Structure Elucidation and Antioxidant Activity of (−)‐Isosilandrin Isolated from <i>Silybum marianum</i><scp>L.</scp>

Samu, Zsuzsanna; Nyiredy, Szabolcs; Baitz-Gács, Eszter; Varga, Zsuzsa; Kurtán, Tibor; Dinya, Zoltán; Antus, Sándor

doi:10.1002/cbdv.200490125

Cited by 25 publications

(18 citation statements)

References 29 publications

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“…Silandrin, isosilandrin, silyhermin, and silymonin have been isolated from the fruits of white-flowered S. marianum , var. albiflorum , growing in Hungary [8–10] and identified as 3-deoxy-isosilybin, 3-deoxy-silybin, 3-deoxy-silychristin and 3-deoxy-silydianin, respectively. Accordingly, eriodictyol constitutes the flavonoid moiety of these 3-deoxy flavonolignans.…”

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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Section: Introductionmentioning

confidence: 99%

Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations

et al. 2017

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“…While there is a possibility that this type of pathway could occur within or near the active site of an enzyme, 46,47 the probability of two radicals being formed independently in solution from Ag 2 O and then combining in a productive manner 18 is unlikely based on first principles of reaction kinetics. Since the concentration of both radicals will be extremely low, the reaction rate will be essentially zero.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle

et al. 2013

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The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.

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“…There are two botanical varieties for S. marianum based on flower colour. The purple variety contains 3-OH-flavonolignans, mainly silybin, isosilybin, silydianin and silychristin (Adzet et al, 1993), while white flower variety in addition contains 3-deoxy-flavonolignans: silandrin, isosylandrin, silymonin, silyhermin and neosilyhermin (Szilági et al, 1981;Samu et al, 2004;Nyiredy et al, 2008). Two chemotypes are identified for purple variety (Tab.…”

Section: Milk Thistle Active Constituents-chemotypesmentioning

confidence: 99%

Breeding Objectives and Selection Criteria for Milk Thistle [<i>Silybum marianum</i> (L.) Gaertn.] Improvement

Alemardan

Karkanis

Salehi

2013

Not Bot Hort Agrobot Cluj

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Milk thistle [Silybum marianum (L.) Gaertn.] is an important medicinal-industrial plant. The medicinal compounds of milk thistle are derived from its seeds. The plant is commercially cultivated for the production of silymarin. Cultivation offers the opportunity to optimise achene yield and silymarin content. Furthermore, efforts should be made to develop new cultivars. The main objective of milk thistle breeding is to develop high yielding cultivars with elevated silymarin content. There are few developed cultivars of milk thistle (e.g. Argintiu, Budakalaszi, Szibilla, Khoreslo, Babak Castle, Mirel, Silma and Silyb). Different genotypes of milk thistle have variable amount of silymarin e.g. a 'Royston' genotype is rich in silymarin (6-10%). Further progress can be made by using the genetic diversity available in abundance in different genotypes. The main concern of the breeder should be to increase the yield and silymarin contents of the seeds. Asynchronous flowering and seed shedding are also major problems in milk thistle cultivation. At the time of harvest, the plants have flower heads at all stages of development resulting non-uniform maturation of seeds. Therefore, a breeding effort in milk thistle should be planned to obtain plants with simultaneous flowering and reduced crop losses. The developed cultivar Argintiu is characterised by simultaneous seed maturation in flower heads. The wild populations, as valuable gene pools, could be exploited for the improvement of milk thistle crop.

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Structure Elucidation and Antioxidant Activity of (−)‐Isosilandrin Isolated from Silybum marianumL.

Cited by 25 publications

References 29 publications

Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations

Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations

Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle

Breeding Objectives and Selection Criteria for Milk Thistle [<i>Silybum marianum</i> (L.) Gaertn.] Improvement

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