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Food Bioactives: Chemical Challenges and Bio-Opportunities

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

Deadline for manuscript submissions: closed (29 February 2020) | Viewed by 50474

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Prof. Dr. Severina Pacifico

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Department of Environmental Biological and Pharmaceutical Sciences and Technologies, Università degli Studi della Campania Luigi Vanvitelli, Naples, Italy
Interests: food chemistry; natural products chemistry; nutraceuticals; mass spectrometry polyphenols; chemoprevention
Special Issues, Collections and Topics in MDPI journals

Dr. Simona Piccolella

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Dear Colleagues,

A full awareness of the role played by a healthy diet, as part of a healthy lifestyle, in countering or slowing-down chronic and degenerative diseases has strongly increased the interest in food bioactives and the return of ancient but nowadays functionally considered foods. In fact, these dietary substances, to which nutraceutical attributes are increasingly entrusted, could display disease-preventing effects on animals and humans. In this context, polyphenols, which are widespread and mostly copious in dietary plant sources, have gained a lot of attention thanks to their potential ability to halt or reverse oxidative stress-related diseases. Indeed, food could contain, beyond health-promoting compounds, toxicants, which are naturally occurring or process-induced dietary compounds with adverse effects on human health. Bioactives’ presence and abundance are strictly related to their food source. Edible plant components largely contain beneficial secondary metabolites, but understanding them fully is still an important challenge as complex biotic and abiotic interactions are involved in their biosynthesis. Analytical methods, which are increasingly powerful, could enhance our knowledge of food bioactives, whereas the deep investigation of their bioactivity and bioavailability could make them particularly useful.

This Special Issue aims to attract contributions on analytical challenges in food bioactives’ chemistry and bioactivity, which form the basis of proper bio-opportunities.

Prof. Dr. Severina Pacifico
Dr. Simona Piccolella
Guest Editors

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Keywords

Food bioactives
Nutraceuticals
Mass spectrometry
Spectroscopic techniques
Natural products bioactivity

Published Papers (11 papers)

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Editorial

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3 pages, 186 KiB

Open AccessEditorial

Editorial to the Special Issue “Food Bioactives: Chemical Challenges and Bio-Opportunities”

by Severina Pacifico and Simona Piccolella

Molecules 2021, 26(9), 2517; https://doi.org/10.3390/molecules26092517 - 26 Apr 2021

Viewed by 1161

Abstract

This Special Issue, entitled “Food Bioactives: Chemical Challenges and Bio-Opportunities”, was born with the aim of attracting contributions on analytical challenges in food bioactives’ chemistry and bioactivity, which form the basis of proper bio-opportunities [...] Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

Research

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15 pages, 5405 KiB

Open AccessArticle

Evaluation of Hepatoprotective Activity and Oxidative Stress Reduction of Rosmarinus officinalis L. Shoots Tincture in Rats with Experimentally Induced Hepatotoxicity

by Irina Ielciu, Bogdan Sevastre, Neli-Kinga Olah, Andreea Turdean, Elisabeta Chișe, Raluca Marica, Ilioara Oniga, Alina Uifălean, Alexandra C. Sevastre-Berghian, Mihaela Niculae, Daniela Benedec and Daniela Hanganu

Molecules 2021, 26(6), 1737; https://doi.org/10.3390/molecules26061737 - 20 Mar 2021

Cited by 22 | Viewed by 3298

Abstract

Rosmarinus officinalis L. is a widely known species for its medicinal uses, that is also used as raw material for the food and cosmetic industry. The aim of the present study was to offer a novel perspective on the medicinal product originating from this species and to test its hepatoprotective activity. The tested sample consisted in a tincture obtained from the fresh young shoots. Compounds that are evaluated for this activity are polyphenols and terpenoids, that are identified and quantified by HPLC–UV–MS and GC–MS. Antioxidant activity was assessed in vitro, using the DPPH, FRAP and SO assays. Hepatoprotective activity was tested in rats with experimentally-induced hepatotoxicity. In the chemical composition of the tincture, phenolic diterpenes (carnosic acid, carnosol, rosmanol, rosmadial) and rosmarinic acid were found to be the majority compounds, alongside with 1,8-cineole, camphene, linalool, borneol and terpineol among monoterpenes. In vitro, the tested tincture proved significant antioxidant capacity. Results of the in vivo experiment showed that hepatoprotective activity is based on an antioxidant mechanism. In this way, the present study offers a novel perspective on the medicinal uses of the species, proving significant amounts of polyphenols and terpenes in the composition of the fresh young shoots tincture, that has proved hepatoprotective activity through an antioxidant mechanism. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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10 pages, 2029 KiB

