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Ramos-Romero S.,CSIC - Institute of Advanced Chemistry of Catalonia | Molinar-Toribio E.,CSIC - Institute of Advanced Chemistry of Catalonia | Gomez L.,Bioglane SLNE | Perez-Jimenez J.,CSIC - Institute of Advanced Chemistry of Catalonia | And 4 more authors.
Obesity | Year: 2014

Objective Becoming overweight has been related to elevated levels of Enterobacteriales in the gut. d-Fagomine is an iminosugar that has been shown to selectively agglutinate Enterobacteriales in vitro. The goal of this work is to establish whether d-fagomine exerts a similar effect in vivo and whether this has any downstream consequences on weight gain. Methods The rats were fed a high-fat high-sucrose diet (HFHS) supplemented with d-fagomine (or not; for comparison) or a standard diet for 5 weeks. The levels of total bacteria, Enterobacteriales and Escherichia coli were determined in fecal samples by performing quantitative real-time polymerase chain reactions on DNA. Results Whereas the total levels of bacteria were independent of the diet, rats fed HFHS (without d-fagomine) excreted significantly higher proportions of Enterobacteriales and E. coli than those fed a standard diet. The levels of Enterobacteriales and E. coli of the rats given HFHS with d-fagomine were similar to those of the rats fed a standard diet. Compared to the standard group, rats fed HFHS with d-fagomine gained significantly less weight (15.3%) than those fed HFHS (20.9%). Conclusion d-Fagomine reduces the amount of Enterobacteriales excreted by rats fed HFHS and this may help to avert becoming obese. Copyright © 2013 The Obesity Society.

Molinar-Toribio E.,CSIC - Institute of Advanced Chemistry of Catalonia | Perez-Jimenez J.,CSIC - Institute of Advanced Chemistry of Catalonia | Ramos-Romero S.,CSIC - Institute of Advanced Chemistry of Catalonia | Ramos-Romero S.,CIBER ISCIII | And 8 more authors.
Food and Function | Year: 2015

d-Fagomine is a natural iminosugar that counteracts the short-term effects of a high-energy-dense diet on body weight, fasting blood glucose levels and the proportion of gut Enterobacteriales. This suggests that supplementation with d-fagomine for longer periods may delay the onset of other factors related to metabolic syndrome. Here we evaluate the effects of d-fagomine dietary supplementation on relevant metabolic hormones and lipid peroxidation. Adult Sprague-Dawley rats were fed a high-fat high-sucrose diet supplemented or not with d-fagomine (0.065% w/w) for 9 weeks. Weight gain, plasma triglycerides, glucose, insulin, glucagon, ghrelin, leptin, and urine F2-isoprostanes were evaluated. d-Fagomine attenuated the changes induced by the high-energy-dense diet in triglycerides and all the hormones tested. These results suggest that d-fagomine may help to avert the complications associated with unhealthy eating by counteracting the effects of high-energy-dense diets during the early stages of the development of metabolic disorders. This journal is © The Royal Society of Chemistry.

Amezqueta S.,Bioglane SLNE | Galan E.,Bioglane SLNE | Vila-Fernandez I.,Bioglane SLNE | Pumarola S.,Bioglane SLNE | And 6 more authors.
Food Chemistry | Year: 2013

Buckwheat (Fagopyrum esculentum Moench) groats contain the iminosugar d-fagomine as a minor component that might contribute to the alleged health benefits of this pseudo-cereal. This study presents analysis of d-fagomine in buckwheat-based foodstuffs by liquid chromatography coupled to mass spectrometry and an estimation of its presence in the human diet based on a published population-based cross-sectional nutrition survey. d-Fagomine is present in common buckwheat-based foodstuffs in amounts ranging from 1 to 25 mg/kg or mg/L, it is stable during boiling, baking, frying and fermentation, and it is biosynthesised upon sprouting. The estimated total intake of d-fagomine resulting from a diet that includes such foodstuffs would be between 3 and 17 mg per day (mean for both genders; range from P5 to P95). A diet rich in buckwheat products would provide a daily amount of d-fagomine that may in part explain the beneficial properties traditionally attributed to buckwheat consumption. © 2012 Elsevier Ltd. All rights reserved.

Amezqueta S.,Bioglane SLNE | Galan E.,Bioglane SLNE | Fuguet E.,CSIC - Institute of Advanced Chemistry of Catalonia | Fuguet E.,University of Barcelona | And 3 more authors.
Analytical and Bioanalytical Chemistry | Year: 2012

D-Fagomine is an iminosugar first found in buckwheat (Fagopyrum esculentum Moench) which if used as a dietary supplement or functional food component may reduce the risks of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria. As D-fagomine may become increasingly important to the food industry, a reliable analytical method for its determination in natural plant sources and foodstuffs is desirable. We have devised a method to separate D-fagomine from its diastereomers 3-epi-fagomine and 3,4-di-epi-fagomine in a single run by cation exchange high-performance liquid chromatography (HPLC) with detection and quantification by mass spectrometry using electrospray ionisation and a simple quadrupole analyser (ESI-Q-MS). The method is validated and applied to the determination of D-fagomine in buckwheat groats (6.7-44 mg kg ?1), leaves, bran and flour.We show that buckwheat contains 3,4-di-epi-fagomine (1.0-43 mg kg ?1), which has not previously been reported in this source. The procedure is also applied to mulberry (Morus alba) leaves, which contain D-fagomine and 3-epi-fagomine as minor components. The new method provides a means for convenient and accurate determination of D-fagomine in plant samples and foodstuffs.© 2011 Springer-Verlag.

Gomez L.,Bioglane SLNE | Molinar-Toribio E.,CSIC - Institute of Advanced Chemistry of Catalonia | Calvo-Torras M.A.,Autonomous University of Barcelona | Adelantado C.,Autonomous University of Barcelona | And 7 more authors.
British Journal of Nutrition | Year: 2012

d-Fagomine is an iminosugar originally isolated from seeds of buckwheat (Fagopyrum sculentum Moench), present in the human diet and now available as a pure crystalline product. We tested d-fagomine for activities connected to a reduction in the risk of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria. The activities were: intestinal sucrase inhibition in vitro (rat mucosa and everted intestine sleeves), modulation of postprandial blood glucose in rats, bacterial agglutination and bacterial adhesion to pig intestinal mucosa. When ingested together with sucrose or starch, d-fagomine lowered blood glucose in a dose-dependent manner without stimulating insulin secretion. d-Fagomine reduced the area under the curve (0-120 min) by 20 % (P < 0•01) and shifted the time to maximum blood glucose concentration (T max) by 15 min at doses of 1-2 mg/kg body weight when administered together with 1 g sucrose/kg body weight. Moreover, d-fagomine (0•14 mm) agglutinated 60 % of Enterobacteriaceae (Escherichia coli, Salmonella enterica serovar Typhimurium) populations (P < 0•01), while it did not show this effect on Bifidobacterium spp. or Lactobacillus spp. At the same concentration, d-fagomine significantly (P < 0•001) inhibited the adhesion of Enterobacteriaceae (95-99 % cells in the supernatant) and promoted the adhesion of Lactobacillus acidophilus (56 % cells in the supernatant) to intestinal mucosa. d-Fagomine did not show any effect on bacterial cell viability. Based on all this evidence, d-fagomine may be used as a dietary ingredient or functional food component to reduce the health risks associated with an excessive intake of fast-digestible carbohydrates, or an excess of potentially pathogenic bacteria. © 2011 The Authors.

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