-1 and other steroidal glycosides in the genus Ornithogalum. Chem. Rev. 2013, 113:5480-5514.
    • (2013) Chem. Rev. , vol.113 , pp. 5480-5514
    • Tang, Y.1    Li, N.2    Duan, J.-A.3    Tao, W.4
  • 153
    • 0032485307 scopus 로고    scopus 로고
    • The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1
    • Guo C., Fuchs P.L. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1. Tetrahedron Lett. 1998, 39:1099-1102.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1099-1102
    • Guo, C.1    Fuchs, P.L.2
  • 154
    • 0034829735 scopus 로고    scopus 로고
    • A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1
    • Yu W., Jin Z. A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J. Am. Chem. Soc. 2001, 123:3369-3370.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3369-3370
    • Yu, W.1    Jin, Z.2
  • 155
    • 0037067056 scopus 로고    scopus 로고
    • Total synthesis of the anticancer natural product OSW-1
    • Yu W., Jin Z. Total synthesis of the anticancer natural product OSW-1. J. Am. Chem. Soc. 2002, 124:6576-6583.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6576-6583
    • Yu, W.1    Jin, Z.2
  • 156
    • 0037118924 scopus 로고    scopus 로고
    • Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity
    • Morzycki J.W., Wojtkielewicz A. Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity. Carbohydr. Res. 2002, 337:1269-1274.
    • (2002) Carbohydr. Res. , vol.337 , pp. 1269-1274
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 157
    • 28744456358 scopus 로고    scopus 로고
    • OSW saponins: Facile synthesis toward a new type of structures with potent antitumor activities
    • Shi B., Tang P., Hu X., Liu J.O., Yu B. OSW saponins: Facile synthesis toward a new type of structures with potent antitumor activities. J. Org. Chem. 2005, 70:10354-10367.
    • (2005) J. Org. Chem. , vol.70 , pp. 10354-10367
    • Shi, B.1    Tang, P.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 158
    • 36849020952 scopus 로고    scopus 로고
    • A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement
    • Tsubuki M., Matsuo S., Honda T. A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement. Tetrahedron Lett. 2008, 49:229-232.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 229-232
    • Tsubuki, M.1    Matsuo, S.2    Honda, T.3
  • 159
  • 160
    • 4544291577 scopus 로고    scopus 로고
    • 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity
    • Shi B., Wu H., Yu B., Wu J. 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity. Angew. Chem. Int. Ed. Engl. 2004, 43:4324-4327.
    • (2004) Angew. Chem. Int. Ed. Engl. , vol.43 , pp. 4324-4327
    • Shi, B.1    Wu, H.2    Yu, B.3    Wu, J.4
  • 161
    • 2342507229 scopus 로고    scopus 로고
    • Synthesis of OSW-1 analogs with modified side chains and their antitumor activities
    • Deng L., Wu H., Yu B., Jiang M., Wu J. Synthesis of OSW-1 analogs with modified side chains and their antitumor activities. Bioorg. Med. Chem. Lett. 2004, 14:2781-2785.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2781-2785
    • Deng, L.1    Wu, H.2    Yu, B.3    Jiang, M.4    Wu, J.5
  • 165
    • 7044247673 scopus 로고    scopus 로고
    • Synthesis of 5,6-dihydro-OSW-1 and its antitumor activities
    • Deng L., Wu H., Yu B., Jiang M., Wu J. Synthesis of 5,6-dihydro-OSW-1 and its antitumor activities. Chin. J. Chem. 2004, 22:994-998.
    • (2004) Chin. J. Chem. , vol.22 , pp. 994-998
    • Deng, L.1    Wu, H.2    Yu, B.3    Jiang, M.4    Wu, J.5
  • 168
    • 0034680695 scopus 로고    scopus 로고
    • Synthesis of glycosides bearing the disaccharide of OSW-1 or its 1→4-linked analogue and their antitumor activities
    • Ma X., Yu B., Hui Y., Xiao D., Ding J. Synthesis of glycosides bearing the disaccharide of OSW-1 or its 1→4-linked analogue and their antitumor activities. Carbohydr. Res. 2000, 329:495-505.
    • (2000) Carbohydr. Res. , vol.329 , pp. 495-505
    • Ma, X.1    Yu, B.2    Hui, Y.3    Xiao, D.4    Ding, J.5
  • 169
    • 0035940055 scopus 로고    scopus 로고
    • Synthesis of steroidal glycosides bearing the disaccharide moiety of OSW-1 and their antitumor activities
    • Ma X., Yu B., Hui Y., Miao Z., Ding J. Synthesis of steroidal glycosides bearing the disaccharide moiety of OSW-1 and their antitumor activities. Carbohydr. Res. 2001, 334:159-164.
    • (2001) Carbohydr. Res. , vol.334 , pp. 159-164
    • Ma, X.1    Yu, B.2    Hui, Y.3    Miao, Z.4    Ding, J.5
  • 170
    • 34548574624 scopus 로고    scopus 로고
    • Synthesis of the A, B-ring-truncated OSW saponin analogs and their antitumor activities
    • Peng W., Tang P., Hu X., Liu J.O., Yu B. Synthesis of the A, B-ring-truncated OSW saponin analogs and their antitumor activities. Bioorg. Med. Chem. Lett. 2007, 17:5506-5509.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 5506-5509
    • Peng, W.1    Tang, P.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 171
    • 79956118712 scopus 로고    scopus 로고
    • Synthesis of cholestane saponins as mimics of OSW-1 and their cytotoxic activities
    • Zheng D., Guan Y., Chen X., Xu Y., Chen X., Lei P. Synthesis of cholestane saponins as mimics of OSW-1 and their cytotoxic activities. Bioorg. Med. Chem. Lett. 2011, 21:3257-3260.
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 3257-3260
    • Zheng, D.1    Guan, Y.2    Chen, X.3    Xu, Y.4    Chen, X.5    Lei, P.6
  • 172
    • 0033777519 scopus 로고    scopus 로고
    • Candicanoside A, a novel cytotoxic rearranged cholestane glycoside from Galtonia candicans
    • Mimaki Y., Kuroda M., Sashida Y., Yamori T., Tsuruo T. Candicanoside A, a novel cytotoxic rearranged cholestane glycoside from Galtonia candicans. Helv. Chim. Acta 2000, 83:2698-2704.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 2698-2704
    • Mimaki, Y.1    Kuroda, M.2    Sashida, Y.3    Yamori, T.4    Tsuruo, T.5
  • 173
    • 0034897297 scopus 로고    scopus 로고
    • Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity
    • Kuroda M., Mimaki Y., Yokosuka A., Sashida Y. Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity. Chem. Pharm. Bull. 2001, 49:1042-1046.
