Phenolic profile and in vitro antioxidant power of different milk thistle [Silybum marianum (L.) Gaertn.] cultivars

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.

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Anti-Glycation Activities of Phenolic Constituents from Silybum marianum (Milk Thistle) Flower in Vitro and on Human Explants

Molecules ◽

10.3390/molecules20033549 ◽

2015 ◽

Vol 20 (3) ◽

pp. 3549-3564 ◽

Cited By ~ 12

Author(s):

Seoungwoo Shin ◽

Jung-A Lee ◽

Minkyung Kim ◽

Hyunwoo Kum ◽

Eunsun Jung ◽

...

Keyword(s):

Milk Thistle ◽

Silybum Marianum ◽

Phenolic Constituents ◽

Human Explants

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Ocimum basilicum L.: Phenolic Profile and Antioxidant-related Activity

Natural Product Communications ◽

10.1177/1934578x1000500117 ◽

2010 ◽

Vol 5 (1) ◽

pp. 1934578X1000500 ◽

Cited By ~ 1

Author(s):

H.J. Damien Dorman ◽

Raimo Hiltunen

Keyword(s):

Radical Scavenging ◽

Ocimum Basilicum ◽

In Vitro Assays ◽

Related Activity ◽

Phenolic Profile ◽

Antioxidant Power ◽

Liquid Liquid Extraction ◽

Ferric Reducing Antioxidant Power ◽

Free Radical Scavenging Activities

Ocimum basilicum L. leaf material was extracted by maceration with (80:20:1 v/v/v) methanol: water: acetic acid to produce a crude extract (CE), which was further fractionated by liquid-liquid extraction to isolate light petroleum (PE), ethyl acetate (EtOAc), n-butanol (n-BuOH) and H2O-soluble subfractions. The total phenol and flavonoid contents of the resulting samples were estimated using colorimetric-based methods, and their iron(III) reductive and free radical scavenging activities were determined in a battery of in vitro assays. The CE and subfractions contained phenolic compounds and flavonoids. The samples, except for PE, gave a positive result for the presence of flavones and flavonols; however, flavanones only appeared to be present in the CE. In iron(III) reduction, CE and n-BuOH were the most potent followed by EtOAc and H2O (statistically indistinguishable, p > 0.05). However, in the ferric reducing antioxidant power assay, H2O was the most potent followed by CE and EtOAc (statistically indistinguishable, p > 0.05) and n-BuOH and PE. In 1,1-diphenyl-2-picrylhydrazyl scavenging, all the samples, except PE, were effective against this reactive nitrogen species, with CE, EtOAc and n-BuOH being the most potent (statistically indistinguishable, p > 0.05). In alkylperoxyl scavenging, all the samples, except for PE, were effective against this reactive oxygen species (ROS). In superoxide anion scavenging, all the samples were capable of scavenging this ROS with CE being the most effective, followed by n-BuOH and H2O (statistically indistinguishable, p > 0.05) and EtOAc and PE. Similarly, in hydroxyl scavenging, all the samples were capable of scavenging this ROS with CE and n-BuOH being the most effective (statistically indistinguishable, p > 0.05) followed by EtOAc and H2O (statistically indistinguishable, p > 0.05) and PE.

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Antifungal Activity against Botryosphaeriaceae Fungi of the Hydro-Methanolic Extract of Silybum marianum Capitula Conjugated with Stevioside

Plants ◽

10.3390/plants10071363 ◽

2021 ◽

Vol 10 (7) ◽

pp. 1363

Author(s):

Natalia Langa-Lomba ◽

Laura Buzón-Durán ◽

Eva Sánchez-Hernández ◽

Pablo Martín-Ramos ◽

José Casanova-Gascón ◽

...

