title: Dolichol biosynthesis: the occurrence of epoxy dolichol in skipjack tuna liver.
abstract: 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.
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Terumi
authors.initials: T
authors.lastname: Ishiguro
authors.affiliation: Institute of Development, Aging and Cancer (IDAC), Tohoku University, 4-1 Seiryo-machi, Aoba-ku, Sendai 980-8575, Japan.
authors.forename: Yuiko
authors.initials: Y
authors.lastname: Morita-Fujimura
authors.affiliation: Graduate School of Human Health Sciences, University of Nagasaki, 1-1-1 Academy Hills, Nagayo, Nagasaki 851-2195, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shidoji
authors.affiliation: Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan. Electronic address: yasagami@tagen.tohoku.ac.jp.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sagami
mesh_terms: D000818:Animals; D002855:Chromatography, Thin Layer; D004286:Dolichols / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism; D008099:Liver / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D053858:Metabolic Networks and Pathways; D017686:Oncorhynchus mykiss / Q000378:metabolism; D010473:Perciformes / Q000378:metabolism; D021541:Sea Bream / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D014413:Tuna / Q000378:metabolism*
chemical_list: D004286:Dolichols; D004852:Epoxy Compounds
keywords: Betulaprenol; Dolichol; Epoxide; Glycoprotein; Isoprenoid; Midbrain