Fluorimetric analysis of lipase hydrolysis of intermediate- and long-chain glycerides

Tsuzuki, Wakako; Ue, Akemi; Nagao, Akihiko; Akasaka, Kazuaki

doi:10.1039/b110038f

Cited by 12 publications

(7 citation statements)

References 20 publications

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“…Despite the diverse studies that have reported the controversial about digestion, absorption, and transport of ω‐3 concentrates under different forms, the study of the lipid content and composition of the MP formed during luminal metabolism of these lipids is scarce. Several studies have been carried out regarding composition of the whole digestion medium by in vitro assays 3, 7–9 but most of them did not deal with the potentially absorbable fraction, which might be the hydrolysis products included in the MP.…”

Section: Introductionmentioning

confidence: 99%

Intestinal digestion of fish oils and ω‐3 concentrates under in vitro conditions

Martín

Nieto

Señoráns

et al. 2010

Euro J Lipid Sci & Tech

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A comparative study of the in vitro bioaccesibility of v-3-oils (salmon oil, SO; tuna oil, TO; enriched-v-3 oil as triacylglycerols (TAGs), v-3-TAG; and enriched-v-3 oil as ethyl esters (EEs), v-3-EE) was performed after treatment with pancreatin (pancreatic lipase as major lipolytic enzyme) at pH 7.5. Aliquots were taken at different times of digestion for analyzing the evolution of lipid products. The micellar phase (MP) formed at 120 min of digestion was isolated, its total lipid content was extracted and its composition in lipid products was analyzed. The rate of hydrolysis of v-3-TAG concentrates was continuous throughout the time of reaction (51% hydrolysis of TAGs at 120 min), whereas the digestion of SO and TO was initially faster but stopped after 10 min of reaction (35 and 38% hydrolysis of TAGs at 120 min of SO and TO, respectively). A poor hydrolysis of EEs took place for the v-3-EE oil (around 7% hydrolysis of EEs at 120 min). The MP of v-3-TAG oil, SO, and TO mainly consisted of free fatty acids (FFAs) and MAGs. The MP from digested v-3-EE oil consisted of FFAs and undigested EEs. Therefore, the highest degree of hydrolysis and inclusion of lipid products in the micellar structure was found for the v-3-TAG oil, but compared to fish oils long times of digestion were required. This experience also shows for the first time the MP composition from v-3-concentrates in the form of EEs.Practical applications: Commercial v-3 sources can be found as purified fish oil or concentrates in the form of TAGs, FFAs, and EEs. Despite differences exist regarding their intestinal metabolism, there is lack of information about the specific composition in lipolytic products of the absorbable fraction (MP) from v-3-TAG or v-3-EE concentrates. This comparative study showed that (i) the in vitro bioaccesibility of v-3-polyunsaturated fatty acid (PUFA) seems to be better as v-3-TAG concentrates than purified fish oils, but after long times of digestion; and (ii) the in vitro hydrolysis of v-3-PUFA as EEs seems to be poor, at least after the activity of the major lipolytic enzyme of pancreatin, namely pancreatic lipase. Furthermore, the inclusion of EEs within micellar structures seems to be limited. These results contribute to the knowledge of the intestinal lipolysis of v-3 sources by showing the composition of the MP on lipid products for the first time.

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Section: Introductionmentioning

confidence: 99%

Intestinal digestion of fish oils and ω‐3 concentrates under in vitro conditions

Martín

Nieto

Señoráns

et al. 2010

Euro J Lipid Sci & Tech

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“…A series of N-(tert-butoxycarbonyl)-neurotransmitter amino acids 1 (glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid) were reacted with 9-bromomethylacridine 2 25 to afford the corresponding heterocyclic ester derivatives 3, via a potassium fluoride coupling in N,Ndimethylformamide, at room temperature (Scheme 1 and Table 1). 27 The acridin-9-yl methylene group will be designated in this report by a three-letter code (Acm) for simplicity of naming the various fluorescent derivatives, as indicated in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…Chloroform ( In view of the current use of 9-bromomethylacridine as HPLC derivatizing agent for fluorescent labelling of carboxylic acids, 25,26 the present work represents a novel application, indicative of its versatility and as a result this azaheterocycle can be regarded as an addition to the collection of photolabile protecting groups for the carboxylic acid function.…”

