Phenolic composition and bioactivity of Ribes magellanicum fruits from southern Patagonia.

Eight Ribes magellanicum collections from three different places in southern Patagonia were compared for content of different groups of phenolics, antioxidant capacity and inhibition of enzymes related to metabolic syndrome (α-amylase, α-glucosidase and pancreatic lipase). The sample with the highest antioxidant capacity was assessed for glutathione (GSH) synthesis stimulation in human gastric adenocarcinoma (AGS) cells. The chemical profile was determined by high performance liquid chromatography with tandem mass spectrometry detection (HPLC-MS/MS) and the main phenolics were quantified. The samples from Navarino Island and Reserva Nacional Magallanes showed higher content of anthocyanins and caffeoylquinic acid, with better activity towards α-glucosidase and antioxidant capacity. A sample from Omora (Navarino Island), significantly increased intracellular GSH content in AGS cells. Some 70 compounds were identified in the fruit extracts by HPLC-MS/MS. The glucoside and rutinoside from delphinidin and cyanidin and 3-caffeoylquinic acid were the main compounds. Different chemical profiles were found according to the collection places.

Antioxidant capacity and inhibition of metabolic syndrome-associated enzymes by Cryptocarya alba fruits.

The fruits of the native tree Cryptocarya alba Mol. (Lauraceae), known as "peumo" were consumed by the Mapuche Amerindians in Chile both raw and after boiling. The aim of this work was to compare the content of phenolic, procyanidins, antioxidant capacity and inhibition of enzymes related with metabolic syndrome (α-glucosidase, α-amylase and pancreatic lipase) from the phenolic enriched extracts (PEEs) of peumo fruits. Fruits were collected during two years in three different places in central Chile and were investigated raw, boiled, and after separation into cotyledons and peel. The water resulting from the fruit decoction was also analyzed. The composition of the PEE was assessed by HPLC-DAD-MS/MS and the main compounds were quantified by HPLC. The strong inhibitory effect on α-glucosidase, with IC50 values below 1 µg/mL for several samples, was related, at least in part, to the content of 3-caffeoylquinic acid, 5-caffeoylquinic acid and (-)-epicatechin. The effect of the PEE on pancreatic lipase is of interest and can be partially explained by the (-)-epicatechin content. PCA analyses showed a clear separation of the samples according to the fruit parts and processing. However, no differences by geographic origin were observed. The activity of peumo PEEs on enzymes related to metabolic syndrome and its antioxidant capacity support further studies on the health promoting properties of this native Chilean food plant.

Phenolic Composition, Antioxidant Capacity, and α-Glucosidase Inhibition of Boiled Green Beans and Leaves from Chilean Phaseolus vulgaris.

The tender green pods of the common bean (Phaseolus vulgaris L.) are marketed fresh, frozen or canned. The main bean accessions cultivated for green pods in central Chile are Arroz, Magnum, Peumo and the introduced Malibú. Little is known about the identity of phenolics in the processed pods or in the boiled bean leaves. Raw leaves from Chilean bean landraces showed a strong inhibition towards the enzyme α-glucosidase, associated with flavonoids and caffeoyl malic acid content. The aim of this work was to assess the phenolic composition, antioxidant capacity and activity towards α-glucosidase of boiled leaves and green pods from selected bean landraces. The study was performed with four green pods samples and six leaf accessions, respectively. The leaves included the continuous growth bean Ñuño (red seed and black seed). Antioxidant capacity and inhibition of α-glucosidase were measured. The main phenolics were identified by comparison with standards and were quantified using calibration curves. The extracts of most boiled green pods inhibited α-glucosidase while the leaves were inactive. The content of phenolics in the boiled pods is low, with rutin and quercetin 3-O-glucuronide as the main constituents. In boiled leaves, the main phenolics were quercetin 3-O-glucuronide and kaempferol 3-O-glucuronide. The main flavonoids and caffeoyl malic acid in leaves decreased after boiling. Boiling affected the phenolic profile, reducing antioxidant capacity and glucosidase inhibition, highlighting the importance of characterizing foods as they are ingested.

