Planta Medica, Table of Contents Planta Med 2005; 71(11): 1053-1057DOI: 10.1055/s-2005-873131 Original PaperNatural Product Chemistry© Georg Thieme Verlag KG Stuttgart · New YorkIsolation and Characterization of Yuremamine, a New PhytoindoleJouko J. Vepsäläinen1 , Seppo Auriola2 , Mikko Tukiainen2 , Nina Ropponen2 , J. C. Callaway2 1Department of Chemistry, University of Kuopio, Kuopio, Finland 2Department of Pharmaceutical Chemistry, University of Kuopio, Kuopio, Finland Recommend Article Abstract Buy Article Abstract Yuremamine was isolated and characterized from the stem bark of Mimosa tenuiflora. This plant is still used by indigenous peoples in North-eastern Brazil to make yurema, a psychoactive beverage that is used for medico-religious purpose (jurema preta or vinho da jurema, in Portuguese). The characterization of this novel compound by NMR and mass spectrometry introduces a new class of phytoindoles. Key words Phytochemistry - ethnopharmacology - tepescohuit - Mimosa hostilis - DMT - MAO Full Text References References 1 Paulino de Albuquerque U. The use of medicinal plants by the cultural descendents of African people in Brazil. Acta Farm Bonaerense. 2001; 20 139-44 2 Gonçalves de Lima O. Archivos do Instituto de Pesquisas. Agronomicas. 1946; 4 45 3 Lozoya X, Navarro V, Arnason J T, Kourany E. Experimental evaluation of Mimosa tenuiflora (Willd.) Poir. (Tepescohuite) I. Screening of the antimicrobial properties of bark extracts. Arch Invest Med (Méx). 1989; 20 87-93 4 Meckes-Lozoya M, Lozoya X, Gonzales J L, Martinez M. Effect produced by the alkaloid fraction of Mimosa tenuiflora (tepescohuite) on the peristaltic reflex of the guinea pig ileum. Arch Invest Med (Méx). 1990; 21 171-4 5 Pachter I L, Zacharias D E, Ribeiro O. Indole alkaloids of Acer saccharinum (the silver maple), Dictyoloma incanescens, Piptadenia colubrine, and Mimosa hostilis . J Org Chem. 1959; 24 1285-7 6 Meckes-Lozoya M, Lozoya X, Marles R J, Souchy-Breau C, Varasen A, Arnason J T. N,N-Dimethyltryptamine alkaloid in Mimosa tenuiflora bark (tepescohuite). Arch Invest Med (Méx). 1990; 21 175-7 7 Jiang Y, Massiot G, Lavaud C, Teulon J -M, Guéchot C, Haag-Berrurier M. et al . Triterpenoid glycosides from the bark of Mimosa tenuiflora . Phytochemistry. 1991; 30 2357-60 8 Parella T. In: Pulse program catalogue for Topspin v1.2. NMR Quide v 4.0 Barcelona; Bruker BioSpin GmbH 2004 9 Laatikainen R, Niemitz M, Weber U, Sundelin J, Hassinen T, Vepsäläinen J. General strategies for total-lineshape-type spectral analysis of NMR spectra using integral-transform iterator (NMR). J Magn Reson A. 1996; 120 1-10 10 Pretsch E, Bühlmann P, Affolter C. In: Structure Determination of Organic Compounds. Heidelberg; Springer Verlag 2000 11 Padwa A, Fryxell G E, Gasdaska J R, Venkatramanan M K, Wong G SK. A dipolar cycloaddition approach to pyrrolo[1,2-a]indoles using N-[(trimethylsily1)methyl]-substituted indoles. J Org Chem. 1989; 54 644-53 12 Callaway J C, McKenna D J, Grob C S, Brito G S, Raymon L P. et al . Pharmacokinetics of Hoasca alkaloids in healthy humans. J Ethnopharmacol. 1999; 65 243-56 13 Ott J. Ayahuasca analogues - Pangæan Entheogens. Kennewick, WA, USA; Natural Products 2004 J. C. Callaway, Ph. D. Department of Pharmaceutical Chemistry University of Kuopio PL 1627 FIN-70211 Kuopio Finland Phone: +358-40-725-2534 Fax: +358-17-162-456 Email: callaway@uku.fi Supplementary Material Supplementary Material www.thieme-connect.de/ejournals/toc/plantamedica
