Effects of flavonoids on membrane adaptation of food-associated bacteria.

The effects of naringenin and the biflavonoids amentoflavone and tetrahydroamentoflavone on select bacterial lipids (carotenoids, fatty acids, and menaquinones) and membrane fluidity based on Laurdan generalized polarization were investigated. For this purpose, the pigment-forming food-associated microorganisms Staphylococcus xylosus (DSM 20266T and J70), Staphylococcus carnosus DSM 20501T, and Micrococcus luteus (ATCC 9341 and J3) were studied. The results suggest an envelope stress response by microorganisms due to flavonoids and an employment of adaptive mechanisms using carotenoids, fatty acids, and menaquinones. The flavonoid monomer naringenin impacted carotenoids, fatty acids, menaquinones, and membrane fluidity. Naringenin significantly influenced the carotenoid profile, particularly by an increase in the relative proportion of 4,4'-diaponeurosporenoic acid in Staphylococcus xylosus. Amentoflavone caused changes mainly in the membrane of Micrococcus luteus and decreased the menaquinone content. Tetrahydroamentoflavone mainly affected the carotenoids in the investigated strains. The noticeably different CCS value of tetrahydroamentoflavone compared to naringenin and amentoflavone revealed further insights into the structure-dependent effects of flavonoids. This study provides valuable insights into the response of pigment-forming food-associated microorganisms to naringenin, amentoflavone, and tetrahydroamentoflavone, which is important for the targeted and safe application of the latter as natural preservatives and useful for further research on the mechanisms of action.

Free word association perceptions of red meats; beef is 'yummy', bison is 'lean game meat', horse is 'off limits'.

Reduced consumption of conventional red meats due to environmental and health concerns may create interest in less familiar red meats from alternative animal species. The objective of this study was to identify perceptions of three red meats; beef, a familiar meat, and bison and horse meat, less familiar red meat alternatives. A total of 145 western Canadian participants completed an on-line survey that included a free word association task, food variety seeking and food involvement scales, and meat consumption and demographic questions. The free word association yielded 41 word categories of diverging perceptions of the 3 meats. Beef was described with positive sensory attributes and well-liked foods, yet with environmental, ethical and production concerns, reflecting the 'meat eaters' paradox'. Bison was perceived as a lean game meat, suggesting a lack of awareness of current bison production and retail availability. Horse meat was unfamiliar to 80% of the participants. Horse meat was acknowledged to be consumed in other regions, however as a companion animal and pet, the dominant perception of horse meat was that it was unacceptable for eating. Participants were clustered into four groups based on the combined food-related personality traits of variety seeking and food involvement. The high food involvement cluster associated bison with positive eating quality attributes and may be amenable to its consumption when provided with accurate information about bison production.

Fatty Acid Composition, Tocopherols, Volatile Compounds, and Sensory Evaluation of Low Morphine Yielding Varieties of Poppy (Papaver somniferum L.) Seeds and Oils.

Low morphine yielding winter ('Zeno Morphex') and summer ('Viola', 'Mieszko', 'Borowski') poppy varieties were investigated for their chemical composition and sensory properties. The oil content of the 13 seed samples as well as that of fatty acids, tocopherols, and volatile compounds in the respective oils were determined, and the sensory profiles of the seeds and oils were established. Linoleic acid made up 70.7-75.2% of the fatty acids. High amounts of γ-tocopherol were detected, especially in variety 'Viola' (287 ± 34 mg kg-1), while δ-tocopherol was only present in 'Zeno Morphex' (3.9 ± 0.6 mg kg-1). The most abundant volatiles were caproic acid (1.4-148 µg g-1), hexanal (0.9-15.2 µg g-1), 1-hexanol (0.3-20.1 µg g-1), limonene (1.3-9.4 µg g-1), and 2-pentylfuran (1.0-7.8 µg g-1). The sensory panel distinguished samples in particular by fatty/oily, rancid, sweet, and green attributes, the green aroma being correlated to three methoxypyrazines only present in summer poppies.

Effects of structural differences on the antibacterial activity of biflavonoids from fruits of the Brazilian peppertree (Schinus terebinthifolius Raddi).

Flavonoids, synthesized by plants across all families and therefore found in a huge variety, possess a diverse range of pharmacological properties. Direct antibacterial and synergistic activities as well as the inhibition of several bacterial virulence factors are known. Besides the mode of action, it is important to understand the structure-activity relationship to identify key structural characteristics. This study aimed to identify biflavonoids with antibacterial activity from Schinus terebinthifolius Raddi fruits. The purified biflavonoids were characterized in terms of their antibacterial effects. We found that the activity of biflavonoids, including agathisflavone (AGF), amentoflavone (AMF), and tetrahydroamentoflavone (THAF), was dependent on their chemical configuration and degree of oxidation, with THAF showing the highest activity on planktonic cells. Additionally, biofilm formation and composition were strongly influenced by THAF. Even slight differences in the chemical structure have fundamental effects on the activity of isolated biflavonoids. This suggests a specific binding of these substances in bacteria and thus enables detailed investigations of the mode of action in the future.

