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Journal of the American Chemical Society Mar 2018A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good...
A sulfenium-ion-initiated, catalytic, enantioselective polyene cyclization is described. Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields. The thioether moiety resulting from the reaction can be subsequently transformed into diverse oxygen and carbon functionality postcyclization. The utility of this method is demonstrated by the enantioselective syntheses of (+)-ferruginol and (+)-hinokiol.
Topics: Abietanes; Catalysis; Cyclization; Lewis Bases; Molecular Structure; Polyenes; Stereoisomerism
PubMed: 29509003
DOI: 10.1021/jacs.8b01660 -
Nutrients Mar 2022Urological cancers, namely prostate, bladder, kidney, testicular, and penile cancers, are common conditions that constitute almost one-quarter of all malignant diseases... (Review)
Review
Urological cancers, namely prostate, bladder, kidney, testicular, and penile cancers, are common conditions that constitute almost one-quarter of all malignant diseases in men. Urological cancers tend to affect older individuals, and their development is influenced by modifiable metabolic, behavioral, and environmental risk factors. Phytochemicals may have cancer-fighting properties and protect against cancer development, slow its spread, and reduce the risk of cancer deaths in humans. This paper aims to review the current literature in regard to the effects of carotenoids in reducing urological cancer risk.
Topics: Anticarcinogenic Agents; Carotenoids; Diet; Humans; Lutein; Male; Urologic Neoplasms; Zeaxanthins; beta Carotene
PubMed: 35405980
DOI: 10.3390/nu14071367 -
Nutrition Journal Dec 2023To investigate the relationship between dietary carotenoid intake and sleep duration.
OBJECTIVE
To investigate the relationship between dietary carotenoid intake and sleep duration.
METHODS
Adults enrolled in the National Health and Nutrition Examination Survey (NHANES) 2007-2018 without missing information on dietary carotenoid intake (α-carotene, β-carotene, β-cryptoxanthin, lycopene, and lutein + zeaxanthin), sleep duration, and covariates were included. Participants' carotenoid consumption was divided into three groups by quartiles and sleep duration was grouped as short (< 7 h/night), optimal (7-8 h/night), and long (> 8 h/night). Multinominal logistic regression was constructed to examine the association between dietary carotenoid intake and sleep duration. Restricted cubic spline (RCS) regression was further utilized to explore their dose-response relationship. The weighted quantile sum (WQS) model was adopted to calculate the mixed and individual effect of 5 carotenoid sub-types on sleep duration.
RESULTS
Multinominal logistic regression presented that people with higher intakes of α-carotene, β-carotene, β-cryptoxanthin, lycopene, and lutein + zeaxanthin were less likely to sleep too short or too long. Consistent with the findings from multinominal logistic regression, the RCS models suggested a reverse U-shaped relationship between sleep duration and carotenoid intakes. The mixed effects were also significant, where β-cryptoxanthin and lutein + zeaxanthin were the top 2 contributors associated with the decreased risks of short sleep duration, while β-carotene, α-carotene, and β-cryptoxanthin were the main factors related to the lower risk of long sleep duration.
CONCLUSION
Our study revealed that the American adults with optimal sleep duration were associated with more dietary carotenoid intake, in comparison to short or long sleepers.
