Common beans contain insoluble-bound phenolic compounds with potential bioactive properties; however, their recovery generally depends on harsh hydrolytic conditions and organic solvents. This study evaluated alternative extraction strategies for the recovery of insoluble-bound phenolic compounds from raw and cooked common bean flours of two Andean varieties (Peumo and Magnum), using Viscozyme L®, ultrasound, and pretreatment with ultrasound followed by Viscozyme L®. The resulting extracts were characterized in terms of phenolic profile by UPLC-ESI-MS/MS, total phenolic content (TPC), and antioxidant activity. Enzymatic treatment improved the recovery of insoluble-bound phenolic compounds and antioxidant activity compared with the control, while ultrasound alone showed limited effectiveness under the evaluated conditions. The combination of ultrasound pretreatment and Viscozyme L® generally improved recovery of some phenolic compounds and antioxidant-related endpoints relative to control conditions. Cooking generally reduced TPC and antioxidant activity, although the effect on individual phenolic compounds depended on the extraction treatment. Overall, enzyme-assisted extraction, especially when combined with ultrasonic pretreatment, represents a promising strategy for improving the recovery of insoluble phenolic compounds from common bean flour. Further optimization is still needed to improve the sustainability of the process and its industrial applicability.

Common beans are one of the primary legumes consumed worldwide. This study addressed the phenolic profile (UPLC-ESI–MS/MS), total phenolic content (TPC), and antioxidant activity (AA) of insoluble-bound enriched flours (IBEF) obtained from Andean common bean varieties (Peumo, Magnum, and Mantequilla). Phenolic acids were the predominant compounds in the Mantequilla variety, while flavonoids (catechin/epicatechin) were more prevalent in the Magnum and Peumo. The Peumo variety had the highest TPC and AA. Furthermore, cooking influenced the phenolic profile and TPC differently across varieties, but it generally reduced AA. This study is the first to characterize the insoluble phenolic profile in both raw and cooked samples of these three common bean varieties, revealing differences in phenolic profiles and antioxidant activities among varieties and underscoring the variable effects of cooking on the phenolic composition and content, with an overall negative impact on AA.

The common bean (Phaseolus vulgaris L.) is an important dietary legume and a source of triterpenoid saponins, compounds associated with both nutritional and biological activities. Despite numerous reports describing bean saponin profiles by mass spectrometry, the isolation and full structural characterization of individual saponins remain limited, particularly for landrace varieties. In this study, the major saponins present in a Chilean P. vulgaris landrace ('Azufrado') were isolated and structurally characterized. A secondary metabolite-enriched extract was prepared from bean seeds and fractionated using Sephadex LH-20 gel permeation followed by HPLC with DAD and ELSD detection for peak assignment and DAD-guided fraction collection. Six saponins were obtained and analyzed by mass spectrometry and extensive one- and two-dimensional NMR spectroscopy. Two monodesmosidic soyasaponins were identified as soyasaponin V (Ba) and soyasaponin I (Bb), both based on a soyasapogenol B aglycone. Two additional fractions contained minor DDMP-conjugated derivatives of these saponins, supported by diagnostic NMR signals and accurate mass measurements. In addition, two bidesmosidic saponins were identified as phaseoside I and sophoraflavoside I based on exact mass, fragmentation patterns, and comparison with reported data. This work provides structural confirmation of major common bean saponins and expands the chemical characterization of P. vulgaris landraces, supporting future studies on their stability, metabolism, and bioactivity.

Background/Objectives: Jatrophone is a bioactive diterpenoid with reported antitrypanosomal activity; however, its development as a lead compound is limited by pronounced cytotoxicity toward mammalian cells. This study aimed to explore the structural modification of jatrophone through triazole functionalization to modulate its antiparasitic activity and improve selectivity against Trypanosoma cruzi. Methods: A series of mono- and bis-triazole jatrophone derivatives was semi-synthesized via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) from a stereoselectively prepared diazido intermediate. Jatrophone, its azido precursor, and the synthesized triazole derivatives were evaluated in vitro against T. cruzi epimastigotes and intracellular amastigotes. Cytotoxicity toward mammalian host cells was assessed in parallel to determine selectivity indices. Results: Jatrophone exhibited potent activity against epimastigotes but showed poor selectivity due to significant mammalian cell toxicity. Introduction of azide and triazole functionalities altered the biological profile of the parent scaffold, leading to derivatives with reduced cytotoxicity and improved selectivity in extracellular assays. Among the evaluated compounds, a mono-triazole derivative bearing a methylene-linked cycloalkyl substituent retained antiparasitic activity while displaying markedly lower toxicity toward mammalian cells. However, in the intracellular amastigote model, most derivatives demonstrated a substantial reduction in selectivity, indicating limited translation of extracellular activity to the intracellular parasite stage. Conclusions: Triazole functionalization of the jatrophone scaffold represents a viable strategy to modulate its biological properties and reduce host-cell toxicity. Nevertheless, the reduced efficacy observed in intracellular assays underscores the limitations of epimastigote-based screening and highlights the challenges in developing selective intracellular antitrypanosomal agents from the jatrophone scaffold.