Keyword(s):

Plant Protection ◽

Fungal Species ◽

Added Value ◽

Milk Thistle ◽

Phytochemical Analysis ◽

Silybum Marianum ◽

Methanolic Extracts ◽

Botryosphaeria Dieback

Silybum marianum (L.) Gaertn, viz. milk thistle, has been the focus of research efforts in the past few years, albeit almost exclusively restricted to the medicinal properties of its fruits (achenes). Given that other milk thistle plant organs and tissues have been scarcely investigated for the presence of bioactive compounds, in this study, we present a phytochemical analysis of the extracts of S. marianum capitula during the flowering phenological stage (stage 67). Gas chromatography–mass spectroscopy results evidenced the presence of high contents of coniferyl alcohol (47.4%), and secondarily of ferulic acid ester, opening a new valorization strategy of this plant based on the former high-added-value component. Moreover, the application of the hydro-methanolic extracts as an antifungal agent has been also explored. Specifically, their activity against three fungal species responsible for the so-called Botryosphaeria dieback of grapevine (Neofusicoccum parvum, Dothiorella viticola and Diplodia seriata) has been assayed both in vitro and in vivo. From the mycelial growth inhibition assays, the best results (EC90 values of 303, 366, and 355 μg·mL−1 for N. parvum, D. viticola, and D. seriata, respectively) were not obtained for the hydroalcoholic extract alone, but after its conjugation with stevioside, which resulted in a strong synergistic behavior. Greenhouse experiments confirmed the efficacy of the conjugated complexes, pointing to the potential of the combination of milk thistle extracts with stevioside as a promising plant protection product in organic Viticulture.

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A Green Ultrasound-Assisted Extraction Optimization of the Natural Antioxidant and Anti-aging Flavonolignans from Milk Thistle Silybum marianum (L.) Gaertn. Fruits for Cosmetic Applications

10.20944/preprints201907.0252.v1 ◽

2019 ◽

Author(s):

Samantha Drouet ◽

Emilie Leclerc ◽

Laurine Garros ◽

Duangjai Tungmunnithum ◽

Atul Kabra ◽

...

Keyword(s):

International Standards ◽

Milk Thistle ◽

Silybum Marianum ◽

Ultrasound Assisted Extraction ◽

Solid Ratio ◽

Ultrasound Frequency ◽

Assisted Extraction ◽

Ultrasound Assisted ◽

The Individual

Silybum marianum (L.) Gaertn. (aka milk thistle) constitute the almost exclusive source of silymarin, a mixture of different flavonolignans, and is thus considered as a unique model for their extraction. The present research deals with ultrasound-assisted extraction (UAE) of S. marianum flavonolignans and their quantification using LC system. The optimal conditions for UAE were: aqueous EtOH 54.5% (v/v) as solvent, applying an ultrasound frequency of 36.6 kHz during an extraction time of 60 min at 45°C with a liquid to solid ratio of 25:1 ml/g DW. Following optimization, the extraction method was validated according to international standards of the association of analytical communities (AOAC) in order to ensure its precision and accuracy for the quantitation of the individual silymarin components. The efficiency of UAE was compared with maceration protocol of the same duration. The optimized and validated conditions allowed highest extraction yields of flavonolignans in comparison to maceration. The antioxidant capacity of the extracts was confirmed by the CUPRAC assays and inhibition of advanced glycation end products. The skin anti-aging action was also confirmed toward the strong in vitro inhibition capacity of the obtained extract against collagenase and elastase enzymes. The procedure presented here allows a green efficient extraction and quantification of the main flavonolignans from the fruits of S. marianum with attractive antioxidant and anti-aging activities for future cosmetic applications.

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The pathogen of Milk Thistle (Silybum marianum (L.) Gaertn.) in the Czech Republic

JOURNAL OF ADVANCES IN AGRICULTURE ◽

10.24297/jaa.v5i1.4264 ◽

2015 ◽

Vol 5 (1) ◽

pp. 538-544

Author(s):

Ivana Safrankova ◽

Kolackova P ◽

Rutivckova G

Keyword(s):

Czech Republic ◽

Environmental Factors ◽

Active Compound ◽

Fungal Species ◽

Medicinal Herb ◽

Milk Thistle ◽

Silybum Marianum ◽

The Czech Republic

Milk thistle is grown in the Czech Republic as a medicinal herb; silymarin is isolated from its achenes and used for the production of liver and gallbladder medicine. The quality and content of the active compound is influenced not only by environmental factors, but also by pests and pathogens. The occurrence of pests of milk thistle variety Silyb was observed in two localities during the years 2011 2013. In the year 2011 the mycoflora of seeds of four milk thistle varieties was determined. Representatives of 15 species were isolated from the seeds, most of them saprophytic. 21 fungal species were isolated and identified from milk thistle plants during the vegetation; Septoria silybi among the most important ones. Possibilities of protection of milt thistle against pathogens are discussed.

