Mass spectrometry-guided isolation of thiodiketopiperazines from an EtOAc-extract of Setosphaeria rostrata culture medium and their anti-skin aging effects on TNF-α-induced human dermal fibroblasts

Haeun Kwon, Hee Woon Ann, Sojung Park, Jaeyoung Kwon, Keunwan Park, Seung Mok Ryu, Yuanqiang Guo, Jae Jin Kim, Joung Han Yim, Il Chan Kim, Sang Hee Shim, Sullim Lee, Dongho Lee

Research output: Contribution to journalArticlepeer-review

Abstract

Using mass spectrometry (MS)-guided isolation methods, a new thiodiketopiperazine derivative (1) and exserohilone (2) were isolated from an EtOAc-extract of Setosphaeria rostrata culture medium. The chemical structure of the new compound was elucidated by MS and NMR spectroscopy, and the absolute configurations were established by the quantum mechanical calculations of electronic circular dichroism. All isolated compounds were examined for their effects on reactive oxygen species (ROS) production, matrix metalloproteinase 1 (MMP-1) secretion, and procollagen type I α1 secretion in tumor necrosis factor (TNF)-α-induced human dermal fibroblasts. Compound 1 and exserohilone (2) exhibited the inhibition of TNF-α-induced ROS generation and MMP-1 secretion. Additionally, compound 1 and exserohilone (2) increased the procollagen type I α1 secretion. Compound 1 docked computationally into the active site of MMP-1 (−6.0 kcal/mol).

Original languageEnglish
Pages (from-to)257-263
Number of pages7
JournalJournal of Antibiotics
Volume77
Issue number4
DOIs
Publication statusPublished - 2024 Apr

Bibliographical note

Publisher Copyright:
© The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2024.

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery

Fingerprint

Dive into the research topics of 'Mass spectrometry-guided isolation of thiodiketopiperazines from an EtOAc-extract of Setosphaeria rostrata culture medium and their anti-skin aging effects on TNF-α-induced human dermal fibroblasts'. Together they form a unique fingerprint.

Cite this