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Open AccessArticle

Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

1
Graduate School of Engineering and Science, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan
2
OP Bio Factory Co., Ltd., Okinawa Life Science Center 107, 5-8 Suzaki, Uruma, Okinawa 904-02234, Japan
3
Central Research Center, AVSS Corporation, Nagasaki 852-8137, Japan
4
Department of Molecular Engineering, Kyoto University, Kyoto 615-8510, Japan
5
Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(6), 353; https://doi.org/10.3390/md17060353
Received: 31 May 2019 / Revised: 10 June 2019 / Accepted: 11 June 2019 / Published: 13 June 2019
(This article belongs to the Special Issue Marine Natural Products Discovery: In Honor of Late Prof. Tatsuo Higa)
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). View Full-Text
Keywords: cyclic imine; dinoflagellate; respiratory syncytial virus (RSV); portimine; kabirimine cyclic imine; dinoflagellate; respiratory syncytial virus (RSV); portimine; kabirimine
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MDPI and ACS Style

Hermawan, I.; Higa, M.; Hutabarat, P.U.B.; Fujiwara, T.; Akiyama, K.; Kanamoto, A.; Haruyama, T.; Kobayashi, N.; Higashi, M.; Suda, S.; Tanaka, J. Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate. Mar. Drugs 2019, 17, 353.

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