(±)-Aspongamide A, an N-acetyldopamine trimer isolated from the insect Aspongopus chinensis, is an inhibitor of p-Smad3

Org Lett. 2014 Jan 17;16(2):532-5. doi: 10.1021/ol403409v. Epub 2014 Jan 2.

Abstract

(±)-Aspongamide A (1), an unusual trimer of N-acetyldopamine (NADA) bearing a novel tetrahydrobenzo[a]dibenzo[b,e][1,4]dioxine structure, and a pair of NADA dimeric enantiomers (2) were isolated from Aspongopus chinensis. The structures of compounds 1 and 2 were assigned using spectroscopic methods. Compound 1 was found to be an inhibitor of Smad3 phosphorylation in transforming growth factor-β1 (TGF-β1) induced rat renal proximal tubular cells and suppressed extracellular matrix expression in mesangial cells under diabetic conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dopamine / analogs & derivatives*
  • Dopamine / chemistry
  • Dopamine / isolation & purification
  • Dopamine / pharmacology
  • Hemiptera / chemistry*
  • Mesangial Cells / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phosphorylation
  • RNA, Messenger / metabolism
  • Rats
  • Signal Transduction
  • Smad3 Protein / antagonists & inhibitors*
  • Transforming Growth Factor beta1 / metabolism

Substances

  • RNA, Messenger
  • Smad3 Protein
  • Transforming Growth Factor beta1
  • aspongamide A
  • N-acetyldopamine
  • Dopamine