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首页> 外文期刊>RSC Advances >Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B-3 and B-4, and related 5,8 '-coupled monomeric alkaloids, ikelacongolines A-D, from a Congolese Ancistrocladus liana
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Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B-3 and B-4, and related 5,8 '-coupled monomeric alkaloids, ikelacongolines A-D, from a Congolese Ancistrocladus liana

机译：反共酶二聚体萘氨基喹啉，M麦克卡胺B-3和B-4，以及相关5,8' -coupled单体生物碱，Ikelacongolines A-D，来自刚果猿猴子

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摘要

From the leaves of a botanically and phytochemically as yet unexplored Ancistrocladus liana discovered in the rainforests of the Central region of the Democratic Republic of the Congo in the vicinity of the town of Ikela, six new naphthylisoquinoline alkaloids were isolated, viz., two constitutionally unsymmetric dimers, the mbandakamines B-3 (3) and B-4 (4), and four related 5,8-linked monomeric alkaloids, named ikelacongolines A-D (5a, 5b, 6, and 7). The dimers 3 and 4 are structurally unusual quateraryls comprising two 5,8-coupled monomers linked via a sterically strongly constrained 6,1-connection between their naphthalene units. These compounds contain seven elements of chirality, four stereogenic centers and three consecutive chiral axes. They were identified along with two known related compounds, the mbandakamines A (1) and B-2 (2), which had so far only been detected in two Ancistrocladus species indigenous to the Northwestern Congo Basin. In addition, five known monomeric alkaloids, previously found in related Central African Ancistrocladus species, were isolated from the here investigated Congolese liana, three of them belonging to the subclass of 5,8-coupled naphthylisoquinoline alkaloids, whereas two compounds exhibited a less frequently occurring 7,8-biaryl linkage. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR), chemical (oxidative degradation), and chiroptical (electronic circular dichroism) methods. The mbandakamines B-3 (3) and B-4 (4) displayed pronounced activities in vitro against the malaria parasite Plasmodium falciparum and the pathogen of African sleeping sickness, Trypanosoma brucei rhodesiense.
机译：从唯一的刚果民主共和国中央地区的雨林中发现的植物园的植物叶片，六个新的萘甲基喹啉生物碱被隔离，八宪章。，二宪章二聚体，m茂密蛋白胨B-3（3）和B-4（4）和四种相关的5,8-连接的单体生物碱，称为Ikelacongolines Ad（5a，5b，6和7）。二聚体3和4是在结构上不寻常的四边构，其包含通过在其萘单元之间的空间受强度约束的6,1连接的两种5,8偶联单体。这些化合物含有七种手性，四个立体中心和三个连续的手性轴。鉴定它们以及两种已知的相关化合物，Mangakamines A（1）和B-2（2）鉴定，这只迄今为止仅在西北刚果盆地的两种血份流浪者物种中检测到。此外，从这里发现的五种已知的单体生物碱，以前在相关中非血栓儿童物种中被分离出来的刚果莲，其中三个属于5,8-偶联的萘基喹啉生物碱的亚类，而两种化合物呈现不太频繁的7,8-Biarall联系。通过光谱法（特别是Hresims，1D和2D NMR），化学（氧化降解）和含羞于（电子圆形二中型）方法建立新生物碱的立体结构。 Mabyakamines B-3（3）和B-4（4）在体外显示出对疟疾寄生虫疟原虫的明显活动和非洲睡眠疾病的病原体，TrypanoSoma Brucei Rhodesiense。

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  • 来源
    《RSC Advances》 |2019年第21期|共13页
  • 作者

    Mufusama Jean-Pierre; Feineis Doris; Mudogo Virima; Kaiser Marcel; Brun Reto; Bringmann Gerhard;

  • 作者单位

    Univ Wurzburg Inst Organ Chem D-97074 Wurzburg Germany;

    Univ Wurzburg Inst Organ Chem D-97074 Wurzburg Germany;

    Univ Kinshasa Fac Sci BP 202 Kinshasa XI DEM REP CONGO;

    Swiss Trop &

    Publ Hlth Inst Socinstr 57 CH-4002 Basel Switzerland;

    Swiss Trop &

    Publ Hlth Inst Socinstr 57 CH-4002 Basel Switzerland;

    Univ Wurzburg Inst Organ Chem D-97074 Wurzburg Germany;

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