Synthetic glycosides and glycoconjugates of low molecular weight natural products

Current Pharmaceutical Design

Volumn 22, Issue 12, 2016, Pages 1592-1627

  Grynkiewicz, G ^a   Szeja, W ^b  

^a INDUSTRIAL CHEMISTRY RESEARCH INSTITUTE   (Poland)

^b SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Chemical glycosidation; Glycolipids; Isoprenoid glycosides; Natural products; Plant phenolics; Secondary metabolite glycosides

Indexed keywords

ACTEOSIDE; ALKYL GLYCOSIDE; ANTHRACYCLINE DERIVATIVE; CARDIAC GLYCOSIDE; CURCUMIN; DIGITOXIN; DOCETAXEL; GENISTEIN; GLUCOSINOLATE; GLYCOCONJUGATE; GLYCOLIPID; GLYCOSIDE; GLYCOSPHINGOLIPID; GLYCOSYL GLYCEROL; HEDERAGENIN; ISOPRENOID; MORPHINE; NATURAL PRODUCT; NATURAL PRODUCTS AND THEIR SYNTHETIC DERIVATIVES; OLEANOLIC ACID; OSW 1; PACLITAXEL; PODOPHYLLOTOXIN; QS 21; QUERCETIN; RESVERATROL; SILIBININ; THIOCOLCHICOSIDE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT;

ACYLATION; ALCOHOLYSIS; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL LINE; CHEMICAL BOND; CHEMICAL MODIFICATION; CYTOTOXICITY; DRUG DNA BINDING; DRUG MECHANISM; DRUG STRUCTURE; GLUCURONIDATION; GLYCOSIDATION; GLYCOSYDATION; GLYCOSYLATION; HEART PROTECTION; HUMAN; HYDROPHILICITY; HYDROPHOBICITY; IN VITRO STUDY; MEDICINAL CHEMISTRY; MOLECULAR WEIGHT; NONHUMAN; OXIDATION; PHYTOCHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; SECONDARY METABOLISM; SYNTHESIS;

ANIMALS; BIOLOGICAL PRODUCTS; GLYCOCONJUGATES; GLYCOSIDES; HUMANS; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; SECONDARY METABOLISM;

EID: 84964262312     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612822666151211094345     Document Type: Article

References (362)

1. Lehmann J. Carbohydrates: Structure and biology. Stuttgart and New York: Thieme 1998.
2. Taylor ME, Drickamer K. Introduction to glycobiology: Oxford: Oxford University Press 2003.
3. Taniguchi N et al. (Eds.) Glycoscience: Biology and Medicine. Tokyo: Springer Japan 2015.
4. Demchenko AV, Ed. Handbook of chemical glycosylation. Advances in stereoselectivity and therapeutic Relevance. Weinheim: Wiley-VCH 2008.
5. Levy DE, Fügedi P. The organic chemistry of sugars. Boca Raton, London, New York: Taylor& Francis 2006.
6. Fraser-Reid B, Tatsuta K, Thiem, J, Eds. Glycoscience; Chemistry and Biology. Berlin: Springer 2008.
7. Kovac P, Ed. Carbohydrate Chemistry. Proven Synthetic Methods vol1. Boca Raton London New York: CRC Press Taylor&Francis Group 2012.
8. van der Marel G, Codee J, Eds. Carbohydrate Chemistry. Proven Synthetic Methods, vol 2. Boca Raton London New York: CRC Press Taylor&Francis Group 2014.
9. Ken V. Glycoside vs. aglycon: The Role of glycosidic residue in biological activity. In: Glycoscience. Fraser-Reid B, Tatsuta K, Thiem J. Eds. Berlin Heidelberg: Springer Verlag 2008.
10. Renaudet O, Spinelli N, Synthesis and Biological Applications of Glycoconjugates. New York: Bentham Science Publishers 2011
11. Gambert U, Thiem J. Chemical Transformations Employing Glycosyltransferases. In: Driguez H, Thiem J, Eds. Glycoscience. Synthesis of Oligosaccharides and Glycoconjugates. Berlin Heidelberg New York: Springer-Verlag 1999; pp. 21-43.
12. Taniguchi N, Honke K, Fukuda M, et al. Eds. Handbook of Glycosyltransferases and Related Genes. New York: Springer 2014.
13. Schmaltz RM, Hanson SR, Wong CH. Enzymes in the synthesis of glycoconjugates. Chem Rev 2011; 111: 4259-307.
14. Varki A. Nothing in glycobiology makes sense, except in the light of evolution. Cell 2006; 126: 851-4
15. Garegg PJ, Synthesis and reactions of glycosides. Adv Carbohydr Chem Biochem 2004; 59: 69-134.
16. Fügedi P. Glycosylation methods. In: Levy DE, Fügedi P. The organic chemistry of sugars. Boca Raton, London, New York: Taylor& Francis 2006.
17. Thiem J, Klaffke W. Synthesis of deoxy oligosaccharides. Top Curr Chem 1990; 154: 285-333.
18. Hou D, Lowary TL. Recent advances in the synthesis of 2-deoxyglycosides. Carbohydr Res 2009; 344: 1911-40.
19. Bongat AFG, Demchenko AV. Recent trends in the synthesis of Oglycosides of 2-amino-2-deoxysugars. Carbohydr Res 2007; 342: 374-406.
20. Toshima K. Novel glycosylation methods and their application to natural products synthesis. Carbohydr Res 2006; 341: 1282-97.
21. Gomez AM, Lobo F, Miranda S, et al. A survey of 2, 3-dideoxyhex-2-enopyranosides. Molecules 2015; 20: 8357-94.
22. Stachulski AV, Harding JR, Lindon JC, et al. Acyl glucuronides: Biological activity, chemical reactivity, and chemical synthesis. J Med Chem 2006; 49: 6931-45.
23. Křen V, Martinkova L. Glycosides in medicine: The role of glycosidic residue in biological activity. Cur Med Chem 2001; 8: 1303-28
24. Fraser-Reid B, Tatsuta K, Thiem J, Eds. Glycoscience; Chemistry and Biology. Berlin: Springer 2008: pp. 699-736.
25. Danishefsky SJ, Bilodeau MT. 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: 1380-419.
26. Aljahdali AZ, Shi P, Zhong Y, O'Doherty GA. De novo asymmetric synthesis of the pyranoses: From monosaccharides to oligosaccharides. Adv Carbohydr Chem Biochem 2013; 69: 55-123.
27. Gomez AM, Lobo F, Miranda S, et al. A survey of recent synthetic applications of 2, 3-dideoxy-hex-2-enopyranosides. Molecules 2015; 20: 8357-94.
28. Snader W. Drug Discovery; A History. Chichester: John Wiley & Sons, Ltd. 2005: pp. 106-107 and 357-60.
29. Stone E. An account of the success of the bark of the willow in the cure of agues. Phil Trans R Soc Lond A 1763; 53: 195-200.
30. Irvine JC, Rose RE. Constitution of salicin. Synthesis of pentamethyl salicin. J Chem Soc 1906; 89: 814-22.
31. An C, Mou Z. Salicylic acid and its function in plant immunity. J Integr Plant Biol 2011; 53: 412-26.
32. Rivas-San Vicente M, Plasencia J, Salicylic acid beyond defense: its role in plant growth and development. J Exp Botany 2011; 62: 3321-38.
33. Grynkiewicz G, Achmatowicz O, Hennig J, et al. Synthesis and characterization of the salicylic acid-D-glucopyranoside. Polish J Chem 1993; 67: 1251-54.
34. Jacob JN, Badyal DK, Bala S. Evaluation in the in-vivo anti inflammatory and analgesic activity of a highly water-soluble aspirin conjugate. Basic Clin Pharmacol Toxicol 2013; 112: 171-4.
35. Hanessian S, Mascitti V, Lu PP, et al. One-step stereocontrolled synthesis of α-anomeric carboxylic acid esters from unprotected glycosyl donors: A water-soluble aspirin pro-drug analogue. Synthesis 2002; 1959-68.
36. Chupakhina TA, Astrakhantseva AA, Kuryanov VO. Specific features of phase transfer catalytic glycosylation of aromatic hydroxy acids. Russian J Bioorg Chem 2013; 39: 306-11.
