Structure elucidation and biomimetic synthesis of hostasinine A, a new benzylphenethylamine alkaloid from Hosta plantaginea.

Yue-Hu Wang, Suo Gao, Fu-Mei Yang, Qian-Yun Sun, Jun-Song Wang, Hai-Yang Liu, Chun-Shun Li, Ying-Tong Di, Shun-Lin Li, Hong-Ping He, Xiao-Jiang Hao

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.

Organic letters 2007 Dec 6

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Hostasinine A (1), a benzylphenethylamine alkaloid with an unprecedented skeleton featuring a C-4-C-6 linkage and a nitrone moiety, was isolated from Hosta plantaginea. Its structure was established on the basis of spectroscopic data, and was further confirmed by single-crystal X-ray diffraction. The alkaloid was postulated biogenetically from haemanthidine via N-oxidation and aza-aldol-type condensation and was synthesized biomimetically. The inhibitory activities of 1 on acetylcholinesterase (AChE) and two tumor cell lines (K562 and A549) were also evaluated.

Citation

Yue-Hu Wang, Suo Gao, Fu-Mei Yang, Qian-Yun Sun, Jun-Song Wang, Hai-Yang Liu, Chun-Shun Li, Ying-Tong Di, Shun-Lin Li, Hong-Ping He, Xiao-Jiang Hao. Structure elucidation and biomimetic synthesis of hostasinine A, a new benzylphenethylamine alkaloid from Hosta plantaginea. Organic letters. 2007 Dec 6;9(25):5279-81