Aluminium is a ubiquitous element that occurs naturally in the soil making human exposure to it is unavoidable. Tyrosol is present in olive oil and is known to have antioxidant effects. Therefore, the present study explores the toxic effects of aluminium chloride (AlCl₃ ) and evaluates the possible protection by tyrosol in male rats. Testicular injury was induced by the administration of AlCl₃ (34 mg kg^-1 day^-1 ). Rats were treated with either tyrosol (20 mg kg^-1 day^-1 ) or AlCl3 (34 mg kg^-1 day^-1 ). The experiment lasted for 10 weeks. Biochemical, histopathological and protein expression profiles were determined to decipher the role of tyrosol in protecting the cellular damage. Further, histomorphometric analyses of testes showed deranged architecture along with other noted abnormalities. AlCl₃ group rats' testes showed decreased GSH levels, CAT activities, Nrf-2, HO-1, bcl-2 expressions and sperm motility whereas increased caspase-3 expressions, MDA levels, abnormal and dead/live sperm ratio. However, tyrosol treatment attenuated these changes. The present results demonstrate the beneficial role of tyrosol treatment in AlCl₃ induced testicular toxicity alterations of rat.

An RRLC method capable of simultaneous identification and rapid quantification of six biologically active compounds (salidroside, tyrosol, rosarin, rosavin, rosin, rosiridin) in Rhodiola rosea L. and two active compounds (eleutheroside B and eleutheroside E) in Eleutherococcus senticosus Maxim. was developed. The chromatographic analyses were performed on a reversed phase Phenomenex C18 (2)-HST column at 40°C with a neutral mobile phase (purified water and acetonitrile) gradient system at a flow rate of 1.0ml/min and UV detection at 205 and 220nm simultaneously. Baseline separation of eight active compounds was achieved within 8min. This developed method provides good linearity (R>0.9997), precision (RSD<1.99%) and recovery of the bioactive compounds. The RRLC method developed is capable of controlling the quality of R. rosea and E. senticosus raw herbs, commercial extracts, as well as polyherbal formulations containing R. rosea and E. senticosus as ingredients. This RRLC method is accurate and sensitive; in addition, it greatly increases sample analysis throughput with reduced analysis time, which is suitable for routine quality control analysis.

Rhodiola rosea (rose root) belonging to the family Crassulaceae is a popular medicinal plant in Russia, Scandinavia, and many other countries. Extracts of the roots of this plant have been found to favorably affect a number of physiological functions including neurotransmitter levels, central nervous system activity, and cardiovascular function. It is being used to stimulate the nervous system, decrease depression, enhance work performance, eliminate fatigue, and prevent high-altitude sickness. Most of these effects have been ascribed to constituents such as salidroside (rhodioloside), rosavins, and p-tyrosol. It has also been found to be a strong antioxidant and anticarcinogen due to the presence of several phenolic compounds. Adaptogens are plant extracts that allow an organism to counteract adverse physical, chemical, and biological stressors by generating nonspecific resistance. Adaptogens are known to increase the availability of energy during the day, reduce stressed feelings, increase endurance, and increase mental alertness. This multipurpose medicinal plant (R. rosea), with adaptogenic properties that increase the body's nonspecific resistance and normalize functions, has been traditionally grown and used in Russia and Mongolia. Due to increasing consumer demands toward natural health products and the growing interests in the secondary metabolites of plants and their application in biotechnology and therapy, much focus has been put on the rose root and its medical properties. The rose root imparts normalizing influences on adverse physical, chemical, and biological disturbances but is otherwise innocuous. In India, the plant has been growing wild in the high altitudes of the Himalayas. The Defence Research and Development Organization in India has taken on the responsibilities of its conservation, as well as the development of multiple management practices and the development of health foods, supplements, and nutraceuticals in India.

