Fruits Of Silybum Marianum Research Articles

Microbial transformation of silybin by Trichoderma koningii

Microbial transformation of silybin A ( 1) and silybin B ( 2), the major hepatoprotective flavonolignan diastereomers from the fruits of Silybum marianum, with the culture broth of Trichoderma koningii gave two pairs of glucosylated derivatives. Their structures were identified as silybin A 3- O-β- d-glucopyranoside ( 3), silybin A 7- O-β- d-glucopyranoside ( 4), silybin B 3- O-β- d-glucopyranoside ( 5) and silybin B 7- O-β- d-glucopyranoside ( 6) by spectroscopic methods.

Yeast extract and methyl jasmonate-induced silymarin production in cell cultures of Silybum marianum (L.) Gaertn

The biosynthesis of the flavonolignan silymarin, a constitutive compound of the fruits of Silybum marianum with strong antihepatotoxic and hepatoprotective activities, is severely reduced in cell cultures of this species. It is well known that elicitation is one of the strategies employed to increase accumulation of secondary metabolites. Our study here reports on the effect of several compounds on the production of silymarin in S. marianum cultures. Yeast extract (YE), chitin and chitosan were compared with respect to their effects on silymarin accumulation in S. marianum suspensions and only yeast extract stimulated production. Jasmonic acid (JA) potentiated the yeast extract effect. One of the jasmonic acid derivatives, methyl jasmonate (MeJA), strongly promoted the accumulation of silymarin. Methyl jasmonate acted in a number of steps of the metabolic pathway of flavonolignans and its stimulating effect was totally dependent of “de novo” protein synthesis. Chalcone synthase (CHS) activity was enhanced by methyl jasmonate; however there did not appear to be a temporal relationship between silymarin accumulation and increase in enzyme activity. Also, this increase was not blocked by the protein synthesis inhibitor cycloheximide (CH). This study indicates that elicitor treatment promotes secondary metabolite production in S. marianum cultures and that jasmonic acid and its functional analogue plays a critical role in elicitation.

Silibinin down-regulates prostate epithelium-derived Ets transcription factor in LNCaP prostate cancer cells.

The androgen-sensitive human prostate cancer cell line LNCaP expresses the estrogen receptor beta and androgen receptor and can be stimulated by androgens to secrete prostate-specific antigen (PSA). In this study we demonstrate the cancer protective potential of silibinin, a flavolignan derived from the fruits of Silybum marianum, which down-regulates the co-activator of the androgen receptor, the prostate epithelium-derived Ets transcription factor (PDEF) and consequently the secretion of PSA. LNCaP cells were treated with various concentrations of silibinin in the presence or in the absence of 5alpha-dihydrotestosterone (DHT). We used real-time RT-PCR to quantify mRNA expression of PDEF and PSA with gene-specific dual-labelled fluorescence probes. PSA secretion from LNCaP cells in conditioned media was measured with the Elecsys System 2010. Silibinin down-regulated PSA mRNA expression and PSA secretion in conditioned medium under basal and DHT (10(-8) M) stimulated conditions, which was paralleled by PDEF down-regulation. DHT alone stimulated PDEF and PSA gene expression and PSA secretion. The down-regulation of basal as well as DHT stimulated PDEF and PSA by silibinin demonstrates the antiproliferative potential of this agent. These effects underline the possible therapeutic use of silibinin in the management of prostate cancer.

