The emerald ash borer (Agrilus planipennis Fairmaire, EAB) is an alien, invasive wood-boring insect that is responsible for killing millions of ash trees since its discovery in North America in 2002. All North American ash species (Fraxinus spp.) that EAB has encountered have shown various degrees of susceptibility, while Manchurian ash (Fraxinus mandshurica Ruprecht), which shares a co-evolutionary history with this insect, is resistant. Recent studies have looked into constitutive resistance mechanisms in Manchurian ash, concentrating on the secondary phloem, which is the feeding substrate for the insect. In addition to specialized metabolism and defense-related components, primary metabolites and nutritional summaries can also be important to understand the feeding behavior of insect herbivores. Here, we have compared the nutritional characteristics (water content, total protein, free amino acids, total soluble sugars and starch, percent carbon and nitrogen, and macro- and micronutrients) of outer bark and phloem from black, green, white and Manchurian ash to determine their relevance to resistance or susceptibility to EAB. Water content and concentrations of Al, Ba, Cu, Fe, K, Li, tryptophan and an unknown compound were found to separate black and Manchurian ash from green and white ash in a principal component analysis (PCA), confirming their phylogenetic placements into two distinct clades. The traits that distinguished Manchurian ash from black ash in the PCA were water content and concentrations of total soluble sugars, histidine, lysine, methionine, ornithine, proline, sarcosine, tyramine, tyrosol, Al, Fe, K, Na, V and an unknown compound. However, only proline, tyramine and tyrosol were significantly different, and higher, in Manchurian ash than in black ash.

Nonsteroidal anti-inflammatory drugs (NSAIDs) are the most commonly used medications in inflammatory illnesses. However, the gastrointestinal bleeding and toxicity associated with NSAIDs long term use prompted the quest towards investigations for new anti-inflammatory agents. Natural and natural-derived molecules proved its anti-inflammatory efficacy in vitro as well as in vivo. Given this background, the scope of this research involves structural changes of the natural polyphenol (tyrosol) generating two new salicylate derivatives and testing their biological properties, focusing on anti-inflammatory effects assessed in vitro and in vivo assays. The first molecular modification was the introduction of a carboxylic acid group adjacent to the phenol group present in this compound, which creates a new salicylate-like tyrosol. In addition, the acetylation of phenol group in this molecule produced an acetylsalicylate derivative, which may be regarded as aspirin-like natural polyphenol. Interestingly, tyrosol and its novel derivatives attenuated the edema in acute inflammatory response on carrageenan- induced local inflammation in mice. In addition, our results demonstrated that tyrosol and its novel derivatives were able to reduce the chemotaxis of neutrophil assessed in vitro model by chemo attractant (fMLP). Furthermore, only derivative 2 was able to reduce this effect in the acute inflammatory model. In (DPPH)- scavenging activity, tyrosol derivatives demonstrated a minor antioxidant activity, which may suggest that radical scavenging is not a major pathway involved in the anti-inflammatory effects of these derivatives. Salicylate-like tyrosol derivatives are of particular interest for future studies.

The sorption and release of tyrosol and caffeic acid, two biophenolic antioxidants with known health benefits, in different insoluble cyclodextrin polymers have been studied. Cyclodextrin polymers were synthesized by cross-linking β-cyclodextrin or 50:50 w/w nominal mixtures of α- and β-cyclodextrins using either epichlorohydrin (EP) or toluene-2,4-diisocyanate (TDI) as cross-linking agents. An analogous sucrose polymer was prepared using EP as cross-linking reagent. Freundlich isotherms and isosteric heats of sorption for tyrosol and caffeic acid in the insoluble β-cyclodextrin polymer cross-linked with epichlorohydrin at 50 °C were obtained and discussed. Finally, the release of tyrosol and caffeic acid has been studied from loaded polymer disks, the microstructures of which were characterized by mercury intrusion porosimetry. Caffeic acid shows greater affinity than tyrosol for the polymeric matrices as it presents a higher sorption and a lower and slower release. However, tyrosol has a higher isosteric heat of sorption for low coverages.

