Compounds from the Chinese black ant (Polyrhachis dives) and NMR behavior of the isomers with formamide group

J Asian Nat Prod Res. 2015;17(1):20-6. doi: 10.1080/10286020.2014.966698. Epub 2014 Oct 31.

Abstract

Two new dopamine derivatives divesamides A (1) and B (2), along with six known N-containing compounds were isolated from the Chinese black ant (Polyrhachis dives). Their structures were determined on the basis of spectroscopic methods. Compound 1 is a racemate, and chiral HPLC separation yielded a pair of antipodes. The absolute configuration of (+)-1 was assigned by a computational method. The double signals in the (1)H and (13)C NMR spectra of 2 that resulted from the presence of a formamide group were discussed. The T- and B-lymphocytes proliferation assay showed that 2 has moderate immunosuppressive activity toward T- and B-lymphocytes proliferation at a concentration of 20 μM.

Keywords: N-containing compound; Polyrhachis dives; amide bond; black ant; immunosuppressive activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ants / chemistry*
  • B-Lymphocytes / drug effects
  • China
  • Chromatography, High Pressure Liquid
  • Dopamine / analogs & derivatives*
  • Dopamine / chemistry
  • Dopamine / isolation & purification*
  • Dopamine / pharmacology
  • Formamides / chemistry
  • Formamides / pharmacology
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / isolation & purification*
  • Immunosuppressive Agents / pharmacology*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Stereoisomerism
  • Structure-Activity Relationship
  • T-Lymphocytes / drug effects

Substances

  • Formamides
  • Immunosuppressive Agents
  • divesamide A
  • divesamide B
  • formamide
  • Dopamine