Agelasphins, novel antitumor and immunostimulatory cerebrosides from the marine sponge Agelas mauritianus

✍ Scribed by Takenori Natori; Masahiro Morita; Kohji Akimoto; Yasuhiko Koezuka

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 1011 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86991-x

✦ Synopsis

New glycosphingolipids, named agelasphins (1-S). have been isolated by antitumor and immtmostimulatory bioassay-guided purification from an extract of a marine sponge, Agelas mouritianus. Strongly active agents in agelasphins had characteristic a-galactosylceramide structures, the isolation of which from natural products has not previously been reported.

The absolute configurations of agelasphins were elucidated by the total synthesis. 2772 T. NATORI ef al. separated by conventional TLC. The less polar fraction showed stronger in viva antitumor activity than the more polar fraction. Reversed-phase HPLC facilitated separation of the less polar fraction to give two major components, AGL-10 (1) and -12 (2). Additionally, HPLC separation of the other fraction gave six components AGL-7a (3), 7b (4), 9a (5). 9b (a), 11 (7) and 13 (8). The 1% NMR data of all AGLs are summarized in Table 1.

Table 1 W NMR Spectral Data of Agelasphins carbmicwnpound 1 2 3 4 5 5 5 7' 5 Longchain bass 1 (1) 2 (Q 3 (Q 4 (Q 5 OKQ 6 (9 7 (Q 6 (Q 0 (a) 10 (Q 11 (Q 10 (s) nuwul (s) ho f ad-64) ii FatIyacid 1' (s) 2' (d) 3 (0 4'(t) al.3 sugar 1' (Q 2' (Q 3' (Q f I: . 6 0)