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Silymarin
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Silymarin

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 November 2016) | Viewed by 83221

Special Issue Editors

Prof. Dr. Tung-Hu Tsai

E-Mail Website
Guest Editor
Institute of Traditional Medicine, School of Medicine, National Yang Ming Chiao Tung University, Taipei 11221, Taiwan
Interests: animal experiment; blood–brain barrier; blood–placental barrier; drug–drug interactions; enterohepatic circulation; food chemistry; herbal medicine; liquid chromatography; LC-MS/MS; microdialysis; natural products; neurochemistry; pharmaceutical analysis; pharmacodynamics; pharmacokinetics; traditional Chinese medicine; transporter mechanism
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Youngjin Jeon

E-Mail Website
Guest Editor
Department of Pharmacology, Chosun University College of Medicine, Gwangju, South Korea
Interests: macrophage function; cancer stem cells; tumorigenesis; chemoprevention; signal transduction

Special Issue Information

Dear Colleagues,

In the last decade, the investigation of silymarin has grown to over 100 articles per year. Previous articles revealed that silymarin was a multi-bioactivity component isolated from milk thistle, and its well-known bioactivity has hepatoprotective effects. Recent research has been focused on clinical trials, formulation design, and pharmacokinetic evaluations. Despite its effective bioactivities in vitro, silymarin suffers from poor absorption with low bioavailability, and does not provide an effective efficacy. Because of its significant hepatoprotective, antioxidative, antitumor, and neuroprotective effects, silymarin is frequently co-administered with clinical drugs. Based on the drug safety concern, the herb–drug interaction should be carefully examined. This Special Issue aims to encompass papers at the forefront of research in the field, by dealing with the following topical issues: therapeutic efficacy; efforts to develop new formulations or nano-drug delivery carriers to improve oral bioavailability; prolongation of drug action; herb–drug interaction studies in pre-clinical trials and clinical trials; and the absorption, distribution, metabolism, and elimination studies of silymarin.

As Guest Editors, we cordially invite researchers to submit your work relevant to this Special Issue of Molecules.

Prof. Tung-Hu Tsai
Prof. Youngjin Jeon
Guest Editor

Manuscript Submission Information

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Keywords

  • silymarin
  • nature products
  • herb-drug interaction
  • pharmacokinetics
  • pharmacodynamics
  • hepatoprotective
  • pharmaceutical formulation

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Published Papers (4 papers)

