Isolation and Characterization of Yuremamine, a New Phytoindole

 

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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.

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
  PubMedGoogle Scholar
• 2 Gonçalves de Lima O. Archivos do Instituto de Pesquisas.  Agronomicas. 1946;  4 45
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 8 Parella T. In: Pulse program catalogue for Topspin v1.2. NMR Quide v 4.0 Barcelona; Bruker BioSpin GmbH 2004
  Google Scholar
• 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
  PubMedGoogle Scholar
• 10 Pretsch E, Bühlmann P, Affolter C. In: Structure Determination of Organic Compounds. Heidelberg; Springer Verlag 2000
  Google Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 13 Ott J. Ayahuasca analogues - Pangæan Entheogens. Kennewick, WA, USA; Natural Products 2004
  Google Scholar

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

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