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1.
Fitoterapia ; 156: 105092, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34826556

RESUMEN

Caged-polyprenylated xanthonoids represent a rare class of natural products. This type of compounds is mainly isolated from Genus Garcinia. Phytochemical studies on the leaves and twigs of Garcinia oligantha led to the isolation of four new caged-polyprenylated xanthonoids, oliganthone CF (1-4), and two new simple xanthones (5-6), oliganthaxanthone D and oliganthaxanthone E. Eight known other polyprenylated xanthones (7-14) including five caged-polyprenylated xanthonoids (7-11) were also isolated. Their structures were elucidated based on the analyses of extensive spectroscopic data. All the isolated compounds except for 5, 6 and 14 showed cell viability reducing effect against human lung cancer A549 cells. Compounds 1-3 were proved to be potential apoptosis inducing agents.


Asunto(s)
Citotoxinas/toxicidad , Garcinia/química , Extractos Vegetales/toxicidad , Xantonas/toxicidad , Células A549 , Apoptosis , Western Blotting , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Humanos , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Tallos de la Planta/química , Espectrofotometría Infrarroja , Espectrofotometría Ultravioleta , Xantonas/química , Xantonas/aislamiento & purificación
2.
Fitoterapia ; 156: 105089, 2022 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-34800595

RESUMEN

Eight previously undescribed compounds, two quinones (1-2), one sesquiterpene (3), and five phenol compounds (4-8), including three enantiomers (6a, 7a, and 8a), along with three corresponding known enantiomers (6b-8b) were isolated from the aerial parts of Morinda umbellata L. Their structures were elucidated by 1D and 2D NMR spectroscopy, X-ray diffraction, and experimental and calculated ECD spectra, respectively. Compound 5 was found to have weak cytotoxity, which inhibited the growth of seven human cancer cell lines (A2780, HeLa, MCF-7, BGC-823, H7420, Ketr3 and SW 1990) with IC50 values from 13.3 to 15.1 µM.


Asunto(s)
Citotoxinas/toxicidad , Morinda/química , Fenoles/toxicidad , Quinonas/toxicidad , Sesquiterpenos/toxicidad , Línea Celular Tumoral , Cromatografía Líquida de Alta Presión , Cristalografía por Rayos X , Citotoxinas/aislamiento & purificación , Humanos , Concentración 50 Inhibidora , Espectroscopía de Resonancia Magnética , Fenoles/aislamiento & purificación , Componentes Aéreos de las Plantas/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Quinonas/aislamiento & purificación , Sesquiterpenos/aislamiento & purificación
3.
Molecules ; 26(24)2021 Dec 20.
Artículo en Inglés | MEDLINE | ID: mdl-34946791

RESUMEN

In the present study, mace-mediated silver nanoparticles (mace-AgNPs) were synthesized, characterized, and evaluated against an array of pathogenic microorganisms. Mace, the arils of Myristica fragrans, are a rich source of several bioactive compounds, including polyphenols and aromatic compounds. During nano synthesis, the bioactive compounds in mace aqueous extracts serve as excellent bio reductants, stabilizers, and capping agents. The UV-VIS spectroscopy of the synthesized NPs showed an intense and broad SPR absorption peak at 456 nm. Dynamic light scattering (DLS) analysis showed the size with a Z average of 50 nm, while transmission electron microscopy (TEM) studies depicted the round shape and small size of the NPs, which ranged between 5-28 nm. The peaks related to important functional groups, such as phenols, alcohols, carbonyl groups, amides, alkanes and alkenes, were obtained on a Fourier-transform infrared spectroscopy (FTIR) spectrum. The peak at 3 keV on the energy dispersive X-ray spectrum (EDX) validated the presence of silver (Ag). Mace-silver nanoparticles exhibited potent antifungal and antibacterial activity against several pathogenic microorganisms. Additionally, the synthesized mace-AgNPs displayed an excellent cytotoxic effect against the human cervical cancer cell line. The mace-AgNPs demonstrated robust antibacterial, antifungal, and cytotoxic activity, indicating that the mace-AgNPs might be used in the agrochemical industry, pharmaceutical industry, and biomedical applications. However, future studies to understand its mode of action are needed.


Asunto(s)
Antibacterianos , Antifúngicos , Nanopartículas del Metal , Myristica/química , Extractos Vegetales/química , Plata , Antibacterianos/síntesis química , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Antifúngicos/farmacología , Bacterias/crecimiento & desarrollo , Citotoxinas/síntesis química , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Hongos/crecimiento & desarrollo , Células HeLa , Humanos , Nanopartículas del Metal/química , Nanopartículas del Metal/uso terapéutico , Plata/química , Plata/farmacología
4.
Molecules ; 26(22)2021 Nov 20.
Artículo en Inglés | MEDLINE | ID: mdl-34834104

