Search Results (28)

Phytoestrogens are components naturally occurring in plants and include many foods that are part of the regular diet of animals and humans. Phytoestrogens are xenoestrogens of plant origin that are not produced in the endocrine system. Phytoestrogens can act as either agonists or antagonists, depending on their tissue concentrations and the levels of endogenous estrogens at various life stages. The aim was to evaluate the intake of phytoestrogens and the estrogenic effect of the diet of women at university in Chihuahua (Mexico). In total, 400 female university students individually filled out a food frequency questionnaire (FFQ) that included 120 foods. Estimates of the intake of phytoestrogen (genistein, daidzein, biochanin A, formononetin, matairesinol, coumestrol, enterolactone, secoisoresinol, enterodiol) in the subjects’ daily diet were based on published reports. Quantification of phytoestrogens was expressed in µg day⁻¹. The estrogenic effect of those compound identified according to the foods consumed was estimated using the in vitro E-SCREN test. SPSS v.22.0 (IBM, Chicago, IL, USA) was applied for statistical analysis following descriptive analysis and stepwise regression. p < 0.050 was taken as significant. The results of intake show that the majority of isoflavones are formononetin (median 110.60 (μg day⁻¹) and their estrogenic activity is 4.11 Eq. E2 (pmol day⁻¹); the majority of lignans are enterolactone (median 147.24 (μg day⁻¹), and their estrogenic activity is 4.94 Eq. E2 (pmol day⁻¹). The total phytoestrogen estrogenic effect is measured in pM of E2, with a mean of 28.28 (SD = 23.97) and median of 21.50. The mean consumption of phytoestrogens in Mexican university students is similar to the consumption found in similar studies in the United States, England, Germany, and Spain (<1 mg day⁻¹). Phytoestrogens can be beneficial in adult women during perimenopause and menopause due to their estrogenic effects, but they are less recommended for women in the fertile stage, as, for example, in the study presented here, because they could function as endocrine disruptors. They are not recommended as dietary supplements for young women or pregnant women. Full article

The fruit of Forsythia suspensa (Thunb.) Vahl has been used in traditional Chinese medicine as “Forsythiae fructus”. The species is also grown in parks and gardens, and on streets and building lots, as an ornamental plant, but it requires pruning. In this study, the allelopathic activity and allelopathic substances in the leaves of pruned branches of F. suspensa were investigated to determine any potential application. The leaf extracts of F. suspensa showed growth inhibitory activity against three weed species; Echinochloa crus-galli, Lolium multiflorum, and Vulpia myuros. Two allelopathic substances in the extracts were isolated through the bioassay-guided purification process, and identified as (-)-matairesinol and (-)-arctigenin. (-)-Matairesinol and (-)-arctigenin, which showed significant growth inhibitory activity at concentrations greater than 0.3 mM in vitro. The inhibitory activity of (-)-arctigenin was greater than that of (-)-matairesinol. However, both compounds were more active than (+)-pinolesinol which is their precursor in the biosynthetic pathway. The investigation suggests that F. suspensa leaves are allelopathic, and (-)-matairesinol and (-)-arctigenin may contribute to the growth inhibitory activities. Therefore, the leaves of the pruned branches can be applied as a weed management strategy in some agricultural practices such as using the leaf extracts in a foliar spray and the leaves in a soil mixture, thereby reducing the dependency on synthetic herbicides in the crop cultivation and contributing to developing eco-friendly agriculture. Full article

