Neo-5,10-seco-clerodane diterpenoids from Schnabelia terniflora

Fitoterapia. 2024 Oct:178:106190. doi: 10.1016/j.fitote.2024.106190. Epub 2024 Aug 15.

Abstract

Three new neo-5,10-seco-clerodane diterpenoids (1-3), four previously undescribed ethoxy/methoxy acetal analogues (4-7), one new etherified labdane diterpenoid (8), and seven known diterpenoids (9-15) were isolated from the whole plant of Schnabelia terniflora. Their structures were established on the basis of extensive spectroscopic analysis, single-crystal X-ray diffraction data, calculated electronic circular dichroism (ECD), and Mo2(OAc)4-induced circular dichroism. Compounds 2 and 3 represent the first examples of neo-5,10-seco-clerodane diterpenoids containing a 1H-pyrrole-2,5-dione and a pyrrolidine-2,5-dione moiety, respectively. A plausible biosynthetic pathway for 1-3 is proposed. All diterpenoids were evaluated for their cytotoxic activity against non-small-cell lung cancer lines (A549 and H460) and gastric cancer lines (HGC27 and AGS). Among them, 2 and 14 showed moderate cytotoxicity against four cell lines.

Keywords: Biosynthetic pathway; Cytotoxic activity; Lamiaceae; Neo-5,10-seco-clerodane; Schnabelia terniflora.

MeSH terms

  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Cell Line, Tumor
  • China
  • Diterpenes, Clerodane* / chemistry
  • Diterpenes, Clerodane* / isolation & purification
  • Diterpenes, Clerodane* / pharmacology
  • Humans
  • Molecular Structure
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology

Substances

  • Diterpenes, Clerodane
  • Antineoplastic Agents, Phytogenic
  • Phytochemicals