Characterization of Fumonisin B<sub>1</sub>−Glucose Reaction Kinetics and Products

Lu, Yun; Clifford, Laura J.; Hauck, Catherine C.; Hendrich, Suzanne; Osweiler, Gary D.; Murphy, Patricia A.

doi:10.1021/jf020134r

Cited by 46 publications

(43 citation statements)

References 42 publications

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“…The structure of NCM-FB 1 was identified by Howard et al [99]. It has been shown in model experiments that, under moderate conditions, heating (60 -808C) 20 mM (or 100 mM) glucose (or other reducing sugars) and 0.25 mM (or 1.39 mM) FB 1 in potassium phosphate buffer (pH 7 -7.5) results in the formation of NCM-FB 1 [99,100]. It was suggested that the reaction proceeds, as a stable Schiff base is created, through a common Maillard reaction (for reviews see [101,102]) between FB 1 (an aliphatic primary amine) and a reducing sugar [103].…”

Section: Fumonisin Reaction Products and Matrix Bindingmentioning

confidence: 99%

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Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Humpf

Voss

2004

Molecular Nutrition Food Res

172

104

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Fumonisins are Fusarium mycotoxins that occur in corn and corn-based foods. They are toxic to animals and at least one analogue, fumonisin B1, is carcinogenic to rodents. Their effect on human health is unclear, however, fumonisins are considered to be risk factors for cancer and possibly neural tube defects in some heavily exposed populations. It is therefore important to minimize exposures in these populations. Cleaning corn to remove damaged or moldy kernels reduces fumonisins in foods while milling increases their concentration in some and reduces their concentration in other products. Fumonisins are water-soluble and nixtamalization (cooking in alkaline water) lowers the fumonisin content of food products if the cooking liquid is discarded. Baking, frying, and extrusion cooking of corn at high temperatures ( > or = 190 degrees C) also reduces fumonisin concentrations in foods, with the amount of reduction achieved depending on cooking time, temperature, recipe, and other factors. However, the chemical fate of fumonisins in baked, fried, and extruded foods is not well understood and it is not known if the reduced concentrations result from thermal decomposition of fumonisins or from their binding to proteins, sugars or other compounds in food matrices. These possibilities might or might not be beneficial depending upon the bioavailability and inherent toxicity of decomposition products or the degree to which bound fumonisins are released in the gastrointestinal tract. In this review the affects of cooking and processing on the concentration and chemical structure of fumonisins as well as the toxicological consequences of known and likely fumonisin reaction products are discussed.

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Section: Fumonisin Reaction Products and Matrix Bindingmentioning

confidence: 99%

“…Following the general Maillard reaction scheme [101,102], it is assumed that NDF-FB 1 is further converted to NCM-FB 1 (Fig. 2, reaction C) [99,100]. Intermediates formed during the rearrangement of NDF-FB 1 to NCM-FB 1 have recently been identified [100].…”

Section: Fumonisin Reaction Products and Matrix Bindingmentioning

confidence: 99%

Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Humpf

Voss

2004

Molecular Nutrition Food Res

172

104

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“…The brown color of samples after extrusion suggested that loss of FB 1 might be due to the NEB reaction (21,22). The products of the FB 1 -glucose chain reaction were recently characterized as N-carboxymethylfumonisin B 1 (23,24) (24).…”

Section: Introductionmentioning

confidence: 99%

Glucose Reaction with Fumonisin B₁Partially Reduces Its Toxicity in Swine

Fernandez-Surumay

Osweiler

Yaeger

et al. 2004

J. Agric. Food Chem.

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Acute and subacute intraperitoneal doses of fumonisin B1 (FB1) were administered to test the efficacy of the FB1-glucose reaction products in detoxifying FB1 in swine. In the acute study at 11 µmol of FB1/kg of body weight, five of six pigs administered FB1 and four of six pigs administered FB1-glucose died from acute pulmonary edema. Analysis of weight gain, serum aspartate aminotransferase and γ-glutamyltransferase, total cholesterol, and pathological evaluation did not provide evidence of protection against FB1 toxicity by the FB1-glucose reaction products. In the subacute study at 5.5 µmol of FB1/kg of body weight, one pig administered FB1 died from liver damage. Analysis of serum aspartate aminotransferase, γ-glutamyltransferase, and total bilirubin showed protection against FB1 toxicity by the FB1-glucose reaction products. The levels of sphinganine and sphinganine/sphingosine ratios in serum and liver as well as pathologic findings provided definitive evidence of protection against the FB1 toxic effects by this detoxification procedure (p < 0.05). Acute and subacute intraperitoneal doses of fumonisin B 1 (FB 1 ) were administered to test the efficacy of the FB 1 -glucose reaction products in detoxifying FB 1 in swine. In the acute study at 11 µmol of FB 1 /kg of body weight, five of six pigs administered FB 1 and four of six pigs administered FB 1 -glucose died from acute pulmonary edema. Analysis of weight gain, serum aspartate aminotransferase and γ-glutamyltransferase, total cholesterol, and pathological evaluation did not provide evidence of protection against FB 1 toxicity by the FB 1 -glucose reaction products. In the subacute study at 5.5 µmol of FB 1 /kg of body weight, one pig administered FB 1 died from liver damage. Analysis of serum aspartate aminotransferase, γ-glutamyltransferase, and total bilirubin showed protection against FB 1 toxicity by the FB 1 -glucose reaction products. The levels of sphinganine and sphinganine/sphingosine ratios in serum and liver as well as pathologic findings provided definitive evidence of protection against the FB 1 toxic effects by this detoxification procedure (p < 0.05).

