Effects of Sterylglycosides from Soybean on Lipid Indices in the Plasma, Liver, and Feces of Rats

Murui, Takeo; Yasukawa, Masaki; Takeuchi, Hiroyuki; Fujii, Shigeki; Mizobuchi, Haruki; Takeuchi, Hisanao

doi:10.1271/bbb.58.494

Cited by 15 publications

(5 citation statements)

References 10 publications

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“…The greatest decline in the TAG concentration was also observed under the influence of lecithin and long-chain n-3 PUFA. Iwata et al (1993) found that soyabean lecithin reduced cholesterol absorption in the small intestine, while Tateo et al (1994) found that the addition of 5% soyabean lecithin to the diet increased the excretion of TCh and lipids in faeces. In our experiment lecithin did not differentiate TCh in the serum of rats fed rape seed oil, which would support the hypothesis that serum TCh levels are related to increased elimination of TCh.…”

Section: Polyunsaturated Fatty Acids N-3 Pufamentioning

confidence: 99%

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

Sawosz¹,

Chachulowa²,

Lechowski³

et al. 1999

J. Anim. Feed Sci.

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Forty-eight (Wistar) rats were divided into 3 groups and fed semi-synthetic diets containing various types of fat (6%): rape seed, linseed, or fish oil. Half of the animals in each group received lecithin (5% of the mixture). The content of fatty acids in the serum and m. longissimus dorsi was determined, as well as serum triacylglyccrides (TAG) and total cholesterol (TCh). It was found that feeding fish oil increased the percentage of eicosapentaenoic (EPA) and docosahexaenoic (DHA) acids in the serum and muscle tissue, while the addition of linseed oil increased the content of a-linolenic acid and EPA in these tissues. The addition of lecithin raised the percentage of serum linoleic acid and decreased, EPA and DHA. TAG and TCh concentrations were much lower in the animals receiving lecithin and fish oil in their diets and, to a lesser degree, also in those receiving linseed oil, in comparison with rats fed rape seed oil.

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Section: Polyunsaturated Fatty Acids N-3 Pufamentioning

confidence: 99%

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

Sawosz¹,

Chachulowa²,

Lechowski³

et al. 1999

J. Anim. Feed Sci.

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“…Determining the composition of sterol profiles is important as physiological and pharmacological properties such as intestinal absorption, metabolic fate, and bioactivity may be influenced by the sterol structure as was observed with FS (Ling and Jones, 1995 ) emphasizing the necessity for full structural knowledge. In case of SG, bioactive properties of glycosylated sterols, such as the reduction of intestinal cholesterol absorption and modulation of immune system, have been investigated with a primary focus on sitosteryl glucoside (Tateo et al, 1994 ; Bouic et al, 1996 ; Lee et al, 2007 ; Lin et al, 2009 ; Kim et al, 2013 ; Chávez-Santoscoy et al, 2014 ; Yang and An, 2014 ). To effectively study structure-activity relationships also for SG in the future, it is important to know the correct SG profiles of plants and to find sources for various SG including minor species.…”

Section: Introductionmentioning

confidence: 99%

UPLC-MS/MS Based Identification of Dietary Steryl Glucosides by Investigation of Corresponding Free Sterols

2018

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Dietary plant foods are characterized by a vast molecular diversity of glycosylated sterols (SG) that differ in the structure of the steryl backbone. The identification of these polar steryl conjugates represents a major challenge as they are structurally highly similar, and commercial standards are limited to a few naturally abundant species. Spectral databases do not yet contain MS/MS spectra of these sterol conjugates obtained by electrospray ionization (ESI), which would facilitate their reliable identification. Thus, this study aimed at providing novel information on ESI-MS/MS spectra of both abundant and minor SG found in foods. As a first step, however, free sterols (FS) were investigated for their fragmentation behavior as they share the same intermediate ion as SG. Pure SG were obtained from commercially available standard mixtures and minor SG were extracted from different food sources (oat bran, wheat bran, pumpkin seeds, melon, rapeseeds, and potato peel). ESI-MS/MS spectra of 15 FS were assessed and fragment ions reflective of structural features were identified and rationalized. Subsequently, 14 SG were identified at four different levels, while relative retention times from chromatographic separation and spectral features of FS served to identify five SG. Spectral data from FS were directly transferable to SG when analyzed as aglycone ions as shown by similarity scores while SG were characterized by shorter retention times in reverse phase chromatography and the additional analysis as sodiated adduct confirmed their glycosidic nature. Moreover, we report for the first time the occurrence of 24-methylenecholesterol and a 4-monomethyl sterol as glycosidic conjugates in higher plants. The presented data will serve as a valuable tool for SG profiling of foods by facilitating their identification.

