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1.
Photochem Photobiol Sci ; 23(5): 987-996, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38662174

RESUMEN

Pycnoporus sanguineus is a fungus of the phylum Basidiomycota that has many applications in traditional medicine, modern pharmaceuticals, and agricultural industries. Light plays an essential role in the metabolism, growth, and development of fungi. This study evaluated the mycelial growth and antioxidant and anti-inflammatory activities in P. sanguineus fermentation broth (PFB) cultured under different wavelengths of LED irradiation or in the dark. Compared to the dark cultures, the dry weight of mycelia in red- and yellow-light cultures decreased by 37 and 35% and the yields of pigments increased by 30.92 ± 2.18 mg and 31.75 ± 3.06 mg, respectively. Compared with the dark culture, the DPPH free radical scavenging ability, ABTS+ free radical scavenging capacity, and reducing power of yellow-light cultures increased significantly, and their total phenolic content peaked at 180.0 ± 8.34 µg/mL. However, the reducing power in blue-light cultures was significantly reduced, though the total phenol content did not vary with that of dark cultures. In LPS- and IFN-γ-stimulated RAW 264.7 cells, nitrite release was significantly reduced in the red and yellow light-irradiated PFB compared with the dark culture. In the dark, yellow-, and green-light cultures, TNF-α production in the inflamed RAW 264.7 cells was inhibited by 62, 46, and 14%, respectively. With red-, blue-, and white-light irradiation, TNF-α production was significantly enhanced. Based on these results, we propose that by adjusting the wavelength of the light source during culture, one can effectively modulate the growth, development, and metabolism of P. sanguineus.


Asunto(s)
Antioxidantes , Luz , Pycnoporus , Ratones , Animales , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/metabolismo , Células RAW 264.7 , Pycnoporus/metabolismo , Factores Inmunológicos/farmacología , Factores Inmunológicos/química , Lipopolisacáridos/farmacología , Lipopolisacáridos/antagonistas & inhibidores , Picratos/antagonistas & inhibidores , Picratos/química , Agentes Inmunomoduladores/farmacología , Agentes Inmunomoduladores/química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Compuestos de Bifenilo/farmacología
2.
Bioorg Med Chem Lett ; 110: 129882, 2024 Sep 15.
Artículo en Inglés | MEDLINE | ID: mdl-38996937

RESUMEN

We present new small-molecular probes targeting the human PD-L1 protein. The molecules were designed by incorporating a newly discovered N-methylmorpholine substituent into a known biphenyl-based structure. Four prototype derivatives of 4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carbonitrile (STD4), comprising a morpholine substituent fused with a biphenyl core at different orientations were first verified for their potential binding to PD-L1 using the molecular docking method. A more favorable 7-phenyl derivative of STD4 was then equipped with an amide bond, pyridine, and either a tris(hydroxymethyl)aminomethane or serinol tail leading to two final molecules. Among them, compound 1c showed activity in three bioassays, i.e., the homogenous time-resolved fluorescence (HTRF) assay, immune checkpoint blockade (ICB) assay, and T-cell activation (TCA) assay. Our work shows that morpholine can substitute for dioxane and becomes a promising component in PD-L1-targeting molecules. This finding unlocks new avenues for optimizing PD-L1-targeting compounds, presenting exciting prospects for future developments in this field.


Asunto(s)
Antígeno B7-H1 , Compuestos de Bifenilo , Morfolinas , Receptor de Muerte Celular Programada 1 , Humanos , Compuestos de Bifenilo/química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/farmacología , Antígeno B7-H1/antagonistas & inhibidores , Antígeno B7-H1/metabolismo , Relación Estructura-Actividad , Morfolinas/química , Morfolinas/farmacología , Morfolinas/síntesis química , Estructura Molecular , Receptor de Muerte Celular Programada 1/antagonistas & inhibidores , Receptor de Muerte Celular Programada 1/metabolismo , Simulación del Acoplamiento Molecular , Relación Dosis-Respuesta a Droga
3.
Bioorg Med Chem ; 107: 117762, 2024 Jun 01.
Artículo en Inglés | MEDLINE | ID: mdl-38759254

RESUMEN

Honokiol, derived from Magnolia officinalis (a traditional Chinese medicine), has been reported to have anticancer activity. Here, a series of novel honokiol thioethers bearing a 1,3,4-oxadiazole moiety were prepared and evaluated for their anticancer activities against three types of digestive system tumor cells. Biological evaluation showed that honokiol derivative 3k exhibited the best antiproliferative activity against HCT116 cells with an IC50 value of 6.1 µmol/L, superior to the reference drug 5-fluorouracil (IC50: 9.63 ± 0.27 µmol/L). The structure-activity relationships (SARs) indicated that the introduction of -(4-NO2)Ph, 3-pyridyl, -(2-F)Ph, -(4-F)Ph, -(3-F)Ph, -(4-Cl)Ph, and -(3-Cl)Ph groups was favorable for enhancing the anticancer activity of the title honokiol thioethers. Further study revealed that honokiol thioether 3k can well inhibit the proliferation of colon cancer cells HCT116, arresting the cells in G1 phase and inducing cell death. Moreover, a preliminary mechanism study indicated that 3k directly inhibits the transcription and expression of YAP protein without activating the Hippo signaling pathway. Thus, honokiol thioether 3k could be deeply developed for the development of honokiol-based anticancer candidates.


