Retinoylserine and retinoylalanine, natural products of the moth Trichoplusia ni

J Nat Prod. 2005 Oct;68(10):1536-40. doi: 10.1021/np0496791.

Abstract

Insect cells convert vitamin A into a number of retinoids that are evolutionarily conserved with those of mammalian cells. However, insect cells also produce additional natural retinoids. Namely, two retinoic acid peptides, N-trans-retinoylserine (1) and N-trans-retinoylalanine (2), have been isolated from a cell line of the common cabbage looper, Trichoplusia ni. These are the first examples of naturally occurring retinoic acid linked to amino acids through an amide bond; the amino acid moieties are depicted in the more common l-configuration, although the absolute configuration was not determined due to the minuscule sample amount.

Publication types

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

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Alanine / isolation & purification
  • Animals
  • Chromatography
  • Molecular Structure
  • Moths / chemistry*
  • Serine / analogs & derivatives*
  • Serine / chemical synthesis
  • Serine / chemistry
  • Serine / isolation & purification
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • Tretinoin / analogs & derivatives*
  • Tretinoin / chemical synthesis
  • Tretinoin / chemistry
  • Tretinoin / isolation & purification

Substances

  • retinoylalanine
  • retinoylserine
  • Serine
  • Tretinoin
  • Alanine