37. Aggarwal BB, Surh Y-J, Shisodia S, Eds. The molecular targets and therapeutic uses of curcumin in health and disease. New York: Springer 2007.
38. Grynkiewicz G, lifirski P. Curcumin and curcuminoids in quest for medicinal status. Acta Biochim Pol 2012; 59: 201-12.
39. Jitoe-Masuda A, Fujimoto A, Masuda T. Curcumin: from chemistry to chemistry based functions. Curr Pharm Des 2013; 19: 2084-92.
40. Bairwa K, Grover J, Kania M, et al. Recent developments in chemistry and biology of curcumin analogues. RSC Adv 2014; 4: 13946-78.
41. Parwathy KS, Srinivas P. Ultrasound-assisted reaction of 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide with potassium salt of curcumin under PTC conditions. Ultrasonics Sonochem 2008; 15: 571-7.
42. Gadad S, Bharati K, Parvathy S, et al. Curcumin-glucoside, a novel synthetic derivative of curcumin, inhibits α-synuclein oligomer formation relevance to Parkinson’s disease. Curr Pharm Des 2012; 18: 76-84.
43. Singh VK, Yadav P, Tadiggopula N. Recent advances in the synthesis, chemical transformations and pharmacological studies of some important dietary spice’s constituents. Chem Biol Interface 2014; 4: 66-99.
44. Rao AR, Prasad E, Deepthi SS, et al. Synthesis and biological evaluation of glucosyl curcuminoids. Ach Pharm Chem Life Sci 2014; 347: 834-9.
45. Mohri K, Watanabe Y, Yoshida Y, et al. Synthesis of glycosylcurcuminoids. Chem Pharm Bull 2003; 51: 1268-72.
46. Wojtkielewicz A. Application of cross metathesis in diene and polyene synthesis. Curr Org Synth 2013; 10: 43-66.
47. Setchell KDR. Phytoestrogens: the biochemistry, physiology, and implications for human health of soy isoflavones Am J Clin Nutr 1998; 68: 1333S-46S.
48. Veitch N. Isoflavonoids of the Leguminosae. Nat Prod Rep 2007; 24: 417-64.
49. Preedy VR, Ed. Isoflavones. Chemistry, analysis, function and effects. Cambridge: RSC Publishing 2013.
50. Dixon RA, Ferreira D. Genistein. Phytochem 2002; 60: 205-11.
51. Akiyama T, Ishida J, Nakagawa S, et al. Genistein, a specific inhibition of tyrosine-specific protein kinases. J Biol Chem 1987; 262: 5592-5.
52. Squadrito F, Bitto A. Genistein Chemistry and biochemistry. In: Preedy VR, Ed. Isoflavones. Chemistry, Analysis, Function and Effects. Cambridge: RSC Publishing 2013: pp. 148-56.
53. Setchell KDR, Brown NM, Desai P, et al. Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements. J Nutr 2001; 131: 1362S-7S.
54. Ullmann U, Metzner J, Frank T, et al. Safety, tolerability and pharmacokinetics of single ascending doses of synthetic genistein (Bonistein) in healthy volunteers. Adv Ther 2005; 22: 65-78.
55. Rusin A, Krawczyk Z, Grynkiewicz G, et al. Synthetic derivatives of genistein, their properties and possible applications Acta Biochim Polon 2010; 57: 23-34.
56. Rahman S, Islam R, Swaraz AM, et al. An insight on genistein as potential pharmacological and therapeutic agent. Asian Pacif J Trop Biomed 2012; 1924-37.
57. Lewis P, Kaltia S, Wähälä K. The phase transfer catalysed synthesis of isoflavone-O-glucosides. J Chem Soc Perkin Trans 1 1998; 2481-4.
58. Needs PW, Williamson G. Syntheses of daidzein-7-yl-Dglucopyranosiduronic acid and daidzein-4, 7-yl di--Dglucopyranosiduronic acid. Carbohydr Res 2001; 330: 511-5.
59. Li M, Han X, Yu B. Lipid-packaged linear iron(II) triazole complexes in solution: Controlled spin conversion via solvophobic selfassembly. J Org Chem 2003; 68: 6842-5.
60. Al-Maharik N, Botting NP. An efficient method for the glycosylation of isoflavones. Eur J Org Chem 2008; 106: 5622-9.
61. Sun J, Yu B, Yang X. Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods. Acc Chem Res 2012; 45: 1227-36.
62. Polkowski K, Popiolkiewicz J, Krzeczyski P, et al. Cytostatic and cytotoxic activity of synthetic genistein glycosides against human cancer cell lines. Cancer Lett 2004; 203: 59-69.
63. Rusin A, Gogler A, Gowala-Kosiska M, et al. Unsaturated genistein disaccharide glycoside as a novel agent affecting microtubules. Bioorg Med Chem Lett 2009; 19: 4939-43.
64. Szeja W, Puchaka J, wierk P, et al. Selective alkylation of genistein and daidzein. Chem Biol Interface 2013; 3: 95-106
65. Grynkiewicz G, Szeja W, Krzeczyski P, et al. Hexenoses in design of glycoconjugates-from chemistry to function. Chem Biol Interface 2014; 4: 301-20.
66. Byczek A, Zawisza-Puchalka J, Gruca A, et al. Genistein derivatives regioisomerically substituted at 7-O-and 4’-O-Have different effect on the cell cycle. J Chem 2014; Article ID: 191563.
67. Szeja W, wierk P, Rusin A, et al. An approach to C-glycosidic conjugates of isoflavones. Heterocyclic Communications 2013; 19: 133-8.
68. Griffith JQ, Krewson CF, Naghski J. Rutin and related flavonoids. Easton: Mack Publ. Co. 1955; pp. 1-52.
69. Veitch NC, Grayer RJ. Flavonoids and their glycosides, including anthocyjanins. Nat Prod Rep 2008; 25: 555-611.
70. Chua LS. A review on plant-based rutin extraction methods and its pharmacological activities. J Ethnopharmacol 2013; 150: 805-17.
71. Yang J, Guo J, Yuan J. In vitro antioxidant properties of rutin. LWT 2008; 41: 1060-6.
72. Branco de Araujo MEM, Franco YEM, Alberto TG, et al. Enzymatic de-glycosylation of rutin improves its antioxidant and antiproliferative activities. Food Chem 2013; 141: 266-73.
73. Wang J, Zhao LL, Sun GX, et al. A comparison of acidic and enzymatic hydrolysis of rutin. African J Biotech 2011; 10: 1460-6.
74. Wang Y, Ma YL, Wu XY, et al. Selective hydrolysis by commercially available hesperidinase for isoquercitrin production. J Mol Catal B: Enzymatic 2012; 81: 37-42.
75. Xu JD, Zhang LW, Liu YFa. Synthesis and antioxidant activities of flavonoid derivatives, troxerutin and 3’, 4’, 7-triacetoxyethoxyquercetin. Chin Chem Lett 2013; 24: 223-6.
76. Suzuki Y, Suzuki K. Enzymatic formation of 4G-α-Dglucopyranosyl rutin. Agric Biol Chem 1991; 55: 181-7.
77. Kajjout M, Rolando C. Regiospecific synthesis of quercetin O--Dglucosylated and-O--D-glucuronidated isomers. Tetrahedron 2011; 67: 4731-41.
78. Kajjout M, Zemmouri R, Rolando C. An expeditious synthesis of quercetin 3-O--D-glucuronide from rutin. Tetrahedron Lett 2011; 52: 4738-41.
79. Stähelin HF, von Wartbug A. From podophyllotoxin glucoside to etoposide. Progr Drug Res 1989; 33: 169-266.
80. Imbert TF. Discovery of podophylotoxins. Biochimie 1998; 80: 207-22.
81. Canel C, Moraes RM, Dayan FE, et al. Podophylotoxin. Phytochemistry 2000. 54: 115-20.
82. Henwood JM, Brodgen RN. Etoposide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in combination therapy of cancer. Drugs 1990; 39: 438-90.
83. Stähelin HF. 4’-Demethyl-epipodophyllotoxin thenylidene glucoside, a Podophyllum compound with a new mechanism of action. Eur J Cancer 1970; 6: 303-11
84. Hande KR. Etoposide: four decades of development of a topoisomerase II inhibitor. Eur J Cancer 1998; 34: 1514-21.
85. Henwood JM, Brodgen RN. Etoposide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in combination therapy of cancer. Drugs 1990; 39: 438-90.
