Isolation and quantification of a new tuliposide (tuliposide D) by HPLC in Alstroemeria

From aqueous extracts of flowers, stems and leaves of 1 Brazilian and 15 Chilean Alstroemeria species, the content of a new tuliposide, named tuliposide D, was determined by isocratic reversed-phase high-performance liquid chromatography (RP-HPLC), using distilled water:methanol (80:20) as mobile phase. The compound was detected by a UV-detector at 208 nm. Tuliposide D was found in almost all Alstroemeria species investigated, although in very different amounts. Most species contained relatively small amounts of tuliposide D, especially in the leaves. However, A. hookeri ssp. cummingiana, A. presliana ssp. presliana, A. pseudospathulata and A. revoluta contained large amounts of tuliposide D in all plant parts. Tuliposide D was identified as 1,6-di-(4-hydroxy-2-methylenebutanoate)-beta-D-glucopyranose by UV, FAB-MS, 1H- and 13C-NMR. The content of the allergens 6-tuliposide A and tulipalin A was also determined by RP-HPLC and the possibility that tuliposide D is a further causative agent of allergic contact dermatitis in Alstroemeria is discussed.