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Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros
Journal of Natural Products ( IF 5.1 ) Pub Date : 2017-08-25 00:00:00 , DOI: 10.1021/acs.jnatprod.7b00543
Giuseppina Chianese 1 , Johanna Silber 1 , Paolo Luciano 2 , Christian Merten 3 , Dirk Erpenbeck 4 , Bülent Topaloglu 5 , Marcel Kaiser 6, 7 , Deniz Tasdemir 1
Affiliation  

Chemical investigation of the marine sponge Ircinia oros yielded four linear furanosesterterpenoids, including the known metabolites ircinin-1 (1) and ircinin-2 (2) and two new compounds, ircinialactam E (3) and ircinialactam F (4). Their chemical structures were elucidated by using a combination of [α]D, NMR, HRMS, and FT-IR spectroscopy. The absolute configuration of C-18 in compounds 13 was identified as R by electronic circular dichroism (ECD) spectroscopy coupled with time-dependent density functional theory calculations. Compounds 14 showed moderate leishmanicidal, trypanocidal, and antiplasmodial activities (IC50 values 28–130 μM). This is the second report of rare glycinyl lactam derivatives 3 and 4 from the genus Ircinia.

中文翻译:

海洋海绵Ircinia oros的抗原生动物线性呋喃酯类萜

海洋海绵Ircinia oros的化学研究产生了四种线性呋喃酯类萜,包括已知的代谢产物ircinin-1(1)和ircinin-2(2)以及两种新化合物ircinialactam E(3)和ircinialactam F(4)。通过结合使用[α] D,NMR,HRMS和FT-IR光谱阐明了它们的化学结构。化合物C-18的绝对构型1 - 3被鉴定为[R由电子圆二色性(ECD)光谱加上时间依赖密度泛函理论计算。化合物1 - 4表现出中等程度的杀菌作用,锥虫杀菌作用和抗疟原虫作用(IC 50值为28–130μM)。这是来自Ircinia属的罕见的甘氨酰内酰胺衍生物34的第二次报告。
更新日期:2017-08-25
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