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Special Issue "Dietary Bioactive Compounds: Metabolism, Mechanisms and Translational Significance for Health and Prevention of Diseases"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Metabolites".

Deadline for manuscript submissions: closed (30 June 2015)

Special Issue Editors

Guest Editor
Dr. Emilie Combet

Department of Human Nutrition, School of Medicine, Dentistry and Nursing, College of Medical, Veterinary and Life Sciences, University of Glasgow, Glasgow, UK
Website | E-Mail
Interests: farm-to-fork; nutrition and the lifecycle; nutrition and stress
Guest Editor
Prof. Dr. Maria Rosário Bronze

Faculdade de Farmácia, Universidade de Lisboa, Av. das Forças Armadas, 1649-019, Lisboa, Portugal
Website | E-Mail
Phone: 00351217946400

Special Issue Information

Dear Colleagues,

A large range of molecules (often non-nutrients) found in the diet hold bioactive properties. A non-exhaustive list include the large (poly)phenolic family of compounds, glucosinolates, phytoestrogens, plant sterols, long chain fatty acids, selected vitamins and minerals, cereal fibre, and carotenoids.
Selected foods, predominantly of plant origin, have gained an important place in the consumer’s diet with a view to sustain health. The focus on dietary bioactive compounds is directly aligned with the emergence of functional foods in the last two decades, in parallel with the need to substantiate health claims.
Experimental design and appropriate methodologies are especially important to ascertain the metabolism, biological function, and mechanism of action of dietary bioactive compounds. An important addition is the need to discuss the translational value of these findings, and how they can influence commercial potential, public health, and clinical decision-making.
Contributions to this issue, both in the form of original research or review articles, may cover all aspects of dietary bioactive compound research, linking metabolism, biological function, and health or disease prevention. Studies with multidisciplinary input, offering new methodologies or insights are particularly welcome.

Dr. Emilie Combet
Dr. Maria Rosário Bronze
Guest Editors

Manuscript Submission Information

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Keywords

  • diet
  • functional foods
  • bioactive compounds
  • health
  • disease prevention
  • metabolism
  • function
  • mechanism of action
  • health claims

Published Papers (11 papers)

