Primary flavonoids in marigold dye: extraction, structure and involvement in the dyeing process.

Flavonoids extracted from marigold flowers were investigated for their dyeing potential. Patulitrin (1) and patuletin (2) were isolated and their structures established using NMR and HPLC-MS. These compounds were identified as the main flavonoids present in the dyeing bath. Following the dyeing process, it was demonstrated that aglycone 2 bound more strongly to wool fibres than its glucoside 1. Moreover, analysis focused on 1 and 2 dynamics during plant growth revealed that these components were only found in flowers during and after flowering. The influence of growing location was also investigated and it appeared that cultivation under Mediterranean conditions enhanced biosynthesis of 1 and 2 . Finally, several solvents were tested for their potential to extract the flavonoids: the use of a water-ethanol mixture gave a high extraction efficiency and allowed selective extraction of 1 and 2. The implications of these results are discussed in relation to the development of marigold as a potential dyeing plant. (c) 2007 John Wiley & Sons, Ltd.