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Natural and Synthetic Phenolic Compounds for Food Applications

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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 (31 January 2022) | Viewed by 55358

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Prof. Dr. Lucia Panzella

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Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
Interests: phenolic compounds; food packaging; agri-food wastes; antioxidants; antinitrosating agents; biomaterials; melanin pigments; sustainability
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Dear Colleagues,

Thanks to their potent antioxidant as well as antimicrobial properties, natural phenolic compounds have gained more and more attention for their possible exploitation, not only as food supplements but also in the food industry, e.g., as active components in food packaging for food stabilization.

This Special Issue is dedicated to natural and synthetic phenolic compounds endowed with antioxidant and other food-stabilization-related properties for potential application in the food industry. Original research articles dealing with innovative applications of natural phenolic compounds as additives in smart food packaging are welcome. In the case of plant-derived extracts, structural characterization and identification of the main active components is required. Manuscripts describing the modulation of the solubility and/or of the antioxidant and other food relevant properties of natural phenolic compounds to broaden their applications are also welcome, although safety aspects should be carefully considered in this case. Attention will be devoted also to green and sustainable approaches for the recovery of antioxidant and antimicrobial compounds from natural sources, as well as to bioprocessing and green chemistry solutions to improve their properties. Review articles describing the current state-of-the-art are also welcome.

Prof. Dr. Lucia Panzella
Guest Editor

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Keywords

Phenolic compounds
Antioxidant
Antimicrobial
Food packaging
Sustainability
Green chemistry
Bioprocessing

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Published Papers (11 papers)

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Research

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17 pages, 15648 KiB

Open AccessArticle

Coffee-Derived Phenolic Compounds Activate Nrf2 Antioxidant Pathway in I/R Injury In Vitro Model: A Nutritional Approach Preventing Age Related-Damages

by Elena Lonati, Tatiana Carrozzini, Ilaria Bruni, Pedro Mena, Laura Botto, Emanuela Cazzaniga, Daniele Del Rio, Massimo Labra, Paola Palestini and Alessandra Bulbarelli

Molecules 2022, 27(3), 1049; https://doi.org/10.3390/molecules27031049 - 3 Feb 2022

Cited by 16 | Viewed by 3309

Abstract

Age-related injuries are often connected to alterations in redox homeostasis. The imbalance between free radical oxygen species and endogenous antioxidants defenses could be associated with a growing risk of transient ischemic attack and stroke. In this context, a daily supply of dietary antioxidants could counteract oxidative stress occurring during ischemia/reperfusion injury (I/R), preventing brain damage. Here we investigated the potential antioxidant properties of coffee-derived circulating metabolites and a coffee pulp phytoextract, testing their efficacy as ROS scavengers in an in vitro model of ischemia. Indeed, the coffee fruit is an important source of phenolic compounds, such as chlorogenic acids, present both in the brewed seed and in the discarded pulp. Therefore, rat brain endothelial cells, subjected to oxygen and glucose deprivation (OGD) and recovery (ogR) to mimic reperfusion, were pretreated or not with coffee by-products. The results indicate that, under OGD/ogR, the ROS accumulation was reduced by coffee by-product. Additionally, the coffee extract activated the Nrf2 antioxidant pathway via Erk and Akt kinases phosphorylation, as shown by increased Nrf2 and HO-1 protein levels. The data indicate that the daily intake of coffee by-products as a dietary food supplement represents a potential nutritional strategy to counteract aging. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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13 pages, 323 KiB

Open AccessArticle

Screening of Plant Pollen Sources, Polyphenolic Compounds, Fatty Acids and Antioxidant/Antimicrobial Activity from Bee Pollen

by Yusuf Can Gercek, Saffet Celik and Sinan Bayram

Molecules 2022, 27(1), 117; https://doi.org/10.3390/molecules27010117 - 26 Dec 2021