Antiviral Effect of Natural and Semisynthetic Diterpenoids against Adenovirus Infection in vitro.

The emergence and re-emergence of viruses has highlighted the need to develop new broad-spectrum antivirals to mitigate human infections. Pursuing our search for new bioactive plant-derived molecules, we study several diterpene derivatives synthesized from jatropholones A and B and carnosic acid isolated from Jatropha isabellei and Rosmarinus officinalis, respectively. Here, we investigate the antiviral effect of the diterpenes against human adenovirus (HAdV-5) that causes several infections for which there is no approved antiviral therapy yet. Ten compounds are evaluated and none of them present cytotoxicity in A549 cells. Only compounds 2, 5 and 9 inhibit HAdV-5 replication in a concentration-dependent manner, without virucidal activity, whereas the antiviral action takes place after virus internalization. The expression of viral proteins E1A and Hexon is strongly inhibited by compounds 2 and 5 and, in a lesser degree, by compound 9. Since compounds 2, 5 and 9 prevent ERK activation, they might exert their antiviral action by interfering in the host cell functions required for virus replication. Besides, the compounds have an anti-inflammatory profile since they significantly inhibit the levels of IL-6 and IL-8 produced by THP-1 cells infected with HAdV-5 or with an adenoviral vector. In conclusion, diterpenes 2, 5 and 9 not only exert antiviral activity against adenovirus but also are able to restrain pro-inflammatory cytokines induced by the virus.

Clinal versus disruptive latitudinal variation in fruit traits of a South American mistletoe.

Fruit traits have historically been interpreted as plant adaptations to their seed dispersers. On the other hand, different environmental factors, which vary spatially and temporally, can shape fruit-trait variation. The mistletoe Tristerix corymbosus has a latitudinal distribution along the South American Pacific rim that encompasses two different biomes, the matorral of central Chile and the temperate forest that extends south of the matorral. This mistletoe shows contrasting fruiting phenology (spring vs summer), fruit color (yellow vs green), and seed dispersers (birds vs marsupial) in these two biomes. We characterized geographic variation of morphological and nutritional fruit traits of T. corymbosus to evaluate which macroecological factor, biome or latitude, better explains spatial variation in these variables. For each of 22 populations, we obtained environmental data (temperature, precipitation, and canopy cover), measured fruit and seed morphology traits (size, shape, and weight), and pulp moisture and nutritional content (fiber, protein, fat, carbohydrates, ash, and caloric content). Patterns of variation for each variable were described by fitting and comparing five different simple models varying in slope, intercept or both. Fruit morphology showed a clear biome-related disruptive pattern, seed morphological traits were unrelated to either biome or latitude, whereas nutritional variables showed diverse patterns. Different environmental factors seem to affect fruit development and phenology, determining the observed fruit characteristics, with seed dispersers playing a minor role in shaping these patterns. More generally, the contrasting plant-seed disperser associations we addressed can be interpreted as the outcome of an ecological-fitting rather than of a coevolutionary process.

A paraguayan toad Rhinella schneideri preparation based on Mbya tradition increases mitochondrial bioenergetics with migrastatic effects dependent on AMPK in breast cancer cells.

