New Solasodine-Type Glycoalkaloids Isolated from Solanum nigrum and Their Cytotoxic Activity

Chem Biodivers. 2024 Jul;21(7):e202400872. doi: 10.1002/cbdv.202400872. Epub 2024 Jun 8.

Abstract

Three undescribed solalodine-type glycoalkaloids, named solanigrinoside A-C (1-3), and six known compounds (4-9) were isolated from the whole plants of Solanum nigrum. Their structures were elucidated based on analysis of HR-ESI-MS, 1D- and 2D-NMR spectral data, and comparison with those reported in literatures. The solanigrinoside A-C (1-3), solasodine (4), and 3-acetoxysolasodine (5) exhibited cytotoxic effects against LU-1, Hep-G2, and MCF-7 cells with IC50 values in range from 4.6 μM to 56.2 μM. Compound 2 showed the significant cytotoxic activity with corresponding IC50 values of 5.7 μM, 7.9 μM, and 4.6 μM, respectively.

Keywords: Cytotoxic activity; Solanaceae; Solanum glycoalkaloid; Solanum nigrum; Solasodine derivative.

MeSH terms

  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor*
  • Humans
  • Molecular Conformation
  • Molecular Structure
  • Solanaceous Alkaloids* / chemistry
  • Solanaceous Alkaloids* / isolation & purification
  • Solanaceous Alkaloids* / pharmacology
  • Solanum nigrum* / chemistry
  • Structure-Activity Relationship

Substances

  • solasodine
  • Solanaceous Alkaloids
  • Antineoplastic Agents, Phytogenic