Synthesis of a tetra- and a trisaccharide related to an anti-tumor saponin "Julibroside J28" from Albizia julibrissin.
Simple and convergent synthesis of a tetra- and a trisaccharide portions of an antitumor compound Julibroside J(28), isolated from Albizia julibrissin, that showed significant in vitro antitumor activity against HeLa, Bel-7402 and PC-3M-1E8 cancer cell lines is reported. The tetrasaccharide has been synthesized as its p-methoxyphenyl glycoside starting from commercially available D-glucose, L-rhamnose and L-arabinose. The trisaccharide part has been synthesized from commercially available N-acetyl D-glucosamine, D-fucose and D-xylose using simple protecting group manipulations. Sulfuric acid immobilized on silica has been used successfully as a Brönsted acid catalyst for the crucial glycosylation steps.
Roy
Bimalendu
B
Medicinal and Process Chemistry Division, Central Drug Research Institute, Chattar Manzil Palace, Lucknow, 226 001 Uttar Pradesh, India.
Pramanik
Kausikisankar
K
Mukhopadhyay
Balaram
B
D031289:Albizzia / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology; D002240:Carbohydrate Sequence; D006367:HeLa Cells; D006801:Humans; D008969:Molecular Sequence Data; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology
D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; D014312:Trisaccharides; D014315:Triterpenes; C505995:julibroside J28
J Org Chem. 2004 Sep 17;69(19):6249-56
15357583
J Org Chem. 2000 May 19;65(10):3064-73
10814198
Angew Chem Int Ed Engl. 2005 Oct 7;44(39):6315-8
16172990
J Org Chem. 2002 Feb 8;67(3):892-903
11856034
Crit Rev Food Sci Nutr. 1987;26(1):27-135
3308321
Carbohydr Res. 1993 Jul 5;245(1):81-96
8358751
Proc Natl Acad Sci U S A. 1999 Oct 26;96(22):12923-8
10536024
J Org Chem. 2004 Oct 29;69(22):7758-60
15498011
Carbohydr Res. 1993 Jul 5;245(1):65-80
8358750
Bioorg Med Chem Lett. 2005 Oct 15;15(20):4493-5
16112860
Bioorg Med Chem. 2006 Mar 1;14(5):1518-37
16275104
Carbohydr Res. 1988 Jan 15;172(1):27-35
3349501
Adv Biochem Eng Biotechnol. 2002;75:31-49
11783842