ETHNOPHARMACOLOGICAL RELEVANCE: In Paraguay, healers from the Mbya culture treat cancer with a recipe prepared with the native toad Rhinella schneideri. However, the chemical composition and biological effects of the recipe remain unknown. AIM OF THE STUDY: The aim is to determine the composition of the traditional preparation made using the toad R. schneideri and to evaluate its effect on human breast cancer (BC) cells. MATERIALS AND METHODS: The metabolites contained in the preparation were concentrated using XAD-7 resin, and the concentrate was analyzed by HPLC-MS/MS. The effect of the preparation was assessed in normal (MCF10F) and BC cells (MDA-MB-231 and MCF7). The mitochondrial membrane potential (Δψm), reactive oxygen species (ROS) levels, and cell cycle progression were determined by flow cytometry. The oxygen consumption rate (OCR) was measured by Clark electrode, and fibronectin-dependent migration in normoxia and hypoxia-like conditions were evaluated by transwell assay. RESULTS: From the Amberlite-retained extract from the preparation, 24 compounds were identified, including alkaloids, amino acids, bufadienolides, and flavonoids, among others. The crude extract (CE) did not affect cell cycle progression and viability of BC cell lines. Moreover, it did not make cancer cells more sensitive to the cytotoxic effect of the chemotherapeutics doxorubicin and teniposide. On the other hand, the CE reduced the menadione-induced ROS production and increased NADH, Δψm, and the OCR. Respiratory complexes I and III as well as ATP synthase levels were increased in an AMPK-dependent manner. Moreover, the CE inhibited the migration of BC cells in normoxia and a hypoxia-like condition using CoCl2 as a HIF1α-stabilizing agent. This latter effect involved an AMPK-dependent reduction of HIF1α levels. CONCLUSIONS: The Paraguayan toad recipe contains metabolites from the toad ingredient, including alkaloids and bufadienolide derivatives. The CE lacks cytotoxic effects alone or in combination with chemotherapeutics. However, it increases mitochondrial bioenergetics and inhibits the cancer cell migration in an AMPK-dependent manner in BC cells. This is the first report of the in vitro anticancer effect of a traditional Rhinella sp. toad preparation based on Mbya tradition.

Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations.

Triadimefon (TDM) and cyproconazole (CPZ) are two triazoles widely used as fungicides. Several azoles were synthesised starting from commercial TDM and CPZ. The compounds were evaluated against phytopathogenic filamentous fungi, including Aspergillus fumigatus (AF), A. niger (AN), A. ustus (AU), A. japonicus (AJ), A. terreus (AT), Fusarium oxysporum and Botrytis cinerea isolated from grapevine in the province of San Juan, Argentina. Three of the synthesised compounds (1-(Biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one, 1; 2-(Biphenyl-4-yl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, 3; 3-Cyclopropyl-2-(4'-fluorobiphenyl-4-yl)-1-(1H-1,2,4-triazol1-yl)butan-2-ol, 4) presented remarkable in vitro fungicidal properties, with better effects than TDM and CPZ on some of the target fungi. Cytotoxicity was assessed using human lung fibroblasts MRC5. Derivative 1, with IC50 values of 389.4 µM, was less toxic towards MRC-5 human lung fibroblasts than commercial TDM (248.5 µM) and CPZ (267.4 µM). Docking analysis and molecular dynamics simulations suggest that the compounds present the same interaction in the binding pocket of the CYP51B enzyme and with the same amino acids as CPZ. The derivatives investigated could be considered broad-spectrum but with some selectivity towards imperfect fungi.

Phenolic Composition and α-Glucosidase Inhibition of Leaves from Chilean Bean Landraces.

The MeOH:H2O (7:3) extracts of leaves from Chilean bean landraces were assessed for total phenolic (TP), total flavonoid (TF), total proanthocyanidin (TPA) content, antioxidant capacity (ORAC, FRAP, TEAC, CUPRAC, DPPH) and the inhibition of enzymes associated with metabolic syndrome (α-glucosidase, α-amylase, pancreatic lipase). The chemical profiles were analyzed by HPLC-DAD. Higher antioxidant activity in the ORAC and CUPRAC assay was found for the landrace Coscorrón, and the best effect in the TEAC for Sapito, respectively. The main phenolics were flavonol glycosides and caffeic acid derivatives. The extracts presented strong activity against α-glucosidase, but were inactive towards α-amylase and pancreatic lipase. The leaf extract from the Sapito landrace was fractionated to isolate the main α-glucosidase inhibitors, leading to caffeoylmalic acid with an IC50 of 0.21 µg/mL. The HPLC fingerprints of the leaves differentiate three groups of chemical profiles, according to the main phenolic content. A significant correlation was found between the α-glucosidase inhibition, the content of caffeoylmalic acid (r = -0.979) and kaempferol 3-O-ß-D-glucoside (r = 0.942) in the extracts. The presence of α-glucosidase inhibitors in the leaves of Chilean beans support their potential as a source of bioactive compounds.

