Planta Med 2008; 74 - PB119
DOI: 10.1055/s-0028-1084464

New polyamine derivatives from Microdesmis keayana and Microdesmis puberula

V Roumy 1, T Hennebelle 1, A Zamblé 1, S Quarré 1, S Sahpaz 1, F Bailleul 1
  • 1Laboratoire de Pharmacognosie (E.A. 1043), Faculté de Pharmacie, Université de Lille 2, 59006 Lille Cedex, France

Microdesmis keayana J. Léonard and Microdesmis puberula Hook f. are two common species from the central African forest used in traditional medicine. The roots of both are used to remedy sexual dysfunction and the leaves are used against malaria [1], gastrointestinal parasites and various infections [2]. These two perennial shrubs belong to the Pandaceae family which has not been greatly explored. Recent studies on M. keayana have shown the roots to have hypotensive, antioxidant properties and stimulating effects on sexual behaviour in male rats. They have also revealed that polyamines such as the spermidine or spermine derivatives contained in the hydromethanolic extract are involved in these biological activities. Previous phytochemical works led to the isolation and identification of nitrogenous compounds as a 6-hydroxyquinoline-4-carboxamide, three N 1,N 5,N 10-tris(4-hydroxycinnamoyl)spermidines and a N 1,N 5,N 15-tris(4-hydroxycinnamoyl)spermine from hydromethanolic root extract of M. keayana [3,4]. In the continuation of our study on Microdesmis genus, the methanolic root extracts of M. keayana and M. puberula were investigated. The ESI-MS2 technique with specific NMR analysis of hydrolysed products made it possible to identify N 1,N 5,N 15-tris(p-coumaroyl)spermine, N 1-feruloyl, N 5,N 15-di(p-coumaroyl)spermine and

N 1,N 5,N 15-tris(feruloyl)spermine, named keayanines B, C and D, respectively. HPLC/ESI-MS2 of M. puberula hydromethanolic root extract was also used to characterise all three N 1,N 5,N 10-tris(4-hydroxycinnamoyl)spermidines and the N 1,N 5,N 15-tris(4-hydroxycinnamoyl)spermine previously described in M. keayana. These chemical data were the first to be reported for M. puberula.

R1=R2=R3=H

Keayanine B

R1=OCH3, R2=R3=H

Keayanine C

R1=R2=R3=OCH3

Keayanine D

References: 1. Kamanzi, K. et al. (2004)J. Ethnopharmacol. 90: 221–227.

2. Diehl, M.S. et al. (2004)J. Ethnopharmacol. 95: 277–284.

3. Zamblé, A. et al. (2007) Chem. Pharm. Bull. 55: 643–645.

4. Zamblé, A. et al. (2006) Chem. Biodivers. 3: 982–989.