RESUMEN

Maesa membranacea A. DC. (Primulaceae) is a plant species that has been frequently used by practitioners of the traditional ethnobotany knowledge from northern and central Vietnam. However, the chemical constituents of the plant remained unknown until recently. Chromatographic separation of a chloroform-soluble fraction of extract from leaves of M. membranacea led to the isolation of two new polyesterified ursane triterpenes (1-2) and two known apocarotenoids: (+)-dehydrovomifoliol (3) and (+)-vomifoliol (4). The chemical structures of the undescribed triterpenoids were elucidated using 1D and 2D MNR and HRESIMS spectral data as 2α,6ß,22α-triacetoxy-11α-(2-methylbutyryloxy)-urs-12-ene-3α,20ß-diol (1) and 2α,6ß,22α-triacetoxy-urs-12-ene-3α,11α,20ß-triol (2). The newly isolated triterpenoids were tested for their cytotoxic activity in vitro against two melanoma cell lines (HTB140 and A375), normal skin keratinocytes (HaCaT), two colon cancer cell lines (HT29 and Caco-2), two prostate cancer cell lines (DU145 and PC3) and normal prostate epithelial cells (PNT-2). Doxorubicin was used as a reference cytostatic drug. The 2α,6ß,22α-triacetoxy-11α-(2-methylbutyryloxy)-urs-12-ene-3α,20ß-diol demonstrated cytotoxic activity against prostate cancer cell lines (Du145-IC50 = 35.8 µg/mL, PC3-IC50 = 41.6 µg/mL), and at a concentration of 100 µg/mL reduced viability of normal prostate epithelium (PNT-2) cells by 41%.


Asunto(s)
Antineoplásicos Fitogénicos , Citotoxinas , Maesa/química , Neoplasias/tratamiento farmacológico , Hojas de la Planta/química , Triterpenos , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Células CACO-2 , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Células HT29 , Humanos , Neoplasias/metabolismo , Neoplasias/patología , Células PC-3 , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología
5.
Molecules ; 26(15)2021 Jul 25.
Artículo en Inglés | MEDLINE | ID: mdl-34361638

RESUMEN

The species Cordia verbenacea DC (Boraginaceae), known as the whaling herb and camaradinha, is a perennial shrub species native to the Atlantic Forest. Its leaves are used in folk medicine as an anti-inflammatory, analgesic, antiulcerogenic and curative agent, in the form of teas or infusions for internal or topical use. The present study aimed to verify the cytotoxicity of the essential oil and the leishmanicidal and trypanocidal potential of C. verbenacea. The essential oil was characterized by GC-MS. The in vitro biological activity was determined by anti-Leishmania and anti-Trypanosoma assays. The cytotoxixity was determined using mammalian fibroblasts. The C. verbenacea species presented α-pinene (45.71%), ß-caryophyllene (18.77%), tricyclo[2,2,1-(2.6)]heptane (12.56%) as their main compounds. The essential oil exhibited strong cytotoxicity at concentrations below 250 µg/mL (LC50 138.1 µg/mL) in mammalian fibroblasts. The potent anti-trypanosome and anti-promastigote activities occurred from the concentration of 62.5 µg/mL and was considered clinically relevant. The results also demonstrate that at low concentrations (<62.5 µg/mL), the essential oil of C. verbenacea managed to be lethal for these activities. This can be considered an indication of the power used in daily human consumption. Therefore, it can be concluded that the essential oil of C. verbenacea contains a compound with remarkable antiparasitic activities and requires further research.


Asunto(s)
Cordia/química , Citotoxinas , Leishmania braziliensis/crecimiento & desarrollo , Aceites Volátiles , Tripanocidas , Trypanosoma cruzi/crecimiento & desarrollo , Animales , Línea Celular , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Ratones , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/farmacología , Tripanocidas/química , Tripanocidas/aislamiento & purificación , Tripanocidas/farmacología
6.
Molecules ; 26(15)2021 Jul 28.
Artículo en Inglés | MEDLINE | ID: mdl-34361724

RESUMEN

Orchids are rich treasure troves of various important phytomolecules. Among the various medicinal orchids, Ansellia africana stands out prominently in the preparing of various herbal medicines due to its high therapeutic importance. The nodal explants of A. africana were sampled from asymbiotically germinated seedlings on basal Murashige and Skoog (MS) medium and were micropropagated in MS medium supplemented with 3% sucrose and 10 µM meta topolin (mT) + 5 µM naphthalene acetic acid (NAA) +15 µM indole butyric acid (IBA) + 30 µM phloroglucinol (PG). In the present study, the essential oil was extracted by hydrodistillation and the oleoresins by the solvent extraction method from the micropropagated A. africana. The essential oil and the oleoresins were analysed by Gas Chromatography (GC) and GC/MS (Mass spectrometry). A total of 84 compounds were identified. The most predominant components among them were linoleic acid (18.42%), l-ascorbyl 2,6-dipalmitate (11.50%), linolenic acid (10.98%) and p-cresol (9.99%) in the essential oil; and eicosane (26.34%), n-butyl acetate (21.13%), heptadecane (16.48%) and 2-pentanone, 4-hydroxy-4-methyl (11.13%) were detected in the acetone extract; heptadecane (9.40%), heneicosane (9.45%), eicosane (6.40%), n-butyl acetate (14.34%) and styrene (22.20%) were identified and quantified in the ethyl acetate extract. The cytotoxic activity of essential oil and oleoresins of micropropagated A. africana was evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Bromide) assay on Vero cells compared to the standard drug doxorubicin chloride. The present research contains primary information about the therapeutic utility of the essential oil and oleoresins of A. africana with a promising future research potential of qualitative and quantitative improvement through synchronised use of biotechnological techniques.