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Research

Jump to: Review

Open AccessArticle Protective Effect of a (Poly)phenol-Rich Extract Derived from Sweet Cherries Culls against Oxidative Cell Damage
Molecules 2016, 21(4), 406; doi:10.3390/molecules21040406
Received: 16 December 2015 / Revised: 3 March 2016 / Accepted: 7 March 2016 / Published: 24 March 2016
Cited by 1 | PDF Full-text (832 KB) | HTML Full-text | XML Full-text
Abstract
Oxidative stress is one of the key phenomena behind the most common types of chronic diseases. Therefore, the modulation of oxidative stress is an interesting target for acting either through prevention or as a therapeutic approach. In this work, a Portuguese variety of
[...] Read more.
Oxidative stress is one of the key phenomena behind the most common types of chronic diseases. Therefore, the modulation of oxidative stress is an interesting target for acting either through prevention or as a therapeutic approach. In this work, a Portuguese variety of cherry (Saco Cherry) was processed in order to obtain a potent in vitro antioxidant phenolic-rich extract (Ch-PRE), which was further explored to evaluate its potential application as nutraceutical agent against cellular oxidative stress damage. Ch-PRE was mainly composed of anthocyanins, particularly cyanidin-3-rutinoside, cyanidin-3-glucoside, peonidin-3-glucoside and neochlorogenic acid, and exhibited a potent chemical antioxidant activity expressed by its oxygen radical absorbance capacity (ORAC) and hydroxyl radical averting capacity (HORAC) values. Ch-PRE also displayed effective intracellular radical scavenging properties in intestinal epithelial and neuronal cells challenged with oxidative stress but showed a different order of effectiveness regarding the modulation of endogenous antioxidant system. Ch-PRE could be an attractive candidate to formulate an agent for the prevention of oxidative stress-induced disorders such as intestinal inflammation disorders or with an appropriated delivery system for neurodegenerative diseases. Full article
Open AccessArticle Ellagitannins and Flavan-3-ols from Raspberry Pomace Modulate Caecal Fermentation Processes and Plasma Lipid Parameters in Rats
Molecules 2015, 20(12), 22848-22862; doi:10.3390/molecules201219878
Received: 5 October 2015 / Revised: 25 November 2015 / Accepted: 14 December 2015 / Published: 21 December 2015
Cited by 4 | PDF Full-text (478 KB) | HTML Full-text | XML Full-text
Abstract
Raspberry pomace is a source of polyphenols, which nutritional and health promoting properties are not sufficiently known. The aim of this 8-weeks study was to scrutinize if raspberry extracts (REs) with different ellagitannins to flavan-3-ols ratios might favorably affect the caecal fermentation processes
[...] Read more.
Raspberry pomace is a source of polyphenols, which nutritional and health promoting properties are not sufficiently known. The aim of this 8-weeks study was to scrutinize if raspberry extracts (REs) with different ellagitannins to flavan-3-ols ratios might favorably affect the caecal fermentation processes and blood lipid profile in rats. Forty male Wistar rats were fed with a standard diet or its modification with two types of REs (E1 and E2) characterized by different ratios of ellagitannins to flavan-3-ols (7.7 and 3.1 for E1 and E2, respectively) and added to a diet at two dosages of polyphenolic compounds (0.15 and 0.30% of a diet; L and H treatments, respectively). Irrespective of polyphenols dietary level, both REs reduced the activity of bacterial β-glucuronidase, increased production of butyric acid in the caecum and reduced triacylglycerols in blood plasma. The E1 treatment at both dosages caused more effective reduction in the concentration of ammonia and elevated acetate level in the caecal digesta than E2. On the other hand, only the E2 treatment lowered value of the atherogenic index when compared with control group. When comparing dosages of REs, a higher one was more potent to reduce the activity of bacterial β-glucosidase, β-, α-galactosidase and lowered value of the HDL profile in plasma. To conclude, REs may favorably modulate the activity of the caecal microbiota and blood lipid profile in rats; however, the intensity of these effects may be related to the dosages of dietary polyphenols and to their profile, e.g., ellagitannins to flavan-3-ols ratio. Full article
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Open AccessArticle Targeted and Untargeted Metabolomics to Explore the Bioavailability of the Secoiridoids from a Seed/Fruit Extract (Fraxinus angustifolia Vahl) in Human Healthy Volunteers: A Preliminary Study
Molecules 2015, 20(12), 22202-22219; doi:10.3390/molecules201219845
Received: 9 November 2015 / Revised: 30 November 2015 / Accepted: 4 December 2015 / Published: 11 December 2015
Cited by 2 | PDF Full-text (2969 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The bark, seeds, fruits and leaves of the genus Fraxinus (Oleaceae) which contain a wide range of phytochemicals, mostly secoiridoid glucosides, have been widely used in folk medicine against a number of ailments, yet little is known about the metabolism and uptake of
[...] Read more.
The bark, seeds, fruits and leaves of the genus Fraxinus (Oleaceae) which contain a wide range of phytochemicals, mostly secoiridoid glucosides, have been widely used in folk medicine against a number of ailments, yet little is known about the metabolism and uptake of the major Fraxinus components. The aim of this work was to advance in the knowledge on the bioavailability of the secoiridoids present in a Fraxinus angustifolia Vahl seed/fruit extract using both targeted and untargeted metabolomic analyses. Plasma and urine samples from nine healthy volunteers were taken at specific time intervals following the intake of the extract and analyzed by UPLC-ESI-QTOF. Predicted metabolites such as tyrosol and ligstroside-aglycone glucuronides and sulfates were detected at low intensity. These compounds reached peak plasma levels 2 h after the intake and exhibited high variability among the participants. The ligstroside-aglycone conjugates may be considered as potential biomarkers of the Fraxinus secoiridoids intake. Using the untargeted approach we additionally detected phenolic conjugates identified as ferulic acid and caffeic acid sulfates, as well as hydroxybenzyl and hydroxyphenylacetaldehyde sulfate derivatives which support further metabolism of the secoiridoids by phase I and (or) microbial enzymes. Overall, the results of this study suggest low uptake of intact secoiridoids from a Fraxinus angustifolia Vahl extract in healthy human volunteers and metabolic conversion by esterases, glycosidases, and phase II sulfo- and glucuronosyl transferases to form smaller conjugated derivatives. Full article
