Sungsanpin, a Lasso Peptide from a Deep-Sea Streptomycete
Sungsanpin, a Lasso Peptide from a Deep-Sea Streptomycete
Soohyun Um †, Young-Joo Kim ‡, Hyuknam Kwon †, He Wen †, Seong-Hwan Kim †, Hak Cheol Kwon ‡, Sunghyouk Park †, Jongheon Shin †, and Dong-Chan Oh *��
J. Nat. Prod., Article ASAP
DOI: 10.1021/np300902g
Publication Date (Web): May 10, 2013
Copyright © 2013 The American Chemical Society and American Society of Pharmacognosy
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 (-Gly1-Phe-Gly-Ser-Lys-Pro-Ile-Asp8-) that form a cyclic peptide and seven amino acids (-Ser9-Phe-Gly-Leu-Ser-Trp-Leu15) 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.
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