The genus Ocotea of the Lauraceae family has species whose wood is employed in construction and for other purposes including as biofuel, for disinfection, cosmetics, and in the treatment of various diseases. Studies regarding Ocotea caudata’s phytochemical and pharmacognostic uses are scarce, thus, this work is the first to study its fruits. O. caudata (Nees) Mez fruits from Colombia were investigated for their oil content. Heptane extraction from O. caudata fruit oil yielded 54.9 % of total lipids, where the fatty acid composition was determined. The oil analysis by gas chromatography with flame ionization detection (GC-FID) demonstrated that lauric acid was the most abundant fatty acid (51.7 %, C12:0). In addition to lauric acid, oleic acid (23.6 %, C18:1) and palmitic acid (16.6 %, C16:0) were found. The fatty acid composition was confirmed by gas chromatography-mass spectrometry (GC-MS). O. caudata can be considered as a species that accumulates medium-chain saturated fatty acids (C12) and long-chain unsaturated fatty acids (C18). In conclusion, many of its health benefits may be due to its high content of lauric acid. Therefore, this oil is highly regarded for its nutritional and health properties.

Abnormal production of reactive oxygen species (ROS) has been implicated in the physiopathology of neuronal cell death. Increased ROS levels are associated with exacerbated peptide aggregation, inflammation, and mitochondrial dysfunction, which facilitate the triggering of specific cell death pathways. Antioxidant molecules are potentially useful in the amelioration of neurodegeneration. In this regard, natural products are an invaluable source of antioxidants. Therefore, we investigate the antioxidant and neuroprotective activities of four Colombian angiosperm extracts. Antioxidant activity was evaluated by phytochemical assays using TLC techniques with Dragendorff reagent, ninhydrin, and chloranil in dioxane, NH3, Fast Blue, and FeCl3, together with bioautography using DPPH and β-carotene. In vitro neuroprotective activity, cell death, and ROS accumulation were evaluated by MTT and flow cytometry in the SH-SY5Y cell line exposed to paraquat and C2-ceramide. We found that Zanthoxylum rhoifolium Lam, Zanthoxylum martinicense, Nectandra membranacea, and Nectandra reticulata extracts have antioxidant activity higher than quercetin under a β-carotene bleaching assay and protect SH-SY5Y cells against paraquat and C2-ceramide associated with a reduction in ROS. In conclusion, these extracts have a strong neuroprotective potential, and the precise mechanism requires more evaluation.

Sitophilus zeamais es una plaga cosmopolita, que causa pérdidas superiores al 20% en granos almacenados, principalmente en maíz.

Digestive enzymes are currently considered important therapeutic targets for the treatment of obesity and some associated metabolic diseases, such as type 2 diabetes. Piper cumanense is a species characterized by the presence of bioactive constituents, particularly prenylated benzoic acid derivatives. In this study, the inhibitory potential of chemical constituents from P. cumanense and some synthesized compounds was determined on digestive enzymes (pancreatic lipase (PL) and α-glucosidase (AG)). The methodology included isolating and identifying secondary metabolites from P. cumanense, synthesizing some analogs, and a molecular docking study. The chemical study allowed the isolation of four prenylated benzoic acid derivatives (1–4). Four analogs (5–8) were synthesized. Seven compounds were found to significantly inhibit the catalytic activity of PL with IC50 values between 28.32 and 55.8 µM. On the other hand, only two compounds (6 and 7) were active as inhibitors of AG with IC50 values lower than 155 µM, standing out as the potential multitarget of these chromane compounds. Enzyme kinetics and molecular docking studies showed that the bioactive compounds mainly interact with amino acids other than those of the catalytic site in both PL and AG. This work constitutes the first report on the antidiabetic and antiobesity potential of substances derived from P. cumanense.

