Facile synthesis of cyclopentenone B1- and L1-type phytoprostanes
被引:18
作者:
Guy, Alexandre
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Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, FranceUniv Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
Guy, Alexandre
[1
]
Flanagan, Seamus
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Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, FranceUniv Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
Flanagan, Seamus
[1
]
Durand, Thierry
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Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, FranceUniv Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
Durand, Thierry
[1
]
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Oger, Camille
[1
]
Galano, Jean-Marie
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机构:
Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, FranceUniv Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
Galano, Jean-Marie
[1
]
机构:
[1] Univ Montpellier, Fac Pharm, Ecole Natl Super Chim Montpellier, Inst Biomol Max Mousseron,CNRS,UMR 5247, F-34093 Montpellier, France
Phytoprostanes (PhytoPs) represent non -enzymatic metabolites of alpha-linolenic acid (ALA), the essential omega-3 polyunsaturated fatty acid (PUFA) derived from plants. PhytoPs are present in the plant kingdom and represent endogenous mediators capable of protecting cells from oxidative stress damages in plants. Recently, it was found that such metabolites are present in cooking oil in high quantities, and also that B-1-PhytoPs protect immature neurons from oxidant injury and promote differentiation of oligodendrocyte progenitors through PPAR-gamma activation. We report a novel and facile synthesis of natural 2,3-substituted cyclopentenone PhytoPs, 16-B-1-PhytoP, and 9-L-1-PhytoP. Our strategy is based on reductive alkylation at the 2-position of 1,3-cyclopentanedione using a recent protocol developed by Ramachary et al. and on a cross-coupling metathesis to access conjugate dienone system. In conclusion, this strategy permitted access to B-1- and L-1-PhytoPs in a relative short sequence process, and afford the possibility to easily develop analogs of PhytoPs.
机构:
Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Barden, Anne E.
;
Croft, Kevin D.
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Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Croft, Kevin D.
;
Durand, Thierry
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h-index: 0
机构:
Univ Montpellier 2, Univ Montpellier 1, CNRS, Inst Biomol Max Mousseron,UMR 5247, F-34093 Montpellier, FranceUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Durand, Thierry
;
Guy, Alexandre
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h-index: 0
机构:
Univ Montpellier 2, Univ Montpellier 1, CNRS, Inst Biomol Max Mousseron,UMR 5247, F-34093 Montpellier, FranceUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Guy, Alexandre
;
Mueller, Martin J.
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机构:
Univ Wurzburg, Bioctr, D-97082 Wurzburg, GermanyUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Mueller, Martin J.
;
Mori, Trevor A.
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Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Collado-Gonzalez, Jacinta
;
Perez-Lopez, David
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h-index: 0
机构:
Tech Univ Madrid, Escuela Ingn Tecn Agr, Dept Producc Vegetal, Fitotecnia, Madrid 28040, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Perez-Lopez, David
;
Memmi, Houssem.
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h-index: 0
机构:
Ctr Agr El Chaparrillo, Ciudad Real, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Memmi, Houssem.
;
Carmen Gijon, M.
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h-index: 0
机构:
Ctr Agr El Chaparrillo, Ciudad Real, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Carmen Gijon, M.
;
Medina, Sonia
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机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Medina, Sonia
;
Durand, Thierry
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Durand, Thierry
;
Guy, Alexandre
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h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Guy, Alexandre
;
Galano, Jean-Marie
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h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Galano, Jean-Marie
;
Ferreres, Federico
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CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Ferreres, Federico
;
Torrecillas, Arturo
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机构:
CEBAS CSIC, Dept Irrigat, E-30100 Murcia, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Torrecillas, Arturo
;
Gil-Izquierdo, Angel
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机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
El Fangour, S
;
Guy, A
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Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Guy, A
;
Vidal, JP
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Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Vidal, JP
;
Rossi, JC
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Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Rossi, JC
;
Durand, T
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h-index: 0
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
机构:
Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Barden, Anne E.
;
Croft, Kevin D.
论文数: 0引用数: 0
h-index: 0
机构:
Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Croft, Kevin D.
;
Durand, Thierry
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier 2, Univ Montpellier 1, CNRS, Inst Biomol Max Mousseron,UMR 5247, F-34093 Montpellier, FranceUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Durand, Thierry
;
Guy, Alexandre
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h-index: 0
机构:
Univ Montpellier 2, Univ Montpellier 1, CNRS, Inst Biomol Max Mousseron,UMR 5247, F-34093 Montpellier, FranceUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Guy, Alexandre
;
Mueller, Martin J.
论文数: 0引用数: 0
h-index: 0
机构:
Univ Wurzburg, Bioctr, D-97082 Wurzburg, GermanyUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
Mueller, Martin J.
;
Mori, Trevor A.
论文数: 0引用数: 0
h-index: 0
机构:
Univ Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, AustraliaUniv Western Australia, Royal Perth Hosp, Sch Med & Pharmacol, Cardiovasc Res Ctr, Perth, WA 6001, Australia
机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Collado-Gonzalez, Jacinta
;
Perez-Lopez, David
论文数: 0引用数: 0
h-index: 0
机构:
Tech Univ Madrid, Escuela Ingn Tecn Agr, Dept Producc Vegetal, Fitotecnia, Madrid 28040, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Perez-Lopez, David
;
Memmi, Houssem.
论文数: 0引用数: 0
h-index: 0
机构:
Ctr Agr El Chaparrillo, Ciudad Real, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Memmi, Houssem.
;
Carmen Gijon, M.
论文数: 0引用数: 0
h-index: 0
机构:
Ctr Agr El Chaparrillo, Ciudad Real, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Carmen Gijon, M.
;
Medina, Sonia
论文数: 0引用数: 0
h-index: 0
机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Medina, Sonia
;
Durand, Thierry
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Durand, Thierry
;
Guy, Alexandre
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Guy, Alexandre
;
Galano, Jean-Marie
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I & II ENSCM, CNRS, UMR 5247, Fac Pharm,IBMM, Montpellier, FranceCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Galano, Jean-Marie
;
Ferreres, Federico
论文数: 0引用数: 0
h-index: 0
机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Ferreres, Federico
;
Torrecillas, Arturo
论文数: 0引用数: 0
h-index: 0
机构:
CEBAS CSIC, Dept Irrigat, E-30100 Murcia, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
Torrecillas, Arturo
;
Gil-Izquierdo, Angel
论文数: 0引用数: 0
h-index: 0
机构:
CEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, SpainCEBAS CSIC, Dept Food Sci & Technol, Res Grp Qual Safety & Bioact Plant Foods, POB 164, Murcia 30100, Spain
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
El Fangour, S
;
Guy, A
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Guy, A
;
Vidal, JP
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Vidal, JP
;
Rossi, JC
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France
Rossi, JC
;
Durand, T
论文数: 0引用数: 0
h-index: 0
机构:
Univ Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, FranceUniv Montpellier I, Fac Pharm, UMR 5074, CNRS, F-34093 Montpellier 05, France