Metabolism of 14C-labelled sucrose esters of stearic acid in rats

Noker, Patricia E.; Lin, Ted; Hill, Donald L.; Shigeoka, Tadayoshi

doi:10.1016/s0278-6915(97)00012-4

Cited by 12 publications

(11 citation statements)

References 9 publications

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“…The degree of esterification and the type of fatty acid used determine their surfactant properties. It has also been demonstrated that sucrose esters (mono-, di-, or tri-esters) are hydrolysed to sucrose and fatty acids prior to intestinal absorption [11,12], giving them a GRAS (Generally Recognized As Safe) status [13]. Although different sugars and acyl donors have been widely studied [1,6,[14][15][16][17], the use of a single sugar with prebiotic properties, such as properties, such as lactulose, has been less studied [18,19] and might open significant applications the food and pharmaceutical fields.…”

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

et al. 2017

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Abstract:The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces "monoester fraction 1", while Thermomyces lanuginosus lipase (Lipozyme ® TL IM) and Mucor miehei lipase (Lipozyme ® ) seem to produce the same "monoester fraction 2". These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme ® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6 -O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics.

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Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

et al. 2017

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“…Such a broad HLB range is obtained by: (i) the sucrose head group which can be esterified at up to eight sites and (ii) the variability in the length of the fatty acid chain (Husband, Sarney, Barnard, & Wilde, 1998). SuEs are non-toxic and biodegradable because they are enzymatically hydrolyzed to sucrose and fatty acids prior to intestinal absorption or excreted in feces (Noker, Lin, Hill, & Shigeoka, 1997;Shigeoka, Izawa, Kitazawa, & Yamauchi, 1984). In 2004 the European Food Safety Authority (EFSA) established an acceptable daily intake of 40 mg/kg bw/day for SuE.…”

Section: Introductionmentioning

confidence: 99%

“…In 2004 the European Food Safety Authority (EFSA) established an acceptable daily intake of 40 mg/kg bw/day for SuE. This is however not the case for higher esters (hexa-to octaesters) which are not hydrolyzed in the gut (Noker et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

Development of a quantitative GC-FID method for the determination of sucrose mono- and diesters in foods

Cucu

Meulenaer

2015

Food Additives & Contaminants: Part A

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Sucrose esters (E 473) are emulsifiers used in foods to improve different technological properties. They should conform to the specifications laid down in Commission Regulation No. 231/2012 and be used at amounts not exceeding the maximal ones set by Commission Regulation No. 1129/2011. In order to be able to characterise commercial sucrose ester formulations and to evaluate whether they are used correctly by the food industry, a quantitative GC-FID method was developed. Standards of monoesters and diesters were isolated from commercial additive preparations because no commercial ones were available. Commercial sucrose monolaureate and in-house-synthesised sucrose diarachidonate were used as internal standards. The method showed limits of detection and quantification of 2.9 and 5.7 µg ml(-1) respectively for the monoesters and 42.8 and 129.7 µg ml(-1) respectively for the diesters. The analysed commercial additive formulations contained mainly mono- and diesters of palmitic and stearic acid with low amounts of free fatty acid and sucrose. Different food matrices were incurred with commercial sucrose esters formulations and recoveries ranged between 92% and 118% for the monoesters and between 77% and 120% for the diesters. Recovery of sucrose monoesters in cake was around 34% when no enzymatic treatment was applied, and about 64% when enzymatic treatment with Clara-Diastase was applied. This indicated that sucrose esters can interact strongly with the matrix during food production and that treatment with enzymes is essential to determine the esters' content accurately in some classes of food products.

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“…However, this difference significantly decreased when cells were examined with real-time monitoring for 24 h. In oral preparations the cellular toxicity of excipients can be diminished by dilution in the gastrointestinal fluids, in addition sucrose esters are hydrolysed and absorbed as sucrose and individual fatty acids in the gastrointestinal tract (Noker et al, 1997). In the nasal mucous membrane, considerable dilution cannot be expected and the mucosa is more sensitive.…”

Section: Permeability Enhancers -Risks and Benefitsmentioning

confidence: 99%

Innovative pharmaceutical formulations and excipients for nasal delivery of drugs to target the systemic circulation

Kürti¹

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Metabolism of 14C-labelled sucrose esters of stearic acid in rats

Cited by 12 publications

References 9 publications

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

Regioselective Synthesis of Lactulose Esters by Candida antarctica and Thermomyces lanuginosus Lipases

Development of a quantitative GC-FID method for the determination of sucrose mono- and diesters in foods

Innovative pharmaceutical formulations and excipients for nasal delivery of drugs to target the systemic circulation

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