Environmentally friendly natural deep eutectic solvents (NADES) have been shown to efficiently extract a wide range of phenolic compounds from virgin olive oil (VOO). The objective of this work was to optimize the yield of olive oil phenols extracted by NADES based on xylitol/choline choride (Xyl/ChCl). Different extraction and recovery conditions were investigated, including the effect of different extraction operating parameters (temperature, time, VOO:NADES ratio) and subsequent recovery conditions (XAD resin height, wash-water and eluent volume and pH). The highest concentration of phenols (555.36 mg/kg VOO) was obtained from extraction at 40 °C for 1 h, with a 1:1 ratio, using an adsorption resin XAD-16 with bed height of 10 cm, 250 mL acidified wash-water and 300 mL EtOH 100% as eluent. No statistically significant loss of the sum of phenolic compounds was observed when compared with the concentration values obtained by direct analysis in HPLC without the elimination of NADES. Additionally, a sequential desorption with different concentration of ethanol was used to determine the effect of the solvent concentration on polyphenol yield. Polar compounds, such as hydroxytyrosol and tyrosol, were recovered at 81.7% and 83.6%, respectively with 50 and 80% ethanol; however, 100% ethanol was required for the complete elution of oleacein (3,4-DHPEA-EDA) and oleocanthal (p-HPEA-EDA). In this paper we present an effective process for the extraction of polyphenols from VOO by NADES for direct analysis in HPLC and for the recovery and concentration of polyphenols by removing the solvent (NADES) with no losses of yield and solvent recycling.

Keywords: Extraction; Natural deep eutectic solvent; Phenolic compounds; Recovery; Virgin olive oil.

We formulated and characterised two alginate blends for the encapsulation of stevia extract (SE) via ionic gelation through an extrusion technique. Calcium chloride in SE and calcium chloride solutions were assessed as crosslinkers to overcome phenolic losses by diffusion and increase encapsulation efficiency (EE). Regardless of the blend, all stevia-loaded beads exhibited high EE (62.7-101.0%). The size of the beads decreased as EE increased. Fourier transform infrared analysis showed increased hydrogen bonding between SE and alginates, confirming the successful incorporation of SE within the matrix. Untargeted metabolomics profiling identified 479 free and encapsulated polyphenolic compounds. Flavonoids (catechin and luteolin equivalents) were predominant in SE whereas tyrosols and 5-pentadecylresorcinol equivalents were predominant in all bead formulations. Three-common discriminant compounds were exclusive to each blend and were inversely affected by the crosslinking conditions. Both alginate blends have been shown to be feasible as carrier systems of stevia extracts independent of crosslinking conditions.

The extraction of biophenols (BPs) from small branches (fibrous softwood) of olive tree accelerated by microwave assistance is proposed for the first time. Under optimal working conditions, no further extraction of the target analytes was achieved after 10 min, so complete removal of them within this interval was assumed (amounts ca. to 19000, 1000, 2000, 900, and 700 mg/kg of oleuropein, verbascoside, tyrosol, alpha-taxifolin, and hydroxytyrosol, respectively; the three last BPs are absent in branch-free olive leaves). The extracts required no cleanup or concentration prior to injection into a chromatograph-photodiode array detector assembly for individual separation-quantification. Extraction from this raw material was also implemented in continuous and discontinuous-continuous extractors using ultrasound assistance and superheated liquids, respectively, as auxiliary energies, and the results were compared with those obtained by microwave-assisted extraction. The simultaneous extraction of small branches and leaves from olive tree provided extracts with a higher variety of BPs, but either extracts richer in oleuropein and verbascoside without tyrosol, alpha-taxifolin, and hydroxytyrosol or rich in these three BPs can be obtained by separate extraction of leaves and branches, respectively.

Treatment of olive vegetation waste with tyrosinase immobilized on multiwalled carbon nanotubes increased the antioxidant activity as a consequence of the conversion of phenols to corresponding catechol derivatives, as evaluated by DPPH, Comet assay, and micronucleus analyses. During this transformation, 4-hydroxyphenethyl alcohol (tyrosol) was quantitatively converted to bioactive 3,4-dihydroxyphenethyl alcohol (hydroxytyrosol). The hydroxytyrosol-enriched olive vegetation waste also promoted autophagy and inhibited the inflammatory response in human THP-1 monocytes.

