• Title/Summary/Keyword: Lupanine

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Rhombifiline and 5,6-Dehydrolupanine from Angyrus foetida L.

  • M.M.Al-Azizi;M.S. Al-Saidl;M.M.El-Olemy;E.Abde Sattar;A.S.Khalifa
    • Archives of Pharmacal Research
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    • v.17 no.6
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    • pp.393-397
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    • 1994
  • Rhomobifoline and 5,6-dehydrolupanine were isolated for the frist time from the leaves and stems of A. foetida L. indigenous to Saudil Arabia. In addition, five other alkaloids, previously identified in A, foetidia L., namely N-methylcytisine, sparteine, anagyrine, lupanine and cytisine, were isolated. The isolated alkaloids were characterized by UV, $^1-NMR,{\;}^{13}H-NMR,{\;}^{13}C-NMR{\;}and{\;}Mass{\;}spectral{\;}data.{\;}^{13}C-NMR$ data of rhombifoline and 5,6-dehydroupanine are reported for the first time.

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Mechanistic Studies for Electrochemical Oxidation of ${\iota}$-Sparteine (${\iota}$-Sparteine의 전기화학적 산화반응에 대한 메카니즘의 연구)

  • Jin-Hyo Park;Chang-Soo Jin;Sung-Nak Choi;Yoon-Bo Shim
    • Journal of the Korean Chemical Society
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    • v.37 no.8
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    • pp.711-716
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    • 1993
  • The mechanism for electrochemical oxidation of natural alkaloid, ${\iota}$-sparteine (SP) was studied in acetonitrile solvent. The cyclic voltammogram of SP shows two irreversible anodic peaks at +0.75 V and +1.45 V vs. Ag/AgCl (0.1M AgNO$_2$ in acetonitrile) electrode. Coulometry reveals that the number of electrons involved in each oxidation peaks is in the range of 1.2∼1.3 respectively. Neutral imine radical was produced by fast deprotonation of SP radical cation formed by oxidation of one nitrogen atom in SP. Two pathways are possible for the reaction of the neutral radical: Due to the disproportionation of the radical, SP and enamine were mainly produced. Also, the 1,2-dehydrosparteinium cation was formed as minor product through the second one electron transfer oxidation of this radical. The (+)-lupanine was produced by treatment of sparteinium cation with potassium hydroxide. We have isolated and confirmed the electrolysis products using IR, GC-MS, UV-Vis, and thin-layer spectroelectrochemical method.

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