J Antibiot (Tokyo). 1994
Feb;47(2):216-24.
Fungal metabolites.
Part 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.
Fujita T, Inoue
K, Yamamoto S, Ikumoto T, Sasaki S, Toyama
R, Yoneta M, Chiba K, Hoshino Y, Okumoto T.
Faculty of Pharmaceutical Sciences, Kyoto
University, Japan.
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-
hydroxymethyleicos-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.
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