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Angewandte Chemie (International Ed. in... Jan 2023A catalysis-based regioselective 1,4-fluorofunctionalization of trifluoromethyl substituted 1,3-dienes has been developed to access compact, highly functionalized...
A catalysis-based regioselective 1,4-fluorofunctionalization of trifluoromethyl substituted 1,3-dienes has been developed to access compact, highly functionalized products. The process allows E,Z-mixed dienes to be processed to a single E-alkene isomer, and leverages an inexpensive and operationally convenient I(I)/I(III) catalysis platform. The first example of catalytic 1,4-difluorination is disclosed and subsequently evolved to enable 1,4-hetero-difunctionalization, which allows δ-fluoro-alcohol and amine derivatives to be forged in a single operation. The protocol is compatible with a variety of nucleophiles including fluoride, nitriles, carboxylic acids, alcohols and even water thereby allowing highly functionalized products, with a stereocenter bearing both C(sp )-F and C(sp )-CF groups, to be generated rapidly. Scalability (up to 3 mmol), and facile post-reaction modifications are demonstrated to underscore the utility of the method in expanding organofluorine chemical space.
Topics: Polyenes; Isomerism; Alkenes; Catalysis; Alcohols
PubMed: 36345795
DOI: 10.1002/anie.202214906 -
Food Research International (Ottawa,... Mar 2021The aim of this study was the use and revalorization of two persimmon by-products A and B generated in the juice production process. The by-product B resulting from a...
The aim of this study was the use and revalorization of two persimmon by-products A and B generated in the juice production process. The by-product B resulting from a pectinase enzymatic treatment of peels and pulp to optimize juice extraction was especially suitable for recovery of valuable bioactive carotenoids. The extraction solvents and solvent combinations used were: ethanol, acetone, ethanol/acetone (50:50 v/v) and ethanol/acetone/hexane (25:25:50 v/v/v). HPLC-DAD analysis detected and identified a total of nine individual carotenoids namely violaxanthin, neoxanthin, antheraxanthin, lutein, zeaxanthin, β-cryptoxanthin 5,6-epoxide, β-cryptoxanthin, α-carotene, and β-carotene. β-cryptoxanthin and β-carotene represented 49.2% and 13.2% of the total carotenoid content (TCC) in the acetone extract from by-product B. TCC contributed greatly to antioxidant activity of acetone extract derived from this by-product. Pectinase enzymatic treatment of persimmon peels and pulp followed by absolute acetone extraction of carotenoids could be an efficient method to obtain a rich extract in these compounds that could be used as nutraceutical ingredient.
Topics: Carotenoids; Diospyros; Fruit; Lutein; Zeaxanthins
PubMed: 33641941
DOI: 10.1016/j.foodres.2020.109882 -
BMC Public Health Aug 2023Dietary carotenoids have been proven to improve intestinal disorders like inflammatory bowel disease and colon cancer, yet little is known about the link between dietary...
BACKGROUND
Dietary carotenoids have been proven to improve intestinal disorders like inflammatory bowel disease and colon cancer, yet little is known about the link between dietary carotenoids and constipation. This study aims to examine the relationship between dietary carotenoids intake and constipation, using data from the National Health and Nutrition Examination Survey (NHANES) 2005-2010.
METHODS
A total of 11,722 participants were enrolled. Chronic constipation was defined as type 1 (separate hard lumps, like nuts) and type 2 (sausage-like, but lumpy) in the Bristol stool form scale (BSFS). Carotenoids intake was obtained from the average of two 24-hour dietary recall questionnaires (if only one 24-hour was available, we used it) and divided into quartiles (Q). The prevalence of constipation was calculated across men and women individuals. The relationship between dietary carotenoids intake and constipation in men and women was assessed with weighted logistic regression and smoothed curve fitting after adjusting confounders, with results displayed as weighted odds ratio (OR) with 95% confidence intervals (95% CI). The model was further stratified by age, race, and HEI 2015 scores (with median as cutoff) among men and women.