Digestive enzymes such α-amylase (AA), α-glucosidase (AG) and pancreatic lipase (PL), play an important role in the metabolism of carbohydrates and lipids, being attractive therapeutic targets for the treatment of type 2 diabetes and obesity. Garcinia mangostana is an interesting species because there have been identified xanthones with the potential to inhibit these enzymes. In this study, the multitarget inhibitory potential of xanthones from G. mangostana against AA, AG and PL was assessed. The methodology included the isolation and identification of bioactive xanthones, the synthesis of some derivatives and a molecular docking study. The chemical study allowed the isolation of five xanthones (1–5). Six derivatives (6–11) were synthesized from the major compound, highlighting the proposal of a new solvent-free methodology with microwave irradiation for obtaining aromatic compounds with tetrahydropyran cycle. Compounds with multitarget activity correspond to 2, 4, 5, 6 and 9, highlighting 6 with IC50 values of 33.3 µM on AA, 69.2 µM on AG and 164.4 µM on PL. Enzymatic kinetics and molecular docking studies showed that the bioactive xanthones are mainly competitive inhibitors on AA, mixed inhibitors on AG and non-competitive inhibitors on PL. The molecular coupling study established that the presence of methoxy, hydroxyl and carbonyl groups are important in the activity and interaction of polyfunctional xanthones, highlighting their importance depending on the mode of inhibition.

Los metabolitos secundarios de plantas representan una amplia variedad de compuestos con aplicaciones en industrias como la alimenticia, farmacéutica y agrícola. Sin embargo, aunque las investigaciones en este campo han incrementado en los últimos años, se ha visto limitado el desarrollo de estudios más específicos debido a bajos rendimientos de extracción de estos metabolitos...

Las enzimas digestivas lipasa pancreática y α-glucosidasa, son importantes en el metabolismo de lípidos y carbohidratos, convirtiéndose en blancos terapéuticos atractivos para el tratamiento de la obesidad y patologías asociadas.

Complex diseases such as neurodegenerative disorders and cancer constitute a growing public health problem due to the rising incidence and lack in effective therapies. Since pharmacotherapy based on a single target has been insufficient for drug development in complex diseases, the emerging multi-target approach is a promising strategy for the search of new drug candidates. Plant-derived isoquinoline alkaloids comprise a vast source of multimodal agents with unique structural diversity, and variated range of pharmacological activities. This review offers an exhaustive compilation of the pharmacological relevance and multi-target potential of natural isoquinolines, emphasizing their features and promising activity in complex diseases such as Alzheimer, Parkinson, and Cancer. Selected examples were discussed in depth to illustrate the most relevant structural motifs and their possible relationship with the multimodal activity offering a comprehensive baseline in the search and optimization of isoquinoline scaffolds with polypharmacological potential for complex diseases.

Se analizó el aceite esencial de frutos de P. hispidum Kunth obtenido por el método de hidrodestilación con un rendimiento del 0,8%. Empleando cromatografía de gases espectrometría de masas se identificaron y cuantificaron cerca de 70 compuestos que representan aproximadamente el 99% del aceite obtenido. De acuerdo con la composición relativa, el 49,7% corresponde a monoterpenos, el 37,5% a monoterpenoides, el 3,7% a compuestos aromáticos y un 9,1% a sesquiterpenos. Como compuestos mayoritarios se identificaron limoneno (16,3%), β-pineno (14,5%), α-pineno (13,5%), linalool (9,6%), α-terpineol (8,5%), 1,8-cineol (5,1%), alcanfor (4,4%), camfeno (4,2%), endoborneol (4,0%), trans-pulegol (2,2%), p-cimeno (2,2%), dibencilo (1,2%) y óxido de cariofileno (1,1%). Los demás componentes identificados se encuentran en una concentración relativa menor al 1%.

Two undescribed 4'-O-methylkaempferol-[3″,4″-di-p-coumaroyl]-α-l-rhamnopyranosides, caerulines A and B (1-2), along with three known 4'-O-methylkaempferol diacylrhamnosides isomers (3-5) were isolated from an ethanol extract of the leaves of Persea caerulea, a native plant growing on the Colombian Caribbean coast. The chemical structures of 1 and 2 were elucidated by spectroscopic methods. The effect of compounds 1-5 against four pathogenic microorganisms [i.e., methicillin-resistant Staphylococcus aureus (MRSA), Acinetobacter baumannii, Candida albicans, and Aspergillus fumigatus] was tested in vitro. The compounds exhibited no activity against these pathogens except MRSA (MIC 12-48 μg/mL). Caeruline B (2) was found to be the most active compound with a modest anti-MRSA activity (MIC = 12 μg/mL).

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.

Chemical control of the maize weevil (Sitophilus zeamais) has been ineffective and presents serious collateral damage. Among plant-derived insecticides, essential oils (EOs) are suitable candidates to control this stored products pest. In this work, the insecticidal activities of 45 natural EOs against S. zeamais adults were screened, and the most promising ones (24 EOs) were characterized by GC–MS. The repellent and toxic effects (contact and fumigant) of these 24 EOs were determined, and by a cluster analysis they were classified into two groups considering its fumigant activity and contact toxicity. For the EOs with the highest fumigant potential (14 oils) and their main active constituents (17 compounds), lethal concentrations were determined. The most active EOs were those obtained from L. stoechas and L. alba, with LC50 values of 303.4 and 254.1 µL/L air and characterized by a high content of monoterpenes. Regarding the major compounds, the oxygenated monoterpenes R-(+)-pulegone (LC50 = 0.580 mg/L air), S-(-)-pulegone (LC50 = 0.971 mg/L air) and R-(-)-carvone (LC50 = 1.423 mg/L air) were the most active, as few variations in their concentrations significantly increased insect mortality.

Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) is an insect popularly known as the red flour beetle, it is widely distributed worldwide and can cause serious damage to stored grains. Chemical control is the most used method for managing this pest, however, some substances are toxic to mammals and the environment. Therefore, the development of new effective and safe insecticides is necessary. Essential oils (EOs) can be considered as a potential alternative in the development of pesticides due to their physicochemical properties and varied effects against insects. In the current study, was determined the fumigant toxicity and biochemical effects of selected essential oils against T. castaneum. The 23 selected EOs were characterized by GC-MS and their fumigant lethal concentrations were determined. An exploratory Cluster analysis was performed to find a relationship between fumigant toxicity and chemical composition. Finally, the inhibition of the catalytic activity of acetylcholinesterase (AChE), glutathione S-transferase (GST) and catalase (CAT) was evaluated using protein homogenates obtained from T. castaneum. The results indicated that EOs with the highest fumigant potential were those with greater diversity in their composition, while the least active EOs presented mainly monoterpenes. The most active EOs were those obtained from Foeniculum vulgare and Zanthoxylum monophyllum with LC50 values of 16.23 and 18.54 mu L/L air respectively. Regarding the inhibition of the enzymatic activity of the 23 EOs evaluated at 500 mu L/L, only two caused an inhibition greater that 50% on AChE, which corresponded to EOs from Piper nigrum and Rosmarinus officinalis. Likewise, EOs from C. sinensis, Piper aduncum and Zanthoxylum monophyllum were the only ones able to inhibiting GST activity by more than 50%. Respecting CAT inhibition, 7 EOs caused and inhibition greater than 50%, highlighting those from Lavandula angustifolia, C. sempervirens and Eucalyptus sp. These results show that the EOs evaluated in this study seems to be a promising bio-controller of T. castaneum since have high fumigant toxicity and exert different mechanisms of action.

Introducción: Diferentes especies de la familia Myristicaceae han sido utilizadas con fines medicinales, nutricionales e industriales, mostrando así la importancia y potencial de la familia en diversos campos. El uso medicinal ha sido primordial por diferentes comunidades indígenas y ha venido en aumento como alternativa al tratamiento de enfermedades, por lo cual la investigación se está concentrando en la medicina herbaria y plantas medicinales, siendo este el primer paso para el desarrollo e innovación de fármacos. Entre los tipos de fármacos se destacan los inhibidores enzimáticos, que actúan regulando procesos metabólicos o atacando patógenos. Objetivos: Recopilar información de la herboristería de la familia Myristicaceae que incluya aspectos de fitoquímica, etnobotánica, usos industriales, actividad biológica y determinar posibles metabolitos secundarios que producen inhibición enzimática y actividad biológica. Metodología: La búsqueda de información se realizó con artículos científicos, libros especializados y tesis de grado. Resultados y conclusiones: Se encontró que compuestos fenólicos de tipo: acilfenol, lignano, neolignano, flavonoide, alquenilfenol, tocotrienol y ácido fenólico producen inhibición enzimática. Los compuestos fenólicos identificados en especies de la familia Myristicaceae son una fuente promisoria de metabolitos que producen inhibición enzimática. Siendo los metabolitos de tipo lignanos los que presentaron mayor número de estudios de inhibición enzimática. La información analizada puede servir de base para el desarrollo de investigaciones de relación estructura actividad y/o acoplamiento molecular entre metabolitos secundarios y enzimas inhibidas, con especies de la familia Myristicaceae.

