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This article belongs to the Special Issue Polyphenols in Plant-Based Foods: Effects of Food Processing on Their Content, Bioaccessibility, Bioavailability, and Bioactivity., In this study, chitosan particles were used to encapsulate marjoram phenolic compounds as colon-specific drug-delivery systems. The microparticles were prepared by ionic gelation and spray-drying techniques and varying amounts of polymer and extract, along with different method conditions. The spray drying of microparticles (0.75% low molecular weight chitosan dissolved in 0.4% of acetic acid) presented the best encapsulation efficiency (near 75%), with size ranges from 1.55 to 1.68 µm that allowed the encapsulation of 1.25–1.88 mg/mL of extract. Release studies of individual marjoram phenolic compounds at pH 2 and 7.4 showed that most of the compounds remained encapsulated in the microparticles. Only arbutin and vicenin II presented a high initial burst release. As the polarity of the compounds was reduced, their initial release decreased. In addition, after gastrointestinal digestion, most of marjoram phenolic compounds remained encapsulated. These results prove that chitosan microparticlescould protect the marjoram phenolic compounds during gastrointestinal digestion, specifically those related to anticancer activity, which enables their application as colon-specific delivery systems., This research was funded by the Spanish Government (Project: PID2019-110183RB-C22/AEI/10.13039/501100011033) and by Comunidad Autónoma de Madrid (ALIBIRD2020-CM, S2018/BAA-4343).

This article belongs to the Special Issue Phenolic Compounds in Herbs: Characterization, Antioxidant Properties and Health Benefits., Melissa officinalis L. and Origanum majorana L., within Lamiaceae family, and Calendula officinalis L. and Achillea millefolium L., within the Asteraceae, have been considered a good source of bioactive ingredients with health benefits. In this study, the supercritical fluid extraction (SFE) using pure CO2, and the ultrasound assisted extraction (UAE) were proposed as green techniques to obtain plant-based extracts with potential antioxidant and anti-inflammatory activities. Higher values of total phenolic content and antioxidant activity were achieved in UAE ethanol:water (50:50, v/v) extracts. Meanwhile, UAE pure ethanol extracts showed greater anti-inflammatory activity. RP-HPLC-PAD-ESI-QTOF-MS/MS analysis showed a vast number of phenolic compounds in the extracts, including unreported ones. O. majorana ethanol:water extract presented the highest content of phenolics and antioxidant activity; among its composition, both rosmarinic acid and luteolin glucoside derivatives were abundant. The pure ethanol extract of A. millefolium resulted in an important content of caffeoylquinic acid derivatives, luteolin-7-O-glucoside and flavonoid aglycones, which could be related to the remarkable inhibition of TNF-α, IL-1β and IL-6 cytokines. Besides, borneol and camphor, found in the volatile fraction of A. millefolium, could contributed to this latter activity. Thus, this study points out that O. majorana and A. millefolium are considered a promising source of bioactive ingredients with potential use in health promotion., Authors thanks to the Spanish Government (Project: PID2019-110183RB-C22/AEI/10.13039/501100011033) and Comunidad Autónoma de Madrid (ALIBIRD2020-CM (S2018/BAA-4343)) for financial support.