RESULTS
The total weighted prevalence of chronic constipation in this study was 8.08%, 11.11% in women and 5.18% in men. After multivariable adjustment, compared with the lowest intake, participants with the highest dietary lycopene intake (OR 0.55, 95% CI: 0.36-0.84, p for trend = 0.01) and total lycopene intake (OR = 0.52, 95% CI: 0.34-0.80, p for trend = 0.01) were negatively associated with the risk of chronic constipation in men, whereas increased dietary α-carotene intake reduced the risk of chronic constipation in women (OR = 0.69, 95% CI: 0.48-0.98, p for trend = 0.04). Smoothing curve fitting further supported these results and provided evidence of dose-response effects. No association was found between other types of carotenoids and chronic constipation in men and women.
CONCLUSIONS
Increasing lycopene intake may improve bowel function in men while increased α-carotene intake may reduce the risk of chronic constipation in women. Further studies are essential to explore the role that the intake of carotenoids plays in chronic constipation.
Topics: Male; Adult; Female; Humans; Lycopene; Cross-Sectional Studies; Nutrition Surveys; Carotenoids; Constipation
PubMed: 37608273
DOI: 10.1186/s12889-023-16367-3 -
Journal of the American Heart... Feb 2023Background Systemic oxidative stress is involved in the development of hypertension, whereas carotenoids are a group of natural antioxidants. Our study aims to evaluate...
Background Systemic oxidative stress is involved in the development of hypertension, whereas carotenoids are a group of natural antioxidants. Our study aims to evaluate the relationships between the serum concentrations of major carotenoids and mortality in hypertensive adults. Methods and Results Data on 5 serum carotenoids from the National Health and Nutrition Examination Survey (NHANES) III and NHANES 2001-2006 were included. Outcome measures (all-cause and cardiovascular mortality) were identified from the National Death Index through December 31, 2019. Multiple Cox proportional hazards regression and restricted cubic spline analyses were performed to determine the association between carotenoid levels and outcomes. A total of 8390 hypertensive adults were included in the analysis. At a median follow-up duration of 16.6 years, all-cause and cardiovascular mortality occurred in 4005 (47.74%) and 1205 (14.36%) participants, respectively. Compared with the lowest quartiles, the highest quartiles of 5 major serum carotenoids were associated with lower risk of all-cause mortality, with multivariable-adjusted hazard ratios (HRs) of 0.63 (95% CI, 0.56-0.71) for α-carotene, 0.70 (95% CI, 0.61-0.80); for β-carotene, 0.67 (95% CI, 0.58-0.76); for β-cryptoxanthin, 0.74 (95% CI, 0.64-0.86) for lycopene; and 0.72 (95% CI, 0.63-0.83) for lutein/zeaxanthin. For cause-specific mortality, this association with the fourth quartile of serum carotenoids was evident for a reduced rate of cardiovascular mortality, with a 32% reduction for α-carotene (HR, 0.68 [95% CI, 0.55-0.86]), a 29% reduction for β-cryptoxanthin (HR, 0.71 [95% CI, 0.56-0.89]), and a 26% reduction for lycopene (HR, 0.74 [95% CI, 0.59-0.94]), but not for β-carotene and lutein/zeaxanthin. In addition, we found that serum α-carotene, β-carotene, β-cryptoxanthin, and lutein/zeaxanthin levels were nonlinearly related to all-cause mortality with inflection points of 2.43, 8.49, 5.12, and 14.17 μg/dL, respectively. Serum α-carotene, β-cryptoxanthin, and lutein/zeaxanthin concentrations showed nonlinear associations with cardiovascular mortality with inflection points of 2.31, 5.26, and 15.40 μg/dL, respectively. Conclusions Findings suggest that higher serum carotenoid concentrations were associated with lower risks of all-cause and cardiovascular mortality in hypertensive adults.
