Silymarin, Natural Flavonolignans from Milk Thistle

AbouZid, Sameh

doi:10.5772/26027

Cited by 13 publications

(3 citation statements)

References 59 publications

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“…Subsequently, the adduct undergoes cyclization by the addition of the phenol nucleophile to the quinine methide, generated by the coniferyl alcohol. The formation of two silybin diastereoisomers indicates that the radical coupling reaction is not stereospecific [ 36 , 37 ].…”

Section: Silybin Structure and Chemistrymentioning

confidence: 99%

Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)—Chemistry, Bioavailability, and Metabolism

2017

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Milk thistle (Silybum marianum) is a medicinal plant that has been used for thousands of years as a remedy for a variety of ailments. The main component of S. marianum fruit extract (silymarin) is a flavonolignan called silybin, which is not only the major silymarin element but is also the most active ingredient of this extract, which has been confirmed in various studies. This compound belongs to the flavonoid group known as flavonolignans. Silybin’s structure consists in two main units. The first is based on a taxifolin, the second a phenyllpropanoid unit, which in this case is conyferil alcohol. These two units are linked together into one structure by an oxeran ring. Since the 1970s, silybin has been regarded in official medicine as a substance with hepatoprotective properties. There is a large body of research that demonstrates silybin’s many other healthy properties, but there are still a lack of papers focused on its molecular structure, chemistry, metabolism, and novel form of administration. Therefore, the aim of this paper is a literature review presenting and systematizing our knowledge of the silybin molecule, with particular emphasis on its structure, chemistry, bioavailability, and metabolism.

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Section: Silybin Structure and Chemistrymentioning

confidence: 99%

Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)—Chemistry, Bioavailability, and Metabolism

2017

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“…Anti-tumour activities of Naphthalimides were enhanced by synthesizing bis-intercalating agents like Naphthalene diimides to improve the interactions with the phosphate groups of DNA, which resulted in anticancer properties against several human cancer cell lines. 5 – 7 Other groups of compounds include (1) Benzodioxane derivatives that exhibit a range of activities including anti-tumour, anti-microbial and antioxidant activities; 8 – 10 (2) Acetamol derivatives that have been implicated in cytotoxicity and/or apoptosis of host cells, 11 albeit they have been used commonly to treat pain and fever, 12 , 13 and (3) Porphyrins that have been used extensively in the context of photodynamic therapy (PDT). The basis of PDT is that the light of appropriate wavelength activates the photosensitising compound, resulting in production of singlet oxygen and other reactive oxygen species (ROS) to induce cell death in the target tissue.…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic effects of Benzodioxane, Naphthalene diimide, Porphyrin and Acetamol derivatives on HeLa cells

et al. 2018

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Objectives:To synthesize novel compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin classes and test their potential anticancer properties.Methods:Several compounds were synthesized and their molecular identity was confirmed using nuclear magnetic resonance. Potential anticancer properties were determined using cytopathogenicity assays and growth inhibition assays using cervical cancer cells (HeLa). Cells were incubated with different concentrations of compounds belonging to Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins and effects were determined. HeLa cells cytopathogenicity was determined by measuring lactate dehydrogenase release using cytotoxicity detection assay. Growth inhibition assays were performed by incubating 50% semi-confluent HeLa cells with Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrin compounds and HeLa cell proliferation was observed. Growth inhibition and host cell death were compared in the presence and absence of drugs.Results:Cytopathogenicity assays showed that the selected compounds were cytotoxic against HeLa cells, killing up to 90% of cells. Growth inhibition assays exhibited 100% growth inhibition. These effects are likely via oxidative stress, production of reactive oxygen species, changes in cytosolic and intracellular calcium/adenine nucleotide homeostasis, inhibition of ribonucleotide reductase/cyclooxygenase and/or glutathione depletion.Conclusions:Benzodioxane, Naphthalene diimide, Aminophenol derivatives and Porphyrins exhibited potent anticancer properties. These findings are promising and should pave the way in the rationale development of anticancer drugs. Using different cancer cell lines, future studies will determine their potential as anti-tumour agents as well as their precise molecular mode of action.

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“…The fruits contain up to 9% of those compounds, which mainly accumulate in their external cover. , The hepatoprotective activity of silymarin can be explained by the antioxidant properties as a result of the phenolic nature of flavonolignans, stimulating liver cell regeneration and cell membrane stabilization to prevent hepatotoxic agents from entering hepatocytes . Numerous studies have demonstrated the efficacy of silymarin as hepatoprotective but also as an anti-inflammatory, antioxidant, antifibrotic, and cancer chemopreventive agent. − …”

Section: Introductionmentioning

confidence: 99%

Head-to-Head Comparison of Ultra-High-Performance Liquid Chromatography with Diode Array Detection versus Quantitative Nuclear Magnetic Resonance for the Quantitative Analysis of the Silymarin Complex in Silybum marianum Fruit Extracts

Cheilari

Sturm

Intelmann

et al. 2016

J. Agric. Food Chem.

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Quantitative nuclear magnetic resonance (qNMR) spectroscopy is known as an excellent alternative to chromatography-based mixture analysis. NMR spectroscopy is a non-destructive method, needs only limited sample preparation, and can be readily automated. A head-to-head comparison of qNMR to an ultra-high-performance liquid chromatography with diode array detection (uHPLC-DAD)-based quantitative analysis of six flavonolignan congeners (silychristin, silydianin, silybin A, silybin B, isosilybin A, and isosilybin B) of the Silybum marianum silymarin complex is presented. Both assays showed similar performance characteristics (linear range, accuracy, precision, and limits of quantitation) with analysis times below 30 min/sample. The assays were applied to industrial S. marianum extracts (AC samples) and to extracts locally prepared from S. marianum fruits (PL samples). An assay comparison by Bland-Altman plots (relative method bias AC samples, -0.1%; 2SD range, ±5.1%; relative method bias PL samples, -0.3%; 2SD range, ±7.8%) and Passing-Bablok regression analysis (slope and intercept for AC and PL samples not significantly different from 1.00 and 0.00, respectively; Spearman's coefficient of rank correlation, >0.99) did show that qNMR and uHPLC-DAD can be used interchangeably to quantitate flavonolignans in the silymarin complex.

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Silymarin, Natural Flavonolignans from Milk Thistle

Cited by 13 publications

References 59 publications

Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)—Chemistry, Bioavailability, and Metabolism

Silybin, a Major Bioactive Component of Milk Thistle (Silybum marianum L. Gaernt.)—Chemistry, Bioavailability, and Metabolism

Cytotoxic effects of Benzodioxane, Naphthalene diimide, Porphyrin and Acetamol derivatives on HeLa cells

Head-to-Head Comparison of Ultra-High-Performance Liquid Chromatography with Diode Array Detection versus Quantitative Nuclear Magnetic Resonance for the Quantitative Analysis of the Silymarin Complex in Silybum marianum Fruit Extracts

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