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New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II

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

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 34989

Special Issue Editors

Prof. Dr. Pedro Mena

E-Mail Website
Guest Editor
Human Nutrition Unit, Department of Veterinary Science, University of Parma, 43125 Parma, Italy
Interests: polyphenols; metabolites; colonic catabolites; plant bioactives; bioavailability; bioactivity; human intervention studies; individual variation; coffee; cocoa
Special Issues, Collections and Topics in MDPI journals
Dr. Rafael Llorach Asunción

E-Mail Website
Guest Editor
Biomarkers & Nutrimetabolomic group, Nutrition, Food Sciences and Gastronomy Department, XaRTA, INSA, Campus Torribera, Pharmacy Faculty, University of Barcelona, Barcelona, Spain
Interests: nutrimetabolomics; food science; nutrition; phytochemicals; phenolic compounds; food metabolome; biomarkers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We are pleased to inform you that Molecules will launch the second part of the Special Issue “New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds”.

With a fresh set of eyes and following the standards of a realistic research, this Special Issue should shed light on how (poly)phenolic substances are: (1) metabolized and turned into bioavailable molecules and (2) able to impact different biological processes related to human health. Phenolic compounds have shown promising health promotion features concerning the prevention of non-communicable diseases in epidemiological and human intervention studies. The elucidation of the metabolic fate of (poly)phenolic constituents and their bioavailability is a tipping point for fully unraveling the bioactive(s) responsible for phenolic compounds' demonstrated preventative effects on cardiovascular diseases, metabolic syndrome, neurodegenerative disorders, and certain kinds of cancer. There is a need for addressing: (1) the catabolism of phenolic compounds by the colonic microbiota and (2) the inter-individual differences in bioavailability and bioefficacy due to the diversity of microbiota composition. Moreover, future research should be focused on: (1) understanding the dose/phenolic intake–response relationship via pharmacokinetic studies and (2) evaluating proper biomarkers of intake. The design of nutritionally matched control–test foodstuffs is also required to conduct well‑controlled intervention studies in both animals and human subjects. In vitro investigations using physiologically achievable concentrations of (poly)phenol phase II metabolites with appropriate model test systems are also encouraged to provide adequate mechanistic insights. On the other hand, foodomics technologies (metabolomics, nutrigenomics, and proteomics) should be used to assess the role of phenolic bioactives from a comprehensive perspective. Likewise, any novel food-processing approach trying to enhance the bioavailability of (poly)phenols or sticking to what really happens after phenolic consumption should be taken into consideration. Finally, new communication channels and educational programs that are able to bring to the general public the well-defined biological properties of phenolics should be implemented. In conclusion, this Special Issue should review all aspects concerning the metabolism, bioavailability, and biological properties of (poly)phenolic compounds and discuss attempts to solve current critical gaps. Novel methodologies or out-of-the-box approaches can also complement the current knowledge and assist in the study of these plant bioactives.

Dr. Pedro Mena
Dr. Rafael Llorach Asunción
Guest Editors

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Keywords

  • Experimental realism
  • Phenolic compounds
  • Dietary plant bioactives
  • Colonic catabolism
  • Metabolomics
  • Phase II metabolites
  • Gut microbiota
  • Bioavailability
  • Bioactivity
  • Human intervention trials

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Related Special Issue

Published Papers (7 papers)

