Verbascoside

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Vicente Micol - One of the best experts on this subject based on the ideXlab platform.

  • phenylpropanoids and their metabolites are the major compounds responsible for blood cell protection against oxidative stress after administration of lippia citriodora in rats
    Phytomedicine, 2013
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Maria Herranzlopez, Isabel Borraslinares, Alberto Fernandezgutierrez
    Abstract:

    Lippia citriodora (lemon verbena) has been widely used in folk medicine for its pharmacological properties. Verbascoside, the most abundant compound in this plant, has protective effects associated mostly with its strong antioxidant activity. The purpose of this study was to test the effect of L. citriodora extract intake on the antioxidant response of blood cells and to correlate this response with the phenolic metabolites found in plasma. For this purpose, firstly the L. citriodora extract was characterized and its radical scavenging activity was measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Then, catalase (CAT), glutathione peroxidase (GPx), and glutathione reductase (GRed) activities were determined in lymphocytes, erythrocytes, and neutrophils isolated from rats after acute intake of L. citriodora. Phenolic metabolites were analyzed in the same plasma samples by HPLC-ESI-TOF-MS. Myeloperoxidase (MPO) activity in neutrophils, which has been proposed as a marker for inflammatory vascular damage, was also determined. After L. citriodora administration, the antioxidant enzymes activities significantly accelerated (p<0.05) while MPO activity subsided, indicating that the extract protects blood cells against oxidative damage and shows potential anti-inflammatory and antiatherogenic activities. The main compounds found in plasma were Verbascoside and isoVerbascoside at a concentration of 80±10 and 57±4 ng/ml, respectively. Five other metabolites derived from Verbascoside and isoVerbascoside were also found in plasma, namely hydroxytyrosol, caffeic acid, ferulic acid, ferulic acid glucuronide, and homoprotocatechuic acid, together with another eight phenolic compounds. Therefore, the phenylpropanoids Verbascoside and isoVerbascoside, as well as their metabolites, seem to be the responsible for the above-mentioned effects, although the post-transcriptional activation mechanism of blood-cell antioxidant enzymes by these compounds needs further investigation.

  • effects of Verbascoside a phenylpropanoid glycoside from lemon verbena on phospholipid model membranes
    Chemistry and Physics of Lipids, 2010
    Co-Authors: Lorena Funes, Olga Laporta, Manuela Cerdancalero, Vicente Micol
    Abstract:

    Phenylpropanoid glycosides are water-soluble compounds widely distributed, most of them deriving from medicinal herbs. Among them, Verbascoside or acteoside has exhibited a wide biological activity, being free radical scavenging the most representative one. Moreover, antitumor, antimicrobial, anti-inflammatory, anti-thrombotic and wound healing properties have been previously described. Herein, the interaction of Verbascoside with phospholipid membranes has been studied by means of differential scanning calorimetry, fluorescence anisotropy and dynamic light scattering. Verbascoside showed stronger affinity for negatively charged membranes composed of phosphatidylglycerol (PG) than for phosphatidylcholine (PC) membranes. This compound promoted phase separation of lipid domains in PC membranes and formed a stable lipid complex with and approximate phospholipid/Verbascoside ratio of 4:1. Despite its hydrophilic character, Verbascoside's caffeoyl moiety was located deep into the hydrophobic core of PC membranes and was almost inaccessible to spin probes located at different depths in PG membranes. This compound affected the ionization behavior of the PG phosphate group and most likely interacted with the vesicles surface. The presence of Verbascoside decreased the particle size in PG unilamellar vesicles through the increase of the phospholipid head group area. A localization of Verbascoside filling the upper region of PG bilayers close to the phospholipid/water interface is proposed. These effects on membranes may help to understand the mechanism of the biological activity of Verbascoside and other similar phenylpropanoid glycosides.

  • Correlation between plasma antioxidant capacity and Verbascoside levels in rats after oral administration of lemon verbena extract
    Food Chemistry, 2009
    Co-Authors: Lorena Funes, Salvador Fernández-arroyo, Olga Laporta, Antoni Pons, Enrique Roche, Antonio Segura-carretero, Alberto Fernández-gutiérrez, Vicente Micol
    Abstract:

    Phenylpropanoids are the main class of compounds from lemon verbena which have shown a wide biological activity, Verbascoside being the most abundant one. In this work, the composition of a lemon verbena extract was elucidated by HPLC-ESI-MS/MS and one flavone and one methoxylated phenylpropanoid were found in this source for the first time. The antioxidant activity of the lemon verbena extract was fully characterised by several methodologies. Unexpectedly, the extract was especially active in lipophilic environments and lipid peroxidation inhibition assay, as it was found for pure Verbascoside. The lemon verbena extract, containing Verbascoside as its major bioactive compound, was acutely administered to rats and Verbascoside was the only metabolite detected in plasma samples as measured by HPLC mass spectrometry. The correlation between the highest Verbascoside concentration in plasma and maximum plasma antioxidant capacity was observed at 20 min as measured by different techniques, i.e. minimum malondialdehyde (MDA) generation, highest ferric-reducing ability of plasma (FRAP value) and maximum superoxide dismutase activity (SOD). Therefore, the in vitro measurements of the antioxidant activity of lemon verbena extract may significantly support the antioxidant activity observed in vivo in this work. Moreover, neither evidence of acute oral toxicity nor adverse effects were observed in mice when the lemon verbena extract containing 25% Verbascoside was used at a dosage of 2000 mg/kg.

  • high performance liquid chromatography with diode array detection coupled to electrospray time of flight and ion trap tandem mass spectrometry to identify phenolic compounds from a lemon verbena extract
    Journal of Chromatography A, 2009
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Alberto Fernandezgutierrez
    Abstract:

    Abstract High-performance liquid chromatography with diode array and electrospray ionization mass spectrometric detection was used to carry out the comprehensive characterization of a lemon verbena extract with demonstrated antioxidant and antiinflammatory activity. Two different MS techniques have been coupled to HPLC: on one hand, time-of-flight mass spectrometry, and on the other hand, tandem mass spectrometry on an ion-trap. The use of a small particle size C18 column (1.8 μm) provided a great resolution and made possible the separation of several isomers. The UV–visible spectrophotometry was used to delimit the class of phenolic compound and the accurate mass measurements on time-of-flight spectrometer enabled to identify the compounds present in the extract. Finally, the fragmentation pattern obtained in MS–MS experiments confirmed the proposed structures. This procedure was able to determine many well-known phenolic compounds present in lemon verbena such as Verbascoside and its derivatives, diglucuronide derivatives of apigenin and luteolin, and eukovoside. Also gardoside, verbasoside, cistanoside F, theveside, campneoside I, chrysoeriol-7-diglucuronide, forsythoside A and acacetin-7-diglucuronide were found for the first time in lemon verbena.

Armandodoriano Bianco - One of the best experts on this subject based on the ideXlab platform.

  • reassessment of the polar fraction of stachys alopecuros l benth subsp divulsa ten grande lamiaceae from the monti sibillini national park and its potential pharmacologic uses
    Journal of Intercultural Ethnopharmacology, 2017
    Co-Authors: Alessandro Venditti, Mauro Serafini, Claudio Frezza, Lorenzo M Lorenzetti, Filippo Maggi, Armandodoriano Bianco
    Abstract:

    In this paper is reported an in deep study of the glycosidic fraction of S. alopecuros subsp. divulsa which permitted to widen the knowledge on its iridoid pattern, being constituted also by ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7), besides 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), 4′-O-galactopyranosyl-teuhircoside (5) which had been already isolated from this species. The phenolic compounds isolated during the study resulted to be chlorogenic acid (8), β-arbutin (9), Verbascoside (10) and stachysoside A (11) instead. Except for the reconfirmed Verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported and both the chemotaxonomic and pharmacologic relevance of the isolated compounds are discussed.

  • Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.
    SAGEYA, 2017
    Co-Authors: Alessandro Venditti, Mauro Serafini, Claudio Frezza, Lorenzo M Lorenzetti, Filippo Maggi, Armandodoriano Bianco
    Abstract:

    In this paper is reported an in deep study of the glycosidic fraction of S. alopecuros subsp. divulsa which permitted to widen the knowledge on its iridoid pattern, being constituted also by ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7), besides 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), 4′-O-galactopyranosyl-teuhircoside (5) which had been already isolated from this species. The phenolic compounds isolated during the study resulted to be chlorogenic acid (8), β-arbutin (9), Verbascoside (10) and stachysoside A (11) instead. Except for the reconfirmed Verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported and both the chemotaxonomic and pharmacologic relevance of the isolated compounds are discussed. [J Complement Med Res 2017; 6(2.000): 144-153

  • phytochemical composition of polar fraction of stachys germanica l subsp salviifolia ten gams a typical plant of majella national park
    Natural Product Research, 2013
    Co-Authors: Alessandro Venditti, Anna Maria Serrilli, M Di Cecco, G Ciaschetti, T Andrisano, Armandodoriano Bianco
    Abstract:

    In this study, we report the isolation and identification of several compounds present in the polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, collected in the protected area of Majella National Park. In particular, we have isolated and identified harpagide, 7 -β-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, Verbascoside and, for the first time in this genus, arbutin.

