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 death-inducing 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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Research Article|
March 01 2004
Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells
Kazuhiro AOKI;
Kazuhiro AOKI
1
*Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan
1To whom correspondence should be addressed (e-mail kaoki@lif.kyoto-u.ac.jp).
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Ryosuke UCHIYAMA;
Ryosuke UCHIYAMA
*Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan
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Saki ITONORI;
Saki ITONORI
†Faculty of Liberal Arts and Education, Shiga University, 2-5-1, Hiratsu, Otsu, Shiga 520-0862, Japan
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Mutsumi SUGITA;
Mutsumi SUGITA
†Faculty of Liberal Arts and Education, Shiga University, 2-5-1, Hiratsu, Otsu, Shiga 520-0862, Japan
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Fang-Sik CHE;
Fang-Sik CHE
‡Graduate School of Biological Sciences, Nara Institute of Science and Technology, 8916-5, Takayama, Ikoma, Nara 630-0101, Japan
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Akira ISOGAI;
Akira ISOGAI
‡Graduate School of Biological Sciences, Nara Institute of Science and Technology, 8916-5, Takayama, Ikoma, Nara 630-0101, Japan
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Noriyasu HADA;
Noriyasu HADA
§Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan
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Junko HADA;
Junko HADA
§Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan
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Tadahiro TAKEDA;
Tadahiro TAKEDA
§Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan
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Hidehiko KUMAGAI;
Hidehiko KUMAGAI
*Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan
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Kenji YAMAMOTO
Kenji YAMAMOTO
*Graduate School of Biostudies, Kyoto University, Oiwake-cho, Kitashirakawa, Sakyo-ku, Kyoto 606-8502, Japan
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Publisher: Portland Press Ltd
Received:
August 27 2003
Revision Received:
October 17 2003
Accepted:
October 29 2003
Accepted Manuscript online:
October 29 2003
Online ISSN: 1470-8728
Print ISSN: 0264-6021
The Biochemical Society, London ©2004
2004
Biochem J (2004) 378 (2): 461–472.
Article history
Received:
August 27 2003
Revision Received:
October 17 2003
Accepted:
October 29 2003
Accepted Manuscript online:
October 29 2003
Citation
Kazuhiro AOKI, Ryosuke UCHIYAMA, Saki ITONORI, Mutsumi SUGITA, Fang-Sik CHE, Akira ISOGAI, Noriyasu HADA, Junko HADA, Tadahiro TAKEDA, Hidehiko KUMAGAI, Kenji YAMAMOTO; Structural elucidation of novel phosphocholine-containing glycosylinositol-phosphoceramides in filamentous fungi and their induction of cell death of cultured rice cells. Biochem J 1 March 2004; 378 (2): 461–472. doi: https://doi.org/10.1042/bj20031307
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