Ulleunganilines A-C, Trichostatin Analogues Bearing a Modified Side Chain from Streptomyces sp. 13F051

  • J Nat Prod. 2021 Sep 24;84(9):2420-2426. doi: 10.1021/acs.jnatprod.1c00324.
Gwi Ja Hwang  1  2 ,  Mina Jang  1 ,  Sangkeun Son  1 ,  Byeongsan Lee  1 ,  Jun-Pil Jang  1 ,  Jung-Sook Lee  3 ,  Sung-Kyun Ko  1 ,  Young-Soo Hong  1  2 ,  Jong Seog Ahn  1  2 ,  Jae-Hyuk Jang  1  2
Affiliations
  • 1. Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Cheongju 28116, South Korea.
  • 2. Department of Biomolecular Science, KRIBB School of Bioscience, University of Science and Technology (UST), Daejeon 34141, South Korea.
  • 3. Korean Collection for Type Cultures (KCTC), Biological Resource Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 56212, South Korea.
PMID: 34455777 DOI: 10.1021/acs.jnatprod.1c00324
Abstract

Three new trichostatin analogues, ulleunganilines A-C (1-3), and seven known trichostatins (4-10) were isolated from cultures of Streptomyces sp. 13F051. NMR, UV, and MS data indicated that the planar structures of 1-3 consisted of modified side chains in the trichostatic acid moiety. The absolute configuration of the 2,4-dimethyl-branched carbon chains in 1 and 2 was determined by the PGME method, while the amino acid group in 3 was identified by advanced Marfey's method. Based on the structure of the modified side chains, the origin of 1-3 is proposed. Further experiments indicated that 1 and 3 displayed moderate histone deacetylase inhibitory activity, suggesting that not only the hydroxamate group but also the N,N-dimethyl group were essential for the inhibitory activity.