Synthesis and antiproliferative activity of helonioside A, 3′,4′,6′-tri-O-feruloylsucrose, lapathoside C and their analogs

European Journal of Medicinal Chemistry

Volumn 58, Issue , 2012, Pages 418-430

  Panda, Parthasarathi ^a   Appalashetti, Manjuvani ^a   Natarajan, Meenubharathi ^b   Mary, Chan Park ^a   Venkatraman, Subbu S ^b   Judeh, Zaher M A ^a  

^a Nanyang Technological University   (Singapore)

^b NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

Antiproliferative activity; HeLa cells; Helonioside A, 3 ,4 ,6 tri O feruloylsucrose; Isopropylidene acetal; Lapathoside C; Phenylpropanoid sucrose esters; Regioselective acylation; Sucrose esters

Indexed keywords

3' MONO O ACETOXYFERULOYL 2,10:4,6 DI O ISOPROPYLIDENE SUCROSE; 3',4',6' TRI O ACETOXYFERULOYL 2,10:4,6 DI O ISOPROPYLIDENE SUCROSE; 3',4',6' TRI O ACETOXYFERULOYLSUCROSE; 3',4',6' TRI O FERULOYL 2,1':4,6 DI O ISOPROPYLIDENE SUCROSE; 3',4',6' TRI O FERULOYLSUCROSE; 3',6' DI O ACETOXYFERULOYLSUCROSE; 3',6' DI O FERULOYLSUCROSE; 3',6'DI O ACETOXYFERULOYL 2,1':4,6 DI O ISOPROPYLIDENE SUCROSE; 3,3',4',6' TETRA O ACETOXYFERULOYL 2,10:4,6 DI O ISOPROPYLIDENE SUCROSE; 3,3',4',6' TETRA O ACETOXYFERULOYLSUCROSE; 3,3',4',6' TETRA O FERULOYL SUCROSE; 3,6 DI O ACETOXYFERULOYL 3',6' DI O ACETOXYCINNAMOYLSUCROSE; 3,6 DI O FERULOYL 3',6' DI O COUMAROYLSUCROSE; 3,6,3',6' TETRA O COUMAROYLSUCROSE; 6 MONO O ACETOXYFERULOYL 3',6' DI O ACETOXYCINNAMOYLSUCROSE; 6 MONO O FERULOYL 3',6' DI O COUMAROYLSUCROSE; 6 MONO O FERULOYL 3,3',6' TRI O COUMAROYLSUCROSE; 6' MONO O ACETOXYFERULOYL 2,1':4,6 DI O ISOPROPYLIDENE SUCROSE; CAMPTOTHECIN; HELONIOSIDE A; LAPATHOSIDE C; PHENYLPROPANOID SUCROSE ESTER; SUCROSE ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CHEMOTHERAPY; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; IC 50; LIPOPHILICITY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CINNAMATES; COUMARIC ACIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HELA CELLS; HUMANS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SUCROSE;

EID: 84868709604     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.10.034     Document Type: Article

References (30)

