TY - JOUR
T1 - Nyuzenamide C, an Antiangiogenic Epoxy Cinnamic Acid-Containing Bicyclic Peptide from a Riverine Streptomyces sp.
AU - An, Joon Soo
AU - Kim, Myoun Su
AU - Han, Jaeho
AU - Jang, Sung Chul
AU - Im, Ji Hyeon
AU - Cui, Jinsheng
AU - Lee, Yeonjin
AU - Nam, Sang Jip
AU - Shin, Jongheon
AU - Lee, Sang Kook
AU - Yoon, Yeo Joon
AU - Oh, Dong Chan
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/4/22
Y1 - 2022/4/22
N2 - 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, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-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.
AB - 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, β-hydroxyphenylalanine, p-hydroxyphenylglycine, and 3,β-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.
UR - http://www.scopus.com/inward/record.url?scp=85127267245&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.1c00837
DO - 10.1021/acs.jnatprod.1c00837
M3 - Review article
C2 - 35294831
AN - SCOPUS:85127267245
SN - 0163-3864
VL - 85
SP - 804
EP - 814
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -