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New amides fromSpilanthes oleracea

Neue Amide ausSpilanthes oleracea (Kurze Mitteilung)

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  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

In addition to the well known affinin [=spilanthol, (2E,6Z,8E)-deca-2,6,8-trienoic acid isobutylamide (1)], the corresponding 2-methyl-butylamide (2), and two new acetylenic alkamides were isolated fromSpilanthes oleracea L. by reversed phase medium pressure chromatography: (Z)-non-2-en-6,8-diynoic acid isobutylamide (3) and (Z)-dec-2-en-6,8-diynoic acid isobutylamide (4). The structures and their stereochemistries were elucidated by1H-NMR,13C-NMR (2 and3), MS, UV, IR, and CD (2). The chemotaxonomic significance of the distribution of alkamides within theCompositae tribeHeliantheae is briefly discussed.

Zusammenfassung

AusSpilanthes oleracea wurden neben dem seit langem bekannten Affinin [=Spilanthol, (2E,6Z,8E)-Deca-2,6,8-triensäureisobutylamid (1)] durch Umkehrphasen-Mitteldruckchromatographie das entsprechende 2-Methylbutylamid (2) und zwei neue acetylenische Alkamide isoliert: (Z)-Non-2-en-6,8-diinsäure-isobutylamid (3) und (Z)-Dec-2-en-6,8-diinsäure-isobutylamid (4). Die Strukturen und deren Stereochemie wurden mittels1H-NMR,13C-NMR (2 und3), MS, UV, IR und CD (2) aufgeklärt. Die chemotaxonomische Bedeutung der Verbreitung von Alkamiden innerhalb der Compositen-TribusHeliantheae wird kurz diskutiert.

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References

  1. Jacobson M., in: Naturally Occurring Insecticides (Jacobson M., Crosby D. G., eds.), p. 137. New York: Marcel Dekker. 1971.

    Google Scholar 

  2. Gerber E., Arch. Pharm.241, 270 (1903).

    Google Scholar 

  3. Jacobson M., Chem. Ind. (London)1957, 50.

  4. Crombie L.,Krasinski A. H. A.,Manzoor-i-Khuda M., J. Chem. Soc.1963, 4970.

  5. Greger H., Planta Med.50, 365 (1984).

    Google Scholar 

  6. Martin R., Becker H., Phytochemistry23, 1781 (1984).

    Google Scholar 

  7. Bohlmann F., Ziesche J., Robinson H., King R. M., Phytochemistry19, 1535 (1980).

    Google Scholar 

  8. Robinson H., Smithsonian Contributions to Botany51, 1 (1981).

    Google Scholar 

  9. Yasuda I., Takeya K., Itokawa H., Chem. Pharm. Bull.28, 2251 (1980).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Botany, University of Vienna, A-1030, Wien, Austria

    Harald Greger

  2. Institute of Organic Chemistry, University of Vienna, A-1090, Wien, Austria

    Otmar Hofer & Andreas Werner

Authors
  1. Harald Greger
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  2. Otmar Hofer
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  3. Andreas Werner
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Greger, H., Hofer, O. & Werner, A. New amides fromSpilanthes oleracea . Monatsh Chem 116, 273–277 (1985). https://doi.org/10.1007/BF00798463

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  • DOI: https://doi.org/10.1007/BF00798463

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