1. P. Panda, M. Appalashetti, and Z.M.A. Judeh Phenylpropanoid sucrose esters: plant-derived natural products as potential leads for new therapeutics Curr. Med. Chem. 18 2011 3234 3251
2. K. Nakano, K. Murakami, Y. Takaishi, and T. Tomimatsu Feruloyl sucrose derivatives from Heloniopsis orientalis Chem. Pharm. Bull. 34 1986 5005 5010
3. T. Chen, J.-X. Li, and Q. Xu Phenylpropanoid glycosides from Smilax glabra Phytochemistry 53 2000 1051 1055
4. B. Shao, H. Guo, Y. Cui, M. Ye, J. Han, and D. Guo Steroidal saponins from Smilax china and their anti-inflammatory activities Phytochemistry 68 2007 623 630
5. M. Ono, C. Takamura, F. Sugita, C. Masuoka, H. Yoshimitsu, T. Ikeda, and T. Nohara Two new steroid glycosides and a new sesquiterpenoid glycoside from the underground parts of Trillium kamtschaticum Chem. Pharm. Bull. 55 2007 551 556
6. L. Yan, W.Y. Gao, Y.-J. Zhang, and Y. Wang A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis Fitoterapia 79 2008 306 307
7. L. Yan, W.Y. Gao, Y.-J. Zhang, and Y. Wang Corrigendum to A new phenylpropanoid glycosides from Paris polyphylla var. yunnanensis Fitoterapia 79 2008 306 307 Fitoterapia, 80 (2009) 143
8. L. Zhang, C.C. Liao, H.C. Huang, Y.C. Shen, L.M. Yang, and Y.H. Kuo Antioxidant phenylpropanoid glycosides from Smilax bracteata Phytochemistry 69 2008 1398 1404
9. L. Hongfang, M. Qingyun, L. Yuqing, Q. Jinfu, Z. Jun, and Z. Youxing Chemical constituents from Polygonum perfoliatum Chin. J. Appl. Environ. Biol. 5 2009 615 620
10. K.H. Kim, S.W. Chang, and K.R. Lee Feruloyl sucrose derivatives from Bistorta manshuriensis Can. J. Chem. 88 2010 519 523
11. J.J. Zhu, C.F. Zhang, M. Zhang, and Z.T. Wang Studies on chemical constituents in roots of Rumex dentatus Zhongguo Zhongyao Zazhi 31 2006 1691 1693
12. Y. Wang, W.Y. Gao, T.J. Zhang, and Y.Q. Guo A novel phenylpropanoid glycosides and a new derivation of phenolic glycoside from Paris Polyphylla var. yunnanensis Chin. Chem. Lett. 18 2007 548 550
13. H.Y. Min, H.J. Park, Y. Kim, E.J. Lee, H.J. Hwang, E.J. Park, and S.K. Lee Cytotoxic activities of Indigenous plant extracts in cultured human cancer cells Nat. Prod. Sci. 8 2002 170 172
14. Y.H. Kuo, Y.W. Hsu, C.C. Liaw, J.K. Lee, H.C. Huang, and L.M. Yang Kuo Cytotoxic phenylpropanoid glycosides from the stems of Smilax china J. Nat. Prod. 68 2005 1475 1478
15. J. Li, X. Bi, G. Zheng, Y. Hitoshi, T. Ikeda, and T. Nohara Steroidal glycosides and aromatic compounds from Smilax riparia Chem. Pharm. Bull. 54 2006 1451 1454
16. M. Takasaki, S. Kuroki, M. Kozuka, and T. Konoshima New phenylpropanoid esters of sucrose from Polygonum lapathifolium J. Nat. Prod. 64 2001 1305 1308
17. P. Fan, L. Terrier, A.-E. Hay, A. Marston, and K. Hostettmann Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F. Schmidt ex Maxim (Polygonaceae) Fitoterapia 81 2010 124 131
18. P. Fan, A.E. Hay, A. Marston, H. Lou, and K. Hostettmann Chemical variability of the invasive neophytes Polygonum cuspidatum Sieb. and Zucc. and Polygonum sachalinensis F. Schmidt ex Maxim Biochem. Syst. Ecol. 37 2009 24 34
19. L.L. Brown, S.R. Larson, A.T. Sneden, and C.-F. Vanicosides New phenylpropanoid glycosides from Polygonum pensylvanicum J. Nat. Prod. 61 1998 762 766
20. J.-M. Campagne Synthesis of Homologues of Phenylpropanoid Glycosides from Polygonum pensylvanicum 2001 Colleges of Humanities and Sciences, Virginia Commonwealth University Virginia p. 182
21. X. Sun, M.L. Zimmermann, J.M. Campagne, and A.T. Sneden New sucrose phenylpropanoid esters from Polygonum perfoliatum J. Nat. Prod. 63 2000 1094 1097
22. M.L. Zimmermann, and A.T. Sneden Vanicosides A and B, protein kinase C inhibitors from Polygonum pensylvanicum J. Nat. Prod. 57 1994 236 242
23. H.I. Duynstee, H. Ovaa, G.A. van der Marel, and J.H. van Boom Synthesis of niruriside a HIV REV/RRE binding inhibitor Recl. Trav. Chim. Pays-Bas 115 1996 339 340
24. P. Panda, M. Appalashetti, M. Natarajan, M.B. Chan-Park, S.S. Venkatraman, and Z.M.A. Judeh Synthesis and antitumor activity of lapathoside D and its analogs Eur. J. Med. Chem. 53 2012 1 12
25. A. Poschalko, T. Rohr, H. Gruber, A. Bianco, G. Guichard, J.-P. Briand, V. Weber, and D. Falkenhagen SUBPOL: a novel sucrose-based polymer support for solid-phase peptide synthesis and affinity chromatography applications J. Am. Chem. Soc. 125 2003 13415 13426
26. R.D. Hatfield, R.F. Helm, and J. Ralph Synthesis of methyl 5-O-trans-feruloyl-α-L-arabinofuranoside and its use as a substrate to assess feruloyl esterase activity Anal. Biochem. 194 1991 25 33
27. R.F. Helm, J. Ralph, and R.D. Hatfield Synthesis of feruloylated and p-coumaroylated methyl glycosides Carbohydr. Res. 229 1992 183 194
28. S. Jarosz, and M. Mach Regio- and stereoselective transformations of sucrose at the terminal positions Eur. J. Org. Chem. 2002 769 780
29. Y. Queneau, J. Fitremann, and S. Trombotto The chemistry of unprotected sucrose: the selectivity issue C. R. Chim. 7 2004 177 188
30. S. Saeed, N. Rashid, P.G. Jones, M. Ali, and R. Hussain Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents Eur. J. Med. Chem. 45 2010 1323 1331