Steroid-Related Metabolites from Edible Mushroom Laetiporus sulphureus

Eighteen steroid-related compounds were found to be chemical constituents for a steroidal fraction obtained from the fruiting body of the edible mushroom Laetiporus sulphureus on the basis of GC-MS analyses. Compounds were found to be mostly associated to the ergostane and lanostane moieties. Lanost-8,25-dien- 3β-ol 3 (8.8%), lanost-7,9(11),24-trien-3β,15α-diol (polycarpol) 11 (12.7%), 15-norlanost-9(11)-en-3β,14,15-triol 13 (15.3%), and 3β,15α-dihydroxy-24-methylenelanost-8-en-21-oic acid (sulphurenic acid) 18 (15.4%), were found to be the main compounds

Quinoline alkaloids and friedelane-type triterpenes isolated from leaves and wood of Esenbeckia alata kunt (Rutaceae)

This work describes the phytochemical exploration of the ethanol extract from leaves and wood of Esenbeckia alata, leading to the isolation and identification of quinoline alkaloids 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one, N-methylflindersine, dictamine, kokusaginine, Γ-fagarine, flindersiamine, as well as the fridelane-type triterpenes, frideline, fridelanol and its acetate derivative. Identification of these compounds was based on full analyses of spectroscopic data (¹H, 13C, 1D, 2D, IR, MS) and comparison with data reported in literature. Compound 4-methoxy-3-(3'-methyl-but-2'-enyl)-N-methyl-quinolin-2(1 H)-one is reported for the first time for the genus Esenbeckia

Metabolitos con actividad biológica aislados de especies pertenecientes a la familia lauraceae

La familia Lauraceae posee una variedad apreciable de especies, de las cuales en su mayoría son utilizadas en la medicina tradicional. El objetivo del presente trabajo es dar a conocer los resultados que se han obtenido en el Grupo de Investigación en Productos Naturales Vegetales del Departamento de Química de la Universidad Nacional de Colombia Sede Bogotá, en estudios fitoquímicos y de actividad biológica hechos a especies de esta familia

Tandem Reactions in Organic Synthesis: The Artistic Approach in Modern Organic Chemistry

The rise of the processes involving sequential reactions (tandem) is mainly due to its advantages. Although it is required high inventiveness and synthetic knowledge, this provides synthetic pathways and processes whose atomic economy is high, in addition to being inexpensive, since it can avoid many purification and separation steps during synthesis. They are also environmentally generous, avoiding the use and production of toxic substances, and the possibility to build complex molecules with high stereoselectivity. This review aims to give a few examples, from existing plethora so far, allowing illustrating and clarifying aspects related to processes involving sequential reactions with an inventiveness that borders on a level that it would be considered as art

Efecto citotóxico de algunos compuestos naturales aislados de plantas Laureaceae y derivados sintéticos

Introduction. The antiproliferative effect of eleven neolignans, two lignans and one diterpene isolated from three Lauraceae plants, four benzofurans and two bicyclooctanes synthetic derivatives was evaluated in vitro on a set of five human cancer cells from solid tumors with a high incidence in Colombia.Objective. To evaluate the cytotoxic effect of twenty compounds on the tumor cell lines HeLa, A-549, Hep-2, PC-3, and MCF-7.Materials and methods. Fourteen natural compounds were isolated by chromatographic techniques from three native colombian plants (Pleurothyrium cinereum, Ocotea macrophylla and Nectandra amazonum), whose structures were established by spectroscopic methods; six synthetic derivatives were prepared by oxyarylation and diazomethane methylation. Antiproliferative effect and cell recovery were performed by means of in vitro treatment of tumor cell lines with test compounds, evaluating cell viability by resazurin staining.Results. Among test compounds, only neolignans ocophyllal A, cinerin D, kaurenoic acid, two benzofuran-derivatives, and synthetic (-)-cinerin A were found to have antiproliferative effect at different levels. Bicyclooctanoids as well as kaurenoic acid exhibited activity against all human cancer cells while benzofuranoids showed selective activity against HeLa. Furthermore, compounds (-)-cinerin A and kaurenoic acid exhibited total lethal effect against all-five cell lines and PC-3, Hep-2, and A549 cell lines, respectively.Conclusion. Test compounds exhibiting antiproliferative activity showed interesting results, which would promote their use as lead compounds on further studies for anticancer agents development.Introducción. El efecto contra la proliferación celular de once neolignanos, dos lignanos y un diterpeno, aislados de tres plantas de la familia Lauraceae, y cuatro benzofuranos y dos biciclooctanos sintéticos, fue evaluado in vitro sobre cinco líneas celulares derivadas de tumores sólidos de alta incidencia en Colombia.Objetivo. Evaluar el efecto citotóxico de veinte compuestos sobre las líneas tumorales HeLa, A-549, Hep-2, PC-3 y MCF-7.Materiales y métodos. Los 14 compuestos de origen natural fueron aislados de tres plantas nativas colombianas (Pleurothyrium cinereum, Ocotea macrophylla y Nectandra amazonum) por técnicas cromatográficas y se establecieron sus estructuras por métodos espectroscópicos, y los seis derivados sintéticos fueron preparados mediante reacción de oxiarilación y metilación con diazometano. El efecto contra la proliferación y la recuperación celular se hicieron mediante tratamiento in vitro de las líneas tumorales con los compuestos , evaluando la viabilidad celular por tinción con resazurina.Resultados. Entre los compuestos evaluados, solamente ocofilal A, cinerina D, ácido kaurenoico, dos benzofuranos y la (-)-cinerina A sintética presentaron actividad contra la proliferación celular en diferentes niveles. Los biciclooctanos, así como el ácido kaurenoico, fueron activos contra todas las líneas celulares, mientras que los benzofuranoides mostraron actividad selectiva contra HeLa. Además, la (-)-cinerina A exhibió un efecto letal total contra todas las líneas celulares, mientras que el ácido kaurenóico presentó efecto letal total contra PC-3, Hep-2 y A549.Conclusión. Los compuestos evaluados que exhibieron actividad contra la proliferación celular mostraron resultados interesantes, lo cual sugiere su potencial uso como cabezas de serie o moléculas plantilla en el desarrollo de agentes anticancerígenos

