Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 69, Issue 1, Pages 141-149Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c20-00745
Keywords
macrolide; dinoflagellate; Amphidinium; cytotoxic activity
Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [26670045]
- Grants-in-Aid for Scientific Research [26670045] Funding Source: KAKEN
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Two highly potent cytotoxic 26-membered macrolides, isocaribenolide-I and a chlorohydrin 2, were isolated from a free-swimming dinoflagellate Amphidinium species collected off Iriomote Island, Japan. The structures of these compounds were determined to be congeners of known amphidinolide N, with different end groups and chlorohydrin forms.
Two highly potent cytotoxic 26-membered macrolides, isocaribenolide-I (I) and a chlorohydrin 2, together with known amphidinolide N (3), have been isolated from a free-swimming dinoflagellate Amphidinium species (KCA09053 and KCA09056 strains) collected off Iriomote Island, Japan. The structures of 1 and 2 were determined to be a congener of 3 with an isobutyl terminus and the chlorohydrin form of 3, respectively, by detailed analyses of spectroscopic data. The relative stereochemistries of 1 and 2 were elucidated by the conformational analyses based on NMR data.
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