TY - JOUR
T1 - Dolichol biosynthesis
T2 - The occurrence of epoxy dolichol in skipjack tuna liver
AU - Ishiguro, Terumi
AU - Morita-Fujimura, Yuiko
AU - Shidoji, Yoshihiro
AU - Sagami, Hiroshi
N1 - Publisher Copyright:
© 2014 Elsevier Inc. All rights reserved.
PY - 2014/10/17
Y1 - 2014/10/17
N2 - Polyisoprenoid alcohols from the livers of temperate sea fish (skipjack tuna, chub mackerel, red sea bream and rainbow trout) were analyzed by using 2D-TLC, electrospray ionization (ESI) mass spectrometry and NMR methods. Dolichols (Dols) were detected in all the fish livers, and they were composed of 19-22 isoprene units with Dol-20 as the predominant prenolog. In addition, Dol-like family compounds were found by using 2D-TLC on skipjack tuna samples. These compounds were found to have a larger molecular mass than the Dol family by 16 mass units. NMR analysis indicated that the Dol-like compounds were consistent with the terminal epoxide structure of Dols (the ω-oxirane derivatives of Dols). ESI analysis also revealed the occurrence of dehydro molecules in both Dols and epoxy Dols (Dol-like) fractions. The occurrence of epoxy Dols in fish is discussed in context with the biosynthesis of Dols, which is responsible for forming Dol phosphate, which lead to Dol-PP-oligosaccharide.
AB - Polyisoprenoid alcohols from the livers of temperate sea fish (skipjack tuna, chub mackerel, red sea bream and rainbow trout) were analyzed by using 2D-TLC, electrospray ionization (ESI) mass spectrometry and NMR methods. Dolichols (Dols) were detected in all the fish livers, and they were composed of 19-22 isoprene units with Dol-20 as the predominant prenolog. In addition, Dol-like family compounds were found by using 2D-TLC on skipjack tuna samples. These compounds were found to have a larger molecular mass than the Dol family by 16 mass units. NMR analysis indicated that the Dol-like compounds were consistent with the terminal epoxide structure of Dols (the ω-oxirane derivatives of Dols). ESI analysis also revealed the occurrence of dehydro molecules in both Dols and epoxy Dols (Dol-like) fractions. The occurrence of epoxy Dols in fish is discussed in context with the biosynthesis of Dols, which is responsible for forming Dol phosphate, which lead to Dol-PP-oligosaccharide.
KW - Betulaprenol
KW - Dolichol
KW - Epoxide
KW - Glycoprotein
KW - Isoprenoid
KW - Midbrain
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U2 - 10.1016/j.bbrc.2014.05.079
DO - 10.1016/j.bbrc.2014.05.079
M3 - Article
C2 - 24866245
AN - SCOPUS:84908413011
SN - 0006-291X
VL - 453
SP - 277
EP - 281
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 2
ER -