Topics: Adult; Humans; United States; Lycopene; beta Carotene; Nutrition Surveys; Lutein; Zeaxanthins; Beta-Cryptoxanthin; Sleep Duration; Carotenoids; Diet
PubMed: 38062512
DOI: 10.1186/s12937-023-00898-x -
Nutrition Reviews Apr 2021There is uncertainty regarding carotenoid intake recommendations, because positive and negative health effects have been found or are correlated with carotenoid intake... (Review)
Review
There is uncertainty regarding carotenoid intake recommendations, because positive and negative health effects have been found or are correlated with carotenoid intake and tissue levels (including blood, adipose tissue, and the macula), depending on the type of study (epidemiological vs intervention), the dose (physiological vs supraphysiological) and the matrix (foods vs supplements, isolated or used in combination). All these factors, combined with interindividual response variations (eg, depending on age, sex, disease state, genetic makeup), make the relationship between carotenoid intake and their blood/tissue concentrations often unclear and highly variable. Although blood total carotenoid concentrations <1000 nmol/L have been related to increased chronic disease risk, no dietary reference intakes (DRIs) exist. Although high total plasma/serum carotenoid concentrations of up to 7500 nmol/L are achievable after supplementation, a plateauing effect for higher doses and prolonged intake is apparent. In this review and position paper, the current knowledge on carotenoids in serum/plasma and tissues and their relationship to dietary intake and health status is summarized with the aim of proposing suggestions for a "normal," safe, and desirable range of concentrations that presumably are beneficial for health. Existing recommendations are likewise evaluated and practical dietary suggestions are included.
Topics: Carotenoids; Diet; Eating; Female; Humans; Lycopene; Male; Recommended Dietary Allowances; beta Carotene
PubMed: 32766681
DOI: 10.1093/nutrit/nuaa008 -
Nutrients Dec 2022Lycopene is a lipophilic unsaturated carotenoid exhibiting a strong singlet oxygen-quenching ability. Herein, we investigated the effect of lycopene intake on the... (Meta-Analysis)
Meta-Analysis Review
Lycopene is a lipophilic unsaturated carotenoid exhibiting a strong singlet oxygen-quenching ability. Herein, we investigated the effect of lycopene intake on the fasting blood glucose (FBG) level by conducting a systematic review and meta-analyses. We searched 15 databases (from the earliest date to June 2022 for PubMed or to August or September 2018 for the other databases) and included human interventional studies that assessed the effects of oral lycopene intake on FBG levels of participants ≥ 18 years of age. Three authors independently selected applicable studies and then assessed the study quality. Data were pooled as standardized mean difference (SMD) and analyzed by the random-effects model. Heterogeneity was assessed by I statistics. A meta-analysis including 11 trial arms ( = 750) revealed a tendency towards a significant decrease in FBG level with not-important heterogeneity [SMD = -0.15 (95% CI: -0.31, 0.00), = 0.05, I = 9%]. Subgroup meta-analysis including two studies ( = 152) in type 2 diabetes patients revealed significantly decreased FBG levels with not-important heterogeneity [SMD = -0.37 (95% CI: -0.69, -0.05), = 0.02, I = 0%]. Most studies meeting the eligibility criteria had a moderate risk of bias. The funnel plot for FBG suggested an absence of publication bias. In conclusion, this systematic review and meta-analyses suggested that lycopene intake exerted an FBG-decreasing effect.
Topics: Humans; Lycopene; Blood Glucose; Diabetes Mellitus, Type 2; Carotenoids; Fasting
PubMed: 36615780
DOI: 10.3390/nu15010122 -
Nutrients Oct 2022: Age-related macular degeneration (AMD) is a neurodegenerative ophthalmic disease. The purpose of this systematic review (SR) and meta-analysis was to evaluate if... (Meta-Analysis)
Meta-Analysis Review
: Age-related macular degeneration (AMD) is a neurodegenerative ophthalmic disease. The purpose of this systematic review (SR) and meta-analysis was to evaluate if dietary supplementation alone or in combinations might delay the progression of any of the stages of AMD. A SR and meta-analysis identifying cohort studies and randomized controlled trials (RCTs) evaluating the effect of supplements in patients diagnosed with AMD. PubMed, Scopus, Web of Science, CINAHL, and Cochrane were searched through 8th October 2021. Twenty studies, examining 5634 participants ranging from 55 to 80 years, were included in the SR. Eight studies were selected for meta-analysis (414 and 216 subjects in the intervention and control groups). Lutein and zeaxanthin plus -3 long-chain polyunsaturated fatty acids (-3 LC-PUFA) supplementation showed significant improvements in best-corrected visual acuity (BCVA) (SMD: -1.99, 95% CI: -3.33, -0.65) compared to the control group. Multifocal electroretinogram results (mfERG) were significantly improved overall (SMD: 4.59, 95% CI: 1.75, 7.43) after lutein plus zeaxanthin supplementation. Combinations of lutein and zeaxanthin with -3 LC-PUFA might be beneficial in preventing AMD progression and deterioration of visual function. Our results encourage initiating further studies with combinations of -3 LC-PUFA, lutein, and zeaxanthin especially in early AMD patients.