[Ethnopharmacological relevance] Marjoram (Origanum majorana L.) is an herb traditionally used as a medicine in different countries, as Morocco and Iran, because of its beneficial cardiovascular effects. Some studies suggest that these effects are due, at least in part, to the presence of phenolic compounds such as rosmarinic acid (RA) and luteolin., [Aim of the study] To analyze the possible cardiprotective effects of a marjoram extract (ME) reducing myocardial damage after coronary ischemia-reperfusion (IR) and its possible antihypertensive effects reducing the response of aorta segments to the vasoconstrictors noradrenaline (NA) and endothelin-1 (ET-1)., [Materials and methods] Male Wistar rats (300g) were used. After sacrifice, the heart was immediately removed and mounted in a perfusion system (Langendorff). The aorta was carefully dissected and cut in 2 mm segments to perform vascular reactivity experiments., [Results] In the heart, ME perfusion after IR reduced heart rate and prevented IR-induced decrease of cardiac contractility, possibly through vasodilation of coronary arteries and through the upregulation of antioxidant markers in the myocardium that led to reduced apoptosis of cardiomyocytes. In the aorta, ME decreased the vasoconstrictor response to NA and ET-1 and exerted a potent anti-inflammatory and antioxidant effect. Neither RA nor 6-hydroxi-luteolin-O-glucoside, major compounds of this ME, were effective in improving cardiac contractility after IR or attenuating vasoconstriction to NA and ET-1 in aorta segments., [Conclusion] In conclusion, ME reduces the myocardial damage induced by IR and the contractile response to vasoconstrictors in the aorta. Thus, it may be useful for the treatment of cardiovascular diseases such as myocardial infarction and hypertension., This study has been funded by Grants from Community of Madrid awarded to Daniel González-Hedström (IND2017/BIO7701) and María de la Fuente-Fernández (PEJ-2018-AI/SAL-11315).

To understand the interactions between carriers and functional ingredients is crucial when designing delivery systems, to maximize bioefficacy and functionality. In this study, two different protein matrices were evaluated as means to protect the extract isolated from marjoram leaves (Origanum majorana), casein micelles from fresh skim milk and soy protein isolate (SPI). RESULTS Marjoram extract was obtained from pressurization of ethanol and water solvent. Protein dispersions of casein and SPI (5?g?L?1 each) with or without marjoram extract (0.1?3?mg?mL?1) were prepared and homogenized. The physicochemical characterization of charge and entrapment efficiency were conducted. The results demonstrated that entrapment efficiency was highly dependent on the carrier itself where SPI formulations showed 20% higher affinity when compared to casein micelles. To investigate the physiological behaviour of the marjoram?protein dispersions, human macrophages were employed. A non-specific inflammatory response of macrophages stimulated with bacterial lipopolysaccharide was measured for TNF-α, IL-1? and IL-6 cytokine secretion. CONCLUSION Casein and SPI protein formulations warranted high bioefficacy of marjoram extract, showing their potential as safe carriers. ? 2018 Society of Chemical Industry

In this work the fractionation of an ethanolic extract of Achillea millefolium L. (yarrow) using supercritical carbon dioxide anti-solvent technique was studied, with the target of increasing the concentration of phenolic compounds in the precipitated fraction. The effect of pressure on the selective precipitation was analyzed, together with the morphology and particle size distribution of the precipitates. In the range of pressures studied (10–20 MPa), up to a 3 fold increase of the total phenolic compound concentration was observed in the precipitates in comparison with the ethanolic yarrow extract. In addition, the selective fractionation of the main phenolic compounds identified in the extract (3,5-dicaffeoylquinic acid, a glycoside form of apigenin and luteolin, as well as the aglycones) was analyzed. Particle sizes around 250–330 μm were produced with a nozzle of 101.6 μm inner diameter, due to the formation of aggregates. In this respect, increasing pressure from 10 to 15 MPa resulted in smaller particles, while further pressure increasing had no significant effect on particle size decrease., The authors gratefully acknowledge the financial support from Ministerio de Economía y Competitividad of Spain (project AGL2013-48943-C2) and the Comunidad Autónoma de Madrid (ALIBIRD, project number S2013/ABI-2728).