    • (2001) Chem. Pharm. Bull. , vol.49 , pp. 1042-1046
    • Kuroda, M.1    Mimaki, Y.2    Yokosuka, A.3    Sashida, Y.4
  • 174
    • 34250861588 scopus 로고    scopus 로고
    • Total synthesis of candicanoside A, a potent antitumor saponin with a rearranged steroid side chain
    • Tang P., Yu B. Total synthesis of candicanoside A, a potent antitumor saponin with a rearranged steroid side chain. Angew. Chem. Int. Ed. Engl. 2007, 46:2527-2530.
    • (2007) Angew. Chem. Int. Ed. Engl. , vol.46 , pp. 2527-2530
    • Tang, P.1    Yu, B.2
  • 175
    • 58649112816 scopus 로고    scopus 로고
    • Total synthesis of Candicanoside A, a rearranged cholestane disaccharide, and its 4″-O-p-methoxybenzoate congener
    • Tang P., Yu B. Total synthesis of Candicanoside A, a rearranged cholestane disaccharide, and its 4″-O-p-methoxybenzoate congener. Eur. J. Org. Chem., 2009, 259-269.
    • (2009) Eur. J. Org. Chem., , pp. 259-269
    • Tang, P.1    Yu, B.2
  • 176
    • 0009502608 scopus 로고
    • The structure of osladin-The sweet principle of the rhizomes of Polypodium vulgare L
    • Jizba J., Dolejs L., Herout V., Sorm F. The structure of osladin-The sweet principle of the rhizomes of Polypodium vulgare L. Tetrahedron Lett. 1971, 12:1329-1332.
    • (1971) Tetrahedron Lett. , vol.12 , pp. 1329-1332
    • Jizba, J.1    Dolejs, L.2    Herout, V.3    Sorm, F.4
  • 177
    • 0028887036 scopus 로고
    • Synthesis and structure revision of intensely sweet saponin osladin
    • Yamada H., Nishizawa M. Synthesis and structure revision of intensely sweet saponin osladin. J. Org. Chem. 1995, 60:386-397.
    • (1995) J. Org. Chem. , vol.60 , pp. 386-397
    • Yamada, H.1    Nishizawa, M.2
  • 178
    • 33845681978 scopus 로고    scopus 로고
    • Synthesis of bisdesmosidic kryptogenyl saponins using the 'random glycosylation' strategy and evaluation of their antitumor activity
    • Liu Y., Zhao D.-M., Lu X.-H., Wang H., Chen H., Ke Y., Leng L., Cheng M.-S. Synthesis of bisdesmosidic kryptogenyl saponins using the 'random glycosylation' strategy and evaluation of their antitumor activity. Bioorg. Med. Chem. Lett. 2007, 17:156-160.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 156-160
    • Liu, Y.1    Zhao, D.-M.2    Lu, X.-H.3    Wang, H.4    Chen, H.5    Ke, Y.6    Leng, L.7    Cheng, M.-S.8
  • 179
    • 34548542157 scopus 로고    scopus 로고
    • Synthesis of steroidal saponins bearing an aromatic E ring
    • Wang Z., Li M., Liu X., Yu B. Synthesis of steroidal saponins bearing an aromatic E ring. Tetrahedron Lett. 2007, 48:7323-7326.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7323-7326
    • Wang, Z.1    Li, M.2    Liu, X.3    Yu, B.4
  • 180
    • 0004083981 scopus 로고    scopus 로고
    • Cardiac glycosides
    • John Wiley & Sons Ltd., New York, R. Ikan (Ed.)
    • Albrecht H.P. Cardiac glycosides. Naturally Occurring Glycosides 1999, John Wiley & Sons Ltd., New York. R. Ikan (Ed.).
    • (1999) Naturally Occurring Glycosides
    • Albrecht, H.P.1
  • 181
    • 2542635491 scopus 로고
    • Cardiac glycosides, part I: Experimental pharmacology
    • Springer-Verlag, Berlin, K. Greeff (Ed.)
    • Greeff K., Schadewaldt H. Cardiac glycosides, part I: Experimental pharmacology. Handbook of Experimental Pharmacology 1981, Springer-Verlag, Berlin. K. Greeff (Ed.).
    • (1981) Handbook of Experimental Pharmacology
    • Greeff, K.1    Schadewaldt, H.2
  • 183
    • 12144251755 scopus 로고    scopus 로고
    • Interactions between cardiac glycosides and sodium/potassium-ATPase: Three-dimensional structure-activity relationship models for ligand binding to the E-2-P-i form of the enzyme versus activity inhibition
    • Paula S., Tabet M.R., Ball W.J. Interactions between cardiac glycosides and sodium/potassium-ATPase: Three-dimensional structure-activity relationship models for ligand binding to the E-2-P-i form of the enzyme versus activity inhibition. Biochemistry 2005, 44:498-510.
    • (2005) Biochemistry , vol.44 , pp. 498-510
    • Paula, S.1    Tabet, M.R.2    Ball, W.J.3
  • 186
    • 0021997784 scopus 로고
    • On cardioactive steroids. XVI. Stereoselective β-glycosylation of digitoxose: The synthesis of digitoxin
    • Wiesner K., Tsai T.Y.R., Jin H. On cardioactive steroids. XVI. Stereoselective β-glycosylation of digitoxose: The synthesis of digitoxin. Helv. Chim. Acta 1985, 68:300-314.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 300-314
    • Wiesner, K.1    Tsai, T.Y.R.2    Jin, H.3
  • 187
    • 0022712963 scopus 로고
    • Some recent progress in the synthetic and medicinal chemistry of cardioactive steroid glycosides
    • Wiesner K., Tsai T.Y.R. Some recent progress in the synthetic and medicinal chemistry of cardioactive steroid glycosides. Pure Appl. Chem. 1986, 58:799-810.
    • (1986) Pure Appl. Chem. , vol.58 , pp. 799-810
    • Wiesner, K.1    Tsai, T.Y.R.2
  • 188
    • 0035476321 scopus 로고    scopus 로고
    • Convergent synthesis of digitoxin: Stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal
    • McDonald F.E., Reddy K.S. Convergent synthesis of digitoxin: Stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal. Angew. Chem. Int. Ed. Engl. 2001, 40:3653-3655.
    • (2001) Angew. Chem. Int. Ed. Engl. , vol.40 , pp. 3653-3655
    • McDonald, F.E.1    Reddy, K.S.2
  • 189
    • 84890926040 scopus 로고    scopus 로고
    • Catalytic stereoselective synthesis of β-digitoxosides: Direct synthesis of digitoxin and C1'-epi-digitoxin
    • Baryal K.N., Adhikari S., Zhu J. Catalytic stereoselective synthesis of β-digitoxosides: Direct synthesis of digitoxin and C1'-epi-digitoxin. J. Org. Chem. 2013, 78:12469-12476.
    • (2013) J. Org. Chem. , vol.78 , pp. 12469-12476
    • Baryal, K.N.1    Adhikari, S.2    Zhu, J.3
  • 190
    • 84863469657 scopus 로고    scopus 로고
    • Recent advances in the synthesis of natural 2-deoxy-β-glycosides
    • Borovika A., Nagorny P. Recent advances in the synthesis of natural 2-deoxy-β-glycosides. J. Carbohydr. Chem. 2012, 31:255-283.