Three different high performance liquid chromatography columns were accessed for phenolic compounds (PC) separation in the hydrophilic fraction of extra virgin olive oil (EVOO). Two fully porous C₁₈ bonded silica phases and one partially porous biphenyl column were used. Biphenyl column allowed for an increase of more than 30% in peak capacity (n_c), higher selectivity (α) (1.045), and improved retention (k), with a reduction of 22.1% in the retention time. The higher resolution (R_s) was obtained by using the biphenyl column, with a fair separation of oleuropein aglycone isomers (OAI) and a good identification of caffeic acid (CA). Tyrosol (T), hydroxytyrosol (HT), and dihydroxyphenyl glycol (DHPG) were also well separated and identified. Moreover, the method using a biphenyl column was fully validated according to the requirements for new methods. For all parameters, the method applying the biphenyl column proved to be a reliable, accurate, and robust tool for separation, identification, and quantification of the main PCs in EVOOs.

This work seeks to explore and understand the effects of column orientation and degree of modification of continuous stationary phase gradient columns under a mobile phase gradient using both simulations and experiments. Peak parameters such as retention times, peak widths and resolution are obtained for five phenolic compounds on a C₁₈-silica gradient stationary phase. Simulations show that peak widths for the solutes are dependent upon the fractional composition of C₁₈ and orientation of the stationary phase gradient when coupled to a mobile phase gradient. Also, when compared to a simulated uniform mixed-mode column, peak widths reach a minimum on the gradient column with a coverage higher than 50% C₁₈ where the column is oriented to have the C₁₈ dense region at the end. Experimentally, continuous stationary phase gradients were fabricated to have a total C₁₈ composition of 78% of the original uniform column with an exponential profile using a previously described destructive controlled rate infusion method. Under gradient mobile phase conditions, experimental retention times for the gradient column showed a significant increase compared to the original 100% C₁₈ column. Simulations with a similar C₁₈ composition, however, predicted decreased retention times from the original C₁₈ column. A statistical increase in the retention time of protocatechuic acid and decrease in the peak width of tyrosol, caffeic acid, and coumaric acid were noted when the gradient column was oriented to have the C₁₈ dense region located near the detector. Collectively, combining gradients in both the mobile and stationary phases can yield interesting neighboring ligand effects and peak broadening/focusing effects.

OBJECTIVE

To study the secondary metabolites of Coriolopsis sp. G066.

METHODS

The compounds were isolated by various chromatographic methods (silica gel, reverse silica gel, Sephadex LH-20, preparative TLC and so on). Their structures were determined by extensive analysis of their spectroscopic data as well as by comparison with literature reports.

RESULTS

Six compounds were isolated and identified as diaporthein A(1), tyrosol(2), eburicoic acid(3), ergosterol(4), ergosterol peroxide(5) and cerevisterol (6).

CONCLUSIONS

All the compounds are isolated from the genus for the first time.

A robust method was developed to investigate the liposomal behavior of novel enzymatically-synthesized hydroxytyrosol and tyrosol phospholipids. Bilayer characteristic obtained by this method, including bilayer formation stability and adsorption properties, were explored using dynamic light scattering, zeta-potential measurements, and quartz crystal microbalance with dissipation monitoring (QCMD), respectively. Liposome diameters were found to typically increase from pH 5.5 to pH 10. Zeta potentials values, on the other hand, were found to be well below -25 mV at all pH conditions explored, with the lowest values (and thus, the best liposome stability) at pH 5.5 or pH 10. Quartz crystal microbalance with dissipation monitoring measurements demonstrated that 100% 1,2-dioloeoylphosphatidyl-hydroxytyrosol (DOPHT) liposomes adsorbed intact onto silica in buffer conditions at pH 5.5 and with no calcium, or at pH 7.5 with calcium (no adsorption was detected at pH 10). 1,2-Dioleoylphosphatidyl-tyrosol (DOPT) liposomes were shown to adsorb intact under buffer conditions only at pH 5.5 with and without calcium. 1,2-Dioleoylphosphatidyl-2-phenolethanol (DOPPE), in comparison, readily adsorbed intact at pH 7.5 without calcium and just slightly at pH 5.5 with calcium present, but formed a supported bilayer over hours at pH 5.5 in the absence of calcium ions.

