2,3-Dehydroderivatives of Silymarin Flavonolignans: Prospective Natural Compounds for the Prevention of Chronic Diseases

Valentová, Kateřina; Biedermann, David; Křen, Vladimı́r

doi:10.3390/proceedings2019011021

Cited by 4 publications

(4 citation statements)

References 15 publications

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“…The main explanation probably lies in the differences in their structure, namely the additional double bond at position C-2, C-3 for 2,3-dehydrosilychristin and at position C-10, C-11 in the structure of anhydrosilychristin (Figure 1). This is in line with the previously reported DPPH and ABTS scavenging, reducing and anti-lipoperoxidant activity of not only 2,3-dehydrosilychristin and anhydrosilychristin, but also other 2,3-dehydroflavonolignans compared with their parent flavonolignans [1,4,36,37,38].…”

Section: Discussionsupporting

confidence: 93%

Antioxidant, Anti-Inflammatory, and Multidrug Resistance Modulation Activity of Silychristin Derivatives

et al. 2019

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Silychristin A is the second most abundant compound of silymarin. Silymarin complex was previously described as an antioxidant with multidrug resistance modulation activity. Here, the results of a classical biochemical antioxidant assay (ORAC) were compared with a cellular assay evaluating the antioxidant capacity of pure silychristin A and its derivatives (anhydrosilychristin, isosilychristin and 2,3-dehydrosilychristin A). All the tested compounds acted as antioxidants within the cells, but 2,3-dehydro- and anhydro derivatives were almost twice as potent as the other tested compounds. Similar results were obtained in LPS-stimulated macrophages, where 2,3-dehydro- and anhydrosilychristin inhibited NO production nearly twice as efficiently as silychristin A. The inhibition of P-glycoprotein (P-gp) was determined in vitro, and the respective sensitization of doxorubicin-resistant ovarian carcinoma overproducing P-gp was detected. Despite the fact that the inhibition of P-gp was demonstrated in a concentration-dependent manner for each tested compound, the sensitization of the resistant cell line was observed predominantly for silychristin A and 2,3-dehydrosilychristin A. However, anhydrosilychristin and isosilychristin affected the expression of both the P-gp (ABCB1) and ABCG2 genes. This is the first report showing that silychristin A and its 2,3-dehydro-derivative modulate multidrug resistance by the direct inhibition of P-gp, in contrast to anhydrosilychristin and isosilychristin modulating multidrug resistance by downregulating the expression of the dominant transmembrane efflux pumps.

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Section: Discussionsupporting

confidence: 93%

Antioxidant, Anti-Inflammatory, and Multidrug Resistance Modulation Activity of Silychristin Derivatives

et al. 2019

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“…As expected, the activity of retinoic acid ( 2 ) was about half that of retinol ( 1 ) with IC 50 values 745 and 1485 µM, respectively. In accordance with our previously published data [25,34,35,36] also parent flavonolignans 3ab , 3a , 3b and 5a displayed relatively low activity (IC 50 472–818 µM), while 2,3-dehydrosilybin ( 4 ) was much more active (19.2 µM, Table 1). The conjugates 6a and 6b with silybin diastereomers displayed significantly better DPPH scavenging activity (IC 50 379 and 540 µM) than both the parent compounds and their equimolar mixtures.…”

Section: Resultssupporting

confidence: 92%

Preparation of Retinoyl-Flavonolignan Hybrids and Their Antioxidant Properties

et al. 2019

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Antioxidants protect the structural and functional components in organisms against oxidative stress. Most antioxidants are of plant origin as the plants are permanently exposed to oxidative stress (UV radiation, photosynthetic reactions). Both carotenoids and flavonoids are prominent antioxidant and anti-radical agents often occurring together in the plant tissues and acting in lipophilic and hydrophilic milieu, respectively. They are complementary in their anti-radical activity. This study describes the synthesis of a series of hybrid ester conjugates of retinoic acid with various flavonolignans, such as silybin, 2,3-dehydrosilybin and isosilybin. Antioxidant/anti-radical activities and bio-physical properties of novel covalent carotenoid-flavonoid hybrids, as well as various mixtures of the respective parent components, were investigated. Retinoyl conjugates with silybin—which is the most important flavonolignan in silymarin complex—(and its pure diastereomers) displayed better 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than both the parent compounds and their equimolar mixtures.

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“…30% of a polymeric phenolic fraction [8,9]. These compounds and their derivatives generally have low toxicity and interesting biological activity, such as hepatoprotective activity, anti-inflammatory activity, antioxidant activity, and the ability to modulate the pumps associated with multidrug resistance [8,[10][11][12]. The halogenation of flavonoids has been described only for taxifolin and quercetin.…”

Section: Introductionmentioning

confidence: 99%

Selectively Halogenated Flavonolignans—Preparation and Antibacterial Activity

Hurtová

Káňová

Dobiasová

et al. 2022

IJMS

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A library of previously unknown halogenated derivatives of flavonolignans (silybins A and B, 2,3-dehydrosilybin, silychristin A, and 2,3-dehydrosilychristin A) was prepared. The effect of halogenation on the biological activity of flavonolignans was investigated. Halogenated derivatives had a significant effect on bacteria. All prepared derivatives inhibited the AI-2 type of bacterial communication (quorum sensing) at concentrations below 10 µM. All prepared compounds also inhibited the adhesion of bacteria (Staphyloccocus aureus and Pseudomonas aeruginosa) to the surface, preventing biofilm formation. These two effects indicate that the halogenated derivatives are promising antibacterial agents. Moreover, these derivatives acted synergistically with antibiotics and reduced the viability of antibiotic-resistant S. aureus. Some flavonolignans were able to reverse the resistant phenotype to a sensitive one, implying that they modulate antibiotic resistance.

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2,3-Dehydroderivatives of Silymarin Flavonolignans: Prospective Natural Compounds for the Prevention of Chronic Diseases

Cited by 4 publications

References 15 publications

Antioxidant, Anti-Inflammatory, and Multidrug Resistance Modulation Activity of Silychristin Derivatives

Antioxidant, Anti-Inflammatory, and Multidrug Resistance Modulation Activity of Silychristin Derivatives

Preparation of Retinoyl-Flavonolignan Hybrids and Their Antioxidant Properties

Selectively Halogenated Flavonolignans—Preparation and Antibacterial Activity

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