    • (2012) J. Carbohydr. Chem. , vol.31 , pp. 255-283
    • Borovika, A.1    Nagorny, P.2
  • 191
    • 0037429819 scopus 로고    scopus 로고
    • Solid-phase assisted solution-phase synthesis with minimum purification-preparation of 2-deoxyglycoconjugates from thioglycosides
    • For selected examples of digitoxin congeners, see:
    • Jaunzems J., Hofer E., Jesberger M., Sourkouni-Argirusi G., Kirschning A. Solid-phase assisted solution-phase synthesis with minimum purification-preparation of 2-deoxyglycoconjugates from thioglycosides. Angew. Chem. Int. Ed. Engl. 2003, 42:1166-1170. For selected examples of digitoxin congeners, see:.
    • (2003) Angew. Chem. Int. Ed. Engl. , vol.42 , pp. 1166-1170
    • Jaunzems, J.1    Hofer, E.2    Jesberger, M.3    Sourkouni-Argirusi, G.4    Kirschning, A.5
  • 194
    • 79954581221 scopus 로고    scopus 로고
    • Synthesis and evaluation of the alpha-d-/alpha-l-rhamnosyl and amicetosyl digitoxigenin oligomers as antitumor agents
    • Wang H.-Y.L., Rojanasakul Y., O'Doherty G.A. Synthesis and evaluation of the alpha-d-/alpha-l-rhamnosyl and amicetosyl digitoxigenin oligomers as antitumor agents. ACS Med. Chem. Lett. 2011, 2:264-269.
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 264-269
    • Wang, H.-Y.L.1    Rojanasakul, Y.2    O'Doherty, G.A.3
  • 195
    • 84875134430 scopus 로고    scopus 로고
    • Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin
    • Beale T.M., Taylor M.S. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org. Lett. 2013, 15:1358-1361.
    • (2013) Org. Lett. , vol.15 , pp. 1358-1361
    • Beale, T.M.1    Taylor, M.S.2
  • 196
    • 15844409635 scopus 로고    scopus 로고
    • New and stereospecific synthesis of allenes in a single step from propargylic alcohols
    • Myers A.G., Zheng B. New and stereospecific synthesis of allenes in a single step from propargylic alcohols. J. Am. Chem. Soc. 1996, 118:4492-4493.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4492-4493
    • Myers, A.G.1    Zheng, B.2
  • 197
    • 84857823601 scopus 로고    scopus 로고
    • Chemical synthesis of the cardiotonic steroid glycosides and related natural products
    • Heasley B. Chemical synthesis of the cardiotonic steroid glycosides and related natural products. Chem. Eur. J. 2012, 18:3092-3120.
    • (2012) Chem. Eur. J. , vol.18 , pp. 3092-3120
    • Heasley, B.1
  • 198
    • 79956110782 scopus 로고    scopus 로고
    • First total synthesis of rhodexin A
    • Jung M.E., Yoo D. First total synthesis of rhodexin A. Org. Lett. 2011, 13:2698-2701.
    • (2011) Org. Lett. , vol.13 , pp. 2698-2701
    • Jung, M.E.1    Yoo, D.2
  • 200
    • 84864585190 scopus 로고    scopus 로고
    • Expeditious synthesis of saponin 57, an appetite suppressant from Hoodia plants
    • Zhang J., Shi H., Ma Y., Yu B. Expeditious synthesis of saponin 57, an appetite suppressant from Hoodia plants. Chem. Commun. 2012, 48:8679-8681.
    • (2012) Chem. Commun. , vol.48 , pp. 8679-8681
    • Zhang, J.1    Shi, H.2    Ma, Y.3    Yu, B.4
  • 201
    • 53449088932 scopus 로고    scopus 로고
    • Hoodia gordonii: A natural appetite suppressant
    • van Heerden F.R. Hoodia gordonii: A natural appetite suppressant. J. Ethnopharmacol. 2008, 119:434-437.
    • (2008) J. Ethnopharmacol. , vol.119 , pp. 434-437
    • van Heerden, F.R.1
  • 203
    • 85024260715 scopus 로고
    • Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia: Structures of ciwujianosides B, C1, C2, C3, C4, D1, D2 and E
    • Shao C.J., Kasai R., Xu J.D., Tanaka O. Saponins from leaves of Acanthopanax senticosus HARMS., Ciwujia: Structures of ciwujianosides B, C1, C2, C3, C4, D1, D2 and E. Chem. Pharm. Bull. 1988, 36:601-608.
    • (1988) Chem. Pharm. Bull. , vol.36 , pp. 601-608
    • Shao, C.J.1    Kasai, R.2    Xu, J.D.3    Tanaka, O.4
  • 204
    • 0033616086 scopus 로고    scopus 로고
    • First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure
    • Yu B., Xie J., Deng S., Hui Y. First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure. J. Am. Chem. Soc. 1999, 121:12196-12197.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 12196-12197
    • Yu, B.1    Xie, J.2    Deng, S.3    Hui, Y.4
  • 205
    • 0032829501 scopus 로고    scopus 로고
    • Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells
    • Mimaki Y., Kuroda M., Asano T., Sashida Y. Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells. J. Nat. Prod. 1999, 62:1279-1283.
    • (1999) J. Nat. Prod. , vol.62 , pp. 1279-1283
    • Mimaki, Y.1    Kuroda, M.2    Asano, T.3    Sashida, Y.4
  • 206
    • 67649417998 scopus 로고    scopus 로고
    • Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis
    • Liu Q., Wang P., Zhang L., Guo T., Lv G., Li Y. Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis. Carbohydr. Res. 2009, 344:1276-1281.
    • (2009) Carbohydr. Res. , vol.344 , pp. 1276-1281
    • Liu, Q.1    Wang, P.2    Zhang, L.3    Guo, T.4    Lv, G.5    Li, Y.6
  • 208
    • 84890963280 scopus 로고    scopus 로고
    • Facile synthesis of the naturally cytotoxic triterpenoid saponin patrinia-glycoside B-II and its conformer
    • Ren L., Liu Y.-X., Lv D., Yan M.-C., Nie H., Liu Y., Cheng M.-S. Facile synthesis of the naturally cytotoxic triterpenoid saponin patrinia-glycoside B-II and its conformer. Molecules 2013, 18:15193-15206.
    • (2013) Molecules , vol.18 , pp. 15193-15206
    • Ren, L.1    Liu, Y.-X.2    Lv, D.3    Yan, M.-C.4    Nie, H.5    Liu, Y.6    Cheng, M.-S.7
  • 209
    • 84878235124 scopus 로고    scopus 로고
    • First total synthesis of natural pulsatilla saponin D via highly stereospecific glycosylation
    • Kim M., Lim E., Jung M. First total synthesis of natural pulsatilla saponin D via highly stereospecific glycosylation. Tetrahedron 2013, 69:5481-5486.
