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Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

Author:
Hermawan, Idam, Higa, Mikako, Hutabarat, Philipus Uli Basa, Fujiwara, Takeshi, Akiyama, Kiyotaka, Kanamoto, Akihiko, Haruyama, Takahiro, Kobayashi, Nobuyuki, Higashi, Masahiro, Suda, Shoichiro, Tanaka, Junichi
Source:
Marine drugs 2019 v.17 no.6
ISSN:
1660-3397
Subject:
Miozoa, Respiratory syncytial virus, antiviral properties, bioactive compounds, cytotoxicity, derivatization, imines, isomers, spectral analysis, stereochemistry
Abstract:
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 &micro;M) against HEp2 cells, while 2 exhibited moderate antiviral activity against RSV with IC<inf>50</inf> = 4.20 &micro;M (95% CI 3.31&ndash;5.33).
Agid:
6497892