Amino- and polyaminophthalazin-1(2H)-ones : synthesis, coordination properties, and biological activity

Amino- and polyaminophthalazinones were synthesized by the palladium‐catalyzed amination (alkyl- and arylamines, polyamines) of 4-bromophthalazinones in good yields. The coordinating properties of selected aminophthalazinones towards Cu(II) ions were investigated and the participation of the nitrogen atoms in the complexation of the metal ion was shown. A biological screening of the potential cytotoxicity of selected synthesized compounds on HT-29 and PC-3 cell lines, as well as on the L-929 cell line, proved that some amino derivatives of phthalazinone show interesting anticancer activities. The detailed synthesis, spectroscopic data, and biological assays are reported

A Mass Spectrometry-Based Approach for Characterization of Red, Blue, and Purple Natural Dyes

Effective analytical approaches for the identification of natural dyes in historical textiles are mainly based on high-performance liquid chromatography coupled with spectrophotometric detection and tandem mass spectrometric detection with electrospray ionization (HPLC-UV-Vis-ESI MS/MS). Due to the wide variety of dyes, the developed method should include an adequate number of reference color compounds, but not all of them are commercially available. Thus, the present study was focused on extending of the universal analytical HPLC-UV-Vis-ESI MS/MS approach to commercially unavailable markers of red, purple, and blue dyes. In the present study, HPLC-UV-Vis-ESI MS/MS was used to characterize the colorants in ten natural dyes (American cochineal, brazilwood, indigo, kermes, lac dye, logwood, madder, orchil, Polish cochineal, and sandalwood) and, hence, to extend the analytical method for the identification of natural dyes used in historical objects to new compounds. Dye markers were identified mostly on the basis of triple quadrupole MS/MS spectra. In consequence, the HPLC-UV-Vis-ESI MS/MS method with dynamic multiple reaction monitoring (dMRM) was extended to the next 49 commercially unavailable colorants (anthraquinones and flavonoids) in negative ion mode and to 11 (indigoids and orceins) in positive ion mode. These include protosappanin B, protosappanin E, erythrolaccin, deoxyerythrolaccin, nordamnacanthal, lucidin, santalin A, santalin B, santarubin A, and many others. Moreover, high-resolution QToF MS data led to the establishment of the complex fragmentation pathways of α-, β-, and γ- aminoorceins, hydroxyorceins, and aminoorceinimines extracted from wool dyed with Roccella tinctoria DC. The developed approach has been tested in the identification of natural dyes used in 223 red, purple, and blue fibers from 15th- to 17th-century silk textiles. These European and Near Eastern textiles have been used in vestments from the collections of twenty Krakow churches

Dietary Isorhamnetin Intake Is Inversely Associated with Coronary Artery Disease Occurrence in Polish Adults

The role of antioxidative agents in coronary artery disease (CAD) has been investigated, but the analysis of specific flavonols intake in Polish adults requires validated tools. The aim of this study was to estimate the dietary intake of flavonols in CAD patients by creating a food frequency questionnaire (FFQ) dedicated for this purpose in Polish adults. The FFQ included 140 products from 12 food groups. The study involved 103 adult respondents (43 CAD patients and 60 healthy controls). Mean daily intakes of total flavonols, quercetin, kaempferol, myricetin and isorhamnetin were calculated as absolute values and quartiles. Mean daily intakes of 12 main food categories and 27 subcategories were calculated as portions and quartiles. The validity test revealed high correlation for total flavonols, kaempferol, myricetin and isorhamnetin and moderate for quercetin. In the reproducibility analysis, the correlation was high for total flavonols, quercetin, kaempferol and myricetin, moderate for isorhamnetin and high for all 12 categories and 25 out of 27 subcategories of the tested food groups. The application of the FFQ in healthy adults and CAD patients revealed that dietary intakes of total flavonols and proportional intakes of kaempferol and isorhamnetin in Polish adults and CAD patients are higher than in most other European countries, while the proportional intakes of quercetin and myricetin are lower than in most European countries. The comparison between CAD patients and the healthy controls revealed significant differences in dietary isorhamnetin intake (p = 0.002). The results suggest that dietary isorhamnetin could have a potential role in CAD prevention

