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1.
Int J Mol Sci ; 25(13)2024 Jul 05.
Artículo en Inglés | MEDLINE | ID: mdl-39000493

RESUMEN

Plants from the Fabaceae family are widely distributed around the world, especially in Europe, Asia and North America. They are a rich source of isoflavones, compounds with estrogen-like activity, which are suspected of having a chemopreventive effect against hormone-dependent cancers. Following the PRISMA guidelines, we conducted a systematic review aimed at assessing the impact of Fabaceae plant extracts on hormone-dependent cancer cells and the content of active compounds in plant raw materials. We analyzed the results of 63 articles from in vitro and in vivo studies describing the effect of plant extracts containing isoflavones on cancer cells, along with their anti-inflammatory and antioxidant potential. In the process, we determined the research limitations and future research directions. The collected results indicate the plant species with potentially high contents of phytoestrogens and anti-inflammatory, antioxidant and cytotoxic properties. They point to the potential use of plants in the diet as a source of compounds offering cancer prevention.


Asunto(s)
Fabaceae , Isoflavonas , Neoplasias , Extractos Vegetales , Humanos , Isoflavonas/farmacología , Fabaceae/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Neoplasias/prevención & control , Antioxidantes/farmacología , Animales , Quimioprevención/métodos , Fitoestrógenos/farmacología , Antiinflamatorios/farmacología
2.
Int J Mol Sci ; 25(7)2024 Apr 03.
Artículo en Inglés | MEDLINE | ID: mdl-38612798

RESUMEN

Brassica vegetables are widely consumed all over the world, especially in North America, Asia, and Europe. They are a rich source of sulfur compounds, such as glucosinolates (GLSs) and isothiocyanates (ITCs), which provide health benefits but are also suspected of having a goitrogenic effect. Adhering to PRISMA guidelines, we conducted a systematic review to assess the impact of dietary interventions on thyroid function, in terms of the potential risk for people with thyroid dysfunctions. We analyzed the results of 123 articles of in vitro, animal, and human studies, describing the impact of brassica plants and extracts on thyroid mass and histology, blood levels of TSH, T3, T4, iodine uptake, and the effect on thyroid cancer cells. We also presented the mechanisms of the goitrogenic potential of GLSs and ITCs, the limitations of the studies included, as well as further research directions. The vast majority of the results cast doubt on previous assumptions claiming that brassica plants have antithyroid effects in humans. Instead, they indicate that including brassica vegetables in the daily diet, particularly when accompanied by adequate iodine intake, poses no adverse effects on thyroid function.


Asunto(s)
Brassica , Glándula Tiroides , Verduras , Humanos , Brassica/química , Glándula Tiroides/metabolismo , Animales , Verduras/química , Glucosinolatos , Yodo , Isotiocianatos/farmacología
3.
Int J Mol Sci ; 25(11)2024 May 22.
Artículo en Inglés | MEDLINE | ID: mdl-38891815

RESUMEN

The growing trend in fruit wine production reflects consumers' interest in novel, diverse drinking experiences and the increasing demand for healthier beverage options. Fruit wines made from kiwi, pomegranates, and persimmons fermented using S. bayanus Lalvin strain EC1118 demonstrate the versatility of winemaking techniques. Kiwifruit, persimmon, and pomegranate wines were analyzed using HPLC and GC-TOFMS analyses to determine their concentrations of phenolic acids and volatile compounds. These results were supported by Fourier transform infrared (FTIR) spectroscopy to characterize and compare chemical shifts in the polyphenol regions of these wines. The wines' characterization included an anti-inflammatory assay based on NO, TNF-alpha, and IL-6 production in the RAW 264.7 macrophage model. FTIR spectroscopy predicted the antioxidant and phenolic contents in the wines. In terms of polyphenols, predominantly represented by chlorogenic, caffeic, and gallic acids, pomegranate and kiwifruit wines showed greater benefits. However, kiwifruit wines exhibited a highly diverse profile of volatile compounds. Further analysis is necessary, particularly regarding the use of other microorganisms in the fermentation process and non-Saccharomyces strains methods. These wines exhibit high biological antioxidant potential and health properties, providing valuable insights for future endeavors focused on designing healthy functional food products.