Asunto(s)
Compuestos de Bifenilo , Proliferación Celular , Ensayos de Selección de Medicamentos Antitumorales , Lignanos , Proteínas Señalizadoras YAP , Humanos , Lignanos/farmacología , Lignanos/química , Lignanos/síntesis química , Compuestos de Bifenilo/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Relación Estructura-Actividad , Proliferación Celular/efectos de los fármacos , Células HCT116 , Proteínas Señalizadoras YAP/metabolismo , Estructura Molecular , Neoplasias del Colon/tratamiento farmacológico , Neoplasias del Colon/patología , Neoplasias del Colon/metabolismo , Sulfuros/química , Sulfuros/farmacología , Sulfuros/síntesis química , Factores de Transcripción/metabolismo , Factores de Transcripción/antagonistas & inhibidores , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/síntesis química , Relación Dosis-Respuesta a Droga , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Compuestos Alílicos , Fenoles
4.
Bioorg Chem ; 151: 107629, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39003942

RESUMEN

Melanin is a complex brown pigment, primarily responsible for the skin pigmentation. Therefore, cosmetic industries have always been in search of potent oxidative enzymes useful for melanin degradation, and to promise a fair complexion after using their products. In the present study, lignin peroxidase from Pseudomonas fluorescence LiP-RL5 isolate has been immobilized on super-paramagnetic nanoparticles to enhance its stability and reusability. The chitosan coated enzyme-nanomaterial complex (LiP@MFO-Chit) showed higher melanin decolorization (47.30 ± 2.3 %) compared to the graphene oxide coated nanoparticles (LiP@MFO-GO) (41.60 ± 1.6 %). Synthesized enzyme nanoparticle complexes showed microbicidal effect on skin infection causing pathogen, Pantoea agglomerans with an inhibitory zone of 6.0 ± 0.9 mm and 250 µg/100 µl minimum inhibitory concentration, and a 7.0 ± 1.5 mm zone and 170 µg/100 µl MIC for LiP@MFO-GO and LiP@MFO-Chit, respectively. Antioxidant potential of LiP@MFO-Chit and LiP@MFO-GO nano-conjugates showed a substantial DPPH scavenging activity of 75.7 % and 88.3 %, respectively. Therefore, LiP-nanoparticle hybrid complexes analyzed in this study are not only effective as skin whitening agents but they are potential molecules against various microbial skin infections as well as useful for different other biomedical applications like biorefinery, drug delivery, and dermatology, etc.


Asunto(s)
Quitosano , Grafito , Melaninas , Pruebas de Sensibilidad Microbiana , Melaninas/metabolismo , Melaninas/química , Quitosano/química , Quitosano/farmacología , Grafito/química , Grafito/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Peroxidasas/metabolismo , Peroxidasas/química , Enzimas Inmovilizadas/química , Enzimas Inmovilizadas/metabolismo , Pantoea , Antioxidantes/química , Antioxidantes/farmacología , Antioxidantes/síntesis química , Estructura Molecular , Pseudomonas , Relación Dosis-Respuesta a Droga , Relación Estructura-Actividad , Picratos/antagonistas & inhibidores , Nanopartículas/química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química
5.
Bioorg Chem ; 147: 107340, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38593532

RESUMEN

In pursuit of enhancing the anti-resistance efficacy and solubility of our previously identified NNRTI 1, a series of biphenyl-quinazoline derivatives were synthesized employing a structure-based drug design strategy. Noteworthy advancements in anti-resistance efficacy were discerned among some of these analogs, prominently exemplified by compound 7ag, which exhibited a remarkable 1.37 to 602.41-fold increase in potency against mutant strains (Y181C, L100I, Y188L, F227L + V106A, and K103N + Y181C) in comparison to compound 1. Compound 7ag also demonstrated comparable anti-HIV activity against both WT HIV and K103N, albeit with a marginal reduction in activity against E138K. Of significance, this analog showed augmented selectivity index (SI > 5368) relative to compound 1 (SI > 37764), Nevirapine (SI > 158), Efavirenz (SI > 269), and Etravirine (SI > 1519). Moreover, it displayed a significant enhancement in water solubility, surpassing that of compound 1, Etravirine, and Rilpivirine. To elucidate the underlying molecular mechanisms, molecular docking studies were undertaken to probe the critical interactions between 7ag and both WT and mutant strains of HIV-1 RT. These findings furnish invaluable insights driving further advancements in the development of DAPYs for HIV therapy.