The objective of this study was to obtain and characterize bioactive peptides derived from common bean (Phaseolus vulgaris) landraces and to evaluate their antioxidant potential using multiple in vitro assays. Protein isolates were obtained by isoelectric precipitation followed by enzymatic hydrolysis using Alcalase. Peptides were separated by ultrafiltration into fractions < 3 kDa and 3-10 kDa, yielding a total of forty samples. Antioxidant activity was evaluated using DPPH, FRAP, and ORAC assays. Antioxidant responses ranged from 13.06 to 50.8% inhibition in DPPH, 52.2 to 1750 µmol TE/100 g in FRAP, and 305 to 5246 µmol TE/100 g in ORAC. Resistance against oxidation ranged from 10.6 to 68.8%. Peptides < 3 kDa generally exhibited higher antioxidant activity in the functional assays, particularly in the Apolo, Magnum, Boloto, and Hallado landraces, although some 3-10 kDa fractions also showed relevant activity. Peptide extraction yields ranged from 3.73 to 10.39% and from 1.33 to 4.74%, while soluble protein contents ranged from 23.1 to 460 and from 9.9 to 288 mg BSA/100 g beans for <3 kDa and 3-10 kDa fractions, respectively. Overall, the results support the potential of common bean-derived peptides as functional food ingredients with antioxidant activity mediated through multiple mechanisms.

Previous studies indicate that the alkali-induced oxidation of quercetin (Que) or kaempferol (Kae) converts them into hydroxylated-benzoyl-benzofuranones (BZFs), a type of metabolite whose antioxidant potency is substantially higher. To explore whether the former conversion can take place under a more biologically relevant oxidizing setting, these flavonols were incubated in a nitrite-containing acidic medium. Under such condition, the concentrations of Que or Kae rapidly decayed, simultaneously generating their corresponding BZFs. When Que and Kae were co-incubated, the depletion of the parent flavonols accelerated without changes in BZF formation. Similar results were observed when either Que or Kae were incubated with some of their corresponding 3-O-glycosides. In turn, when Que was co-incubated with certain flavanols or phenolic acids, the latter compounds nearly doubled not only the oxidative disappearance of Que but also its BZF formation. Interestingly, the concentrations of Que-BZF and Kae-BZF reached under all former incubation scenarios are greater than those previously reported to be needed to protect intestinal epithelial cells against the oxidative and lytic damage induced by ROS. We suggest that, if these conversions also took place in vivo, the gastric fluid could be potentially seen as a chemical milieu where the antioxidant properties of Que and Kae could be enormously amplified.

The seed oil composition of South American cucurbits, including the Chilean giant pumpkin (Cucurbita maxima) and the Paraguayan Sicana odorifera, was assessed by high-field nuclear magnetic resonance (NMR). The main objective of the study was to describe the composition of the seed oils using NMR as the main analytical tool and to detect possible conjugated linolenic acid isomers (CLnA). A previous study of S. odorifera seed oil identified linolenic and linoleic acids as the main fatty acids (FAs). Reexamination of the S. odorifera seed oil by NMR showed that the C18:3 fatty acid previously reported is the CLnA isomer punicic acid (PA). PA occurs in S. odorifera cultivars atropurpurea and fragans, with higher content in atropurpurea (37.42 and 31.70%, respectively). The identification of PA as a major constituent in S. odorifera oil opens new perspectives on the possible applications and consumption of seeds as a healthy food. The new source of PA is a fast-growing cucurbit, adapted to tropical and subtropical climates. The seed oil composition of the Chilean giant pumpkin is like that of other C. maxima cultivated in South America and Europe. NMR spectroscopy was a rapid and reliable method for identifying and quantifying the main constituents in the seed lipids, clearly differentiating CLnA isomers and linolenic acid.

