A tocotrienol series with an oxidative terminal prenyl unit from Garcinia amplexicaulis.

Alexis Lavaud (1, 2) , Pascal Richomme (2) , Julia Gatto (2) , Marie-Christine Aumond (2) , Cyril Poullain (3) , Marc Litaudon (3) , Ramaroson Andriantsitohaina (1) , David Guilet (2)

1 SOPAM - Stress Oxydant et Pathologies Métaboliques
2 SONAS - Substances d'Origine Naturelle et Analogues Structuraux
3 ICSN - Institut de Chimie des Substances Naturelles

Ten tocotrienol derivatives, i.e., amplexichromanols (1-10), were isolated from stem bark of Garcinia amplexicaulis Vieill. ex Pierre collected in Caledonia. The structures of the compounds 1-5 were determined to be chromanol derivatives substituted by a polyprenyl chain oxidized in terminal position. The remaining compounds 6-10 are the corresponding dimeric derivatives. Eleven known compounds, including xanthones, tocotrienol derivatives, triterpenes and phenolic compounds, were also isolated. Their structures were mainly determined using one and two-dimensional NMR and mass spectroscopy analysis. The compounds and some amplexichromanol molecules formerly isolated from G. amplexicaulis exhibited significant antioxidant activity against lipid peroxidation and in the ORAC assay.

Mots clés: Tocotrienols; Inhibition of lipid peroxidation; Chromanols; Clusiaceae; Garcinia amplexicaulis

Domaines: Chimie

Alexis Lavaud, Pascal Richomme, Julia Gatto, Marie-Christine Aumond, Cyril Poullain, et al.. A tocotrienol series with an oxidative terminal prenyl unit from Garcinia amplexicaulis.. Phytochemistry, 2014, 109, pp.103-110. ⟨10.1016/j.phytochem.2014.10.024⟩. ⟨hal-01113163⟩