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Andre Pichette - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and cytotoxicity of Lupane-type triterpenoid glyceryl esters
Bioorganic and Medicinal Chemistry Letters, 2012Co-Authors: M. Thibeault, C. Gauthier, J. Legault, J. Boucharb, Lionel Gagnevin, Andre PichetteAbstract:introducing a D-glycerol moiety at the C-3 and/or C-28 positions of the Lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure-activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the Lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
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Synthesis and cytotoxicity of Lupane-type triterpenoid glyceryl esters.
Bioorganic & medicinal chemistry letters, 2012Co-Authors: Dominic Thibeault, Charles Gauthier, Jean Legault, Jimmy Bouchard, Louis Gagné, Andre PichetteAbstract:A new series of betulinic acid and betulin derivatives were synthesized by introducing a D-glycerol moiety at the C-3 and/or C-28 positions of the Lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure-activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the Lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
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Advances in the synthesis and pharmacological activity of Lupane-type triterpenoid saponins
Phytochemistry Reviews, 2011Co-Authors: Charles Gauthier, Jean Legault, Marianne Piochon-gauthier, Andre PichetteAbstract:Lupeol, betulin and betulinic acid are members of the so-called Lupane-type triterpenoids. These natural products found worldwide in quite of lot of vegetables, fruits and plant species exhibit promising pharmacological activities including anti-inflammatory, anti-HIV and antitumor activities. Nevertheless, the poor pharmacokinetic properties of these cholesterol-like triterpenoids hampered further pharmaceutical developments. The synthesis of Lupane-type saponins, i.e., sugar-derived Lupanes, seems to be a good avenue to improve both their water solubility and pharmacological activity. The aims of this review are twofold: first, to describe the biological activity of naturally occurring Lupane-type saponins, and second, report the different methodologies employed for the elaboration of glycosidic linkages at the C-3 and/or C-28 positions on the Lupane core. The synthesis of both natural and unnatural Lupane-type saponins is discussed with an emphasis on molecules exhibiting relevant biological activities.
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haemolytic activity cytotoxicity and membrane cell permeabilization of semi synthetic and natural Lupane and oleanane type saponins
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Karl Girardlalancette, Vakhtang Mshvildadze, Andre PichetteAbstract:Abstract The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure–activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 μM) independently of the nature of the sugar moieties. While oleanane-type saponins such as β-hederin ( 25 ) and hederacolchiside A 1 ( 27 ) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an α- l -rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
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Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural Lupane- and oleanane-type saponins.
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Vakhtang Mshvildadze, Karl Girard-lalancette, Andre PichetteAbstract:The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure-activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 microM) independently of the nature of the sugar moieties. While oleanane-type saponins such as beta-hederin (25) and hederacolchiside A(1) (27) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an alpha-l-rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
Charles Gauthier - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and cytotoxicity of Lupane-type triterpenoid glyceryl esters.
Bioorganic & medicinal chemistry letters, 2012Co-Authors: Dominic Thibeault, Charles Gauthier, Jean Legault, Jimmy Bouchard, Louis Gagné, Andre PichetteAbstract:A new series of betulinic acid and betulin derivatives were synthesized by introducing a D-glycerol moiety at the C-3 and/or C-28 positions of the Lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure-activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the Lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
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Advances in the synthesis and pharmacological activity of Lupane-type triterpenoid saponins
Phytochemistry Reviews, 2011Co-Authors: Charles Gauthier, Jean Legault, Marianne Piochon-gauthier, Andre PichetteAbstract:Lupeol, betulin and betulinic acid are members of the so-called Lupane-type triterpenoids. These natural products found worldwide in quite of lot of vegetables, fruits and plant species exhibit promising pharmacological activities including anti-inflammatory, anti-HIV and antitumor activities. Nevertheless, the poor pharmacokinetic properties of these cholesterol-like triterpenoids hampered further pharmaceutical developments. The synthesis of Lupane-type saponins, i.e., sugar-derived Lupanes, seems to be a good avenue to improve both their water solubility and pharmacological activity. The aims of this review are twofold: first, to describe the biological activity of naturally occurring Lupane-type saponins, and second, report the different methodologies employed for the elaboration of glycosidic linkages at the C-3 and/or C-28 positions on the Lupane core. The synthesis of both natural and unnatural Lupane-type saponins is discussed with an emphasis on molecules exhibiting relevant biological activities.
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haemolytic activity cytotoxicity and membrane cell permeabilization of semi synthetic and natural Lupane and oleanane type saponins
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Karl Girardlalancette, Vakhtang Mshvildadze, Andre PichetteAbstract:Abstract The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure–activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 μM) independently of the nature of the sugar moieties. While oleanane-type saponins such as β-hederin ( 25 ) and hederacolchiside A 1 ( 27 ) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an α- l -rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
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Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural Lupane- and oleanane-type saponins.
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Vakhtang Mshvildadze, Karl Girard-lalancette, Andre PichetteAbstract:The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure-activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 microM) independently of the nature of the sugar moieties. While oleanane-type saponins such as beta-hederin (25) and hederacolchiside A(1) (27) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an alpha-l-rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
Jean Legault - One of the best experts on this subject based on the ideXlab platform.
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Synthesis and cytotoxicity of Lupane-type triterpenoid glyceryl esters.
