Chemical Investigation on the Volatile Part of the CO₂ Supercritical Fluid Extract of Infected <i>Aquilaria sinensis</i> (Chinese Agarwood)

Abstract

This work is focused on the characterization of the composition of a CO2 supercritical fluid extract of Aquilaria sinensis (Chinese agarwood) collected in the Dongguan area (China) and infected by mechanical methods. The constituents of this extract were analyzed by gas chromatography–mass spectrometry (GC-MS) and quantified accurately by gas chromatography with a flame ionization detector (GC-FID), using an internal reference and predicted response factors. Since a significant number of components of this extract remained non-identified after the initial GC-MS analysis of the whole extract, its fractionation by chromatography on silica gel helped to characterize several additional constituents by isolation and structural analysis by NMR spectroscopy. The main components are the classical agarwood chromones (Flindersia chromone and its mono-, di-, and trimethoxylated analogues (respectively, 11.01% and 0.11–4.02%) along with sesquiterpenic constituents typically found in agarwood essential oils, like baimuxinal (1.90%) and kusunol (1.24%), as well as less common selinane dialdehydes (1.58–2.27%) recently described in the literature. Moreover, the structure and stereochemistry of a new sesquiterpenic alcohol, 14β,15β-dimethyl-7αH-eremophila-9,11-dien-8β-ol (0.67%), was determined unambiguously by the combination of structural analysis (NMR, MS), hemisynthesis, and total synthesis, leading to dihydrokaranone and a neopetasane epimer.

Keywords

• agarwood
• <i>Aquilaria sinensis</i>
• supercritical fluid extraction
• eremophilane sesquiterpenoids
• neopetasane