A New Prenylated Flavanonol from Seseli annuum Roots Showing Protective Effect on Human Lymphocytes DNA

A new prenylated flavanonol named seselinonol ( 1 ) was isolated from the roots of Seseli annuum, together with the well‐known biologically active polyacetylenes falcarinol ( 2 ) and falcarindiol ( 3 ), and the prenylated furanocoumarin phellopterin ( 4 ). Its structure was elucidated by extensive spectroscopic analysis, including HR‐ESI‐MS, 1D‐ and 2D‐NMR. Seselinonol and phellopterin were tested for in vitro protective effect on chromosome aberrations in peripheral human lymphocytes using cytochalasin‐B blocked micronucleus (CBMN) assay. The new compound exerted a beneficial effect by decreasing DNA damage of human lymphocytes.     

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

The chemical composition, antibacterial and antioxidant activities of the essential oil obtained from Eryngium triquetrum from Algeria were studied. The chemical composition of sample oils from 25 locations was investigated using GC‐FID and GC/MS. Twenty‐four components representing always more than 87% were identified in essential oils from total aerial parts of plants, stems, flowers and roots. Falcarinol is highly dominant in the essential oil from the roots (95.5%). The relative abundance of falcarinol in the aerial parts correlates with the phenological stages of the plant. Aerial parts of E. triquetrum produce an essential oil dominated by falcarinol during the early flowering stage, and then there is a decrease in falcarinol and rebalancing of octanal during the flowering stage. To our knowledge, the present study is the first report of the chemical composition of E. triquetrum essential oil. Evaluation of the antibacterial activity by means of the paper disc diffusion method and minimum inhibitory concentration assays, showed a moderate efficiency of E. triquetrum essential oil. Using the DPPH method, the interesting antioxidant activity of E. triquetrum essential oil was established. These activities could be attributed to the dominance of falcarinol. The outcome of our literature search on the occurrence of falcarinol in essential oils suggests that E. triquetrum from Algeria could be considered as a possible source of natural falcarinol.     

Variability of the Root Essential Oils of Seseli rigidum Waldst. & Kit. (Apiaceae) from Different Populations in Serbia

The chemical compositions of the essential oils of seven natural populations of Seseli rigidum were analyzed. The essential‐oil yield ranged from 0.16 to 2.09%. Analysis of variance (ANOVA) revealed that there were no statistically significant differences in the mean essential‐oil yields between the populations, and no significant influence of the climate or soil type on the oil yield was observed. In all 67 analyzed samples, the polyacetylene falcarinol was the main compound, followed by octanal, methyl linoleate, α‐muurolene, 3‐butylphthalide, falcarinone, muurola‐4,10(14)‐dien‐1β‐ol, β‐sesquiphellandrene, salvial‐4(14)‐en‐1‐one, δ‐amorphene, spathulenol, and isospathulenol. The principal component analysis (PCA), the canonical discriminant analysis (CDA), and the cluster analysis (CA) revealed differentiation between the populations based on the climate. Three groups of populations were formed; the first group was composed of samples growing in regions with a humid climate, with oils having high falcarinol and low sesquiterpene contents, and the second and third groups comprised samples exposed to semi‐arid climate, with oils characterized by a lower falcarinol and higher α‐muurolene, δ‐amorphene, β‐sesquiphellandrene, and salvial‐4(14)‐en‐1‐one contents. The semi‐arid populations were divided into two groups, which were distinguished based on the oil contents of sesquiterpenes, falcarinone, and 3‐butylphthalide. On the other hand, no clear separation between populations based on the different soil types could be observed.     

Chemical Composition of the Essential Oil and Diethyl Ether Extract of Trinia glauca (L.) Dumort. (Apiaceae) and the Chemotaxonomic Significance of 5‐O‐Methylvisamminol

Analyses by GC, GC/MS, and NMR spectroscopy (1D‐ and 2D‐experiments) of the essential oil and Et₂O extract of Trinia glauca (L .) Dumort . (Apiaceae) aerial parts allowed a successful identification of 220 constituents, in total. The major identified compounds of the essential oil were (Z)‐falcarinol (10.6%), bicyclogermacrene (8.0%), germacrene D (7.4%), δ‐cadinene (4.3%), and β‐caryophyllene (3.2%), whereas (Z)‐falcarinol (47.2%), nonacosane (7.4%), and 5‐O‐methylvisamminol (4.0%) were the dominant constituents of the extract of T. glauca. One significant difference between the compositions of the herein and the previously analyzed T. glauca essential oils (only two reports) was noted. (Z)‐Falcarinol was the major constituent in our case, whereas germacrene D (14.4 and 19.6%) was the major component of the previously studied oils. Possible explanations for this discrepancy were discussed. 5‐O‐Methylvisamminol, a (furo)chromone identified in the extract of T. glauca, has a limited occurrence in the plant kingdom and is a possible excellent chemotaxonomic marker (family and/or subfamily level) for Apiaceae.