Cited by 34 | Viewed by 6090

Abstract

In this study, the botanical origin, total flavonoid and phenolic content, antioxidant activity, phenolic profile and fatty acid composition of mixed bee pollen loads collected in Bayburt, Turkey, were determined. In addition to these assays, antibacterial activity of bee-collected pollen extract (BCPE) against a variety of food-borne pathogenic bacteria was determined in vitro. Pollen loads were classified into five botanical families based on their color: Asteraceae, Fabaceae, Campanulaceae, Cistaceae and Rosaceae. Total flavonoid, total phenolic, CUPRAC and CERAC concentrations were 173.52 mg GAE/g, 79.21 mg QE/g, 85.59 mg Trolox/g and 118.13 mg Trolox/g, respectively. Twenty-three phenolic compounds were scanned in bee pollen extract by LC-MS/MS, with rutin being the most abundant. Cis-4,7,10,13,16,19 docosahexaenoic acid was the predominant fatty acid, followed by cis-11-eicosenoic acid, palmitic acid, and alfa linolenic acid. In addition, the agar well diffusion (AWD) and micro-broth dilution methods were used to determine of the antibacterial activity of the BCPE sample. MIC values were observed to vary between 2.5–5 mg/mL for Gram-positive bacteria and 5–10 mg/mL for Gram-negative bacteria. These findings indicate that bee pollen could be a potential source of antioxidants and antimicrobials. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

12 pages, 622 KiB

Open AccessArticle

Anthocyanin Profile, Antioxidant, Anti-Inflammatory, and Antimicrobial against Foodborne Pathogens Activities of Purple Rice Cultivars in Northern Thailand

by Thanawat Pattananandecha, Sutasinee Apichai, Sasithorn Sirilun, Jakaphun Julsrigival, Kasirawat Sawangrat, Fumihiko Ogata, Naohito Kawasaki, Busaban Sirithunyalug and Chalermpong Saenjum

Molecules 2021, 26(17), 5234; https://doi.org/10.3390/molecules26175234 - 29 Aug 2021

Cited by 21 | Viewed by 4623

Abstract

Five glutinous purple rice cultivars and non-glutinous purple rice cultivated in different altitudes in the north of Thailand were collected. The samples were extracted using ethanol and determined for anthocyanins using HPLC. The total phenolic content (TPC), total flavonoid content (TFC), and the antioxidant, anti-inflammatory, and antimicrobial activities against foodborne pathogens were investigated. The highland glutinous cultivar named Khao’ Gam Luem-Phua (KGLP) extract had significantly high levels of cyanidin 3-O-glucoside, peonidin 3-O-glucoside, delphinidin 3-O-glucoside, TPC, and TFC, as well as exerting a potent antioxidant activity through ABTS assay (524.26 ± 4.63 VCEAC, mg l-ascorbic-ascorbic/g extract), lipid peroxidation (IC₅₀ = 19.70 ± 0.31 µg/mL), superoxide anions (IC₅₀ = 11.20 ± 0.25 µg/mL), nitric oxide (IC₅₀ = 17.12 ± 0.56 µg/mL), a suppression effect on nitric oxide (IC₅₀ = 18.32 ± 0.82 µg/mL), and an inducible nitric oxide synthase production (IC₅₀ = 23.43 ± 1.21 µg/mL) in combined lipopolysaccharide-interferon-γ-activated RAW 264.7 murine macrophage cells. Additionally, KGLP also exhibited antimicrobial activity against foodborne pathogens, Staphylococcus aureus, Escherichia coli, Salmonella Enteritidis, and Vibrio parahaemolyticus. These results indicate that Thai glutinous purple rice cultivated on the highland could be a potent natural source of antioxidants, anti-inflammatories, and antimicrobial agents for use as a natural active pharmaceutical ingredient in functional food and nutraceutical products. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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15 pages, 1600 KiB

Open AccessArticle

Absorption Coefficients of Phenolic Structures in Different Solvents Routinely Used for Experiments

by Julia A. H. Kaeswurm, Andreas Scharinger, Jan Teipel and Maria Buchweitz

Molecules 2021, 26(15), 4656; https://doi.org/10.3390/molecules26154656 - 31 Jul 2021

