A new natural spiro heterocyclic compound and the cytotoxic activity of the secondary metabolites from Juniperus brevifolia leaves

A new natural spiro compound 3,4-dehydrotheaspirone and the known arctiol [1β,6α-dihydroxy-4(14)-eudesmene] were isolated from Juniperus brevifolia. Arctiol is reported for the first time in the Juniperus genus. Their structures were established by 1D, and 2D NMR and MS spectra. Antimicrobial and cytotoxic activities of 1 and several secondary metabolites ,,,,,,,,, previously isolated by our group from J. brevifolia were evaluated and some SAR has been established. The 18-hydroxydehydroabietane (4) displayed great antiproliferative activity against cancer cell lines tested, namely HeLa, A-549 and MCF-7. Compound 4 also presented a significant bactericidal effect against Bacillus cereus at different concentrations tested.     

Population genetic structure of <Emphasis Type="Italic">Juniperus phoenicea</Emphasis> (Cupressaceae) in the western Mediterranean Basin: gradient of diversity on a broad geographical scale

• Introduction, Material and Methods  

The genetic structure and diversity of ten natural populations of Juniperus phoenicea L. from the western part of the species range have been studied using random amplified polymorphic DNA (RAPD) markers.     

Correction to: Phenotypic and marker-assisted characterization of new apple genotypes with high resistance to fire blight

European Journal of Plant Pathology - A Correction to this paper has been published: https://doi.org/10.1007/s10658-021-02315-7     

Higher taxa surrogates of spider (Araneae) diversity and their efficiency in conservation

A number of alternative approaches have been suggested during recent years to predict species richness of a given taxa, while retaining information on the identities of the observed individuals. Such information can be extremely useful for choosing conservation priority areas, either by using simple richness values or, preferentially, by considering the complementarity of potential sites. Among the most popular approaches is the use of higher taxa surrogates. Both family and genus richness are here tested in their ability to predict the number of spider (Araneae) species independently of sampling effort, geographical location and type of habitat. We use data from three Portuguese protected areas as a test case. Genus richness is considered a good surrogate of species richness, despite some caution being needed regarding the comparison of sites with considerably different sampling effort, the same not happening with families. Only genera are also found to be reliable either for ranking sites according to taxa richness or for determining near-minimum sets of sites for conservation. We therefore recommend surrogacy at this taxonomic level as a promising approach for the prediction of spider species richness or evaluation and ranking of areas according to their conservation importance. The reached conclusions should uphold for Portugal and the entire Mediterranean region.     

Heat expanded starch-based compositions

A heat expansion process similar to that used for expanded bead polystyrene was used to expand starch-based compositions. Foam beads made by solvent extraction had the appearance of polystyrene beads but did not expand when heated due to an open-cell structure. Nonporous beads, pellets, or particles were made by extrusion or by drying and milling cooked starch slurries. The samples expanded into a low-density foam by heating 190-210 degrees C for more than 20 s at ambient pressures. Formulations containing starch (50-85%), sorbitol (5-15%), glycerol (4-12%), ethylene vinyl alcohol (EVAL, 5-15%), and water (10-20%) were studied. The bulk density was negatively correlated to sorbitol, glycerol, and water content. Increasing the EVAL content increased the bulk density, especially at concentrations higher than 15%. Poly(vinyl alcohol) (PVAL) increased the bulk density more than EVAL. The bulk density was lowest in samples made of wheat and potato starch as compared to corn starch. The expansion temperature for the starch pellets decreased more than 20 degrees C as the moisture content was increased from 10 to 25%. The addition of EVAL in the formulations decreased the equilibrium moisture content of the foam and reduced the water absorption during a 1 h soaking period.     

Polyzyklische Aromatische Kohlenwasserstoffe (PAKs) in den Böden der Rieselfelder der Stadt Münster (Westfalen)

Polycyclic Aromatic Hydrocarbons (PAHs) in soils of the Münster (Westfalia) irrigation fields From 1901 to 1975 municipal sewage waters with a daily amount of finally about 40.000 m³ were seeped in the irrigation fields of the city of Münster (Westfalia). Soil samples of former seeped sites and non-seeped neighbour sites have been examined with regard to 6 polycyclic aromatic hydrocarbons (PAHs) of the German “drinking water regulation”. The irrigation caused an enrichment of PAH in the topsoils of the former irrigation basins up to an average concentration of 0,57 mg PAH/kg soil, while the topsoils outside of the irrigation fields show an average concentration of only 0,14 mg PAH/kg soil. Significant correlations between different soil properties, e.g. the organic matter content, and the concentration of PAHs are not evident. After termination the irrigation of sewage water, single irrigation bassins were filled with substratum, which is contaminated with scoriaceous materials. The average PAH concentration of such an area amounts to 7 mg PAH/kg topsoil. The PAH distribution in a soil profile shows a decreasing concentration by depth but a clear enrichment in oxidized gleyic horizons (Go) of different age. Probably the PAHs were leached under recent conditions by chemical bond to dissolved organic carbon (DOC) and finally adsorbed by Fe oxides. Since the end of irrigation Fluoranthene, the most mobile PAH compound, was leached down to 110 cm depth. A contamination of the superficial groundwater at such sites cannot be excluded.     

Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol pigments occurring in aging red wines

Three newly formed pigments were detected and isolated from a 2-year-old Port wine through TSK Toyopearl HW-40(S) gel column chromatography and characterized by UV-visible spectrophotometry, NMR, and mass spectrometry (ESI/MS). (1)H NMR and (13)C NMR data for these pigments obtained using 1D and 2D NMR techniques (COSY, NOESY, gHSQC, and gHMBC) are reported for the first time. The structure of the pigments was found to correspond to the vinyl cycloadducts of malvidin 3-coumaroylglucoside bearing either a procyanidin dimer or a flavanol monomer ((+)-catechin or (-)-epicatechin). Additionally, conformational analysis was performed for one of these newly formed pigment using computer-assisted model building and molecular mechanics. A chemical nomenclature is proposed to unambiguously name this new family of anthocyanin-derived pigments.     

Characterization of globulins from common vetch (Vicia sativa L.)

The proteins from Vicia sativa L. (common vetch) seeds were investigated. Protein comprises approximately 11.4% of the seed fresh weight, >50.8% of which is composed by globulins and 43.6% by albumins. The globulins may be fractionated into two main components, which were named alpha-vicinin (comprising 73% of the total globulin fraction, and hence >37% of the total seed protein) and beta-vicinin. Two minor globulin components are also present, gamma-vicinin and delta-vicinin. alpha-Vicinin, the legumin-like globulin, with a sedimentation coefficient of 10.6 S, is a nonglycosylated, disulfide-bond-containing globulin, composed of a group of subunits with molecular masses ranging from 50 to 78 kDa. Upon reduction, each of these subunits releases a heavy polypeptide chain (34-66 kDa) and a light polypeptide chain (21-23 kDa). beta-Vicinin, the vicilin-like globulin, with a sedimentation coefficient of 7.7 S, is a nonglycosylated globulin that contains no disulfide bonds and consists of two major polypeptides with molecular masses of 58 and 66 kDa. gamma-Vicinin is a minor, glycosylated, disulfide-bond-containing globulin. In the reduced form, it comprises six polypeptide chains with molecular masses of 12, 19, 21, 22, 23, and 31 kDa. Finally, delta-vicinin is a minor, highly glycosylated globulin that exhibits hemagglutinating activity. It is composed of a major 47 kDa polypeptide and two minor (33 and 38 kDa) polypeptides. N-terminal sequencing of the delta-vicinin 47 kDa polypeptide revealed no homology to any other known storage protein.     

Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins

Three new anthocyanin-derived pigments were found to occur in a 2-year-old Port red wine. Their structures were elucidated through LC/DAD-MS and NMR analysis and were found to correspond to a pyranoanthocyanin moiety linked to substituted cinnamyl substituents. The structures of these compounds are very similar to the one already reported for portisins, with a phenolic moiety replacing the catechin moiety. The newly formed anthocyanin-derived compounds display a bathochromic shift of the lambdamax ( approximately 540 nm) when compared with their anthocyanin-pyruvic acid adduct precursor (lambdamax = 511 nm), which may be due to the extended conjugation of the pi electrons in the structures of those pigments. Studies performed in model solutions helped to clarify the formation mechanism of these pigments that can result from the nucleophilic attack of the olefinic double bond of a hydroxycinnamic acid to the eletrophilic C-10 position of the anthocyanin-pyruvic acid adduct, followed by the loss of a formic acid molecule and decarboxylation. The chromatic characterization of these malvidin-3-glucoside-derived compounds revealed a higher resistance to discoloration against the nucleophilic attack by water and bisulfite when compared to malvidin-3-glucoside that is almost converted into its colorless hemiacetal form. However, the resistance to discoloration of these new pigments is not as high as the one reported for catechin-derived portisins. This could be explained by the presence of a smaller group (hydroxycinnamyl group), which does not protect so efficiently the chromophore against nucleophilic attack at the C-2 position. The occurrence of these pigments in red wine highlights new chemical pathways involving anthocyanin-pyruvic acid derivatives as precursors for the formation of new pigments in subsequent stages of wine aging that may contribute to its color evolution.     

Environmental conditions during vegetative growth determine the major proteins that accumulate in mature grapes

Despite recent reports in the literature that chitinases comprise approximately 50% of the soluble proteins present in mature Vitis vinifera L. (cv. Moscatel) grapes, with the other major proteins being thaumatin-like proteins, a careful inspection of the published data reveals inconsistencies as to which proteins actually accumulate in mature grapes. Mature Moscatel grapes were harvested in the same vineyard in two consecutive years, 1999 and 2000. The grapes exhibited widely distinct polypeptide patterns when analyzed by either FPLC cation exchange chromatography or two-dimensional electrophoresis: whrereas the 2000 grapes possessed a much higher protein content (1.96 versus 1.11 mg g(-)(1) of fresh weight), the 1999 grapes contained a greater heterogeneity of polypeptides. In addition, highly specific antibodies that recognize the pathogenesis-related proteins present in the grapes demonstrated that the 2000 harvest grapes had a wider variety of pathogenesis-related polypeptides. N-Terminal sequencing of the major polypeptides revealed differences in the relative abundance and amino acid sequence of thaumatin-like and osmotin-like polypeptides present in the 1999 and 2000 harvest Moscatel grapes and did not detect the presence of chitinase. As a whole, the data indicate that the expression and accumulation of the major proteins in grapes is essentially determined by the environmental and/or pathological conditions prevailing during grape development and maturation. The potential physiological and technological implications are discussed. The results of the present work suggest that it is not possible to base varietal differentiation of grapes on the profile of the pathogenesis-related polypeptides present in the mature berries.