Asunto(s)
Citotoxinas/aislamiento & purificación , Aceites Volátiles/aislamiento & purificación , Orchidaceae/química , Extractos Vegetales/aislamiento & purificación , Plantones/química , Acrilatos/aislamiento & purificación , Alcanos/aislamiento & purificación , Animales , Ácido Ascórbico/aislamiento & purificación , Supervivencia Celular/efectos de los fármacos , Chlorocebus aethiops , Cresoles/aislamiento & purificación , Medios de Cultivo/química , Medios de Cultivo/farmacología , Citotoxinas/farmacología , Cromatografía de Gases y Espectrometría de Masas , Hidroponía/métodos , Ácido Linoleico/aislamiento & purificación , Extracción Líquido-Líquido/métodos , Aceites Volátiles/farmacología , Orchidaceae/metabolismo , Palmitatos/aislamiento & purificación , Pentanoles/aislamiento & purificación , Pentanonas/aislamiento & purificación , Extractos Vegetales/farmacología , Plantas Medicinales , Plantones/metabolismo , Sudáfrica , Estireno/aislamiento & purificación , Células Vero , Ácido alfa-Linolénico/aislamiento & purificación
7.
Molecules ; 26(15)2021 Jul 30.
Artículo en Inglés | MEDLINE | ID: mdl-34361797

RESUMEN

Carpesium divaricatum Sieb. & Zucc., a traditional medicinal plant used as an inflammation-relieving remedy, is a rich source of terpenoids. At least 40 germacrane-type sesquiterpene lactones, representatives of four different structural groups, were isolated from the plant. Cytotoxicity against cancer cells in vitro is the most frequently described biological activity of the compounds. However, little is known about the selectivity of the cytotoxic effect. The anti-inflammatory activity of the germacranolides is also poorly documented. The objective of the present study was to assess the cytotoxic activity of selected C. divaricatum germacranolides-derivatives of 4,5,8,9-tetrahydroxy-3-oxo-germacran-6,12-olide towards cancer and normal cell lines (including cells of different p53 status). Moreover, to assess the anti-inflammatory effect of the compounds, the release of four proinflammatory cytokines/chemokines (IL-1ß, IL-8, TNF-α and CCL2) by lipopolysaccharide-stimulated human neutrophils was measured by ELISA. The investigated sesquiterpene lactones demonstrated nonselective activity towards prostate cancer (Du145 and PC3) and normal prostate epithelial cells (PNT2) as well as against melanoma cells (A375 and HTB140) and keratinocytes (HaCaT). Cytotoxic activity against osteosarcoma cells was independent of their p53 status. In sub-cytotoxic concentrations (0.5-2.5 µM) the studied compounds significantly decreased cytokine/chemokine release by lipopolysaccharide-stimulated human leukocytes.


Asunto(s)
Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/farmacología , Asteraceae/química , Citotoxinas/farmacología , Sesquiterpenos de Germacrano/farmacología , Antiinflamatorios/química , Antiinflamatorios/clasificación , Antiinflamatorios/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/clasificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Asteraceae/metabolismo , Línea Celular , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Quimiocina CCL2/genética , Quimiocina CCL2/inmunología , Citotoxinas/química , Citotoxinas/clasificación , Citotoxinas/aislamiento & purificación , Doxorrubicina/farmacología , Regulación Neoplásica de la Expresión Génica , Humanos , Concentración 50 Inhibidora , Interleucina-1beta/genética , Interleucina-1beta/inmunología , Interleucina-8/genética , Interleucina-8/inmunología , Lipopolisacáridos/antagonistas & inhibidores , Lipopolisacáridos/farmacología , Neutrófilos/citología , Neutrófilos/efectos de los fármacos , Neutrófilos/inmunología , Componentes Aéreos de las Plantas/química , Componentes Aéreos de las Plantas/metabolismo , Extractos Vegetales/química , Plantas Medicinales , Polonia , Cultivo Primario de Células , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/clasificación , Sesquiterpenos de Germacrano/aislamiento & purificación , Transducción de Señal , Factor de Necrosis Tumoral alfa/genética , Factor de Necrosis Tumoral alfa/inmunología , Proteína p53 Supresora de Tumor/genética , Proteína p53 Supresora de Tumor/inmunología
8.
Molecules ; 26(13)2021 Jun 25.
Artículo en Inglés | MEDLINE | ID: mdl-34201912

RESUMEN

Ethnobotanical surveys indicate that the Masai and Kikuyu in Kenya, the Venda in South Africa, and the Gumuz people of Ethiopia use Pappea capensis for the treatment of malaria. The present study aimed to investigate the phytochemical and antiplasmodial properties of the plant leaves. The bioactive compounds were isolated using chromatographic techniques. The structures were established using NMR, HRMS, and UV spectroscopy. Antiplasmodial activity of P. capensis leaf extract and isolated compounds against chloroquine-sensitive 3D7 P. falciparum was evaluated using the parasite lactate dehydrogenase assay. Cytotoxicity against HeLa (human cervix adenocarcinoma) cells was determined using the resazurin assay. The extract inhibited the viability of Plasmodium falciparum by more than 80% at 50 µg/mL, but it was also cytotoxic against HeLa cells at the same concentration. Chromatographic purification of the extract led to the isolation of four flavonoid glycosides and epicatechin. The compounds displayed a similar activity pattern with the extract against P. falciparum and HeLa cells. The results from this study suggest that the widespread use of P. capensis in traditional medicine for the treatment of malaria might have some merits. However, more selectivity studies are needed to determine whether the leaf extract is cytotoxic against noncancerous cells.