Asunto(s)
Fármacos Anti-VIH , Compuestos de Bifenilo , Diseño de Fármacos , Transcriptasa Inversa del VIH , VIH-1 , Quinazolinas , Inhibidores de la Transcriptasa Inversa , Solubilidad , Humanos , Fármacos Anti-VIH/farmacología , Fármacos Anti-VIH/química , Fármacos Anti-VIH/síntesis química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/farmacología , Compuestos de Bifenilo/química , Relación Dosis-Respuesta a Droga , Farmacorresistencia Viral/efectos de los fármacos , Transcriptasa Inversa del VIH/antagonistas & inhibidores , Transcriptasa Inversa del VIH/metabolismo , VIH-1/efectos de los fármacos , VIH-1/enzimología , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Estructura Molecular , Quinazolinas/farmacología , Quinazolinas/química , Quinazolinas/síntesis química , Inhibidores de la Transcriptasa Inversa/farmacología , Inhibidores de la Transcriptasa Inversa/química , Inhibidores de la Transcriptasa Inversa/síntesis química , Relación Estructura-Actividad
6.
Bioorg Chem ; 150: 107601, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-38991489

RESUMEN

A set of novels 2-thiohydantoin derivatives were synthesized and enaminone function was discussed at position 5 using DMFDMA catalyst which result in formation of pyrazole, isoxazole, benzoxazepine by using reagents such as hydrazine, hydroxylamine and 2-aminothiophenol. These newly synthesized compounds were evaluated for their antioxidant and antiproliferative activity. In vitro studies on the effect of 2-thiohydantoin on scavenging 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) confirmed the free radical scavenging and antioxidant activity of 2-thiohydantoin. The synthesized compounds show significant antioxidant activity. The in vitro antitumor activity of 2-thiohydantoin on MCF7 (breast) and PC3 cells (prostate) was evaluated using MTT assay. Some of the synthesized compounds show significant to moderate antiproliferative properties compared to reference drug erlotinib. Among all, compound 4a exhibit potent antitumor properties against MCF7 and PC3 cancer cell lines with IC50 = 2.53 ± 0.09 /ml & with IC50 = 3.25 ± 0.12 µg/ml respectively and has potent antioxidant activity with IC50 = 10.04 ± 0.49 µg/ml.


Asunto(s)
Antineoplásicos , Antioxidantes , Aromatasa , Proliferación Celular , Ensayos de Selección de Medicamentos Antitumorales , Receptores ErbB , Simulación del Acoplamiento Molecular , Tiohidantoínas , Humanos , Antineoplásicos/farmacología , Antineoplásicos/síntesis química , Antineoplásicos/química , Proliferación Celular/efectos de los fármacos , Antioxidantes/farmacología , Antioxidantes/síntesis química , Antioxidantes/química , Receptores ErbB/antagonistas & inhibidores , Receptores ErbB/metabolismo , Relación Estructura-Actividad , Estructura Molecular , Tiohidantoínas/farmacología , Tiohidantoínas/química , Tiohidantoínas/síntesis química , Aromatasa/metabolismo , Relación Dosis-Respuesta a Droga , Diseño de Fármacos , Inhibidores de Proteínas Quinasas/farmacología , Inhibidores de Proteínas Quinasas/síntesis química , Inhibidores de Proteínas Quinasas/química , Catálisis , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/farmacología , Compuestos de Bifenilo/química , Línea Celular Tumoral , Termodinámica , Picratos/antagonistas & inhibidores , Hidrazinas , Tioamidas
7.
Bioorg Chem ; 148: 107433, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38754311

RESUMEN

Second-generation AR antagonists, such as enzalutamide, are the primary therapeutic agents for advanced prostate cancer. However, the development of both primary and secondary drug resistance leads to treatment failures and patient mortality. Bifunctional agents that simultaneously antagonize and degrade AR block the AR signaling pathway more completely and exhibit excellent antiproliferative activity against wild-type and drug-resistant prostate cancer cells. Here, we reported the discovery and optimization of a series of biphenyl derivatives as androgen receptor antagonists and degraders. These biphenyl derivatives exhibited potent antiproliferative activity against LNCaP and 22Rv1 cells. Our discoveries enrich the diversity of small molecule AR degraders and offer insights for the development of novel AR degraders for the treatment of enzalutamide-resistant prostate cancer.