86. Berkowitz DB, Choi S, Bhuniya D, et al. Novel “reverse Kahanetype glycosylation”: access to O-, N-, and C-linked epipodophylotoxin conjugates. Org Lett 2000; 2: 1149-52.
87. Vogel K, Sterling J, Herzig Y, et al.α-1-Tributyltin-O-2, 3-bisacetyl-4, 6-ethylidene-glucose as a convenient glycosidation reagent: an efficient synthesis of etoposide. Tetrahedron 1996; 52: 3049-56.
88. Allevi P, Anastasia M, Ciuffreda P, et al. Stereoselective glucosidation of Podophyllum lignans. A new simple synthesis of etoposide. J Org Chem 1993; 58: 4175-8.
89. Silverberg LJ, Kelly S, Vemishetti P, et al. A crystallizationinduced stereoselective glycosidation reaction in the synthesis of the anticancer drug etoposide. Org Lett 2000; 2: 3281-3.
90. Wu Y, Zhang H, Zhao Y, et al. A new and efficient strategy for the synthesis of podophyllotoxin and its analogues. Org Lett 2007; 9: 1199-202.
91. Sellars J, Steel PG. Advances in the synthesis of aryltetralin lignin lactones. Eur J Org Chem 2007; 3815-28.
92. Ward RS. Different strategies for the chemical synthesis of lignans. Phytochem Rev 2003; 2: 391-400.
93. Bush EJ, Jones DW. Asymmetric total synthesis of (-) podophyllotoxin. J Chem Soc Perkin Trans 1 1995; 1489-92.
94. Engelhardt U, Sarkar A, Linker T. Synthesis of (-)-epipodophyllotoxin. Angew Chem Int Ed 2003; 42: 2487-9.
95. Casey M, Keaveney CM. A concise stereocontrolled formal total synthesis of (±)-podophyllotoxin using sulfoxide chemistry. Chem Commun 2004; 184-5.
96. Malik S, Biba O, Gruz J, et al. Biotechnological approaches for producing aryltetralin lignans from Linum species. Phytochem Rev 2014; 13: 893-913.
97. Bruschi M, Orlandi M, Rindone M, et al. Podophyllotoxin and antitumor synthetic aryltetralines. Toward a biomimetic preparation. In: Mukherjee A, Ed. Biomimetics Learning from Nature. Rijeka: InTech 2010.
98. Magoulas GE, Papaioannou D, Bioinspired syntheses of dimeric hydroxycinnamic acids (Lignanas) and hybrids, using phenol oxidative coupling as key reaction, and medicinal significance thereof. Molecules 2014; 19: 19769-835.
99. Biedermann D, Vavříková E, Cvak L, et al. Chemistry of silybin. Nat Prod Rep 2014; 31: 1138-57.
100. Monti D, Gažák R, Marhol P, et al. Enzymatic kinetic resolution of silybin diastereoisomers. J Nat Prod 2010; 73: 613-9.
101. Gažák RP, Marhol K, Purchartová K. Large-scale separation of silybin diastereoisomers using lipases. Proc Biochem 2010; 45: 1657-63.
102. Marhol P, BednárP, Kolárová P, et al. Pharmacokinetics of pure silybin diastereoisomers and identification of their metabolites in rat plasma. J Funct Foods 2015; 14: 570-80
103. Huseini HF, Larijani B, Heshmat R, et al. The efficacy of silybum marianum (L.) Gaertn. (silymarin) in the treatment of type II diabetes: a randomized, double-blind, placebo-controlled, clinical trial. Phytother Res 2006; 20: 1036-9.
104. Sak K. Cytotoxicity of dietary flavonoids on different human cancer types. Pharmacogn Rev 2014; 8: 122-46.
105. Millimouno FM, Dong J, Yang L, et al. Targeting Apoptosis Pathways in Cancer and Perspectives with natural compounds from mother nature. Cancer Prev Res (Phila). 2014; 7: 1081-1107.
106. Yadegarynia S, Pham A, Ng A, et al. Profiling flavonoid cytotoxicity in human breast cancer cell lines: determination of structurefunction relationships. Nat Prod Commun 2014; 9: 597-606.
107. Martinez-Perez C, Ward C, Cook G, et al. Novel flavonoids as anti-cancer agents: mechanisms of action and promise for their potential application in breast cancer. Biochem Soc Trans 2014; 42: 1017-23.
108. Wang HJ, Tashiro S, Onodera S, Ikejima T. Inhibition of insulinlike growth factor 1 receptor signaling enhanced silibinin-induced activation of death receptor and mitochondrial apoptotic pathways in human breast cancer MCF-7 cells. J Pharmacol Sci 2008; 107: 260-9.
109. Jayaraj R, Deb U, Bhaskar AS, et al. Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice. Environ Toxicol 2007; 22: 472-9.
110. Dehmlow C, Erhard J, de Groot H. Inhibition of Kupffer cell functions as an explanation for the hepatoprotective properties of silibinin. Hepatology 1996; 23: 749-54.
111. Trompier D, Baubichon-Cortay H, Chang XB, et al. Multiple flavonoid binding sites within multidrug resistance protein MRP1. Cell Mol Life Sci 2003; 60: 2164-77.
112. Huseini HF, Larijani B, Heshmat R, et al. The efficacy of Silybum marianum (L.) Gaertn. (silymarin) in the treatment of type II diabetes: a randomized, double-blind, placebo-controlled, clinical trial. Phytother Res 2006; 20: 1036-9.
113. Theodosiou E, Purchartová K, Stamatis H, et al. Bioavailability of silymarin flavonolignans: Drug formulations and biotransformation. Phytochem Rev 2014; 13: 1-18.
114. Voinovich D, Perissutti B, Grassi M, et al. Solid state mechanochemical activation of Silybum marianum dry extract with beta cyclodextrins: Characterization and bioavailability of the coground systems. J Pharm Sci 2009; 98: 4119-29.
115. Křen V, Kubisch J, Sedmera P, et al. Glycosylation of silybin. J Chem Soc Perkin Trans 1 1997; 2467-74.
116. Křen V, Minghetti A, Sedmera P, et al. Glucosylation of silybin by plant-cultures of Papaver somniferum var. setigerum. Phytochemistry 1998; 47: 212-20.
117. Křen V, Găzak R, Purchartova K, et al. Chemoenzymatic preparative separation of silybins A and B. J Mol Catal B Enzym 2009; 61: 247-51.
118. Charriera C, Azerada R, Marholc P, et al. Preparation of silybin phase II metabolites: Streptomyces catalyzed glucuronidation. J Molr Catal B Enzym 2014; 102: 167-73.
119. Găzak R, Marhola P, Purchartova K, et al. Large-scale separation of silybin diastereoisomers using lipases. Proc Biochem 2010; 45: 1657-63.
120. Osborne R. The analgesic activity of morphine 6-glucuronide. Br J Clin Pharm 1992; 34: 130-8.
121. Christrup LL. Morphine metabolites. Acta Anesthesiol Scand 1997; 41: 116-22.
122. Kroemer HK, Klotz U. Glucuronidation of Drugs. Clin Pharmacokin 1992; 23: 292-310.
123. Stachulski AV, Jenkins GN. The synthesis of O-glucuronides. Nat Prod Rep 1998; 15: 173-86.
124. Berrang B, Twine CE, Hennessee GL, et al. Synthesis of morphine 3-glucuronide. Synth Commun 1975; 5: 231-6.
125. Lacy C, Sainsbury M. A synthesis of morphine 6-glucuronide. Tetrahedr Lett 1995; 36: 3949-50.
126. Rukhman I, Gutman AL. Synthesis of morphine 6--Dglucuronide. Tetrahedron Lett 2000; 41: 6889-92.
127. Brown RT, Carter NE, Mayalarp SP, et al. A simple synthesis of morphine 3, 6-di--D-glucuronide. Tetrahedron 2000; 56: 7591-4.
128. Kiang TKL, Ensom MHH, Chang TKH. UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Therapeut 2005; 106: 97-132.
129. Shipkova M, Wieland E. Glucuronidation in therapeutic drug monitoring. Clin Chim Acta 2005; 358: 2-23.
130. Ritter JK. Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem-Biol Interact 2000; 129: 171-93.
131. Regev-Shoshani G, Shoseyov O, Bilkis I, et al. Glycosylation of resveratrol protects it from enzymic oxidation. Biochem J 2003; 374: 157-63.