Aromatic alcohols (tryptophol, phenylethanol, tyrosol) positively contribute to organoleptic characteristics of wines, and are also described as bioactive compounds and quorum sensing molecules. These alcohols are produced by yeast during alcoholic fermentation via the Erhlich pathway, although in non-Saccharomyces this production has been poorly studied. We studied how different wine yeast species modulate the synthesis patterns of aromatic alcohol production depending on glucose, nitrogen and aromatic amino acid availability. Nitrogen limitation strongly promoted the production of aromatic alcohols in all strains, whereas low glucose generally inhibited it. Increased aromatic amino acid concentrations stimulated the production of aromatic alcohols in all of the strains and conditions tested. Thus, there was a clear association between the nutrient conditions and production of aromatic alcohols in most of the wine yeast species analysed. Additionally, the synthesis pattern of these alcohols has been evaluated for the first time in Torulaspora delbrueckii, Metschnikowia pulcherrima and Starmellera bacillaris.

Yeasts are the key microorganisms that transform grape juice into wine, and nitrogen is an essential nutrient able to affect yeast cell growth, fermentation kinetics and wine quality. In this work, we focused on the intra- and extracellular metabolomic changes of three aromatic amino acids (tryptophan, tyrosine, and phenylalanine) during alcoholic fermentation of two grape musts by two Saccharomyces cerevisiae strains and the sequential inoculation of Torulaspora delbrueckii with Saccharomyces cerevisiae. An UPLC-MS/MS method was used to monitor 33 metabolites, and 26 of them were detected in the extracellular samples and 8 were detected in the intracellular ones. The results indicate that the most intensive metabolomic changes occurred during the logarithm cellular growth phase and that pure S. cerevisiae fermentations produced higher amounts of N-acetyl derivatives of tryptophan and tyrosine and the off-odour molecule 2-aminoacetophenone. The sequentially inoculated fermentations showed a slower evolution and a higher production of metabolites linked to the well-known plant hormone indole acetic acid (auxin). Finally, the production of sulfonated tryptophol during must fermentation was confirmed, which also may explain the bitter taste of wines produced by Torulaspora delbrueckii co-fermentations, while sulfonated indole carboxylic acid was detected for the first time in such an experimental design.

Keywords: bitter taste; chardonnay; nitrogen metabolism; non-Saccharomyces yeast; pinot gris; sulfonation; tyrosol; wine atypical aging; winemaking.

The phenols hydroxytyrosol and tyrosol made abundantly available through olive oil processing were enzymatically transesterified into effective lipophilic antioxidants with cuphea oil. The hydroxytyrosyl and tyrosyl esters made from cuphea oil were assessed for their ability to partition into, locate within and effect the bilayer behavior of 1,2-dioloeoylphosphatidylcholine liposomes and compared to their counterparts made from decanoic acid. Partitioning into liposomes was on the same scale for both hydroxytyrosyl derivatives and both tyrosyl derivatives. All were found to locate nearly at the same depth within the bilayer. Each was found to affect bilayer behavior in a distinct manner.

Olive oil and fruit samples from six cultivars sampled at four different maturity stages were discriminated into cultivars and maturity stages. The variables-volatile and phenolic compounds-that significantly (p < 0.01) discriminated cultivars and maturity stage groups were identified. Separation by stepwise linear discriminant analysis revealed that Manzanilla olive cultivar was separated from cultivars Leccino, Barnea, Mission, Corregiola, and Paragon, whereas cultivars Corregiola and Paragon formed a cluster. The volatile compounds hexanol, hexanal, and 1-penten-3-ol were responsible for the discrimination of cultivars. All maturity stages were discriminated, with the separation of early stages attributed to oil phenolic compounds, tyrosol and oleuropein derivatives, whereas the volatile compounds (E)-2-hexenal, hexanol, 1-penten-3-ol, and (Z)-2-penten-3-ol characterized the separation of all maturity stages and in particular the late stages. Hexanol and 1-penten-3-ol characterized the separation of both cultivars and maturity stages.

