28-Noroleanane-derived spirocyclic triterpenoids and iridoid glucosides from the roots of Phlomoides umbrosa (Turcz.) Kamelin & Makhm with their cytotoxic effects

Phytochemistry. 2018 Sep:153:138-146. doi: 10.1016/j.phytochem.2018.06.003. Epub 2018 Jun 18.

Abstract

Four undescribed 23,24-O-isopropylidene-19(18 → 17)-abeo-28-noroleanane-derived spirocyclic triterpenoids and an undescribed 28-noroleanane-derived spirocyclic triterpenoid, together with five known 28-noroleanane-derived spirocyclic triterpenoids, were isolated and identified. In addition, three undescribed iridoid glucosides and four known ones were also identified. All the isolates were identified using spectroscopic techniques, and the absolute configurations of 28-noroleanane-derived spirocyclic triterpenoids were determined by CD method for the first time. Additionally, the alkaline hydrolysis method and HPLC analysis were applied to confirm the moieties of the iridoid glucosides. The fraction and isolates were evaluated for cytotoxic activity on cervical cancer (Hela), human promyelocytic leukemia (HL-60), and breast cancer (MCF-7) cell lines. Among them, phlomisu E possessed an aldehyde group showed the most potent cytotoxic effect with IC50 value less than 10 μM.

Keywords: Cytotoxicity; Iridoid glucoside; Nortriterpenoid; Phlomoides umbrosa (Turcz.) Kamelin & Makhm (Lamiaceae).

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • HeLa Cells
  • Humans
  • Iridoid Glucosides / chemistry
  • Iridoid Glucosides / isolation & purification
  • Iridoid Glucosides / pharmacology*
  • Lamiaceae / chemistry*
  • MCF-7 Cells
  • Molecular Conformation
  • Plant Roots / chemistry*
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification
  • Spiro Compounds / pharmacology*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Iridoid Glucosides
  • Spiro Compounds
  • Triterpenes