The Impact of Flavonols on Cardiovascular Risk

Cardiovascular disease (CVD) is the leading cause of deaths globally. The main target for prevention of cardiovascular (CV) risk are lifestyle changes, including particular dietary recommendations, involving high intake of fruits and vegetables. Flavonols are a subgroup of flavonoids—compounds present in fruits, vegetables, and tea—known for their antioxidative properties. There are many findings about the beneficial impact of flavonols on general CV risk and its factors, but mainly from in vitro and animal model studies. This paper summarizes data from human studies about flavonols’ impact on general CV risk and its factors. A high dietary intake of flavonols could decrease CVD mortality directly or through impact on selected CV factors; however, available data are inconsistent. Nonetheless, specific groups of patients (smoking men, hypertensive and diabetic patients) can potentially benefit from selected dietary modifications or flavonols (quercetin) supplementation. Future investigations about kaempferol and myricetin are needed

LC–Q–TOF–MS/MS Identification of Specific Non-Meat Proteins and Peptides in Beef Burgers

Beef burgers are a popular food choice, due to their taste and convenience. The extensive range of beef burgers with different flavours currently offered on the market is adding to their growing consumption. This study detected and identified specific non-meat proteins and peptide markers originating from functional preparations, i.e., powdered mixes of protein additives and spices, used as meat substitutes in the production of ready-to-cook beef burgers. Twenty-eight soy proteins, including isoforms (nine milk-, three pea- and one beetroot-specific protein) were found concurrently with a set of peptide markers unique to soy glycinin and β-conglycinin, pea vicilin and provicilin, milk αS1-casein, β-lactoglobulin, as well as beetroot elongation factor 2. Soy and beetroot proteins and peptides were observed in all burgers containing additives. Milk and pea proteins were included in powdered mixes but were not detected in burgers, indicating that their content was below the limit of detection. The study demonstrates that the proposed method can be implemented to analyse protein additives in cooked burgers; however, the presence of low amounts of additives, below 1⁻2%, should be further confirmed by using a more sensitive triple quadrupole instrument

Dietary Isorhamnetin Intake Is Associated with Lower Blood Pressure in Coronary Artery Disease Patients

Background: Recent studies suggest the positive role of flavonols on blood pressure (BP) values, although there are not many conducted on humans. The aim of this study was to examine the relationship between flavonol intake and their main sources of consumption, and systolic (SBP) and diastolic (DBP) BP values in coronary artery disease (CAD) patients. Methods and results: forty CAD patients completed a food-frequency questionnaire dedicated to flavonol-intake assessment. The analysis revealed significant correlation between isorhamnetin intake and SBP values—absolute (R: −0.36; 95% CI: −0.602 to −0.052; p = 0.02), and related to body mass (R: −0.38; 95% CI: −0.617 to −0.076; p = 0.02. This effect was observed in male participants (R: −0.65; 95% CI: −0.844 to −0.302; p = 0.001 and R: −0.63; 95% CI: −0.837 to −0.280; p = 0.002 respectively), but not in female patients. The main contributors were onions, tomatoes, blueberries, apples, tea, coffee and wine. White onion (R: −0.39; 95% CI: −0.624 to −0.088; p = 0.01) consumption was inversely correlated with SBP, and tomato consumption (R: −0.33; 95% CI: −0.581 to −0.020; p = 0.04) with DBP. The comparison between patients with BP < 140 mmHg and ≥140 mmHg revealed significant differences in white onion (p = 0.01) and blueberry (p = 0.04) intake. Conclusions: This study revealed the relationship between long-term dietary isorhamnetin intake and SBP values. The analysis of specific food intake showed that onion, tomato and blueberry consumption could impact BP values. This may suggest that a dietary approach which includes a higher intake of isorhamnetin-rich products could possibly result in BP lowering in CAD patients

Optimization of the Zebrafish Larvae Pentylenetetrazol-Induced Seizure Model for the Study of Caffeine and Topiramate Interactions