Asunto(s)
Antagonistas de Receptores Androgénicos , Antineoplásicos , Benzamidas , Compuestos de Bifenilo , Proliferación Celular , Resistencia a Antineoplásicos , Nitrilos , Feniltiohidantoína , Neoplasias de la Próstata , Receptores Androgénicos , Humanos , Masculino , Benzamidas/farmacología , Benzamidas/química , Benzamidas/síntesis química , Nitrilos/química , Nitrilos/farmacología , Feniltiohidantoína/farmacología , Feniltiohidantoína/análogos & derivados , Feniltiohidantoína/química , Compuestos de Bifenilo/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Receptores Androgénicos/metabolismo , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/síntesis química , Proliferación Celular/efectos de los fármacos , Relación Estructura-Actividad , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias de la Próstata/patología , Neoplasias de la Próstata/metabolismo , Resistencia a Antineoplásicos/efectos de los fármacos , Estructura Molecular , Antagonistas de Receptores Androgénicos/farmacología , Antagonistas de Receptores Androgénicos/química , Antagonistas de Receptores Androgénicos/síntesis química , Antagonistas de Receptores Androgénicos/uso terapéutico , Descubrimiento de Drogas , Ensayos de Selección de Medicamentos Antitumorales , Relación Dosis-Respuesta a Droga , Línea Celular Tumoral
8.
J Sep Sci ; 47(9-10): e2300898, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38726747

RESUMEN

Based on the specific binding of drug molecules to cell membrane receptors, a screening and separation method for active compounds of natural products was established by combining phospholipase C (PLC) sensitized hollow fiber microscreening by a solvent seal with high-performance liquid chromatography technology. In the process, the factors affecting the screening were optimized. Under the optimal screening conditions, we screened honokiol (HK), magnolol (MG), negative control drug carbamazepine, and positive control drug amentoflavone, the repeatability of the method was tested. The PLC activity was determined before and after the screening. Experimental results showed that the sensitization factors of PLC of HK and MG were 61.0 and 48.5, respectively, and amentoflavone was 15.0, carbamazepine could not bind to PLC. Moreover, the molecular docking results were consistent with this measurement, indicating that HK and MG could be combined with PLC, and they were potential interacting components with PLC. This method used organic solvent to seal the PLC greatly ensuring the activity, so this method had the advantage of integrating separation, and purification with screening, it not only exhibited good reproducibility and high sensitivity but was also suitable for screening the active components in natural products by various targets in vitro.


Asunto(s)
Productos Biológicos , Fosfolipasas de Tipo C , Productos Biológicos/química , Productos Biológicos/farmacología , Productos Biológicos/aislamiento & purificación , Fosfolipasas de Tipo C/metabolismo , Fosfolipasas de Tipo C/química , Fosfolipasas de Tipo C/antagonistas & inhibidores , Cromatografía Líquida de Alta Presión , Simulación del Acoplamiento Molecular , Lignanos/química , Lignanos/aislamiento & purificación , Lignanos/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Antineoplásicos/química , Antineoplásicos/farmacología , Antineoplásicos/aislamiento & purificación , Humanos , Compuestos Alílicos , Fenoles
9.
Biosci Biotechnol Biochem ; 88(7): 830-838, 2024 Jun 21.
Artículo en Inglés | MEDLINE | ID: mdl-38684478

RESUMEN

Mycosporine-like amino acids (MAAs) are the natural UV-absorbing compounds with antioxidant activity found in microalgae and macroalgae. We collected red algae Asparagopsis taxiformis, Meristotheca japonica, and Polysiphonia senticulosa from Nagasaki, where UV radiation is more intense than in Hokkaido, and investigated the effect of UV radiation on MAA content. It was suggested that A. taxiformis and M. japonica contained shinorine and palythine, while UV-absorbing compound in P. senticulosa could not be identified. The amounts of these MAAs were lower compared to those from Hokkaido. Despite an increase in UV radiation in both regions from February to April, MAA contents of red algae from Nagasaki slightly decreased while those from Hokkaido significantly decreased. This difference was suggested the amount of inorganic nitrogen in the ocean. Antioxidant activity of MAAs increased under alkaline conditions. The extract containing MAAs from P. senticulosa showed the highest antioxidant activity among 4 red algae.


Asunto(s)
Aminoácidos , Antioxidantes , Rhodophyta , Rhodophyta/química , Aminoácidos/análisis , Antioxidantes/química , Antioxidantes/farmacología , Japón , Rayos Ultravioleta , Compuestos de Bifenilo/antagonistas & inhibidores , Concentración de Iones de Hidrógeno , Ciclohexanoles , Ciclohexilaminas , Glicina/análogos & derivados
10.
Luminescence ; 39(8): e4847, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-39192172

RESUMEN

In modern times, nanoparticles have materialized as indispensable things in contemporary medicine, with a variety of uses in clinical, drug and gene conveyance. In the present study, TiO2 nanoparticles (NPs) prepared from the leaf extracts of Mollugooppositifolia and Trianthema portulacastrum were compared with the chemical TiO2-NPs for antibacterial and antioxidant activities and environment-friendly nature through various tools like the UV-visible, X-ray diffraction with the aid of other analytical techniques like HR-TEM, Fourier transform infrared (FT-IR) and photoluminescence spectroscopic techniques. The morphology of green TiO2-NPs is found to be spherical, which is supported by HR-TEM images. FT-IR analyses and X-ray diffraction data ensure that the polycrystalline characters of TiO2-NPs alike to the presence of metal oxide. TiO2-NPs showed a possible photocatalytic activity for the ruin of acid black 1 dye after disclosure to sunlight. The chemical and green methods of TiO2-NPs have acid black 1 dye decomposition rates of 86.66% and 94.33%, respectively. The synthesized TiO2-NPs are also assessed for antimicrobial and antioxidant activities. Green TiO2-NPs exhibit antibacterial activity against Pseudomonas aeruginosa (17 + 0.56 mm) and Staphylococcus aureus (16 + 0.24 mm) at concentrations as low as 100 µL. The green TiO2-NPs showed high inhibition of DPPH I radical (50 µg/m) at 95.17 ± 21. Therefore, TiO2-NPs represent eco-friendly properties that aid in the degradation of dyes due to their antioxidant activity.