    • (2013) Tetrahedron , vol.69 , pp. 5481-5486
    • Kim, M.1    Lim, E.2    Jung, M.3
  • 210
    • 38649119546 scopus 로고    scopus 로고
    • Pharmacokinetics of effective component of Anemone flaccida Fr. Schmidt in mice following single intra-gastric dosing
    • Bing F., Yi Y., Zhang G. Pharmacokinetics of effective component of Anemone flaccida Fr. Schmidt in mice following single intra-gastric dosing. J. China Pharm. Univ. 2005, 36:338-341.
    • (2005) J. China Pharm. Univ. , vol.36 , pp. 338-341
    • Bing, F.1    Yi, Y.2    Zhang, G.3
  • 211
    • 0026341876 scopus 로고
    • Two new oleanane saponins from Anemone flaccida
    • Zhao L., Chen W.M., Fang Q.C. Two new oleanane saponins from Anemone flaccida. Planta Med. 1991, 57:572-574.
    • (1991) Planta Med. , vol.57 , pp. 572-574
    • Zhao, L.1    Chen, W.M.2    Fang, Q.C.3
  • 212
    • 38649137996 scopus 로고    scopus 로고
    • Synthesis of flaccidoside II, a bidesmosidic triterpene saponin isolated from Chinese folk medicine Di Wu
    • Cheng S., Du Y., Bing F., Zhang G. Synthesis of flaccidoside II, a bidesmosidic triterpene saponin isolated from Chinese folk medicine Di Wu. Carbohydr. Res. 2008, 343:462-469.
    • (2008) Carbohydr. Res. , vol.343 , pp. 462-469
    • Cheng, S.1    Du, Y.2    Bing, F.3    Zhang, G.4
  • 213
    • 77649328407 scopus 로고    scopus 로고
    • Efficient synthesis of Flaccidoside II, a bioactive component of Chinese folk medicine Di Wu
    • Liu Q., Zhang L., Li X., Guo T., Wang P., Li Y. Efficient synthesis of Flaccidoside II, a bioactive component of Chinese folk medicine Di Wu. J. Carbohydr. Chem. 2009, 28:506-519.
    • (2009) J. Carbohydr. Chem. , vol.28 , pp. 506-519
    • Liu, Q.1    Zhang, L.2    Li, X.3    Guo, T.4    Wang, P.5    Li, Y.6
  • 214
    • 66249117677 scopus 로고    scopus 로고
    • Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase
    • Guo T., Liu Q., Wang P., Zhang L., Zhang W., Li Y. Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase. Carbohydr. Res. 2009, 344:1167-1174.
    • (2009) Carbohydr. Res. , vol.344 , pp. 1167-1174
    • Guo, T.1    Liu, Q.2    Wang, P.3    Zhang, L.4    Zhang, W.5    Li, Y.6
  • 215
    • 84877079384 scopus 로고    scopus 로고
    • Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives
    • Liu Q., Liu H., Zhang L., Guo T., Wang P., Geng M., Li Y. Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives. Eur. J. Med. Chem. 2013, 64:1-15.
    • (2013) Eur. J. Med. Chem. , vol.64 , pp. 1-15
    • Liu, Q.1    Liu, H.2    Zhang, L.3    Guo, T.4    Wang, P.5    Geng, M.6    Li, Y.7
  • 218
    • 0037461123 scopus 로고    scopus 로고
    • Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside
    • Sun J., Han X., Yu B. Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside. Carbohydr. Res. 2003, 338:827-833.
    • (2003) Carbohydr. Res. , vol.338 , pp. 827-833
    • Sun, J.1    Han, X.2    Yu, B.3
  • 219
    • 33745766649 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoid saponins: Lotoidoside D and E
    • Yan M.-C., Liu Y., Chen H., Ke Y., Xu Q.-C., Cheng M.-S. Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoid saponins: Lotoidoside D and E. Bioorg. Med. Chem. Lett. 2006, 16:4200-4204.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 4200-4204
    • Yan, M.-C.1    Liu, Y.2    Chen, H.3    Ke, Y.4    Xu, Q.-C.5    Cheng, M.-S.6
  • 220
    • 77649179061 scopus 로고    scopus 로고
    • Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
    • Wang P., Wang J., Guo T., Li Y. Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins. Carbohydr. Res. 2010, 345:607-620.
    • (2010) Carbohydr. Res. , vol.345 , pp. 607-620
    • Wang, P.1    Wang, J.2    Guo, T.3    Li, Y.4
  • 222
    • 3142719030 scopus 로고    scopus 로고
    • Synthesis of a typical glucuronide-containing saponin, 28-O-β-d-glucopyranosyl oleanate 3-O-β-d-galactopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucuronopyranoside
    • Peng W., Han X., Yu B. Synthesis of a typical glucuronide-containing saponin, 28-O-β-d-glucopyranosyl oleanate 3-O-β-d-galactopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→3)]-β-d-glucuronopyranoside. Synthesis 2004, 10:1641-1647.
    • (2004) Synthesis , vol.10 , pp. 1641-1647
    • Peng, W.1    Han, X.2    Yu, B.3
  • 223
    • 46849083748 scopus 로고    scopus 로고
    • Synthesis of betavulgaroside III, a representative triterpene seco-glycoside
    • Zhu S., Li Y., Yu B. Synthesis of betavulgaroside III, a representative triterpene seco-glycoside. J. Org. Chem. 2008, 73:4978-4985.
    • (2008) J. Org. Chem. , vol.73 , pp. 4978-4985
    • Zhu, S.1    Li, Y.2    Yu, B.3
  • 224
    • 52049115713 scopus 로고    scopus 로고
    • Synthesis of QS-21-xylose: Establishment of the immunopotentiating activity of synthetic QS-21 adjuvant with a melanoma Vaccine
    • Deng K., Adams M.M., Damani P., Livingston P.O., Ragupathi G., Gin D.Y. Synthesis of QS-21-xylose: Establishment of the immunopotentiating activity of synthetic QS-21 adjuvant with a melanoma Vaccine. Angew. Chem. Int. Ed. Engl. 2008, 47:6395-6398.
    • (2008) Angew. Chem. Int. Ed. Engl. , vol.47 , pp. 6395-6398
    • Deng, K.1    Adams, M.M.2    Damani, P.3    Livingston, P.O.4    Ragupathi, G.5    Gin, D.Y.6
  • 225
    • 79955440243 scopus 로고    scopus 로고
    • Facile synthesis of several oleanane-type triterpenoid saponins
    • Liu Q., Fan Z., Li D., Li W., Guo T. Facile synthesis of several oleanane-type triterpenoid saponins. J. Carbohydr. Chem. 2011, 29:386-402.
