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.


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 ▶).