Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus

Saki Itonori, Saho Yamawaki, Kazuhiro Aoki, Kenji Yamamoto, Noriyasu Hada, Tadahiro Takeda, John T. Dulaney, Mutsumi Sugita

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Abstract

Edible fungi, mushrooms, are a popular food in Japan and over 15 cultured mushroom species are available at the food markets. Recently, constituents or ingredients of edible mushrooms have drawn attention because possibilities have been seen for their medical usage. Mycoglycolipids (basidiolipids) of higher mushrooms have been characterized as glycosylinositolphosphoceramides, having a common core structure of Manα1-2Ins1-[PO4]-Cer and extensions of Man, Gal, and/or Fuc sugar moieties. Seven mycoglycolipids were purified from the edible mushroom Hypsizygus marmoreus by successive column chromatography on ion exchange Sephadex (DEAE-Sephadex) and silicic acid (Iatrobeads). Their structures were characterized to be Ins1-[PO4]-Cer (AGL0), Manα1-2Ins1-[PO4]-Cer (AGL1), Galβ1-6Manα1-2Ins1-[PO4]-Cer (AGL2), Fucα1- 2Galβ1-6Manα1-2Ins1-[PO4]-Cer (AGL3), Galα1-3(Fucα1-2)Galβ1-6Manα1-2Ins1- [PO4]-Cer (AGL4), Galα1-2Galα1- 3(Fucα1-2)Galβ1-6Manα1-2Ins1-[PO4]-Cer (AGL5), and Galα1-2Galα1- 2Galα1-3(Fucα1-2 Galβ1-6Manα1-2Ins1-[PO4]-Cer (AGL6) by sugar compositional analysis, methylation analysis, periodate oxidation, partial acid hydrolysis, enzymatic hydrolysis, immunochemical analysis, gas-liquid chromatography (GC), gas chromatography-mass spectrometry (GC-MS), matrixassisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOFMS), and 1H-nuclear magnetic resonance spectroscopy (NMR). Ceramide constituents of their mycoglycolipids were composed of phytosphingosine as the sole sphingoid, and mainly 2-hydroxy C22:0 and C24:0 acids as the fatty acids. By immunochemical detection, the terminal structure of AGL4, Galα1-3 (Fucα1-2)Galβ-, was shown to have blood group type B activity. Galα1-2 and its repeating sequence in AGL5 and AGL6 are novel structures on the nonreducing sugar end in mycoglycolipids. These two mycoglycolipids in H. marmoreus distinguish it from other basidiomycetes.

Original languageEnglish
Pages (from-to)540-548
Number of pages9
JournalGlycobiology
Volume18
Issue number7
DOIs
Publication statusPublished - 2008 Jul 1

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Keywords

  • Blood group
  • Glycosphingolipid
  • Hypsizygus marmoreus
  • Mushroom
  • Mycoglycolipid

ASJC Scopus subject areas

  • Biochemistry

Cite this

Itonori, S., Yamawaki, S., Aoki, K., Yamamoto, K., Hada, N., Takeda, T., Dulaney, J. T., & Sugita, M. (2008). Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus. Glycobiology, 18(7), 540-548. https://doi.org/10.1093/glycob/cwn036