Cited by 27 | Viewed by 6147

Abstract

Phenolic structures are of great interest due to their antioxidant properties and various postulated benefits on human health. However, the quantification of these structures in fruits and vegetables, as well as in vivo or in vitro experiments, is demanding, as relevant concentrations are often low, causing problems in exactly weighing the respective amounts. Nevertheless, the determination of used concentrations is often a prerequisite for accurate results. A possibility to quantify polyphenol is the use of UV/vis spectroscopy. Therefore, the absorption coefficients of selected phenolic structures were determined in three different solvents relevant for polyphenol research (water/methanol (50/50, v/v), water, and phosphate buffer at pH 7.5). To confirm the values based on weight and to avoid errors due to impurities, hygroscopic effects, and inadequate balance care, the mass concentrations were additionally determined by quantitative NMR (q-NMR). The coefficients presented in this article can help to quickly and easily determine accurate concentrations in a laboratory routine without wasting the often-precious standard compounds. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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14 pages, 1997 KiB

Open AccessArticle

Effects of Green Tea Powder, Pomegranate Peel Powder, Epicatechin and Punicalagin Additives on Antimicrobial, Antioxidant Potential and Quality Properties of Raw Meatballs

by Tuğba Demir

Molecules 2021, 26(13), 4052; https://doi.org/10.3390/molecules26134052 - 2 Jul 2021

Cited by 9 | Viewed by 3731

Abstract

Alternative technologies, which have been developed in order to meet the consumers’ demand for nourishing and healthy meat and meat products, are followed by the food industry. In the present study, it was determined, using the HPLC method, that green tea contains a high level of epicatechin (EP) under optimal conditions and that pomegranate peel contains a high level of punicalagin (PN). Green tea, pomegranate peel, EP and PN were added to meatballs at different concentrations in eight groups. The antioxidant capacities of extracts were measured. The antimicrobial activity was examined for 72 h using three different food pathogens. The highest level of antimicrobial activity was achieved in the 1% punicalagin group, whereas the minimum inhibition concentration (L. monocytogenes, S. typhimurium) was found to be 1.87 mg/mL. A statistically significant decrease was found in FFA, POV and TBARS levels of meatballs on different days of storage (p < 0.05). When compared to the control group, the bioactive compounds preserved the microbiological and chemical properties of meatballs during storage at +4 °C (14 days). It was concluded that the extracts with high EP and PN concentrations can be used as bio-preservative agents for meat and meat products. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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15 pages, 1452 KiB

Open AccessArticle

Dependence of the Ripeness Stage on the Antioxidant and Antimicrobial Properties of Walnut (Juglans regia L.) Green Husk Extracts from Industrial By-Products

by Daniela Soto-Madrid, Marlen Gutiérrez-Cutiño, Josué Pozo-Martínez, María Carolina Zúñiga-López, Claudio Olea-Azar and Silvia Matiacevich

Molecules 2021, 26(10), 2878; https://doi.org/10.3390/molecules26102878 - 13 May 2021

Cited by 19 | Viewed by 3421

Abstract

Walnut green husk (WGH) is a waste generated by the walnut (Juglans regia L.) harvest industry. It represents a natural source of polyphenols, compounds with antioxidant and antimicrobial activities, but their activity could be dependent on the ripeness stage of the raw material. In this study, the effect of the different ripeness stages—open (OH) and closed (CH) husks—on the antioxidant and antimicrobial properties of WGH extracts were analyzed, emphasizing the influence of the extracts in inhibiting Escherichia coli growth. The ripeness stage of WGH significantly affected the antioxidant activity of the extracts. This was attributed to the different polyphenol profiles related to the mechanical stress when the husk opened compared to the closed sample. The antimicrobial activity showed inhibition of E. coli growth. OH-extracts at 96 µg/mL caused the lowest specific growth rate (µ_max = 0.003 h⁻¹) and the greatest inhibition percentage (I = 93%) compared to CH-extract (µ_max = 0.01 h⁻¹; I = 69%). The obtained results showed the potential of the walnut green husk, principally open husk, as an economical source of antioxidant and antimicrobial agents with potential use in the food industry. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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14 pages, 1305 KiB

Open AccessFeature PaperArticle

Dragon Fruits as a Reservoir of Natural Polyphenolics with Chemopreventive Properties

by Paweł Paśko, Agnieszka Galanty, Paweł Zagrodzki, Patraporn Luksirikul, Dinorah Barasch, Alina Nemirovski and Shela Gorinstein

Molecules 2021, 26(8), 2158; https://doi.org/10.3390/molecules26082158 - 9 Apr 2021