Type 2 diabetes (T2D) is a growing health concern with an estimated 462 million people having been diagnosed worldwide. T2D is characterized by chronically elevated blood glucose and insulin resistance, which culminate in a diminished function of the β-cell mass in its later stages. This can be perpetuated by and result in inflammation, excess reactive oxygen species production, obesity, and the dysregulation of multiple cellular pathways. Many naturally occurring small molecules have been investigated in terms of their roles in modulating glucose homeostasis and β-cell function. Many of these compounds can be found in commonly used sources of food and drink. Interestingly, a correlation has been observed between coffee consumption and T2D incidence. However, the specific compounds responsible for this correlation and their mechanisms are still somewhat undetermined. This paper reviews recent research findings on the effects of several polyphenols that are either found in coffee or are metabolites of compounds found in coffee (enterodiol, enterolactone, matairesinol, secoisolariciresinol, kaempferol, quercetin, and chlorogenic acid) on glucose homeostasis and health complications associated with glucose dysregulation, with a special emphasis on their potential anti-diabetic effects. The factors that affect polyphenol content in coffee are also addressed. Full article

Lignans constitute a large group of phenolic plant secondary metabolites possessing high bioactivity. Their accurate determination in plant extracts with a complex chemical composition is challenging and requires advanced separation techniques. In the present study, a new approach to the determination of lignans in coniferous knotwood extracts as the promising industrial-scale source of such compounds based on comprehensive two-dimensional liquid chromatography separation and UV spectrophotometric detection is proposed. First and second-dimension column screening showed that the best results can be obtained using a combination of non-polar and polar hydroxy group embedded octadecyl stationary phases with moderate (~40%) “orthogonality”. The optimization of LC × LC separation conditions allowed for the development of a new method for the quantification of the five lignans (secoisolariciresinol, matairesinol, pinoresinol, 7-hydroxymatairesinol, and nortrachelogenin) in knotwood extracts with limits of quantification in the range of 0.27–0.95 mg L⁻¹ and a linear concentration range covering at least two orders of magnitude. Testing the developed method on coniferous (larch, fir, spruce, and pine) knotwood extracts demonstrated the high selectivity of the analysis and the advantages of LC × LC in the separation and accurate quantification of the compounds co-eluting in one-dimensional HPLC. Full article

The history of the use of natural compounds as therapeutic agents goes back many centuries. Being the first objects of interest in the early days of medicine, natural compounds are still of great relevance, considering the improvement of methods for isolation, chemical transformation, and synthesis. They are also used in oncology, with the advantage of preventing the development of toxicity to normal cells and resistance in tumor cells. One of the promising classes of natural compounds with antitumor activity is lignans. We studied a number of lignans (arctiin, honokiol, matairesinol, pinoresinol, myrislignan, enterodiol, and enterolactone) in the breast cancer cell line MCF7 and the subline MCF7/FUL with acquired resistance to the antiestrogen fulvestrant. Antiproliferative activity was assessed using the MTT test. An analysis of the level of intracellular proteins was carried out via immunoblotting. Based on the results of the screening, the most active compound was honokiol; it had the lowest IC₅₀ value for both MCF7 and MCF7/FUL cells, 19.7 μM and 9.1 μM, respectively. The revealed antiproliferative activity of honokiol against resistant cells prompted us to study its effects on intracellular proteins associated with proliferation and cell death. Honokiol suppressed the expression of Bcl-2 (an inhibitor of apoptosis) and cyclin D1 (a cell cycle regulator) in both cell lines, but this effect was more pronounced in the resistant subline. The decrease in the expression of antiapoptotic and proliferative proteins induced by honokiol is consistent with its antiproliferative effect, which is more pronounced in resistant subline MCF7/FUL. Full article

Germination is a simple process that improves the nutritional and medicinal values of seeds such as chickpeas. However, the detailed analysis of the phytochemical profile after chemical elicitation during chickpea germination is indispensable when making inferences about its biological properties. Therefore, an evaluation was made of the effect of the chemical inducers salicylic acid (SA, 1 and 2 mM), chitosan (CH, 3.3 and 7 μM), and hydrogen peroxide (H₂O₂, 20 and 30 mM) during germination at 25 °C with 70% RH for 4 days on the content of antinutritional and bioactive compounds, including phenolics, sterols, and saponins, in three Mexican chickpea varieties (Blanoro, Patron, and San Antonio) using UPLC-ELSD-ESI-QqQ-MS/MS, UPLC-DAD-ESI-QqQ-MS/MS, and HPLC-DAD-sQ-MS. The highest increase in phenolics and saponins was found in the Blanoro sprouts induced with SA 2 mM, whereas the highest phytosterol content was detected in San Antonio sprouts induced with CH 7 μM. In addition, significant increases in mono-, di-, and oligosaccharides and decreases in antinutritional contents were achieved after germination with most of the elicitation conditions. More importantly, we identified new compounds in chickpea sprouts, such as the lignans matairesinol and secoisolariciresinol, the phenolic compounds epicatechin gallate and methyl gallate, some phytosterols, and the saponin phaseoside 1, which further increased after chemical elicitation. Full article