132. Walle T, Hsieh F, DeLegge MH, et al. High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab Dispos 2004; 32: 1377-82.
133. Soleas GJ, Yan J, Goldberg DM. Ultrasensitive assay for three polyphenols (catechin, quercetin and resveratrol) and their conjugates in biological fluids utilizing gas chromatography with mass selective detection. J Chromatogr B: Biomed Sci Appl 2001; 757: 161-72.
134. Athar M, Ho Back J, Tang X, et al. Resveratrol: a review of toxicology and applied pharmacology. Toxicol Appl Pharmacol 2007; 224: 274-83.
135. Pervaiz S, Holme AL. Resveratrol: its biologic targets and functional activity. Antioxid Redox Signal 2009; 11: 2851-97.
136. Hung LM, Chen JK, Huang SS, et al. Cardioprotective effect of resveratrol, a natural antioxidant derived from grapes. Cardiovasc Res 2000; 47: 549-55.
137. Surh Y. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat Res 1999; 428: 305-27.
138. Bhat KPL, Kosmeder JW II, Pezzuto JM. Biological effects of resveratrol. Antioxid Redox Signaling 2001; 3: 1041-64.
139. Sun W, Wang W, Kim J, et al. Anti-cancer effect of resveratrol is associated with induction of apoptosis via a mitochondrial pathway alignment. Adv Exp Med Biol 2008; 614: 179-86.
140. Fulda S. Resveratrol and derivatives for the prevention and treatment of cancer. Drug Discov Today 2010; 15: 757-64.
141. Mitchell H, Keylor MH, Matsuura BS, et al. Chemistry and biology of resveratrol-derived natural products. Chem Rev 2015; 115(17): 8976-9027.
142. Li Y, Mo H, Lian B, et al. Revisit of the phenol O-glycosylation with glycosyl imidates, BF3 OEt2 is a better catalyst than TMSOTf. Carbohydr Res 2012; 363: 14-22.
143. Lucas R, Alcantara D, Morales JC. A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol and hydroxytyrosol. Carbohydr Res 2009; 344: 1340-6.
144. Aitken HRM, Johannes M, Looms KM, et al. Synthesis of leptosin, a glycoside isolated from mnuka honey. Tetrahedron Lett 2013; 54: 6916-9.
145. Seibel J, Hilringhaus L, Moraru R. Microwave-asisted glycosylation for the synthesis of.glycopeptides. Carbohydr Res 2005; 340: 507-11.
146. Zhang Z, Yu B, Schmidt RR. Synthesis of mono-and di-O-β-Dglucopyranoside conjugates of E-resveratrol. Synthesis 2006; 1301-6.
147. Marzag H, Robert G, Dufies M, et al. FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs. Ultrason Sonochem 2015; 22: 15-21.
148. Marvalina C, Azerada R. Microbial glucuronidation of polyphenols. J Mol Catal B Enzym 2011; 73: 43-52.
149. Wyat DK, Grady LT, Sun S. Colchicine. Anal Prof Drug Subst 1981; 10: 139-82
150. Jana S, Shekhawat GS. Critical view on medicinally potent plant species: Gloriosa superba. Fitoterapia 2011; 82: 293-301.
151. Graening T, Schmaltz H-G. Total syntheses of colchicines in comparison: a journey through 50 years of synthetic organic chemistry. Angew Chem Int Ed 2004; 43: 3240-56.
152. Reuter S, Gupta SC, Phromnoi K, et al. Thiocolchicoside suppresses osteoclastogenesis induced by RANKL and cancer cell through inhibition of inflammatory pathways: a new use for an old drug. Br J Pharmacol 2012; 165: 2127-39.
153. Ashrafuzzaman M, Duszyk M, Tuszynski JA. Chemotherapy drugs thiocolchicoside and taxol permeabilize lipid bilayer membranes by forming ion pores. J Phys Conf Ser 2011; 329: 012029.
154. Reuter S, Prasad S, Phromnoi K. et al. Thiocolchicoside exhibits anticancer effects through downregulation of NF-kB pathway and its regulated gene products linked to inflammation and cancer. Cancer Prev Res 2010; 3: 1462-72.
155. Lettello C, The pharmacology and therapeutic aspects of colchicines. Alkaloids 2000; 53: 287-352.
156. Achmed A, Peters NR, Fitzgerald MK. et al. Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action. J Am Chem Soc 2006; 128: 14224-5.
157. Fu GM, Pang H, Wong YH. Naturally occurring phenylethanoid glycosides: potential leads for new therapeutics. Curr Med Chem 2008; 15: 2592-613.
158. Jimenez C. Riguera R. Phenylethanoid glycosides in plants: structure and biological activities. Nat Prod Rep 1994; 591-606.
159. Yu P, Hu C, Meehan EJ, et al. X-Ray crystal structureand antioxidant activity of salidroside, a phenylethanoid glycoside. Chem Biodivers 2007; 4: 508-11.
160. Alipieva K, Korkina L, Erdogan Orhan I, et al. Verbascoside-a review of its occurrence, (bio)synthesis and pharmacological significance. Biotech Adv 2014; 32: 1065-76.
161. Duynstee HI, De Koning MC, Ovaa H, et al. Synthesis of verbascoside: a dihydroxyphenethyl glycoside with diverse bioactivity. Eur J Org Chem 1999; 2623-32.
162. Kawada T, Asano R, Hayashida S, et al. Total synthesis of the phenylpropanoid glycoside, acteoside. J Org Chem 1999; 64: 9268-71.
163. Mulani SK, Guh J-H, Mong K-K T. A general strategy and the anti-proliferation properties on prostate cancer cell lines for natural phenylethanoid glycosides. Org Biomol Chem 2014; 12: 2926-37.
164. Arcamone F. Doxorubicin, Anthracycline Antibiotics. New York London Toronto: Academic Press 1981.
165. Nadas J, Sun D. Anthracyclines as effective anticancer drugs. Expert Opin Drug Discov 2006; 1: 549-68.
166. Brockmann H. Anthracyclinone and anthracycline (rhodomycinone, pyrromycinone, and their glycosides). Fortschr Chem Org Naturst 1963; 21: 121-82.
167. Arcamone F, Casinelli G. Biosynthetic anthracyclines. Curr Med Chem 1998; 5: 391-419.
168. Laatsch H, Fotso S. Naturally occurring anthracyclines. Top Curr Chem 2008; 282: 3-74.
169. Niell HB, Hunter RF, Herrod HG, et al. M. Cancer Chemother. Pharmacol 1987; 19: 47-52.
170. Zhang Y, Dai Y, Hou M, et al. Chemo-enzymatic synthesis of valrubicin using Pluronic conjugated lipase with temperature responsiveness in organic media. RSC Adv 2013; 3: 22963-6.
171. Koch TH, Barthel BL, Kalet BT, et al. Anthracycline-formaldehyde conjugates and their targeted prodrugs. Top Curr Chem 2008; 283: 141-70.
172. Acton EM, Tong GL, Mosher CW, et al. Wolgemuth RL. Intensly potent morpholinyl anthracyclines. J Med Chem 1984; 27: 638-45.
173. Farquhar D, Cherif A, Bakina E, et al. Intensely potent doxorubicin analogues: structure-activity relationship. J Med Chem 1998; 41: 965-72.
174. Arcamone F. Properties of antitumor anthracyclines and new developments in their application: Cain Memorial Award Lecture. Cancer Res 1985; 45: 5995-9.
175. Arcamone F-M. Fifty years of chemical research at Farmitalia. Chem Eur J 2009; 15: 7774-91.
176. Umezawa H, Takahashi Y, Kinoshita M, et al. Tetrahydropyranoyl derivatives of daunomycin and adriamycin. J Antib 1979; 32: 1082-4.
177. Bolitt V, Mioskowski C, Lee SG, et al. Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement. J Org Chem 1990; 55: 5812-3.