Lorena Funes - One of the best experts on this subject based on the ideXlab platform.

  • phenylpropanoids and their metabolites are the major compounds responsible for blood cell protection against oxidative stress after administration of lippia citriodora in rats
    Phytomedicine, 2013
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Maria Herranzlopez, Isabel Borraslinares, Alberto Fernandezgutierrez
    Abstract:

    Lippia citriodora (lemon verbena) has been widely used in folk medicine for its pharmacological properties. Verbascoside, the most abundant compound in this plant, has protective effects associated mostly with its strong antioxidant activity. The purpose of this study was to test the effect of L. citriodora extract intake on the antioxidant response of blood cells and to correlate this response with the phenolic metabolites found in plasma. For this purpose, firstly the L. citriodora extract was characterized and its radical scavenging activity was measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Then, catalase (CAT), glutathione peroxidase (GPx), and glutathione reductase (GRed) activities were determined in lymphocytes, erythrocytes, and neutrophils isolated from rats after acute intake of L. citriodora. Phenolic metabolites were analyzed in the same plasma samples by HPLC-ESI-TOF-MS. Myeloperoxidase (MPO) activity in neutrophils, which has been proposed as a marker for inflammatory vascular damage, was also determined. After L. citriodora administration, the antioxidant enzymes activities significantly accelerated (p<0.05) while MPO activity subsided, indicating that the extract protects blood cells against oxidative damage and shows potential anti-inflammatory and antiatherogenic activities. The main compounds found in plasma were Verbascoside and isoVerbascoside at a concentration of 80±10 and 57±4 ng/ml, respectively. Five other metabolites derived from Verbascoside and isoVerbascoside were also found in plasma, namely hydroxytyrosol, caffeic acid, ferulic acid, ferulic acid glucuronide, and homoprotocatechuic acid, together with another eight phenolic compounds. Therefore, the phenylpropanoids Verbascoside and isoVerbascoside, as well as their metabolites, seem to be the responsible for the above-mentioned effects, although the post-transcriptional activation mechanism of blood-cell antioxidant enzymes by these compounds needs further investigation.

  • effects of Verbascoside a phenylpropanoid glycoside from lemon verbena on phospholipid model membranes
    Chemistry and Physics of Lipids, 2010
    Co-Authors: Lorena Funes, Olga Laporta, Manuela Cerdancalero, Vicente Micol
    Abstract:

    Phenylpropanoid glycosides are water-soluble compounds widely distributed, most of them deriving from medicinal herbs. Among them, Verbascoside or acteoside has exhibited a wide biological activity, being free radical scavenging the most representative one. Moreover, antitumor, antimicrobial, anti-inflammatory, anti-thrombotic and wound healing properties have been previously described. Herein, the interaction of Verbascoside with phospholipid membranes has been studied by means of differential scanning calorimetry, fluorescence anisotropy and dynamic light scattering. Verbascoside showed stronger affinity for negatively charged membranes composed of phosphatidylglycerol (PG) than for phosphatidylcholine (PC) membranes. This compound promoted phase separation of lipid domains in PC membranes and formed a stable lipid complex with and approximate phospholipid/Verbascoside ratio of 4:1. Despite its hydrophilic character, Verbascoside's caffeoyl moiety was located deep into the hydrophobic core of PC membranes and was almost inaccessible to spin probes located at different depths in PG membranes. This compound affected the ionization behavior of the PG phosphate group and most likely interacted with the vesicles surface. The presence of Verbascoside decreased the particle size in PG unilamellar vesicles through the increase of the phospholipid head group area. A localization of Verbascoside filling the upper region of PG bilayers close to the phospholipid/water interface is proposed. These effects on membranes may help to understand the mechanism of the biological activity of Verbascoside and other similar phenylpropanoid glycosides.

