Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas bussei

J Nat Prod. 2016 Sep 23;79(9):2181-7. doi: 10.1021/acs.jnatprod.6b00178. Epub 2016 Aug 12.

Abstract

The phytochemical investigation of the CH2Cl2/MeOH (1:1) extract of the roots of Pentas parvifolia led to the isolation of three new naphthalenes, parvinaphthols A (1), B (2), and C (3), two known anthraquinones, and five known naphthalene derivatives. Similar investigation of the roots of Pentas bussei afforded a new polycyclic naphthalene, busseihydroquinone E (4), a new 2,2'-binaphthralenyl-1,1'-dione, busseihydroquinone F (5), and five known naphthalenes. All purified metabolites were characterized by NMR and MS data analyses, whereas the absolute configurations of 3 and 4 were determined by single-crystal X-ray diffraction studies. The E-geometry of compound 5 was supported by DFT-based chemical shift calculations. Compounds 2-4 showed marginal cytotoxicity against the MDA-MB-231 human triple-negative breast cancer cell line with IC50 values ranging from 62.3 to 129.6 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Antimalarials / chemistry
  • Crystallography, X-Ray
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plasmodium falciparum / drug effects
  • Rubiaceae / chemistry*

Substances

  • Anthraquinones
  • Antimalarials
  • Naphthalenes
  • parvinaphthol A
  • parvinaphthol B
  • parvinaphthol C