Silibinin protects mice from T cell-dependent liver injury ☆

Background/Aims: Silibinin is the major pharmacologically active compound of the Silybum marianum fruit extract silymarin. Its well-known hepatoprotective activities are mostly explained by antioxidative properties, inhibition of phosphatidylcholine synthesis or stimulation of hepatic RNA and protein synthesis. Here, we characterized the hepatoprotective potential of silibinin as an immune-response modifier in T cell-dependent hepatitis in vivo. Methods: Silibinin was tested in the mouse model of concanavalin A (ConA)-induced, T cell-dependent hepatitis. Liver injury was assessed by quantification of plasma transaminase activities and intrahepatic DNA fragmentation. Plasma cytokine concentrations were determined by enzyme-linked immunosorbent assay (ELISA), intrahepatic cytokine and inducible NO synthase (iNOS) mRNA levels by reverse transcriptase polymerase chain reaction, intrahepatic iNOS expression by immunofluorescent staining, and intrahepatic nuclear factor kappa B (NF-κB) activation by electrophoretic mobility shift assay. Results: Silibinin significantly inhibited ConA-induced liver disease. Silibinin proved to be an immune-response modifier in vivo, inhibiting intrahepatic expression of tumor necrosis factor, interferon-γ, interleukin (IL)-4, IL-2, and iNOS, and augmenting synthesis of IL-10. In addition, silibinin inhibited intrahepatic activation of NF-κB. Conclusions: Silibinin, suppressing T cell-dependent liver injury as an immune-response modifier, might be a valuable drug in therapeutic situations in which intrahepatic immunosuppression is required.

Analysis of the active components of silymarin

Silymarin is an antihepatotoxic substance isolated from fruits of Silybum marianum. Possibly due to their antioxidant and membrane stabilizing properties, the compounds have been shown to protect different organs and cells against a number of insults. The content and composition of main silymarin components (silybin, isosilybin, silydianin and silychristin) in various pharmaceuticals were analysed using HPLC and newly developed capillary zone electrophoresis method. Antioxidant properties expressed as total antioxidant status (TAS) of silymarin components were studied. Results of TAS were correlated with electropherograms and chromatograms.

Predictors for cardiovascular events, in subjects with familial hypercholesterolemia: 15 years follow up (1987–2002)

Silymarin, a mixture of flavonolignans, comprised mainly of three isomers, silybin, silydianin and silychristin isolated from the fruits of Silybum marianum, is currently in therapeutic use as a hepatoprotective agent. Silymarin on evaluation exhibited significant antiinflammatory and antiarthritic activities in the papaya latex induced model of inflammation and mycobacterial adjuvant induced arthritis in rats. Results of the study indicate its action through inhibition of 5-lipoxygenase for antiinflammatory and antiarthritic activities.

PREPARATIVE SEPARATION OF FRUIT EXTRACT OF SILYBUM MARIANUM USING A HIGH-SPEED COUNTERCURRENT CHROMATOGRAPH WITH SCALE-UP COLUMNS

ABSTRACT A crude extract (12 g) of fruits of Silybum marianum was separated with a two-phase solvent system composed of water/ methanol/ethyl acetate/n-hexane (4 : 3 : 4 : 1, v/v/v/v) by high speed countercurrent chromatography. Using a set of three large multilayer coil separation columns with a total capacity of 2460 mL, the separation yielded 1.37 g of silycristin at 93.1% purity, 3.47 g of silybin at 95.7% purity, and 0.93 g of isosilybin at 89.7% purity.

Analysis of Flavonoids in Silybum marianum Fruit by HPLC

Flavonoids of spotted milkweed (Silybum marianumL. Gaerth.) were optimally separated using reverse-phase HPLC with isocratic elution by CH 3 CN-H 2 O over Separon SGX C 18 . The flavolignans silybin, silydianin, silychristin, and the flavonoid taxifolin were identified in the chromatograms of extracts from this plant

Dissolution Test for Silymarin Tablets and Capsules

Silybine (SBN), isosilybine (ISBN), silycristine (SCN), silydianine (SDN), and taxifoline (TXF) are the main active flavonoids commonly found in the dried fruits of Silybum marianum, Gaertner (Compositae). Concentrations of these compounds, except TXF, are usually expressed together as silymarin content. This paper describes a simple dissolution test developed to estimate silymarin (Sl) in pharmaceutical formulations. Five commercial products were tested using this new method (including tablets, sugar tablets, and capsules): two from Argentina, one from Brazil, one from Spain, and one from Italy. Results demonstrated that, provided the dosage form disintegrates, amounts dissolved range from 50 to 90% of the labeled value. Products were analyzed by high performance liquid chromatography (HPLC) and UV spectrophotometry.

