(+)-(S)-Tylophorine

• CAT Number: R057170
• CAS Number: 482-20-2
• Molecular Formula: C24H27NO4
• Molecular Weight: 393.483
• Purity: ≥95%
• Storage: Store at +4C
• IUPAC Name: (13aS)-2,3,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
• InChI: InChI=1S/C24H27NO4/c1-26-21-9-16-15-8-14-6-5-7-25(14)13-20(15)19-12-24(29-4)23(28-3)11-18(19)17(16)10-22(21)27-2/h9-12,14H,5-8,13H2,1-4H3/t14-/m0/s1
• InChIKey: SSEUDFYBEOIWGF-AWEZNQCLSA-N
• SMILES: COC1=C(C=C2C(=C1)C3=C(CN4CCCC4C3)C5=CC(=C(C=C52)OC)OC)OC

Tylophorine is a natural product and a major alkaloid of Tylophora indica. Tylophorine is known to possess anti-inflammatory and antitumor activity. Tylophorine arrests carcinoma cells at G1 phase by downregulating cyclin A2 expression.

Reference

1:An enantioselective strategy for the total synthesis of (S)-tylophorine via catalytic asymmetric allylation and a one-pot DMAP-promoted isocyanate formation/Lewis acid catalyzed cyclization sequence. Su B, Zhang H, Deng M, Wang Q.Org Biomol Chem. 2014 Jun 14;12(22):3616-21. doi: 10.1039/c4ob00200h. Epub 2014 Apr 23. PMID: 24756131 2:Collective asymmetric synthesis of (-)-antofine, (-)-cryptopleurine, (-)-tylophorine, and (-)-tylocrebrine with tert-butanesulfinamide as a chiral auxiliary. Zheng Y, Liu Y, Wang Q.J Org Chem. 2014 Apr 18;79(8):3348-57. doi: 10.1021/jo500013e. Epub 2014 Mar 28. PMID: 24679059 3:Tylophorine, a phenanthraindolizidine alkaloid isolated from Tylophora indica exerts antiangiogenic and antitumor activity by targeting vascular endothelial growth factor receptor 2-mediated angiogenesis. Saraswati S, Kanaujia PK, Kumar S, Kumar R, Alhaider AA.Mol Cancer. 2013 Jul 29;12:82. doi: 10.1186/1476-4598-12-82. PMID: 23895055 Free PMC Article4:c-Jun-mediated anticancer mechanisms of tylophorine. Yang CW, Lee YZ, Hsu HY, Wu CM, Chang HY, Chao YS, Lee SJ.Carcinogenesis. 2013 Jun;34(6):1304-14. doi: 10.1093/carcin/bgt039. Epub 2013 Feb 5. PMID: 23385061 5:An enantioselective strategy for the synthesis of (S)-tylophorine via one-pot intramolecular Schmidt/Bischler-Napieralski/imine-reduction cascade sequence. Su B, Chen F, Wang Q.J Org Chem. 2013 Mar 15;78(6):2775-9. doi: 10.1021/jo302725q. Epub 2013 Feb 11. PMID: 23373672 6:Left, right, or both? On the configuration of the phenanthroindolizidine alkaloid tylophorine from Tylophora indica. Stoye A, Peez TE, Opatz T.J Nat Prod. 2013 Feb 22;76(2):275-8. doi: 10.1021/np300838w. Epub 2013 Jan 31. PMID: 23369033 7:Cryptopleurine analogs with modification of e ring exhibit different mechanism to rac-cryptopleurine and tylophorine. Wang Y, Wong HC, Gullen EA, Lam W, Yang X, Shi Q, Lee KH, Cheng YC.PLoS One. 2012;7(12):e51138. doi: 10.1371/journal.pone.0051138. Epub 2012 Dec 10. PMID: 23251437 Free PMC Article8:Synthesis and biological evaluation of tylophorine-derived dibenzoquinolines as orally active agents: exploration of the role of tylophorine e ring on biological activity. Lee YZ, Yang CW, Hsu HY, Qiu YQ, Yeh TK, Chang HY, Chao YS, Lee SJ.J Med Chem. 2012 Dec 13;55(23):10363-77. doi: 10.1021/jm300705j. Epub 2012 Dec 4. PMID: 23167614 9:A novel tylophorine analog W-8 up-regulates forkhead boxP3 expression and ameliorates murine colitis. Meng X, Zhang Y, Jia Z, Huo X, He X, Tian G, Wu M, Wang Z, Zhou X, Xiong S, Gao X, Wu Z, Han J, Zhao L, Wang P, Hong Z, Wang Q, Yin Z.J Leukoc Biol. 2013 Jan;93(1):83-93. doi: 10.1189/jlb.0812402. Epub 2012 Nov 9. PMID: 23142729 10:A novel tylophorine analog NK-007 ameliorates colitis through inhibition of innate immune response. Wen T, Li Y, Wu M, Chen X, Han L, Bao X, Wang Z, Wang K, Hu Y, Zhou X, Wu Z, Wang P, Hong Z, Zhao L, Wang Q, Yin Z.Int Immunopharmacol. 2012 Dec;14(4):487-94. doi: 10.1016/j.intimp.2012.08.008. Epub 2012 Aug 25. PMID: 22929538