Open AccessArticle

Evaluation of the Antibacterial Activity and Efflux Pump Reversal of Thymol and Carvacrol against Staphylococcus aureus and Their Toxicity in Drosophila melanogaster

by Zildene de Sousa Silveira, Nair Silva Macêdo, Joycy Francely Sampaio dos Santos, Thiago Sampaio de Freitas, Cristina Rodrigues dos Santos Barbosa, Dárcio Luiz de Sousa Júnior, Débora Feitosa Muniz, Lígia Claudia Castro de Oliveira, José Pinto Siqueira Júnior, Francisco Assis Bezerra da Cunha, Henrique Douglas Melo Coutinho, Valdir Queiroz Balbino and Natália Martins

Molecules 2020, 25(9), 2103; https://doi.org/10.3390/molecules25092103 - 30 Apr 2020

Cited by 27 | Viewed by 3885

Abstract

The antibacterial activity and efflux pump reversal of thymol and carvacrol were investigated against the Staphylococcus aureus IS-58 strain in this study, as well as their toxicity against Drosophila melanogaster. The minimum inhibitory concentration (MIC) was determined using the broth microdilution method, while efflux pump inhibition was assessed by reduction of the antibiotic and ethidium bromide (EtBr) MICs. D. melanogaster toxicity was tested using the fumigation method. Both thymol and carvacrol presented antibacterial activities with MICs of 72 and 256 µg/mL, respectively. The association between thymol and tetracycline demonstrated synergism, while the association between carvacrol and tetracycline presented antagonism. The compound and EtBr combinations did not differ from controls. Thymol and carvacrol toxicity against D. melanogaster were evidenced with EC₅₀ values of 17.96 and 16.97 µg/mL, respectively, with 48 h of exposure. In conclusion, the compounds presented promising antibacterial activity against the tested strain, although no efficacy was observed in terms of efflux pump inhibition. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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21 pages, 9949 KiB

Open AccessArticle

In Vitro and In Vivo Anticancer Activity of the Most Cytotoxic Fraction of Pistachio Hull Extract in Breast Cancer

by Maryam Seifaddinipour, Reyhaneh Farghadani, Farideh Namvar, Jamaludin Bin Mohamad and Nur Airina Muhamad

Molecules 2020, 25(8), 1776; https://doi.org/10.3390/molecules25081776 - 13 Apr 2020

Cited by 17 | Viewed by 4033

Abstract

Pistacia (Pistacia vera) hulls (PV) is a health product that has been determined to contain bioactive phytochemicals which have fundamental importance for biomedical use. In this study, PV ethyl acetate extraction (PV-EA) fractions were evaluated with the use of an MTT assay to find the most cytotoxic fraction, which was found to be F13b1/PV-EA. After that, HPTLC was used for identify the most active compounds. The antioxidant activity was analyzed with DPPH and ABTS tests. Apoptosis induction in MCF-7 cells by F13b1/PV-EA was validated via flow cytometry analysis and a distinctive nuclear staining method. The representation of genes like Caspase 3, Caspase 8, Bax, Bcl-2, CAT and SOD was assessed via a reverse transcription (RT_PCR) method. Inhabitation of Tubo breast cancer cell development was examined in the BALB-neuT mouse with histopathology observations. The most abundant active components available in our extract were gallic acid and the flavonoid quercetin. The F13b1/PV-EA has antiradical activity evidence by its inhibition of ABTS and DPPH free radicals. F13b1/PV-EA displayed against MCF-7 a suppressive effect with an IC₅₀ value of 15.2 ± 1.35 µg/mL. Also, the expression of CAT, SOD, Caspase 3, Caspase 8 and Bax increased and the expression of Bcl-2 decreased. F13b1/PV-EA dose-dependently inhibited tumor development in cancer-induced mice. Thus, this finding introduces F13b1/PV-EA as an effectual apoptosis and antitumor active agent against breast cancer. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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19 pages, 2404 KiB

Open AccessArticle

Study of the Quality Parameters and the Antioxidant Capacity for the FTIR-Chemometric Differentiation of Pistacia Vera Oils

by Lydia Valasi, Dimitra Arvanitaki, Angeliki Mitropoulou, Maria Georgiadou and Christos S. Pappas