At intestinal level, after acute or chronic exposure to iNOS-derived NO, a toxic mechanism of action leads to inflammation and degenerative diseases. The aim of this study was to investigate the effect of glucuronide and sulfate metabolites of the extra virgin olive oil phenols tyrosol (Tyr) and hydroxytyrosol (HT), in comparison with their parent compounds, on the release of NO following exposure to a pro-inflammatory stimulus, the bacterial lipopolysaccharide (LPS). Human colon adenocarcinoma cells (Caco-2), differentiated as normal enterocytes, were treated with pathological concentrations of LPS, in order to stimulate iNOS pathway, which involves NF-ĸB activation through IĸBα phosphorylation and subsequent degradation induced by Akt or MAPKs. All the tested metabolites inhibited NO release induced by LPS, acting as inhibitors of iNOS expression, with an efficacy comparable to that of the parent compounds. HT and Tyr metabolites were effective in the inhibition of IĸBα degradation. No one of the compounds was able to inhibit Akt activation, whereas they modulated p38 and ERK1/2 MAPK. Obtained data show that HT and Tyr metabolites are able to prevent a pathological NO overproduction at intestinal level, where they concentrate, thus significantly contributing to the protective activity exerted by their parent compounds against inflammation.

Recovery of phenols from olive mill wastewater (OMWW) was studied, comparing five sample preparation methods: filtration, solid-phase (SPE), liquid-liquid (LLE) and ultrasonic (US)-assisted extraction of liquid and solid (freeze-dried) OMWW. Results showed that ultrasonication is a good alternative to conventional solvent extractions, providing higher recoveries at both levels of individual and total phenol yields. Sonication of liquid OMWW in organic solvent was more efficient vs its nonassisted counterpart (agitation), but did not provide a representative phenol chromatogram due to ethyl acetate use. By contrast, the US-assisted extraction of freeze-dried OMWW (3 × 20 min) in 100% methanol (1.5 g/25 mL, w/v) offered the highest qualitative-quantitative phenol yields without any US-induced alterations. Moreover, freeze-drying is an excellent preservation of initial liquid OMWW, holding a great potential for delayed analysis. This study is also the first report that Slovenian OMWW may be utilized as a valuable source of phenols, especially hydroxytyrosol and tyrosol.

Rhodiola is native to the high altitude regions of Asia, Europe and Northern Hemisphere. It has a long history of use as a medicinal plant in various ailments, boosting immunity, increasing energy and mental capacity. It is also known as "Adaptogen" to help the body to adapt and resist stress. The part of the plant, which is used for medicinal values, is rhizome, which is an underground stem. The rhizome contains mainly salidroside, rosin, rosavin and p-tyrosol. There are many studies, which have reported the effects of Rhodiola spp. on different organs and health conditions. In this review, we have selected the articles from Pubmed and Google Scholar from year 1992-2016 to report the effects of Rhodiola spp. and their role in curtailing various diseases and stress. The present review emphasizes the medicinal and therapeutic applications of Rhodiola spp. on different experimental models. Overall conclusion is that Rhodiola spp. has immense therapeutic potential and hence, this review would give impetus to new research for the development of Rhodiola based herbal nutraceuticals as well as pharmaceuticals.

In this work, we synthesized a novel polymeric biomaterial platform with tunable functionalizability for extrusion-based 3D printing. Biodegradable polymers were synthesized using 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate (HTy), which is derived from Tyrosol and 2-(4-hydroxyphenyl)acetic acid. p-Phenylenediacetic acid (PDA) was introduced to enhance crystallinity. To enable functionalizability without deteriorating printability, glutamic acid derivatives were introduced into the polymer design, forming copolymers including poly(HTy-co-45%PDA-co-5%Gluhexenamide ester) (HP5GH), poly(HTy-co-45%PDA-co-5%Glupentynamide ester) (HP5GP), and poly(HTy-co-45%PDA-co-5%BocGlu ester) (HP5BG). The resulting polymers have: two melting temperatures (125-131 °C and 141-147 °C), Young's moduli of 1.9-2.4 GPa, and print temperatures of 170-190 °C. The molecular weight (Mw) loss due to hydrolytic degradation was gradual with ∼30% Mw retained after 25 weeks for HP5BG, whereas it was much faster for HP5GP and HP5GH with only 18% Mw retained after 8 weeks. HP5GH and HP5GP were successfully functionalized in solution (bulk) or on the surface using click-based chemistry. Finally, the utilization of this novel platform was demonstrated by studying osteogenic differentiation of human mesenchymal stem cells (hMSCs) using 3D printed scaffolds from HP5GP. Scaffolds were functionalized with azide-Heparin (az-Heparin) to bind and deliver bone morphogenetic protein 2 (BMP-2). This sample group significantly enhanced osteogenic differentiation of hMSCs as compared to unfunctionalized scaffolds incubated directly with az-Heparin or BMP-2 prior to cell culture. This novel polymer platform with tunable functionalizability could be utilized for additive manufacturing of biodegradable devices and scaffolds with tailored mechanical and bioactive properties for a wide range of medical applications including bone fixation devices and scaffolds for bone regeneration.

