幻蟾肽：一种源自厄瓜多尔毒蛙（Epipedobates anthonyi）的拟海洛因肽类似物。
Phantasmidine: an epibatidine congener from the ecuadorian poison frog Epipedobates anthonyi.
机构信息
Laboratory of Bioorganic Chemistry, National Institute of Diabetes, Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, Maryland 20892, USA.
出版信息
J Nat Prod. 2010 Mar 26;73(3):331-7. doi: 10.1021/np900727e.
The skin of the Ecuadorian poison frog Epipedobates anthonyi contains the potent nicotinic agonists epibatidine (1) and N-methylepibatidine (3). In addition, a condensed tetracyclic epibatidine congener has been identified with activity at nicotinic acetylcholine receptors, but different selectivity than epibatidine. This rigid tetracycle has been named phantasmidine (4). Phantasmidine has a molecular formula of C(11)H(11)N(2)OCl, shares a chloropyridine moiety with 1, and also contains furan, pyrrolidine, and cyclobutane rings. A combination of GC-MS and GC-FTIR analysis with on-column derivatization, 1D NMR spectroscopy with selective irradiation, and spectral simulation, along with 2D NMR, were used to elucidate the structure from a total sample of approximately 20 microg of HPLC-purified 4 and its corresponding acetamide (5). After synthesis, this novel rigid agonist may serve as a selective probe for beta4-containing nicotinic receptors and potentially lead to useful pharmaceuticals.
厄瓜多尔毒蛙 Epipedobates anthonyi 的皮肤含有强效烟碱型乙酰胆碱受体激动剂——埃派丁（1）和 N-甲基埃派丁（3）。此外，还鉴定出一种具有烟碱型乙酰胆碱受体活性的稠合四环埃派丁同系物，但与埃派丁的选择性不同。这种刚性四环结构被命名为幻蝶碱（4）。幻蝶碱的分子式为 C(11)H(11)N(2)OCl，与 1 共享一个氯吡啶部分，还含有呋喃、吡咯烷和环丁烷环。通过柱上进样衍生化的 GC-MS 和 GC-FTIR 分析、选择性照射的 1D NMR 光谱和光谱模拟，以及二维 NMR，从大约 20 微克 HPLC 纯化的 4 及其相应的乙酰胺（5）的总样品中阐明了结构。合成后，这种新型刚性激动剂可能成为含有β4 的烟碱型受体的选择性探针，并可能产生有用的药物。
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