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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

Detection and identification of NDfrc-FB1. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 14.87 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 400–410) obtained at 14.87 min (scan event 1) (C).
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toxins-07-03700-f002: Detection and identification of NDfrc-FB1. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 14.87 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 400–410) obtained at 14.87 min (scan event 1) (C).

Mentions: Authors first confirmed the existence of FB1 and NDfrc-FB1 in the corn powder extract, based on the full scan results using the calculated masses. In the full scan data (scan event 1), peaks corresponding to the monitor ions [FB1−H]− (720.3812) and [NDfrc-FB1−H]− (882.4340) were detected at 15.09 min and 14.87 min, respectively. The same peaks were observed when standard FB1 and authentic NDfrc-FB1 were injected into the LC-MS system. Regarding detection of NDfrc-FB1, abundant [NDfrc-FB1−H]− (882.4349) ion was detected with a deviation of 0.92 mmu (1.04 ppm) (Figure 2B). In addition, the fragment ions [NDfrc-FB1−TCAK−H]− (724.4136), [NDfrc-FB1−Glc−H]− (720.3824), [NDfrc-FB1−Glc−TCAK−H]− (562.3607), and [NDfrc-FB1−Glc−2TCAK−H]− (404.3378) were observed, with deviations of 1.14 mmu (1.58 ppm), 1.19 mmu (1.65 ppm), 0.99 mmu (1.67 ppm) and −0.32 mmu (−0.78 ppm), respectively (Figure 2B,C). During the scan event 2, the latter two fragment ions, as well as [TCAK−H]− (157.0138) provided dual peaks (at 15.11 min and 14.88 min) (Figure 2A, Table 1), indicating that similar fragmentation was occurring for FB1 and NDfrc-FB1. Although [NDfrc-FB1−2TCAK−H]− (408.3695) was suggested as a fragment of NDfrc-FB1 (Table 1), a corresponding ion was not detected for NDfrc-FB1 (chemically synthesized or contained in corn extract). The observed mass values and their respective mass deviations from the calculated values are summarized in Table 1.


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)

Detection and identification of NDfrc-FB1. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 14.87 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 400–410) obtained at 14.87 min (scan event 1) (C).
© Copyright Policy
Related In: Results  -  Collection

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

toxins-07-03700-f002: Detection and identification of NDfrc-FB1. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 14.87 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 400–410) obtained at 14.87 min (scan event 1) (C).
Mentions: Authors first confirmed the existence of FB1 and NDfrc-FB1 in the corn powder extract, based on the full scan results using the calculated masses. In the full scan data (scan event 1), peaks corresponding to the monitor ions [FB1−H]− (720.3812) and [NDfrc-FB1−H]− (882.4340) were detected at 15.09 min and 14.87 min, respectively. The same peaks were observed when standard FB1 and authentic NDfrc-FB1 were injected into the LC-MS system. Regarding detection of NDfrc-FB1, abundant [NDfrc-FB1−H]− (882.4349) ion was detected with a deviation of 0.92 mmu (1.04 ppm) (Figure 2B). In addition, the fragment ions [NDfrc-FB1−TCAK−H]− (724.4136), [NDfrc-FB1−Glc−H]− (720.3824), [NDfrc-FB1−Glc−TCAK−H]− (562.3607), and [NDfrc-FB1−Glc−2TCAK−H]− (404.3378) were observed, with deviations of 1.14 mmu (1.58 ppm), 1.19 mmu (1.65 ppm), 0.99 mmu (1.67 ppm) and −0.32 mmu (−0.78 ppm), respectively (Figure 2B,C). During the scan event 2, the latter two fragment ions, as well as [TCAK−H]− (157.0138) provided dual peaks (at 15.11 min and 14.88 min) (Figure 2A, Table 1), indicating that similar fragmentation was occurring for FB1 and NDfrc-FB1. Although [NDfrc-FB1−2TCAK−H]− (408.3695) was suggested as a fragment of NDfrc-FB1 (Table 1), a corresponding ion was not detected for NDfrc-FB1 (chemically synthesized or contained in corn extract). The observed mass values and their respective mass deviations from the calculated values are summarized in Table 1.

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