Absolute stereochemistry and antitumor activity of iejimalides.
The absolute configurations at five chiral centers, except for C-32(S) reported previously, in iejimalides A, C, and D, potent cytotoxic 24-membered macrolides isolated from a tunicate Eudistoma cf. rigida, were assigned as 4R, 9S, 17S, 22S, and 23S on the basis of detailed analysis of NMR data and chemical means. Furthermore, the structures proposed for iejimalides A, C, and D were revised to their 13Z-isomers. Iejimalides A-D (1-4) exhibited antitumor activity in vivo.
Nozawa
Kohei
K
Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Tsuda
Masashi
M
Ishiyama
Haruaki
H
Sasaki
Takuma
T
Tsuruo
Takashi
T
Kobayashi
Jun'ichi
J
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002942:Circular Dichroism; D006801:Humans; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014561:Urochordata / Q000737:chemistry; D023041:Xenograft Model Antitumor Assays
D000970:Antineoplastic Agents; D018942:Macrolides