Structure elucidation and biomimetic synthesis of hostasinine A, a new benzylphenethylamine alkaloid from Hosta plantaginea.
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.
Wang
Yue-Hu
YH
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.
Gao
Suo
S
Yang
Fu-Mei
FM
Sun
Qian-Yun
QY
Wang
Jun-Song
JS
Liu
Hai-Yang
HY
Li
Chun-Shun
CS
Di
Ying-Tong
YT
Li
Shun-Lin
SL
He
Hong-Ping
HP
Hao
Xiao-Jiang
XJ
D000143:Acids / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D031422:Hosta / Q000737:chemistry*; D015394:Molecular Structure; D010627:Phenethylamines / Q000138:chemical synthesis / Q000737:chemistry*
D000143:Acids; D000470:Alkaloids; D010627:Phenethylamines; C526096:hostasinine A; D001554:Benzene