Dolichol biosynthesis: The occurrence of epoxy dolichol in skipjack tuna liver |
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| Authors: | Terumi Ishiguro Yuiko Morita-Fujimura Yoshihiro Shidoji Hiroshi Sagami |
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| Affiliation: | 1. Institute of Multidisciplinary Research for Advanced Materials (IMRAM), Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan;2. Institute of Development, Aging and Cancer (IDAC), Tohoku University, 4-1 Seiryo-machi, Aoba-ku, Sendai 980-8575, Japan;3. Graduate School of Human Health Sciences, University of Nagasaki, 1-1-1 Academy Hills, Nagayo, Nagasaki 851-2195, Japan |
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| 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. |
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| Keywords: | Dolichol Isoprenoid Epoxide Midbrain Betulaprenol Glycoprotein |
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