    • (2011) J. Carbohydr. Chem. , vol.29 , pp. 386-402
    • Liu, Q.1    Fan, Z.2    Li, D.3    Li, W.4    Guo, T.5
  • 226
    • 84862792982 scopus 로고    scopus 로고
    • Facile synthesis of triterpenoid saponins bearing β-Glu/Gal-(1→3)-β-GluA methyl ester and their cytotoxic activities
    • Gao J., Li X., Liu S., Cui M., Lou H.-X. Facile synthesis of triterpenoid saponins bearing β-Glu/Gal-(1→3)-β-GluA methyl ester and their cytotoxic activities. Bioorg. Med. Chem. Lett. 2012, 22:2396-2400.
    • (2012) Bioorg. Med. Chem. Lett. , vol.22 , pp. 2396-2400
    • Gao, J.1    Li, X.2    Liu, S.3    Cui, M.4    Lou, H.-X.5
  • 227
    • 0032783094 scopus 로고    scopus 로고
    • A cytotoxic triterpene saponin from the root bark of Aralia dasyphylla
    • Xiao K., Yi Y.-H., Wang Z.-Z., Tang H.-F., Li Y.-Q., Lin H.-W. A cytotoxic triterpene saponin from the root bark of Aralia dasyphylla. J. Nat. Prod. 1999, 62:1030-1032.
    • (1999) J. Nat. Prod. , vol.62 , pp. 1030-1032
    • Xiao, K.1    Yi, Y.-H.2    Wang, Z.-Z.3    Tang, H.-F.4    Li, Y.-Q.5    Lin, H.-W.6
  • 228
    • 0000159643 scopus 로고
    • Betavulgaroside-I, betavulgaroside-II, betavulgaroside-III, betavulgaroside-IV, and betavulgaroside-V, hypoglycemic glucuronide saponins from the roots and leaves of Beta vulgaris L (sugar-beet)
    • Yoshikawa M., Murakami T., Kadoya M., Matsuda H., Yamahara J., Muraoka O., Murakami N. Betavulgaroside-I, betavulgaroside-II, betavulgaroside-III, betavulgaroside-IV, and betavulgaroside-V, hypoglycemic glucuronide saponins from the roots and leaves of Beta vulgaris L (sugar-beet). Heterocycles 1995, 41:1621-1626.
    • (1995) Heterocycles , vol.41 , pp. 1621-1626
    • Yoshikawa, M.1    Murakami, T.2    Kadoya, M.3    Matsuda, H.4    Yamahara, J.5    Muraoka, O.6    Murakami, N.7
  • 229
    • 0029067549 scopus 로고
    • Achyranthosides C and D, novel glucuronide saponins from Achyranthes fauriei root
    • Ida Y., Satoh Y., Katsumata M., Nagasao M., Shoji J. Achyranthosides C and D, novel glucuronide saponins from Achyranthes fauriei root. Chem. Pharm. Bull. 1995, 43:896-898.
    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 896-898
    • Ida, Y.1    Satoh, Y.2    Katsumata, M.3    Nagasao, M.4    Shoji, J.5
  • 230
    • 0028096688 scopus 로고
    • Sialyl Lewis X mimics derived from a pharmacophore search are selectin inhibitors with anti-inflammatory activity
    • Rao B.N.N., Anderson M.B., Musser J.H., Gilbert J.H., Schaefer M.E., Foxall C., Brandley B.K. Sialyl Lewis X mimics derived from a pharmacophore search are selectin inhibitors with anti-inflammatory activity. J. Biol. Chem. 1994, 269:19663-19666.
    • (1994) J. Biol. Chem. , vol.269 , pp. 19663-19666
    • Rao, B.N.N.1    Anderson, M.B.2    Musser, J.H.3    Gilbert, J.H.4    Schaefer, M.E.5    Foxall, C.6    Brandley, B.K.7
  • 231
    • 0026033441 scopus 로고
    • Separation and characterization of saponins with adjuvant activity from Quillaja saponaria molina cortex
    • Kensil C.R., Patel U., Lennick M., Marciani D. Separation and characterization of saponins with adjuvant activity from Quillaja saponaria molina cortex. J. Immunol. 1991, 146:431-437.
    • (1991) J. Immunol. , vol.146 , pp. 431-437
    • Kensil, C.R.1    Patel, U.2    Lennick, M.3    Marciani, D.4
  • 234
    • 0033578091 scopus 로고    scopus 로고
    • Carbohydrate chemistry-Sugars out in the open
    • Hindsgaul O. Carbohydrate chemistry-Sugars out in the open. Nature 1999, 399:644-645.
    • (1999) Nature , vol.399 , pp. 644-645
    • Hindsgaul, O.1
  • 235
    • 19544371385 scopus 로고    scopus 로고
    • Synthesis of anemoclemoside B, the first natural product with an open-chain cyclic acetal glycosidic linkage
    • Sun J., Han X., Yu B. Synthesis of anemoclemoside B, the first natural product with an open-chain cyclic acetal glycosidic linkage. Org. Lett. 2005, 7:1935-1938.
    • (2005) Org. Lett. , vol.7 , pp. 1935-1938
    • Sun, J.1    Han, X.2    Yu, B.3
  • 236
    • 85008132336 scopus 로고
    • Studies on the constituents of Actinostemma lobatum Maxim. V. Structures of Lobatosides B, E, F and G, the dicrotalic acid esters of bayogenin bisdesmosides isolated from the herb
    • Fujioka T., Iwamoto M., Iwase Y., Hachiyama S., Okabe H., Yamauchi T., Mihashi K. Studies on the constituents of Actinostemma lobatum Maxim. V. Structures of Lobatosides B, E, F and G, the dicrotalic acid esters of bayogenin bisdesmosides isolated from the herb. Chem. Pharm. Bull. 1989, 37:2355-2360.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 2355-2360
    • Fujioka, T.1    Iwamoto, M.2    Iwase, Y.3    Hachiyama, S.4    Okabe, H.5    Yamauchi, T.6    Mihashi, K.7
  • 237
    • 16144364877 scopus 로고    scopus 로고
    • Antitumor agents 171. Cytotoxicities of Lobatosides B, C, D, and E, cyclic bisdesmosides isolated from Actinostemma lobatum Maxim
    • Fujioka T., Kashiwada Y., Okabe H., Mihashi K., Lee K.H. Antitumor agents 171. Cytotoxicities of Lobatosides B, C, D, and E, cyclic bisdesmosides isolated from Actinostemma lobatum Maxim. Bioorg. Med. Chem. Lett. 1996, 6:2807-2810.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2807-2810
    • Fujioka, T.1    Kashiwada, Y.2    Okabe, H.3    Mihashi, K.4    Lee, K.H.5
  • 239
    • 0030111347 scopus 로고    scopus 로고
    • Araliasaponins I-XI, triterpene saponins from the roots of Aralia decaisneana
    • Miyase T., Shiokawa K.I., Dong M.Z., Ueno A. Araliasaponins I-XI, triterpene saponins from the roots of Aralia decaisneana. Phytochemistry 1996, 41:1411-1418.