The aim of this study was to improve the stability and antioxidant activity of yarrow phenolic compounds upon an in vitro simulated gastrointestinal digestion. Therefore, two types of caseins-based delivery systems, sodium caseinate stabilized nanoemulsions (NEs) and glucono delta-lactone acidified milk gels (MGs), were formulated containing an ultrasound-assisted yarrow extract (YE) at two concentrations (1 and 2.5 mg/mL). Formulations with 1 mg/mL of YE were chosen based on their higher encapsulation efficiency to perform the in vitro digestion experiments. After digestion, YE-loaded NEs only partially protected phenolic compounds from degradation; meanwhile the phenolic composition of YE including in MGs after digestion was quite similar to undigested YE. Moreover, the antioxidant activity of MGs after digestion was higher than NEs digested samples, which confirms the higher protection of YE phenolic compound by the milk gels systems. This research demonstrated the potential use of acidified MGs as carriers to improve the stability and antioxidant activity of yarrow phenolic compounds. Therefore, these matrices could be employed to develop new dairy products enriched with phenolic compounds., This work was supported by Spanish Government (FORCHRONIC Project: ALG-2016-76736-C3-1-R), by Comunidad Autónoma de Madrid (ALIBIRD project: P2018/BAA-4343) and by the Natural Sciences and Engineering Council of Canada, through the Canada Research Chair programme.

Truffles, besides the appreciated aromatic compounds, contain other molecules with interesting bioactive properties. A screening of fungal sterols and β-glucans within different truffle species and locations was carried out. These compounds were extracted with pressurized liquids (PLE) generating enriched fractions. Extraction efficiency was studied with a full-factorial experimental design (Response surface methodology, RSM), using water and ethanol as extraction solvents. Polysaccharides from truffle powder (TP) and the optimal PLE extract (EP) obtained were precipitated and analysed by NMR and GC–MS. THP-1 cell cultures were utilized to test immunomodulatory properties. With the optimal PLE conditions (16.7 MPa, 180 °C, 30 min) 64 and 22.5% yields were obtained respect, with water and ethanol, generating fractions containing respect, 9.1% β-glucan and 4.5% ergosterol. NMR analyses detected (1 → 3)-β-glucan structures in truffle. The EP induced a reduction of 40% IL-1β and 60% IL-6 pro-inflammatory cytokines secretion suggesting potential immunomodulatory activity.

Achillea millefolium L. is a plant widely used in traditional medicine. Nowadays, there is a growing concern about the study of its bioactive properties in order to develop food and nutraceutical formulations. Supercritical anti-solvent fractionation (SAF) of an A. millefollium extract was carried out to improve its antioxidant and anti-inflammatory activities. A selective precipitation of phenolic compounds was achieved in the precipitation vessel fractions, which presented an antioxidant activity twice than original extract, especially when fractionation was carried out at 10 MPa. The main phenolic components identified in this fraction were luteolin-7-O-glucoside, 3,5-dicaffeoylquinic acid, 6-hidroxyluteolin-7-O-glucoside and apigenin-7-O-glucoside. However, separator fractions presented higher anti-inflammatory activity than precipitation vessel ones, particularly at 15 MPa. This fact could be related to separator fractions enrichment in anti-inflammatory compounds, mainly camphor, artemisia ketone and borneol. Therefore, SAF produced a concentration of antioxidant and anti-inflammatory compounds that could be used as high-added valued ingredients., This work was supported by Spanish Government (FORCHRONIC Project: AGL-2016-76736-C3-1-R) and Comunidad Autónoma de Madrid (ALIBIRD, project: P2013/ALI2728).

Innovative technologies as ultrasound-assisted extraction (UAE) (550 W, 60% amplitude, 50 °C) or subcritical water extraction (SWE) (200 °C, 11.7 MPa) were more effective than hot water extractions to obtain β-glucan-enriched fractions from shiitake mushrooms. UAE required longer extraction time (60 min) than SWE (15 min). Combination of UAE + SWE or pre-treatment of the raw material with supercritical CO2 (SFE) (40 °C, 35 MPa, 3 h) before both extractions yielded extracts containing larger β-glucan concentrations. Fluorimetric/colorimetric determinations indicated that obtained fractions contained (1 → 3)- and (1 → 3),(1 → 6)-β-glucans. NMR confirmed their presence as well as (1 → 3)-α-glucans and heteropolymers including mannose and galactose. SWE (15 min), SFE + SWE or UAE + SWE extracts showed larger glucose levels and lower mannose and galactose residues than the other extractions suggesting certain extraction specificity towards β-glucans. They also included more chitin-derivatives than UAE. The extracts obtained after combination of technologies partially retained their immunomodulatory properties but they showed high hypocholesterolemic activities according to in vitro studies., This research was supported by national R+ D program from the Spanish Ministry of Science and Innovation (project AGL2014-56211-R) and the regional program from the Community of Madrid, Spain (S2013/ABI-2728).