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Open AccessArticle In Vitro Antioxidant Activities and in Vivo Anti-Hypoxic Activity of the Edible Mushroom Agaricus bisporus (Lange) Sing. Chaidam
Molecules 2015, 20(10), 17775-17788; doi:10.3390/molecules201017775
Received: 10 June 2015 / Revised: 11 September 2015 / Accepted: 18 September 2015 / Published: 25 September 2015
Cited by 6 | PDF Full-text (3512 KB) | HTML Full-text | XML Full-text
Abstract
With the rising awareness of a healthy lifestyle, natural functional foods have gained much interest as promising alternatives to synthetic functional drugs. Recently, wild Agaricus bisporus (Lange) Sing. Chaidam has been found and artificially cultivated for its thick fresh body and excellent taste,
[...] Read more.
With the rising awareness of a healthy lifestyle, natural functional foods have gained much interest as promising alternatives to synthetic functional drugs. Recently, wild Agaricus bisporus (Lange) Sing. Chaidam has been found and artificially cultivated for its thick fresh body and excellent taste, with its antioxidant and anti-hypoxic abilities unknown. In this work, the antioxidant potential of its methanolic, 55% ethanolic, aqueous extracts and crude polysaccharide was evaluated in different systems. The results showed that polysaccharide was the most effective in scavenging ability on 2,2-diphenyl-1-picrylhydrazyl (DPPH) and hydroxyl radicals, metal chelating activity and reducing power, with EC50 values of 0.02, 2.79, 1.29, and 1.82 mg/mL, respectively. Therefore, we further studied the anti-hypoxic activity of crude polysaccharide. The results turned out that polysaccharide (300 mg/kg) prolonged the survival time, decreased the blood urea nitrogen and lactic acid content as well as increased the liver glycogen significantly, compared with the blank control and the commercialized product Hongjingtian (p < 0.05). With such excellent activities, we purified the polysaccharide and analyzed its molecular weight (120 kDa) as well as monosaccharide components (glucose, fructose and mannose). This study indicated that wild Agaricus bisporus (Lange) Sing. Chaidam had strong potential to be exploited as an effective natural functional food to relieve oxidative and hypoxia stresses Full article
Open AccessArticle N-Monosubstituted Methoxy-oligo(ethylene glycol) Carbamate Ester Prodrugs of Resveratrol
Molecules 2015, 20(9), 16085-16102; doi:10.3390/molecules200916085
Received: 28 July 2015 / Revised: 27 August 2015 / Accepted: 28 August 2015 / Published: 3 September 2015
Cited by 4 | PDF Full-text (1237 KB) | HTML Full-text | XML Full-text
Abstract
Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on
[...] Read more.
Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3–[OCH2CH2]n–) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption. Full article
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Open AccessArticle Antigenotoxicity and Tumor Growing Inhibition by Leafy Brassica carinata and Sinigrin
Molecules 2015, 20(9), 15748-15765; doi:10.3390/molecules200915748
Received: 26 June 2015 / Revised: 12 August 2015 / Accepted: 25 August 2015 / Published: 28 August 2015
Cited by 6 | PDF Full-text (947 KB) | HTML Full-text | XML Full-text
Abstract
Cruciferous vegetables are well known and worldwide consumed due to their health benefits and cancer prevention properties. As a desirable cruciferous plant, Ethiopian mustard (Brassica carinata A. Braun) and its glucosinolate sinigrin were tested in the in vivo Drosophila melanogaster (SMART) and
[...] Read more.
Cruciferous vegetables are well known and worldwide consumed due to their health benefits and cancer prevention properties. As a desirable cruciferous plant, Ethiopian mustard (Brassica carinata A. Braun) and its glucosinolate sinigrin were tested in the in vivo Drosophila melanogaster (SMART) and the in vitro HL60 (human promyelocytic leukaemia cell line) systems. High performance liquid chromatography (HPLC) analysis of plant samples confirmed the presence of sinigrin as principal B. carinata glucosinolate. SMART was performed by feeding D. melanogaster larvae either with different concentrations of plant/compound samples or combining them with hydrogen peroxide (a potent oxidative mutagen) being both antimutagenics. HL60 assays showed the tumoricidal activity of plant samples (IC50 = 0.28 mg·mL−1) and the breakdown products of sinigrin hydrolysis (IC50 = 2.71 µM). Our results enhance the potential of B. carinata as health promoter and chemopreventive in both systems and the leading role of sinigrin in these effects. Full article
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Open AccessArticle Effects of Dietary Brazilian Palm Oil (Mauritia flexuosa L.) on Cholesterol Profile and Vitamin A and E Status of Rats
Molecules 2015, 20(5), 9054-9070; doi:10.3390/molecules20059054
Received: 25 February 2015 / Revised: 6 May 2015 / Accepted: 11 May 2015 / Published: 19 May 2015
Cited by 5 | PDF Full-text (774 KB) | HTML Full-text | XML Full-text
Abstract
In vitro studies have been carried out to establish the nutritional differences between crude and refined vegetable oils; however, the impact of the consumption of these foods on metabolism, in particular the effect of buriti oil, needs to be further evaluated. The aim
[...] Read more.
In vitro studies have been carried out to establish the nutritional differences between crude and refined vegetable oils; however, the impact of the consumption of these foods on metabolism, in particular the effect of buriti oil, needs to be further evaluated. The aim of this study was to evaluate the biochemical and murine parameters and the vitamin A and E status in young rats fed with diets supplemented with crude or refined buriti oil. The animals (n = 30) were randomized into three groups receiving diet added of soybean oil (control), crude buriti oil (CBO) and refined buriti oil (RBO) for 28 days. Rats fed with diet added of refined buriti oil (RBO) showed reduced total cholesterol (up to 60.27%), LDL (64.75%), triglycerides (55.47%) and enzyme aspartate transaminase (21.57%) compared to those fed with diet added of crude oil. Serum and hepatic retinol and tocopherol were higher by two to three times in CBO and RBO groups compared to the control group, but no differences were observed for murine parameters. The results indicate that buriti oil is an important source of the antioxidant vitamins A and E, and refined buriti oil is suggested as alternative to improve the lipid profile of healthy rats. Full article
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Review

