Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography–electrospray tandem mass spectrometry

Lee, James I.; Hsu, Bih Hsiung.; Wu, Di; Barrett, Jeffrey S.

doi:10.1016/j.chroma.2006.03.053

Cited by 92 publications

(53 citation statements)

References 24 publications

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“…5 In the literature, milk thistle phenolic composition is characterized by the presence of a mixture of flavonolignans (silymarin), which are known to be normally present in its seeds. [33][34][35][36][37][38][39][40][41][42][43] [ ) flavonolignans (silymarin), assigned based on their UV spectra (λ max around 286-290 nm), the observation of the ion at m/z 481 and a very characteristic fragmentation pattern observed in many studies. [33][34][35][36][37][38][39][40][41][42][43] Nevertheless, due to the lack of commercial standards and difficulty in interpreting fragmentation, the complete identification of these compounds was not possible, and therefore they were characterized as silymarin derivatives.…”

Section: Food and Function Papermentioning

confidence: 99%

Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity

et al. 2016

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a Dietary supplements based on hepatoprotective plants have been increasingly used in the prevention of liver injuries. In the present work, the aim was to study the phenolic profile and possibly relate it to the in vitro antimicrobial activity of two different formulations ( pills and syrups) of artichoke and milk thistle, the antioxidant and anti-hepatocellular carcinoma activities of which were previously reported by our research group. The phenolic profiles were obtained by HPLC-DAD-ESI/MS, and the antimicrobial activity evaluation was performed with the clinical isolates of multiresistant bacteria (Escherichia coli, extended spectrum β-lactamases (ESBL) producing Escherichia coli, Proteus mirabilis, methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa). Artichoke syrup revealed the presence of vanillic acid and luteolin-7-O-glucoside while the pills possessed higher concentrations of 4-O-caffeoylquinic, 5-O-caffeoylquinic and 1,3-O-dicaffeoylquinic acids, this latest being able to inhibit the growth of MRSA.Regarding milk thistle formulations, the syrup presented isorhamnetin-O-deoxyhexoside-O-dihexoside, isorhamnetin-O-deoxyhexoside-O-hexoside and isorhamnetin-3-O-rutinoside as the major phenolic constituents whereas the pills were richer in taxifolin, silymarin derivatives and hydroxylated silibinin; the syrup revealed antimicrobial activity against all the studied bacteria with the exception of Proteus mirabilis whereas the pills revealed activity against ESBL producing Escherichia coli. Overall, all of the studied formulations revealed to be a good source of phenolic compounds, among which milk thistle syrup presented the highest variety and concentration of flavonoids, which is possibly related to its strongest antimicrobial activity.

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Section: Food and Function Papermentioning

confidence: 99%

Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity

et al. 2016

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“…12,14,17,19,21,[23][24][25][26][27]31 These compounds are known to be normally present in seeds of milk thistle. 17,19 Therefore, it can be concluded that the sample studied by us did not contain seeds, but only the other parts of the plant, even though the label mentioned the whole plant material.…”

Section: Flavonoidsmentioning

confidence: 99%

“…16,20 On the other hand, the medicinal properties of milk thistle are attributed to a polyphenolic mixture known as silymarin (present in the seeds), which contains several flavonolignans that are diastereomeric and/or constitutional isomers of each other, including silybin A, silybin B, isosilybin A, isosilybin B, silychristin, isosilychristin, and silydianin. 14,17,19,[21][22][23][24][25][26][27] Artichoke and milk thistle can be directly consumed in the diet or taken as infusions, among other available formulations, 18,28 allowing the dietary polyphenolic compounds to be absorbed through the gastrointestinal tract to reach the liver, where they are mainly metabolized. 6 Thus, in the present work, the aim was to obtain the phenolic profile of the most common parts used to prepare the infusions of these plants instead of their isolated parts that have already been well-reported as rich sources of these bioactive compounds; for that purpose, the phenolic profiles of hydromethanolic extracts and infusions prepared from the whole plant were assessed and compared.…”

Section: Introductionmentioning

confidence: 99%

Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids

et al. 2015

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Cynara scolymus L. (artichoke) and Silybum marianum (L.) Gaertn (milk thistle) are two herbs well-known for their efficiency in the prevention/treatment of liver injuries, among other chronic diseases. Therefore, the aim of this work was to characterize specific bioactive components, phenolic compounds, in hydromethanolic extracts but also in infusions (the most commonly used preparations) obtained from the whole plant of milk thistle and artichoke. The phenolic profiles were accessed using HPLC-DAD-MS/ESI. Infusions of both species presented higher phenolic contents than the hydromethanolic extracts. Milk thistle presented a similar phenolic composition between the two preparations, revealing only differences in the quantities obtained. Nevertheless, artichoke revealed a slightly different profile considering infusion and hydromethanolic extracts. Apigenin-7-O-glucuronide was the major flavonoid found in milk thistle, while luteolin-7-O-glucuronide was the most abundant in artichoke. Therefore, infusions of both artichoke and milk thistle represent a good source of bioactive compounds, especially phenolic acids and flavonoids.

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“…A number of methods utilizing HPLC and capillary electrophoresis were used for partial separation of the six components of silymarin [7,8], but the majority of these methods suffered from incomplete separation of silychristin, silydianin, and the two diastereoisomers of silybin and isosilybin. Recent studies focused on quantifying each component of silymarin obtained from the fruits and seeds or in different commercial products using either HPLC or a newly developed capillary zone electrophoresis method [9][10][11]. To the best of our knowledge, the leaves of S. marianum have not previously been evaluated for their bioactive components.…”

Section: Introductionmentioning

confidence: 99%

First detailed quantification of silymarin components in the leaves ofSilybum marianumcultivated in egypt during different growth stages

Omar¹,

Hadad²,

Badr³

2012

Acta Chromatographica

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Summary.A high performance liquid chromatographic method was developed for the quantitative determination of the active components of silymarin in the leaves of Silybum marianum during different growth stages. In this study, taxifolin and six main active constituents in silymarin, including silydianin, silychristin, diastereomers of silybin (silybin A and B) and diastereomers of isosilybin (isosilybin A and B) were completely separated on a 5-µm ODS column (Luna, Phenomenex, USA) with a mobile phase consisting of methanol and 5 mM NaH 2 PO 4 (pH 3.5 adjusted with phosphoric acid) in a ratio of 45:55 v/v. Quantitation was performed with UV detection at 280 nm, based on peak area. The concentration of each component, as well as the total silymarin concentration was determined and compared with those of the seeds, aiming at optimizing the utilization of the cultivated plant. The developed method was validated with respect to linearity, range, specificity, accuracy, precision, and robustness. The leaves were found to contain such concentrations of silymarin components that the yield is better per field area than that from the seeds. Moreover, the extraction of these components from leaves is nonexpensive and simpler than the extraction from seeds.

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Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography–electrospray tandem mass spectrometry

Cited by 92 publications

References 24 publications

Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity

Artichoke and milk thistle pills and syrups as sources of phenolic compounds with antimicrobial activity

Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids

First detailed quantification of silymarin components in the leaves ofSilybum marianumcultivated in egypt during different growth stages

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