The silymarin composition… and why does it matter???

Chambers, Christopher S.; Holečková, Veronika; Petrásková, Lucie; Biedermann, David; Valentová, Kateřina; Buchta, Martin; Křen, Vladimı́r

doi:10.1016/j.foodres.2017.07.017

Cited by 119 publications

(110 citation statements)

References 84 publications

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“…This is in contrast with the theoretical O–H bond dissociation enthalpies, which are almost the same for both diastereomers [20]. In addition, our results show that the antioxidant/antiradical activities of both sulfated and parent [5] flavonolignans are lower than that of the flavanonol taxifolin (for DPPH scavenging, IC 50 = 6–10 µM) [24,25], which accounts for up to 5% in various silymarin preparations [26]. …”

Section: Resultscontrasting

confidence: 73%

Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Valentová

Purchartová

Rydlová

et al. 2018

IJMS

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Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). Their 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and N,N-dimethyl-p-phenylenediamine (DMPD) radical scavenging; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity.

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Section: Resultscontrasting

confidence: 73%

Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Valentová

Purchartová

Rydlová

et al. 2018

IJMS

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“…The main characteristic of all the populations, except those from Spata (P2) and Kastoria (P17), was the substantial amount of isosilybin (A and B), with values between 25 and 40% of the total flavonolignan content in silymarin. Although the biological activity of silymarin is often assigned to silybin A and silybin B (Chambers et al, ), some reports support the contribution of other flavonolignans to the beneficial effects of silymarin. According to Deep, Oberlies, Kroll, and Agarwal (), isosilybin B is a valuable agent against prostate cancer, while Davis‐Searles et al () have identified the important roles of both isosilybin A and B as inhibitors of prostate carcinoma growth.…”

Section: Discussionmentioning

confidence: 99%

“…is an annual or biennial species belonging to the Asteraceae family; it is a common weed found in winter cereal fields, roadsides and undisturbed areas in the Mediterranean basin and other European regions (Andrzejewska, Martinelli, & Sadowska, ; Andrzejewska, Sadowska, & Mielcarek, ; Karkanis, Efthimadou, & Bilalis, ; Martinelli, Andrzejewska, Salis, & Sulas, ). Milk thistle seed (botanically correct: fruits) extracts, as well as their constituents, exhibit several medicinal properties (Abenavoli, Capasso, Milic, & Capasso, ; Chambers et al, ; Karkanis et al, ). The pharmacological activity of the seed extracts is because of silymarin, an extract containing the flavonoid taxifolin and several flavonolignans, including silybin A and B, isosilybin A and B, silychristin, isosilychristin and silydianin (Chambers et al, ; Kroll, Shaw, & Oberlies, ).…”

Section: Introductionmentioning

confidence: 99%

“…Milk thistle seed (botanically correct: fruits) extracts, as well as their constituents, exhibit several medicinal properties (Abenavoli, Capasso, Milic, & Capasso, ; Chambers et al, ; Karkanis et al, ). The pharmacological activity of the seed extracts is because of silymarin, an extract containing the flavonoid taxifolin and several flavonolignans, including silybin A and B, isosilybin A and B, silychristin, isosilychristin and silydianin (Chambers et al, ; Kroll, Shaw, & Oberlies, ). Silymarin acts mainly as a hepatoprotective (Patel, Joseph, Corcoran, & Ray, ) and anticancer agent (Wu et al, ) and, in 2016, milk thistle was placed in 6th and 16th position among herbal supplements in the natural ($10.0 million) and mainstream multioutlet channels ($17.1 million), respectively, in the United States (Smith, Kawa, Eckl, Morton, & Stredney, ).…”

Section: Introductionmentioning

confidence: 99%

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Silymarin content and antioxidant activity of seeds of wild Silybum marianum populations growing in Greece

Arampatzis

Karkanis

Tsiropoulos

2018

Annals of Applied Biology

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Selection of milk thistle (Silybum marianum (L.) Gaertn.) genotypes for commercial cultivation depends on wild population resources, rather than on selection of varieties. The evaluation of these populations could contribute to the development of new milk thistle varieties with desirable traits such as high silymarin content. Therefore, we conducted a study to evaluate 30 wild populations occurring naturally in Greece, based on seed silymarin content. Seeds were collected from populations growing in localities presenting different environmental conditions. In addition, we also investigated the diversity in levels of silymarin constituents, as well as observed correlations among them. Significant differences in silymarin content were recorded among the populations studied, with values ranging from 2.31 to 7.71% (avg. 3.31%), as well as in flavonolignan and taxifolin content. The mean taxifolin content was 4.96 mg/g, while the highest silybin A + silybin B content (21.77-31.39 mg/g of dry weight (dw)) was recorded in seeds from the "Spata" population originating from central Greece. Our results showed noticeable levels of diversity in silymarin content and composition in native milk thistle populations, indicating that a valuable gene pool for exploitation in milk thistle breeding programmes exists in Greece. K E Y W O R D S flavonolignans, medicinal plant, milk thistle, silybin, taxifolin

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“…The main active substance found in milk thistle is silymarin (a mixture of at least four closely related flavonolignans), which has been documented to be a hepatoprotective compound. Silymarin is a mixture of silybin A and B (approximately 50–60%), silydianin (about 10%), silychristin (about 20%) and isosilybin A and B (about 5%) (Abenavoli et al ., ; Karkanis et al ., ; Chambers et al ., ). The flavonolignans of silymarin exhibit numerous biological activities such as antioxidant, anti‐inflammatory and immunomodulatory effects.…”

Section: Introductionmentioning

confidence: 97%

Phytochemical profile of Silybum marianum (L.) Gaertn. and Graminis rhizoma and its influence on the bioactivity and shelf life of industrially produced pâté

Ferysiuk

Wójciak

Materska

2019

Int J of Food Sci Tech

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Summary The impact of the use of Silybum marianum and G. rhizoma plant powders on the nutritional value of cooked pâté was explored. Three concentrations (5%, 10% and 15%) for S. marianum and two (5% and 10%) for G. rhizoma were added. The phytochemical profile of plant extracts was analysed using HPLC. The pH value, water activity, TBARS, oxidation–reduction potential, total phenolic content, antioxidant capacity, instrumental colour and microbiology of cooked pâtés were determined after 1 and 21 days of storage. Basic chemical composition, dietary fibre, elemental and nitrites/nitrates content were determined, and sensory analysis was performed after product preparation. Phenolic contents and antioxidant activities of fortified patties strongly correlated with the lower level of ORP and TBARS values. The obtained results indicate that the addition of S. marianum at a concentration of 10% is most beneficial for sensory attributes, colour stabilisation and antioxidant capacity.

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The silymarin composition… and why does it matter???

Cited by 119 publications

References 84 publications

Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Silymarin content and antioxidant activity of seeds of wild Silybum marianum populations growing in Greece

Phytochemical profile of Silybum marianum (L.) Gaertn. and Graminis rhizoma and its influence on the bioactivity and shelf life of industrially produced pâté

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