2. Academic Validation
  3. 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

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

  • J Antibiot (Tokyo). 2024 Jan 19. doi: 10.1038/s41429-023-00702-2.
Haeun Kwon 1,  Hee Woon Ann 2,  Sojung Park 1,  Jaeyoung Kwon 3,  Keunwan Park 3,  Seung Mok Ryu 4,  Yuanqiang Guo 5,  Jae-Jin Kim 6,  Joung Han Yim 7,  Il-Chan Kim 7,  Sang Hee Shim 8,  Sullim Lee 9,  Dongho Lee 10
Affiliations

Affiliations

  • 1 Department of Plant Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul, 02841, Republic of Korea.
  • 2 Department of Life Science, Gachon University, Seongnam, 13120, Republic of Korea.
  • 3 Natural Product Informatics Research Center, Korea Institute of Science and Technology (KIST) Gangneung Institute, Gangneung, 25451, Republic of Korea.
  • 4 Herbal Medicine Resources Center, Korea Institute of Oriental Medicine, Naju, 58245, Republic of Korea.
  • 5 State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, 300350, People's Republic of China.
  • 6 Division of Environmental Science and Ecological Engineering, College of Life Sciences and Biotechnology, Korea University, Seoul, 02841, Republic of Korea.
  • 7 Division of Life Sciences, Korea Polar Research Institute, Incheon, 21990, Republic of Korea.
  • 8 Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, 08826, Republic of Korea.
  • 9 Department of Life Science, Gachon University, Seongnam, 13120, Republic of Korea. [email protected].
  • 10 Department of Plant Biotechnology, College of Life Sciences and Biotechnology, Korea University, Seoul, 02841, Republic of Korea. [email protected].
PMID: 38243062 DOI: 10.1038/s41429-023-00702-2
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).

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