Planta Med 2002; 68(6): 534-538
DOI: 10.1055/s-2002-32550
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Alkaloids, Amides and Antispasmodic Activity of Zanthoxylum hyemale

Neusa F. de Moura1 , Ademir F. Morel1 , Emilia C. Dessoy1 , Nilo Zanatta1 , Marilise M. Bürger2 , Neusa Ahlert2 , Gerusa P. Porto2 , Bernardo Baldisserotto2
  • 1Departamento de Quimica, Universidade Federal de Santa Maria, RS, Brazil
  • 2Departmento de Fisiologia, Universidade Federal de Santa Maria, RS, Brazil
Further Information

Publication History

July 19, 2001

December 9, 2001

Publication Date:
01 July 2002 (online)

Abstract

Two quinoline alkaloids, (-)-R-geilbalansine (1) and hyemaline (2), as well as aromatic amide, N-[2-(3,4-dimethoxyphenyl)-2-methoxyethyl)-2-methoxyethyl]benzamide (O-methylbalsamide) (3), were isolated as new natural products from the stem barks of Zanthoxylum hyemale, together with seven known compounds. Their structures were determined on the basis of spectroscopic data (IR, 1H- and 13C-NMR, MS). In addition, the antispasmodic activity of the crude extract of Z. hyemale and three other more abundant isolated compounds (4, 5 and 10) were studied in two different antispasmodic test models on isolated rat ileum and only the crude ethanolic extract presented antispasmodic activity.

References

  • 1 Waterman P G. New combination in Zanthoxylum L.  Taxon. 1973;  24 361-6
  • 2 Cruz G L. Dicionário de Plantas Úteis do Brasil. 1985: 597
  • 3 Barros G SG, Matos F JA, Vieira J EV, Souza M P, Medeiros M CJ. Pharmacological screening of some Brazilian plants.  Pharm Pharmac.. 1970;  22 116-8
  • 4 Moura N F, Ribeiro H B, Machado E CS, Ethur E M, Zanatta N, Morel A F. Benzophenanthridine alkaloids from Zanthoxylum rhoifolium .  Phytochemistry. 1997;  46 1443-6
  • 5 Moura N F, Giacomelli S R, Machado E CS, Morel A F, Silveira S FS, Bittencourt C F. Antibacterial activity of Zanthoxylum rhoifolium .  Fitoterapia. 1998;  69 271-8
  • 6 Ahond A, Poupat C, Pusset J. Plants from New-Caledonia: Geibalansine and O-acetylgeibalansine, new alkaloids isolated from Geijera balansae .  Phytochemistry. 1979;  18 1415-6
  • 7 Barr S A, Boyd D RJ. A general synthetic route to enantiopure quinoline alkaloids. Chem. Soc., Chem. Commun 1994: 153-4
  • 8 Konig W A, Ghercke B, Weseloh G. Determination of the absolute-configuration of secondary alcohols with Horeaus method including enantioselective gas chromatography.  Chirality. 1994;  6 141-7
  • 9 Burke B, Parkis H, Talbot A M. Oxazole and its precursor in Amyris balsamifera .  Heterocycles. 1979;  12 349-51
  • 10 Rosemund K W, Nothnagel M, Riesenfeldt H. Über Versuche in der Isochinolin Reihe und über eine Synthese des Papaverins.  Chem. Ber.. 1927;  60 392
  • 11 Albónico S M, Kuck A M, Deulofeu V J. Tembamida from Fagara hyemalis (St. Hill) Engler. J. Chem. Soc. (C) 1967: 1327-8
  • 12 Patra A, Mitra A K, Ghosh A, Mukhopadhyay P K. C-13 NMR-spectra of tembamida, aegeline and related amides.  Organic Magnetic Resonance. 1981;  16 65-7
  • 13 Krajniak E R, Ritchie E, Taylor W C. Chemical constituents of Australian Zanthoxylum species: Further examination of constituents of bark of Zanthoxylum conspersipunctatum (Rutaceae).  Aust. J. Chem.. 1973;  26 687-9
  • 14 Boyd D R, Sharma N D, Barr S A, Carroll J G, Mackerracher D, Malone J F. Synthesis and absolute stereochemistry assignment of anantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids. J. Chem. Soc., Perkin Trans I 2000: 3397-405
  • 15 Ohmoto T. Triterpene methyl ethers from Gramineae plants: Lupeol methyl ether, 12-oxoanrundoin, and arborinol methyl ether. J. Chem. Soc., Chem. Comm. 1969: 601
  • 16 Mondon A, Scharzmaier U. Untersuchung von Cneorum tricoccum .  Chem. Ber.. 1975;  108 925-33
  • 17 Tanira M OM, Ali B H, Bashir A K, Wasfi I A, Chandranath I. Evaluation of the relaxant activity of some United Arab Emirates plants on intestinal smooth muscle.  J. Pharm. Pharmacol.. 1996;  48 545-50
  • 18 Sánches de Rojas V R, Ortega T, Villar A. Inhibitory effects of Cistus populifolius on contractile responses in the isolated rat duodenum.  Journal of Ethnopharmacology. 1995;  46 59-62
  • 19 Rastrelli L, Capasso A, Pizza C, De Tommasi N. New protopine and benzyltetrahydroprotoberberine alkaloids from Aristolochia constricta and their activity on isolated guinea-pig ileum.  J. Nat. Prod.. 1997;  60 1065-9
  • 20 Rojas A, Bah M, Rojas J I, Gutierrez D M. Smooth muscle relaxing activity of gentiopicroside isolated from Gentiana spathacea .  Planta Medica. 2000;  66 765-7

Prof. Dr. Ademir Farias Morel

Universidade Federal de Santa Maria

Departamento de Quimica

Camobi

Santa Maria

RS

Brazil

CEP: 97105-900

Email: afmorel@base.ufsm.br