Topics: Adult; Humans; Lycopene; beta Carotene; Lutein; Nutrition Surveys; Zeaxanthins; Xanthophylls; Beta-Cryptoxanthin; Carotenoids; Hypertension
PubMed: 36752230
DOI: 10.1161/JAHA.122.027568 -
International Journal of Molecular... Nov 2022are of great interest in the pharmaceutical industry as they produce a plethora of secondary metabolites that act as antibacterial and antifungal agents. They may... (Review)
Review
are of great interest in the pharmaceutical industry as they produce a plethora of secondary metabolites that act as antibacterial and antifungal agents. They may thrive on their own in the soil, or associate with other organisms, such as plants or invertebrates. Some soil-derived strains exhibit hemolytic properties when cultivated on blood agar, raising the question of whether hemolysis could be a virulence factor of the bacteria. In this work we examined hemolytic compound production in 23 β-hemolytic isolates; of these 12 were soil-derived, 10 were arthropod-associated, and 1 was plant-associated. An additional human-associated sp. TR1341 served as a control. Mass spectrometry analysis suggested synthesis of polyene molecules responsible for the hemolysis: candicidins, filipins, strevertene A, tetrafungin, and tetrin A, as well as four novel polyene compounds (denoted here as polyene A, B, C, and D) in individual liquid cultures or paired co-cultures. The non-polyene antifungal compounds actiphenol and surugamide A were also identified. The findings indicate that the ability of to produce cytolytic compounds (here manifested by hemolysis on blood agar) is an intrinsic feature of the bacteria in the soil environment and could even serve as a virulence factor when colonizing available host organisms. Additionally, a literature review of polyenes and non-polyene hemolytic metabolites produced by is presented.
Topics: Humans; Streptomyces; Antifungal Agents; Anti-Bacterial Agents; Polyenes; Hemolysis; Virulence Factors
PubMed: 36499372
DOI: 10.3390/ijms232315045 -
Nutrients Mar 2022Vitamin A is an essential nutrient required throughout life. Through its various metabolites, vitamin A sustains fetal development, immunity, vision, and the... (Review)
Review
Vitamin A is an essential nutrient required throughout life. Through its various metabolites, vitamin A sustains fetal development, immunity, vision, and the maintenance, regulation, and repair of adult tissues. Abnormal tissue levels of the vitamin A metabolite, retinoic acid, can result in detrimental effects which can include congenital defects, immune deficiencies, proliferative defects, and toxicity. For this reason, intricate feedback mechanisms have evolved to allow tissues to generate appropriate levels of active retinoid metabolites despite variations in the level and format, or in the absorption and conversion efficiency of dietary vitamin A precursors. Here, we review basic mechanisms that govern vitamin A signaling and metabolism, and we focus on retinoic acid-controlled feedback mechanisms that contribute to vitamin A homeostasis. Several approaches to investigate mechanistic details of the vitamin A homeostatic regulation using genomic, gene editing, and chromatin capture technologies are also discussed.
Topics: Feedback; Lipid Metabolism; Retinoids; Tretinoin; Vitamin A
PubMed: 35334970
DOI: 10.3390/nu14061312 -
Communications Biology Feb 2023This Perspective discusses how retinol catalyzes resonance energy transfer (RET) reactions pivotally important for mitochondrial energy homeostasis by protein kinase C... (Review)
Review
This Perspective discusses how retinol catalyzes resonance energy transfer (RET) reactions pivotally important for mitochondrial energy homeostasis by protein kinase C δ (PKCδ). PKCδ signals to the pyruvate dehydrogenase complex, controlling oxidative phosphorylation. The PKCδ-retinol complex reversibly responds to the redox potential of cytochrome c, that changes with the electron transfer chain workload. In contrast, the natural retinoid anhydroretinol irreversibly activates PKCδ. Its elongated conjugated-double-bond system limits the energy quantum absorbed by RET. Consequently, while capable of triggering the exergonic activating pathway, anhydroretinol fails to activate the endergonic silencing path, trapping PKCδ in the ON position and causing harmful levels of reactive oxygen species. However, physiological retinol levels displace anhydroretinol, buffer cyotoxicity and potentially render anhydroretinol useful for rapid energy generation. Intriguingly, apocarotenoids, the primary products of the mitochondrial β-carotene,9'-10'-oxygenase, have all the anhydroretinol-like features, including modulation of energy homeostasis. We predict significant conceptual advances to stem from further understanding of the retinoid-catalyzed RET.