    • (1996) Phytochemistry , vol.41 , pp. 1411-1418
    • Miyase, T.1    Shiokawa, K.I.2    Dong, M.Z.3    Ueno, A.4
  • 240
    • 23744503552 scopus 로고    scopus 로고
    • Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue
    • Wang P., Li C., Zang J., Song N., Zhang X., Li Y. Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Carbohydr. Res. 2005, 340:2086-2096.
    • (2005) Carbohydr. Res. , vol.340 , pp. 2086-2096
    • Wang, P.1    Li, C.2    Zang, J.3    Song, N.4    Zhang, X.5    Li, Y.6
  • 241
    • 14544270583 scopus 로고    scopus 로고
    • Triterpenoid saponins from the roots of Pulsatilla koreana
    • Bang S.-C., Kim Y., Lee J.-H., Ahn B.-Z. Triterpenoid saponins from the roots of Pulsatilla koreana. J. Nat. Prod. 2005, 68:268-272.
    • (2005) J. Nat. Prod. , vol.68 , pp. 268-272
    • Bang, S.-C.1    Kim, Y.2    Lee, J.-H.3    Ahn, B.-Z.4
  • 242
    • 45449109572 scopus 로고    scopus 로고
    • Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues
    • Gauthier C., Legault J., Lavoie S., Rondeau S., Tremblay S., Pichette A. Synthesis of two natural betulinic acid saponins containing α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranose and their analogues. Tetrahedron 2008, 64:7386-7399.
    • (2008) Tetrahedron , vol.64 , pp. 7386-7399
    • Gauthier, C.1    Legault, J.2    Lavoie, S.3    Rondeau, S.4    Tremblay, S.5    Pichette, A.6
  • 244
    • 63549116461 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products
    • Gauthier C., Legault J., Piochon M., Lavoie S., Tremblay S., Pichette A. Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products. Bioorg. Med. Chem. Lett. 2009, 19:2310-2314.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2310-2314
    • Gauthier, C.1    Legault, J.2    Piochon, M.3    Lavoie, S.4    Tremblay, S.5    Pichette, A.6
  • 245
    • 34447625709 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin
    • Thibeault D., Gauthier C., Legault J., Bouchard J., Dufour P., Pichette A. Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin. Bioorg. Med. Chem. 2007, 15:6144-6157.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 6144-6157
    • Thibeault, D.1    Gauthier, C.2    Legault, J.3    Bouchard, J.4    Dufour, P.5    Pichette, A.6
  • 247
    • 80054699816 scopus 로고    scopus 로고
    • Efficient synthesis of lupane-type saponins via gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors
    • Li Y., Sun J., Yu B. Efficient synthesis of lupane-type saponins via gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors. Org. Lett. 2011, 13:5508-5511.
    • (2011) Org. Lett. , vol.13 , pp. 5508-5511
    • Li, Y.1    Sun, J.2    Yu, B.3
  • 249
    • 41149097964 scopus 로고    scopus 로고
    • Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents
    • Cmoch P., Pakulski Z., Swaczynova J., Strnad M. Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents. Carbohydr. Res. 2008, 343:995-1003.
    • (2008) Carbohydr. Res. , vol.343 , pp. 995-1003
    • Cmoch, P.1    Pakulski, Z.2    Swaczynova, J.3    Strnad, M.4
  • 250
    • 84897404710 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship study of cytotoxic lupane-type 3β-O-monodesmosidic saponins with an extended C-28 side chain
    • Cmoch P., Korda A., Rarova L., Oklestkova J., Strnad M., Luboradzki R., Pakulski Z. Synthesis and structure-activity relationship study of cytotoxic lupane-type 3β-O-monodesmosidic saponins with an extended C-28 side chain. Tetrahedron 2014, 70:2717-2730.
    • (2014) Tetrahedron , vol.70 , pp. 2717-2730
    • Cmoch, P.1    Korda, A.2    Rarova, L.3    Oklestkova, J.4    Strnad, M.5    Luboradzki, R.6    Pakulski, Z.7
  • 251
    • 0002729980 scopus 로고    scopus 로고
    • Getting to the root of ginseng
    • Sticher O. Getting to the root of ginseng. ChemTech 1998, 4:26-32.
    • (1998) ChemTech , vol.4 , pp. 26-32
    • Sticher, O.1
  • 252
    • 84862277245 scopus 로고    scopus 로고
    • Chemical insights into ginseng as a resource for natural antioxidants
    • Liu Z.-Q. Chemical insights into ginseng as a resource for natural antioxidants. Chem. Rev. 2012, 112:3329-3355.
    • (2012) Chem. Rev. , vol.112 , pp. 3329-3355
    • Liu, Z.-Q.1
  • 253
    • 0002797851 scopus 로고
    • Panax ginseng C.A. Mey
    • Springer, London, W. Tang, G. Eisenbrand (Eds.)
    • Tang W., Eisenbrand G. Panax ginseng C.A. Mey. Chinese Drugs of Plant Origins 1992, 711-737. Springer, London. W. Tang, G. Eisenbrand (Eds.).
    • (1992) Chinese Drugs of Plant Origins , pp. 711-737
    • Tang, W.1    Eisenbrand, G.2
  • 254
    • 28644442090 scopus 로고    scopus 로고
    • Biological activities and chemistry of saponins from Panax ginseng C. A. Meyer
    • Park J.D., Rhee D.K., Lee Y.H. Biological activities and chemistry of saponins from Panax ginseng C. A. Meyer. Phytochem. Rev. 2005, 4:159-175.
    • (2005) Phytochem. Rev. , vol.4 , pp. 159-175
    • Park, J.D.1    Rhee, D.K.2    Lee, Y.H.3
  • 255
    • 50349101675 scopus 로고    scopus 로고
    • Ginsenosides: Chemistry, biosynthesis, analysis, and potential health effects
    • Christensen L.P. Ginsenosides: Chemistry, biosynthesis, analysis, and potential health effects. Adv. Food Nutr. Res. 2009, 55:1-99.
    • (2009) Adv. Food Nutr. Res. , vol.55 , pp. 1-99
    • Christensen, L.P.1
  • 256
    • 79952012614 scopus 로고    scopus 로고
    • Isolation and analysis of ginseng: Advances and challenges
    • Qi L.-W., Wang C.-Z., Yuan C.-S. Isolation and analysis of ginseng: Advances and challenges. Nat. Prod. Rep. 2011, 28:467-495.
    • (2011) Nat. Prod. Rep. , vol.28 , pp. 467-495
    • Qi, L.-W.1    Wang, C.-Z.2    Yuan, C.-S.3
  • 257
    • 0028810456 scopus 로고
    • Cytotoxicities of gingseng saponins and their degradation products against some cancer cell-lines
    • Beak N.I., Kim D.S., Lee Y.H., Park J.D., Lee C.B., Kim S.I. Cytotoxicities of gingseng saponins and their degradation products against some cancer cell-lines. Arch. Pharm. Res. 1995, 18:164-168.
