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The Journal of Physical Chemistry. A Feb 2022Carotenoids are conjugated linear molecules built from the repetition of terpene units, which display a large structural diversity in nature. They may, in particular,...
Carotenoids are conjugated linear molecules built from the repetition of terpene units, which display a large structural diversity in nature. They may, in particular, contain several types of side or end groups, which tune their functional properties, such as absorption position and photochemistry. We report here a detailed experimental study of the absorption and vibrational properties of allene-containing carotenoids, together with an extensive modeling of these experimental data. Our calculations can satisfactorily explain the electronic properties of vaucheriaxanthin, where the allene group introduces the equivalent of one C═C double bond into the conjugated C═C chain. The position of the electronic absorption of fucoxanthin and butanoyloxyfucoxanthin requires long-range corrections to be found correctly on the red side of that of vaucheriaxanthin; however, these corrections tend to overestimate the effect of the conjugated and nonconjugated C═O groups in these molecules. We show that the resonance Raman spectra of these carotenoids are largely perturbed by the presence of the allene group, with the two major Raman contributions split into two components. These perturbations are satisfactorily explained by modeling, through a gain in the Raman intensity of the C═C antisymmetric stretching mode, induced by the presence of the allene group in the carotenoid C═C chain.
Topics: Alkadienes; Carotenoids; Electronics; Spectrum Analysis, Raman
PubMed: 35114087
DOI: 10.1021/acs.jpca.1c09393 -
Nature Communications Jul 2021Aurantinins (ARTs) are antibacterial polyketides featuring a unique 6/7/8/5-fused tetracyclic ring system and a triene side chain with a carboxyl terminus. Here we...
Aurantinins (ARTs) are antibacterial polyketides featuring a unique 6/7/8/5-fused tetracyclic ring system and a triene side chain with a carboxyl terminus. Here we identify the art gene cluster and dissect ART's C-methyl incorporation patterns to study its biosynthesis. During this process, an apparently redundant methyltransferase Art28 was characterized as a malonyl-acyl carrier protein O-methyltransferase, which represents an unusual on-line methyl esterification initiation strategy for polyketide biosynthesis. The methyl ester bond introduced by Art28 is kept until the last step of ART biosynthesis, in which it is hydrolyzed by Art9 to convert inactive ART 9B to active ART B. The cryptic reactions catalyzed by Art28 and Art9 represent a protecting group biosynthetic logic to render the ART carboxyl terminus inert to unwanted side reactions and to protect producing organisms from toxic ART intermediates. Further analyses revealed a wide distribution of this initiation strategy for polyketide biosynthesis in various bacteria.
Topics: Acyl Carrier Protein; Anti-Bacterial Agents; Bacillus subtilis; Bacterial Proteins; Biosynthetic Pathways; Esterification; Gram-Negative Bacteria; Gram-Positive Bacteria; Methyltransferases; Microbial Sensitivity Tests; Models, Chemical; Molecular Structure; Multigene Family; Polyenes; Polyketides
PubMed: 34301953
DOI: 10.1038/s41467-021-24846-7 -
Biochimica Et Biophysica Acta Feb 2016The influence of flavonoids and polyene antibiotics on the permeability of membranes has been investigated through measurements of calcein leakage from large unilamellar...
The influence of flavonoids and polyene antibiotics on the permeability of membranes has been investigated through measurements of calcein leakage from large unilamellar vesicles composed of DOPC:cholesterol (67:33 mol%). Phloretin and biochanin A have been shown to induce calcein release from liposomes, but quercetin, daidzein, and catechin have not. Differential scanning calorimetry has indicated a decreasing of melting temperature of DPPC vesicles by 1.5-2°C in the presence of phloretin and biochanin A. Quercetin, catechin, and daidzein have had almost no effect on the main transition temperature. Phloretin, biochanin A, and quercetin have significantly broadened the main transition peak of DPPC. Phloretin have increased a leakage induced by polyene antibiotics, whereas catechin and daidzein have not. Quercetin has slightly affected it. The effects of tested flavonoids on the polyene-induced calcein leakage and channel forming activity have been similar. The obtained data agree with the previously supposed hypothesis regarding the enhancement of polyene activity by reducing elastic stress near the lipid mouth of the nystatin pore. The inhibition of polyene channel forming activity by biochanin A observed in planar DOPC:cholesterol bilayers may be related to the flavonoid competition with cholesterol in the polyene-sterol channel complexes.
