Title

Phytochemical study of fagraea spp. Uncovers a new terpene alkaloid with anti-inflammatory properties1

Document Type

Article

Publication details

Suciati, Lambert, LK, Ross, BP, Deseo, MA & Garson, MJ 2011, 'Phytochemical study of fagraea spp. Uncovers a new terpene alkaloid with anti-inflammatory properties', Australian Journal of Chemistry, vol. 64, no. 4, pp. 489-94.

The publisher's version of this article is available at

http://dx.doi.org/10.1071/CH10421

Peer Reviewed

Peer-Reviewed

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 ofFagraea 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.