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Research

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1588 KiB  
Article
Role of UDP-Glucuronosyltransferase 1A1 in the Metabolism and Pharmacokinetics of Silymarin Flavonolignans in Patients with HCV and NAFLD
by Ying Xie, Sonia R. Miranda, Janelle M. Hoskins and Roy L. Hawke
Molecules 2017, 22(1), 142; https://doi.org/10.3390/molecules22010142 - 15 Jan 2017
Cited by 18 | Viewed by 7895
Abstract
Silymarin is the most commonly used herbal medicine by patients with chronic liver disease. Silymarin flavonolignans undergo rapid first-pass metabolism primarily by glucuronidation. The aims of this investigation were: (1) to determine the association of UGT1A1*28 polymorphism with the area under the plasma [...] Read more.
Silymarin is the most commonly used herbal medicine by patients with chronic liver disease. Silymarin flavonolignans undergo rapid first-pass metabolism primarily by glucuronidation. The aims of this investigation were: (1) to determine the association of UGT1A1*28 polymorphism with the area under the plasma concentration-time curves (AUCs) for silybin A (SA) and silybin B (SB); (2) to evaluate the effect of UGT1A1*28 polymorphism on the profile of flavonolignan glucuronide conjugates found in the plasma; and (3) to investigate the role of UGT1A1 enzyme kinetics on the pharmacokinetics of SA and SB. AUCs and metabolic ratios for thirty-three patients with chronic liver disease administered oral doses of silymarin were compared between different UGT1A1*28 genotypes. The AUCs, metabolic ratios, and the profiles of major SA and SB glucuronides did not differ significantly among the three UGT1A1 genotypes. In contrast, an increase in the proportion of sulfated flavonolignan conjugates in plasma was observed in subjects with UGT1A1*28/*28 genotype compared to subjects carrying wild type alleles. Differences in SA and SB in vitro intrinsic clearance estimates for UGTIA1 correlated inversely with SA and SB exposures observed in vivo indicating a major role for UGT1A1 in silymarin metabolism. In addition, a significant difference in the metabolic ratio observed between patients with NAFLD and HCV suggests that any effect of UGT1A1 polymorphism may be obscured by a greater effect of liver disease on the pharmacokinetics of silymarin. Taken together, these results suggest the presence of the UGT1A1*28 allele does not contribute significantly to a large inter-subject variability in the pharmacokinetics of silybin A and silybin B which may obscure the ability to detect beneficial effects of silymarin in patients with liver disease. Full article
(This article belongs to the Special Issue Silymarin)
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3763 KiB  
Article
A Novel Role of Silibinin as a Putative Epigenetic Modulator in Human Prostate Carcinoma
by Ioannis Anestopoulos, Aristeidis P. Sfakianos, Rodrigo Franco, Katerina Chlichlia, Mihalis I. Panayiotidis, David J. Kroll and Aglaia Pappa
Molecules 2017, 22(1), 62; https://doi.org/10.3390/molecules22010062 - 31 Dec 2016
Cited by 40 | Viewed by 9558
Abstract
Silibinin, extracted from milk thistle (Silybum marianum L.), has exhibited considerable preclinical activity against prostate carcinoma. Its antitumor and chemopreventive activities have been associated with diverse effects on cell cycle, apoptosis, and receptor-dependent mitogenic signaling pathways. Here we hypothesized that silibinin’s pleiotropic [...] Read more.
Silibinin, extracted from milk thistle (Silybum marianum L.), has exhibited considerable preclinical activity against prostate carcinoma. Its antitumor and chemopreventive activities have been associated with diverse effects on cell cycle, apoptosis, and receptor-dependent mitogenic signaling pathways. Here we hypothesized that silibinin’s pleiotropic effects may reflect its interference with epigenetic mechanisms in human prostate cancer cells. More specifically, we have demonstrated that silibinin reduces gene expression levels of the Polycomb Repressive Complex 2 (PRC2) members Enhancer of Zeste Homolog 2 (EZH2), Suppressor of Zeste Homolog 12 (SUZ12), and Embryonic Ectoderm Development (EED) in DU145 and PC3 human prostate cancer cells, as evidenced by Real Time Polymerase Chain Reaction (RT-PCR). Furthermore immunoblot and immunofluorescence analysis revealed that silibinin-mediated reduction of EZH2 levels was accompanied by an increase in trimethylation of histone H3 on lysine (Κ)-27 residue (H3K27me3) levels and that such response was, in part, dependent on decreased expression levels of phosphorylated Akt (ser473) (pAkt) and phosphorylated EZH2 (ser21) (pEZH2). Additionally silibinin exerted other epigenetic effects involving an increase in total DNA methyltransferase (DNMT) activity while it decreased histone deacetylases 1-2 (HDACs1-2) expression levels. We conclude that silibinin induces epigenetic alterations in human prostate cancer cells, suggesting that subsequent disruptions of central processes in chromatin conformation may account for some of its diverse anticancer effects. Full article
(This article belongs to the Special Issue Silymarin)
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2790 KiB  
Article
Efficacy of Pre- and Post-Treatment by Topical Formulations Containing Dissolved and Suspended Silybum marianum against UVB-Induced Oxidative Stress in Guinea Pig and on HaCaT Keratinocytes
by Pálma Fehér, Zoltán Ujhelyi, Judit Váradi, Ferenc Fenyvesi, Eszter Róka, Béla Juhász, Balázs Varga, Mariann Bombicz, Dániel Priksz, Ildikó Bácskay and Miklós Vecsernyés
Molecules 2016, 21(10), 1269; https://doi.org/10.3390/molecules21101269 - 22 Sep 2016
Cited by 35 | Viewed by 6906
Abstract
Plants with high amounts of antioxidants may be a promising therapy for preventing and curing UV-induced oxidative skin damage. The objective of this study was to verify the efficacy of topical formulations containing dissolved and suspended Silybum marianum extract against UVB-induced oxidative stress [...] Read more.
Plants with high amounts of antioxidants may be a promising therapy for preventing and curing UV-induced oxidative skin damage. The objective of this study was to verify the efficacy of topical formulations containing dissolved and suspended Silybum marianum extract against UVB-induced oxidative stress in guinea pig and HaCaT keratinocytes. Herbal extract was dissolved in Transcutol HP (TC) and sucrose-esters were incorporated as penetration enhancers in creams. Biocompatibility of compositions was tested on HeLa cells and HaCaT keratinocytes as in vitro models. Transepidermal water loss (TEWL) tests were performed to prove the safety of formulations in vivo. Drug release of different compositions was assessed by Franz diffusion methods. Superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx) and lipid peroxidation (MDA) activities were evaluated before and after UVB irradiation in a guinea pig model and HaCaT cells. Heme oxygenase-1 (HO-1) enzyme activity was measured in the epidermis of guinea pigs treated by different creams before and after UVB irradiation. Treatment with compositions containing silymarin powder (SM) dissolved in TC and sucrose stearate SP 50 or SP 70 resulted in increased activities of all reactive oxygen species (ROS) eliminating enzymes in the case of pre- and post-treatment as well. Reduction in the levels of lipid peroxidation end products was also detected after treatment with these two compositions. Post-treatment was more effective as the increase of the activity of antioxidants was higher. Lower HO-1 enzyme levels were measured in the case of pre- and post-treatment groups compared to control groups. Therefore, this study demonstrates the effectiveness of topical formulations containing silymarin in inhibiting UVB irradiation induced oxidative stress of the skin. Full article
(This article belongs to the Special Issue Silymarin)
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Review