‘Loche’ squash (Cucurbita moschata) is an ancient cucurbit landrace from northern Peru, with deep cultural roots in the Moche cuisine tradition. To our knowledge, this is the first study to combine phytochemical profiling of raw and cooked pulp with standardized in vitro gastrointestinal digestion and intestinal cell-based assessment in this matrix. This study assessed the carotenoid, tocopherol, and (poly)phenol composition of raw and boiled pulp, evaluated bioaccessibility through standardized in vitro gastrointestinal digestion (INFOGEST), and investigated the effects of the bioaccessible fraction on intracellular glutathione levels in a Caco-2:HT29-MTX-E12 co-culture model. UHPLC-DAD-MS² tentatively identified 16 phytochemicals, including phenolic and hydroxycinnamic acids, coumarin, and glycosylated derivatives. Lutein and α-tocopherol were the predominant carotenoid and tocopherol in raw pulp, respectively. Boiling substantially reduced all quantified phytochemicals, with tocopherols showing the greatest losses (77–93

Tofu from six different landraces of chilean common beans (Araucano, Cimarrón, Magnum, Peumo, Sapito, and Tortola) was prepared and analyzed for proximate and lipid composition, antioxidant capacity, and phenolic content. Tofu has higher protein and lipid content, lower carbohydrate and phenolic content, and shows antioxidant capacity. The highest total protein was found for tofu prepared from Cimarrón and Sapito beans. The main phenolics in the secondary metabolite-enriched extract of the tofu were kaempferol 3-O-glucoside and kaempferol. Nuclear magnetic resonance (NMR) analyses showed that most lipids from the beans and tofu were unsaturated fatty acids triglycerides.

Infusions of the leaves of Ribes magellanicum (Grossulariaceae) are used as a digestive in southernmost South America. This work aimed to assess the composition and activity of infusions and MeOH:H2O 7:3 extracts of R. magellanicum leaves on enzymes related to metabolic syndrome (α-glucosidase, α-amylase, and pancreatic lipase), as well as their antioxidant capacity. Samples from a longitudinal gradient from central southern Chile to the islands in the Beagle Channel were investigated. Lyophilized infusions and extracts were used for all determinations, including inhibition of the selected enzymes, total phenolic (TP), total flavonoid (TF), total procyanidins (TPC), and antioxidant capacity (DPPH, FRAP, TEAC, and ORAC). The composition of the samples was assessed by HPLC-DAD. Some 99 compounds were tentatively identified by HPLC-MSn. The main phenolics were quantified using calibration curves with reference compounds. Relevant differences exist in the ratio of constituents in infusions compared to hydroalcoholic extracts. The samples were inactive towards α-amylase and pancreatic lipase at 100 and 50 µg/mL, respectively. Assay-guided isolation of α-glucosidase inhibitors led to fractions with high activity (IC50: 0.02–0.05 µg/mL). The strong inhibition of α-glucosidase and antioxidant capacity of the infusion and extracts of R. magellanicum leaves support its traditional use in southern Patagonia.

SCOPE:We report a nutritional intervention involving supplementation with boiled beans and secondary metabolites-enriched extracts (SMEEs) from a Chilean Phaseolus vulgaris landrace in mice with induced metabolic syndrome (MS). METHODS AND RESULTS:The effects of supplementation were assessed in C57BL6 mice with MS induced by a high-fat diet. Boiled beans (75 and 150 mg animal day-1) and the SMEE (0.8 and 8 mg animal day-1) were administered daily for 4 months. Weight and glycemia were measured weekly. At the end of the experiment, glycemia, total, high-density lipoprotein (HDL) and low-density lipoprotein (LDL) cholesterol, triglycerides, protein carbonyls, and carboxymethyl lysine (CML) levels were determined in plasma. Oral intake of the SMEE decreased glycemia at the end of the intervention. No statistically significant difference in glycemia was found for the boiled beans compared with controls. The SMEE at 0.8 mg animal day-1 decreased the total amount of CML, mainly in proteins with molecular masses >75 kDa, in agreement with the results for carbonylated proteins. CONCLUSION:The SMEE of Peumo beans reduces glycemia at the end of the intervention and decreases total CML in plasma, suggesting a potential beneficial effect of bean intake. The results obtained in the intervention encourage further studies in Chilean bean landraces.

