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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 and NDfrc-FB3 in corn powder extract in comparison with the chemically synthesized species (scan event 1).
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toxins-07-03700-f005: Chromatograms of NDfrc-FB2 and NDfrc-FB3 in corn powder extract in comparison with the chemically synthesized species (scan event 1).

Mentions: In order to confirm the retention time and fragmentation profiles of NDfrc-FB2 and NDfrc-FB3 during the LC-Orbitrap MS analysis, these compounds were chemically synthesized with the standards of FB2 and FB3 with reference to the Poling et al. [18] report. Figure 5 shows the chromatograms of NDfrc-FB2 and NDfrc-FB3 in the corn powder extract and for chemically synthesized species. The mass fragmentation profiles of the synthesized NDfrc-FB2 (NDfrc-FB3) were in agreement with those of NDfrc-FB2 (NDfrc-FB3) detected in the corn sample extract (Figure S1). These results indicate that NDfrc-FB2 (and NDfrc-FB3) appear to be formed though a non-enzymatic reaction between FB2 (and FB3) and D-glucose. In addition, these synthesized NDfrc-FB2 and NDfrc-FB3 did not react with the OPA reagent (details not shown). Because the synthesized NDfrc-FB2 (and NDfrc-FB3) were not sufficiently pure, and contained remaining FB2 (and FB3), they could not be used for performing the quantitative analysis.


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 and NDfrc-FB3 in corn powder extract in comparison with the chemically synthesized species (scan event 1).
© Copyright Policy
Related In: Results  -  Collection

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

toxins-07-03700-f005: Chromatograms of NDfrc-FB2 and NDfrc-FB3 in corn powder extract in comparison with the chemically synthesized species (scan event 1).
Mentions: In order to confirm the retention time and fragmentation profiles of NDfrc-FB2 and NDfrc-FB3 during the LC-Orbitrap MS analysis, these compounds were chemically synthesized with the standards of FB2 and FB3 with reference to the Poling et al. [18] report. Figure 5 shows the chromatograms of NDfrc-FB2 and NDfrc-FB3 in the corn powder extract and for chemically synthesized species. The mass fragmentation profiles of the synthesized NDfrc-FB2 (NDfrc-FB3) were in agreement with those of NDfrc-FB2 (NDfrc-FB3) detected in the corn sample extract (Figure S1). These results indicate that NDfrc-FB2 (and NDfrc-FB3) appear to be formed though a non-enzymatic reaction between FB2 (and FB3) and D-glucose. In addition, these synthesized NDfrc-FB2 and NDfrc-FB3 did not react with the OPA reagent (details not shown). Because the synthesized NDfrc-FB2 (and NDfrc-FB3) were not sufficiently pure, and contained remaining FB2 (and FB3), they could not be used for performing the quantitative analysis.

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