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Silybum marianum (L.) Gaertn. (Asteraceae) was hydroponically cultured using a nutrient film technique system. Silibinin, isosilibinin and silychristin were detected in the fruits of the cultured plants. The effect of salicylic acid on the improvement of flavonolignans production by the fruits of the hydroponically cultured S. marianum was investigated. Salicylic acid was added to the nutrient solution at different concentrations (100, 200 and 400 µM) and the mature fruits of the plant were collected five days after elicitor addition. The fruits were then analyzed for their total flavonolignans contents and individual components using quantitative proton nuclear magnetic resonance spectroscopy (qHNMR) and high-performance liquid chromatography (HPLC). The results showed that elicitation with salicylic acid at 200 µM for five days increased production of total flavonolignans (1.7-fold by qHNMR and 1.6-fold by HPLC) higher than the control cultures and (1.4-fold by qHNMR and 1.1-fold by HPLC) higher than the cultivated plants. Silychristin was the major flavonolignan produced by the cultured plant. Elicitation by 200 µM salicylic acid increased silychristin production (1.6-fold by qHNMR and HPLC) higher than the control cultures and (1.3-fold by qHNMR and 1.0-fold by HPLC) higher than the cultivated plants. The present study provides a chance to improve secondary metabolite yield, serves as a useful tool for studying the biosynthesis of these medicinally valuable compounds and its regulation in plant and spots more light on hydroponic system as an important agricultural technique. [ABSTRACT FROM AUTHOR]

Background: In recent years the number of natural products used as pharmaceuticals, components of dietary supplements and cosmetics has increased tremendously requiring more extensive evaluation of their pharmacokinetic properties.Purpose: This study aims at combining in vitro and in silico methods to evaluate the gastrointestinal absorption (GIA) of natural flavonolignans from milk thistle (Silybum marianum (L.) Gaertn.) and their derivatives.Methods: A parallel artificial membrane permeability assay (PAMPA) was used to evaluate the transcellular permeability of the plant main components. A dataset of 269 compounds with measured PAMPA values and specialized software tools for calculating molecular descriptors were utilized to develop a quantitative structure-activity relationship (QSAR) model to predict PAMPA permeability.Results: The PAMPA permeabilities of 7 compounds constituting the main components of the milk thistle were measured and their GIA was evaluated. A freely-available and easy to use QSAR model predicting PAMPA permeability from calculated physico-chemical molecular descriptors was derived and validated on an external dataset of 783 compounds with known GIA. The predicted permeability values correlated well with obtained in vitro results. The QSAR model was further applied to predict the GIA of 31 experimentally untested flavonolignans.Conclusions: According to both in vitro and in silico results most flavonolignans are highly permeable in the gastrointestinal tract, which is a prerequisite for sufficient bioavailability and use as lead structures in drug development. The combined in vitro/in silico approach can be used for the preliminary evaluation of GIA and to guide further laboratory experiments on pharmacokinetic characterization of bioactive compounds, including natural products. [ABSTRACT FROM AUTHOR]

Supercritical fluid extraction with carbon dioxide is nowadays one of the best approaches on an economic and ecological point of view for the extraction of natural compounds from plants. Besides, many seeds or fruits contain both lipids, as triglycerides, which can be used for food or cosmetic industries, and polyphenols which do have many bioprotective effects for the human health. By using successively pure carbon dioxide and carbon dioxide added with a polar modifier, either pure ethanol or a ethanol/water mixture, we achieved first the extraction of triglycerides of the milk thistle seeds, followed by the extraction of the flavonolignans, which are bioactive compounds. Effects of pressure (15 and 25 MPa) and temperature (40 and 60 °C) were studied on the lipids extraction efficiency. For flavonolignans, the polar compounds, the impact of modifier amount (pure ethanol from 10% to 40%) and water percentage in ethanol (5–15%) were compared. The duration of the two sequential steps to achieve the complete seed defatting and to increase the flavonolignan recovery were also studied. The complete lipids extraction was achieved with pure CO2 at 40 °C, 25 MPa for 30 min whereas the extraction of flavonolignans was achieved with 20% of modifier (wate/ethanol 15/85) during 90 min. The analysis of the triglyceride composition of milk thistle seed were studied by using supercritical fluid chromatography (SFC), whereas the analysis of flavonolignans was carried out by an improved Ultra-high-pressure liquid chromatography (UHPLC) method. [Display omitted] • Selective sequential supercritical fluid extraction applied on Milk Thistle seeds. • Supercritical fluid chromatography for the TG analysis of Milk Thistle. • Study of the defatting and the supercritical extraction of flavonolignans. [ABSTRACT FROM AUTHOR]

• Two new flavonolignans were isolated from Cecropia obtusifolia. • Chemical structures were established on the basis of spectroscopic methods. • Ent-mururin A and ent-vaccinin A showed moderate in vitro antiplasmodial activity. • Scientific support for the use of Cecropia species against malaria is provided. Cecropia species are traditionally used in several Latin American countries to treat various diseases including malaria. A phytochemical investigation on the leaves of Cecropia obtusifolia Bertol (Urticaceae) afforded two new flavonolignans, i.e. ent-mururin A (1) and ent-vaccinin A (2). They were isolated by means of chromatographic techniques and elucidated based on their spectroscopic (NMR, MS and optical rotation) data, and were described as new isomers of mururin A and vaccinin A. Antiplasmodial evaluation revealed that 1 and 2 were moderately active in vitro against the chloroquine-resistant strain Plasmodium falciparum K1 (IC 50 4.68 μM and 7.34 μM, respectively) without cytotoxic effects up to a concentration of 64.0 μM. [ABSTRACT FROM AUTHOR]

[Display omitted] • Silymarin metabolism was studied in 33 volunteers taking 2 × 200 mg/day for 90 days. • Metabolic profiles of flavonolignans and taxifolin were analyzed using UHPLC-MS. • Inter-individual differences in metabolite levels in urine and feces were noted. • Relation between metabolism, age, BMI, smoking, or gut microbiota was evaluated. This study examined the metabolism of flavonolignans and taxifolin in 33 healthy adult male volunteers, who received 200 mg of silymarin orally twice daily for three months. First-morning urine and feces collected on days 10 and 90 were analyzed by UHPLC-MS and bacterial composition of feces was investigated by Next Generation Sequencing. The analyses revealed 5/4 types of flavonolignan/taxifolin metabolites in urine and 13/10 types of metabolites in feces, with large differences in total metabolite levels in both urine and feces observed among individual participants. In urine, 21 and 23 participants showed some increase in the total amount of flavonolignan and taxifolin metabolites, respectively, on day 90 compared with day 10. In feces, some correlation was found between the amount of metabolites and the composition of the intestinal microbiota. In conclusion, silymarin flavonolignans and taxifolin undergo multiple biotransformation reactions, and the metabolic profiles of the constituents considerably vary among individuals. [ABSTRACT FROM AUTHOR]