2-Phenylnaphthalenes and a polyoxygenated cyclohexene from the stem and root extracts of Uvaria cherrevensis (Annonaceae)

Fitoterapia. 2017 Jul:120:103-107. doi: 10.1016/j.fitote.2017.06.002. Epub 2017 Jun 9.

Abstract

Three new 2-phenylnaphthalene derivatives, cherrevenaphthalenes A-C (1-3), and a new polyoxygenated cyclohexene derivative, (-)-uvaribonol F (4) together with six known compounds, 5-10, were isolated from the stem and root extracts of Uvaria cherrevensis (Annonaceae). The structures of all isolated compounds were elucidated by spectroscopic analysis. The structures of 3 and 4 were further confirmed by single crystal X-ray diffraction methods. Compound 2 exhibited modest antiplasmodial activity against the P. falciparum stains TM4/8.2 and K1CB1 with IC50 values of 18.8±3.63 and 23.4±4.08μM, respectively, and weak cytotoxicity to a Vero cell line. Furthermore, compound 4 displayed cytotoxic activity against a KB cell line with an IC50 value of 22.1±0.42μM but was non-cytotoxic to the Vero cell line. Compound 5 revealed stronger cytotoxicity towards the KB cell line, with an IC50 value of 5.05±0.86μM and was nearly equally cytotoxic to the Vero cell line.

Keywords: Annonaceae; Antiplasmodial activity; Cytotoxic activity; Phenylnaphthalene; Polyoxygenated cyclohexene; Uvaria cherrevensis.

MeSH terms

  • Animals
  • Antimalarials / isolation & purification
  • Antimalarials / pharmacology*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Chlorocebus aethiops
  • Cyclohexenes / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Naphthalenes / isolation & purification
  • Naphthalenes / pharmacology*
  • Plant Roots / chemistry
  • Plant Stems / chemistry
  • Uvaria / chemistry*
  • Vero Cells
  • X-Ray Diffraction

Substances

  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Cyclohexenes
  • Naphthalenes