178. Yadav JS, Reddy BV, Bhaskar Reddy K, et al. CeCl3.7H2O: a novel reagent for the synthesis of 2-deoxysugars from D-glycals. Tetrahedron Lett 2002; 43: 7009-12
179. Grynkiewicz G, Fokt I, Skibicki P, et al. Synthesis of 1-O-silylated 3-azido-and 3-N-trifluoroacetamido-2, 3, 6-trideoxy-L-arabino and L-lyxo-hexopyranoses, convenient glycosyl donors for preparation of anthracycline antibiotics and related DNA-binding age. Polish J Chem 2005; 79: 335-47.
180. Fokt I, Grynkiewicz G, Skibicki P, et al. New strategies towards synthesis of doxorubicin analogs. Polish J Chem 2005; 79: 349-59.
181. Zhang G, Fang L, Zhu L, et al. Syntheses and biological activities of disaccharide daunorubicins. J Med Chem 2005; 48: 5269-78.
182. Cipollone A, Berettoni M, Bigioni M, et al. Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity. Bioorg Med Chem 2002; 10: 1459-70.
183. Arcamone F-M. Sabarubicin. Top Curr Chem 2008; 283: 171-83.
184. Varki A, Cummings RD, Esko JD, et al. Eds. Essential of Glycobiology. New York: Cold Spring Harbor Laboratory Press.
185. Subramaniam S, Fahy E, Gupta S, et al. Bioinformatics and systems biology of the lipidome. Chem Rev 2011; 111: 6452-90.
186. Schnar RL, Suzuki A, Stanley P, et al. Eds. Essential of Glycobiology, New York: Cold Spring Harbor Laboratory Press 2009; pp. 129-41.
187. Vill V, Hashim R. Carbohydrate liquid crystals: structure-property, relationship of thermotropic and lyotropic glycolipids. Curr Opin Colloid Interface Sci 2002; 7: 395-409.
188. Goodby JW, Gortz V, Cowling SJ, et al. Thermotropic liquid crystalline glycolipids J Chem Soc Rev 2007; 36: 1971-2032.
189. C.C. Ruíz, Ed. Sugar-based Surfactants-Fundamentals and Applications. Boca Raton: CRC Press, FL 2008.
190. Hashim R, Sugimura A, Minamikawa H, et al. Nature-like synthetically branched-chain glycolipids: a review on chemical structure and self-assembly properties. Liquid Crystals 2012; 39: 1-17.
191. Hill K, von Rybinski W, Stoll G. Alkyl Polyglycosides: Technology, Properties and Applications. Weinheim: VCH 1997.
192. Biosurfactants: Production and Utilization—Processes, Technologies, and Economics. Kosaric N, Vardar-Sukan F. Florida Boca Raton: CRC Press 2015.
193. Kralova I, Sjöblom J. Surfactants used in food industry. J Dispers Sci Technol 2009; 30: 1363-83.
194. LernerA, Matthias T. Changes in intestinal tight junction permeability associated with industrial food additives explain the rising incidence of autoimmune disease, Autoimmunity Rev 2015; 14: 479-89.
195. Ryan DA, Gin DY. Glycoside Synthesis from 1-Oxygen Substituted Glycosyl Donors. In: Demchenko AV. Ed. Handbook of Chemical Glycosylation. Weinheim: Wiley-VCH Verlag & Co. KGaA 2008; pp. 95-143.
196. Ferlin N, Grassi D, Ojeda C, et al. Synthesis of sugar-based chelating surfactants for metal removal from waste water. Carbohydr Res 2008: 343: 839-47.
197. van der Hejden AM, Lee TC, van Rantwijk F, et al. Glycosidation of fructose-containing disaccharides using MCM-41 material as the catalyst. Carbohydr Res 2002; 337: 1993-8.
198. von Rybinski W, Hill K. Alkyl Polyglycosides Properties and Applications of a new Class of Surfactants Angew. Chem Int Ed 1998, 37: 1328-45.
199. Ahmada N, Ramsch R, Meritxell Llinàs M, et al. Influence of nonionic branched-chain alkyl glycosides on a model nanoemulsion for drug delivery systems. Colloids Surfaces B: Biointerfaces 2014; 115: 267-74.
200. Dörmann, P, Benning C. Galactolipids role in seed plants. Trends Plant Sci 2002; 7: 112-8.
201. Jouhet J, et al. Glycerolipid transfer for the building of membranes in plant cells. Prog Lipid Res 2007; 46: 37-55.
202. Joyard J, et al. The biochemical machinery of plastid envelope membranes. Plant Physiol 1998; 118: 715-23.
203. Block MA. Preparation and characterization of membrane fractions enriched in outer and inner envelope membranes from spinach chloroplasts. II. Biochemical characterization. J Biol Chem 1983; 258, 3281-6.
204. Gounaris K, Barber J. Monogalactosyldiacylglycerol: the most abundant polar lipid in nature. Trends Biochem Sci 1983; 8: 378-81.
205. Mizusawa N, Wada H. The role of lipids in photosystem II. Biochim Biophys Acta 2012; 1817: 194-208.
206. Schleiff E, Soll J, Kuchler M, et al. Characterization of the translocon of the outer envelope of chloroplasts. J Cell Biol 2003; 160: 541-51.
207. Warnecke D, Heinz E. Glycolipid head group replacement: a new approach for the analysis of specific functions of glycolipids in vivo. Eur J Cell Biol 2010; 89: 53-61.
208. Wikstrom M, Kelly AA, Georgiev A, et al. Lipid-engineered Escherichia coli membranes reveal critical lipid head group size for protein function. J Biol Chem 2009; 284: 954-65.
209. Jones MR. Lipids in photosynthetic reaction centres: structural roles and functional holes. Prog Lipid Res 2007; 46: 56-87.
210. Carina IC, Crucho CIC, Correia-da-Silva P, et al. Recent progress in the field of glycoconjugates. Carbohydr Res 2015; 402: 124-32.
211. Mannock DA, Lewis RN, McElhaney RN. The chemical synthesis and physical characterization of 1, 2-di-O-acyl-3-O-(-Dglucopyranosyl)-sn-glycerols, an important class of membrane glycolipids. Chem Phys Lipids 1990; 55: 309-21.
212. Mannock DA, M. Akiyama M, Lewis RN at al. Synthesis and thermotropic characterization of a homologous series of racemic-D-glucosyldialkylglycerols, Biochim Biophys Acta 2000; 1509: 203-15.
213. Mannock DA, Collins MD, Kreichbaum M, et al. The thermotropic phase behaviour and phase structure of a homologous series of racemic-D-galactosyl dialkylglycerols studied by differential scanning calorimetry and X-ray diffraction. Chem Phys Lipids 2007; 148: 26-50.
214. Milkereit G, Gerber S, Brandenburg K, et al. Synthesis and mesomorphic properties of glycosyl dialkyl-and diacyl-glycerols bearing saturated, unsaturated and methyl branched fatty acid and fatty alcohol chains: Part I. Synthesis Chem Phys Lipids 2005; 135: 1-14.
215. Houlihan WJ, Lohmeyer M, Workman P, et al. Phospholipid antitumor agents. Med Res Rev 1995; 15: 157-223.
216. Marino-Albernas JR, Bittman R, Peters A, et al. Synthesis and Growth Inhibitory Properties of Glycosides of 1-O-Hexadecyl-2-Omethyl-sn-glycerol. Analogs of the Antitumor Ether Lipid ET-18-OCH3 (Edelfosfine). J Med Chem 1996; 39: 3241-7.
217. Pozsgay V, Kubler-Kielb J, Coxon B, et al. Synthesis and antigenicity of BBGL-2 glycolipids of Borrelia burgdorferi, the causative agent of Lyme disease. Carbohydr Res 2011; 346: 1551-63.
218. Ogretmen B, Hannun YA. Biologically active sphingolipids in cancer pathogenesis and treatment. Nat Rev Cancer 2004; 4: 604-11.
219. Saddoughi SA, Ogretmen B. Diverse functions of ceramide in cancer cell death and proliferation. Adv Cancer Res 2013; 117: 37-58.
220. Ponnusamy S, Meyers-Needham M, Senkal CE, et al. Sphingolipids and cancer: ceramide and sphingosine-1-phosphate in the regulation of cell death and drug resistance. Future Oncol 2010; 6: 1603-24.
221. Pérez SF, Schmidt RR. Total synthesis of a-galactosyl cerebroside, Carbohydr Res 2000; 328: 95-102.
222. Ndonye RM, Izmirian DP, Dunn MDF, et al. Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH. J Org Chem 2005; 70: 10260-70.
