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Hiroyuki Nakagawa
Food Research Institute, National Agriculture and Food Research Organization (NARO), 2-1-12 Kannon-dai, Tsukuba-shi, Ibaraki 305-8642, Japan

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Journal article
Published: 02 September 2020 in International Journal of Molecular Sciences
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In the biosynthesis of aflatoxin, verA, ver-1, ordB, and hypA genes of the aflatoxin gene cluster are involved in the pathway from versicolorin A (VA) to demethylsterigmatocystin (DMST). We herein isolated each disruptant of these four genes to determine their functions in more detail. Disruptants of ver-1, ordB, and hypA genes commonly accumulated VA in their mycelia. In contrast, the verA gene disruptant accumulated a novel yellow fluorescent substance (which we named HAMA) in the mycelia as well as culture medium. Feeding HAMA to the other disruptants commonly caused the production of aflatoxins B1 (AFB1) and G1 (AFG1). These results indicate that HAMA pigment is a novel aflatoxin precursor which is involved at a certain step after those of ver-1, ordB, and hypA genes between VA and DMST. HAMA was found to be an unstable substance to easily convert to DMST and sterigmatin. A liquid chromatography-mass spectrometry (LC-MS) analysis showed that the molecular mass of HAMA was 374, and HAMA gave two close major peaks in the LC chromatogram in some LC conditions. We suggest that these peaks correspond to the two conformers of HAMA; one of them would be selectively bound on the substrate binding site of VerA enzyme and then converted to DMST. VerA enzyme may work as a key enzyme in the creation of the xanthone structure of DMST from HAMA.

ACS Style

Hongmei Zeng; Jingjing Cai; Hidemi Hatabayashi; Hiroyuki Nakagawa; Hiromitsu Nakajima; Kimiko Yabe. verA Gene is Involved in the Step to Make the Xanthone Structure of Demethylsterigmatocystin in Aflatoxin Biosynthesis. International Journal of Molecular Sciences 2020, 21, 6389 .

AMA Style

Hongmei Zeng, Jingjing Cai, Hidemi Hatabayashi, Hiroyuki Nakagawa, Hiromitsu Nakajima, Kimiko Yabe. verA Gene is Involved in the Step to Make the Xanthone Structure of Demethylsterigmatocystin in Aflatoxin Biosynthesis. International Journal of Molecular Sciences. 2020; 21 (17):6389.

Chicago/Turabian Style

Hongmei Zeng; Jingjing Cai; Hidemi Hatabayashi; Hiroyuki Nakagawa; Hiromitsu Nakajima; Kimiko Yabe. 2020. "verA Gene is Involved in the Step to Make the Xanthone Structure of Demethylsterigmatocystin in Aflatoxin Biosynthesis." International Journal of Molecular Sciences 21, no. 17: 6389.

Article
Published: 19 July 2020 in Current Microbiology
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Nine domestic wine samples collected from a Japanese winery were examined for the presence of fumonisin B1 (FB1), fumonisin B2 (FB2), and fumonisin B3 (FB3), as well as ochratoxin A (OTA) and ochratoxin B (OTB). Wine samples spiked with 13C-labeled internal standards (13C34-FB1 and 13C20-OTA) were diluted with phosphate buffered saline (PBS) buffer, loaded on immunoaffinity cartridges to purify of fumonisins and ochratoxins, and subjected to liquid chromatography coupled with tandem mass spectrometry (LC–MS/MS) analysis. The data revealed that the domestic wine samples were possibly contaminated with FB1 and FB3, in addition to FB2, whereas none of the tested wine samples were contaminated with OTA and OTB. These results suggest that Fusarium fungi can be associated with the fumonisin contamination of Japanese domestic wine, whereas Aspergillus niger seems to be frequently reported as the major causal fungus of fumonisin contamination of wine in Europe. Analysis of the intermediate samples during the wine brewing indicated that fumonisin concentrations did not increase during wine production, suggesting that fumonisin contamination did not occur during the brewing process, but was derived from the raw materials of grape berries.

