Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Phytochemical Study of Fagraea spp. Uncovers a New Terpene Alkaloid with Anti-Inflammatory Properties1

Suciati A B , Lynette K. Lambert C , Benjamin P. Ross D , Myrna A. Deseo E and Mary J. Garson A F
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.

B Faculty of Pharmacy, Airlangga University, Surabaya, Indonesia.

C Centre for Advanced Imaging, The University of Queensland, Brisbane, Qld 4072, Australia.

D School of Pharmacy, The University of Queensland, Brisbane, Qld 4072, Australia.

E Centre for Phytochemistry and Pharmacology, Southern Cross University, PO Box 157, Lismore, NSW 2480, Australia.

F Corresponding author. Email: m.garson@uq.edu.au

Australian Journal of Chemistry 64(4) 489-494 https://doi.org/10.1071/CH10421
Submitted: 20 November 2010  Accepted: 6 January 2011   Published: 18 April 2011

Abstract

Phytochemical investigation of the stem bark of F. racemosa JACK ex WALL (Loganiaceae) from East Java, Indonesia, has resulted in the isolation of a new alkaloid fagraeoside along with the iridoid glycoside secologanoside. Fagraeoside may be derived from the condensation of secologanin with L-asparagine, and represents a rare example of a terpene alkaloid in which the amino acid component is non-aromatic. Investigation of three additional species of Fagraea provided known lignans, iridoid or secoiridoid glycosides, and flavanol-6-C-glucosides, thus it is likely that iridoid and secoiridoid glucosides are chemotaxonomic markers for the Fagraea genus. Fagraeoside inhibited the production of prostaglandin E2 in 3T3 murine fibroblasts (IC50 ~5.1 µM), and was not cytotoxic to this cell line or to a P388 murine leukaemia cell line. Selected isolated compounds, including fagraeoside, showed low to moderate activity in anti-acetylcholinesterase screening.


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