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Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate
- Hermawan, Idam, Higa, Mikako, Hutabarat, Philipus Uli Basa, Fujiwara, Takeshi, Akiyama, Kiyotaka, Kanamoto, Akihiko, Haruyama, Takahiro, Kobayashi, Nobuyuki, Higashi, Masahiro, Suda, Shoichiro, Tanaka, Junichi
- Marine drugs 2019 v.17 no.6
- Miozoa, Respiratory syncytial virus, antiviral properties, bioactive compounds, cytotoxicity, derivatization, imines, isomers, spectral analysis, stereochemistry
- On our quest for new bioactive molecules from marine sources, two cyclic imines (1, 2) were isolated from a dinoflagellate extract, inhibiting the growth of the respiratory syncytial virus (RSV). Compound 1 was identified as a known molecule portimine, while 2 was elucidated to be a new cyclic imine, named kabirimine. The absolute stereochemistry of 1 was determined by crystallographic work and chiral derivatization, whereas the structure of 2 was elucidated by means of spectroscopic analysis and computational study on all the possible isomers. Compound 1 showed potent cytotoxicity (CC<inf>50</inf> < 0.097 µM) against HEp2 cells, while 2 exhibited moderate antiviral activity against RSV with IC<inf>50</inf> = 4.20 µM (95% CI 3.31–5.33).