Silymarin synthesis and degradation by peroxidases of cell suspension cultures of Silybum marianum

Sánchez-Sampedro, María Angeles; Fernández‐Tárrago, Jorge; Corchete, Purificación

doi:10.1016/j.jplph.2006.06.015

Cited by 11 publications

(6 citation statements)

References 23 publications

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“…According to Dewick (2002), the two molecules, after one-electron oxidation, are able to perform a radical coupling, therefore producing silymarin flavonolignans. The results obtained by Becker and Schrall (1977), and confirmed by Sánchez-Sampedro et al (2007), indicate that milk thistle extracellular peroxidases is reputed to be responsible for the oxidative coupling between the two precursors. The results obtained by Becker and Schrall (1977), and confirmed by Sánchez-Sampedro et al (2007), indicate that milk thistle extracellular peroxidases is reputed to be responsible for the oxidative coupling between the two precursors.…”

Section: Discussionmentioning

confidence: 77%

“…The different isomers are the result of the position of radical groups that are each time present on the two precursors. The results obtained by Becker and Schrall (1977), and confirmed by Sánchez-Sampedro et al (2007), indicate that milk thistle extracellular peroxidases is reputed to be responsible for the oxidative coupling between the two precursors. Despite that, it is not known if peroxidases are the only enzymes involved in the final step of flavonolignans biosynthesis (Sánchez-Sampedro et al, 2007).…”

Section: Discussionmentioning

confidence: 77%

“…The results obtained by Becker and Schrall (1977), and confirmed by Sánchez‐Sampedro et al (2007), indicate that milk thistle extracellular peroxidases is reputed to be responsible for the oxidative coupling between the two precursors. Despite that, it is not known if peroxidases are the only enzymes involved in the final step of flavonolignans biosynthesis (Sánchez‐Sampedro et al, 2007). In this study, a strong and positive correlation between silychristin and silybins (A and B) content and between silydianin and isosilybin B content has been reported, this suggests that the biosynthetic pathway of these groups of molecules might not be completely independent as proposed by the sole extracellular peroxidase model.…”

Section: Discussionmentioning

confidence: 77%

“…The different isomers are the result of the position of radical groups that are each time present on the two precursors. Despite that, it is not known if peroxidases are the only enzymes involved in the final step of flavonolignans biosynthesis (Sánchez-Sampedro et al, 2007). Despite that, it is not known if peroxidases are the only enzymes involved in the final step of flavonolignans biosynthesis (Sánchez-Sampedro et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

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Phenotypic Evaluation of a Milk Thistle Germplasm Collection: Fruit Morphology and Chemical Composition

et al. 2016

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Milk thistle [Silybum marianum (L.) Gaertn.] is an officinal crop species native to the Mediterranean. The species is gaining increasing interest as a multipurpose crop, but lack of information exists about the natural phenotypic variability available in the species for the traits of interest. In the present work, the fruit morphological and chemical traits of a collection of 26 milk thistle accessions have been analyzed. The results show that the most variable traits are related to single flavonolignan content. When the most abundant fatty acids present in the fruit are considered, oleic acid appears to have the higher variability between accessions. Correlations between variables highlight strong relationships between the different flavonolignans and a strong positive correlation between isosilybin A and the total silymarin content, suggesting a central role of this minor flavonolignan in silymarin biosynthetic pathway. The clustering procedure displays considerable diversity between the accessions that originate from localities where milk thistle is described as a native species.

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Section: Discussionmentioning

confidence: 77%

Section: Discussionmentioning

confidence: 77%

Section: Discussionmentioning

confidence: 77%

Section: Discussionmentioning

confidence: 99%

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Phenotypic Evaluation of a Milk Thistle Germplasm Collection: Fruit Morphology and Chemical Composition

et al. 2016

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“…The enzyme catalyzing the oxidative coupling of flavonolignans has not yet been characterized. However, in vitro synthesis of flavonolignans (silybinins) was achieved by peroxidase (EC 1.11.1.7) of S. marianum cell suspension culture [11]. This reaction is initiated by one-electron oxidation of (+)-taxifolin to a phenoxy radical that couples with a quinone methide radical, generated from coniferyl alcohol.…”

Section: Introductionmentioning

confidence: 99%

Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations

et al. 2017

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Flavonolignans constitute an important class of plant secondary metabolites formed by oxidative coupling of one flavonoid and one phenylpropanoid moiety. The standardized flavonolignan-rich extract prepared from the fruits of Silybum marianum is known as silymarin and has long been used medicinally, prominently as an antihepatotoxic and as a chemopreventive agent. Principal component analysis of the variation in flavonolignan content in S. marianum samples collected from different locations in Egypt revealed biosynthetic relationships between the flavonolignans. Silybin A, silybin B, and silychristin are positively correlated as are silydianin, isosilychristin, and isosilybin B. The detection of silyamandin in the extracts of S. marianum correlates with isosilychristin and silydianin content. The positive correlation between silydianin, isosilychristin, and silyamandin was demonstrated using quantitative 1H nuclear magnetic resonance spectroscopy (qHNMR). These correlations can be interpreted as evidence for the involvement of a flavonoid radical in the biosynthesis of the flavonolignans in S. marianum. The predominance of silybins A & B over isosilybin A & B in the silybin-rich samples is discussed in light of the relative stabilities of their respective radical flavonoid biosynthetic intermediates.

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Silybum marianum (L.) Gaertn: the Source of Silymarin

Corchete

2008

Bioactive Molecules and Medicinal Plants

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Silymarin synthesis and degradation by peroxidases of cell suspension cultures of Silybum marianum

Cited by 11 publications

References 23 publications

Phenotypic Evaluation of a Milk Thistle Germplasm Collection: Fruit Morphology and Chemical Composition

Phenotypic Evaluation of a Milk Thistle Germplasm Collection: Fruit Morphology and Chemical Composition

Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations

Silybum marianum (L.) Gaertn: the Source of Silymarin

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