Asunto(s)
Antibacterianos , Antioxidantes , Titanio , Antioxidantes/química , Antioxidantes/farmacología , Antioxidantes/síntesis química , Titanio/química , Titanio/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/síntesis química , Nanopartículas/química , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/química , Extractos Vegetales/farmacología , Colorantes/química , Colorantes/farmacología , Luminiscencia , Staphylococcus aureus/efectos de los fármacos , Tamaño de la Partícula , Hojas de la Planta/química , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química
11.
Chem Biodivers ; 21(5): e202400085, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38329156

RESUMEN

A lesser-known bee product called drone brood homogenate (DBH, apilarnil) has recently attracted scientific interest for its chemical and biological properties. It contains pharmacologically active compounds that may have neuroprotective, antioxidant, fertility-enhancing, and antiviral effects. Unlike other bee products, the chemical composition of bee drone larva is poorly studied. This study analyzed the chemical compostion of apilarnil using several methods. These included liquid chromatography-mass spectrometry (LC-MS/MS) and a combination of gas chromatography/mass spectrometry with solid phase micro-extraction (SPME/GC-MS). Additionally, antioxidant activity of the apilarnil was assessed using 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. A chemical assessment of apilarnil showed that it has 6.3±0.00, 74.67±0.10 %, 3.65±0.32 %, 8.80±1.01 %, 13.16±0.94 %, and 8.79±0.49 % of pH, moisture, total lipids, proteins, flavonoids, and carbohydrates, respectively. LC-MS/MS analysis and molecular networking (GNPS) of apilarnil exhibited 44 compounds, including fatty acids, flavonoids, glycerophospholipids, alcohols, sugars, amino acids, and steroids. GC-MS detected 30 volatile compounds in apilarnil, mainly esters (24 %), ketones (23.84 %), ethers (15.05 %), alcohols (11.41 %), fatty acids (10.06), aldehydes (6.73 %), amines (5.46), and alkene (5.53 %). The antioxidant activity of apilarnil was measured using DPPH with an IC50 of 179.93±2.46 µg/ml.


Asunto(s)
Antioxidantes , Compuestos de Bifenilo , Abejas , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Animales , Compuestos de Bifenilo/antagonistas & inhibidores , Cromatografía de Gases y Espectrometría de Masas , Picratos/antagonistas & inhibidores , Espectrometría de Masas en Tándem , Cromatografía Liquida , Microextracción en Fase Sólida
12.
Chem Biodivers ; 21(7): e202301816, 2024 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-38861276

RESUMEN

Phytochemical investigation of the methanol extract from the fruits of Macaranga monandra (Euphorbiaceae Muell. et Arg.) afforded one new geranylated 1',2'-dihydrophenanthrene and two new flavonoid derivatives, named macamondrin (1), macamondrione A (2) and B (3) respectively. The structures of these compounds were elucidated mainly by NMR, mass spectral data and in comparison with data from the literature. Along with compounds 1-3, nine known compounds among which oleanolic acid (4); daucosterol (5); 3ß-acetoxy-11α,12α-epoxytaraxerol (6); 3,3',4-tri-O-methylellagic acid (7); 3,3',4,4'-tetra-O-methylellagic acid (8); 4'-O-methyl-6-isoprenylapigenin (9); 4'-O-methyl-8 isoprenylkaempférol (10); 4'-O-methyl-6-isoprénylkaempférol (11); 6-isoprénylkaempférol (12), were also isolated. Crude extracts as well as isolated compounds were evaluated for their antioxidant activity using the ABTS, DPPH and FRAP methods. It appears that the 50 % radical scavenging concentrations ranging from 6.26 to 11.7 µg/ml on the ABTS radical, from 1.77 to 48.22 µg/ml on the DPPH radical, and from 1.54 to 67.97 µg/ml with the FRAP method. For the compounds tested, very good antioxidant activities were observed, which clearly shows that these molecules can have an anti oxidative stress potentiel.


