Laurella Laura C, Cerny Natacha, Bivona Augusto E, Sánchez Alberti Andrés, Giberti Gustavo, Malchiodi Emilio L, Martino Virginia S, Catalan Cesar A, Alonso María Rosario, Cazorla Silvia I, Sülsen Valeria P
Universidad de Buenos Aires, Facultad de Farmacia y Bioquímica, Cátedra de Farmacognosia, Buenos Aires, Argentina.
CONICET-Universidad Nacional de Luján, Instituto de Ecología y Desarrollo Sustentable (INEDES), Luján, Argentina.
PLoS Negl Trop Dis. 2017 Sep 25;11(9):e0005929. doi: 10.1371/journal.pntd.0005929. eCollection 2017 Sep.
Four sesquiterpene lactones, mikanolide, deoxymikanolide, dihydromikanolide and scandenolide, were isolated by a bioassay-guided fractionation of Mikania variifolia and Mikania micrantha dichloromethane extracts. Mikanolide and deoxymikanolide were the major compounds in both extracts (2.2% and 0.4% for Mikania variifolia and 21.0% and 6.4% for Mikania micrantha respectively, calculated on extract dry weight). Mikanolide, deoxymikanolide and dihydromikanolide were active against Trypanosoma cruzi epimastigotes (50% inhibitory concentrations of 0.7, 0.08 and 2.5 μg/mL, for each compound respectively). These sesquiterpene lactones were also active against the bloodstream trypomastigotes (50% inhibitory concentrations for each compound were 2.1, 1.5 and 0.3 μg/mL, respectively) and against amastigotes (50% inhibitory concentrations for each compound were 4.5, 6.3 and 8.5 μg/mL, respectively). By contrast, scandenolide was not active on Trypanosoma cruzi. Besides, mikanolide and deoxymikanolide were also active on Leishmania braziliensis promastigotes (50% inhibitory concentrations of 5.1 and 11.5 μg/mL, respectively). The four sesquiterpene lactones were tested for their cytotoxicity on THP 1 cells. Deoxymikanolide presented the highest selectivity index for trypomastigotes (SI = 54) and amastigotes (SI = 12.5). In an in vivo model of Trypanosoma cruzi infection, deoxymikanolide was able to decrease the parasitemia and the weight loss associated to the acute phase of the parasite infection. More importantly, while 100% of control mice died by day 22 after receiving a lethal T. cruzi infection, 70% of deoxymikanolide-treated mice survived. We also observed that this compound increased TNF-α and IL-12 production by macrophages, which could contribute to control T. cruzi infection.
通过生物活性导向的分离方法,从薇甘菊和小花蔓泽兰的二氯甲烷提取物中分离出了四种倍半萜内酯,即米卡诺内酯、脱氧米卡诺内酯、二氢米卡诺内酯和藤菊内酯。米卡诺内酯和脱氧米卡诺内酯是两种提取物中的主要化合物(按提取物干重计算,薇甘菊中分别为2.2%和0.4%,小花蔓泽兰中分别为21.0%和6.4%)。米卡诺内酯、脱氧米卡诺内酯和二氢米卡诺内酯对克氏锥虫前鞭毛体具有活性(每种化合物的50%抑制浓度分别为0.7、0.08和2.5μg/mL)。这些倍半萜内酯对血液中的锥鞭毛体也具有活性(每种化合物的50%抑制浓度分别为2.1、1.5和0.3μg/mL),对无鞭毛体同样具有活性(每种化合物的50%抑制浓度分别为4.5、6.3和8.5μg/mL)。相比之下,藤菊内酯对克氏锥虫无活性。此外,米卡诺内酯和脱氧米卡诺内酯对巴西利什曼原虫前鞭毛体也具有活性(50%抑制浓度分别为5.1和11.5μg/mL)。对这四种倍半萜内酯进行了对THP - 1细胞的细胞毒性测试。脱氧米卡诺内酯对锥鞭毛体(SI = 54)和无鞭毛体(SI = 12.5)表现出最高的选择性指数。在克氏锥虫感染的体内模型中,脱氧米卡诺内酯能够降低寄生虫感染急性期相关的寄生虫血症和体重减轻。更重要的是,在接受致死性克氏锥虫感染后,100%的对照小鼠在第22天死亡,而70%接受脱氧米卡诺内酯治疗的小鼠存活。我们还观察到该化合物增加了巨噬细胞产生的TNF - α和IL - 12,这可能有助于控制克氏锥虫感染。