Fusarithioamide B (6), a new aminobenzamide derivative with unprecedented carbon skeleton and five known metabolites: stigmast-4-ene-3-one (1), stigmasta-4,6,8(14),22-tetraen-3-one (2), p-hydroxyacetophenone (3), tyrosol (4), and fusarithioamide A (5) were separated from Fusarium chlamydosporium EtOAc extract isolated from Anvillea garcinii (Burm.f.) DC. leaves (Asteraceae). The structure elucidation and completeassignment of the isolated metabolites were performed mainly by the aid of various NMR and MS data. Fusarithioamide B (6) has been assessed for antibacterial and antifungal activities towards various microbial strains by disc diffusion assay. It exhibited selective antifungal activity towards C. albicans (MIC 1.9 µg/ml and IZD 14.5 mm), comparing to clotrimazole (MIC 2.8 µg/ml and IZD 17.9 mm). Also, it possessed high antibacterial potential towards E. coli, B. cereus, and S. aureus compared to ciprofloxacin. Furthermore, 6 was tested for the in vitro cytotoxic effect against KB, HCT-116, BT-549, MCF-7, SKOV-3, and SK-MEL cell lines. It had selective and potent effect towards BT-549, MCF-7, SKOV-3, and HCT-116 cell lines with IC50s 0.09, 0.21, 1.23, and 0.59 μM, respectively compared to doxorubicin (IC50s 0.046, 0.05, 0.321, and 0.24 μM, respectively). Fusarithioamide B may provide a lead molecule for future developing of antitumor and antimicrobial agents.

Wound healing is a complex process that consists of three overlapping phases: inflammation, proliferation, and remodeling. A bacterial infection can increase inflammation and delay this process. Microorganisms are closely related to the innate immune system, such as macrophages and neutrophils, as they can start an inflammatory cascade. Essential oils play an important role in the inhibition and prevention of bacterial growth due to their ability to reduce antimicrobial resistance. The possibility to find a strategy that combines antimicrobial and anti-inflammatory properties is particularly appealing for wound healing. In this work, we showcase a variety of patches based on electrospun polycaprolactone (PCL) nanofibers loaded with natural compounds derived from essential oils, such as thymol (THY) and tyrosol (TYR), to achieve reduced inflammation. In addition, we compared the effect these essential oils have on activated macrophages when incorporated into the PCL patch. Specifically, we demonstrate that PCL-THY resulted in more efficient down-regulation of pro-inflammatory genes related to the nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κb) pathway when compared to PCL-TYR and the combination patch containing TYR and THY (i.e., PCL-TYR-THY). Furthermore, PCL-THY displayed low affinity for cell attachment, which may hinder wound adherence and integration. Overall, our results indicate that THY-loaded patches could serve as promising candidates for the fabrication of dressings that incorporate bactericidal and anti-inflammatory properties while simultaneously avoiding the limitations of traditional antibiotic-loaded devices.

From the culture filtrates of Diaporthella cryptica, an emerging hazelnut pathogen, 2-hydroxy-3-phenylpropanoate methyl ester and its 3-(4-hydroxyphenyl) and 3-(1 H-indol-3-yl) analogues, named crypticins A-C, were isolated together with the well-known tyrosol. Crypticins A-C were identified by spectroscopic (essentially nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry) methods. The R absolute configuration (AC) of crypticin A was determined by comparing its optical rotation and electronic circular dichroism (ECD) spectrum with those of papuline, the methyl ester of (-)( S)-phenyllactic acid isolated as the main phytotoxin of Pseudomonas syringae pv. papulans, responsible for apple blister spot. The ACs of crypticins B and C were determined by time-dependent density functional theory calculations of their ECD spectra. Papuline and the new metabolites herein isolated, except tyrosol, were tested at 1 mg/mL on cork oak, grapevine, hazelnut, and holm oak leaves using the leaf puncture assay. They were also tested on tomato cuttings at 0.5 and 0.05 mg/mL. In the leaf puncture assay, none of the compounds was found to be active. Crypticin C and papuline were active in the tomato cutting assay. Additionally, crypticin C displayed moderate inhibitory effect against Phytophthora cambivora.