223. Plettenburg O, Bodmer-Narkevitch V, Wong C-H. Synthesis of-galactosyl ceramide, a potent immunostimulatory agent. J Org Chem 2002; 67: 4559-64.
224. Luo S-Y, Kulkarni SS, Chou C-H, et al. A concise synthesis of tetrahydroxy-LCB,-Galactosyl ceramide, and 1, 4-Dideoxy-1, 4-imino-L-ribitol via D-Allosamines as key building blocks. J Org Chem 2006; 71: 1226-29.
225. Merrill AH, Sphingolipid and glycosphingolipid metabolic pathways in the era of sphingolipidomics. Chem Rev 2011; 111: 6387-422.
226. M. Schombs FE, Park W, Du SS, et al. One-Pot syntheses of immunostimulatory glycolipids. J Org Chem 2010; 75 4891-98.
227. Bhat A, Gervay-Hague J. Efficient syntheses of-cyanosugarsusing glycosyl iodides derived from Per-O-silylated mono-and disaccharides. Org Lett 2001; 3: 2081-4.
228. Liu Z, Byun H-S, Bittman R. Synthesis of immunostimulatory-Cgalactosylceramide glycolipids via sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening. Org Lett 2010; 12: 2074-7.
229. Withering W. An account on the foxglove and some of its medical uses with practical remark on dropsy and other diseases. London: GGJ & J. Robinson 1785 In: Willius FA, Keys TE, Eds. Classics of Cardiology. New York: Dover Publ Inc. 1941; vol. 1: pp. 231-52.
230. Deepak D, Srivastava S, Khare NK, et al. Cardiac glycosides. Progr Chem Org Nat Prod 1996; 69: 71-155.
231. Sneader W. Drug discovery; A history. Chichester: John Wiley & Sons, Ltd. 2005; pp. 107-8.
232. Lichti H, Kuhn M, von Wartburg A. Zur Struktur der Zuckerkomponente des Digitoxins. Helv Chim Acta 1962; 45: 868-81.
233. Reichstein T, Weiss E. The sugars of the cardiac glycosides. Adv Carbohydr Chem 1963; 17: 65-120.
234. Albrecht HP. Mittel bei Herzinsuffizienz: Herzglycoside, In: Ullmann Encyclopädie der technischen Chemie-Weinheim: Verlag Chemie 1976; vol 12; pp. 617-32.
235. Hauptman PJ, Kelly RA. Digitalis. Circulation 1999; 99: 1265-70
236. Kaplan JH. Biochemistry of Na, K-ATPase. Annu Rev Biochem 2002; 71: 511-35.
237. Newman RA, Yang P, Pawlus AD, et al. Cardiac glycosides as novel cancer therapeutic agents. Mol Intervention 2008; 8: 36-49.
238. Jensen M, Schmidt S, Fedosova NU, et al. Synthesis and evaluation of cardiac glycoside mimics as potential anticancer drugs. Bioorg Med Chem 2011; 19: 2407-17.
239. Hamad E, Mather PJ, Srinivasan S, et al. Pharmacologic therapy of chronic heart failure. Am J Cardiovasc Drugs 2007; 7: 235-48.
240. Haustein KO, Megges R, Hauptmann J. Structure-activity relationship of natural and seminatural genins and glycosides as investigated on the smooth muscle of the guinea-pig ileum. Pharmacology 1973; 10: 65-75.
241. Schoner W. Endogenous cardiac glycosides, a new class of steroid hormones. Eur J Biochem 2002; 269: 2440-8.
242. Goto A, Yamada K. Ouabain-like factor. Curr Opin Nephrol Hypertens 1998; 7: 189-96.
243. Reyle K, Meyer K, Reichstein T. Partialsynthese von covallotoxin. Helv Chim Acta 1950; 33: 1541-6.
244. Renaudet O, Spinelli N, Eds. Synthesis and biological applications of glycoconjugates. USA: Bentham Science Publishers: eBook, 2011.
245. Nicolau KC, Mitchell HJ. Adventures in carbohydrate chemistry: new synthetic technologies, chemical synthesis, molecular design, and chemical biology. Angew Chem Int Ed 2001; 40: 1576-624
246. Lederkremer RM, Marino C. Deoxy sugars: occurrence and synthesis. Adv Carbohydr Chem Biochem 2007; 61: 143-216.
247. Marzabadi CH, Franck RW. The synthesis of 2-deoxyglycosides: 1988-1999. Tetrahedron 2000; 56: 8385-417.
248. Kirschning A, Bechthold, AFW, Rohr J. Chemical and biochemical aspects of deoxysugars and deoxysugar oligosaccharides. Top Curr Chem 1997; 188: 1-84.
249. Borovika A, Nagorny P. Recent advances in the synthesis of natural 2-deoxy--glycosides. J Carbohydr Chem 2012; 31: 255-83.
250. Yu B. Sun J. Current synthesis of triterpene saponins. Chem Asia J 2009; 4: 462-54.
251. Pellisier H. The glycosylation of steroids. Tetrahedron 2004; 60: 5123-62.
252. Issa JP, Bennett CS. A reagent controlled SN2-glycosylation for the direct synthesis of-linked 2-deoxy sugars. J Am Chem Soc 2014; 136: 5740-4.
253. Zhu D, Baryal KN, Adhikari S, et al. Direct synthesis of 2-deoxy--glycosides via anomeric O-alkylation with secondary electrophiles. J Am Chem Soc 2014; 136: 3172-5.
254. Yu B, Sun J, Yang X. Assembly of naturally occurring glycosides, evolved tactics and glycosylation methods. Acc Chem Res 2012; 45: 1227-36.
255. Yu B, Zhang Y, Tang P. Carbohydrate chemistry in the total synthesis of saponins. Eur J Org Chem 2007; 5145-65.
256. Zorbach WW, Gilligan WH. Partial synthesis of 1, 2-ciscardenolides. Carbohydr Res 1965; 1: 274-83.
257. Zorbach WW, Saeki S, Buhler W. Strophanthidin cardenolides containing hexoses of the mannose series. J Med Chem 1963; 6: 298-301.
258. Zorbach WW. Synthetic cardenolides. Adv Carbohydr Chem 1967; 21: 273-321.
259. Zorbach WW, Henderson N, Saekl S. 2-Deoxy Sugars. VI. Concurrent one-step formation of both anomeric monodigitoxosides of digitoxigenin. J Org Chem 1964; 29: 2016-7.
260. Zorbach WW, Payne TA. The partial synthesis of a monodigitoxoside of digitoxigenin. J Am Chem Soc 1959; 81: 1519-9.
261. Zorbach WW, Payne TA. 2-Deoxy Sugars. II. 3-(2, 6-Dideoxy--D-ribo-hexopyranosyl)-14-hydroxy-5-card-20(22)-enolide. A direct method of synthesis of 2-deoxyglycosides involving a crystalline 2-deoxy-acylglycosyl halide. J Am Chem Soc 1960; 82: 4979-83.
262. Baryal KN, Adhikar S, Zhu J. Catalytic stereoselective synthesis of-digitoxosides: direct synthesis of digitoxin and C1-epi-digitoxin. J Org Chem 2013; 78: 12469-76.
263. Beale TM, Taylor MS. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org Lett 2013; 15: 1358-6.
264. Tsai TYR, Haolun J, Wiesner K. A stereoselective synthesis of digitoxin. On cardioactive steroids. XIII. Can J Chem 1984; 62: 1403-5.
265. Wiesner K, Tsai TYR, Jin H. On cardioactive steroids XVI. Stereoselective-D-glycosylation of digitoxose: the synthesis of digitoxin Helv Chim Acta 1985; 68: 300-14.
266. McDonald FE, Subba Reddy K. Convergent synthesis of digitoxin: stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal. Angew Chem Int Ed 2001; 40: 3653-4.
267. Ma Y, Li Z, Shi H, et al. Assembly of digitoxin by gold(I)-catalysed glycosidation of glycosyl o-alkynyl benzoates. J Org Chem 2011; 76: 9748-56.
268. Tang Y, Li Y, Zhu Y, et al. Mechanistic insights into the gold(I)-catalysed activation of glycosyl ortho-alkynylbenzoates for glycosylation. J Am Chem Soc 2013; 135: 18396-405.