Iridoids and polyphenols from chilean Gaultheria spp. berries decrease the glucose uptake in Caco-2 cells after simulated gastrointestinal digestion.

Berries are rich food sources of potentially health-beneficial (poly)phenols. However, they may undergo chemical modifications during gastrointestinal digestion. The effect of simulated gastrointestinal digestion on the content and composition of secondary metabolites from Gaultheria phillyreifolia and G. poeppigii berries was studied. The influence of the digested extracts on the in vitro metabolism and absorption of carbohydrates was evaluated. After simulated digestion, 31 compounds were detected by UHPLC-DAD-MS. The total content of anthocyanins decreased by 98-100%, flavonols by 44-56%, phenylpropanoids by 49-75% and iridoids by 33-45%, the latter showing the highest stability during digestion. Digested extracts inhibited α-glucosidase (IC50 2.8-24.9 µg/mL) and decreased the glucose uptake in Caco-2 cells by 17-28%. Moreover, a decrease in the mRNA expression of glucose transporters SGLT1 (38-92%), GLUT2 (45-96%), GLUT5 (28-89%) and the enzyme sucrase-isomaltase (82-97%) was observed. These results show the effect of simulated gastrointestinal digestion on the content and composition of Gaultheria berries.

The use of medicinal plants by Paraguayan migrants in the Atlantic Forest of Misiones, Argentina, is based on Guaraní tradition, colonial and current plant knowledge.

ETHNOPHARMACOLOGICAL RELEVANCE: Information on the use of medicinal plants in the daily life by Paraguayan people is scarce in mainstream scientific literature. The study on the Paraguayan diaspora in the Provincia de Misiones, Argentina, gives an insight into Guaraní traditions, colonial legacy and current search for new medicinal plants to address new health challenges. AIM OF THE STUDY: To document the use of medicinal plants by Paraguayan mestizo migrants who moved into a new country, yet within the same ecological region. The present and past uses of medicinal plants were compared to understand the continuity and change in the Paraguayan herbal pharmacopoeia. MATERIALS AND METHODS: Fieldwork based on ethnographic and ethnobotanical techniques was carried out in the Provincia de Misiones, Argentina, in 2014, 2015, and 2019. Eighty-five Paraguayan migrants and their descendants from eastern Paraguay took part in the study. The list of recorded plants was compared with the information in historical sources from Paraguay, to examine the continuity and changes in Paraguayan herbal medicine, and with the present-day ethnobotanical studies from Paraguay. Ethnopharmacological and phytochemical studies on the medicinal plants with the highest consensus of uses were reviewed. RESULTS: Altogether, 204 medicinal plant species were recorded. The most frequently mentioned species represented a combination of plants native to the New and Old World. Nearly 40% of the present-day Paraguayan pharmacopoeia shows continuity from colonial and post-colonial periods. Plants were used for 19 medical categories, of which digestive, circulatory and those belonging to humoral medicine were the most prevalent. The ongoing search of plants to treat new health problems is illustrated by reports of 40 species used for hypertension, 26 for diabetes and 18 to lower cholesterol. There is still little evidence for the effectiveness of these plants in the pharmacological literature. Paraguayan migrants were able to continue their traditional plant medicine in Misiones, Argentina, in a substantial way. CONCLUSION: This study was carried out in a geographic area with a long-standing tradition of Guaraní medicine. Paraguayan migrants in Misiones integrate pre-Hispanic Guaraní names and uses of plants and old humoral concepts with current adaptation of plants to meet new health challenges. Several of the uses described in early colonial times are still practiced, giving a solid background for in-depth studies of the local pharmacopoeia.