Polyphenols were characterized from Dothiorella vidmadera (DAR78993), which was isolated from a grapevine in Australia. In total, six polyphenols were isolated including a new polyphenol characterized by a spectroscopic method (essentially NMR and HR ESIMS) as 5-hydroxymethyl-2-isopropoxyphenol. Tyrosol, benzene-1,2,4-triol, resorcinol, 3-(hydroxymethyl)phenol, and protocatechuic alcohol, the latter being the main metabolite, were also isolated. Although these are already known as naturally occurring compounds in microorganisms and plants, this is the first time they have been isolated from fungal organisms involved in grapevine trunk disease. When assayed on tomato seedlings, all the compounds show similar phytotoxic effects. However, when assayed on grapevine leaves (Vitis vinifera cv Shiraz), resorcinol was the most toxic compound, followed by protocatechuic alcohol and 5-hydroxymethyl-2-isopropoxyphenol.

Different phytotoxic metabolites were isolated from the organic extract of <i>Neofusicoccum luteum</i>, <i>Neofusicoccum australe</i>, and <i>Neofusicoccum parvum</i>, causal agents of Botryosphaeria dieback in Australia. <i>N. luteum</i> produced a new disubstituted furo-α-pyrone, a hexasubstituted anthraquinone, and a trisubstituted oxepi-2(7<i>H</i>)-one, luteopyroxin (<b>4</b>), neoanthraquinone (<b>5</b>), and luteoxepinone (<b>7</b>), respectively, together with the known (±)-nigrosporione (<b>6</b>), <em>tyrosol</em> (<b>8</b>), (<i>R</i>)-(-)-mellein (<b>1</b>), and (3<i>R</i>,4<i>S</i>)-(-)- and (3<i>R</i>,4<i>R</i>)-(-)-4-hydroxymellein (<b>2</b> and <b>3</b>). The three melleins and <em>tyrosol</em> were also produced by <i>N. parvum</i>, while <i>N. australe</i> produced (<i>R</i>)-(-)-mellein (<b>1</b>), neoanthraquinone (<b>5</b>), <em>tyrosol</em> (<b>8</b>), and <i>p</i>-cresol (<b>9</b>). Luteopryoxin (<b>4</b>), neoanthraquinone (<b>5</b>), and luteoxepinone (<b>7</b>) were characterized by analyses of physical data, essentially one- and two-dimensional nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry. The relative and absolute configurations of luteopyroxin (<b>4</b>) were determined by nuclear Overhauser effect spectroscopy and experimental and calculated electronic circular dichroism data. When assayed on grapevine leaves, neoanthraquinone (<b>5</b>) showed the highest toxic effect, causing severe shriveling and withering. Luteopyroxin (<b>4</b>), nigrosporione (<b>6</b>), and luteoxepinone (<b>7</b>) also showed different degrees of toxicity, while <i>p</i>-cresol (<b>9</b>) displayed low phytotoxicity.

The aim of this study was to investigate the modulation of polyphenols profile of blackberry purees by soluble dietary fibres (inulin or pectin), during a simulated in vitro gastrointestinal digestion and large intestine fermentation process. Untargeted profiling evidenced that the free phenolic fraction of blackberry puree was characterized mainly by flavonoids, followed by phenolic acids, lignans and other low molecular weight polyphenols, showing clear differences from the bound phenolic fraction detected. This trend could be related to the interactions of dietary fibre and polyphenols, showing synergistic and/or antagonist effect on the bioactivity of polyphenols. On the other hand, in vitro large intestine fermentation of blackberry purees following in vitro gastrointestinal digestion revealed that the highest inclusion level (10% w/w) of soluble dietary fibres was effective in modulating the bioaccessibility of some phenolic classes (mainly phenolic acids, lignans and flavones) characterizing the blackberry puree. In addition, multivariate statistics following metabolomics-based profiling showed that the interaction between fibres and blackberry purees determined a marked modification of both anthocyanins and flavonols during in vitro large intestine fermentation, thus leading to the formation of low-molecular-weight compounds (such as tyrosol, followed by gallic and benzoic acids).

