title: Structural characterization of glycosylinositolphospholipids with a blood group type B sugar unit from the edible mushroom, Hypsizygus marmoreus.
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 Manalpha1-2Ins1-[PO(4)]-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-[PO(4)]-Cer (AGL0), Manalpha1-2Ins1-[PO(4)]-Cer (AGL1), Galbeta1-6Manalpha1-2Ins1-[PO(4)]-Cer (AGL2), Fucalpha1- 2Galbeta1-6Manalpha1-2Ins1-[PO(4)]-Cer (AGL3), Galalpha1-3(Fucalpha1-2)Galbeta1-6Manalpha1-2Ins1-[PO(4)]-Cer (AGL4), Galalpha1-2Galalpha1-3(Fucalpha1-2)Galbeta1-6Manalpha1-2Ins1-[PO(4)]-Cer (AGL5), and Galalpha1-2Galalpha1-2Galalpha1-3(Fucalpha1-2)Galbeta1-6Manalpha1-2Ins1-[PO(4)]-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 (1)H-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, Galalpha1-3(Fucalpha1-2)Galbeta-, was shown to have blood group type B activity. Galalpha1-2 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.
authors.affiliation: Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Hiratsu, Otsu, Shiga 520-0862, Japan. itonori@sue.shiga-u.ac.jp
authors.forename: Saki
authors.initials: S
authors.lastname: Itonori
authors.forename: Saho
authors.initials: S
authors.lastname: Yamawaki
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Aoki
authors.forename: Kenji
authors.initials: K
authors.lastname: Yamamoto
authors.forename: Noriyasu
authors.initials: N
authors.lastname: Hada
authors.forename: Tadahiro
authors.initials: T
authors.lastname: Takeda
authors.forename: John T
authors.initials: JT
authors.lastname: Dulaney
authors.forename: Mutsumi
authors.initials: M
authors.lastname: Sugita
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D001789:Blood Group Antigens / Q000737:chemistry* / Q000276:immunology; D002241:Carbohydrates / Q000737:chemistry* / Q000276:immunology; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000737:chemistry; D006028:Glycosphingolipids / Q000032:analysis* / Q000737:chemistry / Q000276:immunology; D006801:Humans; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D001789:Blood Group Antigens; D002241:Carbohydrates; D005227:Fatty Acids; D006028:Glycosphingolipids; C025524:inositolphosphoceramides