Molecular networking-guided isolation of melanogenesis inhibitory dihydro-β-agarofuran sesquiterpenoids from Celastrus orbiculatus

Phytochemistry. 2025 Jan:229:114312. doi: 10.1016/j.phytochem.2024.114312. Epub 2024 Oct 22.

Abstract

Seven previously undescribed dihydro-β-agarofurans (1-7) together with 28 known compounds were isolated from Celastrus orbiculatus fruits using LC-MS/MS-based molecular networking-guided purification. Their structures were elucidated through 1D and 2D-NMR, HRESIMS analysis, and ECD quantum chemical calculations. The inhibitory effects of all isolated compounds on α-MSH-induced melanin production in B16F0 melanoma cells were tested. Compounds 1, 11, 12, 19-21, 23, 29, 31, 34, and 35 showed significant inhibitory effects on melanin production with IC50 values ranging from 11.3 to 30.1 μM.

Keywords: Celastraceae; Celastrus orbiculatus; Dihydro-β-agarofuran; GNPS; Melanin production; Molecular networking.

MeSH terms

  • Animals
  • Celastrus* / chemistry
  • Cell Line, Tumor
  • Dose-Response Relationship, Drug
  • Fruit / chemistry
  • Melanins* / antagonists & inhibitors
  • Melanins* / biosynthesis
  • Melanogenesis
  • Melanoma, Experimental / drug therapy
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Structure
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification
  • Sesquiterpenes* / pharmacology
  • Structure-Activity Relationship

Substances

  • Melanins
  • Sesquiterpenes
  • dihydroagarofuran