Isomeric Enhancement of Davanone from Natural Davana Oil Aided by Supercritical Carbon Dioxide

Abstract

The chemical nature of davanone isolated from natural davana oil via packed column preparative supercritical fluid chromatography with a carbon dioxide-based mobile phase has been defined. Analyses used to characterize davanone included nuclear magnetic resonance spectroscopy, optical rotation, mass spectrometry, headspace solid-phase microextraction, enantiomeric purity via gas chromatography (GC), and GC-coupled olfactometry. For comparison, natural davana oil was subjected to the same types of measurements. The enriched davanone sample was nearly 100% optically pure. This indicates that fractionation of the davana oil with supercritical fluids at near room temperature had little effect on the optical integrity of the sample.

Essential oil composition and biological activity from Artemisia caerulescens subsp. densiflora (Viv.) Gamisans ex Kerguélen & Lambinon (Asteraceae), an endemic species in the habitat of La Maddalena Archipelago

“…densiflora were davana ethers, sesquiterpenoids containing two reduced furan rings, accounting together for 17.5% of the total composition. These components are formed from oxidation of davanone (Thomas & Dubini 1971) which is the main component of davana oil obtained from A. pallens (Coleman et al 2007). Davanone is also found in other Artemisia species (Perez-Alonso et al 2003;Ramezani et al 2004;Sadeghpour et al 2004;Vajs et al 2004), being of chemotaxonomic value.…”

Supercritical Fluid Chromatography as a Technique to Fractionate High-Valued Compounds from Lipids

“…Coleman et al [68] developed at analytical and semi-preparative scale a SFC method to purify davanone from davana oil using CO 2 as a mobile phase, and silica-based stationary phases. In optimal conditions davanone fraction was almost 100% pure from 30% to 60% purity starting material.…”

“…Ramirez et al [66,67]. The authors were able to fractionate carnosic acid and carnosol (main antioxidant compounds found at rosemary) using CO2 + 10% ethanol as a modifier and LC-diol 5 μm particle size stationary phase in-house packed at semi-preparative scale at 130 bar and 353 K. Coleman et al [68] developed at analytical and semi-preparative scale a SFC method to purify davanone from davana oil using CO2 as a mobile phase, and silica-based stationary phases. In optimal conditions davanone fraction was almost 100% pure from 30% to 60% purity starting material.…”

New Insights into the Chemical Composition, Pro‐Inflammatory Cytokine Inhibition Profile of Davana (Artemisia pallens Wall. ex DC.) Essential Oil and cis‐Davanone in Primary Macrophage Cells

“…It is also cultivated for its fragrant leaves and flowers, which are used in floral decorations and religious offerings. The essential oil extracted from blooming dried aerial parts by steam‐distillation (yield approximately 0.2 %), commonly referred to as davana oil (DO) in trade, is mainly used in the flavoring of cakes, pastries, tobacco, and also some beverages [11,12] . The DO is a brownish‐green, viscous liquid with a characteristic persistent balsamic, fruity sweet odor and complex composition [8] …”