Research Article: (3R,4S,5S,8S,10R,13R)-3-Hy­droxy­kaura-9(11),16-dien-18-oic acid

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Karren D. Beattie, Mohan M. Bhadbhade, Donald C. Craig, David N. Leach.

http://doi.org/10.1107/S1600536812002206

Abstract

The title compound, C20H28O3, was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti­opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol­ecule makes one intra- and one inter­molecular O—H⋯O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along [010]. The absolute configuration of the compound was assigned on the basis of optical rotation measurements.

Partial Text

For the characterization of related kaurane diterpenes, see: Reynolds et al. (1991 ▶); Piozzi et al. (1972 ▶). For literature on the occurrence of the 3S isomer of the title compound isolated from Ichthyothere terminalis and Pseudognaphalium cheiranthifolium, see: Bohlmann et al. (1982 ▶); Mendoza & Urzúa (1998 ▶). For the anti­bacterial activity of the 3S isomer, see: Mendoza et al. (1997 ▶). For phytopharmacological aspects of Centipeda cunninghamii, see: Campbell (1973 ▶); Cribb (1988 ▶); D’Amelio & Mirhom, (1998 ▶); Maiden (1975 ▶); Webb (1948 ▶). For optical rotation data of related compounds, see: Bohlmann et al. (1982 ▶); Brieskorn & Pöhlmann (1968 ▶); Reynolds et al. (1991 ▶).

 

Source:

http://doi.org/10.1107/S1600536812002206