Two by-products containing phenols and polysaccharides, a "pâté" (OP) from the extra virgin olive oil milling process and a decoction of pomegranate mesocarp (PM), were investigated for their effects on human microbiota using the SHIME^® system. The ability of these products to modulate the microbial community was studied simulating a daily intake for nine days. Microbial functionality, investigated in terms of short chain fatty acids (SCFA) and NH₄⁺, was stable during the treatment. A significant increase in Lactobacillaceae and Bifidobacteriaceae at nine days was induced by OP mainly in the proximal tract. Polyphenol metabolism indicated the formation of tyrosol from OP mainly in the distal tract, while urolithins C and A were produced from PM, identifying the human donor as a metabotype A. The results confirm the SHIME^® system as a suitable in vitro tool to preliminarily investigate interactions between complex botanicals and human microbiota before undertaking more challenging human studies.

The Olive Mill Wastewater (OMWW) biodegradation in an external ceramic membrane bioreactor (MBR) was investigated with a starting acclimation step with a Ultrafiltration (UF) membrane (150 kDa) and no sludge discharge in order to develop a specific biomass adapted to OMWW biodegradation. After acclimation step, UF was replaced by an Microfiltration (MF) membrane (0.1 µm). Sludge Retention Time (SRT) was set around 25 days and Food to Microorganisms ratio (F/M) was fixed at 0.2 kgCOD kgMLVSS-1 d-1. At stable state, removal of the main phenolic compounds (hydroxytyrosol and tyrosol) and Chemical Oxygen Demand (COD) were successfully reached (95% both). Considered as a predominant fouling factor, but never quantified in MBR treated OMWW, Soluble Microbial Products (SMP) proteins, polysaccharides and humic substances concentrations were determined (80, 110 and 360 mg L-1 respectively). At the same time, fouling was easily managed due to favourable hydraulic conditions of external ceramic MBR. Therefore, OMWW could be efficiently and durably treated by an MF MBR process under adapted operating parameters.

A phenolic-UDP-glycosyltransferase Bs-PUGT from Bacillus subtilis PI18 was cloned and expressed in Escherichia coli BL21 (DE3). The purified Bs-PUGT could catalyze the glycosylation of tyrosol, 4-hydroxybenzyl alcohol, 2-hydroxybenzyl alcohol, caffeic acid, cinnamic alcohol, ferulic acid, and so on. This enzyme showed a high activity and stability over a broad pH range and was sensitive to temperature. Studies on the kinetic parameters indicated that the affinity of Bs-PUGT to UDP-G (Km) and its catalytic efficiency (Kcat) increased by 1.5-fold and 1.7-fold, respectively, with the addition of 10 mM Ca²⁺. The most effective glycosylation of caffeic acid catalyzed by whole-cell E. coli/Bs-PUGT was achieved with a molar yield of 78.3% in a system with pH 8.0, 30 °C, 25 g/L sucrose, 10 mM Ca²⁺, and 0.5 g/L substrate concentration. The addition of Ca²⁺ increased the molar yield of caffeic acid glucosides and shortened the reaction. This work proposes a strategy for the efficient glycosylation of phenolic compounds by microbe-derived glycosyltransferase assisted by metal ions.

Current trends toward naturally occurring compounds of therapeutic interest have contributed to an increasing number of studies on olive oil phenolics in the treatment of diseases with oxidative and inflammatory origins. Recent focus has been on olive oil wastewater, which is richer in phenolic compounds than olive oil itself. In this review, we present findings demonstrating the potential use of olive mill wastewater in dermatology. Particular attention is given to compounds with proven benefits in topical pharmacology: caffeic and ferulic acids, tyrosol and hydroxytyrosol, verbascoside, and oleuropein. The review is divided into different sections: inflammatory skin diseases, microbial effects, wound healing in addition to the antimelanoma properties of olive mill waste phenolics, and their potential in sun protection agents. There is strong evidence to support further studies into the valorization of this abundant and sustainable source of phenolic compounds for use in dermatology and dermo-cosmetic preparations.

