Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit

Phytochemistry. 2010 Dec;71(17-18):2046-51. doi: 10.1016/j.phytochem.2010.08.014. Epub 2010 Sep 16.

Abstract

Two sulfur-containing compounds, (S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid (1) and (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid (2), and one 1H-pyrrole-2-carboxylic acid derivative, 6-(3-(1H-pyrrole-2-carbonyloxy)-2-hydroxypropoxy)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid (3), together with eighteen known phenolic compounds, were isolated from the fruits of pineapple. Their structures were elucidated by a combination of spectroscopic analyses. Some of these compounds showed inhibitory activities against tyrosinase. The half maximal inhibitory concentration values of compounds 1, 4, 5, 6, 7 are lower than 1 mM. These compounds may contribute to the well-known anti-browning effect of pineapple juice and be potential skin whitening agents in cosmetic applications.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ananas / chemistry*
  • Bleaching Agents / chemistry
  • Bleaching Agents / isolation & purification
  • Bleaching Agents / pharmacology
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / isolation & purification*
  • Carboxylic Acids / pharmacology
  • Fruit / chemistry
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Nuclear Magnetic Resonance, Biomolecular
  • Pentanoic Acids / chemistry
  • Pentanoic Acids / isolation & purification*
  • Pentanoic Acids / pharmacology
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification*
  • Pyrroles / pharmacology
  • Skin / drug effects
  • Sulfur Compounds / chemistry
  • Sulfur Compounds / isolation & purification*
  • Sulfur Compounds / pharmacology

Substances

  • (S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid
  • (S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid
  • 6-(3-(1H-pyrrole-2-carbonyloxy)-2-hydroxypropoxy)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid
  • Bleaching Agents
  • Carboxylic Acids
  • Pentanoic Acids
  • Pyrroles
  • Sulfur Compounds
  • Monophenol Monooxygenase