Fatty acid profiles from forty-nine plant species that are potential new sources of γ-linolenic acid

Forty-nine plant species from Spain, belonging to the Boraginaceae, Scrophulariaceae, Onagraceae, and Ranunculaceae families, were surveyed in a search of new sources of γ-linolenic acid (18∶3ω6, GLA). Fatty acid profiles from seeds, stems, roots, flowers and leaves were determined. GLA was detected mainly in seed and root tissues. High GLA amounts were found in seeds of Boraginaceae species, with a maximum of 20.25% of total fatty acids in Myosotis nemorosa. Within the Scrophulariaceae the highest GLA content (10.17%) was found in Scrophularia sciophila. Variable amounts of stearidonic acid, (18∶4ω3, SDA) were present in Boraginaceae species, ranging from 0.08% of total seed fatty acids in Anchusa azurea to 21.06% in Echium asperrimum. SDA was also very abundant in all organs of Asperugo procumbens. A multivariate analysis was performed using our results and those reported for other plant species belonging to the same families in order to investigate a possible correlation between the fatty acid profile and the genera within these families.     

Investigation of Chemical Constituents of Eranthis longistipitata (Ranunculaceae): Coumarins and Furochromones

Aqueous-ethanol extracts (70%) from the leaves of Eranthis longistipitata Regel. (Ranunculaceae Juss.)—collected from natural populations of Kyrgyzstan—were studied by liquid chromatography with high-resolution mass spectrometry (LC-HRMS). There was no variation of the metabolic profiles among plants that were collected from different populations. More than 160 compounds were found in the leaves, of which 72 were identified to the class level and 58 to the individual-compound level. The class of flavonoids proved to be the most widely represented (19 compounds), including six aglycones [quercetin, kaempferol, aromadendrin, 6-methoxytaxifolin, phloretin, and (+)-catechin] and mono- and diglycosides (the other 13 compounds). In the analyzed samples of E. longistipitata, 14 fatty acid–related compounds were identified, but coumarins and furochromones that were found in E. longistipitata were the most interesting result; furochromones khelloside, khellin, visnagin, and cimifugin were found in E. longistipitata for the first time. Coumarins 5,7-dihydroxy-4-methylcoumarin, scoparone, fraxetin, and luvangetin and furochromones methoxsalen, 5-O-methylvisammioside, and visamminol-3′-O-glucoside were detected for the first time in the genus Eranthis Salisb. For all the above compounds, the structural formulas are given. Furthermore, detailed information (with structural formulas) is provided on the diversity of chromones and furochromones in other representatives of Eranthis. The presence of chromones in plants of the genus Eranthis confirms its closeness to the genus Actaea L. because chromones are synthesized by normal physiological processes only in these members of the Ranunculaceae family.     

The distribution of fatty acids in the seed oils of the compositae,liliaceae, ranunculaceae and sapindaceae families

The oil content and fatty acid composition of the seed oils of Compositae (five species), Goodeniaceae (three species), Liliaceae (three species), Ranunculaceae (three species) and Sapindaceae (three species) were determined. The fatty acid composition of the seed oils were analysed by gas chromatography. In the 17 species studied the seed oil fatty acids were dominated by linoleic acid (50.1–70–5%) followed by oleic (11.1–20–4%) and palmitic acids (9.0–13–3%), except in one species, Diplopeltis huegelii, in which oleic acid (35.1%) predominated.     

Lipid cues for seed-carrying by ants inHepatica americana

We investigated the chemical basis for ants carrying the seeds ofHepatica americana, an ant-dispersed plant of eastern North America. A laboratory bioassay of seed and elaiosome extracts was based on the distance test items were carried byPogonomyrmex rugosus. Ants responded equally to isolated elaiosomes and to the diglyceride fraction. Diolein was a major component of the diglyceride fraction, which is consistent with a finding that 1,2-diolein releases seed-carrying byAphaenogaster rudis. Ants' response to the free fatty acid fraction was less intense. Gas chromatography of the fatty acid fraction indicated that oleic acid was a primary component, and oleic acid is known to elicit necrophoric behavior. No evidence supports an earlier suggestion that ricinoleic acid stimulates seed-carrying behavior. Ants failed to respond to seeds from which elaiosomes were removed.     

拟康定乌头中二萜生物碱成分及拒食活性

[目的]为了研究拟康定乌头中化学成分及其拒食活性.[方法]利用正反相硅胶柱层析进行分离纯化,结合HR-ESIMS、IR、1D和2D NMR等波谱技术对分离得到的化合物结构进行鉴定,采用叶碟法测试了其中10个化合物对甜菜夜蛾3龄幼虫的拒食活性.[结果]共分离得到15个二萜生物碱.其中10个化合物均存在一定的拒食活性.[结...     