Topics: Catechin; Cholesterol; Genistein; Membranes, Artificial; Phloretin; Phosphatidylcholines; Polyenes; Quercetin
PubMed: 26657529
DOI: 10.1016/j.bbamem.2015.12.004 -
Communications Biology Oct 2023Various species of ascomycete fungi synthesize the carboxylic carotenoid neurosporaxanthin. The unique chemical structure of this xanthophyll reveals that: (1) Its...
Various species of ascomycete fungi synthesize the carboxylic carotenoid neurosporaxanthin. The unique chemical structure of this xanthophyll reveals that: (1) Its carboxylic end and shorter length increase the polarity of neurosporaxanthin in comparison to other carotenoids, and (2) it contains an unsubstituted β-ionone ring, conferring the potential to form vitamin A. Previously, neurosporaxanthin production was optimized in Fusarium fujikuroi, which allowed us to characterize its antioxidant properties in in vitro assays. In this study, we assessed the bioavailability of neurosporaxanthin compared to other provitamin A carotenoids in mice and examined whether it can be cleaved by the two carotenoid-cleaving enzymes: β-carotene-oxygenase 1 (BCO1) and 2 (BCO2). Using Bco1Bco2 mice, we report that neurosporaxanthin displays greater bioavailability than β-carotene and β-cryptoxanthin, as evidenced by higher accumulation and decreased fecal elimination. Enzymatic assays with purified BCO1 and BCO2, together with feeding studies in wild-type, Bco1, Bco2, and Bco1Bco2 mice, revealed that neurosporaxanthin is a substrate for either carotenoid-cleaving enzyme. Wild-type mice fed neurosporaxanthin displayed comparable amounts of vitamin A to those fed β-carotene. Together, our study unveils neurosporaxanthin as a highly bioavailable fungal carotenoid with provitamin A activity, highlighting its potential as a novel food additive.
Topics: Mice; Animals; beta Carotene; Provitamins; Vitamin A; Biological Availability; Carotenoids; Dioxygenases
PubMed: 37864015
DOI: 10.1038/s42003-023-05446-1 -
The Journal of Nutrition Oct 2023Carotenoids are plant pigments with light filtering and antioxidant properties that deposit in human tissues, including retina and skin. Descriptive characteristics and...
BACKGROUND
Carotenoids are plant pigments with light filtering and antioxidant properties that deposit in human tissues, including retina and skin. Descriptive characteristics and covariates of carotenoid status in macula and skin have been examined in adults; however, similar studies in children are limited. Thus, this study aimed to delineate how factors of age, sex, race, weight status, and dietary carotenoid intake relate to macular and skin carotenoids in children.
METHODS
Children (7-13 y, N = 375) completed heterochromatic flicker photometry to assess macular pigment optical density (MPOD). Participants underwent anthropometrics to measure weight status (BMI percentile [BMI%]), and parent/guardian provided demographic information. Subsample data were available for skin carotenoids (N = 181), assessed using reflection spectroscopy, and dietary carotenoids (N = 101) using the Block Food Frequency Questionnaire. Relationships between skin and macular carotenoids were assessed using partial Pearson's correlations controlling for age, sex, race, and BMI%. Relationships between dietary carotenoids and macular and skin carotenoids were assessed using stepwise linear regression including age, sex, race, and BMI% in the model.
RESULTS
Mean MPOD was 0.56 ± 0.22 and skin carotenoid score was 282 ± 94.6. There was no significant correlation between MPOD and skin carotenoids (r = 0.02, P = 0.76). BMI% was negatively associated with skin (stdβ = -0.42, P < 0.001), but not macular carotenoids (stdβ = -0.04, P = 0.70). Neither MPOD nor skin carotenoids were associated with age, sex, or race (all P > 0.10). MPOD was positively associated with energy-adjusted reported lutein + zeaxanthin intake (stdβ = 0.27, P = 0.01). Skin carotenoids were positively associated with energy-adjusted reported carotenoid intake (stdβ = 0.26, P = 0.01).
CONCLUSIONS
The mean MPOD values in children were higher than what has been reported in adult populations. Previous studies in adult samples report an average MPOD of 0.21. Although macular and skin carotenoids were not related, they were associated with dietary carotenoids relevant to the respective tissues; however, skin carotenoids may be more susceptible negative influence from higher weight status.