    • (1995) Arch. Pharm. Res. , vol.18 , pp. 164-168
    • Beak, N.I.1    Kim, D.S.2    Lee, Y.H.3    Park, J.D.4    Lee, C.B.5    Kim, S.I.6
  • 258
    • 0023220303 scopus 로고
    • Plant-glycoside modulation of cell surface related to control of differentiation in cultured B16 melanoma cells
    • Ota T., Fujikawa-Yamamoto K., Zong Z.-P., Yamazaki M., Odashima S. Plant-glycoside modulation of cell surface related to control of differentiation in cultured B16 melanoma cells. Cancer Res. 1987, 47:3863-3867.
    • (1987) Cancer Res. , vol.47 , pp. 3863-3867
    • Ota, T.1    Fujikawa-Yamamoto, K.2    Zong, Z.-P.3    Yamazaki, M.4    Odashima, S.5
  • 259
    • 0026322969 scopus 로고
    • Mechanism of action of ginsenoside Rh2: Uptake and metabolism of ginsenoside Rh2 by cultured B16 melanoma cells
    • Ota T., Meada M., Odashima S. Mechanism of action of ginsenoside Rh2: Uptake and metabolism of ginsenoside Rh2 by cultured B16 melanoma cells. J. Pharm. Sci. 1991, 80:1141-1146.
    • (1991) J. Pharm. Sci. , vol.80 , pp. 1141-1146
    • Ota, T.1    Meada, M.2    Odashima, S.3
  • 260
    • 0030730722 scopus 로고    scopus 로고
    • Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng
    • Atopkina L.N., Uvarova N.I., Elyakov G.B. Simplified preparation of the ginsenoside-Rh2 minor saponin from ginseng. Carbohydr. Res. 1997, 303:449-451.
    • (1997) Carbohydr. Res. , vol.303 , pp. 449-451
    • Atopkina, L.N.1    Uvarova, N.I.2    Elyakov, G.B.3
  • 261
    • 79956025344 scopus 로고    scopus 로고
    • Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor
    • Liao J., Sun J., Niu Y., Yu B. Synthesis of ginsenoside Rh2 and chikusetsusaponin-LT8 via gold(I)-catalyzed glycosylation with a glycosyl ortho-alkynylbenzoate as donor. Tetrahedron Lett. 2011, 52:3075-3078.
    • (2011) Tetrahedron Lett. , vol.52 , pp. 3075-3078
    • Liao, J.1    Sun, J.2    Niu, Y.3    Yu, B.4
  • 262
    • 79957496405 scopus 로고    scopus 로고
    • Synthesis of 20S-protopanaxadiol β-d-galactopyranosides
    • Atopkina L.N., Denisenko V.A. Synthesis of 20S-protopanaxadiol β-d-galactopyranosides. Chem. Nat. Compd. 2011, 47:79-84.
    • (2011) Chem. Nat. Compd. , vol.47 , pp. 79-84
    • Atopkina, L.N.1    Denisenko, V.A.2
  • 263
    • 0036062657 scopus 로고    scopus 로고
    • Ginsenosides from Panax ginseng differentially regulate lymphocyte proliferation
    • Cho J.Y., Kim A.R., Yoo E.S., Baik K.U., Park M.H. Ginsenosides from Panax ginseng differentially regulate lymphocyte proliferation. Planta Med. 2002, 68:497-500.
    • (2002) Planta Med. , vol.68 , pp. 497-500
    • Cho, J.Y.1    Kim, A.R.2    Yoo, E.S.3    Baik, K.U.4    Park, M.H.5
  • 264
  • 265
  • 266
    • 0018068962 scopus 로고
    • Dammarane type saponins of leaves of Panax japonicus C.A. Meyer. (2). Saponins of the specimens collected in Tottori-ken, Kyoto-shi, and Niigata-ken
    • Yahara S., Tanaka O., Nishioka I. Dammarane type saponins of leaves of Panax japonicus C.A. Meyer. (2). Saponins of the specimens collected in Tottori-ken, Kyoto-shi, and Niigata-ken. Chem. Pharm. Bull. 1978, 26:3010-3016.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 3010-3016
    • Yahara, S.1    Tanaka, O.2    Nishioka, I.3
  • 268
    • 84859213870 scopus 로고    scopus 로고
    • Synthesis of diglycosides of 3β,20S-dihydroxydammar-24-en-12-one
    • Atopkina L.N., Denisenko V.A. Synthesis of diglycosides of 3β,20S-dihydroxydammar-24-en-12-one. Chem. Nat. Compd. 2012, 48:66-71.
    • (2012) Chem. Nat. Compd. , vol.48 , pp. 66-71
    • Atopkina, L.N.1    Denisenko, V.A.2
  • 269
    • 33646494503 scopus 로고    scopus 로고
    • Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-d-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicas
    • Atopkina L.N., Denisenko V.A. Synthesis of 3β,20S-dihydroxydammar-24-en-12-one 3,20-di-O-β-d-glucopyranoside (chikusetsusaponin-LT8), a glycoside from Panax japonicas. Chem. Nat. Compd. 2006, 42:55-60.
    • (2006) Chem. Nat. Compd. , vol.42 , pp. 55-60
    • Atopkina, L.N.1    Denisenko, V.A.2
  • 270
    • 0004171333 scopus 로고    scopus 로고
    • Steroidal oligoglycosides from marine sources
    • Wiley, Chichester, R. Ikan (Ed.)
    • Iorizzi M., Riccio R. Steroidal oligoglycosides from marine sources. Naturally Occurring Glycosides 1999, 345-397. Wiley, Chichester. R. Ikan (Ed.).
    • (1999) Naturally Occurring Glycosides , pp. 345-397
    • Iorizzi, M.1    Riccio, R.2
  • 271
    • 79952573815 scopus 로고    scopus 로고
    • Steroid glycosides from marine organisms
    • Ivanchina N.V., Kicha A.A., Stonik V.A. Steroid glycosides from marine organisms. Steroids 2011, 76:425-454.
    • (2011) Steroids , vol.76 , pp. 425-454
    • Ivanchina, N.V.1    Kicha, A.A.2    Stonik, V.A.3
  • 273
    • 0023790188 scopus 로고
    • Shark repellent lipophilic constituents in the defense secretion of the Moses sole (Pardachirus marmoratus)
    • Tachibwa K., Gruber S.H. Shark repellent lipophilic constituents in the defense secretion of the Moses sole (Pardachirus marmoratus). Toxicon 1988, 26:839-853.
    • (1988) Toxicon , vol.26 , pp. 839-853
    • Tachibwa, K.1    Gruber, S.H.2
  • 274
    • 0021717207 scopus 로고
    • Pavoninins: Shark-repelling ichthyotoxins from the defense secretion of the Pacific sole
    • Tachibana K., Sakaitani M., Nakanishi K. Pavoninins: Shark-repelling ichthyotoxins from the defense secretion of the Pacific sole. Science 1984, 226:703-705.