Bioorganic & medicinal chemistry letters, 2012Co-Authors: Dominic Thibeault, Charles Gauthier, Jean Legault, Jimmy Bouchard, Louis Gagné, Andre PichetteAbstract:A new series of betulinic acid and betulin derivatives were synthesized by introducing a D-glycerol moiety at the C-3 and/or C-28 positions of the Lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure-activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the Lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
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Advances in the synthesis and pharmacological activity of Lupane-type triterpenoid saponins
Phytochemistry Reviews, 2011Co-Authors: Charles Gauthier, Jean Legault, Marianne Piochon-gauthier, Andre PichetteAbstract:Lupeol, betulin and betulinic acid are members of the so-called Lupane-type triterpenoids. These natural products found worldwide in quite of lot of vegetables, fruits and plant species exhibit promising pharmacological activities including anti-inflammatory, anti-HIV and antitumor activities. Nevertheless, the poor pharmacokinetic properties of these cholesterol-like triterpenoids hampered further pharmaceutical developments. The synthesis of Lupane-type saponins, i.e., sugar-derived Lupanes, seems to be a good avenue to improve both their water solubility and pharmacological activity. The aims of this review are twofold: first, to describe the biological activity of naturally occurring Lupane-type saponins, and second, report the different methodologies employed for the elaboration of glycosidic linkages at the C-3 and/or C-28 positions on the Lupane core. The synthesis of both natural and unnatural Lupane-type saponins is discussed with an emphasis on molecules exhibiting relevant biological activities.
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haemolytic activity cytotoxicity and membrane cell permeabilization of semi synthetic and natural Lupane and oleanane type saponins
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Karl Girardlalancette, Vakhtang Mshvildadze, Andre PichetteAbstract:Abstract The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure–activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 μM) independently of the nature of the sugar moieties. While oleanane-type saponins such as β-hederin ( 25 ) and hederacolchiside A 1 ( 27 ) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an α- l -rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
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Haemolytic activity, cytotoxicity and membrane cell permeabilization of semi-synthetic and natural Lupane- and oleanane-type saponins.
Bioorganic & Medicinal Chemistry, 2009Co-Authors: Charles Gauthier, Jean Legault, Vakhtang Mshvildadze, Karl Girard-lalancette, Andre PichetteAbstract:The haemolysis of red blood cells inducing toxicity in most animals including humans is a major drawback for the clinical development of saponins as antitumour agents. In this study, the haemolytic and cytotoxic activities as well as the membrane cell permeabilization property of a library of 31 semi-synthetic and natural Lupane- and oleanane-type saponins were evaluated and the structure-activity relationships were established. It was shown that Lupane-type saponins do not exhibit any haemolytic activity and membrane cell permeabilization property at the maximum concentration tested (100 microM) independently of the nature of the sugar moieties. While oleanane-type saponins such as beta-hederin (25) and hederacolchiside A(1) (27) cause the death of cancer cell lines by permeabilizing the cellular membranes, Lupane-type saponins seem to proceed via another mechanism, which could be related to the induction of apoptosis. Altogether, the results indicate that the cytotoxic Lupane-type glycosides 10 and 22 bearing an alpha-l-rhamnopyranose moiety at the C-3 position represent promising antitumour agents for further studies on tumour-bearing mice since they are devoid of toxicity associated with the haemolysis of red blood cells.
Ji Young Ahn - One of the best experts on this subject based on the ideXlab platform.
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structure activity relationship of Lupane triterpene glycosides from acanthopanax koreanum on spleen lymphocyte il 2 and ifn γ
Bioorganic & Medicinal Chemistry Letters, 2010Co-Authors: Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Bui Huu Tai, Nguyen Huu Tung, Kwang Su Soung, Jun Ho Kim, Ji Young AhnAbstract:Abstract Phytochemical investigation resulted in the isolation of three new Lupane-triterpene glycosides acankoreosides M–O (1, 2 and 8) together with eight known Lupane-triterpene glycosides (3–7, 9–11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven Lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.
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Structure–activity relationship of Lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ
Bioorganic & medicinal chemistry letters, 2010Co-Authors: Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Bui Huu Tai, Nguyen Huu Tung, Kwang Su Soung, Jun Ho Kim, Ji Young Ahn, Young-mi LeeAbstract:Abstract Phytochemical investigation resulted in the isolation of three new Lupane-triterpene glycosides acankoreosides M–O (1, 2 and 8) together with eight known Lupane-triterpene glycosides (3–7, 9–11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven Lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.
Bui Huu Tai - One of the best experts on this subject based on the ideXlab platform.
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structure activity relationship of Lupane triterpene glycosides from acanthopanax koreanum on spleen lymphocyte il 2 and ifn γ
Bioorganic & Medicinal Chemistry Letters, 2010Co-Authors: Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Bui Huu Tai, Nguyen Huu Tung, Kwang Su Soung, Jun Ho Kim, Ji Young AhnAbstract:Abstract Phytochemical investigation resulted in the isolation of three new Lupane-triterpene glycosides acankoreosides M–O (1, 2 and 8) together with eight known Lupane-triterpene glycosides (3–7, 9–11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven Lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.
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Structure–activity relationship of Lupane-triterpene glycosides from Acanthopanax koreanum on spleen lymphocyte IL-2 and IFN-γ
Bioorganic & medicinal chemistry letters, 2010Co-Authors: Nguyen Xuan Nhiem, Phan Van Kiem, Chau Van Minh, Bui Huu Tai, Nguyen Huu Tung, Kwang Su Soung, Jun Ho Kim, Ji Young Ahn, Young-mi LeeAbstract:Abstract Phytochemical investigation resulted in the isolation of three new Lupane-triterpene glycosides acankoreosides M–O (1, 2 and 8) together with eight known Lupane-triterpene glycosides (3–7, 9–11) from the leaves of Acanthopanax koreanum (Araliaceae). Their chemical structures were elucidated by mass, 1D and 2D NMR spectroscopy. The effect of eleven Lupane-triterpene glycosides on Con A-induced splenolytic production of IL-2 and IFN-γ were measured as markers of acquired immune responses. Compounds 4, 5, 7, and 11 (5, 25, and 100 μM) significantly increased IFN-γ and IL-2 release in spleen cells.