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1461 KiB  
Review
Silymarin/Silybin and Chronic Liver Disease: A Marriage of Many Years
by Alessandro Federico, Marcello Dallio and Carmelina Loguercio
Molecules 2017, 22(2), 191; https://doi.org/10.3390/molecules22020191 - 24 Jan 2017
Cited by 348 | Viewed by 57768
Abstract
Silymarin is the extract of Silybum marianum, or milk thistle, and its major active compound is silybin, which has a remarkable biological effect. It is used in different liver disorders, particularly chronic liver diseases, cirrhosis and hepatocellular carcinoma, because of its antioxidant, [...] Read more.
Silymarin is the extract of Silybum marianum, or milk thistle, and its major active compound is silybin, which has a remarkable biological effect. It is used in different liver disorders, particularly chronic liver diseases, cirrhosis and hepatocellular carcinoma, because of its antioxidant, anti-inflammatory and antifibrotic power. Indeed, the anti-oxidant and anti-inflammatory effect of silymarin is oriented towards the reduction of virus-related liver damages through inflammatory cascade softening and immune system modulation. It also has a direct antiviral effect associated with its intravenous administration in hepatitis C virus infection. With respect to alcohol abuse, silymarin is able to increase cellular vitality and to reduce both lipid peroxidation and cellular necrosis. Furthermore, silymarin/silybin use has important biological effects in non-alcoholic fatty liver disease. These substances antagonize the progression of non-alcoholic fatty liver disease, by intervening in various therapeutic targets: oxidative stress, insulin resistance, liver fat accumulation and mitochondrial dysfunction. Silymarin is also used in liver cirrhosis and hepatocellular carcinoma that represent common end stages of different hepatopathies by modulating different molecular patterns. Therefore, the aim of this review is to examine scientific studies concerning the effects derived from silymarin/silybin use in chronic liver diseases, cirrhosis and hepatocellular carcinoma. Full article
(This article belongs to the Special Issue Silymarin)
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