TY - JOUR
T1 - Phytochemical study of Fagraea spp. Uncovers a new terpene alkaloid with anti-inflammatory properties
AU - Suciati,
AU - Lambert, Lynette K.
AU - Ross, Benjamin P.
AU - Deseo, Myrna A.
AU - Garson, Mary J.
N1 - Funding Information:
The authors thank AusAID for the award of an Australian Development Scholarship, The Queensland Pharmacy Research Trust (Pharmaceutical Society of Australia, Queensland branch) for financial support for the acetylcholinesterase inhibition assay, and Dr Achmad Fuad (Faculty of Pharmacy, Airlangga University, Surabaya, Indonesia) for the F. auriculata sample. We thank Dr Patricia Hayes for assistance with the enantioselective GC characterisation of D-glucose. Mr Graham McFarlane and Dr Tri Le assisted with MS and NMR measurements respectively.
PY - 2011
Y1 - 2011
N2 - 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 ∼5.1M), 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.
AB - 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 ∼5.1M), 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.
UR - http://www.scopus.com/inward/record.url?scp=79955121988&partnerID=8YFLogxK
U2 - 10.1071/CH10421
DO - 10.1071/CH10421
M3 - Article
AN - SCOPUS:79955121988
SN - 0004-9425
VL - 64
SP - 489
EP - 494
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 4
ER -