Topics: Adult; Humans; Child; Macular Pigment; Lutein; Zeaxanthins; Macula Lutea; Retina
PubMed: 37315793
DOI: 10.1016/j.tjnut.2023.06.006 -
Journal of Alzheimer's Disease : JAD 2023Oxidative stress contributes to pathogenesis and progression of Alzheimer's disease (AD). Higher levels of the dietary antioxidants- carotenoids and tocopherols- are... (Review)
Review
BACKGROUND
Oxidative stress contributes to pathogenesis and progression of Alzheimer's disease (AD). Higher levels of the dietary antioxidants- carotenoids and tocopherols- are associated with better cognitive functions and lower risk for AD, and lower levels of multiple carotenoids are found in serum and plasma of patients with AD. Although brains donated by individuals with mild cognitive impairment had significantly lower levels of lutein and beta-carotene, previous investigators found no significant difference in carotenoid levels of brains with AD and cognitively normal brains.
OBJECTIVE
This study tested the hypothesis that micronutrients are significantly lower in donor brains with AD than in healthy elderly brains.
METHODS
Samples of donor brains with confirmed AD or verified health were dissected into grey and white matter, extracted with organic solvents and analyzed by HPLC.
RESULTS
AD brains had significantly lower levels of lutein, zeaxanthin, anhydrolutein, retinol, lycopene, and alpha-tocopherol, and significantly increased levels of XMiAD, an unidentified xanthophyll metabolite. No meso-zeaxanthin was detected. The overlapping protective roles of xanthophylls, carotenes, α- and γ-tocopherol are discussed.
CONCLUSION
Brains with AD had substantially lower concentrations of some, but not all, xanthophylls, carotenes, and tocopherols, and several-fold higher concentrations of an unidentified xanthophyll metabolite increased in AD (XMiAD).
Topics: Humans; Aged; Vitamin A; Tocopherols; Xanthophylls; Lycopene; Lutein; Alzheimer Disease; Zeaxanthins; White Matter; Carotenoids; Antioxidants; Brain
PubMed: 35988225
DOI: 10.3233/JAD-220460 -
BMC Cancer Apr 2021Triazole, polyene, and echinocandin antifungal agents are extensively used to treat invasive fungal infections (IFIs); however, the optimal prophylaxis option is not... (Meta-Analysis)
Meta-Analysis
BACKGROUND AND AIM
Triazole, polyene, and echinocandin antifungal agents are extensively used to treat invasive fungal infections (IFIs); however, the optimal prophylaxis option is not clear. This study aimed to determine the optimal agent against IFIs for patients with hematological malignancies.
METHODS
Randomized controlled trials (RCTs) comparing the effectiveness of triazole, polyene, and echinocandin antifungal agents with each other or placebo for IFIs in patients with hematological malignancies were searched. This Bayesian network meta-analysis was performed for all agents.
RESULTS
The network meta-analyses showed that all triazoles, amphotericin B, and caspofungin, but not micafungin, reduced IFIs. Posaconazole was superior to fluconazole [odds ratio (OR), 0.30; 95% credible interval (CrI), 0.12-0.60], itraconazole (OR, 0.40; 95% CrI, 0.15-0.85), and amphotericin B (OR, 4.97; 95% CrI, 1.73-11.35). It also reduced all-cause mortality compared with fluconazole (OR, 0.35; 95% CrI, 0.08-0.96) and itraconazole (OR, 0.33; 95% CrI, 0.07-0.94), and reduced the risk of adverse events compared with fluconazole (OR, 0.02; 95% CrI, 0.00-0.03), itraconazole (OR, 0.01; 95% CrI, 0.00-0.02), posaconazole (OR, 0.02; 95% CrI, 0.00-0.03), voriconazole (OR, 0.005; 95% CrI, 0.00 to 0.01), amphotericin B (OR, 0.004; 95% CrI, 0.00-0.01), and caspofungin (OR, 0.05; 95% CrI, 0.00-0.42) despite no significant difference in the need for empirical treatment and the proportion of successful treatment.
CONCLUSIONS
Posaconazole might be an optimal prophylaxis agent because it reduced IFIs, all-cause mortality, and adverse events, despite no difference in the need for empirical treatment and the proportion of successful treatment.