ACS Style

Hiroyuki Nakagawa; Ruiko Hashimoto; Yosuke Matsuo; Yuki Sago; Koji Yokoyama; Haruo Takahashi. Detection and Determination of Fumonisins B1, B2, and B3 Contaminating Japanese Domestic Wine by Liquid Chromatography Coupled to Tandem Mass Spectrometry (LC–MS/MS). Current Microbiology 2020, 77, 3057 -3064.

AMA Style

Hiroyuki Nakagawa, Ruiko Hashimoto, Yosuke Matsuo, Yuki Sago, Koji Yokoyama, Haruo Takahashi. Detection and Determination of Fumonisins B1, B2, and B3 Contaminating Japanese Domestic Wine by Liquid Chromatography Coupled to Tandem Mass Spectrometry (LC–MS/MS). Current Microbiology. 2020; 77 (10):3057-3064.

Chicago/Turabian Style

Hiroyuki Nakagawa; Ruiko Hashimoto; Yosuke Matsuo; Yuki Sago; Koji Yokoyama; Haruo Takahashi. 2020. "Detection and Determination of Fumonisins B1, B2, and B3 Contaminating Japanese Domestic Wine by Liquid Chromatography Coupled to Tandem Mass Spectrometry (LC–MS/MS)." Current Microbiology 77, no. 10: 3057-3064.

Journal article
Published: 03 April 2019 in Toxins
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Fusarium fujikuroi, a member of the Fusarium fujikuroi species complex, stands out as a rice bakanae disease pathogen with a high production of gibberellic acid. Not all, but some F. fujikuroi strains are known to produce a carcinogenic mycotoxin fumonisin. Fumonisin biosynthesis is dependent on the FUM cluster composed of 16 FUM genes. The FUM cluster was detected not only from a fumonisin producing strain, but also from a fumonisin nonproducing strain that does not produce a detectable level of fumonisin. Genetic mapping indicated the causative mutation(s) of fumonisin nonproduction is present in the FUM cluster of the fumonisin nonproducing strain. Comparative analyses of FUM genes between the fumonisin producing and the nonproducing strains and gene complementation indicated that causative mutation of fumonisin nonproduction is not a single occurrence and the mutations are distributed in FUM21 and FUM7. Our research revealed a natural variation in the FUM cluster involving fumonisin production difference in F. fujikuroi.

ACS Style

Sharmin Sultana; Miha Kitajima; Hironori Kobayashi; Hiroyuki Nakagawa; Masafumi Shimizu; Koji Kageyama; Haruhisa Suga. A Natural Variation of Fumonisin Gene Cluster Associated with Fumonisin Production Difference in Fusarium fujikuroi. Toxins 2019, 11, 200 .

AMA Style

Sharmin Sultana, Miha Kitajima, Hironori Kobayashi, Hiroyuki Nakagawa, Masafumi Shimizu, Koji Kageyama, Haruhisa Suga. A Natural Variation of Fumonisin Gene Cluster Associated with Fumonisin Production Difference in Fusarium fujikuroi. Toxins. 2019; 11 (4):200.

Chicago/Turabian Style

Sharmin Sultana; Miha Kitajima; Hironori Kobayashi; Hiroyuki Nakagawa; Masafumi Shimizu; Koji Kageyama; Haruhisa Suga. 2019. "A Natural Variation of Fumonisin Gene Cluster Associated with Fumonisin Production Difference in Fusarium fujikuroi." Toxins 11, no. 4: 200.

Journal article
Published: 29 July 2017 in Toxins
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Fusarium head blight (FHB) causes significant grain loss and contamination of grains with harmful mycotoxins, especially deoxynivalenol (DON). Fusarium resistance and DON accumulation have been extensively investigated in various cultivars; however, the level of DON-3-O-glucoside (D3G) has not been as carefully studied. In this study, we measured accumulated DON and D3G levels in CIMMYT wheat elite germplasm using an analytical method validated in-house. Co-occurring nivalenol (NIV) and ergostrerol (ERG) were also analyzed. LC-MS/MS and LC-UV analyses were applied to the 50 CIMMYT elite wheat lines. D3G showed rather high correlation with DON (r = 0.82), while FHB symptoms showed slight correlation with DON and D3G (r = 0.36 and 0.32, respectively). D3G/DON ratio varied widely from 8.1 to 37.7%, and the ratio was not related with FHB resistance in this dataset.