Jump to: Research

Open AccessReview Ursolic Acid—A Pentacyclic Triterpenoid with a Wide Spectrum of Pharmacological Activities
Molecules 2015, 20(11), 20614-20641; doi:10.3390/molecules201119721
Received: 3 July 2015 / Revised: 21 August 2015 / Accepted: 23 September 2015 / Published: 19 November 2015
Cited by 39 | PDF Full-text (1177 KB) | HTML Full-text | XML Full-text
Abstract
Ursolic acid (UA) is a natural terpene compound exhibiting many pharmaceutical properties. In this review the current state of knowledge about the health-promoting properties of this widespread, biologically active compound, as well as information about its occurrence and biosynthesis are presented. Particular attention
[...] Read more.
Ursolic acid (UA) is a natural terpene compound exhibiting many pharmaceutical properties. In this review the current state of knowledge about the health-promoting properties of this widespread, biologically active compound, as well as information about its occurrence and biosynthesis are presented. Particular attention has been paid to the application of ursolic acid as an anti-cancer agent; it is worth noticing that clinical tests suggesting the possibility of practical use of UA have already been conducted. Amongst other pharmacological properties of UA one can mention protective effect on lungs, kidneys, liver and brain, anti-inflammatory properties, anabolic effects on skeletal muscles and the ability to suppress bone density loss leading to osteoporosis. Ursolic acid also exhibits anti-microbial features against numerous strains of bacteria, HIV and HCV viruses and Plasmodium protozoa causing malaria. Full article
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Open AccessReview Effects of Flavonoids from Food and Dietary Supplements on Glial and Glioblastoma Multiforme Cells
Molecules 2015, 20(10), 19406-19432; doi:10.3390/molecules201019406
Received: 31 July 2015 / Revised: 21 September 2015 / Accepted: 14 October 2015 / Published: 23 October 2015
Cited by 9 | PDF Full-text (892 KB) | HTML Full-text | XML Full-text
Abstract
Quercetin, catechins and proanthocyanidins are flavonoids that are prominently featured in foodstuffs and dietary supplements, and may possess anti-carcinogenic activity. Glioblastoma multiforme is the most dangerous form of glioma, a malignancy of the brain connective tissue. This review assesses molecular structures of these
[...] Read more.
Quercetin, catechins and proanthocyanidins are flavonoids that are prominently featured in foodstuffs and dietary supplements, and may possess anti-carcinogenic activity. Glioblastoma multiforme is the most dangerous form of glioma, a malignancy of the brain connective tissue. This review assesses molecular structures of these flavonoids, their importance as components of diet and dietary supplements, their bioavailability and ability to cross the blood-brain barrier, their reported beneficial health effects, and their effects on non-malignant glial as well as glioblastoma tumor cells. The reviewed flavonoids appear to protect glial cells via reduction of oxidative stress, while some also attenuate glutamate-induced excitotoxicity and reduce neuroinflammation. Most of the reviewed flavonoids inhibit proliferation of glioblastoma cells and induce their death. Moreover, some of them inhibit pro-oncogene signaling pathways and intensify the effect of conventional anti-cancer therapies. However, most of these anti-glioblastoma effects have only been observed in vitro or in animal models. Due to limited ability of the reviewed flavonoids to access the brain, their normal dietary intake is likely insufficient to produce significant anti-cancer effects in this organ, and supplementation is needed. Full article
Open AccessReview Biological and Nutritional Properties of Palm Oil and Palmitic Acid: Effects on Health
Molecules 2015, 20(9), 17339-17361; doi:10.3390/molecules200917339
Received: 31 July 2015 / Revised: 2 September 2015 / Accepted: 9 September 2015 / Published: 18 September 2015
Cited by 20 | PDF Full-text (1666 KB) | HTML Full-text | XML Full-text
Abstract
A growing body of evidence highlights the close association between nutrition and human health. Fat is an essential macronutrient, and vegetable oils, such as palm oil, are widely used in the food industry and highly represented in the human diet. Palmitic acid, a
[...] Read more.
A growing body of evidence highlights the close association between nutrition and human health. Fat is an essential macronutrient, and vegetable oils, such as palm oil, are widely used in the food industry and highly represented in the human diet. Palmitic acid, a saturated fatty acid, is the principal constituent of refined palm oil. In the last few decades, controversial studies have reported potential unhealthy effects of palm oil due to the high palmitic acid content. In this review we provide a concise and comprehensive update on the functional role of palm oil and palmitic acid in the development of obesity, type 2 diabetes mellitus, cardiovascular diseases and cancer. The atherogenic potential of palmitic acid and its stereospecific position in triacylglycerols are also discussed. Full article
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Open AccessReview Metabolic and Microbial Modulation of the Large Intestine Ecosystem by Non-Absorbed Diet Phenolic Compounds: A Review
Molecules 2015, 20(9), 17429-17468; doi:10.3390/molecules200917429
Received: 4 August 2015 / Revised: 31 August 2015 / Accepted: 11 September 2015 / Published: 18 September 2015
Cited by 17 | PDF Full-text (1438 KB) | HTML Full-text | XML Full-text
Abstract
Phenolic compounds represent a diverse group of phytochemicals whose intake is associated with a wide spectrum of health benefits. As consequence of their low bioavailability, most of them reach the large intestine where, mediated by the action of local microbiota, a series of
[...] Read more.
Phenolic compounds represent a diverse group of phytochemicals whose intake is associated with a wide spectrum of health benefits. As consequence of their low bioavailability, most of them reach the large intestine where, mediated by the action of local microbiota, a series of related microbial metabolites are accumulated. In the present review, gut microbial transformations of non-absorbed phenolic compounds are summarized. Several studies have reached a general consensus that unbalanced diets are associated with undesirable changes in gut metabolism that could be detrimental to intestinal health. In terms of explaining the possible effects of non-absorbed phenolic compounds, we have also gathered information regarded their influence on the local metabolism. For this purpose, a number of issues are discussed. Firstly, we consider the possible implications of phenolic compounds in the metabolism of colonic products, such as short chain fatty acids (SCFA), sterols (cholesterol and bile acids), and microbial products of non-absorbed proteins. Due to their being recognized as affective antioxidant and anti-inflammatory agents, the ability of phenolic compounds to counteract or suppress pro-oxidant and/or pro-inflammatory responses, triggered by bowel diseases, is also presented. The modulation of gut microbiota through dietetic maneuvers including phenolic compounds is also commented on. Although the available data seems to assume positive effects in terms of gut health protection, it is still insufficient for solid conclusions to be extracted, basically due to the lack of human trials to confirm the results obtained by the in vitro and animal studies. We consider that more emphasis should be focused on the study of phenolic compounds, particularly in their microbial metabolites, and their power to influence different aspects of gut health. Full article

Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Type of Paper: Article
Title: New Carbamate Ester Prodrugs of Resveratrol. Synthesis, Characterization and in vivo Behavior
Authors: Andrea Mattarei 1,2, Michele Azzolini 3, Martina La Spina 2,3, Mario Zoratti 2,3, Lucia Biasutto2,3, Cristina Paradisi 1
Affiliation: 1 Department of Chemical Sciences, Via F. Marzolo 1, 35131 Padova, Italy
2 CNR Neuroscience Institute, Viale G. Colombo 3, 35121 Padova, Italy
3 Dept. Biomedical Sciences, University of Padova, Viale G. Colombo 3, 35121 Padova, Italy
Abstract: Resveratrol (3, 5, 4’-trihydroxy-trans-stilbene) exerts important biological activities, but its pharmacological exploitation in vivo is hindered by its rapid elimination via phase-II conjugative metabolism in the intestine and in the liver. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, stability and in vivo pharmacokinetics of 7 prodrugs of resveratrol, in which the OH groups are engaged in an N-monosubstituted carbamate ester and the isoleucine-comprising prodrugs were measurably absorbed, reaching the circulation as non-metabolized and partially hydrolyzed species.
The results suggest that prodrugs of resveratrol based on the N-monosubstituted carbamate ester bond may be a tool for the systemic delivery of the unconjugated parent compound; the promoiety linked to the nitrogen atom appears to be a key factor in modulating the properties of the prodrug.
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