Moreno-Velasco Armando, Flores-Tafoya Pedro de Jesús, Fragoso-Serrano Mabel, Leitão Suzana Guimarães, Pereda-Miranda Rogelio
Departamento de Farmacia, Facultad de Química and Programa de Maestría y Doctorado en Ciencias Químicas, Universidad Nacional Autónoma de México, Ciudad Universitaria, Mexico City 04510, Mexico.
Faculdade de Farmacia, Universidade Federal do Rio de Janeiro, CCS, Bloco A, Ilha do Fundão, Rio de Janeiro 21941-902, Brazil.
J Nat Prod. 2022 Oct 28;85(10):2385-2394. doi: 10.1021/acs.jnatprod.2c00594. Epub 2022 Sep 26.
is a vine native to the north and northeast region of Brazil, where its roots are traded as a depurative and laxative remedy with the name of Brazilian jalap in traditional medicine. Procedures for the isolation, purification by recycling HPLC, and structure elucidation of three undescribed resin glycosides are presented herein. Hamiltonin I () represents a macrocyclic structure of a tetrasaccharide of (11)-hydroxyhexadecanoic acid. Additionally, two acyclic pentasaccharides, named hamiltoniosides I () and II (), were also isolated, which are related structurally to the known compounds and , macrocyclic lactone-type batatinosides. The tetrasaccharide core of was diacylated by -decanoic acid and the unusual -hexadecanoic acid moiety, while the pentasaccharides - were esterified by one unit of -decanoic or -dodecanoic acid. All the isolated compounds were found to be inactive as cytotoxic agents. However, when they were evaluated (1-25 μM) in combination with a sublethal concentration of the anticancer agent vinblastine (0.003 μM), a significant enhancement of the resultant cytotoxicity was produced, especially for multidrug-resistant breast carcinoma epithelial cells. Such combined synergistic potency may be beneficial for chemotherapy, making resin glycosides potential candidates for drug repurposing of conventional chemotherapeutic drugs to reduce their side effects.
它是一种原产于巴西北部和东北部地区的藤本植物，在传统医学中，其根作为一种净化和泻药出售，名为巴西药喇叭。本文介绍了三种未描述的树脂糖苷的分离、循环高效液相色谱法纯化及结构解析过程。哈密顿素I（）代表一种（11）-羟基十六烷酸四糖的大环结构。此外，还分离出两种无环五糖，分别命名为哈密顿糖苷I（）和II（），它们在结构上与已知化合物和大环内酯型巴塔糖苷有关。的四糖核心被癸酸和不寻常的十六烷酸部分二酰化，而五糖被一个癸酸或十二烷酸单元酯化。所有分离出的化合物均被发现无细胞毒性。然而，当它们与亚致死浓度的抗癌药物长春碱（0.003μM）联合评估（1-25μM）时，产生了显著增强的细胞毒性，尤其是对多药耐药乳腺癌上皮细胞。这种联合协同效力可能对化疗有益，使树脂糖苷成为传统化疗药物重新利用以减少其副作用的潜在候选药物。
