Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids
Mycolic acids, the hallmark of mycobacteria and related bacteria, are major and specific components of their cell envelope and essential for the mycobacterial survival. Mycobacteria contain structurally related long-chain lipids, but the metabolic relationships between these various classes of compo...
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Format: | Article |
Language: | English |
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Elsevier
2009-03-01
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Series: | Journal of Lipid Research |
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Online Access: | http://www.sciencedirect.com/science/article/pii/S0022227520308919 |
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doaj-46a58bb995db47068f7ea1d93c373058 |
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record_format |
Article |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Elie Rafidinarivo Marie-Antoinette Lanéelle Henri Montrozier Pedro Valero-Guillén José Astola Marina Luquin Jean-Claude Promé Mamadou Daffé |
spellingShingle |
Elie Rafidinarivo Marie-Antoinette Lanéelle Henri Montrozier Pedro Valero-Guillén José Astola Marina Luquin Jean-Claude Promé Mamadou Daffé Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids Journal of Lipid Research mycobacteria biosynthesis catabolism Baeyer-Villiger reaction oxidation |
author_facet |
Elie Rafidinarivo Marie-Antoinette Lanéelle Henri Montrozier Pedro Valero-Guillén José Astola Marina Luquin Jean-Claude Promé Mamadou Daffé |
author_sort |
Elie Rafidinarivo |
title |
Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
title_short |
Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
title_full |
Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
title_fullStr |
Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
title_full_unstemmed |
Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
title_sort |
trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acids |
publisher |
Elsevier |
series |
Journal of Lipid Research |
issn |
0022-2275 |
publishDate |
2009-03-01 |
description |
Mycolic acids, the hallmark of mycobacteria and related bacteria, are major and specific components of their cell envelope and essential for the mycobacterial survival. Mycobacteria contain structurally related long-chain lipids, but the metabolic relationships between these various classes of compounds remain obscure. To address this question a series of C35 to C54 nonhydroxylated fatty acids (mycobacteric acids), ketones, and alcohols structurally related to the C70–80 dicyclopropanated or diethylenic mycolic acids were characterized in three mycobacterial strains and their structures compared. The relationships between these long-chain acids and mycolic acids were established by following the in vivo traffic of 14C labeled α-mycolic acids purified from the same mycobacterial species. The labeling was exclusively found in mycobacteric acids. The mechanism of this degradation was established by incorporation of 18O2 into long-chain lipids and shown to consist in the rupture of mycolic acids between carbon 3 and 4 by a Baeyer-Villiger-like reaction. We also demonstrated that mycobacteric acids occur exclusively in the triacylglycerol (TAG) fraction where one molecule of these acids esterifies one of the three hydroxyl groups of glycerol. Altogether, these data suggest that these compounds represent a pathway of metabolic energy that would be used by mycobacteria in particular circumstances. |
topic |
mycobacteria biosynthesis catabolism Baeyer-Villiger reaction oxidation |
url |
http://www.sciencedirect.com/science/article/pii/S0022227520308919 |
work_keys_str_mv |
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1721504826503725056 |
spelling |
doaj-46a58bb995db47068f7ea1d93c3730582021-04-28T05:57:13ZengElsevierJournal of Lipid Research0022-22752009-03-01503477490Trafficking pathways of mycolic acids: structures, origin, mechanism of formation, and storage form of mycobacteric acidsElie Rafidinarivo0Marie-Antoinette Lanéelle1Henri Montrozier2Pedro Valero-Guillén3José Astola4Marina Luquin5Jean-Claude Promé6Mamadou Daffé7Université Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarUniversité Paul Sabatier (Toulouse III), Institut de Pharmacologie et Biologie Structurale (IPBS), 205 route de Narbonne, 31077 Toulouse Cedex, France; Centre National de la Recherche Scientifique (Unité Mixte de Recherche 5089), IPBS, Department ‘Mécanismes Moléculaires des Infections Mycobactériennes,’ 205 route de Narbonne, 31077 Toulouse Cedex, France; Departamento de Genética y Microbiologia, Facultad de Medicina y Odontologia, Universidad de Murcia, 30100 Murcia, Spain; Departament de Genètica y Microbiologia, Facultat de Ciences, Universitat Autonoma de Barcelona, 08193 Bellaterra, Spain; Present address of E. Rafidinarivo: Ecole Normale Niveau III, B.P. 881, 101 Antananarivo, MadagascarMycolic acids, the hallmark of mycobacteria and related bacteria, are major and specific components of their cell envelope and essential for the mycobacterial survival. Mycobacteria contain structurally related long-chain lipids, but the metabolic relationships between these various classes of compounds remain obscure. To address this question a series of C35 to C54 nonhydroxylated fatty acids (mycobacteric acids), ketones, and alcohols structurally related to the C70–80 dicyclopropanated or diethylenic mycolic acids were characterized in three mycobacterial strains and their structures compared. The relationships between these long-chain acids and mycolic acids were established by following the in vivo traffic of 14C labeled α-mycolic acids purified from the same mycobacterial species. The labeling was exclusively found in mycobacteric acids. The mechanism of this degradation was established by incorporation of 18O2 into long-chain lipids and shown to consist in the rupture of mycolic acids between carbon 3 and 4 by a Baeyer-Villiger-like reaction. We also demonstrated that mycobacteric acids occur exclusively in the triacylglycerol (TAG) fraction where one molecule of these acids esterifies one of the three hydroxyl groups of glycerol. Altogether, these data suggest that these compounds represent a pathway of metabolic energy that would be used by mycobacteria in particular circumstances.http://www.sciencedirect.com/science/article/pii/S0022227520308919mycobacteriabiosynthesiscatabolismBaeyer-Villiger reactionoxidation |