Euphonoids A-G, cytotoxic diterpenoids from Euphorbia fischeriana

Phytochemistry. 2019 Oct:166:112064. doi: 10.1016/j.phytochem.2019.112064. Epub 2019 Jul 17.

Abstract

Seven previously undescribed polycyclic diterpenoids, euphonoids A-G, including four ent-abietanes, two ent-atisanes, and one ent-kaurene, along with 26 known analogues were isolated from the roots of Euphorbia fischeriana. The structures of the undescribed compounds were elucidated by spectroscopic analysis, ECD calculations, and single crystal X-ray diffraction. Besides, the structure of a previously reported ent-abietane diterpenoid, fischeriabietane A, was revised. All the isolates were screened for the cytotoxicities against five cancer cell lines. Euphonoid A, fischeriabietane A, 11-oxo-ebracteolatanolide B, caudicifolin, jolkinolide B, and methyl-8,11-3-dihydroxy-12-oxo-ent-abietadi-13,15(17)-ene-16-oate showed significant inhibitory activities against human prostate cancer C4-2B and C4-2B/ENZR cell lines, with IC50 values being less than 10 μM. The brief structure-activity relationships (SARs) of these diterpenoids were also discussed.

Keywords: Cytotoxicity; Diterpenoids; Ent-abietanes; Euphorbia fischeriana (Euphorbiaceae).

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology*
  • Euphorbia / chemistry*
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes