Pentaminomycins A and B, Hydroxyarginine-Containing Cyclic Pentapeptides from Streptomyces sp RK88-1441
Pentaminomycins A and B, Hydroxyarginine-Containing Cyclic Pentapeptides from Streptomyces sp RK88-1441
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DOI：
10.1021/acs.jnatprod.7b00882
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发表时间：
2018-04-01
影响因子：
5.1
通讯作者：
Ahn, Jong Seog
中科院分区：
文献类型：
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作者：
Jang, Jun-Pil;Hwang, Gwi Ja;Ahn, Jong Seog
从链霉菌RK 88 -1441的培养物中分离到两个新的环肽，即五氨基霉素A（1）和B（2）。基于NMR、UV、IR和MS数据的解释，1和2的平面结构被阐明为具有修饰的氨基酸残基N-5-羟基精氨酸（N5-OH-Arg）的环状五肽。氨基酸残基的绝对构型由改进的马氏法确定。通过对从部分水解产物中获得的片段肽进行手性分析，确定序列中L-和D-氨基酸的位置;通过LC-MS鉴定氨基酸。五氨基霉素A（1）通过抑制黑素生成酶（包括酪氨酸酶、酪氨酸酶相关蛋白-1（TRP-1）和酪氨酸酶相关蛋白-2（TRP-2）的表达，减少α-MSH刺激的黑色素合成。
Two new cyclic peptides, pentaminomycins A (1) and B (2), were isolated from cultures of Streptomyces sp. RK88-1441. Based on the interpretation of the NMR, UV, IR, and MS data, the planar structures of 1 and 2 were elucidated as cyclic pentapeptides with a modified amino acid residue, N-5-hydroxyarginine (N5-OH-Arg). The absolute configurations of the constituent amino acid residues were determined by the advanced Marfey's method. Localization of L- and D-amino acids in the sequence was ascertained by chiral analysis of the fragment peptide obtained from a partial hydrolysate; amino acids were identified by LC-MS. Pentaminomycin A (1) reduced alpha-MSH-stimulated melanin synthesis by suppressing the expression of melanogenic enzymes including tyrosinase, tyrosinase-related protein-1 (TRP-1), and tyrosinase-related protein-2 (TRP-2).