Lignans are widespread polyphenolic secondary plant metabolites possessing high biological activity. One of the most promising industrial-scale sources of such compounds is coniferous knotwood, containing a large number of polyphenolic compounds. Their use in pharmaceutical and other industries is limited by the difficulty in obtaining high-purity preparations from plant material and the requirement of advanced separation techniques. In this study, supercritical fluid chromatography on polar stationary phases was proposed for the efficient separation and identification of spruce, pine, fir, and larch knotwood extractives. Among the six tested sorbents, the best results were shown by silica with grafted diol and 2-ethylpyridine groups under conditions of gradient elution with a carbon dioxide–methanol mobile phase, which ensured the efficient retention and separation of analytes due to donor–acceptor interactions. Scaling up the method on a DIOL stationary phase provided a semi-preparative separation of extractives within 30 min to obtain 14 individual compounds with a purity of 90–99% and yields from 0.3 to 51% of the dry extract. These included eight lignans (nortrachelogenin, matairesinol, oxomatairesinol, α-conidendrin, 5-hydroxymatairesinol and its isomer, lariciresinol, and secoisolariciresinol), two oligolignans, three stilbenes (pinosylvin and its methyl ester, pterostilbene), and flavonoid taxifolin. The developed approach is distinguished with low operational costs, low consumption of organic solvents, environmental safety, and it is fully consistent with the principles of green chemistry. Full article

Abies alba Mill. (Pinaceae), silver fir, is a widespread gymnosperm species in Europe, important for its ecological, economic, social, and cultural significance, as well as for its use for food and bioremediation purposes. The various parts of the plant (leaves, branches, cones, wood, bark) are also of pharmaceutical interest due to their composition of active compounds. In the last three decades, an impressive amount of research has been dedicated to this species. The variability of the chemical composition of essential oils (whether they come from leaves, oleoresin from branches, or other parts of the plant) is impressive, even in the case of specimens collected from the same geographical area. For essential oils prepared from needles or twigs and branches, limonene, β-pinene, α-pinene, camphene, β-phellandrene, and bornyl acetate are the leading compounds, although their wide variations seem to correspond to multiple chemotypes. Both bark and wood are rich in lignans and phenolic compounds. Matairesinol is apparently the dominant lignan in bark, and secoisolariciresinol and lariciresinol are the dominant ones in wood samples. Pharmacological studies with promising results have evaluated the antioxidant effect (mainly due to essential oils), but also the antimicrobial, antitumor, probiotic, antidiabetic, anti-steatosis, and anti-psoriatic activities. Full article

Neuroblastoma can be accessed with compounds of larger sizes and wider polarities, which do not usually cross the blood–brain barrier. Clinical data indicate cases of spontaneous regression of neuroblastoma, suggesting a reversible point in the course of cell brain tumorigenesis. Dual specificity tyrosine-phosphorylation-regulated kinase2 (DYRK2) is a major molecular target in tumorigenesis, while curcumin was revealed to be a strong inhibitor of DYRK2 (PBD ID: 5ZTN). Methods: in silico studies by CLC Drug Discovery Workbench (CLC) and Molegro Virtual Docker (MVD) Software on 20 vegetal compounds from the human diet tested on 5ZTN against the native ligand curcumin, in comparison with anemonin. In vitro studies were conducted on two ethanolic extracts from Anemone nemorosa tested on normal and tumor human brain cell lines NHA and U87, compared with four phenolic acids (caffeic, ferulic, gentisic, and para-aminobenzoic/PABA). Conclusions: in silico studies revealed five dietary compounds (verbascoside, lariciresinol, pinoresinol, medioresinol, matairesinol) acting as stronger inhibitors of 5ZTN compared to the native ligand curcumin. In vitro studies indicated that caffeic acid has certain anti-proliferative effects on U87 and small benefits on NHA viability. A. nemorosa extracts indicated potential benefits on NHA viability, and likely dangerous effects on U87. Full article

