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.
Copyright © 2010 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ananas / chemistry*
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Bleaching Agents / chemistry
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Bleaching Agents / isolation & purification
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Bleaching Agents / pharmacology
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Carboxylic Acids / chemistry
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Carboxylic Acids / isolation & purification*
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Carboxylic Acids / pharmacology
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Fruit / chemistry
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Molecular Structure
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Monophenol Monooxygenase / antagonists & inhibitors
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Nuclear Magnetic Resonance, Biomolecular
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Pentanoic Acids / chemistry
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Pentanoic Acids / isolation & purification*
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Pentanoic Acids / pharmacology
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Pyrroles / chemistry
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Pyrroles / isolation & purification*
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Pyrroles / pharmacology
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Skin / drug effects
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Sulfur Compounds / chemistry
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Sulfur Compounds / isolation & purification*
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Sulfur Compounds / pharmacology
Substances
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(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid
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(S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid
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6-(3-(1H-pyrrole-2-carbonyloxy)-2-hydroxypropoxy)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid
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Bleaching Agents
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Carboxylic Acids
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Pentanoic Acids
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Pyrroles
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Sulfur Compounds
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Monophenol Monooxygenase