Tropane alkaloids from the Australian plant Triunia montana (Proteaceae)

被引：5
作者：
Yang, Fan [1 ]
Zhao, Huijun [1 ]
Carroll, Anthony R. [1 ,2 ]
机构：
[1] Griffith Univ, Environm Futures Res Inst, Griffith Sch Environm, Gold Coast Campus,Parklands Dr, Southport, Qld 4222, Australia
[2] Griffith Univ, Eskitis Inst, Brisbane Innovat Pk,Don Young Rd, Nathan, Qld 4111, Australia
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 08期
关键词：
Proteaceae; Triunia montana; Tropane alkaloids; gamma-Pyranotropane; 2,3-Dihydrodarlingine; DARLINGIA-DARLINGIANA; GAMMA-PYRANOTROPANES; KNIGHTIA-STROBILINA; NEW-CALEDONIA; LIGANDS; 2-BENZYLTROPANES; ANTAGONISTS; AGONISTS;
D O I：
10.1016/j.tetlet.2017.01.021
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Four tropane alkaloids, including a new compound triuniamine A (3) a known compound 2,3-dihydrodar-lingine (4) with previously unassigned relative configuration and two known compounds darlingine (1), 10-hydroxydarlingine (2) were obtained from the stems of the endemic Australian plant Triunia montana (Proteaceae). The structure and relative configuration of the stereogenic centers in triuniamine A was elucidated on the basis of 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. The relative configuration of the four stereogenic centers in 2,3-dihydrodarlingine were established from ROESY correlations, and its absolute configuration assigned from comparison of its ECD spectrum with that of (+)-darlingine. (C) 2017 Elsevier Ltd. All rights reserved.
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收藏
页码：736 / 739
页数：4
相关论文
共 25 条
  • [1] BIOGENESIS OF PROTEACEOUS ALKALOIDS
    BICK, IRC
    GILLARD, JW
    LEOW, HM
    LOUNASMAA, M
    PUSSET, J
    SEVENET, T
    [J]. PLANTA MEDICA, 1981, 41 (04) : 379 - 385
  • [2] ALKALOIDS OF AGASTACHYS-ODORATA
    BICK, IRC
    GILLARD, JW
    LEOW, HM
    PRESTON, NW
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (09) : 2071 - 2076
  • [3] ALKALOIDS OF BELLENDENA-MONTANA
    BICK, IRC
    GILLARD, JW
    LEOW, HM
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (08) : 1827 - 1840
  • [4] ALKALOIDS OF DARLINGIA-DARLINGIANA
    BICK, IRC
    GILLARD, JW
    LEOW, HM
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1979, 32 (11) : 2523 - 2536
  • [5] 10-hydroxydarlingine, a new tropane alkaloid from the Australian proteaceous plant Triunia erythrocarpa
    Butler, MS
    Katavic, PL
    Davis, RA
    Forster, PI
    Guymer, GP
    Quinn, RJ
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 688 - 689
  • [6] Novel tricyclic Δ2-isoxazoline and 3-oxo-2-methyl-isoxazolidine derivatives: Synthesis and binding affinity at neuronal nicotinic acetylcholine receptor subtypes
    Dallanoce, Clelia
    Frigerio, Fabio
    Martelli, Giuliana
    Grazioso, Giovanni
    Matera, Carlo
    Pome, Diego Yuri
    Pucci, Luca
    Clementi, Francesco
    Gotti, Cecilia
    De Amici, Marco
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (12) : 4498 - 4508
  • [7] Nicotinic agonists, antagonists, and modulators from natural sources
    Daly, JW
    [J]. CELLULAR AND MOLECULAR NEUROBIOLOGY, 2005, 25 (3-4) : 513 - 552
  • [8] 3D QSAR analyses-guided rational design of novel ligands for the (α4)2(β2)3 nicotinic acetylcholine receptor
    Gohlke, H
    Schwarz, S
    Gündisch, D
    Tilotta, MC
    Weber, A
    Wegge, T
    Seitz, G
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (11) : 2031 - 2048
  • [9] Synthesis and evaluation of diazine containing bioisosteres of (-)-ferruginine as ligands for nicotinic acetylcholine receptors
    Gündisch, D
    Harms, K
    Schwarz, S
    Seitz, G
    Stubbs, MT
    Wegge, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (10) : 2683 - 2691
  • [10] Jin D, 2009, SHIZHEN GUOYI GUOYAO, V20, P28
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