Asunto(s)
Antimaláricos , Apiaceae/química , Citotoxinas , Flavonoides , Malaria Falciparum/tratamiento farmacológico , Hojas de la Planta/química , Plasmodium falciparum/crecimiento & desarrollo , Antimaláricos/química , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Células HeLa , Humanos , Malaria Falciparum/metabolismo
9.
ScientificWorldJournal ; 2021: 6622318, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33935597

RESUMEN

Bulbine asphodeloides (L.) Spreng (Xanthorrhoeaceae family), popularly known in South Africa as "ibhucu" or "Balsamkopieva," is a perennial plant traditionally used to treat skin diseases, including sunburns, rough skin, dressing burns, itches, and aging. The present study reports the cytotoxic, cellular antioxidant, and antiglucuronidase properties of the ethanol leaf extract from B. asphodeloides. The cytotoxic effect of the plant extract on human dermal fibroblast (MRHF) cells was evaluated by the bis-Benzamide H 33342 trihydrochloride/propidium iodide (Hoechst 33342/PI) dual-staining method. A validated biological cell-based assay was used to determine the cellular antioxidant activity of the extract. The antiglucuronidase and metal chelating activities were evaluated using standard in vitro methods. Lipopolysaccharide- (LPS-) induced RAW 264.7 cell model was used to determine the anti-inflammatory effect of the plant extract, and the immune-modulatory activity was performed using RAW 264.7 cells. The extract demonstrated no cytotoxic effect towards the MRHF cells at all the tested concentrations. Furthermore, the extract also possessed significant cellular antioxidant and antiglucuronidase activities, but a weak effect of metal chelating activity in a dose-dependent manner. However, the extract showed no significant anti-inflammatory and immune-stimulatory activities. Overall, the results showed that B. asphodeloides may be a useful therapeutic agent for the treatment of skin diseases, therefore supporting its ethnomedicinal usage.


Asunto(s)
Antioxidantes/farmacología , Asphodelaceae/química , Citotoxinas/farmacología , Glucuronidasa/antagonistas & inhibidores , Extractos Vegetales/farmacología , Hojas de la Planta/química , Plantas Medicinales/química , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antioxidantes/aislamiento & purificación , Bioensayo , Quelantes/aislamiento & purificación , Quelantes/farmacología , Citotoxinas/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Etanol , Fibroblastos/efectos de los fármacos , Humanos , Ratones , Extractos Vegetales/aislamiento & purificación , Células RAW 264.7/efectos de los fármacos
10.
J Ethnopharmacol ; 276: 114211, 2021 Aug 10.
Artículo en Inglés | MEDLINE | ID: mdl-34015367

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Dittrichia viscosa (L.) Greuter ("Sari ot, Yapiskan andiz otu" in Turkish) is a medicinal plant that has been traditionally used in the Mediterranean area. This plant is used by the local population for the treatment of cancer. Investigation of their biological activities is therefore very important to be supported by scientific basis for traditional use. AIMS OF THE STUDY: In this study, it is aimed to assess the phytochemical composition, in vitro antioxidant, cytotoxic, and antiproliferative activities of the aqueous and ethanolic extracts obtained from the aerial parts (stems, leaves, flowers) of D. viscosa, collected from two sites in Turkey (Istanbul and Marmaris) against breast and prostate tumor cell lines. MATERIALS AND METHODS: Validated methods were used to evaluate the in vitro antioxidant capacity (DPPH, ABTS, CUPRAC), cytotoxicity (Cell Viability Assay), antiproliferative (Apoptosis assay), and phytochemical compositions. The nepetin (N), 3-O-methylquercetin (Q), and hispidulin (H) in the extracts of D. viscosa were quantified by HPLC and LC-HRMS. Furthermore, in order to control the standards of benefiting from the plant in a healthy way, the contents of some heavy metals were also assessed by ICP-OES in the plant and soil samples as well as the species soil's physical and chemical characteristics. RESULTS: We have found that heavy metal accumulation in the soil does not exceed the allowable limit value except for the nickel. The results showed that ethanol extraction is an efficient strategy to get NQH molecules with a higher content compared with other extraction techniques. However, using the same extraction method revealed that the amount of NQH molecules in the samples of two different regions were variable. The results suggested that all extracts had a high amount of total phenolic content (12.354-22.184 µg GAE/mg) and total flavonoid content (4.442-17.263 µg QE/g). In the antioxidant assay according to the DPPH method, the aqueous ethanol extracts (IC50; 21.00 µg/mL) showed stronger antioxidant activity than BHT. A significant reduction in cell viability was particularly observed in MDA-MB-231 cells, which were sensitive to ethanolic extracts in Istanbul (12-22%) and in Marmaris (14-15%), while PC3 cell lines were also more sensitive to extracts of the aqueous in Istanbul (16%) and the decoction in Marmaris (12%) after 72 h. Especially, it was observed that Marmaris and Istanbul samples induced the toxicity against PC3 cells. CONCLUSION: The study supports the medicinal use of D. viscosa as a potential anticancer against breast and prostate cancer cells in vitro and underlines the immense therapeutic potential of the plant.


