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2,3-Dehydrosilybin (DHS) was previously shown to chelate and reduce both copper and iron ions. In this study, similar experiments with 2,3-dehydrosilychristin (DHSCH) showed that this congener of DHS also chelates and reduces both metals. Statistical analysis pointed to some differences between both compounds: in general, DHS appeared to be a more potent iron and copper chelator, and a copper reducing agent under acidic conditions, while DHSCH was a more potent copper reducing agent under neutral conditions. In the next step, both DHS and DHSCH were tested for metal-based Fenton chemistry in vitro using HPLC with coulometric detection. Neither of these compounds were able to block the iron-based Fenton reaction and, in addition, they mostly intensified hydroxyl radical production. In the copper-based Fenton reaction, the effect of DHSCH was again prooxidant or neutral, while the effect of DHS was profoundly condition-dependent. DHS was even able to attenuate the reaction under some conditions. Interestingly, both compounds were strongly protective against the copper-triggered lysis of red blood cells, with DHSCH being more potent. The results from this study indicated that, notwithstanding the prooxidative effects of both dehydroflavonolignans, their in vivo effect could be protective.

Silybum marianum (L.) Gaertn. (aka milk thistle) constitutes the source of silymarin (SILM), a mixture of different flavonolignans and represents a unique model for their extraction. Here we report on the development and validation of an ultrasound-assisted extraction (UAE) method of S. marianum flavonolignans follow by their quantification using LC system. The optimal conditions of this UAE method were: aqueous EtOH 54.5% (v/v) as extraction solvent, with application of an ultrasound (US) frequency of 36.6 kHz during 60 min at 45 °C with a liquid to solid ratio of 25:1 mL/g dry weight (DW). Following its optimization using a full factorial design, the extraction method was validated according to international standards of the association of analytical communities (AOAC) to ensure precision and accuracy in the quantitation of each component of the SILM mixture. The efficiency of this UAE was compared with maceration protocol. Here, the optimized and validated conditions of the UAE allowed the highest extraction yields of SILM and its constituents in comparison to maceration. During UAE, the antioxidant capacity of the extracts was retained, as confirmed by the in vitro assays CUPRAC (cupric ion reducing antioxidant capacity) and inhibition of AGEs (advanced glycation end products). The skin anti-aging potential of the extract obtained by UAE was also confirmed by the strong in vitro cell-free inhibition capacity of both collagenase and elastase. To summarize, the UAE procedure presented here is a green and efficient method for the extraction and quantification of SILM and its constituents from the fruits of S. marianum, making it possible to generate extracts with attractive antioxidant and anti-aging activities for future cosmetic applications.

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.

2,3-Dehydrosilybin (DHS) was previously shown to chelate and reduce both copper and iron ions. In this study, similar experiments with 2,3-dehydrosilychristin (DHSCH) showed that this congener of DHS also chelates and reduces both metals. Statistical analysis pointed to some differences between both compounds: in general, DHS appeared to be a more potent iron and copper chelator, and a copper reducing agent under acidic conditions, while DHSCH was a more potent copper reducing agent under neutral conditions. In the next step, both DHS and DHSCH were tested for metal-based Fenton chemistry in vitro using HPLC with coulometric detection. Neither of these compounds were able to block the iron-based Fenton reaction and, in addition, they mostly intensified hydroxyl radical production. In the copper-based Fenton reaction, the effect of DHSCH was again prooxidant or neutral, while the effect of DHS was profoundly condition-dependent. DHS was even able to attenuate the reaction under some conditions. Interestingly, both compounds were strongly protective against the copper-triggered lysis of red blood cells, with DHSCH being more potent. The results from this study indicated that, notwithstanding the prooxidative effects of both dehydroflavonolignans, their in vivo effect could be protective. [ABSTRACT FROM AUTHOR]

Silybum marianum (L.) Gaertn. (aka milk thistle) constitutes the source of silymarin (SILM), a mixture of different flavonolignans and represents a unique model for their extraction. Here we report on the development and validation of an ultrasound-assisted extraction (UAE) method of S. marianum flavonolignans follow by their quantification using LC system. The optimal conditions of this UAE method were: aqueous EtOH 54.5% (v/v) as extraction solvent, with application of an ultrasound (US) frequency of 36.6 kHz during 60 min at 45 °C with a liquid to solid ratio of 25:1 mL/g dry weight (DW). Following its optimization using a full factorial design, the extraction method was validated according to international standards of the association of analytical communities (AOAC) to ensure precision and accuracy in the quantitation of each component of the SILM mixture. The efficiency of this UAE was compared with maceration protocol. Here, the optimized and validated conditions of the UAE allowed the highest extraction yields of SILM and its constituents in comparison to maceration. During UAE, the antioxidant capacity of the extracts was retained, as confirmed by the in vitro assays CUPRAC (cupric ion reducing antioxidant capacity) and inhibition of AGEs (advanced glycation end products). The skin anti-aging potential of the extract obtained by UAE was also confirmed by the strong in vitro cell-free inhibition capacity of both collagenase and elastase. To summarize, the UAE procedure presented here is a green and efficient method for the extraction and quantification of SILM and its constituents from the fruits of S. marianum, making it possible to generate extracts with attractive antioxidant and anti-aging activities for future cosmetic applications. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]