Formation of N-(Carboxymethyl)fumonisin B1, Following the Reaction of Fumonisin B1 with Reducing Sugars

Howard, Paul C.; Churchwell, Mona I.; Couch, Letha H.; Marques, M. Matilde; Doerge, Daniel R.

doi:10.1021/jf980194q

Cited by 86 publications

(90 citation statements)

References 36 publications

(43 reference statements)

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“…Only one product was observed from this reaction probably because the HPLC separated it from other potential nonenzymatic browning reaction products. The shorter reaction time (42) than that used here may have resulted in fewer reaction products in their reaction mixture. Poling et al (41) reported N-carboxymethyl-fumonisin B 1 as a secondary product from this reaction.…”

Section: Resultsmentioning

confidence: 95%

“…Poling et al (41) have identified this first product of fumonisin B 1 -glucose condensation as N-(deoxy-D-fructosyl-1-yl) fumonisin B 1 , the Amadori rearrangement product expected from glucose, with the same MW reported here. Howard et al (42) claimed that there was only one primary product, N-carboxymethyl-fumonisin B 1 , with a molecular weight of 779 when fumonisin B 1 reacted with D-glucose at 78°C for about 13 h. Their reaction products were separated with reversed-phase HPLC, and the HPLC column eluant was delivered to the mass spectrometer. Only one product was observed from this reaction probably because the HPLC separated it from other potential nonenzymatic browning reaction products.…”

Section: Resultsmentioning

confidence: 99%

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Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Clifford

Hauck

et al. 2002

J. Agric. Food Chem.

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The reaction of fumonisin B1 with the reducing sugar D-glucose can block the primary amine group of fumonisin B1 and may detoxify this mycotoxin. A method to separate hundred milligram quantities of fumonisin B1-glucose reaction products from the excess D-glucose with a reversed-phase C18 cartridge was developed. Mass spectrometry revealed that there were four primary products in this chain reaction when fumonisin B1 was heated with D-glucose at 65 C for 48 h: N-methyl-fumonisin B1, N-carboxymethylfumonisin B1, N-(3-hydroxyacetonyl)-fumonisin B1, and N-(2-hydroxy, 2-car-boxyethyl)-fumonisin B1. The N-(1-deoxy-D-fructos-1-yl) fumonisin B1 (fumonisin B1-glucose Schiff 's base) was detected by mass spectrometry when fumonisin B1 was heated with D-glucose at 60 C. The nonenzymatic browning reaction of fumonisin B1 with excess D-glucose followed apparent first-order kinetics. The activation energy, Ea, was 105.7 kJ/mol. RightsOn-time permission is granted only for the use specified in your request. No additional uses are granted (such as derivative works or other editions). AuthorsYun Lu, Laura Clifford, Catherine C.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Clifford

Hauck

et al. 2002

J. Agric. Food Chem.

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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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“…Fumonisins are also found to be relatively heat stable (Alberts et al, 1990;Howard et al, 1998) and light stable (IARC, 1993). They are also stable in stored products when these are kept in airtight at very low temperatures (Gelderblom et al, PROMEC Unit, Medical Research Council, Tygerberg, South Africa, 2002, unpublished data), or γ-irradiated .…”

Section: Fumonisins and Their Toxicological Effectsmentioning

confidence: 99%

Infection of maize by Fusarium species and contamination with fumonisin in africa

Fandohan¹,

Hell²,

Marasas³

et al. 2003

Afr. J. Biotechnol.

119

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Fusarium is one of the major fungal genera associated with maize in Africa. This genus comprises several toxigenic species including F. verticillioides and F. proliferatum, which are the most prolific producers of fumonisins. The fumonisins are a group of economically important mycotoxins and very common contaminants of maize-based foods and feeds throughout the world. They have been found to be associated with several animal diseases such as leukoencephalomalacia in horses and pulmonary oedema in pigs. Effects of fumonisins on humans are not yet well understood. However, their occurrence in maize has been associated with high incidences of oesophageal and liver cancer. Infection of maize by Fusarium species and contamination with fumonisins are generally influenced by many factors including environmental conditions (climate, temperature, humidity), insect infestation and pre-and postharvest handling. Attempts to control F. verticillioides and to detoxify or reduce fumonisin levels in maize have been undertaken. However, more research studies are urgently needed in order to understand more about this toxin. Fumonisins are less documented because they are recently discovered mycotoxins compared to aflatoxins. To date in Africa, apart from South Africa, very little information is available on Fusarium infection and fumonisin contamination in maize. It is a matter of great concern that on this continent, millions of people are consuming contaminated maize and maize-based foods daily without being aware of the danger.

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Formation of N-(Carboxymethyl)fumonisin B₁, Following the Reaction of Fumonisin B₁ with Reducing Sugars

Cited by 86 publications

References 36 publications

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Glucose Reaction with Fumonisin B₁Partially Reduces Its Toxicity in Swine

Infection of maize by Fusarium species and contamination with fumonisin in africa

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Formation of N-(Carboxymethyl)fumonisin B1, Following the Reaction of Fumonisin B1 with Reducing Sugars

Cited by 86 publications

References 36 publications

Characterization of Fumonisin B1−Glucose Reaction Kinetics and Products

Characterization of Fumonisin B1−Glucose Reaction Kinetics and Products

Glucose Reaction with Fumonisin B1Partially Reduces Its Toxicity in Swine

Infection of maize by Fusarium species and contamination with fumonisin in africa

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Product

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Formation of N-(Carboxymethyl)fumonisin B₁, Following the Reaction of Fumonisin B₁ with Reducing Sugars

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Characterization of Fumonisin B₁−Glucose Reaction Kinetics and Products

Glucose Reaction with Fumonisin B₁Partially Reduces Its Toxicity in Swine