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A COMPARATIVE STUDY OF STANDARDIZATION METHODS FOR THE MILK THISTLE FRUIT (SILYBUM MARIANUM)

University proceedings Volga region Medical sciences ◽

10.21685/2072-3032-2016-4-4 ◽

2016 ◽

Author(s):

S. A. Burkush ◽

◽

S. V. Chizhov ◽

N. V. Firstova ◽

N. N. Glebova ◽

...

Keyword(s):

Comparative Study ◽

Milk Thistle ◽

Silybum Marianum ◽

Standardization Methods

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Extraction, Chemical Composition, Antioxidant Property and In vitro Anticancer Activity of Silymarin from Silybum Marianum On Kb and A549 Cell Lines

Current Drug Discovery Technologies ◽

10.2174/1570163817666200827111127 ◽

2020 ◽

Vol 17 ◽

Author(s):

Mojgan Azadpour ◽

Mohammad Mehdi Farajollahi ◽

Ali Mohammad Varzi ◽

Pejman Hashemzadeh ◽

Hossein Mahmoudvand ◽

...

Keyword(s):

Anticancer Activity ◽

Cell Lines ◽

A549 Cell ◽

Hplc Analysis ◽

Antioxidant Properties ◽

Radical Scavenging ◽

Antioxidant Property ◽

Silybum Marianum ◽

Stable Free Radical

Introduction: This study aimed to evaluate the antioxidant property of silymarin (SM) extracted from the seed of Silybum marianum and its anticancer activity on KB and A549 cell lines following 24, 48, and 72 h of treatment. Methods: Ten grams of powdered S. marianum seeds were defatted using n-hexane for 6 hours and then extracted by methanol. The silymarin extracted of extraction components The extracted components of silymarin were measured by spectrophotometric assay and HPLC analysis. 2, 2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, phenol content, total flavonoid content, and total antioxidant capacity were measured to detect the antioxidant properties of SM. The anticancer activity of the SM on cell lines evaluated by MTT. Results: In HPLC analysis, more than 50% of the peaks were related to silibin A and B. SM was reducedDPPH (the stable free radical) with a 50% inhibitory concentration (IC50) of 6.56 μg/ ml in comparison with butylated hydroxyl toluene (BHT), which indicated an IC50 of ~3.9 μg/ ml.The cytotoxicity effect of SM on the cell lines was studied by MTT assay. The cytotoxicity effect of the extracted silymarin on KB and A549 cell lines was observed up to 80 and 70% at 156 and 78 µg/ml, respectively. The IC50 value of the extracted SM on KB and A549 cell lines after 24 hours of treatment was seen at 555 and 511 µg/ml, respectively. Conclusion: Due to the good antioxidant and anticancer properties of the isolated silymarin, its use as an anticancer drug is suggested.

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Synthesis and antioxidant activity of new selenium-containing quinolines

Medicinal Chemistry ◽

10.2174/1573406416666200403081831 ◽

2020 ◽

Vol 16 ◽

Cited By ~ 1

Author(s):

Benedetta Bocchini ◽

Bruna Goldani ◽

Fernanda S.S. Sousa ◽

Paloma T. Birmann ◽

Cesar A. Brüning ◽

...

Keyword(s):