The pods from the Capparaceae Cynophalla retusa were consumed by the Chaco Amerindians in Paraguay. This study aimed to characterize the compounds present in the secondary metabolite-enriched extract (SMEE) from processed pods and to assess the effect of the SMEE on enzymes associated with metabolic syndrome. The enzymes included α-glucosidase, α-amylase, and pancreatic lipase. Acute toxicity in Swiss albino mice and immunomodulatory effect on murine splenocyte proliferation induced by concanavalin A were determined. Proximate composition analyses were performed using AOAC methods. The fatty acid profile was determined by gas chromatography and NMR. The total phenolic content and antioxidant capacity were measured using the ABTS and ORAC methods. The lipids in the seeds were monounsaturated (39.46±0.54 g/100 g oil) and saturated (38.02±0.45g/100 g oil) fatty acids. The processed pods exhibit a high protein content and dietary fiber. Some 33 compounds, including alkaloids, phenolics, and fatty acid derivatives, were identified in the pods. The extracts showed α-glucosidase inhibition and immunomodulatory activity. This is the first comprehensive report on the secondary metabolites, acute toxicity, and immunomodulatory effects in processed pods of C. retusa from the Paraguayan Chaco. The results highlight the potential of this underutilized species for food security and global health.

This study examines the effects of three Chilean boiled bean (Phaseolus vulgaris L.) landraces 'Negro', 'Peumo', and 'Tórtola' and their polyphenol-enriched extracts (PEE) on polyphenol release, gut microbiota, and short-chain fatty acid (SCFA) production after simulated digestion and colonic fermentation. Negro beans exhibited greater phenolic acid diversity post-digestion, while catechin bio accessibility increased in all landraces. PEE showed significant transformation, with oligomers degrading into flavan-3-ol monomers during digestion. Colonic fermentation of boiled beans produced SCFAs, confirming their prebiotic potential. Negro beans promoted beneficial bacteria, including Catenibacterium, Lachnospira, and Bifidobacterium, associated with fiber and polyphenol metabolism, while Tórtola beans favored Roseburia, an SCFA producer. These findings highlight the potential of Chilean beans and their bioactive compounds to enhance gut health.

The Andean domesticated common beans (Phaseolus vulgaris) are significant sources of phenolic compounds associated with health benefits. However, the regulation of biosynthesis of these compounds during bean seed development remains unclear. To elucidate the gene expression patterns involved in the regulation of the flavonoid pathway, we conducted a transcriptome analysis of two contrasting Chilean varieties, Negro Argel (black bean) and Coscorron (white bean), at three developmental stages associated with seed color change, as well as different flavonoid compound accumulations. Our study reveals that phenolic compound synthesis initiates during seed filling, although it exhibits desynchronization between both varieties. We identified 10,153 Differentially Expressed Genes (DEGs) across all comparisons. The KEGG pathway ‘Flavonoid biosynthesis’ showed enrichment of induced DEGs in Negro Argel (PV172), consistent with the accumulation of delphinidin, petunidin, and malvidin hexosides in their seeds, while catechin glucoside, procyanidin and kaempferol derivatives were predominantly detected in Coscorrón (PV24). Furthermore, while the flavonoid pathway was active in both varieties, our results suggest that enzymes involved in the final steps, such as ANS and UGT, were crucial, inducing anthocyanin formation in Negro Argel. Additionally, during active anthocyanin biosynthesis, the accumulation of reserve proteins or those related to seed protection and germination was induced. These findings provide valuable insights and serve as a guide for plant breeding aimed at enhancing the health and nutritional properties of common beans.

The small fruits from Empetrum rubrum were consumed by Native Americans in southern Patagonia. Two samples collected close to the Magellan Street and the Beagle channel in Tierra del Fuego were investigated. Three different extracts from the berries were analyzed, namely: methanol, phenolic-enriched (PEE) and ethyl acetate (EtOAc). The total phenolic, flavonoid, procyanidin and anthocyanin content of the extracts was determined. The effect of the extracts towards the metabolic syndrome-associated enzymes alpha-glucosidase, alpha-amylase and pancreatic lipase was assessed. In addition, the antioxidant capacity was measured using DPPH, FRAP, TEAC and ORAC assays. The composition of the extracts was determined by HPLC-MS/MS. Seventy-one compounds were identified for the first time in the berries, including 10 anthocyanins, 35 flavonoids, 11 phenylpropanoids and 13 procyanidins. The main compounds were quantified by HPLC-DAD. The extracts displayed strong activity as alpha-glucosidase inhibitors, with IC50 values ranging from 0.10 to 0.19 mu g/mL for the PEE and 0.82-1.95 mu g/mL for the EtOAc extracts, respectively. The results show high chemical diversity and differences with the boreal species E. nigrum.