Topics: Antifungal Agents; Echinocandins; Hematologic Neoplasms; Humans; Invasive Fungal Infections; Network Meta-Analysis; Polyenes; Pre-Exposure Prophylaxis; Publication Bias; Treatment Outcome; Triazoles
PubMed: 33853560
DOI: 10.1186/s12885-021-07973-8 -
Nutrients Mar 2022Retinol binding protein 4 (RBP4) is the specific transport protein of the lipophilic vitamin A, retinol, in blood. Circulating RBP4 originates from the liver. It is... (Review)
Review
Retinol binding protein 4 (RBP4) is the specific transport protein of the lipophilic vitamin A, retinol, in blood. Circulating RBP4 originates from the liver. It is secreted by hepatocytes after it has been loaded with retinol and binding to transthyretin (TTR). TTR association prevents renal filtration due to the formation of a higher molecular weight complex. In the circulation, RBP4 binds to specific membrane receptors, thereby delivering retinol to target cells, rendering liver-secreted RBP4 the major mechanism to distribute hepatic vitamin A stores to extrahepatic tissues. In particular, binding of RBP4 to 'stimulated by retinoic acid 6' (STRA6) is required to balance tissue retinoid responses in a highly homeostatic manner. Consequently, defects/mutations in RBP4 can cause a variety of conditions and diseases due to dysregulated retinoid homeostasis and cover embryonic development, vision, metabolism, and cardiovascular diseases. Aside from the effects related to retinol transport, non-canonical functions of RBP4 have also been reported. In this review, we summarize the current knowledge on the regulation and function of RBP4 in health and disease derived from murine models and human mutations.
Topics: Animals; Homeostasis; Humans; Liver; Mice; Retinoids; Tretinoin; Vitamin A
PubMed: 35334893
DOI: 10.3390/nu14061236 -
International Journal of Molecular... Apr 2022Hance is a non-woody forest plant widely used in China, Korea, and Japan because of its various therapeutic properties. However, the genetic details of the carotenoid...
Identification, In Silico Characterization, and Differential Expression Profiles of Carotenoid, Xanthophyll, Apocarotenoid Biosynthetic Pathways Genes, and Analysis of Carotenoid and Xanthophyll Accumulation in Hance.
Hance is a non-woody forest plant widely used in China, Korea, and Japan because of its various therapeutic properties. However, the genetic details of the carotenoid pathway (CP), xanthophyll pathway (XP), and apocarotenoid pathway (AP) genes have not been studied. Thus, the CP, XP, and AP genes of were detected and analyzed. A total of fifteen genes were identified, of which eight, four, and three belonged to CP, XP, and AP, respectively. All identified genes possessed full open reading frames. Phylogenetic characterization of the identified gene sequences showed the highest similarity with other higher plants. Multiple alignments and 3D dimensional structures showed several diverse conserved motifs, such as the carotene-binding motif, dinucleotide-binding motif, and aspartate or glutamate residues. The results of real-time PCR showed that the CP, XP, and AP genes were highly expressed in leaves, followed by the stems and roots. In total, eight different individual carotenoids were identified using HPLC analysis. The highest individual and total carotenoid content were achieved in the leaves, followed by the stems and roots. This study will provide more information on the gene structure of the CP, XP, and AP genes, which may help to increase the accumulation of carotenoids in through genetic engineering. These results could be helpful for further molecular and functional studies of CP, XP, and AP genes.
Topics: Biosynthetic Pathways; Carotenoids; Gene Expression Regulation, Plant; Heracleum; Lutein; Phylogeny; Xanthophylls
PubMed: 35563233
DOI: 10.3390/ijms23094845 -
Journal of Materials Science. Materials... Nov 20233D printing technology is an emerging method that gained extensive attention from researchers worldwide, especially in the health and medical fields. Biopolymers are an... (Review)
Review
3D printing technology is an emerging method that gained extensive attention from researchers worldwide, especially in the health and medical fields. Biopolymers are an emerging class of materials offering excellent properties and flexibility for additive manufacturing. Biopolymers are widely used in biomedical applications in biosensing, immunotherapy, drug delivery, tissue engineering and regeneration, implants, and medical devices. Various biodegradable and non-biodegradable polymeric materials are considered as bio-ink for 3d printing. Here, we offer an extensive literature review on the current applications of synthetic biopolymers in the field of 3D printing. A trend in the publication of biopolymers in the last 10 years are focused on the review by analyzing more than 100 publications. Their application and classification based on biodegradability are discussed. The various studies, along with their practical applications, are elaborated in the subsequent sections for polyethylene, polypropylene, polycaprolactone, polylactide, etc. for biomedical applications. The disadvantages of various biopolymers are discussed, and future perspectives like combating biocompatibility problems using 3D printed biomaterials to build compatible prosthetics are also discussed and the potential application of using resin with the combination of biopolymers to build customized implants, personalized drug delivery systems and organ on a chip technologies are expected to open a new set of chances for the development of healthcare and regenerative medicine in the future.
Topics: Artificial Limbs; Biopolymers; Polyethylene; Polymers; Printing, Three-Dimensional; Polypropylenes
PubMed: 37982917
DOI: 10.1007/s10856-023-06765-9