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Antibacterial and ATP Synthesis Modulating Compounds from Salvia tingitana.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-17 , DOI: 10.1021/acs.jnatprod.9b01024
Angela Bisio 1 , Anna M Schito 2 , Francesca Pedrelli 1 , Ombeline Danton 3 , Jakob K Reinhardt 3 , Giulio Poli 4 , Tiziano Tuccinardi 4 , Thomas Bürgi 5 , Francesco De Riccardis 6 , Mauro Giacomini 7 , Daniela Calzia 1 , Isabella Panfoli 1 , Gian Carlo Schito 1 , Matthias Hamburger 3 , Nunziatina De Tommasi 8
Affiliation  

A surface extract of the aerial parts of Salvia tingitana afforded a nor-sesterterpenoid (1) and eight new sesterterpenoids (2-̵9), along with five known sesterterpenoids, five labdane and one abietane diterpenoid, one sesquiterpenoid, and four flavonoids. The structures of the new compounds were established by 1D and 2D NMR spectroscopy, HRESIMS, and VCD data and Mosher's esters analysis. The antimicrobial activity of compounds was evaluated against 30 human pathogens including 27 clinical strains and three isolates of marine origin for their possible implications on human health. The methyl ester of salvileucolide (10), salvileucolide-6,23-lactone (11), sclareol (15), and manool (17) were the most active against Gram-positive bacteria. The compounds were also tested for the inhibition of ATP production in purified mammalian rod outer segments. Terpenoids 10, 11, 15, and 17 inhibited ATP production, while only 17 inhibited also ATP hydrolysis. Molecular modeling studies confirmed the capacity of 17 to interact with mammalian ATP synthase. A significant reduction of ATP production in the presence of 17 was observed in Enterococcus faecalis and E. faecium isolates.

中文翻译:

来自 Salvia tingitana 的抗菌和 ATP 合成调节化合物。

丹参地上部分的表面提取物提供了一种正二倍半萜类化合物 (1) 和八种新的倍半萜类化合物 (2-̵9),以及五种已知的倍半萜类化合物、五种拉丹烷和一种松香烷二萜类化合物、一种倍半萜类化合物和四种黄酮类化合物。通过 1D 和 2D NMR 光谱、HRESIMS、VCD 数据以及 Mosher 酯分析确定了新化合物的结构。针对 30 种人类病原体(包括 27 种临床菌株和 3 种海洋来源的分离株)评估了化合物的抗菌活性,了解它们对人类健康可能产生的影响。丹红内酯甲酯 (10)、丹红内酯-6,23-内酯 (11)、香紫苏醇 (15) 和马诺醇 (17) 对革兰氏阳性菌的活性最强。还测试了这些化合物对纯化的哺乳动物视杆外节中 ATP 产生的抑制作用。萜类化合物 10、11、15 和 17 抑制 ATP 产生,而只有 17 也抑制 ATP 水解。分子模型研究证实了 17 与哺乳动物 ATP 合酶相互作用的能力。在 17 存在的情况下,在粪肠球菌和屎肠球菌分离株中观察到 ATP 产量显着减少。
更新日期:2020-03-17
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