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Zoanthamine Alkaloid Derivatives from the Zoantharian Zoanthus vietnamensis with Antimetastatic Activity.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-09-07 , DOI: 10.1021/acs.joc.0c01731 Shu-Rong Chen,Shih-Wei Wang,Jyh-Horng Sheu,Ting-Hsuan Chang,Yuan-Bin Cheng
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-09-07 , DOI: 10.1021/acs.joc.0c01731 Shu-Rong Chen,Shih-Wei Wang,Jyh-Horng Sheu,Ting-Hsuan Chang,Yuan-Bin Cheng
A novel compound zoanone A (1), together with eight new alkaloids, 3β,14α-dihydroxy-28-deoxyzoanthenamine (2), 7α-hydroxy-28-deoxyzoanthenamine (3), 3α-hydroxyzoanthenamine (4), 7β-hydroxyzoanthenamine (5), 28α-methoxyzoanthenamine (6), 28α-methoxykuroshine A (7), 30-hydroxykuroshine A (8), and 3β-hydroxy-11-deketo-kuroshine B (9), was isolated from the zoantharian Zoanthus vietnamensis. Their structures were elucidated by the comprehensive analyses of IR, mass spectrometry, NMR, and UV spectroscopic data. The absolute configuration of 1 was established by single-crystal X-ray crystallographic analysis using Cu Kα radiation. A plausible biosynthetic pathway of 1 was proposed. Antiangiogenic and antilymphangiogenic activities of the isolated metabolites were tested and evaluated. The results showed that all isolated compounds had weak antimetastatic activity.
中文翻译:
来自越南的Zanantian Zoanthus的Zoanthamine生物碱衍生物具有抗转移活性。
新型化合物zoanone A(1)以及8种新生物碱3β,14α-二羟基-28-脱氧zoanthenamine(2),7α-羟基-28-deoxyzoanthenamine(3),3α-羟基zoanthenamine (4),7β-羟基zoantamine (5),28α-methoxyzoanthenamine(6),28α-methoxykuroshine A(7),30-hydroxykuroshine A(8),以及3β-羟基-11- deketo-kuroshine B(9),从分离zoantharian Zoanthus vietnamensis。通过红外,质谱,核磁共振和紫外光谱数据的综合分析阐明了它们的结构。绝对配置1通过使用CuKα辐射的单晶X射线晶体学分析建立了Al2O3。提出了一个合理的生物合成途径1。测试和评估了分离出的代谢产物的抗血管生成和抗淋巴血管生成活性。结果表明,所有分离的化合物均具有弱的抗转移活性。
更新日期:2020-10-02
中文翻译:
来自越南的Zanantian Zoanthus的Zoanthamine生物碱衍生物具有抗转移活性。
新型化合物zoanone A(1)以及8种新生物碱3β,14α-二羟基-28-脱氧zoanthenamine(2),7α-羟基-28-deoxyzoanthenamine(3),3α-羟基zoanthenamine (4),7β-羟基zoantamine (5),28α-methoxyzoanthenamine(6),28α-methoxykuroshine A(7),30-hydroxykuroshine A(8),以及3β-羟基-11- deketo-kuroshine B(9),从分离zoantharian Zoanthus vietnamensis。通过红外,质谱,核磁共振和紫外光谱数据的综合分析阐明了它们的结构。绝对配置1通过使用CuKα辐射的单晶X射线晶体学分析建立了Al2O3。提出了一个合理的生物合成途径1。测试和评估了分离出的代谢产物的抗血管生成和抗淋巴血管生成活性。结果表明,所有分离的化合物均具有弱的抗转移活性。