Steroid-Related Metabolites from Edible Mushroom Laetiporus sulphureus

Eighteen steroid-related compounds were found to be chemical constituents for a steroidal fraction obtained from the fruiting body of the edible mushroom Laetiporus sulphureus on the basis of GC-MS analyses. Compounds were found to be mostly associated to the ergostane and lanostane moieties. Lanost-8,25-dien- 3β-ol 3 (8.8%), lanost-7,9(11),24-trien-3β,15α-diol (polycarpol) 11 (12.7%), 15-norlanost-9(11)-en-3β,14,15-triol 13 (15.3%), and 3β,15α-dihydroxy-24-methylenelanost-8-en-21-oic acid (sulphurenic acid) 18 (15.4%), were found to be the main compounds

Metabolitos con actividad biológica aislados de especies pertenecientes a la familia lauraceae.

The family lauraceae have a great variety of specie, which most are use in the traditional medicine. The main objective from present work is to release the results obtained in the Research Group in Vegetable Natural Products from department of chemistry from Nacional University from Colombia, in phytochemical and biological activity studies carried out to specie from this family.La familia Lauraceae posee una variedad apreciable de especies, de las cuales en su mayoría son utilizadas en la medicina tradicional. El objetivo del presente trabajo es dar a conocer los resultados que se han obtenido en el Grupo de Investigación en Productos Naturales Vegetales del Departamento de Química de la Universidad Nacional de Colombia Sede Bogotá, en estudios fitoquímicos y de actividad biológica hechos a especies de esta familia

Tandem Reactions in Organic Synthesis: The Artistic Approach in Modern Organic Chemistry

The rise of the processes involving sequential reactions (tandem) is mainly due to its advantages. Although it is required high inventiveness and synthetic knowledge, this provides synthetic pathways and processes whose atomic economy is high, in addition to being inexpensive, since it can avoid many purification and separation steps during synthesis. They are also environmentally generous, avoiding the use and production of toxic substances, and the possibility to build complex molecules with high stereoselectivity. This review aims to give a few examples, from existing plethora so far, allowing illustrating and clarifying aspects related to processes involving sequential reactions with an inventiveness that borders on a level that it would be considered as art

Machine learning models to select potential inhibitors of acetylcholinesterase activity from SistematX: a natural products database

Alzheimer's disease is the most common form of dementia, representing 60-70% of dementia cases. The enzyme acetylcholinesterase (AChE) cleaves the ester bonds in acetylcholine and plays an important role in the termination of acetylcholine activity at cholinergic synapses in various regions of the nervous system. The inhibition of acetylcholinesterase is frequently used to treat Alzheimer's disease. In this study, a merged BindingDB and ChEMBL dataset containing molecules with reported half-maximal inhibitory concentration (IC50) values for AChE (7032 molecules) was used to build machine learning classification models for selecting potential AChE inhibitors from the SistematX dataset (8593 secondary metabolites). A total of seven fivefold models with accuracy above 80% after cross-validation were obtained using three types of molecular descriptors (VolSurf, DRAGON 5.0, and bit-based fingerprints). A total of 521 secondary metabolites (6.1%) were classified as active in this stage. Subsequently, virtual screening was performed, and 25 secondary metabolites were identified as potential inhibitors of AChE. Separately, the crystal structure of AChE in complex with (-)-galantamine was used to perform molecular docking calculations with the entire SistematX dataset. Consensus analysis of both methodologies was performed. Only eight structures achieved combined probability values above 0.5. Finally, two sesquiterpene lactones, structures 15 and 24, were predicted to be able to cross the blood-brain barrier, which was confirmed in the VolSurf+ quantitative model, revealing these two structures as the most promising secondary metabolites for AChE inhibition among the 8593 molecules tested. A consensus analysis of classification models and molecular docking calculations identified four potential inhibitors of acetylcholinesterase from the SistematX dataset (8593 structures)Incluye referencias bibliográfica