Molecules 2020, 25(7), 1614; https://doi.org/10.3390/molecules25071614 - 01 Apr 2020

Cited by 11 | Viewed by 3098

Abstract

The aim of this work was to characterize the pistachio oil of the Greek variety, “Aegina”, evaluate its various quality indices, and investigate the potential use of FTIR as a tool to discriminate different oil qualities. For this purpose, the antioxidant capacity, the tocopherol content and the oxidation and degradation of fatty acids, as described by k, Δk, R-values, and free acidity were evaluated using 45 samples from eight different areas of production and two subsequent years of harvesting. The antioxidant capacity was estimated using 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid diammonium salt (ABTS) and 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazine (DPPH) assays, and the tocopherol content was quantified through HPLC analysis. FTIR spectra were recorded for all samples and multivariate analysis was applied. The results showed significant differences between the oil samples of different harvesting years, which were successfully discriminated by a representative FTIR spectral region based on R-value, total antioxidant capacity, and scavenging capacity, through ABTS. A similar approach could not be confirmed for the other quality parameters, such as the free acidity and the tocopherol content. This research highlighted the possibility of developing a simple, rapid, economic, and environment friendly method for the discrimination of pistachio oils according to their quality profile, through FTIR spectroscopy and multivariate analysis. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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25 pages, 3614 KiB

Open AccessArticle

Hempseed Lignanamides Rich-Fraction: Chemical Investigation and Cytotoxicity towards U-87 Glioblastoma Cells

by Ersilia Nigro, Giuseppina Crescente, Marialuisa Formato, Maria Tommasina Pecoraro, Marta Mallardo, Simona Piccolella, Aurora Daniele and Severina Pacifico

Molecules 2020, 25(5), 1049; https://doi.org/10.3390/molecules25051049 - 26 Feb 2020

Cited by 38 | Viewed by 4867

Abstract

The weak but noteworthy presence of (poly)phenols in hemp seeds has been long overshadowed by the essential polyunsaturated fatty acids and digestible proteins, considered responsible for their high nutritional benefits. Instead, lignanamides and their biosynthetic precursors, phenylamides, seem to display interesting and diverse biological activities only partially clarified in the last decades. Herein, negative mode HR-MS/MS techniques were applied to the chemical investigation of a (poly)phenol-rich fraction, obtained from hemp seeds after extraction/fractionation steps. This extract contained phenylpropanoid amides and their random oxidative coupling derivatives, lignanamides, which were the most abundant compounds and showed a high chemical diversity, deeply unraveled through high resolution tandem mass spectrometry (HR-MS/MS) tools. The effect of different doses of the lignanamides-rich extract (LnHS) on U-87 glioblastoma cell line and non-tumorigenic human fibroblasts was evaluated. Thus, cell proliferation, genomic DNA damage, colony forming and wound repair capabilities were assessed, as well as LnHS outcome on the expression levels of pro-inflammatory cytokines. LnHS significantly inhibited U-87 cancer cell proliferation, but not that of fibroblasts, and was able to reduce U-87 cell migration, inducing further DNA damage. No modification in cytokines’ expression level was found. Data acquired suggested that LnHS acted in U-87 cells by inducing the apoptosis machinery and suppressing the autophagic cell death. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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17 pages, 2361 KiB

Open AccessFeature PaperArticle

Simultaneous LC/MS Analysis of Carotenoids and Fat-Soluble Vitamins in Costa Rican Avocados (Persea americana Mill.)

by Carolina Cortés-Herrera, Andrea Chacón, Graciela Artavia and Fabio Granados-Chinchilla

Molecules 2019, 24(24), 4517; https://doi.org/10.3390/molecules24244517 - 10 Dec 2019