This article belongs to the Special Issue Advances in Supercritical Fluid Food Science and Technology., Heather (Calluna vulgaris L.) and marigold (Calendula officinalis L.) are two rich sources of bioactive pentacyclic triterpenes. The supercritical carbon dioxide (SCCO2) extraction of these two plants was explored at a pressure range of 25–50 MPa, 50 °C, with or without fractionation, different extraction times (1.5–4.0 h) and using ethanol as a co-solvent (0 and 10% w/w). In order to determine potential synergisms, a combined extraction (heather + marigold 50:50) was also studied. In general, higher extraction yields were achieved when the co-solvent was added. Higher concentrations of total triterpenic acids were obtained in heather extracts, specially using ethanol. The co-solvent did not increase the terpene concentration in marigold extracts. For the combined extraction, an antagonist effect in the triterpene concentration was observed in absence of a co-solvent, whereas a synergistic effect was exhibited in its presence, especially for ursolic acid. In general, the extracts showed a certain anti-inflammatory effect, although a straight correlation with the analyzed triterpenic acids concentration was not exhibited. Moreover, the combined extraction exposed a similar anti-inflammatory activity in comparison with the individual plant extracts., The authors gratefully acknowledge the financial support from Ministerio de Economía y Competitividad of Spain (project AGL2013-48943-C2) and the Comunidad Autónoma de Madrid (ALIBIRD, project number S2013/ABI-2728).

A polysaccharide-enriched extract obtained from Lentinula edodes was submitted to several purification steps to separate three different D-glucans with β-(1→6), β-(1→3),(1→6) and α-(1→3) linkages, being characterized through GC–MS, FT-IR, NMR, SEC and colorimetric/fluorimetric determinations. Moreover, in vitro hypocholesterolemic, antitumoral, anti-inflammatory and antioxidant activities were also tested. Isolated glucans exerted HMGCR inhibitory activity, but only β-(1→6) and β-(1→3),(1→6) fractions showed DPPH scavenging capacity. Glucans were also able to lower IL-1β and IL-6 secretion by LPS-activated THP-1/M cells and showed cytotoxic effect on a breast cancer cell line that was not observed on normal breast cells. These in vitro results pointed important directions for further in vivo studies, showing different effects of each chemical structure of the isolated glucans from shiitake mushrooms., This research was supported by national R + D program from the Spanish Ministry of Science and Innovation (Project AGL2014-56211-R) and the regional program from the Community of Madrid, Spain (S2013/ABI-2728). Part of this study was also financed by the Brazilian funding agencies Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) – Finance Code 001 and the Fundação Araucária.

To understand the interactions between carriers and functional ingredients is crucial when designing delivery systems, to maximize bioefficacy and functionality. In this study, two different protein matrices were evaluated as means to protect the extract isolated from marjoram leaves (Origanum majorana), casein micelles from fresh skim milk and soy protein isolate (SPI).Marjoram extract was obtained from pressurization of ethanol and water solvent. Protein dispersions of casein and SPI (5 g LCasein and SPI protein formulations warranted high bioefficacy of marjoram extract, showing their potential as safe carriers. © 2018 Society of Chemical Industry.

