Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1

Mohammed Taafrout, Francis Rouessac, Jean Pierre Robin, Rickey P. Hicks, Donald D. Shillady, Albert T. Sneden

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Neoisostegane, the first naturally occurring steganin without a functional group at C-5, was isolated from two different collections of Steganotaenia araliacea. The structure of neoisostegane, which contained five aromatic methoxyl groups rather than the more usual three methoxyls and one methylenedioxy moiety, was elucidated by comparison of the pmr coupling constants with those of synthetic steganes and by selective decoupling experiments. The structure was confirmed by cmr data, by preparation of a derivative having five aromatic methoxyl moieties from stegane, which was compared spectroscopically to neoisostegane, and by thermal isomerization experiments.

Original languageEnglish (US)
Pages (from-to)600-606
Number of pages7
JournalJournal of Natural Products
Volume47
Issue number4
DOIs
StatePublished - May 1984

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea<sup>1</sup>'. Together they form a unique fingerprint.

  • Cite this

    Taafrout, M., Rouessac, F., Robin, J. P., Hicks, R. P., Shillady, D. D., & Sneden, A. T. (1984). Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1. Journal of Natural Products, 47(4), 600-606. https://doi.org/10.1021/np50034a005