Natural Products Research Institute, College of Pharmacy, Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul, Republic of Korea.
J Nat Prod. 2013 May 24;76(5):873-9. doi: 10.1021/np300902g. Epub 2013 May 10.
Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-) that form a cyclic peptide and seven amino acids (-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.
从韩国济州岛深海沉积物中分离得到的链霉菌属中发现了一种新的 15 个氨基酸的肽，命名为 Sungsanpin（1）。通过 1D 和 2D NMR 光谱、质谱和紫外光谱确定了 1 的平面结构。通过用 Marfey 试剂和 2,3,4,6-四-O-乙酰基-β-d-吡喃葡萄糖基异硫氰酸酯对 1 的水解产物进行衍生化，然后进行 LC-MS 分析，确定了该化合物中立体中心的绝对构型。仔细分析 ROESY NMR 谱和三维结构计算表明，Sungsanpin 具有套索肽的特征：八个氨基酸（-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-）形成一个环状肽，七个氨基酸（-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)-）形成一个环通过环的尾巴。因此，Sungsanpin 是从海洋来源的微生物中分离出的第一个套索肽。Sungsanpin 在人肺癌细胞系 A549 的细胞侵袭试验中表现出抑制活性。