Genomic Resources of Three Pulsatilla Species Reveal Evolutionary Hotspots,Species-Specific Sites and Variable Plastid Structure in the Family Ranunculaceae

Background: The European continent is presently colonized by nine species of the genus Pulsatilla, five of which are encountered only in mountainous regions of southwest and south-central Europe. The remaining four species inhabit lowlands in the north-central and eastern parts of the continent. Most plants of the genus Pulsatilla are rare and endangered, which is why most research efforts focused on their biology, ecology and hybridization. The objective of this study was to develop genomic resources, including complete plastid genomes and nuclear rRNA clusters, for three sympatric Pulsatilla species that are most commonly found in Central Europe. The results will supply valuable information about genetic variation, which can be used in the process of designing primers for population studies and conservation genetics research. The complete plastid genomes together with the nuclear rRNA cluster can serve as a useful tool in hybridization studies. Methodology/principal findings: Six complete plastid genomes and nuclear rRNA clusters were sequenced from three species of Pulsatilla using the Illumina sequencing technology. Four junctions between single copy regions and inverted repeats and junctions between the identified locally-collinear blocks (LCB) were confirmed by Sanger sequencing. Pulsatilla genomes of 120 unique genes had a total length of approximately 161–162 kb, and 21 were duplicated in the inverted repeats (IR) region. Comparative plastid genomes of newly-sequenced Pulsatilla and the previously-identified plastomes of Aconitum and Ranunculus species belonging to the family Ranunculaceae revealed several variations in the structure of the genome, but the gene content remained constant. The nuclear rRNA cluster (18S-ITS1-5.8S-ITS2-26S) of studied Pulsatilla species is 5795 bp long. Among five analyzed regions of the rRNA cluster, only Internal Transcribed Spacer 2 (ITS2) enabled the molecular delimitation of closely-related Pulsatilla patens and Pulsatilla vernalis. Conclusions/significance: The determination of complete plastid genome and nuclear rRNA cluster sequences in three species of the genus Pulsatilla is an important contribution to our knowledge of the evolution and phylogeography of those endangered taxa. The resulting data can be used to identify regions that are particularly useful for barcoding, phylogenetic and phylogeographic studies. The investigated taxa can be identified at each stage of development based on their species-specific SNPs. The nuclear and plastid genomic resources enable advanced studies on hybridization, including identification of parent species, including their roles in that process. The identified nonsynonymous mutations could play an important role in adaptations to changing environments. The results of the study will also provide valuable information about the evolution of the plastome structure in the family Ranunculaceae.     

Sequestration of Furostanol Saponins by <Emphasis Type="Italic">Monophadnus</Emphasis> Sawfly Larvae

Sawfly larvae of the tribe Phymatocerini (Hymenoptera: Tenthredinidae), which are specialized on toxic plants in the orders Liliales and Ranunculales, exude a droplet of deterrent hemolymph upon attack by a predator. We investigated whether secondary plant metabolites from Ranunculaceae leaves are sequestered by phymatocerine Monophadnus species, i.e., Monophadnus alpicola feeding upon Pulsatilla alpina and Monophadnus monticola feeding upon Ranunculus lanuginosus. Moreover, two undescribed Monophadnus species were studied: species A collected from Helleborus foetidus and species B collected from Helleborus viridis. Comparative high-performance liquid chromatographic–photodiode array detection–electrospray ionization–mass spectrometric analyses of plant leaf and insect hemolymph extracts revealed the presence of furostanol saponins in all samples. Larvae of species A and B actively sequestered (25R)-26-[(α-l-rhamnopyranosyl)oxy]-22α-methoxyfurost-5-en-3β-yl O-β-d-glucopyranosyl-(1→3)-O-[6-acetyl-β-d-glucopyranosyl-(1→3)]-O-β-d-glucopyranoside (compound 1). This compound occurred at a 65- to 200-fold higher concentration in the hemolymph of the two species (1.6 and 17.5 μmol/g FW, respectively) than in their host plant (0.008 and 0.268 μmol/g FW, respectively). In M. monticola, compound 1 was found at a concentration (1.2 μmol/g FW) similar to that in the host plant (1.36 μmol/g FW). The compound could not be detected consistently in M. alpicola larvae where, however, a related saponin may be present. Additional furostanol saponins were found in H. foetidus and H. viridis, but not in the two Monophadnus species feeding on them, indicating that sequestration of compound 1 is a highly specific process. In laboratory bioassays, crude hemolymph of three Monophadnus species showed a significant feeding deterrent activity against a potential predator, Myrmica rubra ant workers. Isolated furostanol saponins were also active against the ants, at a concentration range similar to that found in the hemolymph. Thus, these compounds seem to play a major role for chemical defense of Monophadnus larvae, although other plant secondary metabolites (glycosylated ecdysteroids) were also detected in their hemolymph. Physiological and ecological implications of the sequestered furostanol saponins are discussed. Dedicated to the memory of Professor Ivano Morelli (1940–2005)