Cited by 31 | Viewed by 6339

Abstract

Dragon fruits are a valued source of bioactive compounds with high potential to become a functional food. The aim of the study was to evaluate and compare the chemopreventive potential and chemical composition of fruits harvested in Thailand and Israel. The amount of different compounds in water and methanol extracts and antioxidant activity was investigated. Moreover, cytotoxic activity against cancer and normal cells of skin, prostate, and gastrointestinal origin was performed, accompanied by anti-inflammatory assay based on NO production in RAW 264.7 macrophage model. Additionally, the quenching properties of polyphenols from fruits were determined by the interaction of the main drug carrier in blood human serum (HSA). The chemometric analysis was used to reveal the relationships between the determined parameters. Dragon fruits harvested in Israel revealed higher antioxidant properties and total content of polyphenols and betacyanins when compared to those from Thailand. The examined fruits of both origins showed significant cytotoxic activity toward colon and prostate cancer cells, with no toxic effect on normal cells, but also no anti-inflammatory effect. Moreover, a high binding ability to HSA was observed for water extracts of dragon fruits. All these predestine dragon fruits are the candidates for the attractive and chemopreventive elements of daily diet. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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20 pages, 6490 KiB

Open AccessFeature PaperArticle

Hydroxytyrosol and Oleuropein-Enriched Extracts Obtained from Olive Oil Wastes and By-Products as Active Antioxidant Ingredients for Poly (Vinyl Alcohol)-Based Films

by Francesca Luzi, Elisa Pannucci, Mariangela Clemente, Edoardo Grande, Silvia Urciuoli, Annalisa Romani, Luigi Torre, Debora Puglia, Roberta Bernini and Luca Santi

Molecules 2021, 26(7), 2104; https://doi.org/10.3390/molecules26072104 - 6 Apr 2021

Cited by 30 | Viewed by 4653

Abstract

Oxidative stability of food is one of the most important parameters affecting integrity and consequently nutritional properties of dietary constituents. Antioxidants are widely used to avoid deterioration during transformation, packaging, and storage of food. In this paper, novel poly (vinyl alcohol) (PVA)-based films were prepared by solvent casting method adding an hydroxytyrosol-enriched extract (HTyrE) or an oleuropein-enriched extract (OleE) in different percentages (5, 10 and 20% w/w) and a combination of both at 5% w/w. Both extracts were obtained from olive oil wastes and by-products using a sustainable process based on membrane technologies. Qualitative and quantitative analysis of each sample carried out by high performance liquid chromatography (HPLC) and nuclear resonance magnetic spectroscopy (NMR) proved that the main components were hydroxytyrosol (HTyr) and oleuropein (Ole), respectively, two well-known antioxidant bioactive compounds found in Olea europaea L. All novel formulations were characterized investigating their morphological, optical and antioxidant properties. The promising performances suggest a potential use in active food packaging to preserve oxidative-sensitive food products. Moreover, this research represents a valuable example of reuse and valorization of agro-industrial wastes and by-products according to the circular economy model. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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14 pages, 285 KiB

Open AccessArticle

Effect of Elicitation with Iron Chelate and Sodium Metasilicate on Phenolic Compounds in Legume Sprouts

by Henryk Dębski, Wiesław Wiczkowski and Marcin Horbowicz

Molecules 2021, 26(5), 1345; https://doi.org/10.3390/molecules26051345 - 3 Mar 2021