Keywords: inflammatory skin conditions; melanoma; olive mill waste; phenolic compounds; sun protection.

Here, we report the complete genome sequence of Halomonas olivaria strain TYRC17, a moderately halophilic, Gram-negative bacterium that was isolated from olive processing effluents. The 5-Mbp genome consists of 7,375 protein-coding sequences, including a variety of genes involved in tyrosol metabolism, nitrate respiration, and the production of polysaccharides.

A new phenolic acid ester, 4'-hydroxyphenylethyl 4,8(R)-dihydroxyphenylpropionate(1), was isolated from an endophytic fungus Colletotrichum capsici of Paeonia lactiflora roots, along with eight known phenolic derivatives, tyrosol(2), 2-(4-hydroxyphenyl) ethyl acetate(3), methyl p-hydroxyphenylacetate(4), methyl m-hydroxyphenylacetate(5), 4-(4-hydroxyphene-thoxy)-4-oxobutanoic acid(6), 4-hydroxyphenethyl methyl succinate(7), trichodenol B(8) and 4-hydroxyphenethyl 2-(4-hydroxyphenyl) acetate(9). Their structures were identified by a combination of high-resolution electrospray ionization mass spectrometry(HR-ESI-MS), nuclear magnetic resonance(NMR) spectroscopy, ultraviolet(UV) spectroscopy and electronic circular dichroism(ECD) spectroscopy. Compounds 2-9 were isolated from this fungus for the first time.

Keywords: Colletotrichum capsici; Paeonia lactiflora; endophytic fungi; phenolic acid ester; secondary metabolites.

Asthma is an inflammatory disease that affects many people around the world, especially persons at paediatric age group. The effectiveness of tyrosol, a natural phenolic compound, was examined in the asthma model induced by ovalbumin (OVA). For this purpose, four groups, each consisting of eight rats, were arranged. For 21 days, physiological saline solution was treated to the control group and OVA was treated to the groups of OVA, OVA + dexamethasone (Dexa) and OVA + tyrosol groups, intraperitoneally and through inhalation. Additionally, 0.25 mg/kg Dexa was treated to the OVA + Dexa group and 20 mg/kg tyrosol to the OVA + tyrosol group by oral gavage. Serum, blood, bronchoalveolar lavage fluid (BALF) and lung tissues of the rats were examined. It was observed that MDA level decreased, GSH level and GPx activity increased, and there was no change in CAT activity in lung tissues of the tyrosol treatment groups. It was also observed that NF-κB, TNF-α, IL-4, IL-5, IL-13, IFN-γ and IgE levels decreased compared to the OVA group in lung tissue and serum samples except for serum NF-κB and IL-4. However, no effect on IL-1 β level was observed. In addition, it was determined that tyrosol treatment increased the IL-10 level on both tissue samples. The results of the histopathological investigation of lung tissue showed that tyrosol significantly ameliorated OVA-induced histopathological lesions. Additionally, PAS staining showed that mucus hypersecretion was significantly reduced with the use of tyrosol. In addition, it was determined that the number of eosinophils decreased significantly in blood and BALF samples. The obtained results showed that tyrosol possessed antioxidant and anti-inflammatory features on OVA-induced rats and preserved tissue architecture.

Keywords: Anti-allergic; Anti-inflammatory; Antioxidant; Asthma; Tyrosol.

pRS episomal plasmids are widely used in Saccharomyces cerevisiae, owing to their easy genetic manipulations and high plasmid copy numbers (PCNs). Nevertheless, their broader application is hampered by the instability of the pRS plasmids. In this study, we designed an episomal plasmid based on the endogenous 2μ plasmid with both improved stability and increased PCN, naming it p2μM, a 2μ-modified plasmid. In the p2μM plasmid, an insertion site between the REP1 promoter and RAF1 promoter was identified, where the replication (ori) of Escherichia coli and a selection marker gene of S. cerevisiae were inserted. As a proof of concept, the tyrosol biosynthetic pathway was constructed in the p2μM plasmid and in a pRS plasmid (pRS423). As a result, the p2μM plasmid presented lower plasmid loss rate than that of pRS423. Furthermore, higher tyrosol titers were achieved in S. cerevisiae harboring p2μM plasmid carrying the tyrosol pathway-related genes. Our study provided an improved genetic manipulation tool in S. cerevisiae for metabolic engineering applications, which may be widely applied for valuable product biosynthesis in yeast.

