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Article: Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit
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TitleSulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit
 
AuthorsZheng, ZP2
Ma, J2
Cheng, KW2
Chao, J2 1
Zhu, Q2
Chang, RCC1 1
Zhao, M3
Lin, ZX3
Wang, M2
 
Keywords1H-pyrrole-2- carboxylic acid derivative
Ananas comosus
Poales
Sulfur-containing constituents
Tyrosinase inhibitors
 
Issue Date2010
 
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/phytochem
 
CitationPhytochemistry, 2010, v. 71 n. 17-18, p. 2046-2051 [How to Cite?]
DOI: http://dx.doi.org/10.1016/j.phytochem.2010.08.014
 
AbstractTwo 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. © 2010 Elsevier Ltd. All rights reserved.
 
ISSN0031-9422
2012 Impact Factor: 3.05
2012 SCImago Journal Rankings: 1.003
 
DOIhttp://dx.doi.org/10.1016/j.phytochem.2010.08.014
 
ISI Accession Number IDWOS:000285325500012
Funding AgencyGrant Number
Innovation and Technology Fund of Hong KongITS/065/07
Funding Information:

The project was supported by Innovation and Technology Fund of Hong Kong (ITS/065/07)

 
ReferencesReferences in Scopus
 
GrantsNatural tyrosinase inhibitors as skin whitening agents
 
DC FieldValue
dc.contributor.authorZheng, ZP
 
dc.contributor.authorMa, J
 
dc.contributor.authorCheng, KW
 
dc.contributor.authorChao, J
 
dc.contributor.authorZhu, Q
 
dc.contributor.authorChang, RCC
 
dc.contributor.authorZhao, M
 
dc.contributor.authorLin, ZX
 
dc.contributor.authorWang, M
 
dc.date.accessioned2011-07-27T02:05:34Z
 
dc.date.available2011-07-27T02:05:34Z
 
dc.date.issued2010
 
dc.description.abstractTwo 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. © 2010 Elsevier Ltd. All rights reserved.
 
dc.description.natureLink_to_subscribed_fulltext
 
dc.identifier.citationPhytochemistry, 2010, v. 71 n. 17-18, p. 2046-2051 [How to Cite?]
DOI: http://dx.doi.org/10.1016/j.phytochem.2010.08.014
 
dc.identifier.citeulike7883048
 
dc.identifier.doihttp://dx.doi.org/10.1016/j.phytochem.2010.08.014
 
dc.identifier.epage2051
 
dc.identifier.hkuros186776
 
dc.identifier.isiWOS:000285325500012
Funding AgencyGrant Number
Innovation and Technology Fund of Hong KongITS/065/07
Funding Information:

The project was supported by Innovation and Technology Fund of Hong Kong (ITS/065/07)

 
dc.identifier.issn0031-9422
2012 Impact Factor: 3.05
2012 SCImago Journal Rankings: 1.003
 
dc.identifier.issue17-18
 
dc.identifier.openurl
 
dc.identifier.pmid20843530
 
dc.identifier.scopuseid_2-s2.0-78249262932
 
dc.identifier.spage2046
 
dc.identifier.urihttp://hdl.handle.net/10722/136239
 
dc.identifier.volume71
 
dc.languageeng
 
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/phytochem
 
dc.publisher.placeUnited Kingdom
 
dc.relation.ispartofPhytochemistry
 
dc.relation.projectNatural tyrosinase inhibitors as skin whitening agents
 
dc.relation.referencesReferences in Scopus
 
dc.subject.meshAnanas - chemistry
 
dc.subject.meshCarboxylic Acids - chemistry - isolation and purification - pharmacology
 
dc.subject.meshPentanoic Acids - chemistry - isolation and purification - pharmacology
 
dc.subject.meshPyrroles - chemistry - isolation and purification - pharmacology
 
dc.subject.meshSulfur Compounds - chemistry - isolation and purification - pharmacology
 
dc.subject1H-pyrrole-2- carboxylic acid derivative
 
dc.subjectAnanas comosus
 
dc.subjectPoales
 
dc.subjectSulfur-containing constituents
 
dc.subjectTyrosinase inhibitors
 
dc.titleSulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit
 
dc.typeArticle
 
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Author Affiliations
  1. The University of Hong Kong Li Ka Shing Faculty of Medicine
  2. The University of Hong Kong
  3. Chinese University of Hong Kong