Three New Steroids from the Roots of Marsdenia tenacissima

Chem Biodivers. 2024 Dec;21(12):e202401801. doi: 10.1002/cbdv.202401801. Epub 2024 Oct 26.

Abstract

Three undescribed pregnane steroids, 12β-O-4-hydroxybenzoyl tenacigenin D (1), 12β-O-4-hydroxybenzoyl tenacigenin A (2), and 11α-nicotinoyl-17β-marsdenin (3), along with two known analogues (4 and 5), were isolated from the roots of Marsdenia tenacissima. Their structures were elucidated using one- and two-dimensional NMR, high-resolution electron ionization-mass spectrometry, single-crystal X-ray diffraction data, and experimental and density-functional-theory-calculated electronic circular dichroism measurements. All isolated compounds were evaluated for their cytotoxic activities against human lung cancer cells (A549), ovarian carcinoma cells (SKOV-3), gastric cancer cells (MGC 803) and breast cancer cells (MCF-7). Notably, 3 exhibited significant cytotoxic activity against both A549 (median inhibitory concentration (IC50)=16.79 μM) and SKOV-3 (IC50=12.30 μM) cells while exhibiting moderate cytotoxicity on MGC803 and MCF-7 cells.

Keywords: C21 steroids; Cytotoxic activities; Marsdenia tenacissima.

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
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor*
  • Humans
  • Marsdenia* / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Plant Roots* / chemistry
  • Steroids / chemistry
  • Steroids / isolation & purification
  • Steroids / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Steroids