The quality of extra virgin olive oils is affected mainly by hydrolytic and oxidative reactions. The present paper investigated the changes of major and minor components and oxidation indices of three monovarietal extra virgin olive oils after 18 months of storage at room temperature and in dark glass bottles conditions. After storage, the basic quality parameters such as free acidity, peroxide values, extinction coefficients, fatty acids composition, chlorophyll and carotenoid content, did not exceed the upper limits set by European Community Regulations for extra-virgin olive oils. Given the importance of the phenolic fraction, UHPLC-HESI-MS metodology was used. A decrease in 3,4-DHPEA-EDA (oleacin) and p-HPEA-EDA (oleochantal) was detected whereas, an increase of tyrosol and hydroxytyrosol was measured as a consequence of degradation of ligstroside and oleuropein derivatives. Based on the results it is possible to observe the high nutritional value of the studied oils even after 18 months of conservation.

Sparkling wines were elaborated with the nontraditional varieties Villenave, Niagara, Manzoni, and Goethe, and monitored in relation to the changes in phenolic composition, browning index, and glutathione content during 18 months of biological aging (sur lies). Important changes in the phenolic profile, browning index, and glutathione content were observed in the sparkling wines during the over-lees aging period. The major phenolic compound in the sparkling wines was tyrosol, followed by caffeic, trans-caftaric, and gallic acids, catechin and epicatechin. The biological aging led to an increase in the individual phenolic compounds, especially caffeic, gallic, and ellagic acids, and an increase in the browning index was also observed during the aging period. Caffeic acid was significantly correlated with browning and aging period in all sparkling wines, which indicates that this compound can be useful as a quality marker to monitoring the biological aging profile of white sparkling wines. The results obtained indicate that the aging period (sur lie) had an important influence on the changes in the unique phenolic profile of the sparkling wines elaborated with nontraditional varieties. PRACTICAL APPLICATION: In sparkling wines production, the secondary fermentation occurring in the sealed bottle during the vinification contributes greatly to their quality and sensory complexity. The Vitis labrusca and hybrid grapes varieties represent most of the grapes cultivated in Brazil being employed in the elaboration of juices and wines. These varieties present a great oenological potential and have not been explored yet regarding to the production of white sparkling wines. The use of these nontraditional grape varieties cultivated in South Brazil may be a viable alternative in the production of white sparkling wines with biological aging potential and particular bioactive properties.

Antioxidants are highly important gradients used to preserve cosmetic products and reduce the effect of oxidative stress on the skin. The present work explores the possibility of using phenolic compounds of olive mill wastewater (OMW) as effective alternatives to the commercial antioxidants used in cosmetic formulations deemed by their allergic and carcinogenic effects. Esterification of tyrosol and hydroxytyrosol extracted from OMW with various fatty acids was conducted using Novozyme 435 lipase as a biocatalyst. Upon synthesis, butyrate, caprate, laurate, and palmitate tyrosyl and hydroxytyrosyl esters were isolated and evaluated for their antioxidant and antibacterial activities. Results showed that laurate derivatives are the most efficient in preventing lipid oxidation and inhibiting growth of pathogenic strains. In the prospective of industrial use, laurate tyrosyl and hydroxytyrosyl derivatives were incorporated in a formulation of moisturizer to substitute the commercial antioxidant butylated hydroxyltoluene. Oleuropein, extracted from olive leaves powder, was also tested as an antiaging ingredient in cosmetic formulations. The evaluation of physicochemical, microbiological, and sensorial properties of the new cosmetic products indicated that oleuropein and lipophilic derivatives do not affect the properties of the standard formulation. Oleuropein and lipophilic derivatives can be added as active ingredients to stabilize cosmetic preparations.