title: Sungsanpin, a lasso peptide from a deep-sea streptomycete.
abstract: 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.
authors.affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University , 1 Gwanak-ro, Gwanak-gu, Seoul, Republic of Korea.
authors.forename: Soohyun
authors.initials: S
authors.lastname: Um
authors.forename: Young-Joo
authors.initials: YJ
authors.lastname: Kim
authors.forename: Hyuknam
authors.initials: H
authors.lastname: Kwon
authors.forename: He
authors.initials: H
authors.lastname: Wen
authors.forename: Seong-Hwan
authors.initials: SH
authors.lastname: Kim
authors.forename: Hak Cheol
authors.initials: HC
authors.lastname: Kwon
authors.forename: Sunghyouk
authors.initials: S
authors.lastname: Park
authors.forename: Jongheon
authors.initials: J
authors.lastname: Shin
authors.forename: Dong-Chan
authors.initials: DC
authors.lastname: Oh
mesh_terms: D000595:Amino Acid Sequence; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D008386:Marine Biology; D019906:Nuclear Magnetic Resonance, Biomolecular; D009792:Oceans and Seas; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D056910:Republic of Korea; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D010455:Peptides; C582935:sungsanpin