We report on the regio- and stereoselective synthesis of tetrahydrofurans by reaction between epoxides and alkenes in the presence of a Lewis acid. This is an unprecedented formal [3+2] cycloaddition reaction between an epoxide and an alkene. The chemical reaction represents a very concise synthesis of tetrahydrofurans from accessible starting compounds.

Elicitation of cell suspensions culture is a strategy that could increase the production of secondary metabolites under controlled conditions. This research evaluated the effect of methyl jasmonate-MeJA and salicylic acid-SA as elicitors on the production of metabolites in cell suspensions of P. cumanense. The type of elicitor (MeJA or SA), the concentration of elicitor (10 μM and 100 μM), and time of exposition (3, 12, 24 h) on cell suspension were evaluated. Metabolic profiles of intracellular and extracellular extracts were analyzed by UHPLC-DAD and GC–MS. Differential production of metabolites was dependent on the type of elicitor, its concentration, and the time of exposition. Treatments with 100 μM SA were conducted to high production of 5-hydroxymethylfurfural (6.3 %), phenol (6.5 %), and (Z)-9-octadecenamide (8.8 %). This is the first report of elicitation on cell suspensions in the Piper genus and contributes to understanding the effect of MeJA and SA on metabolite production in plant cell culture.

Multifactorial neurodegenerative disorders such as Alzheimer's disease (AD) are considered a growing public health problem due the rising incidence and low effectiveness of current treatments [6]. Since pharmacotherapy based on a single target has been insufficient for drug development in complex diseases, the emerging multi-target approach is a promising strategy for the search of new anti-AD drug candidates. Herein described natural isoquinoline alkaloids were investigated for multi-target activity on key mechanisms associated with the AD's pathogenesis, i.e. cholinergic depletion, beta amyloid (A beta) aggregation and oxidative stress. Alkaloid isolation from root extract of Zanthoxylum rigidum was carried out using multi-step chromatography and TLC-bioautography against acetylcholinesterase (AChE) giving eight purified isoquinoline alkaloids. Isolated compounds were tested for inhibitory activity against cholinesterase (AChE and BChE), monoamine oxidase (MAO-A and B) and A beta aggregation. Our study revealed two benzophenanthridine alkaloids, nitidine (5) and avicine (7), as the most potent multi-target candidates. Both showed dual cholinesterase inhibition, being more active against AChE over BChE, with IC50 values in sub-micromolar range in AChE. Kinetic analysis with cholinesterase showed, that both compounds are reversible-mixed inhibitors, where avicine (7) presented highest potency with K-i values of 0.063 mu M (EeAChE), 0.511 mu M (HrAChE) and 0.123 mu M (EqBChE). In addition, these alkaloids presented moderate A beta(1-42) anti-aggregation activity and MAO-A inhibition with IC(50 )values between 0.5 and 2 mu M. Our findings suggest that avicine (7) is a promising natural compound and multifunctional candidate representing a suitable starting point for the development of new therapeutic agents for Alzheimer's disease.

The Piperaceae family is recognized for its diverse biological properties such as antifungal, antibacterial, cytotoxic and insecticidal activities. Phytochemical investigation of inflorescences from P. cumanense led to the isolation and identification of a new 4-chromanone called oxocumanensic acid, along with five known benzoic acid derivatives. The antifungal activity was evaluated against six phytopathogenic fungi by a mycelium growth inhibition test. All compounds were active against the phytopathogenic fungi, showing a greater activity against fungi of Fusarium genus. Finally, phytotoxicity was evaluated in the extract and its chemical constituents, finding that the natural substances are less toxic than the positive control.