Epilepsy is a common neurological disorder characterized by seizures that cause neurobiological and behavioral impairment. Caffeine (CAF), which is the most widely consumed stimulant in the world, is reported to influence epileptic seizures and antiepileptic drugs, especially topiramate (TPM). The aim of the study was to optimize the zebrafish larvae pentylenetetrazol-induced seizure model for the study of CAF and TPM interactions, which include the determination of dose space, and the delivery of an analytical method for monitoring CAF, TPM, and CAF metabolite paraxanthine (PAR) in Zebrafish larvae. Methods: The zebrafish larvae, 4 days post-fertilization, were incubated for 18 h with CAF, TPM, or CAF + TPM, with subsequent locomotor activity assessment. Seizures were evoked by adding PTZ solution to obtain a final concentration of 20 mM. Subsequently, the liquid chromatography–mass spectrometry (LC–MS/MS) analytical method was used to simultaneously assess the levels of both CAF and TPM in the larvae. CAF (50 mg/L) and TPM (75 μM) given separately decreased the average larvae locomotor activity compared to the PTZ group but, however, were not able to lower it to the control level. Co-administration of 25 mg/L CAF and 50 μM TPM suppressed the activity to the same level. Adding 25 μM TPM to 50 mg/L CAF decrease the measured CAF level in the larvae. Until proven otherwise, CAF consumption should be regarded as a potential determinant in the modulation of TPM’s efficacy in the management of epileptic seizures. The optimized model will contribute to the standardization of studying CAF and TPM interactions and building the understanding of the molecular bases of the interaction

Effects of Physical and Chemical Factors on the Structure of Gluten, Gliadins and Glutenins as Studied with Spectroscopic Methods

This review presents applications of spectroscopic methods, infrared and Raman spectroscopies in the studies of the structure of gluten network and gluten proteins (gliadins and glutenins). Both methods provide complimentary information on the secondary and tertiary structure of the proteins including analysis of amide I and III bands, conformation of disulphide bridges, behaviour of tyrosine and tryptophan residues, and water populations. Changes in the gluten structure can be studied as an effect of dough mixing in different conditions (e.g., hydration level, temperature), dough freezing and frozen storage as well as addition of different compounds to the dough (e.g., dough improvers, dietary fibre preparations, polysaccharides and polyphenols). Additionally, effect of above mentioned factors can be determined in a common wheat dough, model dough (prepared from reconstituted flour containing only wheat starch and wheat gluten), gluten dough (lack of starch), and in gliadins and glutenins. The samples were studied in the hydrated state, in the form of powder, film or in solution. Analysis of the studies presented in this review indicates that an adequate amount of water is a critical factor affecting gluten structure

Reactions of 3-Hydroxy-2-phenyl-1H-benzo[e]isoindol-1-one: A Route to 3-Hydroxy-/3-anilinobenzo[e]indan-1-ones and Benzo[f]phthalazin-1(2H)-ones

New hydroxy- and anilinoindanone derivatives 3 and 4 were synthesized starting from 3-hydroxybenzo[e]isoindolinone 1 via the addition of alkyllithium (s-BuLi, n-BuLi, MeLi or i-PrLi) to the carbonyl group, followed by lactam ring opening and, finally, an intramolecular cyclization leading to target compounds. The same starting material was used for the preparation of the new benzo[f]phthalazinone derivatives 12–16 through multi-step reactions. The target derivative 16 was obtained from the corresponding bromolactam 15 by the Buchwald–Hartwig amination. Structures of the obtained compounds were confirmed by the NMR spectra

Wheat Bread Supplemented with <i>Agaricus bisporus</i> Powder: Effect on Bioactive Substances Content and Technological Quality

Supplementation of food products with mushroom powder increases their health-promoting value, but at the same time affects technological quality, which often play a key role for consumers. The aim of the research was to determine the effect of adding freeze-dried white and brown button mushrooms (2.5% and 5%) to wheat bread on its health-promoting properties such as antioxidant activity (DPPH, FRAP), total polyphenols and vitamin D2 content and as well as the technological quality as colour and texture. The breads were supplemented with mushroom lyophilisates, which were exposed to UVB radiation in order to increase their vitamin D2 content. The content of total polyphenols and antioxidant properties were determined spectrophotometrically, and the content of vitamin D2 by ultra-high performance liquid chromatography coupled to triple quadrupole spectrometer (UHPLC/MS/MS analysis). Colour parameters were determined in the CIE-Lab system and texture profile analysis (TPA) and sensory evaluation of the baked products were performed. The addition of dried mushrooms significantly increased the content of bioactive compounds (total polyphenols, vitamin D2) and the antioxidant properties of bread. A small addition of mushrooms caused a significant change in the basic technological quality of breads (colour parameters, specific volume, hardness, cohesiveness, springiness). At the same time, supplementation with mushroom lyophilisates has a positive effect on most analysed attributes in the nine-point hedonic scale. Based on the conducted research, it can be concluded that mushroom lyophilisates can be a valuable raw material for the fortification of bread, which is a good matrix and carrier of substances with documented biological activities