Cited by 18 | Viewed by 4717

Abstract

Avocado (a fruit that represents a billion-dollar industry) has become a relevant crop in global trade. The benefits of eating avocados have also been thoroughly described as they contain important nutrients needed to ensure biological functions. For example, avocados contain considerable amounts of vitamins and other phytonutrients, such as carotenoids (e.g., β-carotene), which are fat-soluble. Hence, there is a need to assess accurately these types of compounds. Herein we describe a method that chromatographically separates commercial standard solutions containing both fat-soluble vitamins (vitamin A acetate and palmitate, Vitamin D₂ and D₃, vitamin K₁, α-, δ-, and γ-vitamin E isomers) and carotenoids (β-cryptoxanthin, zeaxanthin, lutein, β-carotene, and lycopene) effectively (i.e., analytical recoveries ranging from 80.43% to 117.02%, for vitamins, and from 43.80% to 108.63%). We optimized saponification conditions and settled at 80 °C using 1 mmol KOH L⁻¹ ethanol during 1 h. We used a non-aqueous gradient that included methanol and methyl tert-butyl ether (starting at an 80:20 ratio) and a C₃₀ chromatographic column to achieve analyte separation (in less than 40 min) and applied this method to avocado, a fruit that characteristically contains both types of compounds. We obtained a method with good linearity at the mid to low range of the mg L⁻¹ (determination coefficients 0.9006–0.9964). To determine both types of compounds in avocado, we developed and validated for the simultaneous analysis of carotenoids and fat-soluble vitamins based on liquid chromatography and single quadrupole mass detection (LC/MS). From actual avocado samples, we found relevant concentrations for cholecalciferol (ranging from 103.5 to 119.5), δ-tocopherol (ranging from 6.16 to 42.48), and lutein (ranging from 6.41 to 15.13 mg/100 g dry weight basis). Simmonds cultivar demonstrated the higher values for all analytes (ranging from 0.03 (zeaxanthin) to 119.5 (cholecalciferol) mg/100 g dry weight basis). Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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14 pages, 1103 KiB

Open AccessArticle

Exposure of Human Gastric Cells to Oxidized Lipids Stimulates Pathways of Amino Acid Biosynthesis on a Genomic and Metabolomic Level

by Mathias Zaunschirm, Marc Pignitter, Antonio Kopic, Claudia Keßler, Christina Hochkogler, Nicole Kretschy, Mark Manuel Somoza and Veronika Somoza

Molecules 2019, 24(22), 4111; https://doi.org/10.3390/molecules24224111 - 14 Nov 2019

Cited by 7 | Viewed by 2578

Abstract

The Western diet is characterized by a high consumption of heat-treated fats and oils. During deep-frying processes, vegetable oils are subjected to high temperatures which result in the formation of lipid peroxidation products. Dietary intake of oxidized vegetable oils has been associated with various biological effects, whereas knowledge about the effects of structurally-characterized lipid peroxidation products and their possible absorption into the body is scarce. This study investigates the impact of linoleic acid, one of the most abundant polyunsaturated fatty acids in vegetable oils, and its primary and secondary peroxidation products, 13-HpODE and hexanal, on genomic and metabolomic pathways in human gastric cells (HGT-1) in culture. The genomic and metabolomic approach was preceded by an up-to-six-hour exposure study applying 100 µM of each test compound to the apical compartment in order to quantitate the compounds’ recovery at the basolateral side. Exposure of HGT-1 cells to either 100 µM linoleic acid or 100 µM 13-HpODE resulted in the formation of approximately 1 µM of the corresponding hydroxy fatty acid, 13-HODE, in the basolateral compartment, whereas a mean concentration of 0.20 ± 0.13 µM hexanal was quantitated after an equivalent application of 100 µM hexanal. An integrated genomic and metabolomic pathway analysis revealed an impact of the linoleic acid peroxidation products, 13-HpODE and hexanal, primarily on pathways related to amino acid biosynthesis (p < 0.05), indicating that peroxidation of linoleic acid plays an important role in the regulation of intracellular amino acid biosynthesis. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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16 pages, 4006 KiB

Open AccessArticle

UHPLC-HR-MS/MS-Guided Recovery of Bioactive Flavonol Compounds from Greco di Tufo Vine Leaves

by Simona Piccolella, Giuseppina Crescente, Maria Grazia Volpe, Marina Paolucci and Severina Pacifico

Molecules 2019, 24(19), 3630; https://doi.org/10.3390/molecules24193630 - 08 Oct 2019