Anti-inflammatory and anti-arthritic activities of silymarin acting through inhibition of 5-lipoxygenase.

Silymarin, a mixture of flavonolignans, comprised mainly of three isomers, silybin, silydianin and silychristin isolated from the fruits of Silybum marianum, is currently in therapeutic use as a hepatoprotective agent. Silymarin on evaluation exhibited significant antiinflammatory and antiarthritic activities in the papaya latex induced model of inflammation and mycobacterial adjuvant induced arthritis in rats. Results of the study indicate its action through inhibition of 5-lipoxygenase for antiinflammatory and antiarthritic activities.

Determination of silymarine in the extract from the dried silybum marianum fruits by high performance liquid chromatography and capillary electrophoresis

Silybine (SBN), isosilybine (ISBN), silycristine (SCN), silydianine (SDN), and taxifoline (TXF) are the main active flavanoids, generally found in the dried fruits of silybum marianum. The concentrations of these compounds, excepted TXF, are all together usually expressed as silymarine content. In this paper the determination of the silymarine titre was made by high performance liquid chromatography (HPLC), and high performance capillary electrophoresis (HPCE). Two reversed stationary phases, RP-18 and RP-8, were observed comparing the resolutions of all considered flavanoids with each stationary phases. The HPCE was carried out considering the possible improvement in the resolution of SBN, CN, SDN and TXF using,8-cyclodextrines or organic modifier. The qualitative and quantitative data obtained by HPLC and HPCE were compared.

Evaluation of the silymarin content in Silybum marianum (L.) Gaertn. Cultivated under different agricultural conditions

AbstractAn HPLC assay for the determination of silymarin in the fruits of Silybum marianum is given. The effect of different water regimes and nitrogen fertilization levels on the silymarin content of cultivated plants grown in reclaimed desert land have been studied. The highest silymarin contents were obtained upon nitrogen fertilization with 100, 150 kg/feddan (1 feddan = 4200 m2) and a 60% water regime without fertilization compared to the content of silymarin in wild plants.

Effect of the flavanolignans of Silybum marianum L. On lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes

The effect of several flavanolignans (silicristin, silidianin, silybin and isosilybin) present in silymarin, the extract of Silybum marianum fruits, was tested on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes. In microsomes lipid peroxidation was generated by ADP/Fe 2+ and NADPH. All flavanolignans inhibited peroxidation in a concentration dependent manner. In hepatocytes lipid peroxidation was induced by ADP/Fe 3+ complex and cell damage was evaluated as LDH activity released in the medium. The inhibition of the peroxidative process by flavanolignans was also evident in this model, even if with a potency order different from that found in microsomes. In contrast, the effect on LDH release was significant only for silybin and isosilybin, the other compounds being inactive on this parameter.

Isolierung von Dihydrokämpferol aus Silybum marianum L. Gaertn. / Isolation of Dihydrokaempferol from Silybum marianum L. Gaertn.

Abstract Dihydrokaempferol ((2R, 3R)-2-(4-Hydroxy-phenyl)-3,5,7-trihydroxy-4-chromanon) has been isolated from the fruit of Silybum marianum L. Gaertn. and identified by UV, CD, MS and PMR spectra.

Isosilychristin, ein neues Flayonolignan aus Silybum marianum L. Gaertn. / Isosilychristin, a New Flavonolignan from Silybum marianum L.Gaertn.

Abstract A new flavonolignan, isosilychristin (1), has been isolated from the fruits of Silybum marianum L. Gaertn. Its structure and configuration is elucidated by spectroscopic methods.

Notizen: Silydianin und Silychristin, zwei isomere Silymarine aus Silybum marianum L. Gaertn. (Mariendistel) / Silydianin and Silychristin, two Isomeric Silymarins from Silybum marianum L. Gaertn. (milk thistle)

Two isomeric flavonolignans (Silymarins) have been isolated from the fruits of Silybum marianum L. Gaertn. and structurally elucidated mainly by means of NMR/mass spectroscopy and X-ray analysis respectively.

Flavonoids of the fruit ofSilybum marianum

Flavonoids of the fruit ofSilybum marianum