Topics: Humans; Zeaxanthins; Lutein; Xanthophylls; Visual Acuity; Double-Blind Method; Macular Degeneration; Dietary Supplements; Fatty Acids, Omega-3
PubMed: 36296956
DOI: 10.3390/nu14204273 -
Nutrients Nov 2022Owing to its unique structure and properties, fucoxanthin (FX), a carotenoid, has attracted significant attention. There have been numerous studies that demonstrate FX's... (Review)
Review
Owing to its unique structure and properties, fucoxanthin (FX), a carotenoid, has attracted significant attention. There have been numerous studies that demonstrate FX's anti-inflammatory, antioxidant, antitumor, and anti-obesity properties against inflammation-related diseases. There is no consensus, however, regarding the molecular mechanisms underlying this phenomenon. In this review, we summarize the potential health benefits of FX in inflammatory-related diseases, from the perspective of animal and cellular experiments, to provide insights for future research on FX. Previous work in our lab has demonstrated that FX remarkably decreased LPS-induced inflammation and improved survival in septic mice. Further investigation of the activity of FX against a wide range of diseases will require new approaches to uncover its molecular mechanism. This review will provide an outline of the current state of knowledge regarding FX application in the clinical setting and suggest future directions to implement FX as a therapeutic ingredient in pharmaceutical sciences in order to develop it into a treatment strategy against inflammation-associated disorders.
Topics: Mice; Animals; Xanthophylls; Inflammation; Obesity; Antioxidants
PubMed: 36432455
DOI: 10.3390/nu14224768 -
Journal of Natural Products Apr 2022A new manumycin-type natural product named pacificamide () and its candidate biosynthetic gene cluster () were discovered from the marine actinobacterium CNT-855. The... (Review)
Review
A new manumycin-type natural product named pacificamide () and its candidate biosynthetic gene cluster () were discovered from the marine actinobacterium CNT-855. The structure of the compound was determined using NMR, electronic circular dichroism, and bioinformatic predictions. The gene cluster is unique to and found in only two of the 119 genomes analyzed across nine species. Comparative analyses of biosynthetic gene clusters encoding the production of related manumycin-type compounds revealed genetic differences in accordance with the unique pacificamide structure. Further queries of manumycin-type gene clusters from public databases revealed their limited distribution across the phylum Actinobacteria and orphan diversity that suggests additional products remain to be discovered in this compound class. Production of the known metabolite triacsin D is also reported for the first time from the genus . This study adds two classes of compounds to the natural product collective isolated from the genus , which has proven to be a useful model for natural product research.
Topics: Biological Products; Micromonosporaceae; Multigene Family; Polyenes; Polyunsaturated Alkamides
PubMed: 35263117
DOI: 10.1021/acs.jnatprod.1c01117 -
Nutrients Jun 2023Dysregulation of lipid metabolism has been implicated in age-related macular degeneration (AMD), the leading cause of blindness among the elderly. Lecithin cholesterol...
