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.
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.
Fujita
T
T
Faculty of Pharmaceutical Sciences, Kyoto University, Japan.
Inoue
K
K
Yamamoto
S
S
Ikumoto
T
T
Sasaki
S
S
Toyama
R
R
Yoneta
M
M
Chiba
K
K
Hoshino
Y
Y
Okumoto
T
T
D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis / Q000494:pharmacology*; D005658:Fungi / Q000378:metabolism; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D007959:Lymphocyte Culture Test, Mixed; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C086653:14-deoxomyriocin; D000935:Antifungal Agents; D005229:Fatty Acids, Monounsaturated; D007166:Immunosuppressive Agents; C001996:thermozymocidin