Seasonal Variation of Plant Defense Inductor Ellagitannins in Strawberry Leaves under Field Conditions for Phytosanitary Technological Applications.

Many natural compounds can activate the plant immunity, and for this reason, they have attracted special interest in crop disease management. Previously, we isolated from strawberry leaves an ellagitannin (HeT), which elicits plant defense responses. In this research, we investigated bioactive compounds from field-collected strawberry leaves capable of inducing defense responses in Arabidopsis thaliana against a bacterial pathogen. Methanolic extracts of strawberry leaves sampled at different months were obtained and compared. The highest content of total soluble phenolic compounds was found in the methanolic extracts of leaves sampled in December (DME). The defense response induced in A. thaliana by DME was attributed to two ellagitannins, the HeT and galloyl-HHDP-glucose. Both compounds exhibited phytoprotective effects against Pseudomonas viridiflava and induced the expression of PDF1.2 and PR1 genes. These results provide an economic value to strawberry leaves, normally discarded at the end of the harvest stage of the crop, as a raw material for plant health enhancer bioinputs.

Antiglycating Effect of Phenolics from the Chilean Currant Ribes cucullatum under Thermal Treatment.

Numerous dietary polyphenols possess antiglicating activity, but the effects of thermal treatment on this activity are mostly unknown. The effect of thermal treatment in the antiglycating activity of polyphenolic enriched extracts (PEEs) from Ribes cucullatum towards glyoxal-induced glycation of sarcoplasmic proteins was assessed. Sarcoplasmic proteins from chicken, beef, salmon, and turkey, were incubated 2 h at 60 °C with and without glyoxal and different concentrations of PEEs (0.25, 0.5, 1, and 5 mg/mL). The antiglycating activity was evaluated by: (1) Lys and Arg consumption, (2) Carboxymethyl lysine (CML) generation, and (3) lipid-derived electrophiles inhibition in a gastric digestion model. Protective effects were observed against CML generation in proteins and a decrease of electrophiles in the gastric digestion model. A dose-dependent consumption of Lys and Arg in proteins/PEEs samples, indicated the possible occurrence of quinoproteins generation from the phenolics. Protein/PEEs incubations were assessed by: (1) High pressure liquid chromatography analysis, (2) Gel electrophoresis (SDS-PAGE), and (3) Redox cycling staining of quinoproteins. Protein/PEEs incubations produced: (1) Decrease in phenolics, (2) increase of protein crosslinking, and (3) dose-dependent generation of quinoproteins. We demonstrate that phenolic compounds from R. cucullatum under thermal treatment act as antiglycating agents, but oxidative reactions occurs at high concentrations, generating protein crosslinking and quinoproteins.

Phenolic composition, antioxidant capacity and α-glucosidase inhibitory activity of raw and boiled Chilean Araucaria araucana kernels.

The Araucaria araucana kernels are a traditional food in southern Chile and Argentina. The aim of this work was to determine the composition of the phenolic-enriched extracts (PEEs) of the boiled kernels as well as their antioxidant capacity, inhibitory activity on metabolic syndrome-associated enzymes and effect on postprandial oxidative stress in a simulated gastric digestion model. The PEEs composition was assessed by HPLC-DAD-MS/MS. The main PEEs constituents were catechin and epicatechin in the unbound form, while hydroxybenzoic acids occurred mainly in the bound form. The unbound phenolics from boiled kernels showed significant correlations with DPPH, FRAP, TEAC (Pearson's r of 0.481, 0.331 and 0.417, respectively) and lipid peroxidation (r = 0.381) and were more active than the bound phenolics. The extracts were highly active against α-glucosidase (IC50: 0.33-3.15 µg/mL) and reduced lipoperoxidation. Traditional processing increases the flavan-3-ol content. Our results suggest that this traditional food has potential health promoting properties.

Phenolics from the Bolivian highlands food plant Ombrophytum subterraneum (Aspl.) B. Hansen (Balanophoraceae): Antioxidant and α-glucosidase inhibitory activity.