Enhancement of Biomimetic Enzymatic Mineralization of Gellan Gum Polysaccharide Hydrogels by Plant-Derived Gallotannins.

Mineralization of hydrogel biomaterials with calcium phosphate (CaP) is considered advantageous for bone regeneration. Mineralization can be both induced by the enzyme alkaline phosphatase (ALP) and promoted by calcium-binding biomolecules, such as plant-derived polyphenols. In this study, ALP-loaded gellan gum (GG) hydrogels were enriched with gallotannins, a subclass of polyphenols. Five preparations were compared, namely three tannic acids of differing molecular weight (MW), pentagalloyl glucose (PGG), and a gallotannin-rich extract from mango kernel (Mangifera indica L.). Certain gallotannin preparations promoted mineralization to a greater degree than others. The various gallotannin preparations bound differently to ALP and influenced the size of aggregates of ALP, which may be related to ability to promote mineralization. Human osteoblast-like Saos-2 cells grew in eluate from mineralized hydrogels. Gallotannin incorporation impeded cell growth on hydrogels and did not impart antibacterial activity. In conclusion, gallotannin incorporation aided mineralization but reduced cytocompatibility.

Differentiation of Brazilian Peppertree (Schinus terebinthifolius Raddi) and Peruvian Peppertree (Schinus molle L.) Fruits by UHPLC-UV-MS Analysis of Their Anthocyanin and Biflavonoid Profiles.

The objectives of this work were to determine the phenolic profile of Schinus terebinthifolius and Schinus molle fruits and to develop a reliable method for the differentiation of these two similar spices both known as pink pepper. Anthocyanins, biflavonoids and gallotannins, some of which are reported for the first time in these species, were identified by UHPLC-UV/vis-MS/MS. Consideration of the relative and absolute amounts of phenolics as well as indicator compounds from 18 samples revealed that the relative amounts of anthocyanins and biflavonoids are the most trustworthy parameters. Principal component analysis and cluster analysis (CA) allowed a grouping of the samples according to their species, showing that the anthocyanins are most important for the identification of species. As a result, authentication of the two Schinus species can be accomplished by UHPLC analysis of the relative amounts of anthocyanins combined with CA.

Pressurized liquid extraction of anthocyanins and biflavonoids from Schinus terebinthifolius Raddi: A multivariate optimization.

Response surface methodology was employed to investigate the effects of pressurized liquid extraction (PLE) parameters on the recovery of phenolic compounds (anthocyanins, biflavonoids) from Brazilian pepper (Schinus terebinthifolius Raddi) fruits. The effects of temperature, static time, and ethanol as well as acid concentration on the polyphenol yield were described well by quadratic models (p<0.0001). A significant influence of the ethanol concentration (p<0.0001) and several interactions (p<0.05) were identified. Identification of the biflavonoid I3',II8-binaringenin in drupes of S. terebinthifolius was achieved by UHPLC-MS(2). Interestingly, at high extraction temperatures (>75°C), an artifact occurred and was tentatively identified as a diastereomer of I3',II8-binaringenin. Multivariate optimization led to high yields of phenolic compounds from the exocarp/drupes at 100/75°C, 10/10min, 54.5/54.2% ethanol, and 5/0.03% acetic acid. This study demonstrates that PLE is well suited for the extraction of phenolic compounds from S. terebinthifolius and can efficiently be optimized by response surface methodology.

Characterization of phenolic compounds in Brazilian pepper (Schinus terebinthifolius Raddi) exocarp.

The objective of this study was to characterize the phenolic composition of Brazilian pepper (Schinus terebinthifolius Raddi) exocarp extract. Using UHPLC-DAD-MS/MS analysis, four anthocyanins, three biflavonoids, gallic acid, and two types of hydrolyzable tannins (galloyl glucoses, galloyl shikimic acids) were tentatively identified. The structure of the so far unknown 7-O-methylpelargonidin 3-O-ß-D-galactopyranoside was elucidated by 2D NMR. Within the group of gallotannins, galloyl shikimic acids with uncommon degrees of galloylation (tetra- to hexagalloyl shikimic acids) were detected. Among the biflavonoids, I3',II8-biapigenin (amentoflavone), I6,II8-biapigenin (agathisflavone), and II-2,3-dihydro-I3',II8-biapigenin were identified, which have already been described for Anacardiaceae. From the results of the present study together with previous findings on the phenolic profile of other Anacardiaceae plants, it is concluded that 7-methoxylated flavonoids are a chemotaxonomic trait frequently found in this family.