A Sphingolipid Having a Novel Type of Ceramide and Lacto-N-Fucopentaose III

TLDR

Sphingoglycolipids are known to be present in cancer cells, and a new variant was isolated from human adenocarcinomas. An antibody raised in rabbit specifically precipitated the glycolipid, reacting only with it and not with Lewis a or Lewis b, and its binding was inhibited by lacto‑N‑fucopentaose III. The glycolipid contains a novel ceramide rich in 4‑hydroxysphinganine and α‑hydroxy fatty acids, and its carbohydrate moiety matches lacto‑N‑fucopentaose III.

Abstract

Abstract A new sphingoglycolipid was isolated from human adenocarcinomas. The glycolipid had a novel ceramide which contained predominantly 4-hydroxysphinganine (phytosphingosine) and a high content of α-hydroxy fatty acids. The structure of the carbohydrate moiety was identified as O-β-galactosyl-(1 → 4)-[O-α-l-fucosyl-(1 → 3)]-O-β-(N-acetyl)glucosaminosyl-(1 → 3)-O-β-galactosyl-(1 → 4)-glucose, which was identical with that of lacto-N-fucopentaose III (Kobata, A., and Ginsburg, V., J. Biol. Chem., 244, 5496 (1969)). The precipitating antibody against this glycolipid was produced in rabbit, the antiserum was allowed to react specifically with this glycolipid but not with Lewis a or Lewis b glycolipid, and the precipitin reaction was inhibited by lacto-N-fucopentaose III.