  • Correlation between plasma antioxidant capacity and Verbascoside levels in rats after oral administration of lemon verbena extract
    Food Chemistry, 2009
    Co-Authors: Lorena Funes, Salvador Fernández-arroyo, Olga Laporta, Antoni Pons, Enrique Roche, Antonio Segura-carretero, Alberto Fernández-gutiérrez, Vicente Micol
    Abstract:

    Phenylpropanoids are the main class of compounds from lemon verbena which have shown a wide biological activity, Verbascoside being the most abundant one. In this work, the composition of a lemon verbena extract was elucidated by HPLC-ESI-MS/MS and one flavone and one methoxylated phenylpropanoid were found in this source for the first time. The antioxidant activity of the lemon verbena extract was fully characterised by several methodologies. Unexpectedly, the extract was especially active in lipophilic environments and lipid peroxidation inhibition assay, as it was found for pure Verbascoside. The lemon verbena extract, containing Verbascoside as its major bioactive compound, was acutely administered to rats and Verbascoside was the only metabolite detected in plasma samples as measured by HPLC mass spectrometry. The correlation between the highest Verbascoside concentration in plasma and maximum plasma antioxidant capacity was observed at 20 min as measured by different techniques, i.e. minimum malondialdehyde (MDA) generation, highest ferric-reducing ability of plasma (FRAP value) and maximum superoxide dismutase activity (SOD). Therefore, the in vitro measurements of the antioxidant activity of lemon verbena extract may significantly support the antioxidant activity observed in vivo in this work. Moreover, neither evidence of acute oral toxicity nor adverse effects were observed in mice when the lemon verbena extract containing 25% Verbascoside was used at a dosage of 2000 mg/kg.

  • high performance liquid chromatography with diode array detection coupled to electrospray time of flight and ion trap tandem mass spectrometry to identify phenolic compounds from a lemon verbena extract
    Journal of Chromatography A, 2009
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Alberto Fernandezgutierrez
    Abstract:

    Abstract High-performance liquid chromatography with diode array and electrospray ionization mass spectrometric detection was used to carry out the comprehensive characterization of a lemon verbena extract with demonstrated antioxidant and antiinflammatory activity. Two different MS techniques have been coupled to HPLC: on one hand, time-of-flight mass spectrometry, and on the other hand, tandem mass spectrometry on an ion-trap. The use of a small particle size C18 column (1.8 μm) provided a great resolution and made possible the separation of several isomers. The UV–visible spectrophotometry was used to delimit the class of phenolic compound and the accurate mass measurements on time-of-flight spectrometer enabled to identify the compounds present in the extract. Finally, the fragmentation pattern obtained in MS–MS experiments confirmed the proposed structures. This procedure was able to determine many well-known phenolic compounds present in lemon verbena such as Verbascoside and its derivatives, diglucuronide derivatives of apigenin and luteolin, and eukovoside. Also gardoside, verbasoside, cistanoside F, theveside, campneoside I, chrysoeriol-7-diglucuronide, forsythoside A and acacetin-7-diglucuronide were found for the first time in lemon verbena.

Alessandro Venditti - One of the best experts on this subject based on the ideXlab platform.

  • reassessment of the polar fraction of stachys alopecuros l benth subsp divulsa ten grande lamiaceae from the monti sibillini national park and its potential pharmacologic uses
    Journal of Intercultural Ethnopharmacology, 2017
    Co-Authors: Alessandro Venditti, Mauro Serafini, Claudio Frezza, Lorenzo M Lorenzetti, Filippo Maggi, Armandodoriano Bianco
    Abstract:

    In this paper is reported an in deep study of the glycosidic fraction of S. alopecuros subsp. divulsa which permitted to widen the knowledge on its iridoid pattern, being constituted also by ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7), besides 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), 4′-O-galactopyranosyl-teuhircoside (5) which had been already isolated from this species. The phenolic compounds isolated during the study resulted to be chlorogenic acid (8), β-arbutin (9), Verbascoside (10) and stachysoside A (11) instead. Except for the reconfirmed Verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported and both the chemotaxonomic and pharmacologic relevance of the isolated compounds are discussed.

  • Reassessment of the polar fraction of Stachys alopecuros (L.) Benth. subsp. divulsa (Ten.) Grande (Lamiaceae) from the Monti Sibillini National Park and its potential pharmacologic uses.
    SAGEYA, 2017
    Co-Authors: Alessandro Venditti, Mauro Serafini, Claudio Frezza, Lorenzo M Lorenzetti, Filippo Maggi, Armandodoriano Bianco
    Abstract:

    In this paper is reported an in deep study of the glycosidic fraction of S. alopecuros subsp. divulsa which permitted to widen the knowledge on its iridoid pattern, being constituted also by ajugoside (1), reptoside (6) and 6-O-acetyl-ajugol (7), besides 8-O-acetylharpagide (2), harpagide (3), allobetonicoside (4), 4′-O-galactopyranosyl-teuhircoside (5) which had been already isolated from this species. The phenolic compounds isolated during the study resulted to be chlorogenic acid (8), β-arbutin (9), Verbascoside (10) and stachysoside A (11) instead. Except for the reconfirmed Verbascoside (10), the other phenolic compounds were recognized for the first time in the studied species. The complete NMR assignment of compound (1) by means of bidimensional techniques is reported and both the chemotaxonomic and pharmacologic relevance of the isolated compounds are discussed. [J Complement Med Res 2017; 6(2.000): 144-153

