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JP-7857350-B2 - Mixed triglycerides

JP7857350B2JP 7857350 B2JP7857350 B2JP 7857350B2JP-7857350-B2

Inventors

  • ブランチャード， カリーヌ
  • クナウド， ベルナルト
  • デスタイラッツ， フレデリック
  • フォーブス－ブロム， エリザベス
  • ウルトリング， ヘイコー
  • パティン， アマウリー

Assignees

  • ソシエテ・デ・プロデュイ・ネスレ・エス・アー

Dates

Publication Date
20260512
Application Date
20240703
Priority Date
20181218

Claims (20)

  1. The compound comprises a compound having formula (1), a compound having formula (2), a compound having formula (3), and a compound having formula (4). The compound having formula (1) constitutes at least 2% by weight of the total triglycerides in the composition, the compound having formula (2) constitutes at least 2% by weight of the total triglycerides in the composition, the compound having formula (3) constitutes at least 2% by weight of the total triglycerides in the composition, and the compound having formula (4) constitutes at least 2% by weight of the total triglycerides in the composition. The compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 50% by weight of the total triglycerides of the composition . Tributyline constitutes less than 10% by weight of the total triglycerides in the composition. A composition for use in improving or maintaining gastrointestinal health . [In the formula, n1, n2, n3, n4, n5, and n6 are independently between 4 and 10.]
  2. The composition according to claim 1, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 60% by weight of the total triglycerides of the composition.
  3. The composition according to claim 1 or 2, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 70% by weight of the total triglycerides of the composition.
  4. The composition according to any one of claims 1 to 3, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 80% by weight of the total triglycerides of the composition.
  5. The composition according to any one of claims 1 to 4, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 90% by weight of the total triglycerides of the composition.
  6. The composition according to any one of claims 1 to 5, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 95% by weight of the total triglycerides of the composition.
  7. The composition according to any one of claims 1 to 6, wherein the compound having formula (1), the compound having formula (2), the compound having formula (3), and the compound having formula (4) constitute at least 99% by weight of the total triglycerides of the composition.
  8. A composition according to any one of claims 1 to 7, comprising a compound having the following formula or a combination thereof.
  9. The composition according to claim 8, wherein the composition comprises the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8).
  10. The composition according to claim 8 or 9, wherein the compound having formula (5) constitutes at least 2% by weight of the total triglycerides of the composition, the compound having formula (6) constitutes at least 2% by weight of the total triglycerides of the composition, the compound having formula (7) constitutes at least 2% by weight of the total triglycerides of the composition, and the compound having formula (8) constitutes at least 2% by weight of the total triglycerides of the composition.
  11. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total triglycerides of the composition.
  12. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total triglycerides of the composition.
  13. The composition according to any one of claims 8 to 10, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 70% by weight of the total triglycerides of the composition.
  14. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total butyrate-containing triglycerides in the composition.
  15. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total butyrate-containing triglycerides in the composition.
  16. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 70% by weight of the total butyrate-containing triglycerides in the composition.
  17. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 80% by weight of the total butyrate-containing triglycerides in the composition.
  18. The composition according to any one of claims 8 to 13, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 90% by weight of the total butyrate-containing triglycerides in the composition.
  19. The composition according to any one of claims 8 to 18, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 50% by weight of the total octanoate-containing triglycerides in the composition.
  20. The composition according to any one of claims 8 to 18, wherein the compound having formula (5), the compound having formula (6), the compound having formula (7), and the compound having formula (8) constitute at least 60% by weight of the total octanoate-containing triglycerides in the composition.