Asunto(s)
Antioxidantes , Euphorbiaceae , Frutas , Polifenoles , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Frutas/química , Polifenoles/química , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Euphorbiaceae/química , Compuestos de Bifenilo/antagonistas & inhibidores , Picratos/antagonistas & inhibidores , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación
13.
Chem Biodivers ; 21(6): e202400141, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38573801

RESUMEN

Ultrasound extraction (UE) enhanced with deep eutectic solvent (DES) was used to extract Lentinus edodes polysaccharides. Box-Behnken design (BBD) was applied to investigate the influences of water content (10-90 %), solid-liquid solvent (1 : 10-1 : 50 g/mL), time (4-12 min), temperature (40-80 °C) and ultrasonic power (100-500 W) on the yield of Lentinus edodes polysaccharides. The optimal extraction conditions were ultrasonic power of 300 W, extraction time of 8 min, water content of 80 %, a solid-liquid ratio of 1 : 30 g/mL and a temperature of 60 °C, respectively. The highest extraction yield of Lentinus edodes polysaccharide was 10.17 % under optimal conditions. The results of FT-IR, SEM, and monosaccharide composition confirmed that the extracts possessed the characteristics of polysaccharides. In addition, the polysaccharides obtained with the UE enhanced with DES method exhibited higher antioxidant activities than the polysaccharides extracted with the UE method and HWE method. This extraction method can further expand the production efficiency and structural diversity of Lentinus edodes polysaccharides and meet the supply and demand relationship. It can be foreseen that this method can be applied to the extraction of more active substances.


Asunto(s)
Antioxidantes , Polisacáridos , Hongos Shiitake , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Disolventes Eutécticos Profundos/química , Picratos/antagonistas & inhibidores , Polisacáridos/química , Polisacáridos/aislamiento & purificación , Polisacáridos/farmacología , Hongos Shiitake/química , Ondas Ultrasónicas
14.
Chem Biodivers ; 21(6): e202302032, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38308434

RESUMEN

Honokiol (HK) is a traditional Chinese herbal bioactive compound that originates mainly from the Magnolia species, traditionally used to treat anxiety and stroke, as well as alleviation of flu symptoms. This natural product and its derivatives displayed diverse biological activities, including anticancer, antioxidant, anti-inflammatory, neuroprotective, and antimicrobial activities. However, its poor bioavailability and pharmacological activity require primary consideration in the development of HK-based drugs. Recent innovative HK formulations based on the nanotechnology approach allowed for improvement in both bioavailability and therapeutic efficacy. Chemical derivation and drug combination are also effective strategies to ameliorate the drawbacks of HK. In recent years, studies on HK derivatives and compositions have made great progress in the treatment of cancer, inflammation, bacterial infection, cardiovascular, and cerebrovascular diseases, demonstrating better activity than HK. The objective of this review is an examination of the recent developments in the field of pharmacological activity of HK and its drug-related issues, and approaches to improve its physicochemical and biological properties, including solubility, stability, and bioavailability. Recent patents and the ongoing clinical trials in HK are also summarized.


Asunto(s)
Compuestos de Bifenilo , Lignanos , Lignanos/química , Lignanos/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/farmacología , Compuestos de Bifenilo/química , Humanos , Antioxidantes/química , Antioxidantes/farmacología , Animales , Disponibilidad Biológica , Antiinflamatorios/química , Antiinflamatorios/farmacología , Antiinflamatorios/uso terapéutico , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/farmacología , Sistemas de Liberación de Medicamentos , Estructura Molecular , Compuestos Alílicos , Fenoles
15.
Chem Biodivers ; 21(8): e202400591, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38795371

RESUMEN

Assessment of Moroccan Cannabis sativa Seed Oil: Chemical Analysis and Evaluation of Antioxidant, Toxicological, and Antinociceptive Effects. by K. Raoui et al., Cadi Ayyad University, Marrakech, Morocco. Cannabis sativa L., locally known as "El kif", belongs to the Cannabaceae family. This study aims to conduct a chemical analysis of Cannabis sativa seed oil (CSSO) and assess its acute toxicity, antioxidant properties, and analgesic effects. The chemical analysis was performed using gas chromatography and mass spectrometry (GC/MS) to identify fatty acids (FAs) contents. Antioxidant activity was evaluated in vitro using the (2,2-diphenyl-1-picrylhydrazyl) DPPH radical scavenging method and the (ferric reducing antioxidant power) FRAP method. Concurrently, acute toxicity, along with antinociceptive activity, was studied through three distinct animal models: writhing test, formalin test, and hot plate test. The results revealed that linoleic acid, oleic acid, α-linolenic acid, and palmitic acid were the main components of CSSO. The LD50 of CSSO was greater than 5 g/kg, indicating low toxicity. Additionally, CSSO exhibited a significant content of flavonoids and total polyphenols, along with notable antioxidant activity with important values. The results indicated a significant increase in thermal stimulus latency, a reduction in the number of writhes induced by acetic acid, and a decrease in licking time in both phases of the formalin test. In conclusion, this study suggests promising results for CSSO, emphasizing its potential as a therapeutic agent.


