Phenolic constituents from the roots of Mikania micrantha and their allelopathic effects

J Agric Food Chem. 2013 Jul 31;61(30):7309-14. doi: 10.1021/jf4017652. Epub 2013 Jul 16.

Abstract

Four new thymol derivatives, 8,10-dihydroxy-9-benzoyloxythymol (1), 9-isobutyryloxy-10-hydroxythymol (2), 7,8,9,10-tetrahydroxythymol (3), and 7,8,10-trihydroxy-9-E-feruloyloxythymol (4), were isolated from the fresh roots of Mikania micrantha , along with 8,9,10-trihydroxythymol (5), 8,10-dihydroxy-9-acetoxythymol (6), 8,10-dihydroxy-9-isobutyryloxythymol (7), 8,10-dihydroxy-9-(2-methylbutyryloxy)thymol (8), 8,9-dehydro-10-hydroxythymol (9), 8-methoxy-9-hydroxythymol (10), ethyl caffeate (11), ethyl ferulate (12), 3,5-di-O-caffeoylquinic acid (13), and mikanin (14). Their structures were determined by spectroscopic methods. The known thymol derivatives (5-10) were obtained from the genus Mikania for the first time. Allelopathic effects of these compounds on Arabidopsis thaliana seeds were evaluated by a filter paper assay. After the treatment at 0.1 mM for 4 days, the seed germination rate with compound 8 was 48% and the inhibitory rates of shoot growth with compounds 1, 2, 7-10, and 12 were over 40%. The IC50 values of compounds 1 and 8 on shoot growth were 342.5 and 625 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allelopathy / drug effects*
  • Arabidopsis / drug effects
  • Arabidopsis / growth & development
  • Germination / drug effects
  • Mikania / chemistry*
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Roots / chemistry
  • Seeds / drug effects
  • Seeds / growth & development

Substances

  • Phenols
  • Plant Extracts