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“…The centrifuged extract was loaded onto a C 18 Sep-pak cartridge (Waters), washed with 5 mL of water/acetonitrile (4:1), and eluted with exactly 2 mL of acetonitrile/ water (7:3). Fumonisins B 1 and B2 were detected as derivatives with o-phthaldialdehyde following reversed-phase HPLC separation by fluorescence detection (22). One hundred microliters of sample extract was mixed with 100 µL of 50 mM potassium phosphate buffer, pH 8.3, and 100 µL of o-phthaldialdehyde solution (5 mg of o-phthaldialdehyde and 10 µL of 2-mercaptoethanol in 5 mL of acetonitrile) at room temperature.…”

Section: Methodsmentioning

confidence: 99%

“…This strategy was later used in an animal study where diethylnitrosamine (DEN)-initiated Fischer344/N rats treated with FB 1 -fructose showed a significant reduction in cancer promotion when compared to rats treated with only FB 1 (21). The products of the FB 1 -glucose chain reaction were chemically characterized as N-carboxymethylfumonisin B 1 (22,23), N-(1-deoxy-D-fructos-1-yl)fumonisin B 1 (22,24), N-methylfumonisin B 1 , N-(3-hydroxyacetonyl)fumonisin B 1 , and N-(2-hydroxy-2-carboxyethyl)fumonisin B 1 (22) (Figure 1). One of these products, N-carboxymethylfumonisin B 1 , was found to be nontoxic in female B6C3F mice fed diets at 140 µmol/kg of diet (25).…”

Section: Introductionmentioning

confidence: 99%

Fumonisin B−Glucose Reaction Products Are Less Toxic When Fed to Swine

Fernandez-Surumay

Osweiler²,

Yaeger³

et al. 2005

J. Agric. Food Chem.

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The effects of fumonisin B-glucose reaction products in swine diets was examined. Pigs were fed diets containing 528 µmol of total fumonisin B/kg (FB), 528 µmol of total FB-glucose adducts/kg (FB-G, 122 µmol of unreacted FB/kg), or 0 µmol of total FB/kg for 15 days to test the efficacy of the FB-G reaction products in detoxifying FB. Weight gain in FB pigs was lower than in FB-G or controls, which was correlated with feed intake reduction in FB pigs. Serum aspartate aminotransferase, γ-glutamyltransferase, and total bilirubin in FB pigs were higher than in FB-G or control pigs. Serum sphinganine/shingosine ratios in FB pigs were higher than in FB-G or control pigs. Microscopic examination of tissues from FB pigs showed generalized liver necrosis and apoptosis with marked cellular pleomorphism and disorganized hepatic cords. The liver and kidneys in the FB-G group appeared to be normal. Tissues of controls were free of lesions. Results suggest that dietary FB-G products are less toxic to swine and may provide an detoxification approach in instances of widespread FB grain contamination (p < 0.05). KeywordsInterdepartmental The effects of fumonisin B-glucose reaction products in swine diets was examined. Pigs were fed diets containing 528 µmol of total fumonisin B/kg (FB), 528 µmol of total FB-glucose adducts/kg (FB-G, 122 µmol of unreacted FB/kg), or 0 µmol of total FB/kg for 15 days to test the efficacy of the FB-G reaction products in detoxifying FB. Weight gain in FB pigs was lower than in FB-G or controls, which was correlated with feed intake reduction in FB pigs. Serum aspartate aminotransferase, γ-glutamyltransferase, and total bilirubin in FB pigs were higher than in FB-G or control pigs. Serum sphinganine/shingosine ratios in FB pigs were higher than in FB-G or control pigs. Microscopic examination of tissues from FB pigs showed generalized liver necrosis and apoptosis with marked cellular pleomorphism and disorganized hepatic cords. The liver and kidneys in the FB-G group appeared to be normal. Tissues of controls were free of lesions. Results suggest that dietary FB-G products are less toxic to swine and may provide an detoxification approach in instances of widespread FB grain contamination (p < 0.05).

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Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Cited by 46 publications

References 42 publications

Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Glucose Reaction with Fumonisin B₁Partially Reduces Its Toxicity in Swine

Fumonisin B−Glucose Reaction Products Are Less Toxic When Fed to Swine

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Characterization of Fumonisin B1−Glucose Reaction Kinetics and Products

Cited by 46 publications

References 42 publications

Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Effects of thermal food processing on the chemical structure and toxicity of fumonisin mycotoxins

Glucose Reaction with Fumonisin B1Partially Reduces Its Toxicity in Swine

Fumonisin B−Glucose Reaction Products Are Less Toxic When Fed to Swine

Contact Info

Product

Resources

About

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Glucose Reaction with Fumonisin B₁Partially Reduces Its Toxicity in Swine