Daucovirgolides I-L, four congeners of the antimalarial daucovirgolide G from Daucus virgatus.

Repeated chromatographic purifications of aerial parts of the Tunisian plant Daucus virgatus led to the isolation of four new germacranolides, named daucovirgolides I-L (2-5), along with the Plasmodium transmission-blocking agent daucovirgolide G. The chemical structures of the new compounds were defined as mono- or di-angeloylated germacrane-type sesquiterpenoids by spectroscopic (mainly 1D and 2D NMR) and spectrometric methods (ESIMS). The low potency exhibited by daucovirgolides I-L further supports the observation that strict structural requirements do exist for the Plasmodium transmission blocking activity in the daucovirgolide series. In particular, the endocyclic double bond system seems to be crucial for bioactivity.

Angeloylated Germacranolides from Daucus virgatus and Their Plasmodium Transmission Blocking Activity.

Phytochemical investigation of the aerial parts of the Tunisian plant Daucus virgatus led to the isolation of eight new germacranolides named daucovirgolides A-H (1-8). The stereostructures of these sesquiterpene lactones, decorated by either one or two angeloyl groups, have been determined by a combination of MS, NMR spectroscopy, chemical derivatization, and comparison of experimental electronic circular dichroism curves with TDDFT-predicted data. Daucovirgolide G (7) proved to be the single member of this family to possess a marked inhibitory activity (92% at 50 µg/mL) on the development of Plasmodium early sporogonic stages, the nonpathogenic transmissible stages of malaria parasites, devoid of general cytotoxicity. The selective activity of daucovirgolide G points to the existence of strict structural requirements for this transmission-blocking activity and therefore of a well-defined, although yet unidentified, biological target.

Antiproliferative metabolites from the Northern African endemic plant Daucus virgatus (Apiaceae).

Chemical analysis of the dichloromethane fraction obtained from aerial parts of the Northern African endemic plant Daucus virgatus led to the isolation of three previously undescribed sesquiterpenoids, namely the daucane vaginatin B, a eudesmane and the elemane elemavirgolide, along with five known metabolites. The structures of these compounds were determined by a detailed MS and NMR analysis and they were evaluated for antiproliferative activity against three human cell lines, A375 (melanoma), MCF-7 (breast adenocarcinoma), and HACAT (keratinocyte). The phytoalexin 6-methoxymellein revealed a previously unreported antiproliferative activity, while the eudesmane and the elemane derivatives exhibited a selective activity (SI = 11.1 and 3.3, respectively) against melanoma tumor cell lines.

Essential Oil Constituents and Antioxidant Activity of Asplenium Ferns.

Two fern species Asplenium adiantum-nigrum L. and Asplenium trichomanes L. collected from the Kroumiria region (Northwest of Tunisia) were individually submitted to hydrodistillation in a Clevenger type apparatus. Volatile organic compounds were identified by GC-MS and GC-FID. Thus, 35 compounds were identified in A. adiantum-nigrum essential oil accounting for 77.5% of the whole constituents dominated by palmitic acid (34.5%); however, only 29 volatiles were identified in A. trichomanes showing a high amount of phytol, an odorous diterpene alcohol, representing 14.4% of the total oil contents. The total phenolic content and the antioxidant effects of crude extracts from both pteridophytes were determined using Folin-Ciocalteu and 2,2'-diphenyl-1-picrylhydrazyl free radical-scavenging assays, respectively. A. adiantum-nigrum ethyl acetate extract is shown to be lower in total phenolic contents (49.3 mg gallic acid equivalent/g) than similar extract from A. trichomanes (55.4 mg GAE/g).