Since chronic inflammation can be seen in severe, long-lasting diseases such as cancer, there is a high demand for effective methods to modulate inflammatory responses. Among many therapeutic candidates, lignans, absorbed from various plant sources, represent a type of phytoestrogen classified into secoisolariciresionol (Seco), pinoresinol (Pino), matairesinol (Mat), medioresinol (Med), sesamin (Ses), syringaresinol (Syr), and lariciresinol (Lari). Lignans consumed by humans can be further modified into END or ENL by the activities of gut microbiota. Lignans are known to exert antioxidant and anti-inflammatory activities, together with activity in estrogen receptor-dependent pathways. Lignans may have therapeutic potential for postmenopausal symptoms, including cardiovascular disease, osteoporosis, and psychological disorders. Moreover, the antitumor efficacy of lignans has been demonstrated in various cancer cell lines, including hormone-dependent breast cancer and prostate cancer, as well as colorectal cancer. Interestingly, the molecular mechanisms of lignans in these diseases involve the inhibition of inflammatory signals, including the nuclear factor (NF)-κB pathway. Therefore, we summarize the recent in vitro and in vivo studies evaluating the biological effects of various lignans, focusing on their values as effective anti-inflammatory agents. Full article

Lignans are a group of natural polyphenols present in medicinal plants and in plants which are a part of the human diet for which more and more pharmacological activities, such as antimicrobial, anti-inflammatory, hypoglycemic, and cytoprotective, are being reported. However, it is their cytotoxic activities that are best understood and which have shed light on this group. Two anticancer drugs, etoposide, and teniposide, were derived from a potent cytotoxic agent—podophyllotoxin from the roots of Podophyllum peltatum. The evidence from clinical and observational studies suggests that human microbiota metabolites (enterolactone, enterodiol) of dietary lignans (secoisolariciresinol, pinoresinol, lariciresinol, matairesinol, syringaresinol, medioresinol, and sesamin) are associated with a reduced risk of some hormone-dependent cancers. The biological in vitro, pharmacological in vivo investigations, and clinical studies demand significant amounts of pure compounds, as well as the use of well-defined and standardized extracts. That is why proper extract preparation, optimization of lignan extraction, and identification are crucial steps in the development of lignan use in medicine. This review focuses on lignan extraction, purification, fractionation, separation, and isolation methods, as well as on chromatographic, spectrometric, and spectroscopic techniques for their qualitative and quantitative analysis. Full article

Pancreatic ductal adenocarcinoma (PDAC) is one of the most aggressive types of cancer and exhibits a devastating 5-year survival rate. The most recent procedure for the treatment of PDAC is a combination of several conventional chemotherapeutic agents, termed FOLFIRINOX, that includes irinotecan, leucovorin, oxaliplatin, and 5-fluorouracil (5-FU). However, ongoing treatment using these agents is challenging due to their severe side effects and limitations on the range of patients available for PDAC. Therefore, safer and more innovative anticancer agents must be developed. The anticarcinoma activity of matairesinol that can be extracted from seagrass has been reported in various types of cancer, including prostate, breast, cervical, and pancreatic cancer. However, the molecular mechanism of effective anticancer activity of matairesinol against pancreatic cancer remains unclear. In the present study, we confirmed the inhibition of cell proliferation and progression induced by matairesinol in representative human pancreatic cancer cell lines (MIA PaCa-2 and PANC-1). Additionally, matairesinol triggers apoptosis and causes mitochondrial impairment as evidenced by the depolarization of the mitochondrial membrane, disruption of calcium, and suppression of cell migration and related intracellular signaling pathways. Finally, matairesinol exerts a synergistic effect with 5-FU, a standard anticancer agent for PDAC. These results demonstrate the therapeutic potential of matairesinol in the treatment of PDAC. Full article