Topics: Retinoids; Vitamin A; beta Carotene; Biology
PubMed: 36854887
DOI: 10.1038/s42003-023-04602-x -
Nutrients Mar 2022Vitamin A (VA), all-trans-retinol (ROL), and its analogs are collectively called retinoids. Acting through the retinoic acid receptors RARα, RARβ, and RARγ,... (Review)
Review
Vitamin A (VA), all-trans-retinol (ROL), and its analogs are collectively called retinoids. Acting through the retinoic acid receptors RARα, RARβ, and RARγ, all-trans-retinoic acid, an active metabolite of VA, is a potent regulator of numerous biological pathways, including embryonic and somatic cellular differentiation, immune functions, and energy metabolism. The liver is the primary organ for retinoid storage and metabolism in humans. For reasons that remain incompletely understood, a body of evidence shows that reductions in liver retinoids, aberrant retinoid metabolism, and reductions in RAR signaling are implicated in numerous diseases of the liver, including hepatocellular carcinoma, non-alcohol-associated fatty liver diseases, and alcohol-associated liver diseases. Conversely, restoration of retinoid signaling, pharmacological treatments with natural and synthetic retinoids, and newer agonists for specific RARs show promising benefits for treatment of a number of these liver diseases. Here we provide a comprehensive review of the literature demonstrating a role for retinoids in limiting the pathogenesis of these diseases and in the treatment of liver diseases.
Topics: Humans; Liver Diseases; Receptors, Retinoic Acid; Retinoids; Tretinoin; Vitamin A
PubMed: 35406069
DOI: 10.3390/nu14071456 -
Molecules (Basel, Switzerland) Dec 2022Carotenoid compounds are ubiquitous in nature, providing the characteristic colouring of many algae, bacteria, fruits and vegetables. They are a critical component of... (Review)
Review
Carotenoid compounds are ubiquitous in nature, providing the characteristic colouring of many algae, bacteria, fruits and vegetables. They are a critical component of the human diet and play a key role in human nutrition, health and disease. Therefore, the clinical importance of qualitative and quantitative carotene content analysis is increasingly recognised. In this review, the structural and optical properties of carotenoid compounds are reviewed, differentiating between those of carotenes and xanthophylls. The strong non-resonant and resonant Raman spectroscopic signatures of carotenoids are described, and advances in the use of Raman spectroscopy to identify carotenoids in biological environments are reviewed. Focus is drawn to applications in nutritional analysis, optometry and serology, based on in vitro and ex vivo measurements in skin, retina and blood, and progress towards establishing the technique in a clinical environment, as well as challenges and future perspectives, are explored.
Topics: Humans; Lutein; Spectrum Analysis, Raman; beta Carotene; Carotenoids; Xanthophylls; Zeaxanthins
PubMed: 36558154
DOI: 10.3390/molecules27249017 -
Molecules (Basel, Switzerland) Aug 2020Boron and silicon-substituted 1,3-dienes and boron and silicon-substituted alkenes and alkynes have been known for years and the last 10 years have seen a number of new... (Review)
Review
Boron and silicon-substituted 1,3-dienes and boron and silicon-substituted alkenes and alkynes have been known for years and the last 10 years have seen a number of new reports of their preparation and use in Diels-Alder reactions. This review first covers boron-substituted dienes and dienophiles and then moves on to discuss silicon-substituted dienes and dienophiles.
Topics: Alkynes; Boron; Catalysis; Cycloaddition Reaction; Models, Molecular; Polyenes; Silicon; Stereoisomerism
PubMed: 32824327
DOI: 10.3390/molecules25163740