Keywords: 2μ plasmid; Saccharomyces cerevisiae; pRS423; plasmid stability; tyrosol.

One strategy to increase the yield of desired fermentation products is to redirect substrate carbon from biomass synthesis. Non-genetic approaches to alter metabolism may have advantages of general applicability and simple control. The goal of this study was to identify and evaluate chemicals for their ability to inhibit the growth of Saccharomyces cerevisiae while allowing ethanol production with higher yields. Eight potential growth-inhibitory chemicals were screened for their ability to reduce cell growth in 24-well plates. Effective chemicals were then evaluated in cultivations to identify those that simultaneously reduced biomass yield and increased ethanol yield. The yeast quorum-sensing molecules 2-phenylethanol, tryptophol, and tyrosol, were found to increase the ethanol yield of S. cerevisiae JAY 270. These molecules were tested with seven other yeast strains and ethanol yields of up to 15% higher were observed. The effects of 2-phenylethanol and tryptophol were also studied in bioreactor fermentations. These findings demonstrate for the first time that the ethanol yield can be improved by adding yeast quorum-sensing molecules to reduce the cell growth of S. cerevisiae, suggesting a strategy to improve the yield of ethanol and other yeast fermentation products by manipulating native biological control systems.

Keywords: 2-phenylethanol; Redirected carbon flux; quorum sensing; tryptophol; tyrosol.

The wastes generated during the olive oil extraction process, even if presenting a negative impact for the environment, contain several bioactive compounds that have considerable health benefits. After suitable extraction and purification, these compounds can be used as food antioxidants or as active ingredients in nutraceutical and cosmetic products due to their interesting technological and pharmaceutical properties. The aim of this review, after presenting general applications of the different types of wastes generated from this industry, is to focus on the olive pomace produced by the two-phase system and to explore the challenging applications of the main individual compounds present in this waste. Hydroxytyrosol, tyrosol, oleuropein, oleuropein aglycone, and verbascoside are the most abundant bioactive compounds present in olive pomace. Besides their antioxidant activity, these compounds also demonstrated other biological properties such as antimicrobial, anticancer, or anti-inflammatory, thus being used in formulations to produce pharmaceutical and cosmetic products or in the fortification of food. Nevertheless, it is mandatory to involve both industries and researchers to create strategies to valorize these byproducts while maintaining environmental sustainability.

Keywords: bioactive compounds; cosmetics; food fortification; olive wastes; pharmaceuticals.

The diet management is imperative to anticipate risk factors that favour the development of diseases; indeed, the intake of virgin olive oil could be an alternative natural source of α-glucosidase enzyme inhibitors, which delay the digestion rate of carbohydrates. Consequently, the impact of diabetes mellitus (DM) could be diminished. Extra Virgin Olive Oils (EVOO) were elaborated from Galician autochthonous variety 'Brava Gallega' with olives selected at three different degree of ripeness (ripening index, RI: 1.4, 3.0, 5.5) in order to assess the effect of maturation on overall chemical composition, sensory quality, and enzyme inhibition. The phenolic profile of the EVOOs determined by LC-ESI-IT-MS exhibited quantitative differences as ripening advanced; for example oleocanthal, tyrosol, luteolin and apigenin concentrations were higher in the overripe olive oil (RI 5.5). Anyway, the phenolic extracts (from every tested RI) were more active than acarbose. In particular, those obtained from the most mature olives displayed the most powerful inhibitory activity (IC₅₀ value of 143 µg of dry extract/mL). In addition, the significant effect of these compounds (i.e. luteolin, apigenin, tyrosol and oleocanthal) on the inhibitory activity of the olive oil extracts was demonstrated. Our results suggest that, regardless of RI, the inhibitory activity of 'Brava Gallega' olive oils could represent a valuable strategy for reinforcing the health claim of olive oil for phenolic compounds.

