Kabirimine, a New Cyclic Imine from an Okinawan Dinoflagellate

Marine Drugs

Takahiro Haruyama¹  Nobuyuki Kobayashi¹  Shoichiro Suda²  Junichi Tanaka²  Masahiro Higashi³  Mikako Higa⁴  PhilipusUli Basa Hutabarat⁴  Idam Hermawan⁴  Kiyotaka Akiyama⁵  Takeshi Fujiwara⁵  Akihiko Kanamoto⁵ 

[1] Central Research Center, AVSS Corporation, Nagasaki 852-8137, Japan;Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan;Department of Molecular Engineering, Kyoto University, Kyoto 615-8510, Japan;Graduate School of Engineering and Science, University of the Ryukyus, Senbaru 1, Nishihara, Okinawa 903-0213, Japan;OP Bio Factory Co., Ltd., Okinawa Life Science Center 107, 5-8 Suzaki, Uruma, Okinawa 904-02234, Japan;

关键词: cyclic imine;    dinoflagellate;    respiratory syncytial virus (RSV);    portimine;    kabirimine;   

DOI  :  10.3390/md17060353

来源: DOAJ

【 摘 要 】

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).

【 授权许可】

Unknown