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Research

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10 pages, 707 KiB  
Article
The Effect of Formulation of Curcuminoids on Their Metabolism by Human Colonic Microbiota
by Letizia Bresciani, Claudia Favari, Luca Calani, Veronica Francinelli, Antonella Riva, Giovanna Petrangolini, Pietro Allegrini, Pedro Mena and Daniele Del Rio
Molecules 2020, 25(4), 940; https://doi.org/10.3390/molecules25040940 - 19 Feb 2020
Cited by 30 | Viewed by 4522
Abstract
Turmeric (Curcuma longa L.) is the only edible plant recognized as a dietary source of curcuminoids, among which curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (Bis-DMC) are the most representative ones. Curcumin shows a very low systemic bioavailability and for this reason, several technologies [...] Read more.
Turmeric (Curcuma longa L.) is the only edible plant recognized as a dietary source of curcuminoids, among which curcumin, demethoxycurcumin (DMC) and bis-demethoxycurcumin (Bis-DMC) are the most representative ones. Curcumin shows a very low systemic bioavailability and for this reason, several technologies have been adopted to improve it. These technologies generally improve curcuminoid absorption in the small intestine, however, no data are available about the effect of curcuminoid formulation on colonic biotransformation. The present study aims at investigating the human colonic metabolism of curcuminoids, prepared with two different technologies, using an in vitro model. Unformulated curcuminoid and lecithin-curcuminoid botanical extracts were fermented using an in vitro fecal model and colonic catabolites were identified and quantified by uHPLC-MSn. Native compounds, mainly curcumin, DMC and bis-DMC, were metabolized by colonic microbiota within the 24-h incubation. The degradation of curcuminoids led to the formation of specific curcuminoid metabolites, among which higher concentrations of bis(demethyl)-tetrahydrocurcumin and bis(demethyl)-hexahydrocurcumin were found after lecithin-extract fermentation compared to the concentration detected after unformulated extract. In conclusion, both curcumin-based botanical extracts can be considered important sources of curcuminoids, although the lecithin-formulated extract led to a higher production of curcuminoid catabolites. Moreover, a new curcuminoid catabolite, namely bis(demethyl)-hexahydrocurcumin, has been putatively identified, opening new perspectives in the investigation of curcuminoid bioavailability and their potential metabolite bioactivity. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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16 pages, 1515 KiB  
Article
Anthocyanin Metabolites in Human Urine after the Intake of New Functional Beverages
by Vicente Agulló, Débora Villaño, Cristina García-Viguera and Raúl Domínguez-Perles
Molecules 2020, 25(2), 371; https://doi.org/10.3390/molecules25020371 - 16 Jan 2020
Cited by 30 | Viewed by 4137
Abstract
Sugar intake abuse is directly related with the increase of metabolic diseases such as type 2 diabetes, obesity, and insulin resistance. Along this line, the development of new beverages using alternative sweeteners could help with combatting the pathophysiological disorders associated to the consumption [...] Read more.
Sugar intake abuse is directly related with the increase of metabolic diseases such as type 2 diabetes, obesity, and insulin resistance. Along this line, the development of new beverages using alternative sweeteners could help with combatting the pathophysiological disorders associated to the consumption of sugar. To provide evidence on this issue, in the present work, the bioavailability of anthocyanins was evaluated after the acute ingestion of a new maqui-citrus-based functional beverage rich in polyphenols, and supplemented with a range of sweeteners including sucrose (natural high caloric), stevia (natural non-caloric), and sucralose (artificial non-caloric), as an approach that would allow reducing the intake of sugars while providing bioactive phenolic compounds (anthocyanins). This approach allowed the evaluation of the maximum absorption and the diversity of metabolites excreted through urine. The beverages created were ingested by volunteers (n = 20) and the resulting anthocyanin metabolites in their urine were analyzed by UHPLC-ESI-MS/MS. A total of 29 degradation metabolites were detected: Caffeic acid, catechol, 3,4-dihidroxifenilacetic acid, hippuric acid, trans-ferulic acid, 2,4,6-trihydroxybenzaldehyde, trans-isoferulic acid, and vanillic acid derivatives, where peak concentrations were attained at 3.5 h after beverage intake. Sucralose was the sweetener that provided a higher bioavailability for most compounds, followed by stevia. Sucrose did not provide a remarkably higher bioavailability of any compounds in comparison with sucralose or stevia. The results propose two sweetener alternatives (sucralose and stevia) to sucrose, an overused high calorie sweetener that promotes some metabolic diseases. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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11 pages, 781 KiB  
Article
Bioavailability and Bioactivity of Encapsulated Phenolics and Carotenoids Isolated from Red Pepper Waste
by Jelena Vulić, Vanja Šeregelj, Ana Kalušević, Steva Lević, Viktor Nedović, Vesna Tumbas Šaponjac, Jasna Čanadanović-Brunet and Gordana Ćetković
Molecules 2019, 24(15), 2837; https://doi.org/10.3390/molecules24152837 - 5 Aug 2019
Cited by 62 | Viewed by 5390
Abstract
In order to deactivate the health properties of bioactive compounds, they need to withstand the effects of food processing, their potential release from the food matrix, and remain bio-accessible in the gastrointestinal tract. Bio-actives from different plants are prone to oxidative degradation, and [...] Read more.
In order to deactivate the health properties of bioactive compounds, they need to withstand the effects of food processing, their potential release from the food matrix, and remain bio-accessible in the gastrointestinal tract. Bio-actives from different plants are prone to oxidative degradation, and encapsulation is an effective method in improving their stability. In the present study, red pepper waste (RPW), a by-product of vegetable processing industry, was encapsulated in whey protein using spray and freeze-drying techniques. The aim was to evaluate the effects of in vitro gastrointestinal digestion on the release and bioactivity of encapsulated bio-actives, after each digestion step. The results showed that the release of phenolics and carotenoids, as well as antioxidants, anti-hyperglycemic, and anti-inflammatory activities are influenced by pH and intestinal fluid, with pH 7.5 exhibited at higher levels. There was a rapid initial release of carotenoids from whey protein matrices, while a more gradual increase of phenolics was observed, reaching around 50% for both encapsulates first at 6 h and 37 °C, and small intestine conditions. The encapsulation of RPW demonstrated a protective effect against pH changes and enzymatic activities along digestion, and contributed to the increase in bio-accessibility in the gut. Also, the results suggest that encapsulation is an efficient method for valorization of bio-actives from RPW, with improvements in nutrition, color, and bioactive properties. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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19 pages, 1498 KiB  
