Neuritogenic cerebrosides from an edible Chinese mushroom. Part 2: Structures of two additional termitomycesphins and activity enhancement of an inactive cerebroside by hydroxylation.
Termitomycesphins E and F, novel cerebrosides that are hydroxylated around the middle of the long-chain base (LCB), have been isolated from the edible Chinese mushroom Termitomyces albuminosus (Berk.) Heim. ('Jizong' in Chinese) together with termitomycesphins A-D, and shown to induce neuronal differentiation in rat PC12 cells. Their stereostructures have been determined based on their chemical derivatization and spectroscopic analysis. The major cerebroside obtained from the same mushroom was not hydroxylated around the middle of the LCB and was inactive against PC12 cells, suggesting the importance of the extra hydroxyl group on LCB. The Di- and tetrahydroxylation of this inactive cerebroside resulted in the enhancement of its neuritogenic activity.
Qi
J
J
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa-ku, 464-8601, Japan.
Ojika
M
M
Sakagami
Y
Y
D000363:Agaricales / Q000737:chemistry*; D000818:Animals; D002454:Cell Differentiation / Q000187:drug effects; D002554:Cerebrosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006900:Hydroxylation; D009474:Neurons / Q000166:cytology / Q000187:drug effects; D016716:PC12 Cells; D051381:Rats
D002554:Cerebrosides; C434756:termitomycesphin E; C434755:termitomycesphin F