An unusual triterpene fatty acid conjugate from Dodonaea caespitosa

Andrew M. Bloomfield; Eugene Eades; Hendra Gunosewoyo; Alan D. Payne

doi:10.1071/CH25050

RESEARCH ARTICLE (Open Access)

Previous Contents Vol 78(8)

An unusual triterpene fatty acid conjugate from Dodonaea caespitosa

Andrew M. Bloomfield

^A , Eugene Eades ^B , Hendra Gunosewoyo

^C and Alan D. Payne

^A ^*

+ Author Affiliations

- Author Affiliations

^A School of Molecular and Life Sciences, Curtin University, GPO Box U1987, Perth, WA 6845, Australia.

^B Nowanup Education Centre, 284 Normans Road, Gairdner, WA 6337, Australia.

^C Curtin Medical School, Curtin University, GPO Box U1987, Perth, WA 6845, Australia.

^* Correspondence to: alan.payne@curtin.edu.au

Handling Editor: Anastasios Polyzos

Australian Journal of Chemistry 78, CH25050 https://doi.org/10.1071/CH25050

Submitted: 8 April 2025 Accepted: 21 July 2025 Published online: 12 August 2025

© 2025 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

An unusual triterpene fatty acid conjugate was isolated from the leaf resin of Dodonaea caespitosa. Its structure was formulated through spectroscopic analysis of the acetylated natural product and its hydrolysis products (p-hydroxydihydrocinnamic acid, (S)-(+)-8,16-dihydroxypalmitic acid and 30-hydroxybetulin). The stereochemistry of the hydroxyl at C8 of (S)-(+)-8,16-dihydroxypalmitic acid was determined by conversion to the known (S)-(+)-(8)-hydroxypalmitic acid using a Barton–McCombie deoxygenation reaction.

Keywords: 8,16-dihydroxyhexadexanoic acid, cutin monomer, Dodonaea, natural products elucidation, Nowanup, semisynthesis, triterpene, Western Australia.

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