Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
J Nat Prod. 2009 Feb 27;72(2):312-5. doi: 10.1021/np800743w.
The hyphenated technique HPLC-PDA-MS-SPE-NMR was used to assist targeted preparative-scale isolation of constituents of Lobelia siphilitica and Hippobroma longiflora (both Campanulaceae). This resulted in the isolation of two new alkaloids, (S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate (3) and 6-[(E)-2-(3-methoxyphenyl)ethenyl]-2,3,4,5-tetrahydropyridine (4), the latter possessing a skeleton hitherto unseen among alkaloids of Lobelia and related genera. Lobeline (1), (1S,1'S)-2,2'-[(2R,6S)-1-methylpiperidine-2,6-diyl]bis(1-phenylethanol) (2), and lobetyolin (5) were also isolated. The structures of 1-5 were established using spectroscopic methods including homo- and heteronuclear two-dimensional NMR experiments and optical rotation data.
采用 HPLC-PDA-MS-SPE-NMR 技术辅助靶向制备分离半边莲和长序山蚂蝗(均为桔梗科)的成分。这导致了两种新生物碱的分离,(S)-2-[(2S,6R)-1-甲基-6-(2-氧代-2-苯乙基)哌啶-2-基]-1-苯乙基乙酸酯(3)和 6-[(E)-2-(3-甲氧基苯基)乙烯基]-2,3,4,5-四氢吡啶(4),后者具有迄今未见的半边莲和相关属生物碱骨架。还分离出了洛贝林(1)、(1S,1'S)-2,2'-[(2R,6S)-1-甲基哌啶-2,6-二基]双(1-苯乙醇)(2)和洛贝替林(5)。通过包括同核和异核二维 NMR 实验以及旋光数据在内的光谱方法确定了 1-5 的结构。