Taraxerol 4-Methoxybenzoate, an in vitro Inhibitor of Photosynthesis Isolated from Pavonia multiflora A. St-Hil. (Malvaceae)

Chem Biodivers. 2016 Mar;13(3):284-292. doi: 10.1002/cbdv.201500049.

Abstract

A phytochemical study of Pavonia multiflora A. St-Hil. (Malvaceae) led to the isolation through chromatographic techniques of 10 secondary metabolites: vanillic acid (1), ferulic acid (2), p-hydroxybenzoic acid (3), p-coumaric acid (4), loliolide (5), vomifoliol (6), 4,5-dihydroblumenol A (7), 3-oxo-α-ionol (9), blumenol C (10), and taraxerol 4-methoxybenzoate (8), the latter being a novel metabolite. Their structures were identified by (1) H- and (13) C-NMR, using one- and two-dimensional techniques, and X-ray crystallography. In this work, we report the effect of compounds 5 and 8 on several photosynthetic activities in an attempt to search for new compounds as potential herbicide agents that affect photosynthesis. Both compounds inhibited the electron flow from H2 O to methyl viologen; therefore, they act as Hill reaction inhibitors. Using polarographic techniques and studies of the fluorescence of chlorophyll a, the interaction sites of these compounds were located at photosystem II.

Keywords: Norisoprenoids; Pavonia multiflora; Phenolic compounds; Photosynthetic inhibitor; Taraxerol 4-methoxybenzoate.

MeSH terms

  • In Vitro Techniques
  • Malvaceae / chemistry*
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Photosynthesis / drug effects*
  • Photosynthetic Reaction Center Complex Proteins / antagonists & inhibitors*
  • Photosynthetic Reaction Center Complex Proteins / metabolism

Substances

  • Photosynthetic Reaction Center Complex Proteins
  • taraxerol 4-methoxybenzoate
  • Oleanolic Acid