Structure-activity relationships of alkaloids from mesquite (Prosopis juliflora (Sw.) DC.)
Structure-activity relationships of alkaloids from mesquite (Prosopis juliflora (Sw.) DC.)
复制标题
DOI：
10.1007/s10725-004-5574-8
复制
发表时间：
2004-11-01
影响因子：
4.2
通讯作者：
Hasegawa, K
中科院分区：
文献类型：
--
作者：
Nakano, H;Nakajima, E;Hasegawa, K
以豆科植物生物碱（1 - 5）对单子叶植物稗草、水稻和梯牧草，双子叶植物苋菜、莴苣和水芹的地上部和根系生长的抑制作用为研究对象，研究了生物碱（1 - 5）的构效关系。所有测试的生物碱通常显示对单子叶和双子叶植物的生长抑制。此外，这些生物碱对所有植物的根生长的抑制活性均高于对地上部的抑制活性，但对水稻幼苗的地上部生长的抑制活性高于对根生长的抑制活性。在这些生物碱中，活性最高的化合物似乎是juliprosine（4），其次是3-氧代-和3 '-氧代- juliprosine（3a和3b）的（1：1）混合物，以及juliprosopine（5）。2-甲基哌啶在C-3和C-3'位带有羟基的尤立普辛（4）的活性高于3-氧代-和3'-氧代-2-甲基哌啶的3-氧代-和3 '-氧代-尤立普辛（3a和3b）。含二氢中氮茚鎓环的化合物3和4比含四氢中氮茚环的化合物5显示出更高的活性，而含四氢中氮茚酮环的化合物1显示出更弱的活性。不含中氮茚环的secojuliprosopinal（2）活性很弱。这说明了牧豆树生物碱化学结构中的活性部位是哌啶和中氮茚骨架C-3和C-3'位的官能团。
The structure - activity relationships of alkaloids ( 1 - 5) from mesquite were subjected to assessment of growth inhibition against the shoot and root growth of monocotyledonous plants, barnyard grass, rice and timothy, and dicotyledonous ones, amaranth, lettuce and cress. All alkaloids tested generally showed growth inhibitory against both monocotyledonous and dicotyledonous plants. Furthermore, these alkaloids exhibited higher activity against the growth of root than that of shoot of all plant species used, except that juliprosopine ( 5) showed higher activity against the shoot growth than the root growth of rice seedling. Among these alkaloids, the highest active compound appeared to be juliprosine ( 4), followed by a ( 1: 1) mixture of 3- oxo- and 3'- oxo- juliprosine (3a and 3b), and juliprosopine ( 5). The activity of juliprosine ( 4) containing 2-methyl piperidine bearing hydroxyl groups at C-3 and C-3' was higher than that of 3- oxo- and 3'- oxo- juliprosine ( 3a and 3b) containing 3- oxo- and 3'- oxo- 2- methylpiperidine. Compound 3 and 4 containing dihydroindolizinium ring showed higher activity than compound 5 containing tetrahydroindolizine ring, whereas compound 1 containing tetrahydroindolizinone ring showed weaker activity. The activity of secojuliprosopinal ( 2) without indolizine ring was very weak. It was thus clarified that the active sites in the chemical structure of alkaloids from mesquite are the functional group at C-3 and C-3' of piperidine and indolizine skeleton.