Phytochemical Studies on Paeoniae Radix (4) - Cerebrosides and Other Constituents
2008
Kim, Y.J. (Seoul National University, Seoul, Republic of Korea) | Yean, M.H. (Seoul National University, Seoul, Republic of Korea) | Lee, E.J. (Seoul National University, Seoul, Republic of Korea) | Kim, J.S. (Seoul National University, Seoul, Republic of Korea) | Lee, J.H. (Dongguk University, Gyeongju, Republic of Korea) | Kang, S.S. (Seoul National University, Seoul, Republic of Korea), E-mail: [email protected]
A mixture of sixteen cerebrosides, which comprised four cerebroside molecular species (PL-1 ~ PL-4) was separated from the roots of Paeonia lactiflora. The structures of cerebrosides were characterized as 1-O-β-D-glucopyranosides of phytosphingosines, which comprised a common long-chain base, (2S,3S,4R,8E/Z)-2-amino-8-octadecene-1,3,4-triol with eight fatty acids or 2-hydroxy fatty acids of varying chain lengths (C∧16, C∧18, C∧20-26) linked to the amino group. Aralia cerebroside and its 8Z isomer (PL-1), 1-O-β-D-glucopyranosyl-(2S,3S, 4R,8E/Z)-2-[(2'R)-2'-hydroxytetracosanoylamino]-8-octadecene-1,3,4-triol (PL-2), 1-O-β-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxydocosanoylamino]-8-octadecene-1,3,4-triol (PL-3), and 1-O-β-D-glucopyranosyl-(2S,3S,4R, 8E/Z)-2-[(2'R)-2'-hydroxytricosanoylamino]-8-octadecene-1,3,4-triol (PL-4) were identified as major components of these cerebroside molecular species. All the major cerebrosides were shown to be a mixture of geometrical isomers (8E and 8Z) of phytosphingosine-type glucocerebrosides possessing 2R-hydroxy fatty acids. In addition, three β-sitosterol derivatives and adenosine were also separated. The structures of these isolates have been determined on the basis of chemical and spectroscopic evidence.
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