Silybum mariamum （L.）Gaertrn.
Silicristin/Silicristinum/(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one/Silicristinum [INN-Latin]/Silicristina/(2R,3R)-3,5,7-Trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydro-4H-chromen-4-one/Silicristina [INN-Spanish]/4H-1-Benzopyran-4-one, 2-[(2R,3S)-2,3-dihydro-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranyl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-/Silychristin/Silymarin II/Silicristine [INN-French]/(2R,3R)-3,5,7-trihydroxy-2-[(2R,3S)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzofuran-5-yl]chroman-4-one/Silicristine
Silychristin is an abundant flavonolignan present in the fruits of Silybum marianum, with antioxidant properties. Silychristin is a potent inhibitor of the thyroid hormone transporter MCT8, and elicits a strong inhibition of T3 uptake with an IC50 of 110 nM.
Methanol; Ethyl Acetate
782.0±60.0 °C at 760 mmHg
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The exposure of naked unprotected skin to solar radiation may result in numerous acute and chronic undesirable effects. Evidence suggests that silymarin, a standardized extract from Silybum marianum (L.) Gaertn. seeds, and its major component silybin suppress UVB-induced skin damage. Here, we aimed to investigate the UVA-protective effects of silymarin’s less abundant flavonolignans, specifically isosilybin (ISB), silychristin (SC), silydianin (SD), and 2,3-dehydrosilybin (DHSB). Normal human dermal fibroblasts (NHDF) pre-treated for 1 h with flavonolignans were then exposed to UVA light using a solar simulator. Their effects on reactive oxygen species (ROS), carbonylated proteins and glutathione (GSH) level, caspase-3 activity, single-strand breaks’ (SSBs) formation and protein level of matrix metalloproteinase-1 (MMP-1), heme oxygenase-1 (HO-1), and heat shock protein (HSP70) were evaluated. The most pronounced preventative potential was found for DHSB, a minor component of silymarin, and SC, the second most abundant flavonolignan in silymarin. They had significant effects on most of the studied parameters. Meanwhile, a photoprotective effect of SC was mostly found at double the concentration of DHSB. ISB and SD protected against GSH depletion, the generation of ROS, carbonylated proteins and SSBs, and caspase-3 activation, but had no significant effect on MMP-1, HO-1, or HSP70. In summary, DHSB and to a lesser extent other silymarin flavonolignans are potent UVA-protective compounds. However, due to the in vitro phototoxic potential of DHSB published elsewhere, further studies are needed to exclude phototoxicity for humans as well as to confirm our results on human skin ex vivo and in vivo.
Cell culture; Flavonolignan; Heat shock protein; Metalloproteinase-1; Oxidative damage; UVA
A pilot study of the UVA-photoprotective potential of dehydrosilybin, isosilybin, silychristin, and silydianin on human dermal fibroblasts.
Rajnochova Svobodova A1, Gabrielova E1, Ulrichova J1, Zale?ak B2, Biedermann D3, Vostalova J4.
1. Silymarin refers to a class of flavonoid lignans occurring in the fruits and seeds of the Silybum manalttlm (L). Gaertn, and is widely used in dietary supplements. 2. The main active ingredients of silymarin are silychristins A and B, silydianin, silybins A and B, and isosilybins A and B. However, the metabolism of silymarin has never been investigated. The major objectives of the present study were to investigate the metabolic pathways of silymarin isomers and to identify reactive metabolites. 3. Fourteen glutathione (GSH) conjugates were detected in rat/human liver microsomes incubations containing NADPH, GSH and seven individual isomers. Seven GSH conjugates (M1-M7) resulted from demethylated silymarin. M8-M14 originated from hydroxylated silymarin. Moreover, we found that GSH was probably conjugated on either ring A or ring E of silymarin based on the mass spectrometric fragments. In addition, recombinant enzyme incubation experiments demonstrated that CYP3A4 was the predominant P450 responsible for the metabolism of silymarin. 4. Several P450 enzymes were reportedly inactivated by some of bioactive constituents of silymarin to some extent. Our findings facilitate the understanding of mechanisms of the reported inactivation of P450 enzymes induced by silymarin.
P450; Silymarin isomers; bioactivation; glutathione conjugates; metabolite profile
Characterization of glutathione conjugates derived from reactive metabolites of seven silymarin isomers.
Chen Y1, Yu J1, Wang X1, Li H1, Mao X1, Peng Y1, Zheng J2,3,1.
Mesocestoides vogae larvae represent a suitable model for evaluating the larvicidal potential of various compounds. In this study we investigated the in vitro effects of three natural flavonolignans-silybin (SB), 2,3-dehydrosilybin (DHSB) and silychristin (SCH)-on M. vogae larvae at concentrations of 5 and 50 μM under aerobic and hypoxic conditions for 72 h. With both kinds of treatment, the viability and motility of larvae remained unchanged, metabolic activity, neutral red uptake and concentrations of neutral lipids were reduced, in contrast with a significantly elevated glucose content. Incubation conditions modified the effects of individual FLs depending on their concentration. Under both sets of conditions, SB and SCH suppressed metabolic activity, the concentration of glucose, lipids and partially motility more at 50 μM, but neutral red uptake was elevated. DHSB exerted larvicidal activity and affected motility and neutral lipid concentrations differently depending on the cultivation conditions, whereas it decreased glucose concentration. DHSB at the 50 μM concentration caused irreversible morphological alterations along with damage to the microvillus surface of larvae, which was accompanied by unregulated neutral red uptake. In conclusion, SB and SCH suppressed mitochondrial functions and energy stores, inducing a physiological misbalance, whereas DHSB exhibited a direct larvicidal effect due to damage to the tegument and complete disruption of larval physiology and metabolism.
2,3-dehydrosilybin; Mesocestoides vogae larvae; aerobic and hypoxic cultivation; silybin; silychristin
Differential Effects of the Flavonolignans Silybin, Silychristin and 2,3-Dehydrosilybin on Mesocestoides vogae Larvae (Cestoda) under Hypoxic and Aerobic In Vitro Conditions.
Hrckova G1, Kuba?kova TM2, Benada O3, Kofro?ova O4, Tumova L5, Biedermann D6.
2018 Nov 16;