ACS Style

Hiroyuki Nakagawa; Xinyao He; Yosuke Matsuo; Pawan K. Singh; Masayo Kushiro. Analysis of the Masked Metabolite of Deoxynivalenol and Fusarium Resistance in CIMMYT Wheat Germplasm. Toxins 2017, 9, 238 .

AMA Style

Hiroyuki Nakagawa, Xinyao He, Yosuke Matsuo, Pawan K. Singh, Masayo Kushiro. Analysis of the Masked Metabolite of Deoxynivalenol and Fusarium Resistance in CIMMYT Wheat Germplasm. Toxins. 2017; 9 (8):238.

Chicago/Turabian Style

Hiroyuki Nakagawa; Xinyao He; Yosuke Matsuo; Pawan K. Singh; Masayo Kushiro. 2017. "Analysis of the Masked Metabolite of Deoxynivalenol and Fusarium Resistance in CIMMYT Wheat Germplasm." Toxins 9, no. 8: 238.

Journal article
Published: 16 September 2015 in Toxins
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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.

ACS Style

Yosuke Matsuo; Kentaro Takahara; Yuki Sago; Masayo Kushiro; Hitoshi Nagashima; Hiroyuki Nakagawa. Detection of N-(1-deoxy-d-fructos-1-yl) Fumonisins B2 and B3 in Corn by High-Resolution LC-Orbitrap MS. Toxins 2015, 7, 3700 -3714.

AMA Style

Yosuke Matsuo, Kentaro Takahara, Yuki Sago, Masayo Kushiro, Hitoshi Nagashima, Hiroyuki Nakagawa. Detection of N-(1-deoxy-d-fructos-1-yl) Fumonisins B2 and B3 in Corn by High-Resolution LC-Orbitrap MS. Toxins. 2015; 7 (9):3700-3714.

Chicago/Turabian Style

Yosuke Matsuo; Kentaro Takahara; Yuki Sago; Masayo Kushiro; Hitoshi Nagashima; Hiroyuki Nakagawa. 2015. "Detection of N-(1-deoxy-d-fructos-1-yl) Fumonisins B2 and B3 in Corn by High-Resolution LC-Orbitrap MS." Toxins 7, no. 9: 3700-3714.

Journal article
Published: 16 February 2015 in Toxins
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Fusarium graminearum is responsible for Fusarium head blight (FHB), which is a destructive disease of wheat that makes its quality unsuitable for end use. To understand the temporal molecular response against this pathogen, microarray gene expression analysis was carried out at two time points on three wheat genotypes, the spikes of which were infected by Fusarium graminearum. The greatest number of genes was upregulated in Nobeokabouzu-komugi followed by Sumai 3, whereas the minimum expression in Gamenya was at three days after inoculation (dai). In Nobeokabouzu-komugi, high expression of detoxification genes, such as multidrug-resistant protein, multidrug resistance-associated protein, UDP-glycosyltransferase and ABC transporters, in addition to systemic defense-related genes, were identified at the early stage of infection. This early response of the highly-resistant genotype implies a different resistance response from the other resistant genotype, Sumai 3, primarily containing local defense-related genes, such as cell wall defense genes. In Gamenya, the expression of all three functional groups was minimal. The differences in these molecular responses with respect to the time points confirmed the variation in the genotypes. For the first time, we report the nature of gene expression in the FHB-highly resistant cv. Nobeokabouzu-komugi during the disease establishment stage and the possible underlying molecular response.

ACS Style

Ayumi Kosaka; Alagu Manickavelu; Daniela Kajihara; Hiroyuki Nakagawa; Tomohiro Ban. Altered Gene Expression Profiles of Wheat Genotypes against Fusarium Head Blight. Toxins 2015, 7, 604 -620.

AMA Style

Ayumi Kosaka, Alagu Manickavelu, Daniela Kajihara, Hiroyuki Nakagawa, Tomohiro Ban. Altered Gene Expression Profiles of Wheat Genotypes against Fusarium Head Blight. Toxins. 2015; 7 (2):604-620.

