Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1

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

Research output: Contribution to journalArticle

15 Citations (Scopus)

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 - Jan 1 1984

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Lignans
Lactones
Araliaceae
Isomerization
Functional groups
Hot Temperature
Experiments
Derivatives
neoisostegane
stegane

ASJC Scopus subject areas

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

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

Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1 . / Taafrout, Mohammed; Rouessac, Francis; Robin, Jean Pierre; Hicks, Rickey Paige; Shillady, Donald D.; Sneden, Albert T.

In: Journal of Natural Products, Vol. 47, No. 4, 01.01.1984, p. 600-606.

Research output: Contribution to journalArticle

Taafrout, M, Rouessac, F, Robin, JP, Hicks, RP, Shillady, DD & Sneden, AT 1984, 'Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1 ', Journal of Natural Products, vol. 47, no. 4, pp. 600-606. https://doi.org/10.1021/np50034a005
Taafrout, Mohammed ; Rouessac, Francis ; Robin, Jean Pierre ; Hicks, Rickey Paige ; Shillady, Donald D. ; Sneden, Albert T. / Neoisostegane, A New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia Araliacea1 In: Journal of Natural Products. 1984 ; Vol. 47, No. 4. pp. 600-606.
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