Asunto(s)
Antioxidantes/farmacología , Asteraceae/química , Citotoxinas/farmacología , Componentes Aéreos de las Plantas/química , Extractos Vegetales/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Flavonas/análisis , Flavonoides/análisis , Humanos , Concentración 50 Inhibidora , Medicina Tradicional , Fenoles/análisis , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Quercetina/análogos & derivados , Quercetina/análisis , Suelo/química , Turquía
11.
Biomolecules ; 10(11)2020 11 15.
Artículo en Inglés | MEDLINE | ID: mdl-33203123

RESUMEN

Chronic dietary ingestion of suitable phytochemicals may assist with limiting or negating neurodegenerative decline. Current therapeutics used to treat Alzheimer disease elicit broad adverse drug reactions, and alternative sources of cholinesterase inhibitors (ChEIs) are required. Herein, we screened methanolic extracts from seven commonly cultivated plants for their nutraceutical potential; ability to inhibit acetylcholinesterase (AChE) and butyryl-cholinesterase (BuChE), and provision of antioxidant activity through their 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) free radical scavenging capabilities. Potential neurotoxicity of plant extracts was examined via application to SHSY-5Y neuroblastoma cells and quantitation of cell viability. Methanolic extracts of Citrus limon (Lemon), Bombax ceiba (Red silk-cotton), Lawsonia inermis (Henna), Eucalyptus globulus (Eucalyptus), Ocimum basilicum (Basil), Citrus reticulata (Mandarin orange), and Mentha spicata (Spearmint) all displayed concentration-dependent inhibition of AChE and BuChE. The majority of extracts inhibited AChE and BuChE to near equipotency, with Henna and Eucalyptus extracts the two most potent ChEIs. All plant extracts were able to scavenge free radicals in a concentration-dependent manner, with Eucalyptus the most potent antioxidant. Toxicity of plant extracts to neuronal cells was concentration dependent, with Eucalyptus also the most toxic extract. Fractionation of plant extracts and analysis by mass spectrometry identified a number of plant polyphenols that might have contributed to the cholinesterase inhibition: 3-caffeoylquinic acid, methyl 4-caffeoylquinate, kaempferol-acetyl-glycoside, quercetin 3-rutinoside, quercetin-acetyl-glycoside, kaempferol 3-O-glucoside, and quercetin 3-O-glucoside. In silico molecular modeling of these polyphenols demonstrated their improved AChE and BuChE binding affinities compared to the current FDA-approved dual ChEI, galantamine. Collectively, all the plant extracts contained nutraceutical agents as antioxidants and ChEIs and, therefore, their chronic consumption may prove beneficial to combat the pathological deficits that accrue in Alzheimer disease.


Asunto(s)
Inhibidores de la Colinesterasa/uso terapéutico , Suplementos Dietéticos , Enfermedades Neurodegenerativas/prevención & control , Extractos Vegetales/uso terapéutico , Hojas de la Planta , Plantas Medicinales , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Antioxidantes/uso terapéutico , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Supervivencia Celular/fisiología , Inhibidores de la Colinesterasa/aislamiento & purificación , Inhibidores de la Colinesterasa/farmacología , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Citotoxinas/uso terapéutico , Relación Dosis-Respuesta a Droga , Humanos , Simulación del Acoplamiento Molecular/métodos , Enfermedades Neurodegenerativas/metabolismo , Fármacos Neuroprotectores/aislamiento & purificación , Fármacos Neuroprotectores/farmacología , Fármacos Neuroprotectores/uso terapéutico , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Fitoquímicos/uso terapéutico , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología
12.
Pharm Biol ; 58(1): 490-497, 2020 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-32478640

RESUMEN

Context: Mitrephora sirikitiae Weeras., Chalermglin & R.M.K. Saunders (Annonaceae) is a plant endemic to Thailand. Its constituents and their biological activities are unknown.Objective: Isolation and identification of the compounds in the leaves and stems of M. sirikitiae and determination of their cytotoxicity.Materials and methods: Methanol extracts of the leaves and stems of M. sirikitiae were separated by chromatography, and spectroscopic methods were used to determine the structures of the components. The cytotoxicity of the extracts and pure compounds was evaluated using the sulforhodamine B assay with several cell lines. The cells were treated with the compounds at concentrations of 0.16-20 µg/mL for 48 or 72 h.Results: The investigation of the extracts of M. sirikitiae leaves and stems resulted in the isolation of a new lignan, mitrephoran, and 15 known compounds. Among these compounds, 2-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane, ciliaric acid, 6-methoxymarcanine A, and stepharanine were isolated from this genus for the first time. The alkaloids liriodenine and oxoputerine exhibited strong cytotoxicity against all tested cells (IC50 values of 6.59-11.02 µM). In contrast, magnone A, 3',4-O-dimethylcedrusin, and 6-methoxymarcanine A inhibited the growth of some of the tested cells (IC50 values of 2.03-19.73 µM). Magnone A and 6-methoxymarcanine A showed low toxicity for Hek 293 cells (IC50 >20 µM).Discussion and conclusions: M. sirikitiae is a source of cytotoxic lignans and alkaloids. Among the cytotoxic compounds, magnone A and 6-methoxymarcanine A are potentially useful lead compounds for the further development of anticancer agents because of their selective inhibitory effects on cancer cell lines.