Antioxidant Activity ◽

Superoxide Dismutase ◽

Radical Scavenging ◽

Building Blocks ◽

Antioxidant Potential ◽

In Vitro Assays ◽

Pharmacological Activities ◽

Antioxidant Power ◽

Antioxidant Agents

Background: Quinoline derivatives have been attracted much attention in drug discovery and synthetic derivatives of these scaffolds present a range of pharmacological activities. Therefore, organoselenium compounds are valuable scaffolds in organic synthesis because their pharmacological activities and their use as versatile building blocks for regio-, chemio-and stereoselective reactions. Thus, the synthesis of selenium-containing quinolines has great significance, and their applicability range from simple antioxidant agents, to selective DNA-binding and photocleaving agents. Objective: In the present study we describe the synthesis and antioxidant activity in vitro of new 7-chloroN(arylselanyl)quinolin-4-amines 5 by the reaction of 4,7-dichloroquinoline 4 with (arylselanyl)-amines 3. Methods: For the synthesis of 7-chloro-N(arylselanyl)quinolin-4-amines 5, we performed the reaction of (arylselanyl)- amines 3 with 4,7-dichloroquinoline 4 in the presence of Et3N at 120 °C in a sealed tube. The antioxidant activities of the compounds 5 were evaluated by the following in vitro assays: 2,2- diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, 2,2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric ion reducing antioxidant power (FRAP), nitric oxide (NO) scavenging and superoxide dismutase-like activity (SOD-Like). Results: 7-Chloro-N(arylselanyl)quinolin-4-amines 5a-d has been synthesized in yields ranging from 68% to 82% by the reaction of 4,7-dichloroquinoline 4 with arylselanyl-amines 3a-d using Et3N as base, at 120 °C, in a sealed tube for 24 hours and tolerates different substituents, such as -OMe and -Cl, in the arylselanyl moiety. The obtained compounds 5a-d presented significant results with respect to the antioxidant potential, which had effect in the tests of inhibition of radical’s DPPH, ABTS+ and NO, as well as in the test that evaluates the capacity (FRAP) and in the superoxide dismutase-like activity assay (SOD-Like). It is worth mentioning that 7-chloro-N(arylselanyl)quinolin-4-amine 5b presented excellent results, demonstrating a better antioxidant capacity when compared to the others. Conclusion: According to the obtained results 7-chloro-N(arylselanyl)quinolin-4-amines 5 were synthesized in good yields by the reaction of 4,7-dichloroquinoline with arylselanyl-amines and tolerates different substituents in the arylselanyl moiety. The tested compounds presented significant antioxidant potential in the tests of inhibition of DPPH, ABTS+ and NO radicals, as well as in the FRAP and superoxide dismutase-like activity assays (SOD-Like).

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Phytochemicals of Minthostachys diffusa Epling and Their Health-Promoting Bioactivities

Foods ◽

10.3390/foods9020144 ◽

2020 ◽

Vol 9 (2) ◽

pp. 144

Author(s):

Immacolata Faraone ◽

Daniela Russo ◽

Lucia Chiummiento ◽

Eloy Fernandez ◽

Alka Choudhary ◽

...

Keyword(s):

Ethyl Acetate ◽

Radical Scavenging ◽

Ethyl Acetate Fraction ◽

Mass Spectrometry Analysis ◽

Antioxidant Power ◽

Spectrometry Analysis ◽

In Silico Docking ◽

Aerial Parts ◽

Health Promoting

The genus Minthostachys belonging to the Lamiaceae family, and is an important South American mint genus used commonly in folk medicine as an aroma in cooking. The phytochemical-rich samples of the aerial parts of Minthostachys diffusa Epling. were tested for pharmacological and health-promoting bioactivities using in vitro chemical and enzymatic assays. A range of radical scavenging activities of the samples against biological radicals such as nitric oxide and superoxide anion and against synthetic 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radicals, the ferric reducing antioxidant power and the lipid peroxidation inhibition were determined and ranked using the ‘relative antioxidant capacity index’ (RACI). The ethyl acetate fraction showed the highest RACI of +1.12. Analysis of the various fractions’ inhibitory ability against enzymes involved in diabetes (α-amylase and α-glucosidase), and against enzymes associated with Parkinson’s or Alzheimer’s diseases (acetylcholinesterase and butyrylcholinesterase) also suggested that the ethyl acetate fraction was the most active. Liquid chromatography–tandem mass spectrometry analysis of the ethyl acetate fraction showed more than 30 polyphenolic compounds, including triterpenes. The inhibitory cholinesterase effects of the triterpenes identified from M. diffusa were further analysed by in silico docking of these compounds into 3D-structures of acetylcholinesterase and butyrylcholinesterase. This is the first study on pharmacological activities and phytochemical profiling of the aerial parts of M. diffusa, showing that this plant, normally used as food in South America, is also rich in health-promoting phytochemicals.

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