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“…Health claims about the ability of FS and their esters to reduce the risk of cardiovascular disease have been accepted by both the European Food Safety Authority (EFSA) and the US Food and Drug Administration (FDA) [5,6]. Glycosylated sterols have been shown to reduce cholesterol absorption even though the glycosidic bond is not cleaved during digestion [7,8]. Furthermore, health benefits, such as modulation of the immune system and reduction of prostate hyperplasia, have been attributed to SG [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Comparison of Enzymatic Hydrolysis and Acid Hydrolysis of Sterol Glycosides from Foods Rich in Δ⁷‐Sterols

Münger

Jutzi

Lampi

et al. 2015

Lipids

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In this study, we present the difference in sterol composition of extracted steryl glycosides (SG) hydrolyzed by either enzymatic or acid hydrolysis. SG were analyzed from foods belonging to the plant families Cucurbitaceae (melon and pumpkin seeds) and Amaranthaceae (amaranth and beetroot), both of which are dominated by Δ(7)-sterols. Released sterols were quantified by gas chromatography with a flame ionization detector (GC-FID) and identified using gas chromatography/mass spectrometry (GC-MS). All Δ(7)-sterols identified (Δ(7)-stigmastenyl, spinasteryl, Δ(7)-campesteryl, Δ(7)-avenasteryl, poriferasta-7,25-dienyl and poriferasta-7,22,25-trienyl glucoside) underwent isomerization under acidic conditions and high temperature. Sterols with an ethylidene or methylidene side chain were found to form multiple artifacts. The artifact sterols coeluted with residues of incompletely isomerized Δ(7)-sterols, or Δ(5)-sterols if present, and could be identified as Δ(8(14))-sterols on the basis of relative retention time, and their MS spectra as trimethylsilyl (TMS) and acetate derivatives. For instance, SG from melon were composed of 66% Δ(7)-stigmastenol when enzymatic hydrolysis was performed, whereas with acid hydrolysis only 8% of Δ(7)-stigmastenol was determined. The artifact of Δ(7)-stigmastenol coeluted with residual non-isomerized spinasterol, demonstrating the high risk of misinterpretation of compositional data obtained after acid hydrolysis. Therefore, the accurate composition of SG from foods containing sterols with a double bond at C-7 can only be obtained by enzymatic hydrolysis or by direct analysis of the intact SG.

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Effects of Sterylglycosides from Soybean on Lipid Indices in the Plasma, Liver, and Feces of Rats

Cited by 15 publications

References 10 publications

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

UPLC-MS/MS Based Identification of Dietary Steryl Glucosides by Investigation of Corresponding Free Sterols

Comparison of Enzymatic Hydrolysis and Acid Hydrolysis of Sterol Glycosides from Foods Rich in Δ⁷‐Sterols

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Effects of Sterylglycosides from Soybean on Lipid Indices in the Plasma, Liver, and Feces of Rats

Cited by 15 publications

References 10 publications

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

Influence of dietary lecithin and oils rich in n-3 polyunsaturated fatty acids (PUFA) on the fatty acid content of rat muscle and serum

UPLC-MS/MS Based Identification of Dietary Steryl Glucosides by Investigation of Corresponding Free Sterols

Comparison of Enzymatic Hydrolysis and Acid Hydrolysis of Sterol Glycosides from Foods Rich in Δ7‐Sterols

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Product

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Comparison of Enzymatic Hydrolysis and Acid Hydrolysis of Sterol Glycosides from Foods Rich in Δ⁷‐Sterols