Asunto(s)
Annonaceae , Antineoplásicos Fitogénicos/toxicidad , Citotoxinas/toxicidad , Extractos Vegetales/toxicidad , Hojas de la Planta , Células A549 , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Citotoxinas/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Células HEK293 , Células HT29 , Humanos , Células MCF-7 , Extractos Vegetales/aislamiento & purificación , Ratas , Espectrometría de Masa por Ionización de Electrospray/métodos , Tailandia
13.
Molecules ; 25(10)2020 May 20.
Artículo en Inglés | MEDLINE | ID: mdl-32443866

RESUMEN

Phenanthrenoids have been widely described, in the Juncaceae family, for theirbiological properties such as antitumor, anxiolytic, anti-microbial, spasmolytic, and antiinflammatoryactivities. The Juncaceae family is known to contain a large variety ofphenanthrenoids possessing especially anti-inflammatory and cytotoxic properties. Luzulasylvatica, a Juncaceae species, is widely present in the Auvergne region of France, but has neverbeen studied neither for its phytochemical profile nor for its biological properties. We investigatedthe phytochemical profile and evaluated the potential anti-inflammatory activities of L. sylvaticaaerial parts extracts. A bioassay-guided fractionation was carried out to identify the most activefractions. Nine compounds were isolated, one coumarin 1 and eight phenanthrene derivatives (2-9), including four new compounds (4, 5, 8 and 9), from n-hexane and CH2Cl2, fractions. Theirstructures were established by HRESIMS, 1D and 2D NMR experiments. The biological properties,especially the anti-inflammatory/antioxidant activities (ROS production) and antiproliferativeactivity on THP-1, a monocytic leukemia cell line, of each compound, were evaluated. Threephenanthrene derivatives 4, 6, and 7 showed very promising antiproliferative activities.Phenanthrene derivatives.


Asunto(s)
Cumarinas/química , Citotoxinas/química , Magnoliopsida/química , Fenantrenos/química , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Cumarinas/aislamiento & purificación , Cumarinas/farmacología , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Humanos , Fenantrenos/aislamiento & purificación , Fenantrenos/farmacología , Extractos Vegetales/química , Extractos Vegetales/farmacología , Semillas/química
14.
Molecules ; 25(10)2020 May 20.
Artículo en Inglés | MEDLINE | ID: mdl-32443927

RESUMEN

Diterpenes are characteristic compounds from the genus Sideritis L., possessing an array of biological activities. Siderol is the main constituent of the ent-kaurene diterpenes in Sideritis species. In order to isolate the specific compound and evaluate for the first time its cytotoxic activity, we explored the dichloromethane extract of cultivated Sideritis euboea Heldr. To track the specific natural bioactive agent, we applied NMR spectroscopy to the crude plant extract, since NMR can serve as a powerful and rapid tool both to navigate the targeted isolation process of bioactive constituents, and to also reveal the identity of bioactive components. Along these lines, from the rapid 1D 1H NMR spectrum of the total crude plant extract, we were able to determine the characteristic proton NMR signals of siderol. Furthermore, with the same NMR spectrum, we were able to categorize several secondary metabolites into chemical groups as a control of the isolation process. Therefore, this non-polar extract was explored, for the first time, revealing eleven compounds-one fatty acid ester; 2-(p-hydroxyphenyl)ethylstearate (1), three phytosterols; ß-sitosterol (2), stigmasterol (3), and campesterol (4); one triterpenoid; ursolic acid (5), four diterpenoids; siderol (6), eubol (7), eubotriol (8), 7-epicandicandiol (9) and two flavonoids; xanthomicrol (10) and penduletin (11). The main isolated constituent was siderol. The antiproliferative potential of siderol was evaluated, using the MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide) assay, on three human cancer cell lines DLD1, HeLa, and A549, where the IC50 values were estimated at 26.4 ± 3.7, 44.7 ± 7.2, and 46.0 ± 4.9 µΜ, respectively. The most potent activity was recorded in the human colon cancer cell line DLD1, where siderol exhibited the lowest IC50. Our study unveiled the beneficial potential of siderol as a remarkable cytotoxic agent and the significant contribution of NMR spectroscopy towards the isolation and identification of this potent anticancer agent.


Asunto(s)
Citotoxinas/aislamiento & purificación , Diterpenos/química , Sideritis/química , Triterpenos/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Proliferación Celular/efectos de los fármacos , Citotoxinas/química , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Flavonas/química , Humanos , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Extractos Vegetales/farmacología , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Ácido Ursólico
15.
Molecules ; 25(7)2020 Mar 29.
Artículo en Inglés | MEDLINE | ID: mdl-32235298

RESUMEN

Girardinia diversifolia, also known as Himalayan nettle, is a perennial herb used in Nepal to make fiber as well as in traditional medicine for the treatment of several diseases. To date, phytochemical studies and biological assays on this plant are scarce. Thus, in the present work, the G. diversifolia extracts have been evaluated for their potential pharmaceutical, cosmetic and nutraceutical uses. For this purpose, detailed phytochemical analyses were performed, evidencing the presence of phytosterols, fatty acids, carotenoids, polyphenols and saponins. The most abundant secondary metabolites were ß- and γ-sitosterol (11 and 9% dw, respectively), and trans syringin (0.5 mg/g) was the most abundant phenolic. Fatty acids with an abundant portion of unsaturated derivatives (linoleic and linolenic acid at 22.0 and 9.7 mg/g respectively), vitamin C (2.9 mg/g) and vitamin B2 (0.12 mg/g) were also present. The antioxidant activity was moderate while a significant ability to inhibit acetylcholinesterase (AChE), butyrilcholinesterase (BuChE), tyrosinase, α-amylase and α-glucosidase was observed. A cytotoxic effect was observed on human ovarian, pancreatic and hepatic cancer cell lines. The effect in hepatocarcinoma cells was associated to a downregulation of the low-density lipoprotein receptor (LDLR), a pivotal regulator of cellular cholesterol homeostasis. These data show the potential usefulness of this species for possible applications in pharmaceuticals, nutraceuticals and cosmetics.


Asunto(s)
Anticolesterolemiantes/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Citotoxinas/aislamiento & purificación , Inhibidores Enzimáticos/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Urticaceae/química , Anticolesterolemiantes/farmacología , Antioxidantes/farmacología , Ácido Ascórbico/aislamiento & purificación , Ácido Ascórbico/farmacología , Carotenoides/aislamiento & purificación , Carotenoides/farmacología , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Citotoxinas/farmacología , Inhibidores Enzimáticos/farmacología , Ácidos Grasos/aislamiento & purificación , Ácidos Grasos/farmacología , Glucósidos/aislamiento & purificación , Glucósidos/farmacología , Humanos , Fenilpropionatos/aislamiento & purificación , Fenilpropionatos/farmacología , Fitoquímicos/farmacología , Fitosteroles/aislamiento & purificación , Fitosteroles/farmacología , Extractos Vegetales/química , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Receptores de LDL/antagonistas & inhibidores , Receptores de LDL/genética , Receptores de LDL/metabolismo , Riboflavina/aislamiento & purificación , Riboflavina/farmacología , Saponinas/aislamiento & purificación , Saponinas/farmacología , Sitoesteroles/aislamiento & purificación , Sitoesteroles/farmacología
16.
Molecules ; 25(3)2020 Jan 29.
Artículo en Inglés | MEDLINE | ID: mdl-32013272

RESUMEN

Searching for new bio-based herbicides is crucial for decreasing chemical pollution, protecting the environment, and sustaining biodiversity. Origanum vulgare is considered a promising source of essential oil with herbicidal effect. The mode of action is not known. The present study focused on (1) comparison of phytotoxic activity of Origanum vulgare EO on monocot (Triticum aestivum and Hordeum vulgare) and dicot species (Lepidium sativum and Sinapis alba); (2) and evaluating other antimicrobial biological activities against phytopatogen bacteria (Clavibacter michiganensis, Pseudomonas syringae pv. phaseolicola, Pseudomonas savastanoi, and Xanthomonas campestris); antifungal activity against Monilinia fructicola, Aspergillus niger, Penicillium expansum, and Botrytis cinerea; cytotoxic activity and antioxidant activity. According to the GC/MS analyses, the EO belongs to the thymol chemotype O. vulgare with its high content of thymol (76%). Germination of all four species was not influenced by EO. The phytotoxic effect was statistically significant in the monocot species, while in the dicot species the opposite was observed-a stimulation effect, which was also statistically significant. Strong biological activity of O. vulgare EO was noted on all phytopatogen bacteria and fungi in the highest dose. Cytotoxic activity showed an IC50 = 50.5 µg/mL. Antioxidant activity showed an IC50 = 106.6 µg/mL after 45 min experimental time. Based on the presented results, it is possible to conclude that thymol chemotype O. vulgare essential oil could be potentially used as a herbicide with selective effects on monocot plant species.


Asunto(s)
Herbicidas/farmacología , Aceites Volátiles/farmacología , Origanum/química , Aceites de Plantas/farmacología , Plantas/efectos de los fármacos , Timol/farmacología , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Depuradores de Radicales Libres , Cromatografía de Gases y Espectrometría de Masas , Herbicidas/aislamiento & purificación , Hordeum/efectos de los fármacos , Humanos , Lepidium sativum/efectos de los fármacos , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Aceites de Plantas/química , Aceites de Plantas/aislamiento & purificación , Sinapis/efectos de los fármacos , Especificidad de la Especie , Timol/química , Timol/aislamiento & purificación , Triticum/efectos de los fármacos
17.
Nat Prod Res ; 34(4): 585-589, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-30445838

