Rhamnolipids as platform molecules for production of potential anti-zoospore agrochemicals

J Agric Food Chem. 2015 Apr 8;63(13):3367-76. doi: 10.1021/acs.jafc.5b00033. Epub 2015 Mar 26.

Abstract

Rhamnolipid biosurfactants have potential applications in the control of zoosporic plant pathogens. However, rhamnolipids have not been closely investigated for the anti-zoospore mechanism or for developing new anti-zoospore chemicals. In this study, RhL-1 and RhL-3 groups of rhamnolipids were used to generate the corresponding RhL-2 and RhL-4 groups and the free diacids. Conversion of RhL-3 to RhL-1 was also accomplished in vitro with cellobiase as the catalyst. The anti-zoospore effects of RhL-1-RhL-4 and the diacids were investigated with zoospores of Phytophthora sojae. For RhL-1-RhL-4, approximately 20, 30, 40, and 40 mg/L, respectively, were found to be the lowest concentrations required to stop movement of all zoospores, which indicates that the anti-zoospore effect remains strong even after RhL-1 and RhL-3 are hydrolyzed into RhL-2 and RhL-4. The free diacids required a significantly higher critical concentration of about 125 mg/L. Rhamnose can be obtained as a co-product.

Keywords: HPLC−MS; biosurfactant; fungi; rhamnolipid; zoospore.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Agrochemicals / chemical synthesis*
  • Fungicides, Industrial / chemical synthesis*
  • Fungicides, Industrial / pharmacology*
  • Glycolipids / chemistry*
  • Glycolipids / pharmacology
  • Hydrolysis
  • Nucleotides, Cyclic
  • Phytophthora
  • Spores, Fungal / drug effects*

Substances

  • Agrochemicals
  • Fungicides, Industrial
  • Glycolipids
  • Nucleotides, Cyclic
  • rhamnolipid
  • zoospore maintenance factor, blastocladiella