Facile one-pot syntheses of new C-28 esters of oleanolic acid and studies on their antiproliferative effect on T cells
-
Muhammad S. Ali
, Ghafoor Ahmed
Abstract
Structure-activity relationship studies on oleanolic acid (1) have resulted in facile syntheses of its new C-28 esters 2–7 by way of one-pot reaction of 1 with a variety of alkylating agents. Oleanolic acid and its new esters were studied for their in vitro antiproliferative effect on healthy human peripheral blood mononuclear cell isolated phytohemagglutinin activated T cells. Results showed that compounds 1, 3, and 5 exhibited significant inhibitory activity on T-cell proliferation. Compound 5 was found to be the most potent, with an IC50 value of 4.249 μg/mL, among all tested compounds, and its activity could be attributed to the presence of bromine atom in the molecule.
References
1. Nazuruk J, Borzym-Kluczyk M. The role of triterpenes in the management of diabetes mellitus and its complications. Phytochem Rev 2015;14:675–90.10.1007/s11101-014-9369-xSearch in Google Scholar PubMed
2. Meng Y, Zhao Y, Kuai Z, Liu L, Li W. Synthesis and antitumor activity evaluation of novel oleanolic acid derivatives. J Asian Nat Prod Res 2017;19:1000–10.10.1080/10286020.2017.1283310Search in Google Scholar PubMed
3. Li F, Liu Y, Wang S, Wei G, Cheng M. Synthesis and tumor cytotoxicity of novel 1,2,3-triazole-substituted 3-oxo-oleanolic acid derivatives. Chem Res Chin Univ 2016;32:938–42.10.1007/s40242-016-6301-5Search in Google Scholar
4. Lin C, Wen X, Sun H. Oleanolic acid derivatives for pharmaceutical use: a patent review. Expert Opin Ther Patents 2016;26:643–55.10.1080/13543776.2016.1182988Search in Google Scholar
5. Cheng K, Su C, Huang J, Liu J, Zheng Y, Chen Z. Conjugation of uridine with oleanolic acid derivatives as potential antitumor agents. Chem Biol Drug Des 2016;88:329–40.10.1111/cbdd.12758Search in Google Scholar PubMed
6. Meng Y, Feng C, Zhang L, Zhang M, Zhao N. Synthesis and antitumor activity of oleanolic acid derivatives. Yaoxue Xuebao 2015;50:469–74.10.1080/10286020.2018.1464560Search in Google Scholar
7. Ali MS, Jahangir M, Hasan SS, Choudhary MI. Inhibition of α-glucosidase by oleanolic acid and its synthetic derivatives. Phytochemistry 2002;60:295–9.10.1016/S0031-9422(02)00104-8Search in Google Scholar PubMed
8. Chilson OP, Kelly-Chilson AE. Mitogenic lectins bind to the antigen receptor on human lymphocytes. Eur J Immunol 1989;19:389–96.10.1002/eji.1830190225Search in Google Scholar PubMed
9. Ulmer AJ, Flad HD. Functional relationship of human T lymphocytes, monocytes and interleukins. II. Helper requirements for phytohaemagglutinin-induced proliferation of human T-lymphocyte colony-forming cells. Scand J Immunol 1983;18:137–43.10.1111/j.1365-3083.1983.tb00850.xSearch in Google Scholar PubMed
10. Ceuppens JL, Baroja ML, Lorre K, Van Damme J, Billiau A. Human T cell activation with phytohemagglutinin. The function of IL-6 as an accessory signal. J Immunol 1988;141:3868–74.10.4049/jimmunol.141.11.3868Search in Google Scholar
11. Boyum A. Isolation of mononuclear cells and granulocytes from human blood. Scand J Clin Lab Invest 1968;21:77–89.Search in Google Scholar
12. Nielsen M, Gerwien J, Geisler C, Ropke C, Svejgaard A, Odum N. MHC class II ligation induces CD58 (LFA-3)-mediated adhesion in human T cells. Exp Clin Immunogenet 1998;15:61–8.10.1159/000019055Search in Google Scholar PubMed
©2018 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Research Articles
- Muscle relaxant activities of pistagremic acid isolated from Pistacia integerrima
- Facile one-pot syntheses of new C-28 esters of oleanolic acid and studies on their antiproliferative effect on T cells
- Biodiversity and full genome sequence of potato viruses Alfalfa mosaic virus and potato leaf roll virus in Egypt
- Carotenoids, tocopherols, organic acids, charbohydrate and mineral content in different medicinal plant extracts
- Two new usnic acid derivatives from the endophytic fungus Mycosphaerella sp.
- Antimicrobial activity and active compounds of a Rhus verniciflua Stokes extract
- Benzimidazole – Schiff bases and their complexes: synthesis, anticancer activity and molecular modeling as Aurora kinase inhibitor
Articles in the same Issue
- Frontmatter
- Research Articles
- Muscle relaxant activities of pistagremic acid isolated from Pistacia integerrima
- Facile one-pot syntheses of new C-28 esters of oleanolic acid and studies on their antiproliferative effect on T cells
- Biodiversity and full genome sequence of potato viruses Alfalfa mosaic virus and potato leaf roll virus in Egypt
- Carotenoids, tocopherols, organic acids, charbohydrate and mineral content in different medicinal plant extracts
- Two new usnic acid derivatives from the endophytic fungus Mycosphaerella sp.
- Antimicrobial activity and active compounds of a Rhus verniciflua Stokes extract
- Benzimidazole – Schiff bases and their complexes: synthesis, anticancer activity and molecular modeling as Aurora kinase inhibitor