Ulleunganilines A–C, Trichostatin Analogues Bearing a Modified Side Chain from Streptomyces sp. 13F051,Journal of Natural Products

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Ulleunganilines A–C, Trichostatin Analogues Bearing a Modified Side Chain from Streptomyces sp. 13F051
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-08-28 , DOI: 10.1021/acs.jnatprod.1c00324
Gwi Ja Hwang _{1,

2} , Mina Jang ₁ , Sangkeun Son ₁ , Byeongsan Lee ₁ , Jun-Pil Jang ₁ , Jung-Sook Lee ₃ , Sung-Kyun Ko ₁ , Young-Soo Hong _{1,

2} , Jong Seog Ahn _{1,

2} , Jae-Hyuk Jang _{1,

2}

Affiliation

Three new trichostatin analogues, ulleunganilines A–C (1–3), and seven known trichostatins (4–10) were isolated from cultures of Streptomyces sp. 13F051. NMR, UV, and MS data indicated that the planar structures of 1–3 consisted of modified side chains in the trichostatic acid moiety. The absolute configuration of the 2,4-dimethyl-branched carbon chains in 1 and 2 was determined by the PGME method, while the amino acid group in 3 was identified by advanced Marfey’s method. Based on the structure of the modified side chains, the origin of 1–3 is proposed. Further experiments indicated that 1 and 3 displayed moderate histone deacetylase inhibitory activity, suggesting that not only the hydroxamate group but also the N,N-dimethyl group were essential for the inhibitory activity.

中文翻译：

Ulleunganilines A-C，带有来自 Streptomyces sp. 的修饰侧链的曲古菌素类似物。13F051

从Streptomyces sp. 的培养物中分离出三种新的曲古抑菌素类似物 ulleunganilines A–C ( 1 – 3 ) 和七种已知的曲古抑菌素 ( 4 – 10 ) 。13F051。NMR，UV，和MS数据表明的平面结构1 - 3在trichostatic酸部分组成改性侧链。的2,4-二甲基-支链的碳链中的绝对构型1和2是由PGME法测定，而在氨基酸基团3，通过先进的Marfey法鉴定。基于修改的侧链的结构，起源1 - 3被提议。进一步的实验表明，1和3显示出中等的组蛋白脱乙酰酶抑制活性，这表明不仅异羟肟酸酯基团而且N , N -二甲基基团对于抑制活性都是必不可少的。

更新日期：2021-09-24

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