Asunto(s)
Antiinflamatorios , Fermentación , Frutas , Saccharomyces cerevisiae , Compuestos Orgánicos Volátiles , Vino , Vino/análisis , Compuestos Orgánicos Volátiles/análisis , Compuestos Orgánicos Volátiles/metabolismo , Ratones , Saccharomyces cerevisiae/metabolismo , Antiinflamatorios/farmacología , Antiinflamatorios/análisis , Antiinflamatorios/química , Frutas/química , Frutas/metabolismo , Animales , Células RAW 264.7 , Espectroscopía Infrarroja por Transformada de Fourier/métodos , Polifenoles/análisis , Antioxidantes/análisis , Actinidia/química , Granada (Fruta)/química
4.
Molecules ; 29(5)2024 Feb 28.
Artículo en Inglés | MEDLINE | ID: mdl-38474555

RESUMEN

BACKGROUND: Prostate cancer (PC) and benign prostatic hyperplasia (BPH) are common health problems in the aging male population. Due to the unexplored and unconfirmed impact of food containing isoflavones, like sprouts, on the development of the management of BPH and prostate cancer, we decided to extend the knowledge in this area. RESULTS: We have demonstrated for the first time that chickpea sprouts may play an important role in the chemoprevention of prostate disorders. However, attention should be paid to the isoflavone content in the sprouts, as in our study, chickpea sprouts with a moderate concentration of the compounds, harvested in natural light conditions (CA10L) and blue LED light (CA7B), showed the best scores in terms of their potential towards prostate disorders. METHODS: Chickpea seeds were grown in LED chambers. The methanol extracts from sprouts were quantitatively defined using the HPLC system. Experiments such as the determination of PSA, 5-α-reductase, and dihydrotestosterone were performed on PNT2 and LNCaP cells. For anti-inflammatory assays (determination of NO, IL-6, and TNF-alpha release), murine RAW264.7 macrophages were used. CONCLUSIONS: The role of legume products as a diet element should be deeply evaluated for the development of future dietary recommendations for prostate cancer and BPH prevention.


Asunto(s)
Cicer , Isoflavonas , Hiperplasia Prostática , Neoplasias de la Próstata , Masculino , Humanos , Animales , Ratones , Cicer/química , Próstata , Isoflavonas/química , Dieta
5.
Molecules ; 29(16)2024 Aug 10.
Artículo en Inglés | MEDLINE | ID: mdl-39202875

RESUMEN

Plants from the Amaranthaceae family are a source of oleanolic acid (OA)-type saponins with cytotoxic activity. Two known OA-type saponins, calenduloside E and chikusetsusaponin IVa, were isolated from the roots of Chenopodium strictum Roth. Their structures were confirmed using MS and NMR techniques. This constitutes the inaugural report of the saponins in Ch. strictum. Both the isolated saponins and structurally similar compounds, momordin Ic and OA, were compared for their cytotoxicity against various cancer and normal cell lines (including skin, breast, thyroid, gastrointestinal, and prostate panels). Their effects were dose- and time-dependent, varying with the specific cell line and compound structure. A chemometric approach demonstrated the effects of the compounds on the cell lines. The study discusses the structure-activity observations. The key structural elements for potent cytotoxic activity included the free carboxyl group 28COOH in the sapogenin structure (OA) and the presence of a sugar moiety. The monodesmosides with glucuronic acid (GlcA) at the C3 position of OA were generally more cytotoxic than bidesmosides or OA alone. The addition of xylose in the sugar chain modified the activity towards the cancer cells depending on the specific cell line. OA-type saponins with GlcA (particularly calenduloside E and momordin Ic) represent a promising avenue for further investigation as potential anticancer agents.


Asunto(s)
Antineoplásicos Fitogénicos , Ácido Oleanólico , Saponinas , Humanos , Saponinas/farmacología , Saponinas/química , Saponinas/aislamiento & purificación , Ácido Oleanólico/química , Ácido Oleanólico/farmacología , Línea Celular Tumoral , Relación Estructura-Actividad , Antineoplásicos Fitogénicos/farmacología , Antineoplásicos Fitogénicos/química , Amaranthaceae/química , Estructura Molecular , Extractos Vegetales/farmacología , Extractos Vegetales/química , Ensayos de Selección de Medicamentos Antitumorales , Supervivencia Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos
6.
Plant Foods Hum Nutr ; 79(1): 151-158, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38231454

RESUMEN

Amaranth, quinoa, and buckwheat are the representatives of pseudocereals, different parts and by-products of which are used in daily nutrition and food processing industry. However, only scarce information exists on the bioactivity of their oils. Thus, oils obtained from amaranth, buckwheat, and red, yellow, and white quinoa seeds were evaluated in terms of their nutritional (fatty acid profile, squalene), cytotoxic (against normal and neoplastic gastrointestinal, prostate, and skin cells), anti-inflammatory and antiradical (interleukin 6, TNF-alpha, nitric oxide, DPPH, Total phenolics, and superoxide dismutase) potential in the in vitro model. Linoleic (42.9-52.5%) and oleic (22.5-31.1%) acids were the two main unsaturated, while palmitic acid (4.9-18.6%) was the major saturated fatty acid in all evaluated oils. Squalene was identified in all evaluated oils with the highest content in amaranth oil (7.6 g/100 g), and the lowest in buckwheat oil (2.1 g/100 g). The evaluated oils exerted a high direct cytotoxic impact on cancer cells of different origins, but also revealed anti-inflammatory and antiradical potentials. Yellow quinoa oil was the most active, especially toward skin (A375; IC50 6.3 µg/mL), gastrointestinal (HT29 IC50 4.9 µg/mL), and prostate cancer cells (LNCaP IC50 7.6 µg/mL). The observed differences in the activity between the oils from the tested quinoa varieties deserve further studies. High selectivity of the oils was noted, which indicates their safety to normal cells. The obtained results indicate that the oils are good candidates for functional foods with perspective chemopreventive potential.


Asunto(s)
Semillas , Escualeno , Escualeno/análisis , Espectroscopía Infrarroja por Transformada de Fourier , Semillas/química , Ácidos Grasos/análisis , Aceites de Plantas/análisis , Antiinflamatorios/farmacología , Antiinflamatorios/análisis
7.
Molecules ; 28(4)2023 Feb 17.
Artículo en Inglés | MEDLINE | ID: mdl-36838911

RESUMEN

Erucic acid (EA) is monounsaturated fatty acid (22:1 n-9), synthesized in the seeds of many plants from the Brassicaceae family, with Brassica napus, B. rapa, or B. carinata considered as its richest source. As the compound has been blamed for the poisoning effect in Toxic Oil Syndrome, and some data indicated its cardiotoxicity to rats, EA has been for decades classified as toxic substance, the use of which should be avoided. However, the cardiac adverse effects of EA have not been confirmed in humans, and the experiments in animal models had many limitations. Thus, the aim of this review was to present the results of the so far published studies on both toxic, and pharmacological properties of EA, trying to answer the question on its future medicinal use. Despite the ambiguous and relatively small data on toxic and beneficial effects of EA it seems that the compound is worth investigating. Further research should be particularly directed at the verification EA toxicity, more in-depth studies on its neuroprotective and cytotoxic properties, but also its use in combination with other drugs, as well as its role as a drug carrier.


Asunto(s)
Brassica napus , Ácidos Erucicos , Humanos , Ratas , Animales , Ácidos Grasos Monoinsaturados , Semillas
8.
Molecules ; 28(2)2023 Jan 04.
Artículo en Inglés | MEDLINE | ID: mdl-36677535

RESUMEN

Plants of the genus Pulicaria are known for providing traditional medicines, spices, herbal teas, and insect deterrents. Pulicaria inuloides (Poir.). DC. is one of the less chemically studied species within the genus. Hydroalcoholic extracts from roots and aerial parts of P. inuloides were analyzed using the UHPLC-PAD-MSn technique and revealed the presence of six caffeoylquinic and eleven caffeoylhexaric conjugates together with hydroxykaempferol dimethyl ether and quercetagetin trimethyl ether. Moreover, constituents of chloroform extract from the whole P. inuloides plants were isolated and identified by spectroscopic methods. One new and four known caryophyllene derivatives, three thymol derivatives, and four polymethoxylated flavonols were found in the analyzed extract. The structure of the new compound was established by spectroscopic methods (HRESIMS, 1H NMR, 13C NMR, COSY, HSQC, HMBC, NOESY). The cytotoxicity of 6-Hydroxykaempferol 3,7-dimethyl ether and quercetagetin 3,7,3'-trimethyl ether (chrysosplenol C), which are major flavonols isolated from the plant, were tested on prostate epithelial cells (PNT2), prostate cancer cells (DU145 and PC3), human keratinocytes (HaCaT), and melanoma cells (HTB140 and A375). Both flavonols demonstrated moderate cytotoxic activity against PC3 cells (IC50 = 59.5 µM and 46.6 µM, respectively). The remaining cell lines were less affected (IC50 > 150 µM).


Asunto(s)
Antineoplásicos , Éteres Metílicos , Pulicaria , Humanos , Flavonoles/farmacología , Pulicaria/química , Extractos Vegetales/farmacología , Extractos Vegetales/química
9.
Molecules ; 28(23)2023 Nov 24.
Artículo en Inglés | MEDLINE | ID: mdl-38067491

RESUMEN

Melanoma is one of the most dangerous forms of skin cancer, characterized by early metastasis and rapid development. In search for effective treatment options, much attention is given to triterpenoids of plant origin, which are considered promising drug candidates due to their well described anticancer properties and relatively low toxicity. This paper comprehensively summarizes the antimelanoma potential of natural triterpenoids, that are also used as scaffolds for the development of more effective derivatives. These include betulin, betulinic acid, ursolic acid, maslinic acid, oleanolic acid, celastrol and lupeol. Some lesser-known triterpenoids that deserve attention in this context are 22ß-hydroxytingenone, cucurbitacins, geoditin A and ganoderic acids. Recently described mechanisms of action are presented, together with the results of preclinical in vitro and in vivo studies, as well as the use of drug delivery systems and pharmaceutical technologies to improve the bioavailability of triterpenoids. This paper also reviews the most promising structural modifications, based on structure-activity observations. In conclusion, triterpenoids of plant origin and some of their semi-synthetic derivatives exert significant cytotoxic, antiproliferative and chemopreventive effects that can be beneficial for melanoma treatment. Recent data indicate that their poor solubility in water, and thus low bioavailability, can be overcome by complexing with cyclodextrins, or the use of nanoparticles and ethosomes, thus making these compounds promising antimelanoma drug candidates for further development.


Asunto(s)
Antineoplásicos , Melanoma , Triterpenos , Humanos , Disponibilidad Biológica , Melanoma/tratamiento farmacológico , Triterpenos/farmacología , Triterpenos/química , Antineoplásicos/química
10.
Molecules ; 28(3)2023 Jan 18.
Artículo en Inglés | MEDLINE | ID: mdl-36770647

RESUMEN

The genus Atriplex provides species that are used as food and natural remedies. In this work, the levels of soluble phenolic acids (free and conjugated) and flavonoids in extracts from roots, stems, leaves and flowers of the unexplored Atriplex sagittata Borkh were investigated by LC-ESI-MS/MS, together with their antioxidant and antihyaluronidase activity. Phenolic acids were present in all parts of A. sagittata; and were most abundant in the leaves (225.24 µg/g dw.), whereas the highest content of flavonoids were found in the flowers (242.71 µg/g dw.). The most common phenolics were 4-hydroxybenzoic and salicylic acids, kaempferol-3-glucoside-7-rhamnoside, kaempferol-3-rutinoside and the rare narcissoside, which was present in almost all morphotic parts. The stem extract had the highest antioxidant activity and total phenolic content (611.86 mg/100 g dw.), whereas flower extract exerted the most potent antihyaluronidase effect (IC50 = 84.67 µg/mL; control-quercetin: IC50 = 514.28 µg/mL). Phytochemical analysis of the flower extract led to the isolation of two triterpene saponins that were shown to be strong hyaluronidase inhibitors (IC50 = 33.77 and 168.15 µg/mL; control-escin: IC50 = 307.38 µg/mL). This is the first report on the presence of phenolics and saponins in A. sagittata. The results suggest that both groups of metabolites may contribute to the overall activity of this plant species.


Asunto(s)
Atriplex , Saponinas , Antioxidantes/química , Quempferoles , Extractos Vegetales/química , Saponinas/farmacología , Espectrometría de Masas en Tándem/métodos , Hialuronoglucosaminidasa , Fenoles/química , Flavonoides/química
11.
Molecules ; 28(5)2023 Feb 22.
Artículo en Inglés | MEDLINE | ID: mdl-36903308

RESUMEN

Due to problems with selenium deficiency in humans, the search for new organic molecules containing this element in plant biofortification process is highly required. Selenium organic esters evaluated in this study (E-NS-4, E-NS-17, E-NS-71, EDA-11, and EDA-117) are based mostly on benzoselenoate scaffolds, with some additional halogen atoms and various functional groups in the aliphatic side chain of different length, while one compound contains a phenylpiperazine moiety (WA-4b). In our previous study, the biofortification of kale sprouts with organoselenium compounds (at the concentrations of 15 mg/L in the culture fluid) strongly enhanced the synthesis of glucosinolates and isothiocyanates. Thus, the study aimed to discover the relationships between molecular characteristics of the organoselenium compounds used and the amount of sulfur phytochemicals in kale sprouts. The statistical partial least square model with eigenvalues equaled 3.98 and 1.03 for the first and second latent components, respectively, which explained 83.5% of variance in the predictive parameters, and 78.6% of response parameter variance was applied to reveal the existence of the correlation structure between molecular descriptors of selenium compounds as predictive parameters and biochemical features of studied sprouts as response parameters (correlation coefficients for parameters in PLS model in the range-0.521 ÷ 1.000). This study supported the conclusion that future biofortifiers composed of organic compounds should simultaneously contain nitryl groups, which may facilitate the production of plant-based sulfur compounds, as well as organoselenium moieties, which may influence the production of low molecular weight selenium metabolites. In the case of the new chemical compounds, environmental aspects should also be evaluated.


Asunto(s)
Brassica , Compuestos de Organoselenio , Compuestos de Selenio , Selenio , Humanos , Selenio/metabolismo , Brassica/química , Compuestos de Azufre/metabolismo
12.
Chem Biodivers ; 19(7): e202200408, 2022 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-35652525

RESUMEN

In this study, the cytotoxic activity of acetone extracts of Cladonia mitis was assessed with respect to the content of usnic acid, a secondary metabolite commonly present in this species. Following quantitative HPLC analysis of the extracts, usnic acid was isolated by preparative chromatography. The study of cytotoxic activity was performed using the MTT test on three melanoma cell lines - HTB140, A375 and WM793. The selectivity of action was also assessed by comparing the effect towards normal human keratinocytes HaCaT. The results showed a dose-dependent cytotoxic activity of the extracts tested and usnic acid itself, but no relationship was found between the content of usnic acid and the activity of the extracts. Furthermore, the extracts showed varied, but rather low anti-tyrosinase activity. Other in vitro and in vivo studies are necessary to demonstrate that C. mitis extracts may be useful in the adjuvant external treatment of skin melanoma.


