Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells

Kazuhiro Aoki, Ryosuke Uchiyama, Saki Itonori, Mutsumi Sugita, Fang Sik Che, Akira Isogai, Noriyasu Hada, Junko Hada, Tadahiro Takeda, Hidehiko Kumagai, Kenji Yamamoto

研究成果: Article

27 引用 (Scopus)

抄録

Novel ZGLs (zwitterionic glycosphingolipids) have been found in and extracted from the mycelia of filamentous fungi (Acremonium sp.) isolated from soil. Five ZGLs (ZGL1-ZGL5) were structurally elucidated by sugar compositional analysis, methylation analysis, periodate oxidation, matrix-assisted laser-desorption ionization-time-of-flight MS, 1H-NMR spectroscopy and fast-atom bombardment MS. Their chemical structures were as follows: GlcN(α1-2)Ins1-P-1Cer (ZGL1), Man(α1-6) GlcN(α1-2)Ins1-P-1Cer (ZGL2), Man(α1-6)Man(α1-6)GlcN (α1-2)Ins1-P-1Cer (ZGL3), PC → 6Man(α1-6)GlcN(α1-2)Ins1-P-1Cer (ZGL4), and PC → 6Man(α1-6)Man(α1-6)GlcN(α1-2) Ins1-P-1Cer (ZGL5) (where Cer is ceramide and PC is phosphocholine). In addition, one acidic glycosphingolipid, which was the precursor of ZGLs, was also characterized as inositol-phosphoceramide. The core structure of the ZGLs, GlcN(α1-2)Ins1- P, is rather different from those found in other fungi, such as Man(α1-2)Ins1-P and Man(α1-6)Ins1-P. Interestingly, the terminal mannose residue of ZGL4 and ZGL5 was modified further with a PC group. The presence of PC-containing glycosylinositol-phosphoceramides has not been reported previously in any organism. The ceramide constituents of both ZGLs and acidic glycosphingolipid were essentially the same, and consisted of a 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid base and 2-hydroxytetracosanoic acid (>90%) as the major fatty acid. ZGLs were found to cause cell death in suspensions of cultured rice cells. The cell deathinducing activity of ZGLs is probably due to the characteristic glycan moiety of Man(α1-6)GlcN, and PC-containing ZGLs had high activity. This study is the first to demonstrate that fungal glycosylinositol-phosphoceramides induce cell death in cultured rice cells.

元の言語English
ページ(範囲)461-472
ページ数12
ジャーナルBiochemical Journal
378
発行部数2
DOI
出版物ステータスPublished - 2004 3 1

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Glycosphingolipids
Phosphorylcholine
Cell death
Fungi
Cultured Cells
Cell Death
Acidic Glycosphingolipids
phytosphingosine
Ceramides
Acremonium
Methylation
Inositol
Mannose
Oryza
Mycelium
Sugars
Nuclear magnetic resonance spectroscopy
Ionization
Polysaccharides
Desorption

ASJC Scopus subject areas

  • Biochemistry

これを引用

Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells. / Aoki, Kazuhiro; Uchiyama, Ryosuke; Itonori, Saki; Sugita, Mutsumi; Che, Fang Sik; Isogai, Akira; Hada, Noriyasu; Hada, Junko; Takeda, Tadahiro; Kumagai, Hidehiko; Yamamoto, Kenji.

:: Biochemical Journal, 巻 378, 番号 2, 01.03.2004, p. 461-472.

研究成果: Article

Aoki, K, Uchiyama, R, Itonori, S, Sugita, M, Che, FS, Isogai, A, Hada, N, Hada, J, Takeda, T, Kumagai, H & Yamamoto, K 2004, 'Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells', Biochemical Journal, 巻. 378, 番号 2, pp. 461-472. https://doi.org/10.1042/BJ20031307
Aoki, Kazuhiro ; Uchiyama, Ryosuke ; Itonori, Saki ; Sugita, Mutsumi ; Che, Fang Sik ; Isogai, Akira ; Hada, Noriyasu ; Hada, Junko ; Takeda, Tadahiro ; Kumagai, Hidehiko ; Yamamoto, Kenji. / Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells. :: Biochemical Journal. 2004 ; 巻 378, 番号 2. pp. 461-472.
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abstract = "Novel ZGLs (zwitterionic glycosphingolipids) have been found in and extracted from the mycelia of filamentous fungi (Acremonium sp.) isolated from soil. Five ZGLs (ZGL1-ZGL5) were structurally elucidated by sugar compositional analysis, methylation analysis, periodate oxidation, matrix-assisted laser-desorption ionization-time-of-flight MS, 1H-NMR spectroscopy and fast-atom bombardment MS. Their chemical structures were as follows: GlcN(α1-2)Ins1-P-1Cer (ZGL1), Man(α1-6) GlcN(α1-2)Ins1-P-1Cer (ZGL2), Man(α1-6)Man(α1-6)GlcN (α1-2)Ins1-P-1Cer (ZGL3), PC → 6Man(α1-6)GlcN(α1-2)Ins1-P-1Cer (ZGL4), and PC → 6Man(α1-6)Man(α1-6)GlcN(α1-2) Ins1-P-1Cer (ZGL5) (where Cer is ceramide and PC is phosphocholine). In addition, one acidic glycosphingolipid, which was the precursor of ZGLs, was also characterized as inositol-phosphoceramide. The core structure of the ZGLs, GlcN(α1-2)Ins1- P, is rather different from those found in other fungi, such as Man(α1-2)Ins1-P and Man(α1-6)Ins1-P. Interestingly, the terminal mannose residue of ZGL4 and ZGL5 was modified further with a PC group. The presence of PC-containing glycosylinositol-phosphoceramides has not been reported previously in any organism. The ceramide constituents of both ZGLs and acidic glycosphingolipid were essentially the same, and consisted of a 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid base and 2-hydroxytetracosanoic acid (>90{\%}) as the major fatty acid. ZGLs were found to cause cell death in suspensions of cultured rice cells. The cell deathinducing activity of ZGLs is probably due to the characteristic glycan moiety of Man(α1-6)GlcN, and PC-containing ZGLs had high activity. This study is the first to demonstrate that fungal glycosylinositol-phosphoceramides induce cell death in cultured rice cells.",
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T1 - Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells

AU - Aoki, Kazuhiro

AU - Uchiyama, Ryosuke

AU - Itonori, Saki

AU - Sugita, Mutsumi

AU - Che, Fang Sik

AU - Isogai, Akira

AU - Hada, Noriyasu

AU - Hada, Junko

AU - Takeda, Tadahiro

AU - Kumagai, Hidehiko

AU - Yamamoto, Kenji

PY - 2004/3/1

Y1 - 2004/3/1

N2 - Novel ZGLs (zwitterionic glycosphingolipids) have been found in and extracted from the mycelia of filamentous fungi (Acremonium sp.) isolated from soil. Five ZGLs (ZGL1-ZGL5) were structurally elucidated by sugar compositional analysis, methylation analysis, periodate oxidation, matrix-assisted laser-desorption ionization-time-of-flight MS, 1H-NMR spectroscopy and fast-atom bombardment MS. Their chemical structures were as follows: GlcN(α1-2)Ins1-P-1Cer (ZGL1), Man(α1-6) GlcN(α1-2)Ins1-P-1Cer (ZGL2), Man(α1-6)Man(α1-6)GlcN (α1-2)Ins1-P-1Cer (ZGL3), PC → 6Man(α1-6)GlcN(α1-2)Ins1-P-1Cer (ZGL4), and PC → 6Man(α1-6)Man(α1-6)GlcN(α1-2) Ins1-P-1Cer (ZGL5) (where Cer is ceramide and PC is phosphocholine). In addition, one acidic glycosphingolipid, which was the precursor of ZGLs, was also characterized as inositol-phosphoceramide. The core structure of the ZGLs, GlcN(α1-2)Ins1- P, is rather different from those found in other fungi, such as Man(α1-2)Ins1-P and Man(α1-6)Ins1-P. Interestingly, the terminal mannose residue of ZGL4 and ZGL5 was modified further with a PC group. The presence of PC-containing glycosylinositol-phosphoceramides has not been reported previously in any organism. The ceramide constituents of both ZGLs and acidic glycosphingolipid were essentially the same, and consisted of a 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid base and 2-hydroxytetracosanoic acid (>90%) as the major fatty acid. ZGLs were found to cause cell death in suspensions of cultured rice cells. The cell deathinducing activity of ZGLs is probably due to the characteristic glycan moiety of Man(α1-6)GlcN, and PC-containing ZGLs had high activity. This study is the first to demonstrate that fungal glycosylinositol-phosphoceramides induce cell death in cultured rice cells.

AB - Novel ZGLs (zwitterionic glycosphingolipids) have been found in and extracted from the mycelia of filamentous fungi (Acremonium sp.) isolated from soil. Five ZGLs (ZGL1-ZGL5) were structurally elucidated by sugar compositional analysis, methylation analysis, periodate oxidation, matrix-assisted laser-desorption ionization-time-of-flight MS, 1H-NMR spectroscopy and fast-atom bombardment MS. Their chemical structures were as follows: GlcN(α1-2)Ins1-P-1Cer (ZGL1), Man(α1-6) GlcN(α1-2)Ins1-P-1Cer (ZGL2), Man(α1-6)Man(α1-6)GlcN (α1-2)Ins1-P-1Cer (ZGL3), PC → 6Man(α1-6)GlcN(α1-2)Ins1-P-1Cer (ZGL4), and PC → 6Man(α1-6)Man(α1-6)GlcN(α1-2) Ins1-P-1Cer (ZGL5) (where Cer is ceramide and PC is phosphocholine). In addition, one acidic glycosphingolipid, which was the precursor of ZGLs, was also characterized as inositol-phosphoceramide. The core structure of the ZGLs, GlcN(α1-2)Ins1- P, is rather different from those found in other fungi, such as Man(α1-2)Ins1-P and Man(α1-6)Ins1-P. Interestingly, the terminal mannose residue of ZGL4 and ZGL5 was modified further with a PC group. The presence of PC-containing glycosylinositol-phosphoceramides has not been reported previously in any organism. The ceramide constituents of both ZGLs and acidic glycosphingolipid were essentially the same, and consisted of a 4-hydroxyoctadecasphinganine (phytosphingosine) as the sole sphingoid base and 2-hydroxytetracosanoic acid (>90%) as the major fatty acid. ZGLs were found to cause cell death in suspensions of cultured rice cells. The cell deathinducing activity of ZGLs is probably due to the characteristic glycan moiety of Man(α1-6)GlcN, and PC-containing ZGLs had high activity. This study is the first to demonstrate that fungal glycosylinositol-phosphoceramides induce cell death in cultured rice cells.

KW - Cell death

KW - Elicitor

KW - Phosphocholine

KW - Plant-pathogen interaction

KW - Rice cell

KW - Zwitterionic glycosphingolipid

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