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Glycobiology Advance Access originally published online on May 1, 2008
Glycobiology 2008 18(7):540-548; doi:10.1093/glycob/cwn036
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© The Author 2008. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

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

Saki Itonori1,3, Saho Yamawaki3, Kazuhiro Aoki2,4, Kenji Yamamoto4, Noriyasu Hada5, Tadahiro Takeda5, John T. Dulaney6 and Mutsumi Sugita3

3 Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Hiratsu, Otsu, Shiga 520-0862, Japan
4 Department of Applied Molecular Biology, Division of Integrated Life Science, Graduate School of Biostudies, Kyoto University, Kitashirakawa Oiwake-cho, Sakyo-ku, Kyoto 606-8502, Japan
5 Kyoritsu College of Pharmacy, 1-5-30, Shibakoen, Minato-ku, Tokyo 105-8512, Japan
6 Department of Medicine, Division of Nephrology, The University of Tennessee, Court Avenue, Memphis, TN 38163, USA

1 To whom correspondence should be addressed: Tel: +81-77-537-7728; Fax: +81-77-537-7728; e-mail: itonori{at}sue.shiga-u.ac.jp

Received on February 1, 2008; revised on April 25, 2008; accepted on April 25, 2008

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 Man{alpha}1-2Ins1-[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), Man{alpha}1-2Ins1-[PO4]-Cer (AGL1), Galβ1-6Man{alpha}1-2Ins1-[PO4]-Cer (AGL2), Fuc{alpha}1- 2Galβ1-6Man{alpha}1-2Ins1-[PO4]-Cer (AGL3), Gal{alpha}1-3(Fuc{alpha}1-2)Galβ1-6Man{alpha}1-2Ins1-[PO4]-Cer (AGL4), Gal{alpha}1-2Gal{alpha}1-3(Fuc{alpha}1-2)Galβ1-6Man{alpha}1-2Ins1-[PO4]-Cer (AGL5), and Gal{alpha}1-2Gal{alpha}1-2Gal{alpha}1-3(Fuc{alpha}1-2)Galβ1-6Man{alpha}1-2Ins1-[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), matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF MS), 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, Gal{alpha}1-3(Fuc{alpha}1-2)Galβ-, was shown to have blood group type B activity. Gal{alpha}1-2 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.

Key words: blood group / glycosphingolipid / Hypsizygus marmoreus / mushroom / mycoglycolipid

2 Present address: Complex Carbohydrate Research Center, University of Georgia, Athens, GA 30602, USA.


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