Asunto(s)
Antineoplásicos , Líquenes , Melanoma , Acetona , Antineoplásicos/farmacología , Ascomicetos , Benzofuranos , Humanos , Líquenes/química , Melanoma/tratamiento farmacológico
13.
Molecules ; 27(24)2022 Dec 18.
Artículo en Inglés | MEDLINE | ID: mdl-36558162

RESUMEN

Among all legumes sprouts' active compounds, isoflavones seem to be the most important; nevertheless, their high content is not always associated with beneficial effects. These compounds may prevent or stimulate hormone-dependent cancers due to their estrogen-like activity. Different LED light quality can change the synthesis of active compounds and significantly influence the biological activity of the sprouts. This study aimed to evaluate the effects of LED light (red, blue, green, yellow), as well as total darkness, and natural light conditions (as reference), on isoflavones content, determined by HPLC-UV-VIS, during 10 days of harvesting of chickpea and lupin sprouts. Due to the ambiguous estrogenic potential of isoflavones, the impact of these sprouts on normal and cancer prostate and breast cells was evaluated. Yellow LED light resulted in the highest sum of isoflavones in chickpea sprouts (up to 1 g/100 g dw), while for green LED light, the isoflavones sum was the lowest. The exact opposite effect was noted for lupin sprouts, with the predominance of green over the yellow LED light. The examined sprouts were of high safety to non-neoplastic breast and prostate cells, with interesting cytotoxic effects on breast MCF7 and prostate DU145 cancer cells. No clear relationship was observed between the activity and isoflavones content.


Asunto(s)
Cicer , Isoflavonas , Lupinus , Isoflavonas/farmacología , Alimentos Funcionales , Próstata
14.
Molecules ; 27(22)2022 Nov 16.
Artículo en Inglés | MEDLINE | ID: mdl-36432013

RESUMEN

Rapanone is a plant-derived simple alkyl-dihydroxybenzoquinone structurally close to embelin, a well-known cytotoxic agent. The pharmacological characterization of rapanone is still incomplete, and to fill the data gap, a good source for its acquisition is required to conduct further research. This study aimed to optimize the conditions for the extraction of rapanone from the leaves of white-berried Ardisia crenata Sims. For this purpose, three methods were employed: heat reflux (HRE), shaking (SE), and ultrasound-assisted extraction (UAE), and such parameters as the extraction time, solvent, and the number of extractions from the same sample were set as experimental variables. Furthermore, cytotoxic activity toward prostate cancer, thyroid cancer, and colorectal carcinoma cell lines was investigated and compared with doxorubicin and embelin. The most effective and economical method for the extraction of rapanone was shown to be 20 min UAE with ethyl acetate or chloroform. Rapanone exhibited high cytotoxic activity against PC3 (IC50 = 6.50 µg/mL), Du145 (IC50 = 7.68 µg/mL), FTC133 (IC50 = 6.01 µg/mL), 8505C (IC50 = 7.84 µg/mL), and Caco-2 (IC50 = 8.79 µg/mL) cell lines after 24 h and against the HT29 cell line after 48 h (IC50 = 11.67 µg/mL). Furthermore, it revealed a more favorable safety profile than either its homologue, embelin, or doxorubicin. The set of optimal extraction parameters obtained may be utilized for scientific and industrial purposes to achieve the best rapanone yield. Moreover, this benzoquinone revealed a high cytotoxic activity with good selectivity.


Asunto(s)
Antineoplásicos , Benzoquinonas , Masculino , Humanos , Células CACO-2 , Benzoquinonas/farmacología , Antineoplásicos/farmacología , Doxorrubicina
15.
Chem Biodivers ; 18(11): e2100552, 2021 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-34669249

RESUMEN

In this study, two ursane-type triterpenes, i. e., ursolic acid (UA) and 3-O-ß-acetoxyursolic acid (AUA), were isolated and quantified in Sorbus intermedia (EHRH.) PERS. fruits. UA and AUA levels differed slightly throughout fruit maturation, and both triterpenes showed similar dynamics of accumulation with the highest levels found in ripe fruits (up to 6.33±0.56 and 1.17±0.18 mg/g dw. of UA and AUA, respectively). The extracts derived from unripe fruits displayed significant cytotoxic effects against WM793, DU-145, PC3, 8505C, Caco2 and A549 cells, but no correlation between UA and AUA levels and cytotoxicity was found. On the other hand, extracts from mature fruits were not active towards almost all of the tested cell lines. The chemometric approach showed that the extracts derived from fruits harvested earlier clustered to form a clearly distanced group from extracts prepared from more-mature fruits. The extracts at higher concentrations formed separate groups, which indicated the concentration-dependent effect of these extracts on the cells.