Asunto(s)
Analgésicos , Antioxidantes , Cannabis , Aceites de Plantas , Semillas , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Analgésicos/farmacología , Analgésicos/química , Analgésicos/aislamiento & purificación , Aceites de Plantas/química , Aceites de Plantas/farmacología , Aceites de Plantas/aislamiento & purificación , Cannabis/química , Animales , Ratones , Marruecos , Semillas/química , Masculino , Cromatografía de Gases y Espectrometría de Masas , Compuestos de Bifenilo/antagonistas & inhibidores , Picratos/antagonistas & inhibidores , Femenino
16.
Chem Biodivers ; 21(6): e202400379, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38743034

RESUMEN

Robusta coffee blossom honey stands as a key regional product in Dak Lak province, Vietnam. Despite its significance, there exists a dearth of scientific data for assessing its quality. This study aims to fill this gap by characterizing the physicochemical properties and biological activities of coffee blossom honeys from three distinct sub-regions within Dak Lak province, Vietnam. These activities include ferric reducing power (FRP), DPPH and ABTS radical scavenging, as well as tyrosinase inhibitory activities. Moreover, the study compares these honey samples with other popular varieties in Vietnam, such as Lychee and Longan honeys. The physicochemical parameters of the honey samples meet the standards set by Codex Alimentarius 2001. Through UPLC analysis, eleven compounds were identified, with caffeine serving as a marker for coffee honey. Furthermore, by employing multiple factor analysis (MFA), it was observed that certain physicochemical properties correlate positively with tyrosinase inhibitory, DPPH, ABTS free radicals scavenging activities, and FRP. Notably, tyrosinase inhibitory activity exhibited a positive correlation with antioxidant activity. These findings underscore the high quality of Coffea robusta honey, showcasing its potent antioxidant and tyrosinase inhibitory activities.


Asunto(s)
Antioxidantes , Inhibidores Enzimáticos , Miel , Monofenol Monooxigenasa , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Benzotiazoles/antagonistas & inhibidores , Benzotiazoles/química , Compuestos de Bifenilo/antagonistas & inhibidores , Café/química , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Flores/química , Miel/análisis , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Picratos/antagonistas & inhibidores , Ácidos Sulfónicos/antagonistas & inhibidores , Vietnam
17.
Chem Biodivers ; 21(5): e202301330, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38220973

RESUMEN

It is obvious that the oxidation process is an undeniable fact and when it comes to aging, one of the first solutions that come to mind is natural products. When it comes to natural products, both plants and bee products play an important, almost combative role against oxidation. For this purpose, natural products of both plant and animal origin were considered together in our study: Linden, green tea, aronia, wild grapes, myrtle, blueberries and basil, honey, pollen and propolis. Total phenolic content values of the extracts ranged between 49.28 and 3859.06 mg gallic acid equivalent/100 g, and propolis, green tea, chestnut flower and aronia samples were found to have the highest values. When looking at the NOS inhibition potential, it was determined that propolis, pollen and aronia samples had the highest percentage inhibition values of 98.11, 92.29, 83.44, respectively. Antioxidant activities of methanolic extracts were investigated using iron(III) reducing/antioxidant capacity (FRAP), 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity test and NOS inhibition tests. The phenolic composition of methanolic extracts was tested using the RP-HPLC-UV (high-performance liquid chromatographic method with ultraviolet) method with 19 phenolic standards.


Asunto(s)
Antioxidantes , Productos Biológicos , Óxido Nítrico Sintasa , Fenoles , Antioxidantes/farmacología , Antioxidantes/química , Fenoles/química , Fenoles/farmacología , Productos Biológicos/química , Productos Biológicos/farmacología , Animales , Óxido Nítrico Sintasa/antagonistas & inhibidores , Óxido Nítrico Sintasa/metabolismo , Abejas , Inhibidores Enzimáticos/farmacología , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Picratos/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Cromatografía Líquida de Alta Presión
18.
Chem Biodivers ; 21(5): e202400272, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38489001

RESUMEN

Within a study focused on Sinapis pubescens subsp. pubescens wild from Sicily (Italy), an edible species still unexplored, our earlier published work has demonstrated good in vitro antioxidant properties for the flower and leaf hydroalcoholic extracts, exhibiting quite different qualitative-quantitative phenolic profiles. Herein, further research was designed to elucidate the role played by phenolic compounds in the different antioxidant mechanisms highlighted for the extracts. To achieve this goal, the crude extracts were subjected to liquid-liquid partitioning with solvents of increasing polarity; then, the fractions were investigated for their antioxidant properties using different in vitro assays. For both flowers and leaves, the ethyl acetate fractions exhibited the best activity in DPPH and reducing power assays, followed by n-butanol. The total phenolic content determination indicated these fractions as the phenolic-rich ones, which were characterized by HPLC-PDA/ESI-MS analysis. Conversely, the phenolic-rich fractions did not show any chelating activity, which was highlighted for the more hydrophobic ones.