Article
Polyphenolic and Physicochemical Properties of Simple-Spined Num-Num (Carissa edulis) Fruit Harvested at Ripe Stage of Maturation
by Fulufhelo P. Makumbele, Malcolm Taylor, Marietjie Stander, Tonna A. Anyasi and Afam I.O. Jideani
Molecules 2019, 24(14), 2630; https://doi.org/10.3390/molecules24142630 - 19 Jul 2019
Cited by 7 | Viewed by 4785
Abstract
Wildly grown in most regions of the world, Carissa edulis is a highly underutilised fruit with significant antioxidant characteristics. The phyto and physicochemical properties of C. edulis berries at different stages of ripening are evaluated in this work. Total flavonoids (TF), total phenolic [...] Read more.
Wildly grown in most regions of the world, Carissa edulis is a highly underutilised fruit with significant antioxidant characteristics. The phyto and physicochemical properties of C. edulis berries at different stages of ripening are evaluated in this work. Total flavonoids (TF), total phenolic content (TPC) and antioxidant activity were determined spectrophotometrically, while concentration of polyphenols was determined using liquid chromatography coupled to diode array detection and electrospray ionization mass spectrometry. Results showed that antioxidant activity was lowest (18.36 ± 0.12 mmol TE/g) in RS3 and decreased with TPC upon increased ripening. Conversely, TF increased with ripening progression with TF found to be highest in RS3 (5.92 ± 0.03 mg CE/g). Identified phenolic acids in C. edulis were quinic acid, protocatechuoyl-hexose, neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and dicaffeoylquinic acid. Identified flavonoids included rutin, catechin, procyanidin dimer, procyanidin trimer, quercetin-3-O-glucosyl-xyloside, quercetin-3-O-robinobioside, quercetin-3-O-glucoside and quercetin-3-OH-3-methylglutaryl-glucoside. Physicochemical properties of C. edulis varied among samples with sugar/acid ratio of C. edulis ranging from 25.70 for RS1 to 50.36 for RS3. Ripening stage of C. edulis undoubtedly affects the phyto and physicochemical properties of C. edulis. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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11 pages, 1281 KiB  
Article
Metabolism of Stilbenoids by Human Faecal Microbiota
by Veronika Jarosova, Ondrej Vesely, Petr Marsik, Jose Diogenes Jaimes, Karel Smejkal, Pavel Kloucek and Jaroslav Havlik
Molecules 2019, 24(6), 1155; https://doi.org/10.3390/molecules24061155 - 23 Mar 2019
Cited by 36 | Viewed by 4025
Abstract
Stilbenoids are dietary phenolics with notable biological effects on humans. Epidemiological, clinical, and nutritional studies from recent years have confirmed the significant biological effects of stilbenoids, such as oxidative stress protection and the prevention of degenerative diseases, including cancer, cardiovascular diseases, and neurodegenerative [...] Read more.
Stilbenoids are dietary phenolics with notable biological effects on humans. Epidemiological, clinical, and nutritional studies from recent years have confirmed the significant biological effects of stilbenoids, such as oxidative stress protection and the prevention of degenerative diseases, including cancer, cardiovascular diseases, and neurodegenerative diseases. Stilbenoids are intensively metabolically transformed by colon microbiota, and their corresponding metabolites might show different or stronger biological activity than their parent molecules. The aim of the present study was to determine the metabolism of six stilbenoids (resveratrol, oxyresveratrol, piceatannol, thunalbene, batatasin III, and pinostilbene), mediated by colon microbiota. Stilbenoids were fermented in an in vitro faecal fermentation system using fresh faeces from five different donors as an inoculum. The samples of metabolized stilbenoids were collected at 0, 2, 4, 8, 24, and 48 h. Significant differences in the microbial transformation among stilbene derivatives were observed by liquid chromatography mass spectrometry (LC/MS). Four stilbenoids (resveratrol, oxyresveratrol, piceatannol and thunalbene) were metabolically transformed by double bond reduction, dihydroxylation, and demethylation, while batatasin III and pinostilbene were stable under conditions simulating the colon environment. Strong inter-individual differences in speed, intensity, and pathways of metabolism were observed among the faecal samples obtained from the donors. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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25 pages, 2545 KiB  
Article
Effect of Selected Stilbenoids on Human Fecal Microbiota
by Jose D. Jaimes, Veronika Jarosova, Ondrej Vesely, Chahrazed Mekadim, Jakub Mrazek, Petr Marsik, Jiri Killer, Karel Smejkal, Pavel Kloucek and Jaroslav Havlik
Molecules 2019, 24(4), 744; https://doi.org/10.3390/molecules24040744 - 19 Feb 2019
Cited by 18 | Viewed by 4192
Abstract
Dietary phenolics or polyphenols are mostly metabolized by the human gut microbiota. These metabolites appear to confer the beneficial health effects attributed to phenolics. Microbial composition affects the type of metabolites produced. Reciprocally, phenolics modulate microbial composition. Understanding this relationship could be used [...] Read more.
Dietary phenolics or polyphenols are mostly metabolized by the human gut microbiota. These metabolites appear to confer the beneficial health effects attributed to phenolics. Microbial composition affects the type of metabolites produced. Reciprocally, phenolics modulate microbial composition. Understanding this relationship could be used to positively impact health by phenolic supplementation and thus create favorable colonic conditions. This study explored the effect of six stilbenoids (batatasin III, oxyresveratrol, piceatannol, pinostilbene, resveratrol, thunalbene) on the gut microbiota composition. Stilbenoids were anaerobically fermented with fecal bacteria from four donors, samples were collected at 0 and 24 h, and effects on the microbiota were assessed by 16S rRNA gene sequencing. Statistical tests identified affected microbes at three taxonomic levels. Observed microbial composition modulation by stilbenoids included a decrease in the Firmicutes to Bacteroidetes ratio, a decrease in the relative abundance of strains from the genus Clostridium, and effects on the family Lachnospiraceae. A frequently observed effect was a further decrease of the relative abundance when compared to the control. An opposite effect to the control was observed for Faecalibacterium prausnitzii, whose relative abundance increased. Observed effects were more frequently attributed to resveratrol and piceatannol, followed by thunalbene and batatasin III. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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Review

