Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

On our quest for new bioactive molecules from marine sources, two cyclic imines (<b>1</b>, <b>2</b>) were isolated from a dinoflagellate extract, inhibiting the growth of the respiratory syncytial virus (RSV). Compound <b>1</b> was identified as a known molecule p...

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Bibliographic Details
Main Authors: Idam Hermawan, Mikako Higa, Philipus Uli Basa Hutabarat, Takeshi Fujiwara, Kiyotaka Akiyama, Akihiko Kanamoto, Takahiro Haruyama, Nobuyuki Kobayashi, Masahiro Higashi, Shoichiro Suda, Junichi Tanaka
Format: Article
Language:English
Published: MDPI AG 2019-06-01
Series:Marine Drugs
Subjects:
Online Access:https://www.mdpi.com/1660-3397/17/6/353
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Summary:On our quest for new bioactive molecules from marine sources, two cyclic imines (<b>1</b>, <b>2</b>) were isolated from a dinoflagellate extract, inhibiting the growth of the respiratory syncytial virus (RSV). Compound <b>1</b> was identified as a known molecule portimine, while <b>2</b> was elucidated to be a new cyclic imine, named kabirimine. The absolute stereochemistry of <b>1</b> was determined by crystallographic work and chiral derivatization, whereas the structure of <b>2</b> was elucidated by means of spectroscopic analysis and computational study on all the possible isomers. Compound <b>1</b> showed potent cytotoxicity (CC<sub>50</sub> &lt; 0.097 &#181;M) against HEp2 cells, while <b>2</b> exhibited moderate antiviral activity against RSV with IC<sub>50</sub> = 4.20 &#181;M (95% CI 3.31&#8722;5.33).
ISSN:1660-3397