A novel oligosaccharide, xylosyl beta 1-4xylosyl beta 1-(4-methylumbelliferone), synthesized by cultured human skin fibroblasts in the presence of 4-methylumbelliferyl-beta-D-xyloside.
4-Methylumbelliferyl-beta-D-xyloside (Xyl-MU) was added to the medium of cultured human skin fibroblasts. After incubation, the culture medium was pooled, concentrated with a lyophilizer, and dialyzed against distilled water. Then the Xyl-MU derivatives in the diffusate were purified by gel-filtration and HPLC. A novel Xyl-MU derivative was obtained, in addition to the previously reported Xyl-MU derivatives, Xyl-MU-induced glycosaminoglycan (GAG-MU), SA-Gal-Xyl-MU, GlcA-Xyl-MU, Gal-Gal-Xyl-MU, and Gal-Xyl-MU. This Xyl-MU derivative was subjected to carbohydrate composition analysis, enzyme digestion, Smith degradation and ion-spray mass spectrometric analysis, and the results indicated that it was Xyl beta 1-4Xyl beta 1-MU. Although the quantity of Xyl beta 1-4Xyl beta 1-MU synthesized by human skin fibroblasts increased with incubation time, its production was independent of that of the GAG-MU. Xyl-Xyl-MU is different from the intermediates in the regular pathway of GAG-MU biosynthesis initiated by added Xyl-MU, posing an interesting question as to its significance in GAG biosynthesis.
Izumi
J
J
Department of Biochemistry, Hirosaki University School of Medicine.
Takagaki
K
K
Nakamura
T
T
Shibata
S
S
Kojima
K
K
Kato
I
I
Endo
M
M
D002240:Carbohydrate Sequence; D002478:Cells, Cultured; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D006801:Humans; D006923:Hymecromone / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012867:Skin / Q000187:drug effects* / Q000378:metabolism
C091993:xylosyl-1-4-xylosyl-1-(4-methylumbelliferone); D006923:Hymecromone; C014111:methylumbelliferyl-beta-D-xyloside