Ulleungdolin, a Polyketide–Peptide Hybrid Bearing a 2,4-Di-<i>O</i>-methyl-β-<scp>d</scp>-antiarose from <i>Streptomyces</i> sp. 13F051 Co-cultured with <i>Leohumicola minima</i> 15S071
Gwi Ja Hwang, Mina Jang, Sangkeun Son, Gil Soo Kim, Byeongsan Lee, Kyung Taek Heo, Geum Jin Kim, Hyukjae Choi, Jae–Seoun Hur, Jun‐Pil Jang, Jun‐Pil Jang, Sung‐Kyun Ko, Young‐Soo Hong, Jong Seog Ahn, Jae‐Hyuk Jang, Jae‐Hyuk Jang
Abstract
A new secondary metabolite, ulleungdolin (1), was isolated from the co-culture of an actinomycete, Streptomyces sp. 13F051, and a fungus, Leohumicola minima 15S071. Based on the NMR, UV, and MS data, it was deduced that the planar structure of 1 comprised an isoindolinone (IsoID) with an octanoic acid, a tripeptide, and a sugar. The tripeptide has the unprecedented amino acids norcoronamic acid, 3-hydroxy-glutamine, and 4-hydroxy-phenylglycine and is linked by a C–N bond with IsoID. The absolute configurations were determined by chemical derivatization, extensive spectroscopic methods, and electronic circular dichroism calculations and supported by bioinformatic analyses. Bioactivity evaluation studies indicated that 1 had an antimigration effect on MDA-MB-231 breast cancer cells.