Chicago/Turabian Style

Ayumi Kosaka; Alagu Manickavelu; Daniela Kajihara; Hiroyuki Nakagawa; Tomohiro Ban. 2015. "Altered Gene Expression Profiles of Wheat Genotypes against Fusarium Head Blight." Toxins 7, no. 2: 604-620.

Articles
Published: 30 May 2013 in Food Additives & Contaminants: Part A
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Masked mycotoxins (mycotoxin glucosides) derived from type A trichothecenes were detected in commercially available corn powder reference material. These new glucosides were identified as neosolaniol-glucoside (NESGlc) and diacetoxyscirpenol-glucoside (DASGlc) on the basis of accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography–Orbitrap mass spectrometric (LC-Orbitrap MS) analysis. Although the absolute structure was not clarified, 3-OH glucosylation appeared to be the most probable when considering the structures of neosolaniol and diacetoxyscirpenol and the fragmentation profiles of these masked mycotoxins. Concomitant detection of deoxynivalenol-3-glucoside, the most well-known masked mycotoxin derived from the type B trichothecene, deoxynivalenol, in the identical material further supports this probability.

ACS Style

H. Nakagawa; S. Sakamoto; Y. Sago; M. Kushiro; H. Nagashima. Detection of masked mycotoxins derived from type A trichothecenes in corn by high-resolution LC-Orbitrap mass spectrometer. Food Additives & Contaminants: Part A 2013, 30, 1407 -1414.

AMA Style

H. Nakagawa, S. Sakamoto, Y. Sago, M. Kushiro, H. Nagashima. Detection of masked mycotoxins derived from type A trichothecenes in corn by high-resolution LC-Orbitrap mass spectrometer. Food Additives & Contaminants: Part A. 2013; 30 (8):1407-1414.

Chicago/Turabian Style

H. Nakagawa; S. Sakamoto; Y. Sago; M. Kushiro; H. Nagashima. 2013. "Detection of masked mycotoxins derived from type A trichothecenes in corn by high-resolution LC-Orbitrap mass spectrometer." Food Additives & Contaminants: Part A 30, no. 8: 1407-1414.

Journal article
Published: 22 March 2013 in Toxins
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The existence of di-glucosylated derivative of T-2 toxin in plant (corn powder) was confirmed for the first time in addition to that of HT-2 toxin. These masked mycotoxins (mycotoxin glucosides) were identified as T-2 toxin-di-glucoside (T2GlcGlc) and HT-2 toxin-di-glucoside (HT2GlcGlc) based on accurate mass measurements of characteristic ions and fragmentation patterns using high-resolution liquid chromatography-Orbitrap mass spectrometric (LC-Orbitrap MS) analysis. Although the absolute structure of T2GlcGlc was not clarified, two glucose molecules were suggested to be conjugated at 3-OH position in tandem when considering the structure of T-2 toxin. On the other hand, the specification of the structure seems to be more complicated in the case of HT2GlcGlc, since HT-2 toxin has two possible positions (at 3-OH and 4-OH) to be glusocylated. In addition, 15-monoacetoxyscirpenol-glucoside (MASGlc) was also detected in the identical sample.

ACS Style

Hiroyuki Nakagawa; Shigeru Sakamoto; Yuki Sago; Hitoshi Nagashima. Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry. Toxins 2013, 5, 590 -604.

AMA Style

Hiroyuki Nakagawa, Shigeru Sakamoto, Yuki Sago, Hitoshi Nagashima. Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry. Toxins. 2013; 5 (3):590-604.

Chicago/Turabian Style

Hiroyuki Nakagawa; Shigeru Sakamoto; Yuki Sago; Hitoshi Nagashima. 2013. "Detection of Type A Trichothecene Di-Glucosides Produced in Corn by High-Resolution Liquid Chromatography-Orbitrap Mass Spectrometry." Toxins 5, no. 3: 590-604.