The Balanophoraceae Ombrophytum subterraneum is an endemic highland food plant occurring in Bolivia, northern Argentina and Chile. The upper part of this parasitic plant is eaten fresh. The aim of this work was to characterize the compounds occurring in the edible part and to assess any differences between the inflorescence and tuber. Ethanol extracts of the different plant parts were analyzed for antioxidant activity by the ORAC, TEAC, FRAP, CUPRAC and DPPH methods as well as for the effect on enzymes related to metabolic syndrome (α-amylase, α-glucosidase and pancreatic lipase). The main constituents were isolated by a combination of gel permeation in Sephadex LH-20 and countercurrent chromatography (CCC). Five compounds were isolated and fully identified by spectroscopic and spectrometric means. The new 3',5,5',7-tetrahydroxyflavanone 7-O-ß-D-1 â†’ 6 diglucoside was isolated for the first time. HPLC-ESI-MS/MS analysis allowed the identification of 19 compounds, including flavanones, flavanols, flavonols, dehydroflavonols and lignans, mainly as glycosides. A strong inhibition towards α-glucosidase was observed for the edible parts (IC50: 1.46 µg/mL) as well as for the tuber and inflorescence (IC50: 1.56 µg/mL and 0.87 µg/mL, respectively). A significant correlation was established between the total phenolic and the antioxidant capacity of the extracts as well as with the content of the new flavanone diglucoside. This is the first comprehensive report on the naturally occurring antioxidants and enzyme inhibitors from this native highland food resource.

The Parotoid Gland Secretion from Peruvian Toad Rhinella horribilis (Wiegmann, 1833): Chemical Composition and Effect on the Proliferation and Migration of Lung Cancer Cells.

Since Rhinella sp. toads produce bioactive substances, some species have been used in traditional medicine and magical practices by ancient cultures in Peru. During several decades, the Rhinella horribilis toad was confused with the invasive toad Rhinella marina, a species documented with extensive toxinological studies. In contrast, the chemical composition and biological effects of the parotoid gland secretions (PGS) remain still unknown for R. horribilis. In this work, we determine for the first time 55 compounds from the PGS of R. horribilis, which were identified using HPLC-MS/MS. The crude extract inhibited the proliferation of A549 cancer cells with IC50 values of 0.031 ± 0.007 and 0.015 ± 0.001 µg/mL at 24 and 48 h of exposure, respectively. Moreover, it inhibited the clonogenic capacity, increased ROS levels, and prevented the etoposide-induced apoptosis, suggesting that the effect of R. horribilis poison secretion was by cell cycle blocking before of G2/M-phase checkpoint. Fraction B was the most active and strongly inhibited cancer cell migration. Our results indicate that the PGS of R. horribilis are composed of alkaloids, bufadienolides, and argininyl diacids derivatives, inhibiting the proliferation and migration of A549 cells.

Synthesis, trypanocidal and anti-leishmania activity of new triazole-lapachol and nor-lapachol hybrids.

A new library of twenty triazole-lapachol and nor-lapachol derivatives was synthesized. The compounds were evaluated against the epimastigotes form of Trypanosoma cruzi and promastigotes of Leishmania braziliensis and L. infantum. The cytotoxicity of the compounds was determined on murine fibroblasts and used to assess the selectivity index. The introduction of triazole rings in the naphthoquinone derivatives improved activity against the parasitic protozoa T. cruzi and Leishmania species. Some of the derivatives were three to six times more potent than benznidazole against T. cruzi, with similar or slightly better selectivity indexes. The results against L. braziliensis showed that the derivatives 5b and 5e were the most selective compounds. However, they were less selective than the reference compound, miltefosine. Among all products, the derivative 3a was the most selective compound against L. infantum. Nevertheless, it was less potent and less selective than miltefosine. Also, the minimum inhibitory concentration values of the derivatives against nine different bacteria were determined. Moderate antibacterial activity was observed for compound 5c against Staphylococcus aureus.

Isolation and characterization of secondary metabolites from Gaultheria tenuifolia berries.