    • (1984) Science , vol.226 , pp. 703-705
    • Tachibana, K.1    Sakaitani, M.2    Nakanishi, K.3
  • 275
    • 0021923602 scopus 로고
    • Pavoninins, shark-repelling and ichthyotoxic steroid N-acetylglucosaminides from the defense secretion of the sole Pardachirus pavoninus (Soleidae)
    • Tachibana K., Sakaitani M., Nakanishi K. Pavoninins, shark-repelling and ichthyotoxic steroid N-acetylglucosaminides from the defense secretion of the sole Pardachirus pavoninus (Soleidae). Tetrahedron 1985, 41:1027-1037.
    • (1985) Tetrahedron , vol.41 , pp. 1027-1037
    • Tachibana, K.1    Sakaitani, M.2    Nakanishi, K.3
  • 276
    • 84914734753 scopus 로고
    • Springer-Verlag, Berlin, New York, L. Bolis, J. Zadunaisky, R. Gilles (Eds.)
    • Toxins, Drugs and Pollutants in Marine Animals 1984, Springer-Verlag, Berlin, New York. L. Bolis, J. Zadunaisky, R. Gilles (Eds.).
    • (1984) Toxins, Drugs and Pollutants in Marine Animals
  • 277
    • 0022869696 scopus 로고
    • Purification and pore-forming activity of two hydrophobic polypeptides from the secretion of the Red Sea Moses sole (Pardachirus marmoratus)
    • Lazarovici P., Primor N., Loew L.M. Purification and pore-forming activity of two hydrophobic polypeptides from the secretion of the Red Sea Moses sole (Pardachirus marmoratus). J. Biol. Chem. 1986, 261:16704-16713.
    • (1986) J. Biol. Chem. , vol.261 , pp. 16704-16713
    • Lazarovici, P.1    Primor, N.2    Loew, L.M.3
  • 278
    • 0000213079 scopus 로고
    • Synthesis of mosesin-4, a naturally occurring steroid saponin with shark repellent activity, and its analog 7-β-galactosyl ethyl cholate
    • Gargiulo D., Blizzard T.A., Nakanishi K. Synthesis of mosesin-4, a naturally occurring steroid saponin with shark repellent activity, and its analog 7-β-galactosyl ethyl cholate. Tetrahedron 1989, 45:5423-5432.
    • (1989) Tetrahedron , vol.45 , pp. 5423-5432
    • Gargiulo, D.1    Blizzard, T.A.2    Nakanishi, K.3
  • 279
    • 0031452735 scopus 로고    scopus 로고
    • Synthesis of pavoninin-1, a shark repellent substance, and its structural analogues toward mechanistic studies on their membrane perturbation
    • Ohnishi Y., Tachibana K. Synthesis of pavoninin-1, a shark repellent substance, and its structural analogues toward mechanistic studies on their membrane perturbation. Bioorg. Med. Chem. 1997, 5:2251-2265.
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 2251-2265
    • Ohnishi, Y.1    Tachibana, K.2
  • 281
    • 84986705345 scopus 로고
    • Synthesis of the sulfated steroidal glycosides forbeside E3 and E1
    • Jiang Z.-H., Han X.-B., Schmidt R.R. Synthesis of the sulfated steroidal glycosides forbeside E3 and E1. Liebigs Ann. Chem. 1993, 1179-1184.
    • (1993) Liebigs Ann. Chem. , pp. 1179-1184
    • Jiang, Z.-H.1    Han, X.-B.2    Schmidt, R.R.3
  • 282
    • 84885816158 scopus 로고    scopus 로고
    • Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside
    • Liu Q., Yu Y., Wang P., Li Y. Synthesis of analogues of linckoside B, a new neuritogenic steroid glycoside. New J. Chem. 2013, 37:3647-3661.
    • (2013) New J. Chem. , vol.37 , pp. 3647-3661
    • Liu, Q.1    Yu, Y.2    Wang, P.3    Li, Y.4
  • 283
    • 84978894081 scopus 로고
    • Synthesis of the hexasaccharide moiety of pectinioside E
    • Jiang Z.-H., Schmidt R.R. Synthesis of the hexasaccharide moiety of pectinioside E. Liebigs Ann. Chem. 1992, 975-982.
    • (1992) Liebigs Ann. Chem. , pp. 975-982
    • Jiang, Z.-H.1    Schmidt, R.R.2
  • 284
    • 84988119566 scopus 로고
    • Synthesis of the hexasaccharide moiety of the saponin holotoxin A
    • Han X.-B., Jiang Z.-H., Schmidt R.R. Synthesis of the hexasaccharide moiety of the saponin holotoxin A. Liebigs Ann. Chem. 1993, 853-858.
    • (1993) Liebigs Ann. Chem. , pp. 853-858
    • Han, X.-B.1    Jiang, Z.-H.2    Schmidt, R.R.3
  • 285
    • 84884205304 scopus 로고    scopus 로고
    • Synthesis of the pentasaccharide moiety of thornasterside A
    • Xiong J., Lu Z., Ding N., Ren S., Li Y. Synthesis of the pentasaccharide moiety of thornasterside A. Eur. J. Org. Chem. 2013, 6158-6166.
    • (2013) Eur. J. Org. Chem. , pp. 6158-6166
    • Xiong, J.1    Lu, Z.2    Ding, N.3    Ren, S.4    Li, Y.5
  • 286
    • 0025127955 scopus 로고
    • Novel sulfated sterol glycosides from Asterias forbesi
    • Findlay J.A., He Z.-Q. Novel sulfated sterol glycosides from Asterias forbesi. J. Nat. Prod. 1990, 53:710-712.
    • (1990) J. Nat. Prod. , vol.53 , pp. 710-712
    • Findlay, J.A.1    He, Z.-Q.2
  • 288
    • 0035114469 scopus 로고    scopus 로고
    • Studies on the constituents of Chenopodium quinoa seeds: Isolation and characterization of new triterpene saponins
    • Dini I., Schettino O., Simioli T., Dini A. Studies on the constituents of Chenopodium quinoa seeds: Isolation and characterization of new triterpene saponins. J. Agric. Food Chem. 2001, 49:741-746.
    • (2001) J. Agric. Food Chem. , vol.49 , pp. 741-746
    • Dini, I.1    Schettino, O.2    Simioli, T.3    Dini, A.4
  • 290
    • 40549101093 scopus 로고    scopus 로고
    • The de novo synthesis of oligosaccharides: Application to the medicinal chemistry SAR-study of digitoxin
    • Zhou M., O'Doherty G. The de novo synthesis of oligosaccharides: Application to the medicinal chemistry SAR-study of digitoxin. Curr. Top. Med. Chem. 2008, 8:114-125.
    • (2008) Curr. Top. Med. Chem. , vol.8 , pp. 114-125
    • Zhou, M.1    O'Doherty, G.2


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