Journal article
Published: 17 August 2012 in International Journal of Molecular Sciences
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This study examined the effects of rice bran oil (RBO) on mouse intestinal microbiota and urinary isoflavonoids. Dietary RBO affects intestinal cholesterol absorption. Intestinal microbiota seem to play an important role in isoflavone metabolism. We hypothesized that dietary RBO changes the metabolism of isoflavonoids and intestinal microbiota in mice. Male mice were randomly divided into two groups: those fed a 0.05% daidzein with 10% RBO diet (RO group) and those fed a 0.05% daidzein with 10% lard control diet (LO group) for 30 days. Urinary amounts of daidzein and dihydrodaidzein were significantly lower in the RO group than in the LO group. The ratio of equol/daidzein was significantly higher in the RO group (p Lactobacillales were significantly higher in the RO group (p r = 0.591) was observed between the occupation ratios of Lactobacillales and fecal bile acid content of two dietary groups. This study suggests that dietary rice bran oil has the potential to affect the metabolism of daidzein by altering the metabolic activity of intestinal microbiota.

ACS Style

Motoi Tamura; Sachiko Hori; Chigusa Hoshi; Hiroyuki Nakagawa. Effects of Rice Bran Oil on the Intestinal Microbiota and Metabolism of Isoflavones in Adult Mice. International Journal of Molecular Sciences 2012, 13, 10336 -10349.

AMA Style

Motoi Tamura, Sachiko Hori, Chigusa Hoshi, Hiroyuki Nakagawa. Effects of Rice Bran Oil on the Intestinal Microbiota and Metabolism of Isoflavones in Adult Mice. International Journal of Molecular Sciences. 2012; 13 (8):10336-10349.

Chicago/Turabian Style

Motoi Tamura; Sachiko Hori; Chigusa Hoshi; Hiroyuki Nakagawa. 2012. "Effects of Rice Bran Oil on the Intestinal Microbiota and Metabolism of Isoflavones in Adult Mice." International Journal of Molecular Sciences 13, no. 8: 10336-10349.

Original articles
Published: 15 August 2011 in Food Additives & Contaminants: Part A
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A new Fusarium mycotoxin glucoside, fusarenon X-glucoside (FUXGlc), is reported for the first time in wheat grain that was artificially infected with Fusarium fungi. This new glucoside was identified using LC Orbitrap high-resolution mass spectrometry (LC–Orbitrap MS) analysis on the basis of accurate mass measurement of characteristic ions and MS/MS fragmentation patterns. Although the absolute structure of FUXGlc was not clarified by LC–MS, 3-OH glucosylation seems to be the most probable structure based on the fragment profile and considering that deoxynivalenol-3-glucoside (DON3Glc) was reported as the predominant glucosylated derivative of the structurally similar mycotoxin, deoxynivalenol (DON). Another mycotoxin glucoside, nivalenol-glucoside (NIVGlc) was also found in the same grain sample. According to the semi-quantification by LC–Orbitrap MS, more than 15% of FUX and NIV were estimated to be converted into respective glucosides. The existence of these masked mycotoxins should be taken into account in risk assessment, since they could be transformed back to the corresponding mycotoxins under certain conditions; for example, through various food processing operations or in the digestive tract of mammals after ingestion.

ACS Style

H. Nakagawa; K. Ohmichi; S. Sakamoto; Y. Sago; M. Kushiro; H. Nagashima; M. Yoshida; T. Nakajima. Detection of a newFusariummasked mycotoxin in wheat grain by high-resolution LC–Orbitrap™ MS. Food Additives & Contaminants: Part A 2011, 28, 1447 -1456.

AMA Style

H. Nakagawa, K. Ohmichi, S. Sakamoto, Y. Sago, M. Kushiro, H. Nagashima, M. Yoshida, T. Nakajima. Detection of a newFusariummasked mycotoxin in wheat grain by high-resolution LC–Orbitrap™ MS. Food Additives & Contaminants: Part A. 2011; 28 (10):1447-1456.

Chicago/Turabian Style

H. Nakagawa; K. Ohmichi; S. Sakamoto; Y. Sago; M. Kushiro; H. Nagashima; M. Yoshida; T. Nakajima. 2011. "Detection of a newFusariummasked mycotoxin in wheat grain by high-resolution LC–Orbitrap™ MS." Food Additives & Contaminants: Part A 28, no. 10: 1447-1456.