Chemical Synthesis and Isolation of trans‐Palmitoleic Acid (trans ‐C16:1 n‐7) Suitable for Nutritional Studies

Autor: Clément Orione, Gaëtan Drouin, Etienne Guillocheau, Vincent Rioux, Philippe Legrand, Daniel Catheline
Přispěvatelé: Laboratoire de Biochimie et Nutrition Humaine, AGROCAMPUS OUEST, Centre Régional de Mesures Physiques de l'Ouest (CRMPO), Université de Rennes (UR), Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)
Jazyk: angličtina
Rok vydání: 2020
Předmět:
Nutritional studies
[SDV.IDA.CA]Life Sciences [q-bio]/Food engineering/domain_sdv.ida.ca
030309 nutrition & dietetics
Type 2 diabetes
Trans-palmitoleic acid
Chemical synthesis
Industrial and Manufacturing Engineering
03 medical and health sciences
chemistry.chemical_compound
0404 agricultural biotechnology
medicine
Palmitoleic acid
Food science
[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry
Molecular Biology/Biochemistry [q-bio.BM]
Purification
2. Zero hunger
Current time
0303 health sciences
Chemistry
04 agricultural and veterinary sciences
General Chemistry
Ethyl ester
Nuclear magnetic resonance spectrometry
medicine.disease
040401 food science
[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry
Molecular Biology/Biomolecules [q-bio.BM]
3. Good health
Methanol
Metabolic syndrome
Food Science
Biotechnology
Zdroj: European Journal of Lipid Science and Technology
European Journal of Lipid Science and Technology, In press, ⟨10.1002/ejlt.201900409⟩
European Journal of Lipid Science and Technology, Wiley-VCH Verlag, In press, ⟨10.1002/ejlt.201900409⟩
ISSN: 1438-7697
1438-9312
DOI: 10.1002/ejlt.201900409⟩
Popis: International audience; Trans‐palmitoleic acid (trans‐9 C16:1, or trans‐C16:1 n‐7, TPA) is typically found in ruminant‐derived foods (milk and meat). Of note, previous epidemiological studies associated high levels of circulating TPA with a lower risk of type 2 diabetes and metabolic syndrome in humans. At the current time, TPA intakes in humans are ensured by ruminant‐derived foods. However, due to the very low commercial availability of TPA, there are no supplementation studies carried out so far. Therefore, the ability for dietary TPA to prevent type 2 diabetes and metabolic syndrome has never been experimentally assessed. Here, we report a method (among others) to get dozens of grams of pure TPA as ethyl ester, to perform dedicated supplementation studies. For that purpose, we started from food sources containing high amounts of cis‐palmitoleic acid (cis‐9 C16:1, or cis‐C16:1 n‐7, CPA), dealing with fatty acids ethyl esters all along with the experiment. CPA was purified with flash LC, then submitted to a cis/trans isomerization step. Finally, TPA was separated from CPA by low‐temperature crystallization in methanol. The final product was fully characterized by 1H and 13C nuclear magnetic resonance spectrometry. We were able to produce approx. 70 g of 85%‐purity TPA suitable for nutritional studies.
Databáze: OpenAIRE
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