Cited by 18 | Viewed by 3210

Abstract

Leaves of Vitis vinifera cv. Greco di Tufo, a precious waste made in the Campania Region (Italy), after vintage harvest, underwent reduction, lyophilization, and ultrasound-assisted maceration in ethanol. The alcoholic extract, as evidenced by a preliminary UHPLC-HR-MS analysis, showed a high metabolic complexity. Thus, the extract was fractionated, obtaining, among others, a fraction enriched in flavonol glycosides and glycuronides. Myricetin, quercetin, kaempferol, and isorhamnetin derivatives were tentatively identified based on their relative retention time and TOF-MS² data. As the localization of saccharidic moiety in glycuronide compounds proved to be difficult due to the lack of well-established fragmentation pattern and/or the absence of characteristic key fragments, to obtain useful MS information and to eliminate matrix effect redundancies, the isolation of the most abundant extract’s compound was achieved. HR-MS/MS spectra of the compound, quercetin-3-O-glucuronide, allowed us to thoroughly rationalize its fragmentation pattern, and to unravel the main differences between MS/MS behavior of flavonol glycosides and glycuronides. Furthermore, cytotoxicity assessment on the (poly)phenol rich fraction and the pure isolated compound was carried out using central nervous system cell lines. The chemoprotective effect of both the (poly)phenol fraction and quercetin-3-O-glucuronide was evaluated. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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20 pages, 1360 KiB

Open AccessArticle

In vitro Fermentation of Polysaccharides from Aloe vera and the Evaluation of Antioxidant Activity and Production of Short Chain Fatty Acids

by Antonio Tornero-Martínez, Rubén Cruz-Ortiz, María Eugenia Jaramillo-Flores, Perla Osorio-Díaz, Sandra Victoria Ávila-Reyes, Guadalupe Monserrat Alvarado-Jasso and Rosalva Mora-Escobedo

Molecules 2019, 24(19), 3605; https://doi.org/10.3390/molecules24193605 - 07 Oct 2019

Cited by 29 | Viewed by 6658

Abstract

Soluble or fermentable fibre has prebiotic effects that can be used in the food industry to modify the composition of microbiota species to benefit human health. Prebiotics mostly target Bifidobacterium and Lactobacillus strains, among others, which can fight against chronic diseases since colonic fermentation produces short chain fatty acids (SCFAs). The present work studied the changes produced in the fibre and polyphenolic compounds during in vitro digestion of gel (AV) and a polysaccharide extract (AP) from Aloe vera, after which, these fractions were subjected to in vitro colonic fermentation to evaluate the changes in antioxidant capacity and SCFAs production during the fermentation. The results showed that the phenolic compounds increased during digestion, but were reduced in fermentation, as a consequence, the antioxidant activity increased significantly in AV and AP after the digestion. On the other hand, during in vitro colon fermentation, the unfermented fibre of AV and AP responded as lactulose and the total volume of gas produced, which indicates the possible use of Aloe vera and polysaccharide extract as prebiotics. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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Review

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23 pages, 3171 KiB

Open AccessReview

Therapeutic Perspectives of Molecules from Urtica dioica Extracts for Cancer Treatment

by Sabrina Esposito, Alessandro Bianco, Rosita Russo, Antimo Di Maro, Carla Isernia and Paolo Vincenzo Pedone

Molecules 2019, 24(15), 2753; https://doi.org/10.3390/molecules24152753 - 29 Jul 2019

Cited by 51 | Viewed by 12089

Abstract

A large range of chronic and degenerative diseases can be prevented through the use of food products and food bioactives. This study reports the health benefits and biological activities of the Urtica dioica (U. dioica) edible plant, with particular focus on its cancer chemopreventive potential. Numerous studies have attempted to investigate the most efficient anti-cancer therapy with few side effects and high toxicity on cancer cells to overcome the chemoresistance of cancer cells and the adverse effects of current therapies. In this regard, natural products from edible plants have been assessed as sources of anti-cancer agents. In this article, we review current knowledge from studies that have examined the cytotoxic, anti-tumor and anti-metastatic effects of U. dioica plant on several human cancers. Special attention has been dedicated to the treatment of breast cancer, the most prevalent cancer among women and one of the main causes of death worldwide. The anti-proliferative and apoptotic effects of U. dioica have been demonstrated on different human cancers, investigating the properties of U. dioica at cellular and molecular levels. The potent cytotoxicity and anti-cancer activity of the U. dioica extracts are due to its bioactive natural products content, including polyphenols which reportedly possess anti-oxidant, anti-mutagenic and anti-proliferative properties. The efficacy of this edible plant to prevent or mitigate human cancers has been demonstrated in laboratory conditions as well as in experimental animal models, paving the way to the development of nutraceuticals for new anti-cancer therapies. Full article

(This article belongs to the Special Issue Food Bioactives: Chemical Challenges and Bio-Opportunities)

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