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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

Chemical structures of FBs and their glucose conjugates.
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toxins-07-03700-f001: Chemical structures of FBs and their glucose conjugates.

Mentions: Recently, a glucosylated derivative of deoxynivalenol (DON), DON-3-glucoside (DON3Glc) was found in cereal grain and beer [8,9], and similar compounds have also been found for several other mycotoxins [10,11]. Because these glucosylated derivatives are not detected by conventional analytical methods due to their higher polarity [12,13], they are referred to as “masked (modified) mycotoxins”. Hydrolysis of masked mycotoxins to their aglycons has also been reported [14,15], and it has been suggested that they present an additional potential risk to consumers. In the case of fumonisins, the presence of “bound-fumonisin” has been suggested by several researchers [16,17]. For instance, N-(1-deoxy-d-fructos-1-yl) fumonisin B1 (NDfrc-FB1) was found in corn, and was reportedly formed through a d-glucose binding reaction to the primary amine residue of the FB1 molecule [18]. Although proven under laboratory conditions, the NDfrc-FB1 occurrence at significant levels in processed samples is still controversial [19]. In addition, in vivo stability of this conjugate has not yet been definitively proven [17]. In order to understand the total fumonisin in foods and feeds correctly, there is a need to clarify the presence of these series of fumonisin conjugates. In this paper, authors report the existence of new glucose conjugates derived from type B fumonisins (FB2 and FB3) (Figure 1). These species were detected and identified via high resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS), in combination with treatment using a specific reagent (o-phthalaldehyde, OPA).


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)

Chemical structures of FBs and their glucose conjugates.
© Copyright Policy
Related In: Results  -  Collection

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

toxins-07-03700-f001: Chemical structures of FBs and their glucose conjugates.
Mentions: Recently, a glucosylated derivative of deoxynivalenol (DON), DON-3-glucoside (DON3Glc) was found in cereal grain and beer [8,9], and similar compounds have also been found for several other mycotoxins [10,11]. Because these glucosylated derivatives are not detected by conventional analytical methods due to their higher polarity [12,13], they are referred to as “masked (modified) mycotoxins”. Hydrolysis of masked mycotoxins to their aglycons has also been reported [14,15], and it has been suggested that they present an additional potential risk to consumers. In the case of fumonisins, the presence of “bound-fumonisin” has been suggested by several researchers [16,17]. For instance, N-(1-deoxy-d-fructos-1-yl) fumonisin B1 (NDfrc-FB1) was found in corn, and was reportedly formed through a d-glucose binding reaction to the primary amine residue of the FB1 molecule [18]. Although proven under laboratory conditions, the NDfrc-FB1 occurrence at significant levels in processed samples is still controversial [19]. In addition, in vivo stability of this conjugate has not yet been definitively proven [17]. In order to understand the total fumonisin in foods and feeds correctly, there is a need to clarify the presence of these series of fumonisin conjugates. In this paper, authors report the existence of new glucose conjugates derived from type B fumonisins (FB2 and FB3) (Figure 1). These species were detected and identified via high resolution liquid chromatography-Orbitrap mass spectrometry (LC-Orbitrap MS), in combination with treatment using a specific reagent (o-phthalaldehyde, OPA).

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