RESUMEN

Phytochemical study on the extract of Vietnamese medicinal plant Helicteres hirsuta Lour. has led to the isolation and structural elucidation of twelve secondary metabolites, 3-O-trans-caffeoylbetulinic acid (1), 3ß-benzoylbetulinic acid (2), betulinic acid methyl ester (3), betulinic acid (4), lupeol (5), 4-hydroxybenzoic acid (6), 3,4-dihydroxybenzoic acid methyl ester (7), 4-hydroxy-3,5-dimethoxybenzoic acid (8), 5,8-dihydroxy-7,4'-dimethoxyflavone (9), isoscutellarein 4'-methyl ether 8-O-ß-D-glucopyranoside (10), methyl caffeate (11) and stigmasterol (12). Especially, compound 2 was reported as a new natural product. Their structures were elucidated by a combination of 2D NMR and ESI-FT-ICR-MS spectroscopies. Furthermore, eight compounds were tested for their cytotoxicity against five cancer cell lines (Hela, HepG2, SK-LU-1, AGS and SK-MEL-2). The results showed that compounds (1, 3-5, 9) have moderate activities. This is the first study on the chemical constituents and their cytotoxicity of the Vietnamese Helicteres hirsuta L.


Asunto(s)
Citotoxinas/aislamiento & purificación , Malvaceae/química , Fitoquímicos/análisis , Plantas Medicinales/química , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Línea Celular Tumoral , Citotoxinas/química , Citotoxinas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Triterpenos/análisis , Vietnam
18.
Nat Prod Res ; 34(15): 2167-2172, 2020 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-30835538

RESUMEN

The CHCl3 fraction of MeOH extract of Periploca somaliensis (family Asclepiadaceae) fruits afforded a new scalarane sesterterpene, namely perisomalien A (1), along with lupeol acetate (2), ß-amyrin (3), cycloart-23Z-ene-3ß,25-diol (4), and ß-sitosterol-3-O-ß-D-glucopyranoside (5). Their chemical structures were established by various spectroscopic analyses, in addition to comparison with the formerly reported data. Moreover, the cytotoxic activity of these metabolites was assessed towards MCF-7, HepG2, and HCT-116 tumour cell lines using sulforhodamine B (SRB) assay. Compound 4 showed the most potent cytotoxic profile with IC50 9.0 µM towards MCF-7, compared to doxorubicin (IC50 0.18 µM). Also, 1 and 4 possessed the most potent effect towards HepG2 with IC50s 26.7 and 25.9 µM, respectively. In addition, all tested compounds showed cytotoxic effects with IC50 values ranging from 19.9 to 39.3 µM against HCT-116.


Asunto(s)
Periploca/química , Extractos Vegetales/química , Sesterterpenos/química , Sesterterpenos/farmacología , Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Línea Celular Tumoral , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Frutas/química , Humanos , Concentración 50 Inhibidora , Magnoliopsida , Ácido Oleanólico/farmacología , Triterpenos Pentacíclicos/aislamiento & purificación , Extractos Vegetales/farmacología , Sesterterpenos/aislamiento & purificación
19.
Nat Prod Res ; 34(8): 1091-1096, 2020 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-30663360

RESUMEN

A new γ-pyrone derivative, acrepyrone A (1), and three known sorbicillinoids, trichodimerol (2), dihydrotrichodimerol (3) and tetrahydrotrichodimerol (4) were isolated from an endophytic fungus, Acremonium citrinum SS-g13, harboured in the roots of the Chinese medicinal plant Fructus mori. Their structures were determined by analysing MS, NMR, and ECD data. Compound 1 was evaluated for its cytotoxic effect, antibacterial activity and quorum sensing inhibitory potential.


Asunto(s)
Acremonium/química , Plantas Medicinales/microbiología , Pironas/aislamiento & purificación , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Endófitos/química , Humanos , Estructura Molecular , Raíces de Plantas/efectos de los fármacos , Pironas/química , Percepción de Quorum/efectos de los fármacos
20.
Nat Prod Res ; 34(13): 1937-1941, 2020 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-30691284

RESUMEN

The objective of this study was to compare the antioxidant activity and cytotoxicity of Durio zibethinus M. (Durian) leaf extract from two extraction methods. Ultrasound-assisted extraction and Accelerated-solvent extraction were used to produce crude extract. The results revealed that UAE achieved 3× higher in total phenolic content in the leaf extract compared to ASE. DPPH radical scavenging activity was 4.6× higher in leaf extract from ASE. No significant differences reported in ferric reducing power, and total flavonoid content of the leaf extract between the two methods. Cytotoxicity via MTT assay demonstrated no significant differences in cell viability upon exposure to the leaf extract from both methods. This suggested that they were appropriate in producing Durio zibethinus M. leaf extract for end use application in food related product. Both ensured similar level of safety in Durio zibethinus M. leaf extract as a new potential ingredient for the food industry.


Asunto(s)
Antioxidantes/aislamiento & purificación , Bombacaceae/química , Extractos Vegetales/química , Antioxidantes/farmacología , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Flavonoides/análisis , Depuradores de Radicales Libres/análisis , Análisis de Peligros y Puntos de Control Críticos , Fenoles/análisis , Solventes/química , Ondas Ultrasónicas
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