Design, synthesis, and anti-tobacco mosaic virus (TMV) activity of glycoconjugates of phenanthroindolizidines alkaloids

Molecular Diversity

Volumn 18, Issue 1, 2014, Pages 25-37

  Wu, Meng ^a   Han, Guifang ^a   Meng, Chuisong ^a   Wang, Ziwen ^a   Liu, Yuxiu ^a   Wang, Qingmin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Aglycone; Glycoconjugates; Glyconconjugation; Phenanthroindolizidine alkaloids; Sugar

Indexed keywords

ALKALOIDS; ANTIVIRAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; DRUG DESIGN; GLYCOCONJUGATES; INDOLIZINES; PHENANTHROLINES; STRUCTURE-ACTIVITY RELATIONSHIP; TOBACCO MOSAIC VIRUS;

EID: 84894053007     PISSN: 13811991     EISSN: 1573501X     Source Type: Journal    
DOI: 10.1007/s11030-013-9484-4     Document Type: Article

References (39)

1. Bos L (2000) 100 years of virology: from vitalism via molecular biology to genetic engineering. Trends Microbiol 8:82-87. doi: 10.1016/S0966-842X(99) 01678-9
2. Hari V, Das P (1998) Ultra microscopic detection of plant viruses and their gene products. In: Hadidi A, Khetarpal RK, Koganezawa H (eds) Plant disease virus control. APS Press, St. Paul, pp 417-427
3. Chen MH, Chen Z, Song BA, Bhadury PS, Yang S, Cai XJ, Hu DY, Xue W, Zeng S (2009) Synthesis and antiviral activities of chiral thiourea derivatives containing an R-aminophosphonate moiety. J Agric Food Chem 57:1383-1388. doi: 10.1021/jf803215
4. Lerch B (1987) On the inhibition of plant virus multiplication by ribavirin. Antiviral Res 7:257-270. doi: 10.1016/0166-3542(87)90010-6
5. Schuster G, Höringklee W, Winter H, Esser G, Steinke U, Kochman W, Kramer W, Steinke W (1979) Antiphytoviral activity of 2,4 dioxo hexahydro triazine. Acta Virol 23:412-420
6. Qian XH, Lee PW, Cao S (2010) China: forward to the green pesticides via a basic research program. J Agric Food Chem 58: 2613-2623. doi: 10.1021/jf904098w
7. Seiber JN (2011) Sustainability and agricultural and food chemistry. J Agric Food Chem 59:1-21. doi: 10.1021/jf1046078
8. Gellert E (1982) The indolizidine alkaloids. J Nat Prod 45:50-73. doi: 10.1021/np50019a005
9. An TY, Huang RQ, Yang Z, Zhang DK, Li GR, Yao YC, Gao J (2001) Alkaloids from Cyanachum komarovii with inhibitory activity against the tobacco mosaic virus. Phytochemistry 58: 1267-1269. doi: 10.1016/S0031-9422(01)00382-X
10. Wang KL, Su B, Wang ZW, Wu M, Li Z, Hu YN, Fan ZJ, Mi N, Wang QM (2010) Synthesis and antiviral activities of phenanthroindolizidine alkaloids and their derivatives. J Agric Food Chem 58:2703-2709. doi: 10.1021/jf902543r
11. Wang ZW, Wang L, Ma S, Liu YX, Wang LZ, Wang QM (2012) Design, synthesis, antiviral activity, and SARs of 14-aminophenanthroindolizidines. J Agric Food Chem 60:5825-5831. doi: 10.1021/jf3013376
12. Wang ZW, Wei P, Wang LZ, Wang QM (2012) Design, synthesis, and anti-tobacco mosaic virus (TMV) activity of phenanthroindolizidines and their analogues. J Agric Food Chem 60: 10212-10219. doi: 10.1021/jf303550a
13. Chemler SR (2009) Phenanthroindolizidines and phenanthroquinolizidines: promising alkaloids for anti-cancer therapy. Curr Bioact Compd 5:2-19. doi: 10.2174/157340709787580928
14. Suffness M, Douros J (1980) Anticancer agents based on natural product models. Academic Press, New York
15. Nikolakakis A, Haidara K, Sauriol F, Mamer O, Zamir LO (2003) Semi-synthesis of an O-glycosylated docetaxel analogue. Biorg Med Chem 11:1551-1556. doi: 10.1016/S0968-0896(02)00607-7
16. Lerchen HG, von dem Bruch K (2000) Synthesis of 20- O O -linked 20(S) S) -camptothecin glycoconjugates: impact of the side chain of the ester-linked amino acid on epimerization during the acylation reaction and on hydrolytic stability of the final glycoconjugates. J Prakt Chem 342:753-760. doi: 10.1002/1521-3897(200010)342:8<753::AID-PRAC753>3.0.CO;2-3
17. Ahmed A, Peters NR, Megan K, Watson J, Hoffmann FM, Thorson JS (2006) Colchicine glycorandomization influences cytotoxicity and mechanism of action. J Am Chem Soc 128:14224-14225. doi: 10.1021/ja064686s
