Sylvatiins, acetylglucosylated hydrolysable tannins from the petals of Geranium sylvaticum show co-pigment effect

Abstract

Four hydrolysable tannins, named as sylvatiins A (1), B (2), C (3) and D (4), were isolated from the petals of Geranium sylvaticum. On the basis of spectrometric evidence of NMR analysis (1H NMR, 13C NMR, DQF-COSY, TOCSY, NOESY, HSQC and HMBC), circular dichroism (CD) and ESI-MS/MS, sylvatiins A, B and C were characterized as galloyl glucoses containing one or two acetylglucoses attached to the 3-OH of the galloyl group, whereas sylvatiin D was found to have a chebulinic acid core containing acetylglucose attached in a similar way. The potential of these compounds to act as defensive compounds against herbivores was evaluated using the radial diffusion assay that measures the protein precipitation capacity. In addition, the capacity of sylvatiins to act as co-pigments with anthocyanins of G. sylvaticum petals was measured in vitro at different pH values. Sylvatiins A and D maintained efficiently the purple flower color near the natural pH of petal cells. The amount of sylvatiins was changed according to the flower color; deep purple petals with higher amount of anthocyanin contained more sylvatiins A and C than whiter petals. It was concluded that G. sylvaticum petal cells may accumulate sylvatiins for intermolecular co-pigmentation purposes.