Cited by 10 | Viewed by 2587

Abstract

Seven-day-old sprouts of fenugreek (Trigonella foenum-graecum L.), lentil (Lens culinaris L.), and alfalfa (Medicagosativa L.) were studied. The legume seeds and then sprouts were soaked each day for 30 min during 6 days with water (control) or mixture of Fe-EDTA and sodium silicate (Optysil), or sodium silicate (Na-Sil) alone. Germination and sprout growing was carried out at temperature 20 ± 2 °C in 16/8 h (day/night) conditions. Phenolic compounds (free, ester, and glycosides) content were determined by HPLC-ESI-MS/MS using a multiple reaction monitoring of selected ions. Flavonoids and phenolic acids were released from their esters after acid hydrolysis and from glycosides by alkaline hydrolysis. The presence and high content of (−)-epicatechin (EC) in fenugreek sprouts was demonstrated for the first time. Applied elicitors decreased the level of free EC in fenugreek and alfalfa sprouts but enhanced the content of its esters. Besides, elicitors decreased the content of quercetin glycosides in lentil and fenugreek sprouts but increased the content of quercetin and apigenin glycosides in alfalfa sprouts. The applied elicitors decreased the glycoside levels of most phenolic acids in lentil and p-hydroxybenzoic acid in fenugreek, while they increased the content of this acid in alfalfa. The mixture of iron chelate and sodium silicate had less effect on changes in flavonoid and phenolic acid content in legume sprouts than silicate alone. In general, the used elicitors increased the content of total phenolic compounds in fenugreek and alfalfa sprouts and decreased the content in lentil sprouts. Among the evaluated elicitors, Optysil seems to be worth recommending due to the presence of iron chelate, which can be used to enrich sprouts with this element. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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Review

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14 pages, 310 KiB

Open AccessReview

Natural Polyphenols for the Preservation of Meat and Dairy Products

by Hammad Ullah, Yaseen Hussain, Cristina Santarcangelo, Alessandra Baldi, Alessandro Di Minno, Haroon Khan, Jianbo Xiao and Maria Daglia

Molecules 2022, 27(6), 1906; https://doi.org/10.3390/molecules27061906 - 15 Mar 2022

Cited by 33 | Viewed by 6037

Abstract

Food spoilage makes foods undesirable and unacceptable for human use. The preservation of food is essential for human survival, and different techniques were initially used to limit the growth of spoiling microbes, e.g., drying, heating, salting, or fermentation. Water activity, temperature, redox potential, preservatives, and competitive microorganisms are the most important approaches used in the preservation of food products. Preservative agents are generally classified into antimicrobial, antioxidant, and anti-browning agents. On the other hand, artificial preservatives (sorbate, sulfite, or nitrite) may cause serious health hazards such as hypersensitivity, asthma, neurological damage, hyperactivity, and cancer. Thus, consumers prefer natural food preservatives to synthetic ones, as they are considered safer. Polyphenols have potential uses as biopreservatives in the food industry, because their antimicrobial and antioxidant activities can increase the storage life of food products. The antioxidant capacity of polyphenols is mainly due to the inhibition of free radical formation. Moreover, the antimicrobial activity of plants and herbs is mainly attributed to the presence of phenolic compounds. Thus, incorporation of botanical extracts rich in polyphenols in perishable foods can be considered since no pure polyphenolic compounds are authorized as food preservatives. However, individual polyphenols can be screened in this regard. In conclusion, this review highlights the use of phenolic compounds or botanical extracts rich in polyphenols as preservative agents with special reference to meat and dairy products. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

39 pages, 1314 KiB

Open AccessReview

Anthocyanins Recovered from Agri-Food By-Products Using Innovative Processes: Trends, Challenges, and Perspectives for Their Application in Food Systems

by Henrique Silvano Arruda, Eric Keven Silva, Nayara Macêdo Peixoto Araujo, Gustavo Araujo Pereira, Glaucia Maria Pastore and Mario Roberto Marostica Junior

Molecules 2021, 26(9), 2632; https://doi.org/10.3390/molecules26092632 - 30 Apr 2021

Cited by 46 | Viewed by 6133

Abstract

Anthocyanins are naturally occurring phytochemicals that have attracted growing interest from consumers and the food industry due to their multiple biological properties and technological applications. Nevertheless, conventional extraction techniques based on thermal technologies can compromise both the recovery and stability of anthocyanins, reducing their global yield and/or limiting their application in food systems. The current review provides an overview of the main innovative processes (e.g., pulsed electric field, microwave, and ultrasound) used to recover anthocyanins from agri-food waste/by-products and the mechanisms involved in anthocyanin extraction and their impacts on the stability of these compounds. Moreover, trends and perspectives of anthocyanins’ applications in food systems, such as antioxidants, natural colorants, preservatives, and active and smart packaging components, are addressed. Challenges behind anthocyanin implementation in food systems are displayed and potential solutions to overcome these drawbacks are proposed. Full article

(This article belongs to the Special Issue Natural and Synthetic Phenolic Compounds for Food Applications)

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