Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.

被引：17

作者：

An, Joon Soo ^{[1
]}

Kim, Myoun-Su ^{[1
]}

Han, Jaeho ^{[1
]}

Jang, Sung Chul ^{[1
]}

Im, Ji Hyeon ^{[1
]}

Cui, Jinsheng ^{[1
]}

Lee, Yeonjin ^{[1
]}

Nam, Sang-Jip ^{[2
]}

Shin, Jongheon ^{[1
]}

Lee, Sang Kook ^{[1
]}

Yoon, Yeo Joon ^{[1
]}

Oh, Dong-Chan ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Nat Prod Res Inst, Seoul 08826, South Korea

[2] Ewha Womans Univ, Dept Chem & Nanosci, Seoul 03760, South Korea

来源：

JOURNAL OF NATURAL PRODUCTS | 2022年 / 85卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

CYCLIC-PEPTIDES; BIOSYNTHESIS; SKYLLAMYCIN; DOMAIN; CYCLODEPSIPEPTIDE; STEREOCHEMISTRY; ACTINOBACTERIA; CONFIGURATION; ANTIBIOTICS; DIVERSITY;

D O I：

10.1021/acs.jnatprod.1c00837

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A new nonribosomal peptide, nyuzenamide C (1), was discovered from riverine sediment-derived Streptomyces sp. DM14. Comprehensive analysis of the spectroscopic data of nyuzenamide C (1) revealed that 1 has a bicyclic backbone composed of six common amino acid residues (Asn, Leu, Pro, Gly, Val, and Thr) and four nonproteinogenic amino acid units, including hydroxyglycine, beta-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,beta-dihydroxytyrosine, along with 1,2-epoxypropyl cinnamic acid. The absolute configuration of 1 was proposed by J-based configuration analysis, the advanced Marfey's method, quantum mechanics-based DP4 calculations, and bioinformatic analysis of its nonribosomal peptide synthetase biosynthetic gene cluster. Nyuzenamide C (1) displayed antiangiogenic activity in human umbilical vein endothelial cells and induced quinone reductase in murine Hepa-1c1c7 cells.

引用

页码：804 / 814

页数：11

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