Synthesis of a highly potent antitumor saponin OSW-1 and its analogues

Phytochemistry Reviews

Volumn 4, Issue 2-3, 2005, Pages 259-277

  Morzycki, Jacek W ^a   Wojtkielewicz, Agnieszka ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Antitumor activity; Cholestane glycosides; OSW 1; Saponins; Steroids

Indexed keywords

3 O TEREPHTALIC ACID; 3,4 DIMETHOXYBENZOYL; 4 METHOXYBENZOYL; 5 FLUOROURACYL; ANTINEOPLASTIC AGENT; CEPHALOSTATIN 1; CINNAMOYL; CISPLATIN; CYCLOPHOSPHAMIDE; NANOPARTICLE; OSW 1; PACLITAXEL; SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CONFERENCE PAPER; CYTOTOXICITY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GALTONIA CANDICANS; LUNG ALVEOLUS CELL; MEDICINAL PLANT; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TUMOR CELL;

GALTONIA CANDICANS; LILIACEAE; ORNITHOGALUM SAUNDERSIAE;

EID: 28644433853     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-005-1233-6     Document Type: Conference Paper

References (50)

1. A Alexakis J Berlan Y Besace 1986 Organocopper conjugate addition reaction in the presence of trimethylchlorosilane Tetrahedron Lett. 27 1047 1050
2. P Bovicelli P Lupattelli D Fracassi E Mincione 1994 Sapogenins and dimethyldioxirane: a new entry to cholestanes functionalized at the side chain Tetrahedron Lett. 35 935 938
3. JE Bryan 1989 Bulbs Timber Press Portland 298 Vol. 2
4. Y Buchvarov E Balabanova-Radonova I Radenkova S Vankov 1984 Isolation of ornithogalum cardiac glycosides and polysaccharides from species, growing in Bulgaria Farmatsiya 34 33 37
5. N Chaosuancharoen N Kongkathip B Kongkathip 2004 A novel synthetic approach from diosgenin to a 17α-hydroxy orthoester via a regio- and stereo-specific rearrangement of an epoxy ester Synth. Commun. 34 961 983
6. EJ Corey NW Boaz 1985 The reaction of combined organocuprate- chlorotrimethylsilane reagents with conjugated carbonyl compounds Tetrahedron Lett. 26 6019 6022
7. FA Davis AC Sheppard 1989 Applications of oxaziridines in organic synthesis Tetrahedron 45 5703 5742
8. L Deng H Wu B Yu M Jiang J Wu 2004 Synthesis of OSW-1 analogs with modified side chains and their antitumor activities Bioorg. Med. Chem. Lett. 14 2781 2785
9. S Deng B Yu Y Lou Y Hui 1999 First total synthesis of an exceptionally potent antitumor saponin, OSW-1 J. Org. Chem. 64 202 208
10. P Duhamel D Cahard JM Poirier 1993 Unprecedented route to enolates from silyl enol ethers and enol acetates: reaction with hard and soft electrophiles J. Chem. Soc., Perkin Trans. 1 21 2509 2511
11. U Ghannamy B Kopp W Robien W Kubelka 1987 Cardenolide aus Ornithogalum boucheanum Planta Med. 53 172 178
12. A Gryszkiewicz-Wojtkielewicz I Jastrzȩbska JW Morzycki DB Romanowska 2003 Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae - new natural products with cytostatic activity Curr. Org. Chem. 7 1257 1277
13. C Guo PL Fuchs 1998 The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1 Tetrahedron Lett. 39 1099 1102
14. C Guo TG LaCour PL Fuchs 1999 On the relationship of OSW-1 to the cephalostatins Bioorg. Med. Lett. 9 419 424
15. Ibuka T, Taga T, Shingu T, Nishii S & Yamamoto Y (1988a) A new stereoselective synthesis of (20R)- and (20S)-steroidal side chains. J. Chem. Soc., Chem. Commun.: 342-344.
16. T Ibuka T Taga T Shingu M Saito S Nishii Y Yamamoto 1988b New stereoselective synthesis of 20S and 20R steroidal side chains. Remarkable stereoselectivity differences between saturated and α,β-unsaturated steroidal esters J. Org. Chem. 53 3947 3952
17. W Kariuki S Kako FW Pierson CT Larsen A Zajac G Saunders RD Schwartz TS Cummings J Doerr FN Hegngi 1999 Growth and flowering of Ornithogalum saundersiaeBak Sci. Horticult. 81 57 70
18. S Kubo Y Mimaki M Terao Y Sashida T Nikaido T Ohmoto 1992 Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae Phytochemistry 31 3969 3973
19. M Kuroda Y Mimaki Y Sashida 1999 Cholestane rhamnosides from the bulbs of Ornithogalum saundersiae Phytochemistry 52 445 452
20. M Kuroda Y Mimaki Y Sashida T Yamori T Tsuruo 2000 Galtonioside A, a novel cytotoxic cholestane glycoside from Galtonia candicans Tetrahedron Lett. 41 251 255
21. M Kuroda Y Mimaki A Yokosuka Y Sashida 2001 Cholestane glycosides from the bulbs of Galtonia candicans and their cytotoxicity Chem. Pharm. Bull. 49 1042 1046
22. BH Lipshutz D Pollart J Monforte H Kotsuki 1985 Pd(II)-catalyzed acetal/ketal hydrolysis/exchange reaction Tetrahedron Lett. 26 705 708
23. X Ma B Yu Y Hui Z Miao J Ding 2001a Synthesis of steroidal glycosides bearing the disaccharide moiety of OSW-1 and their antitumor activities Carbohydr. Res. 334 159 164
24. X Ma B Yu Y Hui Z Miao J Ding 2001b Synthesis of OSW-1 analogues and a dimer and their antitumor activities Bioorg. Med. Chem. Lett. 11 2153 2156
25. X Ma B Yu Y Hui D Xiao J Ding 2000 Synthesis of glycosides bearing the disaccharide of OSW-1 or its 1→4-linked analogue and their antitumor activities Carbohydr. Res. 329 495 505
26. Matsuya Y, Itoh T & Nemoto H (2003) Total synthesis of A-nor B-aromatic OSW-1 aglycon: a highly effective approach to optically active trans-4,5-benzhydrindane. Eur. J. Org. Chem.: 2221-2224.
27. Y Mimaki M Kuroda A Kameyama Y Sashida T Hirano K Oka R Maekawa T Wada K Sugita JA Beutler 1997 Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs Bioorg. Med. Chem. Lett. 7 633 636
28. Y Mimaki M Kuroda Y Sashida T Yamori T Tsuruo 2000 Candicanoside A, a novel cytotoxic rearranged cholestane glycoside from Galtonia candicans Helv. Chim. Acta 83 2698 2704
29. JW Morzycki A Gryszkiewicz I Jastrzȩbska 2000 Some reactions of 16α,17α-oxido-steroids: a study related to the synthesis of the potent anti-tumor saponin OSW-1 aglycone Tetrahedron Lett. 41 3751 3754
30. JW Morzycki A Gryszkiewicz 2001a Synthesis of the potent antitumor saponin OSW-1 aglycone Polish J. Chem. 75 983 989
31. JW Morzycki A Gryszkiewicz I Jastrzȩbska 2001b Neighboring group participation in epoxide ring cleavage in reactions of some 16α,17α- oxidosteroids with lithium hydroperoxide Tetrahedron 57 2185 2193
32. JW Morzycki A Wojtkielewicz 2002 Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity Carbohydr. Res. 337 1269 1274
33. JW Morzycki A Wojtkielewicz S Wlołczyński 2004 Synthesis of analogues of a potent antitumor saponin OSW-1 Bioorg. Med. Chem. Lett. 14 3323 3326
34. RW Murray 1989 Dioxiranes Chem. Rev. 89 1187 1201
35. KC Nicolaou JI Trujillo K Chibale 1997 Design, synthesis and biological evaluation of carbohydrate-based mimetics of cRGDFV Tetrahedron 53 8751 8778
36. KC Nicolaou T Ohshima S Hosokawa FL van Delft D Vourloumis JY Xu J Pfefferkorn S Kimt 1998 Total synthesis of eleutherobin and eleuthosides A and B J. Am. Chem. Soc. 120 8674 8680
37. M Numazawa M Nagaoka Y Osawa 1982 Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism J Org Chem. 47 4024 4029
38. DM Piatak J Wicha 1978 Various approaches to the construction of aliphatic side chains of steroids and related compounds Chem. Rev. 78 199 241
39. L Reddy B Odhav KD Bhoola 2003 Natural products for cancer prevention: a global perspective Pharmacol. Therapeut. 99 1 13
40. JM Sargent CG Taylor 1989 Appraisal of the MTT assay as a rapid test of chemosensitivity in acute myeloid leukaemia Br. J. Cancer 60 206 210
41. RR Schmidt J Michel 1980 Facile synthesis of α- and β-O-glycosyl imidates; Preparation of glycosides and disaccharides Angew. Chem., Int. Ed. Engl. 19 731 732
42. RR Schmidt A Toepfer 1991 Glycosylation with highly reactive glycosyl donors: efficiency of the inverse procedure Tetrahedron Lett. 32 3353 3356
43. B Shi H Wu B Yu J Wu 2004 23-Oxa-analogues of OSW-1: efficient synthesis and extremely potent antitumor activity Angew. Chem. Int. Ed. 43 4324 4327
44. BB Snider B Shi 1999 Syntheses of (E)- and (Z)-volkendousin Tetrahedron 55 14823 14828
45. Q Xu X Peng W Tian 2003 A new strategy for synthesizing the steroids with side chains from steroidal sapogenins: synthesis of the aglycone of OSW-1 by using the intact skeleton of diosgenin Tetrahedron Lett. 44 9375 9377
46. JN Weinstein KW Kohn MR Grever VN Viswanadhan LV Rubinstein A Monks DA Scudiero L Welch A Koutsoukos KD Paull 1992 Neural computing in cancer drug development: predicting mechanism of action Science 258 447 451
47. J Wicha K Bal 1978 Synthesis of 21-hydroxycholesterol and 25-hydroxycholesterol from 3β -hydroxyandrost-5-en-17-one A method for the stereospecific construction of sterol side-chains J. Chem. Soc., Perkin Trans. I 1282 1288
48. W Yu Z Jin 2001 A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: total synthesis of highly potent antitumor natural product OSW-1 J. Am. Chem. Soc. 123 3369 3370
49. W Yu Z Jin 2001b A facile generation of enolates from silyl enol ethers by potassium ethoxide Tetrahedron Lett. 42 369 372
50. W Yu Z Jin 2002 Total synthesis of the anticancer natural product OSW-1 J. Am. Chem. Soc. 124 6576 6583