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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-FB2. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 16.40 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 385–395) obtained at 16.40 min (scan event 1) (C).
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toxins-07-03700-f003: Detection and identification of NDfrc-FB2. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 16.40 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 385–395) obtained at 16.40 min (scan event 1) (C).

Mentions: Figure 3 shows the results of screening for NDfrc-FB2 and NDfrc-FB3 in the corn powder extract. Using the same procedure as adopted for NDfrc-FB1, the existence of FB2 and FB3 was first confirmed based on the full scan results (scan event 1) using the calculated mass of [FB2−H]− (704.3863). A major peak corresponding to [FB2−H]− was detected at 16.78 min, as shown at the top of Figure 3A, and the same peak was found for the FB2 standard. As fragment ions of FB2, [FB2−TCAK−H]−, [FB2−2TCAK−H]−, and [TCAK−H]− were observed (Table 2). When the full-scan results (scan event 1) were scrutinised with the calculated mass of [NDfrc-FB2−H]− (866.4391), a major peak was detected for [NDfrc-FB2−H]− at 16.40 min (Figure 3A), and abundant [NDfrc-FB2–H]− (866.4410) was detected with a mass deviation of 1.88 mmu (2.17 ppm) (Figure 3B). In addition, the fragment ions [NDfrc-FB2–TCAK−H]− (708.4188), [NDfrc-FB2−Glc−H]− (704.3875), [NDfrc-FB2−Glc−TCAK−H]− (546.3652), [NDfrc-FB2−Glc−2TCAK−H]− (388.3430) were observed with deviations of 1.24 mmu (1.76 ppm), 1.17 mmu (1.66 ppm), 0.48 mmu (0.88 ppm), and −0.22 mmu (−0.55 ppm), respectively (Figure 3B, Table 2). Due to the low intensities of the signals, several fragment ions (Figure 3C) were observed only in the magnified spectra. Two peaks at 16.79 min and 16.39 min were detected for the monitor ions [NDfrc-FB2−Glc−TCAK−H]− (546.3648) and [NDfrc-FB2−Glc−2TCAK−H]− (388.3432) with scan event 2 (Figure 3A), suggesting that similar fragmentation was occurring for FB2 and NDfrc-FB2. During scan event 2, fragments corresponding to [NDfrc-FB2−TCAK−H]− and [NDfrc-FB2−Glc−2TCAK−H]− were observed (Table 2). The respective mass values of these fragments were 708.4183 mmu and 388.3439 mmu, with mass deviations from the calculated values of 0.70 mmu (0.98 ppm) and 0.70 mmu (1.80 ppm), respectively. In the case of screening for NDfrc-FB3, a major peak for [NDfrc-FB3−H]− was observed at 15.68 min (scan event 1) (Figure 3A), and a fragmentation pattern similar to that of NDfrc-FB2 was also confirmed (details shown in Table 3). There was no difference in the fragmentation patterns of FB2 and FB3, as [FB3−TCAK−H]−, [FB3−2TCAK−H]−, and [TCAK−H]− were observed as the corresponding fragment ions. Based on the data described above, authors were convinced that both NDfrc-FB2 and NDfrc-FB3 were contained in the corn powder extract.


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-FB2. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 16.40 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 385–395) obtained at 16.40 min (scan event 1) (C).
© Copyright Policy
Related In: Results  -  Collection

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

toxins-07-03700-f003: Detection and identification of NDfrc-FB2. Mass chromatogram with scan results (scan events 1 and 2) (A); full mass spectrum obtained at 16.40 min (scan event 1) (B); and mass range magnification of full mass spectrum (m/z: 385–395) obtained at 16.40 min (scan event 1) (C).
Mentions: Figure 3 shows the results of screening for NDfrc-FB2 and NDfrc-FB3 in the corn powder extract. Using the same procedure as adopted for NDfrc-FB1, the existence of FB2 and FB3 was first confirmed based on the full scan results (scan event 1) using the calculated mass of [FB2−H]− (704.3863). A major peak corresponding to [FB2−H]− was detected at 16.78 min, as shown at the top of Figure 3A, and the same peak was found for the FB2 standard. As fragment ions of FB2, [FB2−TCAK−H]−, [FB2−2TCAK−H]−, and [TCAK−H]− were observed (Table 2). When the full-scan results (scan event 1) were scrutinised with the calculated mass of [NDfrc-FB2−H]− (866.4391), a major peak was detected for [NDfrc-FB2−H]− at 16.40 min (Figure 3A), and abundant [NDfrc-FB2–H]− (866.4410) was detected with a mass deviation of 1.88 mmu (2.17 ppm) (Figure 3B). In addition, the fragment ions [NDfrc-FB2–TCAK−H]− (708.4188), [NDfrc-FB2−Glc−H]− (704.3875), [NDfrc-FB2−Glc−TCAK−H]− (546.3652), [NDfrc-FB2−Glc−2TCAK−H]− (388.3430) were observed with deviations of 1.24 mmu (1.76 ppm), 1.17 mmu (1.66 ppm), 0.48 mmu (0.88 ppm), and −0.22 mmu (−0.55 ppm), respectively (Figure 3B, Table 2). Due to the low intensities of the signals, several fragment ions (Figure 3C) were observed only in the magnified spectra. Two peaks at 16.79 min and 16.39 min were detected for the monitor ions [NDfrc-FB2−Glc−TCAK−H]− (546.3648) and [NDfrc-FB2−Glc−2TCAK−H]− (388.3432) with scan event 2 (Figure 3A), suggesting that similar fragmentation was occurring for FB2 and NDfrc-FB2. During scan event 2, fragments corresponding to [NDfrc-FB2−TCAK−H]− and [NDfrc-FB2−Glc−2TCAK−H]− were observed (Table 2). The respective mass values of these fragments were 708.4183 mmu and 388.3439 mmu, with mass deviations from the calculated values of 0.70 mmu (0.98 ppm) and 0.70 mmu (1.80 ppm), respectively. In the case of screening for NDfrc-FB3, a major peak for [NDfrc-FB3−H]− was observed at 15.68 min (scan event 1) (Figure 3A), and a fragmentation pattern similar to that of NDfrc-FB2 was also confirmed (details shown in Table 3). There was no difference in the fragmentation patterns of FB2 and FB3, as [FB3−TCAK−H]−, [FB3−2TCAK−H]−, and [TCAK−H]− were observed as the corresponding fragment ions. Based on the data described above, authors were convinced that both NDfrc-FB2 and NDfrc-FB3 were contained in the corn powder extract.

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