Keywords: Diabetes mellitus; Phenolic compounds; Ripening index; Sensory quality; Virgin olive oil; α-glucosidase.

Extra virgin olive oil (EVOO) phenols represent a significant part of the intake of antioxidants and bioactive compounds in the Mediterranean diet. In particular, hydroxytyrosol (HTyr), tyrosol (Tyr), and the secoiridoids oleacein and oleocanthal play central roles as anti-inflammatory, neuro-protective and anti-cancer agents. These compounds cannot be easily obtained via chemical synthesis, and their isolation and purification from EVOO is cumbersome. Indeed, both processes involve the use of large volumes of organic solvents, hazardous reagents and several chromatographic steps. In this work we propose a novel optimized procedure for the green extraction, isolation and purification of HTyr, Tyr, oleacein and oleocanthal directly from EVOO, by using a Natural Deep Eutectic Solvent (NaDES) as an extracting phase, coupled with preparative high-performance liquid chromatography. This purification method allows the total recovery of the four components as single pure compounds directly from EVOO, in a rapid, economic and ecologically sustainable way, which utilizes biocompatible reagents and strongly limits the use or generation of hazardous substances.

Keywords: extra virgin olive oil; green chemistry; hydoxytyrosol; mass spectrometry; natural deep eutectic solvents; oleacein; oleocanthal; secoiridoids; tyrosol; ultra-high-performance liquid chromatography.

The components adsorbed onto activated charcoal following the fermentation process of the Japanese rice wine "sake" have been studied with the aim of identifying suitable applications for this industrial food waste product. The absorbed materials were effectively extracted from the charcoal, and inhibited the activity of several mammalian DNA polymerases (pols). Subsequent purification of the extract afforded tyrosol [4-(2-hydroxyethyl)phenol] as the active component, which selectively inhibited the activity of 11 mammalian pols with IC50 values in the range of 34.3-46.1 μM. In contrast, this compound did not influence the activities of plant or prokaryotic pols or any of the other DNA metabolic enzymes tested. Tyrosol suppressed both anti-inflammatory and antiallergic effects in vivo, including 12-O-tetradecanoylphorbol-13-acetate-induced inflammatory mouse ear edema, and immunoglobulin E-induced passive cutaneous anaphylactic reaction in mice. These results suggested that this byproduct formed during the sake-brewing process could be used as an anti-inflammatory and/or antiallergic agent.

Fermentation is a preservation process responsible for increasing food product shelf life. In this context, alcoholic fermentation can add value to unconventional Amazon fruits, e.g., araçá-boi (Eugenia stipitata). This fruit has various antioxidant phenolic compounds with well-known nutraceutical properties. However, araçá-boi is still underexplored by food industry. This rationale led to investigate the influence of five commercial yeasts (Saccharomyces cerevisiae) and filtration process on chemical composition and antioxidant capacity of araçá-boi beverages. DPPH and Folin Ciocalteu assays were used to determine antioxidant capacity and total phenolic content. Organic compounds' contents were assessed by NMR-ERETIC2. In all beverages, ten compounds [tyrosol, sucrose, fructose, (α/β)-glucose, ethanol, malic, citric, gallic, and succinic acids] were identified and quantified. The highest phenolic concentrations [gallic acid (390.0 µM) and tyrosol (380.0 µM)] were found in Biolievito Bayanus (BBA) beverage. The new BBA beverage was used for investigating filtration process influence on chemical composition and antioxidant responses. Alcoholic content (unfiltered: 13.9°GL and filtered: 12.7°GL), antioxidant responses, and total phenolic contents were influenced by filtration process. The yeast type and unfiltered process were determinant for chemical content and antioxidant capacity of beverages. These results might be useful to private sector and future production and commercialization of araçá-boi beverages.