269. Zhou M, O’Doherty GA. A stereoselective synthesis of digitoxin and digitoxigen mono-and bisdigitoxide from digitoxigenin via a palladium-catalysed glycosylation. Org Lett 2006; 8: 4339-42.
270. Aljahdali AZ, Shi P, Zhong Y, et al. De novo asymmetric synthesis of the pyranoses: From monosaccharides to oligosaccharides. Adv Carbohydr Chem Biochem 2013; 69: 55-123.
271. Satheesh Babu R, Zhou M, O'Doherty GA. De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction. J Am Chem Soc 2004; 126: 3428-9.
272. Baryal KN, Adhikar S, Zhu J. Catalytic stereoselective synthesis of-digitoxosides: direct synthesis of digitoxin and C1-epi-digitoxin. J Org Chem 2013; 78: 12469-76.
273. Beale TM, Taylor MS. Synthesis of cardiac glycoside analogs by catalyst-controlled, regioselective glycosylation of digitoxin. Org Lett 2013; 15: 1358-61.
274. Suhr R, Pfefferkorn P, Weingarten S, et al. Synthesis of rhamnosylated diosgenyl glucosides as mimetics of cytostatic steroidal saponins from Ornithogalum saundersiae and Galtonia candicans. Org Biomol Chem 2003; 1: 4373-9.
275. Takechi M, Doi K, Wakayama Y. Biological activities of synthetic saponins and cardiac glycosides. Phytother Res 2003; 17: 83-5.
276. Kaskiw MJ, Tassotto ML, Th’ng J, et al. Synthesis and cytotoxic activity of diosgenyl saponin analogues. Bioorg Med Chem 2008; 16: 3209-17.
277. Wani MC, Taylor HL, Wall ME, et al. Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 1971; 93: 2325-7.
278. Nobili S, Lippib D, Witort E. Natural compounds for cancer treatment and prevention. Pharmacol Res 2009; 59: 365-78.
279. Cragg GM, Kingston DGJ, Newman DJ, Eds. Anticancer agents from natural products. 2nd ed. London New York: CRC Press Taylor& Francis 2012.
280. Schiff PB, Fant J, Horwitz SB, Promotion of microtubule assembly in vitro by taxol Nature 1979; 277: 665-7.
281. Jordan MA, Toso RJ, Thrower D. Mechanism of mitotic block and inhibition of cell proliferation by taxol at law cocncentrations. Proc Natl Acad Sci USA 1993; 90: 9552-6.
282. Wang Y-F, Shi Q-W, Dong M, et al. Natural taxanes: developments Since 1828. Chem Rev 2011; 111: 7652-709.
283. Denis J-N, Greene AE, Guenard D, et al. A highly efficient, practical approach to natural taxol. JAm Chem Soc 1988; 110: 5917-19.
284. Kingston DGJ. Taxol and Its Analogs. In: Cragg GM, Kingston DGJ, Newman DJ Eds. Anticancer agents from natural products. 2nd ed. London New York: CRC Press Taylor& Francis 2012; pp. 123-75.
285. Expósito O, Bonfill M, Moyano E, et al. Biotechnological production of taxol and related taxoids: current state and prospects. Anti-Cancer Agents Med Chem 2009; 9: 109-21.
286. Kingston DGI. History and chemistry. In: McGuire WP, Rowinsky EK, Eds. Paclitaxel in cancer treatment. New York: Marcel Dekker 1995; pp. 1-33.
287. Fang W.-S, Liang XT. Recent progress in structure activity relationship and mechanistic studies of taxol analogues. Mini-Rev Med Chem 2005; 5: 1-12.
288. Fu Y, Li S, Zu Y, et al. T. Medicinal chemistry of paclitaxel and its analogues. Curr Med Chem 2009; 16: 3966-85.
289. Wub M, Wua Y, Jing Zhou J, et al. Structural characterisation of a water-soluble polysaccharide with high branches from the leaves of Taxus chinensis var. mairei. Food Chem 2009; 113: 1020-4.
290. Nikolakakis A, Haidara K, Sauriol F, et al. Semi-Synthesis of an O-Glycosylated docetaxel analogue. Bioorganic Med Chem 2003; 11: 1551-6.
291. Takahashi T, Tsukamoto H, Yamada H. Design and synthesis of water-soluble taxol analogs: Taxol-sialyl conjugate. Bioorg Med Chem Lett 1998; 8: 113-6.
292. Wang K, Zou J, Chen R, et al. Highly regioselective glycosylation of xylosyl-containing taxanes by Enterobacter cloaceae. Fitoterapia 2013; 84: 158-62.
293. Hostettmann K. Marston A. Saponins. Cambridge: Cambridge University Press 1995.
294. Liu J. Oleanolic acid and ursolic acid: research perspectives. J Ethnopharmacol 2005; 100: 92-4.
295. Pollier J, Goossens A. Oleanolic acid. Phytochemistry 2012; 77: 10-5.
296. Grynkiewicz G, Jatczak K. Triterpene sapogenins with oleanene skeleton: chemotypes and biological activities. Acta Biochim Polon 2014; 61: 227-43.
297. Xu K, Chu F, Li G, et al. Oleanolic acid synthetic oligoglycosides: a review on recent progress in biological activities. Pharmazie 2014; 69: 483-95.
298. Hardegger E, Leeman HJ, Robinet FG. Steroid and triterpene glycosides III. Glucosides of esters of oleanolic acid and glycosidal binding in beet sugar saponins. Helv Chim Acta 1952; 35: 824-9.
299. Gauthier C. Legault J. Pichette A. Recent progress in the synthesis of naturally occurring triterpenoid saponins. Mini-Rev Org Chem 2009; 6: 321-44.
300. Sha Y, Yan M-C, Liu J. Facile synthesis of oleanolic acid monoglycosides and glycosides. Molecules 2008; 13: 1472-86.
301. Liu Q, Fan Z, Li D, et al. Facile synthesis of several oleanene-type triterpenoid saponins. J Carbohydr Chem. 2010; 29: 386-402.
302. Cheng M-S, Yan M-C, Liu Y, et al. Synthesis of-hederin and hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety. Carbohydr Res 2006; 341: 60-67.
303. Liu Y, Lu WX, Yan MC. Synthesis and tumor cytotoxicity of novel amide derivatives of-hederin. Molecules 2010; 15: 7871-83.
304. Liu QC, Guo TT, Guo SD, et al. Synthesis and evaluation of four hederagenin glycosides as-glucosidase inhibitor. Helv Chim Acta 2013; 90: 142
305. Yu B, Xie JM, Deng SJ. First synthesis of a bisdesmosidic triterpene saponin by a highly efficient procedure. J Am Chem Soc 1999; 121: 12196-7.
306. Chwalek M, Ple K. Voutquenne-Nazabadioko L. Synthesis and hemolytic activity of some hederagenin diglycosides. Chem Pharm Bull 2004; 52: 965-71.
307. Wang Y, Zhang Y, Zhu Z, et al. Exploration of the correlation between the structure, hemolytic activity, and cytotoxicity of steroid saponins. Bioorg Med Chem 2007; 15: 2528-32.
308. Zhou Y, Gracia-Prieto C, Carney DA, et al. OSW-1: a natural compound with potent anticancer activity and a novel mechanism of action. J Natl Cancer Inst 2005; 97: 1781-5.
309. Tang Y, Li N, Duan J, et al. Structure, bioactivity, and chemical synthesis of OSW-1 and other steroidal glycosides in the genus Ornithogalum. Chem Rev 2013; 113: 5480-514.
310. Kubo S, Mimaki Y, Terao M, et al. Acylated cholestane glycosides from the bulbs of Ornithogalum saudersiae. Phytochemistry 1992; 31: 3969-73.
311. Guo C, Fuchs PL. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1. Tetrahedron Lett 1998; 39: 1099-102.
312. Gryszkiewicz-Wojtkielewicz A, Jastrz bska I, Morzycki JW, et al. Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae-natural products with cytostatic activity. Curr Org Chem 2003; 7: 1257-77.
313. Deng S, Yu B, Lou Y, et al. First total synthesis of an exceptionally potentantitumor saponin, OSW-1. J Org Chem 1999; 64: 202-8.