Dysregulation of lipid metabolism has been implicated in age-related macular degeneration (AMD), the leading cause of blindness among the elderly. Lecithin cholesterol acyltransferase (LCAT) is an important enzyme responsible for lipid metabolism, which could be regulated by DNA methylation during the development of various age-related diseases. This study aimed to assess the association between LCAT DNA methylation and the risk of AMD, and to examine whether plasma vitamin and carotenoid concentrations modified this association. A total of 126 cases of AMD and 174 controls were included in the present analysis. LCAT DNA methylation was detected by quantitative real-time methylation-1specific PCR (qMSP). Circulating vitamins and carotenoids were measured using reversed-phase high-performance liquid chromatography (RP-HPLC). DNA methylation of LCAT was significantly higher in patients with AMD than those in the control subjects. After multivariable adjustment, participants in the highest tertile of LCAT DNA methylation had a 5.37-fold higher risk (95% CI: 2.56, 11.28) of AMD compared with those in the lowest tertile. Each standard deviation (SD) increment of LCAT DNA methylation was associated with a 2.23-fold (95% CI: 1.58, 3.13) increased risk of AMD. There was a J-shaped association between LCAT DNA methylation and AMD risk (P = 0.03). Higher concentrations of plasma retinol and β-cryptoxanthin were significantly associated with decreased levels of LCAT DNA methylation, with the multivariate-adjusted β coefficient being -0.05 (95% CI: -0.08, -0.01) and -0.25 (95% CI: -0.42, -0.08), respectively. In joint analyses of LCAT DNA methylation and plasma vitamin and carotenoid concentrations, the inverse association between increased LCAT DNA methylation and AMD risk was more pronounced among participants who had a lower concentration of plasma retinol and β-cryptoxanthin. These findings highlight the importance of comprehensively assessing LCAT DNA methylation and increasing vitamin and carotenoid status for the prevention of AMD.
Topics: Humans; Aged; Vitamins; Carotenoids; Vitamin A; Phosphatidylcholine-Sterol O-Acyltransferase; DNA Methylation; Beta-Cryptoxanthin; Macular Degeneration; Vitamin K
PubMed: 37447314
DOI: 10.3390/nu15132985 -
Lipids in Health and Disease Nov 2023Visceral adiposity index (VAI) and lipid accumulation product (LAP) are comprehensive indicators to evaluate visceral fat and determine the metabolic health of...
BACKGROUND
Visceral adiposity index (VAI) and lipid accumulation product (LAP) are comprehensive indicators to evaluate visceral fat and determine the metabolic health of individuals. Carotenoids are a group of naturally occurring antioxidants associated with several diseases. The purpose of this investigation was to explore the association between serum carotenoid concentration and VAI or LAP.
METHODS
The data were obtained from the National Health and Nutrition Examination Survey between 2001 and 2006. The levels of serum carotenoids were evaluated using high-performance liquid chromatography. Multivariate linear regression models were employed to investigate the relationship between levels of serum carotenoids and VAI or LAP. The potential non-linear relationship was determined using threshold effect analysis and fitted smoothing curves. Stratification analysis was performed to investigate the potential modifying factors.
RESULTS
In total, 5,084 participants were included in this population-based investigation. In the multivariate linear regressions, compared to the lowest quartiles of serum carotenoids, the highest quartiles were significantly associated with VAI, and the effect size (β) and 95% CI was - 0.98 (- 1.34, - 0.62) for α-carotene, - 1.39 (- 1.77, - 1.00) for β-carotene, - 0.79 (- 1.18, - 0.41) for β-cryptoxanthin, - 0.68 (- 0.96, - 0.39) for lutein/zeaxanthin, and - 0.88 (- 1.50, - 0.27) for trans-lycopene. Using piece-wise linear regression models, non-linear relationships were found between β-carotene and trans-lycopene and VAI with an inflection point of 2.44 (log2-transformed, ug/dL) and 3.80 (log2-transformed, ug/dL), respectively. The results indicated that α-carotene, β-cryptoxanthin, and lutein/zeaxanthin were linearly associated with VAI. An inverse association was also found between serum carotenoids and LAP after complete adjustments.
CONCLUSION
This study revealed that several serum carotenoids were associated with VAI or LAP among the general American population. Further large prospective investigations are warranted to support this finding.
Topics: Humans; Lycopene; beta Carotene; Nutrition Surveys; Cross-Sectional Studies; Lutein; Zeaxanthins; Beta-Cryptoxanthin; Lipid Accumulation Product; Adiposity; Prospective Studies; Carotenoids
PubMed: 38037060
DOI: 10.1186/s12944-023-01945-6