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Ulleungdolin, a Polyketide–Peptide Hybrid Bearing a 2,4-Di-O-methyl-β-d-antiarose from Streptomyces sp. 13F051 Co-cultured with Leohumicola minima 15S071
Journal of Natural Products ( IF 5.1 ) Pub Date : 2022-10-05 , DOI: 10.1021/acs.jnatprod.2c00682
Gwi Ja Hwang 1, 2 , Mina Jang 1, 3 , Sangkeun Son 1, 4 , Gil Soo Kim 1, 2 , Byeongsan Lee 1 , Kyung Taek Heo 1, 2 , Geum Jin Kim 5 , Hyukjae Choi 5 , Jae-Seoun Hur 6 , Jun-Pil Jang 1 , Sung-Kyun Ko 1, 2 , Young-Soo Hong 1, 2 , Jong Seog Ahn 1, 2 , Jae-Hyuk Jang 1, 2
Affiliation  

A new secondary metabolite, ulleungdolin (1), was isolated from the co-culture of an actinomycete, Streptomyces sp. 13F051, and a fungus, Leohumicola minima 15S071. Based on the NMR, UV, and MS data, it was deduced that the planar structure of 1 comprised an isoindolinone (IsoID) with an octanoic acid, a tripeptide, and a sugar. The tripeptide has the unprecedented amino acids norcoronamic acid, 3-hydroxy-glutamine, and 4-hydroxy-phenylglycine and is linked by a C–N bond with IsoID. The absolute configurations were determined by chemical derivatization, extensive spectroscopic methods, and electronic circular dichroism calculations and supported by bioinformatic analyses. Bioactivity evaluation studies indicated that 1 had an antimigration effect on MDA-MB-231 breast cancer cells.

中文翻译:

Ulleungdolin,一种聚酮化合物-肽混合体,带有来自 Streptomyces sp. 的 2,4-二-O-甲基-β-d-抗糖。13F051 与 Leohumicola minima 15S071 共培养

一种新的次生代谢物 ulleungdolin ( 1 ) 是从放线菌Streptomyces sp. 的共培养物中分离出来的。13F051 和一种真菌Leohumicola minima 15S071。基于 NMR、UV 和 MS 数据,推断1的平面结构包含异吲哚啉酮 (IsoID) 与辛酸、三肽和糖。三肽具有前所未有的氨基酸去甲冠状酸、3-羟基-谷氨酰胺和 4-羟基-苯基甘氨酸,并通过 C-N 键与 IsoID 连接。绝对构型由化学衍生化、广泛的光谱方法和电子圆二色性计算确定,并得到生物信息学分析的支持。生物活性评价研究表明,1对 MDA-MB-231 乳腺癌细胞具有抗迁移作用。
更新日期:2022-10-05
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