Isomitraphylline

• CAT Number: I029576
• CAS Number: 4963-01-3
• Molecular Formula: C21H24N2O4
• Molecular Weight: 368.43
• Purity: 98%
• Synonyms: Isomitraphylline; Ajmalicine oxindole A
• Target: Disease Research Fields
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (7alpha,19alpha)-
• InChI: InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21-/m0/s1
• InChIKey: JMIAZDVHNCCPDM-NWQITLLVSA-N
• SMILES: COC(C1=CO[C@H]([C@H]2CN3CC[C@@]4(C(Nc5c4cccc5)=O)[C@@H]3C[C@H]12)C)=O

Isomitraphylline is a biochemical.

Reference

1: Alvarenga-Venutolo S, Rosales-López C, Sánchez-Chinchilla L, Muñoz-Arrieta R, Aguilar-Cascante F. Seasonality effect on the composition of oxindole alkaloids from distinct organs of Uncaria tomentosa from the Caribbean region of Costa Rica. Phytochemistry. 2018 Jul;151:26-31. doi: 10.1016/j.phytochem.2018.03.008. Epub 2018 Apr 6. PubMed PMID: 29631104.
2: Azevedo BC, Morel LJF, Carmona F, Cunha TM, Contini SHT, Delprete PG, Ramalho FS, Crevelin E, Bertoni BW, França SC, Borges MC, Pereira AMS. Aqueous extracts from Uncaria tomentosa (Willd. ex Schult.) DC. reduce bronchial hyperresponsiveness and inflammation in a murine model of asthma. J Ethnopharmacol. 2018 May 23;218:76-89. doi: 10.1016/j.jep.2018.02.013. Epub 2018 Feb 10. PubMed PMID: 29432856.
3: Honório ICG, Bertoni BW, Telles MPC, Braga RDS, França SC, Coppede JDS, Correa VSC, Diniz Filho JAF, Pereira AMS. Genetic and chemical diversity of Uncaria tomentosa (Willd. ex. Schult.) DC. in the Brazilian Amazon. PLoS One. 2017 May 5;12(5):e0177103. doi: 10.1371/journal.pone.0177103. eCollection 2017. PubMed PMID: 28475604; PubMed Central PMCID: PMC5419575.
4: Chang CW, Yeh YY, Chang LC, Hsu MC, Wu YT. Rapid determination of oxindole alkaloids in cat’s claw by HPLC using ionic liquid-based microwave-assisted extraction and silica monolithic column. Biomed Chromatogr. 2017 Aug;31(8). doi: 10.1002/bmc.3925. Epub 2017 Jan 24. PubMed PMID: 28009448.
5: Kaiser S, Carvalho ÂR, Pittol V, Dietrich F, Manica F, Machado MM, de Oliveira LF, Oliveira Battastini AM, Ortega GG. Genotoxicity and cytotoxicity of oxindole alkaloids from Uncaria tomentosa (cat’s claw): Chemotype relevance. J Ethnopharmacol. 2016 Aug 2;189:90-8. doi: 10.1016/j.jep.2016.05.026. Epub 2016 May 13. PubMed PMID: 27180878.
6: Sánchez-Rojo S, Cerda-García-Rojas CM, Esparza-García F, Plasencia J, Poggi-Varaldo HM, Ponce-Noyola T, Ramos-Valdivia AC. Long-term response on growth, antioxidant enzymes, and secondary metabolites in salicylic acid pre-treated Uncaria tomentosa microplants. Biotechnol Lett. 2015 Dec;37(12):2489-96. doi: 10.1007/s10529-015-1931-0. Epub 2015 Aug 14. PubMed PMID: 26272395.
7: Zhang Q, Zhao JJ, Xu J, Feng F, Qu W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol. 2015 Sep 15;173:48-80. doi: 10.1016/j.jep.2015.06.011. Epub 2015 Jun 17. Review. PubMed PMID: 26091967.
8: Luna-Palencia GR, Huerta-Heredia AA, Cerda-García-Rojas CM, Ramos-Valdivia AC. Differential alkaloid profile in Uncaria tomentosa micropropagated plantlets and root cultures. Biotechnol Lett. 2013 May;35(5):791-7. doi: 10.1007/s10529-012-1128-8. Epub 2013 Jan 8. PubMed PMID: 23296316.
9: Shukla A, Srinivasan BP. 16,17-Dihydro-17b-hydroxy isomitraphylline alkaloid as an inhibitor of DPP-IV, and its effect on incretin hormone and β-cell proliferation in diabetic rat. Eur J Pharm Sci. 2012 Sep 29;47(2):512-9. doi: 10.1016/j.ejps.2012.07.012. Epub 2012 Jul 20. PubMed PMID: 22820565.
10: León F, Habib E, Adkins JE, Furr EB, McCurdy CR, Cutler SJ. Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A. Nat Prod Commun. 2009 Jul;4(7):907-10. PubMed PMID: 19731590.
11: García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing’s sarcoma and breast cancer cell lines. Planta Med. 2010 Feb;76(2):133-6. doi: 10.1055/s-0029-1186048. Epub 2009 Sep 1. PubMed PMID: 19724995.
12: Xin WB, Gu P, Chou GX, Wang ZT. [Studies on alkalodial constituents in leaves of Uncaria hirsuta]. Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2124-8. Chinese. PubMed PMID: 19066056.
13: Paradowska K, Wolniak M, Pisklak M, Gliński JA, Davey MH, Wawer I. (13)C, (15)N CPMAS NMR and GIAO DFT calculations of stereoisomeric oxindole alkaloids from Cat’s Claw (Uncaria tomentosa). Solid State Nucl Magn Reson. 2008 Nov;34(4):202-9. doi: 10.1016/j.ssnmr.2008.10.002. Epub 2008 Oct 22. PubMed PMID: 19019638.
14: Pilarski R, Poczekaj-Kostrzewska M, Ciesiołka D, Szyfter K, Gulewicz K. Antiproliferative activity of various Uncaria tomentosa preparations on HL-60 promyelocytic leukemia cells. Pharmacol Rep. 2007 Sep-Oct;59(5):565-72. PubMed PMID: 18048957.
15: Pandey R, Singh SC, Gupta MM. Heteroyohimbinoid type oxindole alkaloids from Mitragyna parvifolia. Phytochemistry. 2006 Oct;67(19):2164-9. Epub 2006 Jul 26. PubMed PMID: 16872649.
16: Bacher N, Tiefenthaler M, Sturm S, Stuppner H, Ausserlechner MJ, Kofler R, Konwalinka G. Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells. Br J Haematol. 2006 Mar;132(5):615-22. PubMed PMID: 16445836.