†Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970 São Carlos, SP, Brazil.
‡School of Chemistry, Bangor University, Bangor, Gwynedd LL57 2UW, U.K.
J Nat Prod. 2015 May 22;78(5):1101-12. doi: 10.1021/acs.jnatprod.5b00070. Epub 2015 Apr 29.
HPLC-UV-ELSD-MS-guided fractionation of the anti-parasitic extract obtained from the marine sponge Monanchora arbuscula, collected off the southeastern coast of Brazil, led to the isolation of a series of guanidine and pyrimidine alkaloids. The pyrimidines monalidine A (1) and arbusculidine A (7), as well as the guanidine alkaloids batzellamide A (8) and hemibatzelladines 9-11, represent new minor constituents that were identified by analysis of spectroscopic data. The total synthesis of monalidine A confirmed its structure. Arbusculidine A (7), related to the ptilocaulin/mirabilin/netamine family of tricyclic guanidine alkaloids, is the first in this family to possess a benzene ring. Batzellamide A (8) and hemibatzelladines 9-11 represent new carbon skeletons that are related to the batzelladines. Evaluation of the anti-parasitic activity of the major known metabolites, batzelladines D (12), F (13), L (14), and nor-L (15), as well as of synthetic monalidine A (1), against Trypanosoma cruzi and Leishmania infantum is also reported, along with a detailed investigation of parasite cell-death pathways promoted by batzelladine L (14) and norbatzelladine L (15).
从巴西东南沿海采集的海洋海绵 Monanchora arbuscula 的抗寄生虫提取物进行 HPLC-UV-ELSD-MS 分离，得到一系列胍和嘧啶生物碱。嘧啶类化合物 monalidine A（1）和 arbusculidine A（7），以及胍生物碱 batzellamide A（8）和半 batzelladines 9-11，是通过分析光谱数据鉴定的新的次要成分。monalidine A 的全合成证实了其结构。与 ptilocaulin/mirabilin/netamine 三环胍生物碱家族相关的 arbusculidine A（7）是该家族中第一个具有苯环的化合物。batzellamide A（8）和半 batzelladines 9-11 代表与 batzelladines 相关的新碳骨架。还报告了主要已知代谢产物 batzelladines D（12）、F（13）、L（14）和 nor-L（15）以及合成的 monalidine A（1）对 Trypanosoma cruzi 和 Leishmania infantum 的抗寄生虫活性的评估，以及 batzelladine L（14）和 norbatzelladine L（15）促进寄生虫细胞死亡途径的详细研究。