Asunto(s)
Antineoplásicos/farmacología , Frutas/química , Sorbus/química , Triterpenos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Triterpenos/química , Triterpenos/aislamiento & purificación
16.
Chem Biodivers ; 18(7): e2100335, 2021 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-34089236

RESUMEN

Ardisia crenata Sims (Primulaceae) occurs in natural habitats in two varieties, bearing red or white fruits. While roots of the red-berried ardisia are valued as a medicinal product, the pharmacological activity of which is attributed to triterpene saponins, including ardisiacrispin A, data on the white-berried variety are scarce. A TLC-densitometric method was developed and validated to estimate the levels of saponins, calculated as ardisiacrispin A, in different plant parts in both varieties. Their content amounted to 22.17±4.75 and 25.72±1.46 mg/g d.w. in roots, and 2.64±0.74 and 3.43±0.70 mg/g d.w. in fruits of red-berried and white-berried ardisia, respectively. Assessment of cytotoxicity of ardisiacrispin A and A. crenata extracts on a panel of human cancer cell lines revealed a similar effect of root extracts from both varieties, with the highest potency against melanoma WM793 and colon cancer Caco2. Thus, roots of the white-berried variety may be treated as a substitute for red-berried ardisia and serve as an alternative source for the acquisition of plant material rich in bioactive saponins.


Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Ardisia/química , Ácido Oleanólico/análogos & derivados , Extractos Vegetales/farmacología , Saponinas/farmacología , Antineoplásicos Fitogénicos/análisis , Línea Celular , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Ácido Oleanólico/análisis , Ácido Oleanólico/farmacología , Extractos Vegetales/análisis , Raíces de Plantas/química , Saponinas/análisis
17.
Molecules ; 26(16)2021 Aug 13.
Artículo en Inglés | MEDLINE | ID: mdl-34443502

RESUMEN

Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Their effect was dose and time-dependent with varied potency, the highest against prostate PC3 and melanoma WM793, where IC50 was lower than the reference drug doxorubicin. Structure-activity relationship is briefly discussed.


Asunto(s)
Chenopodiaceae/química , Glicósidos/farmacología , Triterpenos/farmacología , Espectroscopía de Resonancia Magnética con Carbono-13 , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , Glicósidos/química , Glicósidos/aislamiento & purificación , Humanos , Espectroscopía de Protones por Resonancia Magnética , Triterpenos/química , Triterpenos/aislamiento & purificación
18.
Molecules ; 26(8)2021 Apr 09.
Artículo en Inglés | MEDLINE | ID: mdl-33918584

RESUMEN

Dragon fruits are a valued source of bioactive compounds with high potential to become a functional food. The aim of the study was to evaluate and compare the chemopreventive potential and chemical composition of fruits harvested in Thailand and Israel. The amount of different compounds in water and methanol extracts and antioxidant activity was investigated. Moreover, cytotoxic activity against cancer and normal cells of skin, prostate, and gastrointestinal origin was performed, accompanied by anti-inflammatory assay based on NO production in RAW 264.7 macrophage model. Additionally, the quenching properties of polyphenols from fruits were determined by the interaction of the main drug carrier in blood human serum (HSA). The chemometric analysis was used to reveal the relationships between the determined parameters. Dragon fruits harvested in Israel revealed higher antioxidant properties and total content of polyphenols and betacyanins when compared to those from Thailand. The examined fruits of both origins showed significant cytotoxic activity toward colon and prostate cancer cells, with no toxic effect on normal cells, but also no anti-inflammatory effect. Moreover, a high binding ability to HSA was observed for water extracts of dragon fruits. All these predestine dragon fruits are the candidates for the attractive and chemopreventive elements of daily diet.


Asunto(s)
Cactaceae/química , Quimioprevención , Frutas/química , Polifenoles/análisis , Antioxidantes/farmacología , Proteínas Sanguíneas/metabolismo , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , Fluorescencia , Humanos , Israel , Análisis de los Mínimos Cuadrados , Óxido Nítrico/metabolismo , Tailandia
19.
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
20.
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
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