Gaultheria berries (Ericaceae) are consumed as food or used in folk medicine throughout the world. In the present study, Gaultheria tenuifolia berries were studied to describe their polyphenol and iridoid composition, aroma volatiles, and cytoprotective effects. In total, 14 metabolites were isolated using a combination of countercurrent chromatography and Sephadex LH-20, namely, cyanidin-3-O-ß-galactoside, cyanidin-3-O-ß-arabinoside, 3-O-caffeoylquinic acid, 5-O-caffeoylshikimic acid, quercetin, quercetin-3-O-ß-glucuronide, quercetin-3-O-ß-rutinoside, quercetin-3-O-ß-glucoside, quercetin-3-O-ß-arabinoside, quercetin-3-O-ß-rhamnoside, 6α-hydroxydihydromonotropein-10-trans-cinnamate, monotropein-10-trans-cinnamate, and an (epi)-catechin dimer and trimer. Other flavan-3-ols, proanthocyanidins, and iridoids were tentatively identified by spectroscopic and spectrometric means in the fruit extracts. The tentative volatile organic compound characterization pointed to methyl salicylate as responsible for the aroma of this species. The extracts showed significant cytoprotective effects in an oxidative stress model in human gastric epithelial cells. This is the first report on the isolation, characterization, and potential biological activity of secondary metabolites from G. tenuifolia berries and insights on its possible application as a functional food. PRACTICAL APPLICATION: Berries are desirable fruit species because of their phytochemical composition and pleasant taste. Gaultheria berries are special due to their high content of iridoids and the presence of salicylic acid derivatives. Aroma of native berries is relevant for the development of new products reflecting the local identity and use of fruits. The present work involves cooperation of academia and industry on the constituents of the native products. The results provided in this article could be useful for the introduction of this species in the food and nutraceutical industries.

A cyclic dipeptide from the Chilean hazelnut cotyledons (Gevuina avellana Mol., Proteaceae).

The Chilean hazelnut (Gevuina avellana Mol., Proteaceae) is a southern South American nut consumed as a snack and included in different preparations of traditional Chilean cuisine. Recently we described the fatty acid profile, oxylipins, phenolic compounds, as well as the antioxidant capacity. The main compounds of the phenolic-enriched extract were only tentatively identified by spectrometric means. In the present work, we describe the isolation and full characterization of a cyclic dipeptide cyclo(Arg-Trp) and other compounds from the phenolic enriched extracts of the G. avellana cotyledons. Compounds were isolated by means of counter-current chromatography and structures were established by spectroscopic and spectrometric methods. This is the first report on small peptides in G. avellana and adds evidence on the possible beneficial effects of this nut in human health.

Integral use of Argentinean Solanum betaceum red fruits as functional food ingredient to prevent metabolic syndrome: effect of in vitro simulated gastroduodenal digestion.

The "red chilto" (Solanum betaceum Cav) is a native fruit from the Yungas forest of Argentina. Red chilto is a neglected and underutilized native species (NUS). The objective of this work was to evaluate the potentiality of pulp, seed and skin from "red chilto" as a functional food ingredient to add value to a native resource of Argentine Yungas to promote sustainable integral use of it. The powders have low carbohydrate and sodium content and are a source of vitamin C, phenolic acids (rosmarinic acid and caffeoylquinic acid), anthocyanins, condensed tannins, carotenoids, potassium, and fiber. The phenolics of chilto powders showed, before and after simulated gastroduodenal digestion, antioxidant activity (ABTS•+; H2O2; O2 •; HO•) and were able to inhibit enzymes related to metabolic syndrome, such as α-glucosidase, α-amylase and lipase. Chilto powder showed hypoglycemic effect by increasing glucose adsorption, decreasing glucose diffusion rate and by promoting glucose transport across the cell membrane. These results suggest the potential of Argentinean "red chilto" fruits as functional food ingredients or dietary supplements to prevent metabolic syndrome principally by its antioxidant, hypoglycemic and hypolipemic effects.