Herbal teas are used in South Africa as digestives to lower glycaemia and for other indications. However, the chemical composition of the infusions and their effect on enzymes related to metabolic syndrome is poorly known. The composition of infusions and methanol extracts of B. saligna (Scrophulariaceae), Lippia javanica, L. scaberrima, and Phyla dulcis (Verbenaceae) was assessed and the effect of the infusions and extract was determined towards α-glucosidase, α-amylase, and pancreatic lipase. The commercial herbal products were extracted separately with MeOH or hot water to obtain the extract/infusion for comparative studies. Total phenolic, total flavonoid and antioxidant capacity were assessed. The fingerprints of the MeOH extracts and infusions were compared by HPLD-DAD. The extract constituents were tentatively identified by HPLC-MS/MS and NMR analyses. From the extracts/infusions, 57 compounds were identified, including iridoids, phenylpropanoid glycosides, flavonoids, and caffeic acid derivatives, among others. The MeOH extracts and infusions showed strong inhibition towards α-glucosidase with IC50 in the range of 0.13–0.84 µg/mL for the phenolic-enriched infusion extract (PEI) and 0.47–0.50 µg/mL for the MeOH extracts, respectively. The P. dulcis PEI showed higher inhibition towards α-glucosidase, and the MeOH extract of L. scaberrima was better than the PEI. At 100 µg/mL, the PEI from the four herbal teas reduces the activity of α-amylase by 23.03–28.61%, with L. javanica as the most active tea. Three of the species are high in phenylpropanoid glycosides, while P. dulcis contains rosmarinic acid. Some 26 compounds were identified in the infusion from B. saligna, 28 from L. scaberrima, and 21 from P. dulcis. Four of them are common in all the teas, namely decaffeoylverbascoside, verbascoside, isoverbascoside, and tuberonic acid hexoside. Ten compounds occur in two of the teas and seventeen, fifteen, and eleven compounds were detected only in B. saligna, L. scaberrima, and P. dulcis, respectively. Most of the compounds are reported for the first time from the crude drug infusions. The results give some support for the traditional use of herbal teas as digestives and/or indications for diabetes. The chemical fingerprints set the basis for quality control of the crude drugs, based on the main constituents and differential compounds occurring in the samples.

The influence of oxygen on the thermal treatment (TT) of secondary metabolite-enriched extracts (SMEEs) from Tórtola beans and procyanidin C1 (PC1) on the inhibition of advanced glycation end products (AGEs) generation in proteins was investigated. SMEE was incubated at 4 °C (control) or thermally treated at 60 °C for 2 h, at either 0 % O2 (I) or 20 % O2 (II). Treatments I and II increased the content of procyanidin dimers B2. Treatment II was more effective than the control or treatment I in preventing homocysteine oxidation and AGEs generation. TT of PC1 at 0 % or 20 % O2 generated procyanidin dimers and tetramers. PC1 TT at 20 % O2 exhibited higher oxidation potentials and lower IC50 values of fluorescent AGEs than those of controls or TT at 0 % O2. These findings indicate that SMEE from Tórtola beans after treatment II changes the degree of polymerization and oxidation procyanidins, thereby increasing their antiglycation activity.

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.

Background/Objectives: In this study, the efficacy of benzo[h]chromene derivatives as antiprotozoal and antimycobacterial agents was explored. Methods: A total of twenty compounds, including benzo[h]chromene alkyl diesters and benzo[h]chromene-triazole derivatives, were synthesized and tested against Trypanosoma cruzi, Leishmania braziliensis, L. infantum, and strains of Mycobacterium abscessus and Mycobacterium intracellulare LIID-01. Notably, compounds 1a, 1b, 2a, and 3f exhibited superior activity against Trypanosoma cruzi, with IC50 values of 19.2, 37.3, 68.7, and 24.7 µM, respectively, outperforming the reference drug benznidazole (IC50: 54.7 µM). Results: Compounds 1b and 3f showed excellent selectivity indices against Leishmania braziliensis, with SI values of 19 and 18, respectively, suggesting they could be potential alternatives to the commonly used, but more selective, miltefosine (IC50: 64.0 µM, SI: 43.0). Additionally, compounds 1a, 1b, and 3f were most effective against Leishmania infantum, with IC50 values of 24.9, 30.5, and 46.6 µM, respectively. Compounds 3f and 3h were particularly potent against various Mycobacterium abscessus strains, highlighting their significance given the inherent resistance of these bacteria to standard antimicrobials. Conclusions: The sensitivity of Mycobacterium intracellulare LIID-01 to these compounds also underscored their potential in managing infections by the Mycobacterium avium–intracellulare complex.

Neltuma nigra seed and cotyledon flours were prepared and characterized.