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Planta Med 2002; 68(7): 631-634
DOI: 10.1055/s-2002-32898
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Quinoline Alkaloids, Coumarins and Volatile Constituents of Helietta longifoliata

Neusa F. de Moura1 , Euclésio Simionatto1 , Carla Porto1 , Solange C. S. Hoelzel1 , Emilia C. S. Dessoy1 , Nilo Zanatta1 , Ademir F. Morel1
  • 1Departamento de Química, Universidade Federal de Santa Maria, RS, Brazil
Further Information

Publication History

Received: October 11, 2001

Accepted: February 3, 2002

Publication Date:
22 July 2002 (online)

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Abstract

A new quinoline alkaloid named helietidine (1), and seven known compounds (2 - 8) have been isolated from the stem barks of Helietta longifoliata. The structures of the new and the known compounds were established on the basis of spectral evidence, especially by 2D NMR (1H-1H COSY, NOESY, HMQC, HMBC). In addition, the volatile constituents of H. longifoliata leaves were analysed by gas chromatography-mass spectrometry (GC-MS). Twenty-five constituents were identified representing ca. of 96 % of the oil, and limonene (17.50 %), germacrene D (16.60 %), elemol (11.81 %), bicyclogermacrene (11.67 %), guaiol (11.53), and epi-α-bisabolol (7.24 %) were the most abundant components. The oil was bioactive against some Gram-positive and Gram-negative bacteria, as revealed by bioautography.

Key words

Helietta longifoliata - Rutaceae - alkaloids - coumarins - essential oil - antibacterial activity

References

  • 1 Cruz G L. Dicionário de Plantas Úteis do Brasil, 597. 3a edição. Editora Civilização Brasileira S.A Rio de Janeiro; 1985
    Google Scholar
  • 2 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
    CrossrefPubMedGoogle Scholar
  • 3 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;  LXIX 271-2
    PubMedGoogle Scholar
  • 4 Collins J F, Gray G A, Grudon M F, Harrison D M, Spyropou C G. Convenient synthesis of furoquinoline alkaloids of dictamine type.  Journal of Chemical Society Perkin Trans.. 1973;  1 94-7
    PubMedGoogle Scholar
  • 5 Rios M Y, Delgado G. Terpenoids and alkaloids from Esenbeckia belizencis. Spontaneous oxidation of furanoquinoline alkalois.  Journal of Natural Products. 1992;  55 1307-9
    CrossrefPubMedGoogle Scholar
  • 6 Brown R FC, Gilham P T, Hughes G K, Ritchie E. The chemical constituents Australian flindersia species: The constituentes of Flindersia maculosa Lindl.  Australian Journal Chemistry. 1954;  7 81-8
    PubMedGoogle Scholar
  • 7 Steck W, Bailey B K, Shyluk J K, Gamborg O L. Coumarins and alkaloids from cell cultures of Ruta gravolens .  Phytochemistry. 1971;  10 191-4
    CrossrefPubMedGoogle Scholar
  • 8 Pozzi H, Sánchez E, Comin J. Studies on Argentine Plants XXII - Heliettin, a new furocoumarin from Helietta longifoliata Britt.  Tetrahedron. 1967;  23 1129-37
    CrossrefPubMedGoogle Scholar
  • 9 Brooker R M, Eble J N, Starkovs N A. Chalepensin, chalepin and chalepin acetato, three novel furocoumarins from Ruta chalepensis .  Lloydia. 1967;  30 73-7
    PubMedGoogle Scholar
  • 10 Kumar V, Vallipuram K, Adebajo A C, Reisch J. 2,7-Dihidroxy-3-formyl-1-(3′-methyl-2′-butenyl)carbazole from Clausena lansium .  Phytochemistry. 1995;  40 1563-5
    CrossrefPubMedGoogle Scholar
  • 11 Brown N MD, Grundon M F, Harrinson D M, Surgenor S A. Quinoline alkaloids - XXI - The 13C-NMR spectra of hemiterpenoid quinoline alkaloids and related prenylquinolines.  Tetrahedron. 1980;  16 1579-84
    PubMedGoogle Scholar
  • 12 Domingues X A, Franco R, Garcia S, Merijanian A, Espinosa G, Tomez R S, Zolli A B. Coumarins and alkaloids of the Rutaceae Helietta parvolia (Gray) Benth. Rev. Latinoam.  Quim.. 1984;  17 60-2
    PubMedGoogle Scholar
  • 13 Konig W A, Ghercke B, Weseloh G. Determination of the absolute configuration of secondary alcohols with Horeau’s method including enantioselective gas chromatography.  Chirality. 1994;  6 141-7
    CrossrefPubMedGoogle Scholar
  • 14 Massada Y. Analysis of essential oil by gas chromatography and spectrometry. John Wiley & Sons New York; 1995
    Google Scholar
  • 15 Adams R. Identification of essential oil components by gas chromatography/mass spectroscopy. Allured Publishing, Co Carol Stream, Illinois; 1995: 469 pp
    Google Scholar
  • 16 Hofmans A L, Fuchs A. Direct bioautography on thin-layer chromatograms as a method for detecting fungitoxic substances.  Journal of Chromatography. 1970;  51 327-9
    CrossrefPubMedGoogle Scholar

Prof. Dr. Ademir Farias Morel

Departamento de Química

Universidade Federal de Santa Maria


Campus de Camobi - Santa Maria - RS

Brazil

Email: afmorel@base.ufsm.br

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