314. Xue J, Liu P, Pan Y, et al. A total synthesis of OSW-1. J Org Chem 2008; 73: 157-61.
315. Shi B, Tang P, Hu X, et al. OSW saponins: facile synthesis toward a new type of structures with potent antitumor activities. J Org Chem 2005; 70: 10354-67.
316. Morzycki JW, Wojtkielewicz A. Synthesis of a highly potent antitumor saponin OSW-1 and its analogues. Phytochem Rev 2005; 4: 259-77.
317. Kensils CR, Patel U, Lennic M, et al. Separation and characterization of saponins with adjuvant activity from Quillaja saponaria Molina cortex. J Immunol 1991; 146: 431-7.
318. Ragupathi G, Gardner JR, Livingston PO, et al. Natural and synthetic saponin adjuvant QS-21 for vaccines against cancer. Expert Rev Vaccines 2011; 10: 463-70.
319. Kensil CR, Kammer R. QS-21: a water-soluble triterpene glycoside adjuvant. Exp Opin Invest Drugs 1998; 7: 1475-82.
320. Martin R, Briones R. Industrial uses and sustainable supply of Quillaja saponaria saponins. Econ Bot 1999; 53: 302-11.
321. Martin RS, Briones R. Quality control of commercial Quilaja (Quillaja saponaria Molina) extracts by reverse phase HPLC. J Sci Food Agric 2000; 80: 2063-8.
322. Galonić DP, Gin DY. Chemical glycosylation in the synthesis of glycoconjugate antitumor vaccines. Nature 2007; 446: 1000-06.
323. Zhu X, Yu B, Hui Y, et al. Synthesis of the trisaccharide and tetrasaccharide moieties of the potent immunoadjuvant QS-21. Eur J Org Chem 2004; 965-73.
324. Kim Y-J. Synthetic studies of complex immunostimulants from Quillaja saponaria: synthesis of the potent immunoadjuvant QS-21A. J Am Chem Soc 2006; 128: 11906-15.
325. Garcia BA, Gin DY. Dehydrative glycosylation with activated diphenyl sulphonium reagents. Scope, mode of C(1)-hemiacetal activation, and detection of reactive glycosyl intermediates. J Am Chem Soc 2000; 122: 4269-79.
326. Ishihara K, Yamamoto H. Arylboron compounds as acid catalysts in organic synthetic transformations. Eur J Org Chem 1999; 527-38.
327. Wang P, Dai Q, Thogaripally P, et al. Synthesis of QS-21 based immunoadjuvants. J Org Chem 2013; 78: 11525-34.
328. Fernandez-Tejada A, Chea EK, George C, et al. Design, synthesis, and immunologic evaluation of vaccine adjuvant conjugates based on QS-21 and tucaresol. Bioorg Med Chem 2014; 5917-23.
329. Zu L. Zhao Y Gu G. Recent development in the synthesis of natural saponins and their derivatives. J Carbohydr Chem 2014; 33: 299-307.
330. Fernandez-Tejada A, Chea EK, George C, et al. Development of a minimal saponin vaccine adjuvant based on QS-21. Nat Chem 2014; 635-643
331. Chea EK, Adams MM, Livingston P, et al. Synthesis and preclinical evaluation of QS-21 variants leading to simplified vaccine adjuvants and mechanistic probes. J Am Chem Soc 2012; 134: 13448-57.
332. Fahey, JW, Zalcmann AT, Talalay P. The chemical diversityand distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 2001; 56: 5-51.
333. Drewnowski A, Gomez-Carneros C. Bitter taste, phytonutrients, and the consumer: a review. Am J Clin Nutr 2000; 72: 1424-35.
334. Cinciripini P, Hecht M, Henningfield SS, et al. Tobacco addiction: implications for treatment and cancer prevention. J Natl Cancer Inst 1997; 89: 1852-67.
335. Keum Y S, Jeong WS, Kong AN. Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms. Mutat Res 2004; 555: 191-202.
336. Bianchini F, Vainio H. Isothiocyanates in cancer prevention. Drug Metab Rev 2004; 36: 655-67.
337. Verhoeven DT, Goldbohm RA, van Poppel, G, et al. Epidemiological studies on brassica vegetables and cancer risk. Cancer Epidemiol Biomarkers Prev 1996; 5: 733-48.
338. Higdon JV, Delage B, Williams DE, et al. Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis. Pharmacol Res 2007; 55: 224-36.
339. Talalay P, Fahey JW. Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J Nutr 2001; 131: 3027S-33S.
340. Johnson IT. Glucosinolates: bioavailability and importance to health. Int J Vitam Nutr Res 2002; 72: 26-31.
341. Abramski W, Chmielewski M. Practical synthesis of sinigrin. J Carbohydr Chem 1996; 15: 109-13.
342. Shiao TC, Roy R. “Active-latent” thioglycosyl donors and acceptors in oligosaccharide syntheses. Top Curr Chem 2011; 301: 69-108.
343. Fraser-Reid B, Lo pez J C. Armed-disarmed effects in carbohydrate chemistry: History, synthetic and mechanistic studies. Top Curr Chem 2011; 301: 1-29.
344. Wuts PGM, Greene TW. Greene’s Protective Groups in Organic Synthesis. 4th ed. New York: Wiley 2006.
345. Satoh, H.; Manabe, S. Design of chemical glycosyl donors: Does changing ring conformation influence selectivity/reactivity? Chem Soc Rev 2013; 42: 4297-309.
346. Bohe L, Crich D. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art. Carbohydr Res 2015; 403: 48-59
347. Frihed TG, Bols M, Pedersen CM. Mechanisms of glycosylation reactions studied by low-temperature nuclear magnetic resonance. Chem Rev 2015; 115: 4963-5013
348. Christensen HM, Oscarson S, Jensen HH. Common side reactions of the glycosyl donor in chemical glycosylation. Carbohydr Res 2015; 408: 51-95.
349. Schmidt RR, Kinzy W. Anomeric oxygen activation for glycoside synthesis. The trichloroacetimidate method. Adv Carbohydr Chem Biochem 1994; 50: 21-123.
350. Zhu X, Schmidt RR. New principles for glycoside-bond formation. Angew Chem Int Ed 2009; 48: 1900-34.
351. Grantt RW, Peltier-Pain P, Thorson JS. Enzymatic methods for glyco (diversification/randomization) of drugs and small molecules. Nat Prod Rep 2011; 28: 1811-53.
352. Shoda S. Glycosyl Synthesis from Anomeric Halides. In: Demchenko AV, Ed. Handbook of chemical glycosylation. Weinheim: Wiley-VCH 2008: pp. 29-93.
353. Shiao TC, Roy R. “Active-latent” thioglycosyl donors and acceptors in oligosaccharide syntheses. Top Curr Chem 2011; 301: 69-108.
354. McKay MJ. Nguyen HM. Recent advances in transition metalcatalysed glycosylation. ACS Catal 2012; 2: 1563-95.
355. Ferrier RJ, Hoberg JO. Synthesis and reaction of unsaturated sugars. Adv Carbohydr Chem Biochem 2003; 58: 55-119.
356. Jensen KJ. O-Glycosylations under neutral or basic conditions. J Chem Soc Perkin Trans I 2002; 2219-33.
357. McKay MJ, Nguyen HM. Recent advances in transition metalcatalysed glycosylation. ACS Catal 2012; 2: 1563-95.
358. Hanessian S, Lou B. Stereocontrolled glycosyl transfer reactions with unprotected glycosyl donors. Chem Rev 2000; 100: 4443-63.
359. Witczak ZJ, Bielski R, Eds. Click Chemistry in Glycoscience: New Development and Strategies. New York: John Wiley & Sons 2013.
360. Mangsang W. Sirion U. Saeeng R. One-pot synthesis of O-glycosyl triazoles by O-glycosylation-click reaction Carbohydr Res 2013 375: 79-89.
361. Aragao-Leoneti V, Campo VL., Gomes AS, et al. Application of copper(I)-catalysed azide/alkyne cycloaddition (CuAAC) “click chemistry” in carbohydrate drug and neoglycopolymer synthesis. Tetrahedron 2010; 66: 9475-92.
362. Friedrich S, Hahn F. Opportunities for enzyme catalysis in natural product chemistry. Tetrahedron 2015; 71: 1473-508.