Rhizoleucinoside, a Rhamnolipid-Amino Alcohol Hybrid from the Rhizobial Symbiont Bradyrhizobium sp. BTAi1

Org Lett. 2016 Mar 18;18(6):1490-3. doi: 10.1021/acs.orglett.6b00461. Epub 2016 Mar 9.

Abstract

Rhizoleucinoside (1), a unique rhamnolipid-amino alcohol hybrid, was isolated from the rhizobial symbiont bacterium Bradyrhizobium sp. BTAi1. Compound 1 features a rare rhamnolipid core attached to an unprecedented leucinol moiety. Its structure and absolute configuration were determined by spectroscopic analysis, tandem mass spectrometry, chemical degradation, and application of the Marfey's method. Compound 1 possesses moderate cytotoxicity to BV-2 murine microglia and highly aggressive proliferating immortalized (HAPI) rat microglia cells.

Publication types

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

MeSH terms

  • Animals
  • Bradyrhizobium / chemistry*
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification*
  • Leucine / analogs & derivatives*
  • Leucine / chemistry
  • Leucine / isolation & purification*
  • Mice
  • Microglia / chemistry
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Rats

Substances

  • Cytotoxins
  • Glycolipids
  • rhizoleucinoside
  • Leucine