Description

This invention relates to a dietary source of butyric acid-containing triglycerides having improved functional properties. The invention also provides butyric acid-containing triglycerides that provide a rich source of ketones. Butyric acid salts and esters are called butyrates or butanoates. Butyric acid in ester form is found in many foods, such as milk, especially from goat, sheep, cow, camel, and buffalo, as well as milk-derived products, such as butter and cheese, such as Parmesan cheese. Butyric acid is also a product of anaerobic fermentation, such as fermentation products produced by the gut microbiota. Tributyline is a triglyceride consisting of three ester functional groups, each having three butyrate moieties, and a glycerol skeleton. Under hydrolytic conditions, such as those occurring during digestion, tributyline can be a source of 3 moles of butyric acid per mole of tributyline. Numerous beneficial effects of butyrate have been well documented in mammals and livestock. At the intestinal level, butyrate functions to regulate transepithelial fluid transport, restore mucositis and oxidative conditions, strengthen the intestinal barrier function, and act on visceral sensation and intestinal motility. Butyrate has been shown to improve intestinal structure in piglets with short bowel syndrome (Bartholome et al., J of Parenter Enteral Nutr. 2004;28(4):210-222) and to reduce the proliferation of colon cancer cells in human cell lines (Lupton, J Nutr., 2004;134(2):479-482). The role of dietary fiber in colon cancer may be due to the production of volatile fatty acids such as butyric acid from fermentable fiber (Lupton, J Nutr., 2004;134(2):479-482). Short-chain fatty acids, including but not limited to acetic acid, propionic acid, and butyric acid, are produced by colon bacteria that feed on or ferment non-digestible fiber and/or prebiotics. Butyric acid also benefits colon cells by increasing energy production. Butyrates have also been shown to reduce the incidence of diarrhea (Berni Canani et al., Gastroenterol., 2004;127(2):630-634), improve inflammatory bowel disease (Scarpellini et al., Dig Liver Dis., 2007;1(1):19-22), and improve small intestine health (Kotunia et al., J Physiol Pharmacol. 1994;55(2):59-68). Butyrates are also known to stimulate the massive production of ketones upon ingestion (Saint-Pierre et al., 2016;32 Journal of Functional Foods 32:170-175). Ketones are an alternative energy source (other than carbohydrates, proteins, and fats) that can effectively reach peripheral organs such as the brain. Ketones can directly produce acetyl-CoA in mitochondria to support ATP production and can be used in place of glucose in nerve tissue (Tetrick et al., 2010, Comparative Medicine 60:486-490). Ketones may also exhibit protective effects against free radical damage to neurons (Vanltallie TB et al, 2003, Ketones: metabolism’s ugly duckling. Nutr. Rev. 61:327-41). Several studies have suggested that ketone administration after ischemic injury may reduce the impact of ischemic injury on the brain. In fact, ketone supplementation is considered a potential treatment for traumatic brain injury (White and Venkatesh, 2011, Critical Care 15:219). Furthermore, several studies suggest that neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease may benefit from ketone administration. For example, Reger et al. (2004, Neurobiol Aging. 25:311-4.14) found that elevated serum ketone levels improved cognitive scores in Alzheimer's patients. Butyric acid and triptyline are both generally considered safe (GRAS) food additives (21 CFR 582.60 and 21 CFR 184.1903, respectively) and are natural components of many dairy products. However, butyric acid has negative sensory qualities, including vomit-like, fecal-like, and cheese-like odor characteristics. Triptyline also has negative sensory qualities, particularly a high degree of bitterness. These unpleasant taste and odor characteristics can make oral administration of compositions containing these compounds particularly difficult, especially in child populations. Medium-chain triglycerides (MCTs) and medium-chain fatty acids (MCFAs) are also sources of ketones. Octanoic acid (C8) is the most efficient MCFA for producing blood ketones in humans (Vanderberghe et al.; 2017 Curr. Dev. Nutr. 1(4)). However, high doses (more than 10g) are associated with undesirable gastrointestinal intolerances such as diarrhea and stomach cramps, limiting the amount that can be taken at one time, and consequently limiting the amount of blood ketones produced. Providing a source of food-grade butyrate with improved sensory properties compared to available products would be beneficial. [Summary of the Invention] The present invention provides a compound that is a source of butyrate, having improved sensory properties and showing promise in enhancing ketone production after oral or enteral administration in humans and other mammals. In particular, the present i