Marine Drugs (Jun 2019)

Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

  • Idam Hermawan,
  • Mikako Higa,
  • Philipus Uli Basa Hutabarat,
  • Takeshi Fujiwara,
  • Kiyotaka Akiyama,
  • Akihiko Kanamoto,
  • Takahiro Haruyama,
  • Nobuyuki Kobayashi,
  • Masahiro Higashi,
  • Shoichiro Suda,
  • Junichi Tanaka

DOI
https://doi.org/10.3390/md17060353
Journal volume & issue
Vol. 17, no. 6
p. 353

Abstract

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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 (CC50 < 0.097 µM) against HEp2 cells, while 2 exhibited moderate antiviral activity against RSV with IC50 = 4.20 µM (95% CI 3.31−5.33).

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