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Detection of N-(1-deoxy-D-fructos-1-yl) Fumonisins B₂ and B₃ in Corn by High-Resolution LC-Orbitrap MS.

Matsuo Y, Takahara K, Sago Y, Kushiro M, Nagashima H, Nakagawa H - Toxins (Basel) (2015)

Bottom Line: The existence of glucose conjugates of fumonisin B₂ (FB₂) and fumonisin B₃ (FB₃) in corn powder was confirmed for the first time.These "bound-fumonisins" (FB₂ and FB₃ bound to glucose) were identified as N-(1-deoxy-D-fructos-1-yl) fumonisin B₂ (NDfrc-FB₂) and N-(1-deoxy-D-fructos-1-yl) fumonisin B₃ (NDfrc-FB₃) respectively, based on the accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS) analysis.Treatment on NDfrc-FB₂ and NDfrc-FB₃ with the o-phthalaldehyde (OPA) reagent also supported that D-glucose binding to FB₂ and FB₃ molecules occurred to their primary amine residues.

View Article: PubMed Central - PubMed

Affiliation: National Agriculture and Food Research Organization (NARO), National Food Research Institute, 2-1-12 Kannon-dai, Tsukuba-shi, Ibaraki 305-8642, Japan. ymatuo@affrc.go.jp.

ABSTRACT
The existence of glucose conjugates of fumonisin B₂ (FB₂) and fumonisin B₃ (FB₃) in corn powder was confirmed for the first time. These "bound-fumonisins" (FB₂ and FB₃ bound to glucose) were identified as N-(1-deoxy-D-fructos-1-yl) fumonisin B₂ (NDfrc-FB₂) and N-(1-deoxy-D-fructos-1-yl) fumonisin B₃ (NDfrc-FB₃) respectively, based on the accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS) analysis. Treatment on NDfrc-FB₂ and NDfrc-FB₃ with the o-phthalaldehyde (OPA) reagent also supported that D-glucose binding to FB₂ and FB₃ molecules occurred to their primary amine residues.

No MeSH data available.


Related in: MedlinePlus

Chromatograms of NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) in corn powder extract before and after the treatment with OPA reagent (scan event 1).
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toxins-07-03700-f004: Chromatograms of NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) in corn powder extract before and after the treatment with OPA reagent (scan event 1).

Mentions: Figure 4 shows the LC-MS chromatograms of the NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) detected in the corn powder extract before and after treatment with OPA reagent (scan event 1). If the structures of NDfrc-FB2 and NDfrc-FB3 were similar to that of NDfrc-FB1 (glucose bound to the primary amine of the fumonisin molecule), it was considered that OPA would not react with these species. As shown in Figure 4, the signal intensities of FB2 and FB3 were decreased by the OPA treatment, whereas those of NDfrc-FB2 and NDfrc-FB3 were not. The peak area ratios of NDfrc-FB2 (NDfrc-FB3), before to after the OPA reaction, were 1.44–1.46. On the other hand, these ratios of FB2 (FB3), before to after the OPA reaction were 281.4–1372.1. These results indicate that the primary amine residue was occupied by glucose conjugation in the molecules of NDfrc-FB2 (NDfrc-FB3). The slight shift observed for the fumonisin peaks was attributed to the increase in methanol concentration in the samples following the OPA treatment.


Detection of N-(1-deoxy-D-fructos-1-yl) Fumonisins B₂ and B₃ in Corn by High-Resolution LC-Orbitrap MS.

Matsuo Y, Takahara K, Sago Y, Kushiro M, Nagashima H, Nakagawa H - Toxins (Basel) (2015)

Chromatograms of NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) in corn powder extract before and after the treatment with OPA reagent (scan event 1).
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4591641&req=5

toxins-07-03700-f004: Chromatograms of NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) in corn powder extract before and after the treatment with OPA reagent (scan event 1).
Mentions: Figure 4 shows the LC-MS chromatograms of the NDfrc-FB2 (NDfrc-FB3) and FB2 (FB3) detected in the corn powder extract before and after treatment with OPA reagent (scan event 1). If the structures of NDfrc-FB2 and NDfrc-FB3 were similar to that of NDfrc-FB1 (glucose bound to the primary amine of the fumonisin molecule), it was considered that OPA would not react with these species. As shown in Figure 4, the signal intensities of FB2 and FB3 were decreased by the OPA treatment, whereas those of NDfrc-FB2 and NDfrc-FB3 were not. The peak area ratios of NDfrc-FB2 (NDfrc-FB3), before to after the OPA reaction, were 1.44–1.46. On the other hand, these ratios of FB2 (FB3), before to after the OPA reaction were 281.4–1372.1. These results indicate that the primary amine residue was occupied by glucose conjugation in the molecules of NDfrc-FB2 (NDfrc-FB3). The slight shift observed for the fumonisin peaks was attributed to the increase in methanol concentration in the samples following the OPA treatment.

Bottom Line: The existence of glucose conjugates of fumonisin B₂ (FB₂) and fumonisin B₃ (FB₃) in corn powder was confirmed for the first time.These "bound-fumonisins" (FB₂ and FB₃ bound to glucose) were identified as N-(1-deoxy-D-fructos-1-yl) fumonisin B₂ (NDfrc-FB₂) and N-(1-deoxy-D-fructos-1-yl) fumonisin B₃ (NDfrc-FB₃) respectively, based on the accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS) analysis.Treatment on NDfrc-FB₂ and NDfrc-FB₃ with the o-phthalaldehyde (OPA) reagent also supported that D-glucose binding to FB₂ and FB₃ molecules occurred to their primary amine residues.

View Article: PubMed Central - PubMed

Affiliation: National Agriculture and Food Research Organization (NARO), National Food Research Institute, 2-1-12 Kannon-dai, Tsukuba-shi, Ibaraki 305-8642, Japan. ymatuo@affrc.go.jp.

ABSTRACT
The existence of glucose conjugates of fumonisin B₂ (FB₂) and fumonisin B₃ (FB₃) in corn powder was confirmed for the first time. These "bound-fumonisins" (FB₂ and FB₃ bound to glucose) were identified as N-(1-deoxy-D-fructos-1-yl) fumonisin B₂ (NDfrc-FB₂) and N-(1-deoxy-D-fructos-1-yl) fumonisin B₃ (NDfrc-FB₃) respectively, based on the accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS) analysis. Treatment on NDfrc-FB₂ and NDfrc-FB₃ with the o-phthalaldehyde (OPA) reagent also supported that D-glucose binding to FB₂ and FB₃ molecules occurred to their primary amine residues.

No MeSH data available.


Related in: MedlinePlus