Cytotoxic Natural Products Isolated from Cryptogramma crispa (L.) R. Br.

Parsley fern, Cryptogramma crispa, is a common fern in arctic-alpine regions, and even though this species has been known since ancient times and has been presumed to cause the poisoning of horses, its natural products have not previously been investigated. Here, we characterise 15 natural products isolated from the aerial parts of Cryptogramma crispa, including the previously undescribed compound 3-malonyl pteroside D. The structure determinations were based on several advanced 1D and 2D NMR spectroscopic techniques, Circular Dichroism spectroscopy and high-resolution mass spectrometry. The pteroside derivatives exhibited selective moderate cytotoxic activity against the acute myeloid leukaemia MOLM13 cell line and no cytotoxicity against the normal heart and kidney cell lines, suggesting that their potential anticancer effect should be further investigated.

A novel bicyclic lactone and other polyphenols from the commercially important vegetable Anthriscus cerefolium.

Garden chervil, Anthriscus cerefolium (L.) Hoffm. is an important herb commonly applied in Norwegian large-scale commercial kitchens. This species is a highly enriched source of phenolics, containing 1260 mg gallic acid equivalents (GAE) 100-1 g DM, however, the individual phenolic compounds have been scarcely characterized. Here we report on the qualitative and quantitative content of phenolics in garden chervil. The structure of the main phenolic compound was elucidated to be the previously undescribed compound 1,3-dicaffeoyl-5-malonyl-δ-quinide (1) by means of 1D- and 2D NMR and high-resolution mass spectrometry. The known flavones apigenin 7-O-ß-(2″-apiofuranosylglucopyranoside) (= apiin) (2), apigenin 7-(2″-apiosyl-6″-malonylglucoside) (3) and luteolin 7-glucoside (4) were also identified. Compound 3 is reported for the first time from this plant species. The main phenolic compound, 1,3-dicaffeoyl-5-malonyl-δ-quinide, exhibited moderate cytotoxicity towards acute monocytic leukaemia cells (MOLM-13) and rat kidney epithelial cells (NRK) with EC50 between 400 and 600 µM.