Tremorgenic Indole Diterpenes from Ipomoea asarifolia and Ipomoea muelleri and the Identification of 6,7-Dehydro-11-hydroxy-12,13-epoxyterpendole A

J Nat Prod. 2018 Jul 27;81(7):1682-1686. doi: 10.1021/acs.jnatprod.8b00257. Epub 2018 Jul 16.

Abstract

Indole diterpene alkaloids have been isolated from Ipomoea asarifolia and I. muelleri and are associated with a tremorgenic syndrome in livestock. To better characterize the tremorgenic activity of the major indole diterpene alkaloids in these two plants, terpendole K (1), 6,7-dehydroterpendole A (2), 11-hydroxy-12,13-epoxyterpendole K (3), terpendole C (5), paxilline (6), and a new compound, 6,7-dehydro-11-hydroxy-12,13-epoxyterpendole A (4), were isolated and evaluated for tremorgenic activity in a mouse model. Compounds 1, 2, 5, and 6 all showed similar and significant signs of tremorgenic activity. In contrast, the 11-hydroxy-12,13-epoxy compounds, 3 and 4, showed no significant tremorgenic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Female
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology
  • Indoles / chemistry
  • Indoles / isolation & purification*
  • Indoles / pharmacology
  • Ipomoea / chemistry*
  • Mice
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Tremor / chemically induced*

Substances

  • Diterpenes
  • Indole Alkaloids
  • Indoles
  • Plant Extracts