  • phytochemical composition of polar fraction of stachys germanica l subsp salviifolia ten gams a typical plant of majella national park
    Natural Product Research, 2013
    Co-Authors: Alessandro Venditti, Anna Maria Serrilli, M Di Cecco, G Ciaschetti, T Andrisano, Armandodoriano Bianco
    Abstract:

    In this study, we report the isolation and identification of several compounds present in the polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, collected in the protected area of Majella National Park. In particular, we have isolated and identified harpagide, 7 -β-hydroxy-harpagide, ajugol, 5-allosyloxy-aucubin, Verbascoside and, for the first time in this genus, arbutin.

Alberto Fernandezgutierrez - One of the best experts on this subject based on the ideXlab platform.

  • phenylpropanoids and their metabolites are the major compounds responsible for blood cell protection against oxidative stress after administration of lippia citriodora in rats
    Phytomedicine, 2013
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Maria Herranzlopez, Isabel Borraslinares, Alberto Fernandezgutierrez
    Abstract:

    Lippia citriodora (lemon verbena) has been widely used in folk medicine for its pharmacological properties. Verbascoside, the most abundant compound in this plant, has protective effects associated mostly with its strong antioxidant activity. The purpose of this study was to test the effect of L. citriodora extract intake on the antioxidant response of blood cells and to correlate this response with the phenolic metabolites found in plasma. For this purpose, firstly the L. citriodora extract was characterized and its radical scavenging activity was measured by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Then, catalase (CAT), glutathione peroxidase (GPx), and glutathione reductase (GRed) activities were determined in lymphocytes, erythrocytes, and neutrophils isolated from rats after acute intake of L. citriodora. Phenolic metabolites were analyzed in the same plasma samples by HPLC-ESI-TOF-MS. Myeloperoxidase (MPO) activity in neutrophils, which has been proposed as a marker for inflammatory vascular damage, was also determined. After L. citriodora administration, the antioxidant enzymes activities significantly accelerated (p<0.05) while MPO activity subsided, indicating that the extract protects blood cells against oxidative damage and shows potential anti-inflammatory and antiatherogenic activities. The main compounds found in plasma were Verbascoside and isoVerbascoside at a concentration of 80±10 and 57±4 ng/ml, respectively. Five other metabolites derived from Verbascoside and isoVerbascoside were also found in plasma, namely hydroxytyrosol, caffeic acid, ferulic acid, ferulic acid glucuronide, and homoprotocatechuic acid, together with another eight phenolic compounds. Therefore, the phenylpropanoids Verbascoside and isoVerbascoside, as well as their metabolites, seem to be the responsible for the above-mentioned effects, although the post-transcriptional activation mechanism of blood-cell antioxidant enzymes by these compounds needs further investigation.

  • high performance liquid chromatography with diode array detection coupled to electrospray time of flight and ion trap tandem mass spectrometry to identify phenolic compounds from a lemon verbena extract
    Journal of Chromatography A, 2009
    Co-Authors: Rosa Quirantespine, Lorena Funes, Vicente Micol, Antonio Seguracarretero, Alberto Fernandezgutierrez
    Abstract:

    Abstract High-performance liquid chromatography with diode array and electrospray ionization mass spectrometric detection was used to carry out the comprehensive characterization of a lemon verbena extract with demonstrated antioxidant and antiinflammatory activity. Two different MS techniques have been coupled to HPLC: on one hand, time-of-flight mass spectrometry, and on the other hand, tandem mass spectrometry on an ion-trap. The use of a small particle size C18 column (1.8 μm) provided a great resolution and made possible the separation of several isomers. The UV–visible spectrophotometry was used to delimit the class of phenolic compound and the accurate mass measurements on time-of-flight spectrometer enabled to identify the compounds present in the extract. Finally, the fragmentation pattern obtained in MS–MS experiments confirmed the proposed structures. This procedure was able to determine many well-known phenolic compounds present in lemon verbena such as Verbascoside and its derivatives, diglucuronide derivatives of apigenin and luteolin, and eukovoside. Also gardoside, verbasoside, cistanoside F, theveside, campneoside I, chrysoeriol-7-diglucuronide, forsythoside A and acacetin-7-diglucuronide were found for the first time in lemon verbena.