Anti-inflammatory and antiproliferative diterpenoids from Plectranthus scutellarioides

Phytochemistry. 2018 Oct:154:39-46. doi: 10.1016/j.phytochem.2018.06.012. Epub 2018 Jun 28.

Abstract

Chemical investigation of the dichloromethane extract of the aerial parts of Plectranthus scutellarioides led to the isolation and characterization of 10 diterpenoids with an abietane skeleton and one cembrane-type diterpenoid. Among them, six have not yet been described in the literature. Their structures were established by 1D and 2D NMR, UV and IR spectroscopy, and HRESIMS. The relative configuration was determined by Gauge-Independent Atomic Orbital NMR chemical shift calculations supported by the advanced statistical method DP4 plus and further confirmed by electronic circular dichroism. The isolated constituents were evaluated for their in vitro NF-κB inhibitory activity, as well as for their cytotoxic effects in human multiple myeloma cancer stem cells and RPMI 8226 tumor cell line. Coleon O, coleon G, lanugone K and 6-acetylfredericone B showed the highest inhibitory effect against NF-κB, displaying IC50 of 11.2, 11.0, 4.5 and 9.7 μM, respectively. Coleon O exhibited also a significant activity towards human multiple myeloma cancer stem cells and RPMI 8226 cells with IC50 of 9.2 and 8.4 μM, respectively.

Keywords: Abietane diterpene; Cembrane diterpene; Lamiaceae; MM-CSCs antiproliferative activity; NF-κB inhibitory activity; Plectranthus scutellarioides.

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification
  • Abietanes / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HEK293 Cells
  • Humans
  • Molecular Conformation
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / metabolism
  • Plant Components, Aerial / chemistry
  • Plectranthus / chemistry*
  • Structure-Activity Relationship

Substances

  • Abietanes
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents, Phytogenic
  • NF-kappa B