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15 pages, 348 KiB  
Review
Roles of Phenolic Compounds in the Reduction of Risk Factors of Cardiovascular Diseases
by Mariane Lutz, Eduardo Fuentes, Felipe Ávila, Marcelo Alarcón and Iván Palomo
Molecules 2019, 24(2), 366; https://doi.org/10.3390/molecules24020366 - 21 Jan 2019
Cited by 82 | Viewed by 7269
Abstract
The population is now living longer during the period classified as “elderly” (60 years and older), exhibiting multimorbidity associated to the lengthening of the average life span. The dietary intake of phenolic compounds (PC) may affect the physiology, disease development and progression during [...] Read more.
The population is now living longer during the period classified as “elderly” (60 years and older), exhibiting multimorbidity associated to the lengthening of the average life span. The dietary intake of phenolic compounds (PC) may affect the physiology, disease development and progression during the aging process, reducing risk factors of age related diseases. The aim of this review is to briefly describe some of the possible effects of a series of PC on the reduction of risk factors of the onset of cardiovascular diseases, considering their potential mechanisms of action. The main actions described for PC are associated with reduced platelet activity, anti-inflammatory effects, and the protection from oxidation to reduce LDL and the generation of advanced glycation end products. Preclinical and clinical evidence of the physiological effects of various PC is presented, as well as the health claims approved by regulatory agencies. Full article
(This article belongs to the Special Issue New Frontiers on the Metabolism, Bioavailability and Health Effects of Phenolic Compounds II)
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