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.

Keywords: Tocotrienols; Inhibition of lipid peroxidation; Chromanols; Clusiaceae; Garcinia amplexicaulis

Domains: Chemical Sciences

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⟩