FUNGAL METABOLITES .12. POTENT IMMUNOSUPPRESSANT, 14-DEOXOMYRIOCIN, (2S,3R,4R)-(E)-2-AMINO-3,4-DIHYDROXY-2-HYDROXYMETHYLEICOS-6-ENOIC ACID AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF MYRIOCIN DERIVATIVES

In order to investigate the structure-activity relationships, fourteen derivatives of myriocin ((2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-14-oxoeicos-6-enoic acid) were prepared and examined for immunosuppressive activity on mouse allogeneic mixed lymphocyte reaction in vitro. Among them, 14-deoxomyriocin ((2S,3R,4R)-(E)-2-amino-3,4-dihydroxy-2-hydroxymethyl-eicos-6-enoic acid) was the most potent. It also suppressed the generation of allo-reactive cytotoxic T lymphocytes in mice upon intraperitoneal administration, with a potency 10-fold greater than that of myriocin.