Lignans, a group of polyphenols, have been identified in eight cold pressed oils from fruits, nuts, and seeds, retrieved from the Brazilian market. The oils under investigation were avocado, Brazilian nut, canola, coconut, grapeseed, macadamia, palm, and pequi. Olive oil was selected as a reference oil, since numerous data on its lignan content are available in literature. The qualitative and quantitative profiles were obtained, after extraction, by means of UFLC-ESI-MS/MS analyses. The total lignan content showed a high variability, ranging from 0.69 mg·Kg⁻¹ (pequi) to 7.12 mg·Kg⁻¹ (grapeseed), with the highest content registered for olive oil. Seven lignans were quantified, matairesinol and pinoresinol being the most abundant. The LC-MS/MS method was validated, showing linearity in the range of 12.5–212.5 mg·Kg⁻¹, LOD in the range of 0.18–11.37 mg·Kg⁻¹, and LOQ in the range of 0.53–34.45 mg·Kg⁻¹. Additionally, part of the study was focused on the evaluation of the flavor profile, this being a key element in consumers’ evaluations, by means of HS-SPME-GC. In total, 150 volatile compounds were determined in the eight oils, with identified fractions ranging from 91.85% (avocado) to 96.31% (canola), with an average value of 94.1%. Groups of components contributed characteristically to the flavour of each oil. Full article

Based on molecular docking studies on the ERα, a series of lignan derivatives (3–16) were designed and semisynthesized from the natural dibenzylbutyrolactones bursehernin (1) and matairesinol dimethyl ether (2). To examine their estrogenic and antiestrogenic potencies, the effects of these compounds on estrogen receptor element (ERE)-driven reporter gene expression and viability in human ER+ breast cancer cells were evaluated. Lignan compounds induced ERE-driven reporter gene expression with very low potency as compared with the pure agonist E2. However, coincubation of 5 μM of lignan derivatives 1, 3, 4, 7, 8, 9, 11, 13, and 14 with increasing concentrations of E2 (from 0.01 pM to 1 nM) reduced both the potency and efficacy of pure agonists. The binding to the rhERα-LBD was validated by TR-FRET competitive binding assay and lignans bound to the rhERα with IC₅₀ values from 0.16 μM (compound 14) to 6 μM (compound 4). Induced fit docking (IFD) and molecular dynamics (MD) simulations for compound 14 were carried out to further investigate the binding mode interactions. Finally, the in silico ADME predictions indicated that the most potent lignan derivatives exhibited good drug-likeness. Full article

The study aims to examine the association of dietary intake of lignans with the risk of hip fractures in Chinese older adults. This was a 1:1 age- and gender- matched case–control study. Dietary survey was conducted by face-to-face interviews using a 79-item validated food frequency questionnaire. Habitual intake of total and individual lignans (matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol) was estimated based on the available lignans databases. Conditional logistic regression was used to examine the relationship of dietary total and individual lignans, lignan-rich foods (vegetables, fruits, nuts, and cereals) and dietary fibers with the risk of hip fracture. A total of 1070 pairs of hip fracture incident cases and controls were recruited. Compared with the lowest quartile, the highest quartile group showed a reduced hip fracture risk by 76.3% (0.237, 95% CI: 0.103–0.544, P_trend < 0.001) for total lignans, and 62.5% (0.375, 95% CI: 0.194–0.724, P_trend = 0.001) for dietary fibers. Similar findings were observed for individual lignans, the estimated enterolactone level, as well as lignans from vegetables and nuts. We concluded that greater consumption of total and individual lignans, and lignan-rich foods were significantly associated with decreased risk of hip fracture. Full article