Keywords: DPPH; Eugenia stipitata; Gallic acid; PULCON; Total phenolic; Tyrosol.

The plant kingdom provides a large resource of natural products and various related enzymes are analyzed. The high catalytic activity and easy genetically modification of microbial enzymes would be beneficial for synthesis of natural products. But the identification of functional genes of target enzymes is time consuming and hampered by many contingencies. The potential to mine microbe-derived glycosyltransferases (GTs) cross the plant kingdom was assessed based on alignment and evolution of the full sequences and key motifs of target enzymes, such as Rhodiola-derived UDP-glycosyltransferase (UGT73B6) using in salidroside synthesis. The GTs from Bacillus licheniformis ZSP01 with high PSPG motif similarity were speculated to catalyze the synthesis of salidroside. The UGTBL1, which had similarity (61.4%) PSPG motif to UGT73B6, displayed efficient activity and similar regioselectivity. Highly efficient glycosylation of tyrosol (1 g/L) was obtained by using engineered E. coli harboring UGTBL1 gene, which generated 1.04 g/L salidroside and 0.99 g/L icariside D2. All glycosides were secreted into the culture medium and beneficial for downstream purification. It was the first report on the genome mining of UGTs from microorganisms cross the plant kingdom. The mining approach may have broader applications in the selection of efficient candidate for making high-value natural products.

The aerial parts of <i>Salvia cinnabarina</i> afforded two undescribed labdane diterpenoids <b>1</b> and <b>2</b> (malonylcommunol and 6β-hydroxy-<i>trans</i>-communic acid) along with two known labdane diterpenoids, <i>trans</i>-communic acid (<b>3</b>) and <i>trans</i>-communol (<b>4</b>). Additionally, seven known metabolites were also isolated; two isopimarane diterpenoids <b>5</b> and <b>6</b>, two sesquiterpenoids identified as β-eudesmol (<b>7</b>) and cryptomeridiol (<b>8</b>), and three aromatic compounds identified as phthalic acid (<b>9</b>), a mixture of <em>tyrosol</em> fatty acid esters (<b>10</b>) and the flavone salvigenine (<b>11</b>). While compounds compounds <b>1</b>-<b>3</b> showed significant inhibition of yeast α-glucosidase, compounds <b>2</b>, <b>3</b> and <b>7</b> had no anti-inflammatory activity in the edema model induced by TPA. This paper is not only the first report on a wild population of <i>Salvia cinnabarina</i>, but also of the presence of labdane-type diterpenoids in a Mexican <i>Salvia</i> sp.

Oxidative stress can stimulate the secretion of pro-inflammatory cytokines. Interleukin-8 (IL-8) has been implicated in the pathogenesis of inflammatory bowel disease and the metastatic spread of colorectal cancer. The flowers of Osmanthus fragrans (sweet olive) are used to alleviate dysentery with blood in the bowel, as well as stomach ache and diarrhea. However, the evidence of their therapeutic effects on these symptoms remains unclear. In the present study, the protective effects of sweet olive flower ethanolic extract (OFE) against oxidative stress in WiDr cells was assessed by evaluating its 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. In addition, cellular IL-8 secretion was evaluated. Notably, high-performance liquid chromatography showed verbascoside to be the primary constituent in OFE; it exhibited a DPPH scavenging activity with an IC50 of 8.23 μg/mL. Moreover, OFE (1 to 100 μg/mL) showed a potent, dose-dependent inhibitory effect on H2 O2 -induced IL-8 secretion in WiDr cells. Nine compounds were isolated from OFE based on a protective effect-guided purification process. Of these compounds, 5 phenolic compounds-verbascoside, phillygenin, tyrosol, methyl 4-hydroxycinnamate, and eutigoside A-reduced IL-8 secretion at 10 μg/mL treatment concentrations. Further analysis showed that the anti-inflammatory effects of OFE likely occurred via nuclear factor-κB pathway inhibition, which attenuates IL-8 secretion in cells. Collectively, these data suggest that OFE could be developed as an agent that suppresses IL-8 secretion to treat chronic inflammatory diseases.