Section: Additionally To Monitoring the Photolysis Process By Hplc/uvmentioning

confidence: 99%

“…20,21 Over the time, these compounds have found application as derivatizing agents, being recently reported, for example, as fluorescent chemosensors for metal ions. [22][23][24][25][26] The photocontrolled release in time and space for the study of the kinetics of bioactive molecules is an established technique for the study of fast biological processes involving neurotransmitters, such as amino acids, nucleotides and physiological amines. As a result, there is a strong interest in the search for more efficient photolabile protecting groups with ability to cleave under irradiation at higher wavelengths, in order to minimise cellular damage.…”

Section: Introductionmentioning

confidence: 99%

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Acridinyl methyl esters as photoactive precursors in the release of neurotransmitteramino acids

Piloto

Hungerford

Costa

et al. 2013

Photochem Photobiol Sci

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An investigation of the use of an azaheterocycle, acridine, as an alternative photochemically removable protecting group for the carboxylic function of neurotransmitter amino acids was carried out. 9-Bromomethylacridine was used in the reaction with glycine, alanine, glutamic acid, β-alanine and γ-aminobutyric acid, to obtain model ester derivatives, which were irradiated at different wavelengths in a photochemical reactor. The process was followed by HPLC/UV, resulting in the release of the active molecule in short irradiation times. The results obtained using 419 nm irradiation show promise (35-98 min) for practical purposes. The compounds were further characterised via time-resolved fluorescence to elucidate their photophysical properties and determine the decay kinetics.

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“…5, compared to the normal hydrolysis process of TB. Other reasons related to the own etherified alkyl chain, the hydrophobicity of the whole molecule or the steric structure, might influence the interaction of the enzyme with alkylglycerols and explain the different course of reaction respect to TB [30,31].…”

Section: Discussionmentioning

confidence: 98%

In Vitro Intestinal Bioaccessibility of Alkylglycerols Versus Triacylglycerols as Vehicles of Butyric Acid

Martín

Morán-Valero

Señoráns

et al. 2011

Lipids

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Butyric acid has been the subject of much attention last years due to its bioactivity. However, the potential advantages of butyrate are limited by the problem to reach enough plasma concentrations; therefore, pro-drugs have been proposed as an alternative to natural butyrate. A comparative study on in vitro intestinal digestion of 2,3-dibutyroil-1-O-octadecyl glycerol (D-SCAKG) and tributyrin (TB), as potential pro-drugs of butyric acid, was performed. Aliquots were taken at different times of digestion for studying the extent and rate of hydrolysis of both substrates. The micellar phase (MP) and oily phase (OP) formed in the digestion media were separated and their composition in lipid products was analyzed. Initially, it was confirmed that the in vitro model reproduced physiological results by testing against olive oil as a standard lipid. The progress of in vitro intestinal digestion of D-SCAKG was slower than that of TB. TB hydrolyzed completely to butyric acid, whereas D-SCAKG mainly yielded 2-butyroil-1-O-octadecyl glycerol (M-SCAKG), followed by butyric acid and 1-O-octadecyl glycerol (AKG). The MP from both substrates mainly consisted of butyric acid. Minor levels of M-SCAKG and AKG were also found in the MP after hydrolysis of D-SCAKG, the M-SCAKG being mainly distributed in the OP. Therefore, D-SCAKG produced a stable form of esterified butyric acid as M-SCAKG after in vitro intestinal digestion, unlike TB. Additionally, such a product would integrate both bioactive compounds, butyric acid and alkylglycerol, within the same molecule. Free butyric acid and AKG would be also released, which are lipid products of interest as well.

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Fluorimetric analysis of lipase hydrolysis of intermediate- and long-chain glycerides

Cited by 12 publications

References 20 publications

Intestinal digestion of fish oils and ω‐3 concentrates under in vitro conditions

Intestinal digestion of fish oils and ω‐3 concentrates under in vitro conditions

Acridinyl methyl esters as photoactive precursors in the release of neurotransmitteramino acids

In Vitro Intestinal Bioaccessibility of Alkylglycerols Versus Triacylglycerols as Vehicles of Butyric Acid

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