18. Bowles D, Lim EK, Poppenberger B, Vaistij FE (2006) Glycosyltransferases of lipophilic small molecules. Annu Rev Plant Biol 57:567-597. doi: 10.1146/annurev.arplant.57.032905.105429
19. Ross J, Li Y, Lim E, Bowles DJ (2001) Higher plant glycosyltransferases. Genome Biol 2:3004.1-3004.6. doi: 10.1186/gb-2001-2-2-reviews3004
20. Newman DJ, Cragg GM (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461-477
21. Clardy J, Walsh C (2004) Lessons from natural molecules. Nature 432:829-837. doi: 10.1038/nature03194
22. Thorson JS, Hosted TJ, Jiang J, Biggins JB, Ahlert J (2001) Nature's carbohydrate chemistry: the enzymatic glycosylation of bioactive bacterial metabolites. Curr Org Chem 5:139-167. doi: 10.2174/1385272013375706
23. Weymouth-Wilson AC (1997) The role of carbohydrates in biologically active natural products. Nat Prod Rep 14:99-110. doi: 10.1039/np9971400099
24. Xi Z, Zhang RY, Yu ZH, Ouyang D (2006) The interaction between tylophorine B and TMV RNA. Bioorg Med Chem Lett 16: 4300-4304. doi: 10.1016/j.bmcl.2006.05.059
25. Gao S, Zhang RY, Yu ZH, Xi Z (2012) Antofine analogues can inhibit tobacco mosaic virus assembly through small-molecule-RNA interactions. ChemBioChem 13:1622-1627. doi: 10.1002/cbic.201200313
26. Christopher J, Thibodeaux Liu HW (2007) Manipulating nature's sugar biosynthetic machineries for glycodiversification of macrolides: recent advances and future prospects. Pure Appl Chem 79:785-799. doi: 10.1351/pac200779040785
27. Toshim K, Tatsuta K (1993) Recent progress in O O -glycosylation methods and its application to natural products synthesis. Chem Rev 93:1503-1531. doi: 10.1021/cr00020a006
28. Jung KH, Muller M, Schmidt RR (2000) Intramolecular O O -glycoside bond formation. Chem Rev 100:4423-4442. doi: 10.1021/cr990307k
29. Schmidt RR, Kinzy W (1994) Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Adv Carbohydr Chem Biochem 50:21-123. doi: 10.1016/S0065-2318(08)60150-X
30. Sudibya HG, Ma JM, Dong XC, Ng S, Li LJ, Liu XW, Chen P (2009) Interfacing glycosylated carbon nanotube network devices with living cells to detect dynamic secretion of biomolecules. Angew Chem Int Ed 48:2723-2726. doi: 10.1002/anie.200805514
31. Cheng H, Gao XH, Xian M, Fang LY, Cai TB, Ji JJB, Tunac J, Sun D, Wang PG (2005) Synthesis and enzyme-specific activation of carbohydrate-geldanamycin conjugates with potent anticancer activity. J Med Chem 48:645-652. doi: 10.1021/jm049693a
32. Tornoe CW, Christensen C, Meldal M (2002) Peptidotriazoles on solid phase:[1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 67:3057-3064. doi: 10.1021/jo011148j
33. Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective ligation of azides and terminal alkynes. Angew Chem Int Ed 41:2596-2599. doi: 10.1002/1521- 3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
34. Dedola S, Nepogodiev SA, Field RA (2007) Recent applications of the CuI-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry. Org Biomol Chem 5: 1006-1017. doi: 10.1039/B618048P
35. Dondoni A (2007) Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction. Chem Asian J 2: 700-708. doi: 10.1002/asia.200700015
36. Jarrahpour AA, Shekarriz M, Taslimi A (2004) Synthesis and antimicrobial activity of some new sugar-based monocyclic \beta β -lactams. Molecules 9:29-38. doi: 10.3390/90100029
37. Moyle PM, Olive C, Ho MF, Pandey M, Dyer J, Suhrbier A, Fujita Y, Toth I (2007) Toward the development of prophylactic and therapeutic human papillomavirus type-16 lipopeptide vaccines. J Med Chem 50:4721-4727. doi: 10.1021/jm070287b
38. Lopez O, Maza S, Maya I, Fuentes J, Fernandez-Bolanos JG (2005) New synthetic approaches to sugar ureas. Access to ureido- \beta β -cyclodextrins. Tetrahedron 61:9058-9069. doi: 10.1016/j.tet.2005.07.041
39. Ávalos M, Babiano R, Cintas P, Hursthouse MB, Jiménez JL, Light ME, Palacios JC, Pérez EMS (2006) Synthesis of sugar isocyanates and their spplication to the gormation of ureido-linked disaccharides. Eur J Org Chem 657-671: doi: 10.1002/ejoc.200500601