Pyrrolidinooxazolidine alkaloids from two species of ladybird beetles

Peter Radford, Athula Attygalle, Jerrold Meinwald, Scott R. Smedley, Thomas Eisner

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

From the mixture of alkaloids obtained from adults of two species of ladybird beetles, Epilachna varivestis and Epilachna borealis, a novel bicyclic alkaloid, 5-(12'-aminotridecyl)pyrrolidinooxazolidine [(5α,7aβ)- hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-dodecaneamine] (2) was characterized on the basis of spectrometric and synthetic investigations. This new alkaloid is related structurally to a monocyclic congener 1-(2- hydroxyethyl)-2-(12'-aminotridecyl)pyrrolidine (1), previously characterized from E. varivestis. Two additional alkaloids (lower homologs of 1 and 2) from E. borealis were characterized as 5-(10'-aminoundecyl)pyrrolidinooxazolidine [(5α,7aβ)-hexahydro-α-methylpyrrolo[2,1-b]oxazole-5-decaneamine] (7) and 1-(2-hydroxyethyl)-2(10'-aminoundecyl)pyrrolidine (8), on the basis of their mass spectra.

Original languageEnglish (US)
Pages (from-to)755-759
Number of pages5
JournalJournal of Natural Products
Volume60
Issue number8
DOIs
StatePublished - Aug 1 1997
Externally publishedYes

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Beetles
Alkaloids
Oxazoles
pyrrolidine

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Analytical Chemistry
  • Molecular Medicine
  • Complementary and alternative medicine
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

Cite this

Radford, Peter ; Attygalle, Athula ; Meinwald, Jerrold ; Smedley, Scott R. ; Eisner, Thomas. / Pyrrolidinooxazolidine alkaloids from two species of ladybird beetles. In: Journal of Natural Products. 1997 ; Vol. 60, No. 8. pp. 755-759.
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Pyrrolidinooxazolidine alkaloids from two species of ladybird beetles. / Radford, Peter; Attygalle, Athula; Meinwald, Jerrold; Smedley, Scott R.; Eisner, Thomas.

In: Journal of Natural Products, Vol. 60, No. 8, 01.08.1997, p. 755-759.

Research output: Contribution to journalArticle

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AU - Attygalle, Athula

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