Asunto(s)
Antioxidantes , Compuestos de Bifenilo , Flores , Fenoles , Extractos Vegetales , Hojas de la Planta , Hojas de la Planta/química , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/farmacología , Flores/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Compuestos de Bifenilo/antagonistas & inhibidores , Brassicaceae/química , Picratos/antagonistas & inhibidores , Cromatografía Líquida de Alta Presión
19.
Chem Biodivers ; 21(5): e202301880, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38494456

RESUMEN

This paper reports on some physicochemical and phytochemical characteristics (i. e. pH, electrical conductivity, colour, moisture content, total phenolic content, sugar profile) and in vitro antioxidant activity of honeys harvested from five legume species, red clover (Trifolium pratense), balansa clover (T. michelianum), Persian clover (T. resupinatum), purple clover (T. purpureum) and sanfoin, also known as holy clover (Onobrychis viciifolia), that were grown in enclosed shade houses to ensure that the honeys' characteristics are reflective of a truly monofloral honey. Glucose and fructose, determined via High-Performance Thin-Layer Chromatography (HPTLC) analysis, were found as the main sugars in all investigated honeys with the ratio of fructose to glucose ranging from 1 : 1.2 to 1 : 1.6. The honeys' pH values ranged from 3.9 to 4.6 which met Codes Alimentarius (CA) requirements. The moisture content was found to be between 17.6 and 22.2 % which in some cases was slightly higher than CA requirements (≤20 %). The honeys' colour values, prior and after filtration, were between 825.5-1149.5 mAU and 532.4-824.8 mAU respectively, illustrating golden yellow to deep yellow hues. The total phenolic content (TPC) of the honeys was determined using a modified Folin-Ciocalteu assay. Their antioxidant activity was captured by the Ferric Reducing-Antioxidant Power (FRAP) assay as well as HPTLC analysis coupled with 2,2-diphenyl-1-picrylhydrazyl (DPPH) derivatisation. The highest total phenolic content was found in red clover honey (45.4 mg GAE/100 g) whereas purple clover honey showed the highest level of activity in the FRAP assay (7.3 mmol Fe2+/kg). HPTLC-DPPH analysis of the honeys' organic extracts demonstrated the presence of various bioactive compounds that contribute to their overall antioxidant activity. This study developed a methodology for producing monofloral clover honeys in a space limited, enclosed production system, which allowed to collate important baseline data for these honeys that can serve as the foundation for their potential future development into commercial honeys, including honeys that can be used for medicinal purposes.


Asunto(s)
Antioxidantes , Miel , Fitoquímicos , Antioxidantes/química , Antioxidantes/farmacología , Antioxidantes/análisis , Miel/análisis , Fitoquímicos/química , Fitoquímicos/farmacología , Fitoquímicos/análisis , Fitoquímicos/aislamiento & purificación , Fenoles/análisis , Fenoles/química , Concentración de Iones de Hidrógeno , Trifolium/química , Picratos/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Cromatografía en Capa Delgada
20.
Chem Biodivers ; 21(8): e202400596, 2024 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-38804585

RESUMEN

Three polysaccharides, PTC, PTH, and PTB, were extracted from Pinellia ternata using three different extraction conditions: room temperature water, hot water, and 2 % Na2CO3 solution. PTC and PTH were composed of rhamnose, glucose, galactose, mannose, glucuronic acid, galacturonic acid, and arabinose, which combine to form complex structures. PTB was composed solely of glucose and rhamnose. Further analysis indicated that PTC and PTB exhibited triple-helix structures. PTC showed the highest scavenging capacity against DPPH, superoxide anion, and hydroxyl radicals, with half maximal inhibitory concentrations (IC50) of 1004.1, 1584.1, and 1584.1 µg/mL, respectively. Additionally, PTC, PTH, and PTB were subjected to sulfation, phosphorylation, and selenization, resulting in the production of nine derivates. The distinctive absorptive bands of these derivates were determined through infrared spectroscopy. Selenized and sulfated derivates have shown significant antitumor and immunoenhancing properties. Our findings revealed that at 400 µg/mL, the inhibition rate of selenated PTB on HeLa cells was 54.2 % and that on HepG2 cells was 43.1 %. Additionally, selenized PTC displayed significant immunoenhancing activity, with a proliferation rate of 63.7 % at 400 µg/mL in RAW264.7 cells. These results provide valuable evidence supporting the consideration of polysaccharides from Pinellia ternata as a potential candidate for the development of antineoplastic drugs.


Asunto(s)
Pinellia , Polisacáridos , Polisacáridos/química , Polisacáridos/farmacología , Polisacáridos/aislamiento & purificación , Humanos , Pinellia/química , Células Hep G2 , Células HeLa , Proliferación Celular/efectos de los fármacos , Ratones , Animales , Supervivencia Celular/efectos de los fármacos , Picratos/antagonistas & inhibidores , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Ensayos de Selección de Medicamentos Antitumorales , Compuestos de Bifenilo/antagonistas & inhibidores , Relación Dosis-Respuesta a Droga , Relación Estructura-Actividad , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación
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