Cytotoxic constituents of roots of Chaerophyllum hirsutum.

Two new lignan derivatives (1 and 2), along with the known scopoletin (3), methyl caffeate (4), falcarindiol (5), 3,5-dicaffeoylquinic acid, 3,5-dicaffeoylquinic methyl ester, chlorogenic acid, p-hydroxyphenylethyl-trans-ferulate, and vanillin, were isolated from extracts of the roots of Chaerophyllum hirsutum. Structure elucidation of the new compounds was carried out by 1D and 2D NMR experiments and by HRMS analysis. Several of the isolated compounds were tested for their cytotoxic activity against the HL-60, HT-1080, LoVo, and LoVo/Doxo cell lines.

Detection of hypericins in the "red glands" of Hypericum elodes by ESI-MS/MS.

The biologically active naphthodianthrones hypericin and pseudohypericin were detected by electrospray ionization mass spectrometry (ESI-MS/MS) in microsamples from the sepals of Hypericum elodes (Hypericaceae) containing the so-called "red glands", i.e. stipitate glands with red-coloured heads. The occurrence of hypericins in the red glands of H. elodes supports the taxonomic position of the section Elodes within the genus Hypericum and provides evidence that the ability of carrying out the biosynthetic pathway leading to the naphthodianthrone compounds, rather than the absolute amounts produced, should be regarded as a chemical marker of the phylogenetically more advanced sections of genus Hypericum. The biologically active phloroglucinol derivatives hyperforin and adhyperforin, so far found only in H. perforatum, were also detected and evidence for their localization in the sepal secretory canals with large lumen, is given.

Xanthones from Polygala alpestris (Rchb.).

Bioactivity-guided fractionation of Polygala alpestris L. (Rchb.) extracts led to the identification of two new xanthones, 1,3,7-trihydroxy-2,6-dimethoxyxanthone (1) and 2,3-methylenedioxy-4,7-dihydroxyxanthone (2). In addition five known compounds 3,4-dimethoxy-1,7-dihydroxyxanthone (3), 1,3-dihydroxy-7-methoxyxanthone (4), 1,7-dihydroxy-2,3-dimethoxyxanthone (5), 3',6-O-disinapoyl sucrose (6) and 3',5'-dimethoxybiphenyl-4-olo (7) were isolated. The structures of the isolated compounds were established by means of high resolution mass spectrometry, mono- and bi-dimensional NMR spectroscopy. All isolated compounds were tested for cytotoxic activity against three tumor cell lines (LoVo, HL-60, K 562).

Cytotoxic compounds from Polygala vulgaris.

To search for antitumor agents from plants, we studied Polygala vulgaris since cytotoxic lignans are known to occur in some Polygala species. Preliminary data on plant petrol ether, chloroform, and methanol extracts from the roots and aerial parts, showed in vitro cytotoxic activity against the solid tumor LoVo cell line. Fractionation of the active extracts led to the isolation of three new compounds, a derivative of aucuparine and two xanthones, as well as a known methylsinapate. All compounds were tested for in vitro cytotoxic activity using two cell lines, LoVo and its strain, which express resistance to common antitumor agents.

Patavine, a new arylnaphthalene lignan glycoside from shoot cultures of Haplophyllum patavinum.

A new arylnaphthalene lignan glycoside, patavine (1), together with five known lignans, justicidin B (2), diphyllin (3), tuberculatin (4), majidine (5), and arabelline (6) were isolated from shoot cultures of Haplophyllum patavinum. The structure of the new compound was elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. The cytotoxicity of compounds 1, and 3-6 against LoVo human colon carcinoma cells was investigated.