The potential use of Origanum majorana L. as a source of bioavailable phenolic compounds, specifically rosmarinic acid (RA), has been evaluated. Phenolic bioavailability was tested using an in vitro digestion process followed by a Caco-2 cellular model of intestinal absorption. The high-performance liquid chromatography-photodiode array detector-tandem mass spectrometry (HPLC-PAD-MS/MS) analysis showed the main components in the extract were 6-hydroxyluteolin-7-O-glucoside and rosmarinic acid, followed by luteolin-O-glucoside. After digestion process, the amount of total phenolic compounds (TPC) only decreased slightly, although a remarkable reduction in RA (near 50%) was detected. Bioavailable fraction contained 7.37 ± 1.39 mg/L digested extract of RA with small quantities of lithospermic acid and diosmin and presented an important antioxidant activity (0.89 ± 0.09 mmol Trolox/L digested extract). Besides, this bioavailable fraction produced a significant inhibition in TNF-α, IL-1β, and IL-6 secretion, using a human THP-1 macrophages model. Therefore, RA content in the basolateral compartment could play an important role in the antioxidant and anti-inflammatory activities found., Financial support was received from the Spanish Government (FORCHRONIC Project AGL-2016-76736-C3-1-R) and Comunidad Autonoma de Madrid (ALIBIRD, Project P2013/ABI2728).

Whey proteins can exhibit antioxidant activity. The objectives of this study were to formulate model whey based beverages with well-established antioxidants (plant polyphenols, vitamins and astaxanthin) to investigate (1) the antioxidant shelf life over a 24-week period and (2) the antioxidant activity after upper gastrointestinal transit. Pilot scale processing (pasteurization, ultra-high temperature or spray drying) was used to prepare beverages which were representative of current product formats. In vitro gastrointestinal digestion of test samples was performed using the standardised INFOGEST method and antioxidant activity of samples was determined using ABTS, FRAP and ORAC. Results from the antioxidant shelf life study provided evidence that powder products functionality was preserved. Whey beverages (pasteurised or spray dried) increased or maintained antioxidant activity during gastrointestinal transit. Combination of whey with additional antioxidant ingredients increased the bioactivity of formulated products; however, this greater bioactivity was altered after gastrointestinal transit, depending on processing type and antioxidant methodology., This work was funded by the Irish Department of Agriculture, Food and the Marine, FIRM 13F354-WheyGSH and 15F604-TOMI). A. R. Corrochano was in receipt of a Teagasc Walsh Fellowship. E. Arranz also received funding from Enterprise Ireland (MF2018-0151) and the European Union's Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 713654.

Taking into account the bioactive and healthy properties of alkylglycerols (AKG) and the antioxidant rosemary extract (RE), the production of a cooked meat product with partial replacement of animal fat by AKG-rich oil and inclusion of RE was performed. Six batches were manufactured: Control, control + RE (0.045%RE); low-AKG (0.75%AKG-oil), low-AKG + RE (0.75%AKG-oil + 0.045%RE); high-AKG (4.3%AKG-oil) and high-AKG + RE (4.3%AKG-oil + 0.045%RE). Fatty acid and lipid profile, changes on lipid oxidation (TBARS), antioxidant ability (TEAC), and carnosic acid were determined during refrigerated storage (0, 30, 60 days). A relevant replacement of animal fat by AKG-rich oil was obtained (around 20% for the high-AKG samples), together with healthier indexes of the fatty acid profile. A slight trend to worse lipid oxidation due to addition of AKG-rich oil was measured, but being only significantly higher for the high-AKG treatment in absence of RE. A significant better stability was measured due to inclusion of RE for all the treatments. Therefore, the oxidation of both low-AKG + RE and high-AKG + RE treatments were significantly comparable to the control batch. After storage, TBARS values increased for all the batches. Samples containing RE showed better TEAC values after the storage. In agreement, the amount of carnosic acid kept constant during the self-life of the products., This work was supported by the Ministerio de Economía y Competitividad, Spain (AGL2013-48943-C2-1-R) and the Community of Madrid, Spain (ALIBIRD-CM S2013/ABI2728). L Salas-Perez thanks CONACYT (Mexico) for her postdoctoral contract.