Digestion and Absorption of Lipids

Mead, James F.; Alfin-Slater, Roslyn B.; Howton, David R.; Popják, G.

doi:10.1007/978-1-4613-2107-1_12

Cited by 8 publications

(3 citation statements)

References 69 publications

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“…The fatty acids located in the sn-2 positions in the dietary fat are thus conserved during absorption (24). Long-chain fatty acids are activated to their CoA derivatives through the action of fatty acyl-CoA ligase in the endoplasmic reticulum and resynthesized to triacylglycerols together with monoacylglycerol by acyltransferase, whereas medium-chain fatty acids are predominantly transported through the portal vein, since the ligase has low activity toward medium-chain fatty acids (25). The fatty acyl synthetase responsible for triacylglycerol reesterification is most effective with fatty acids of 14 or more carbons (5).…”

Section: Discussionmentioning

confidence: 99%

Effects of different medium‐chain fatty acids on intestinal absorption of structured triacylglycerols

Høy

2000

Lipids

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To study the effect of the chain length of medium-chain fatty acids on the intestinal absorption of long-chain fatty acids, we examined the lymphatic transport of fat following administration of five purified structured triacylglycerols (STAG) containing different medium-chain fatty acids in the sn-1,3 positions and long-chain fatty acids in the sn-2 position in a rat model. Significant amounts of medium-chain fatty acids were found in lymph samples after intragastric administration of 1,3-dioctanoyl-2-linoleyl-sn-glycerol (8:0/18:2/8:0), 1,3-didecanoyl-2-linoleyl-sn-glycerol, and 1,3-didodecanoyl-2-linoleyl-sn-glycerol. The accumulated lymphatic transport of medium-chain fatty acids increased with increasing carbon chain length. The recoveries of caprylic acid (8:0), capric acid (10:0), and lauric acid (12:0) were 7.3 +/- 0.9, 26.3 +/- 2.4, and 81.7 +/- 6.9%, respectively. No significant differences were observed for the maximal intestinal absorption of linoleic acid (18:2n-6) when the chain length of medium-chain fatty acids at the primary positions was varied, and the absorption of 18:2 and oleic acid (18:1) from 8:0/18:2/8:0 and 1,3-dioctanoyl-2-oleyl-sn-glycerol was similar. We conclude that the chain length of the medium-chain fatty acids in the primary positions of STAG does not affect the maximal intestinal absorption of long-chain fatty acids in the sn-2 position in the applied rat model, whereas the distribution of fatty acids between the lymphatics and the portal vein reflects the chain length of the fatty acids.

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Section: Discussionmentioning

confidence: 99%

Effects of different medium‐chain fatty acids on intestinal absorption of structured triacylglycerols

Høy

2000

Lipids

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“…Whereas the alkyl esters are mainly hydrolysed by estearases, the triacylglycerols are hydrolysed by lipases, specific esterases, which are present in the skin in lower amounts than the other less specific esterases. The hydrolytic action of these enzymes shows a preferential activity towards fatty acids at C‐1 and C‐3 of triacylglycerols [3–14]. This fact can contribute to enhance the retention time of the triacylglycerols, where the sunscreen is on C‐2 position, therefore prolonging its protective action ‘ in vivo ’.…”

Section: Discussionmentioning

confidence: 99%

“…Triacylglycerols are hydrolysed by lipases, specific esterases, which are present in the skin in lower amounts than the other less specific esterases [2], showing a preferential activity towards fatty acids at C‐1 and C‐3 of triacylglycerols [3]. Diacylglycerols (subproducts of hydrolysis reactions) present in the stratum corneum can contribute to accelerate pigmentation [4].…”

Section: Introductionmentioning

confidence: 99%

Glyceridic esters of p‐methoxycinnamic acid. A new sunscreen of the cinnamate class

Freitas

Gonçalves

Santos

et al. 2001

Intern J of Cosmetic Sci

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The aim of this work was to investigate whether a 1,3-diacylglycerol moiety can act as enhancer of the photoprotecting action of a new sunscreen of the cinnamate class, owing to its affinity with skin constituents and lower susceptibility to hydrolysis at C-2. The sun protection factors (SPF) for 1,2,3-propanetriol 1,3-dipalmitate-2-p-methoxycinnamate and 1,2,3-propanetriol 1,3-dioctanoate-2-p-methoxy-cinnamate (2.0, 4.5 and 7.5%) were determined. The sunscreen preparations presented SPF values between 4.7 and 16. The results show that although glyceridic esters present higher lipophilicity and are more stable towards enzymatic hydrolysis in vitro, the synthesized triacylglycerols and the standard sunscreen 2-ethylhexyl p-methoxycinnamoyl (EHPM) showed equivalent SPF values for both methods.

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Synthesis and in Vitro Degradation of Testosterone‐Lipid Conjugates

Scriba

1995

Archiv der Pharmazie

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Testosterone-lipid conjugates were obtained by covalent binding of the drug to 1,3-dipalmitoylglycerol via succinic acid to 4-(1,3-dipalmitoyl-2-glyceryl)butyric acid and to 3-palmitoyloxy-2-palmitoyloxmethylpropionic acid. In contrast to the corresponding bis-deacyl derivatives, the lipids were not significantly hydrolyzed in aqueous buffers and in plasma. Incubation with pancreatic lipase yielded primarily the bis-deacyl compounds, which are comparable to monoglycerides, and subsequently slowly liberated testosterone. It is concluded that the lipid conjugates are substrates for pancreatic lipase. However, the drug was released very slowly due to steric hindrance.

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Digestion and Absorption of Lipids

Cited by 8 publications

References 69 publications

Effects of different medium‐chain fatty acids on intestinal absorption of structured triacylglycerols

Effects of different medium‐chain fatty acids on intestinal absorption of structured triacylglycerols

Glyceridic esters of p‐methoxycinnamic acid. A new sunscreen of the cinnamate class

Synthesis and in Vitro Degradation of Testosterone‐Lipid Conjugates

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