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

• Main Authors: Suciati, Lynette K. Lambert, Benjamin P. Ross, Myrna A. Deseo, Mary J. Garson
• Format: Article PeerReviewed
• Language: English; English; English
• Published: Commonwealth Scientific and Industrial Research Organization Publishing 2011
• Subjects: R Medicine; RS Pharmacy and materia medica
• Online Access: http://repository.unair.ac.id/93585/3/C-05%20Artikel.pdf; http://repository.unair.ac.id/93585/6/C-05%20Reviewer.pdf; http://repository.unair.ac.id/93585/4/C-05%20Result.pdf; http://repository.unair.ac.id/93585/; http://www.publish.csiro.au/CH/CH10421
• Institution: Universitas Airlangga

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.