Chem. Pharm. Bull., 53(7),788-791, July 2005

Regular Articles

Constituents of Holothuroidea, 15.¹⁾ Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

Koji YAMADA,^a Noriko WADA,^a Hiroyuki ONAKA,^a Rei MATSUBARA,^a Ryuichi ISOBE,^b Masanori INAGAKI,^a and Ryuichi HIGUCHI^*,a

^a Faculty of Pharmaceutical Sciences, Kyushu University; 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan: and ^b Department of Medical Electronics Engineering, Faculty of Engineering, Towa University; 1-1-1 Chikusigaoka, Minami-ku, Fukuoka 815-0036, Japan. * To whom correspondence should be addressed.

An ante-iso type regio-isomer on the long chain base moiety of a glucocerebroside, HLC-2-A, has been isolated from its parent glucocerebroside molecular species HLC-2 composed of iso and ante-iso isomers, from the less polar lipid fraction of a chloroform/methanol extract of the sea cucumber Holothuria leucospilota. Reverse-phase HPLC that included a recycling system was effective in separating the regio-isomer from its counterpart, revealing a very close resemblance in structure. Other typical glucocerebroside molecular species HLC-1 and HLC-3 were obtained together with HLC-2. The structures of these glucocerebrosides were determined on the basis of chemical and spectroscopic evidence.

Key words glycosphingolipid; glucocerebroside; sea cucumber; Holothuria leucospilota; recycling HPLC