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

TitleSulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit
Authors
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
Citation
Phytochemistry, 2010, v. 71 n. 17-18, p. 2046-2051 How to Cite?
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. © 2010 Elsevier Ltd. All rights reserved.
Persistent Identifierhttp://hdl.handle.net/10722/136239
ISSN
2013 Impact Factor: 3.350
2013 SCImago Journal Rankings: 1.076
ISI Accession Number ID
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)

References
Grants

 

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
DC FieldValueLanguage
dc.contributor.authorZheng, ZPen_HK
dc.contributor.authorMa, Jen_HK
dc.contributor.authorCheng, KWen_HK
dc.contributor.authorChao, Jen_HK
dc.contributor.authorZhu, Qen_HK
dc.contributor.authorChang, RCCen_HK
dc.contributor.authorZhao, Men_HK
dc.contributor.authorLin, ZXen_HK
dc.contributor.authorWang, Men_HK
dc.date.accessioned2011-07-27T02:05:34Z-
dc.date.available2011-07-27T02:05:34Z-
dc.date.issued2010en_HK
dc.identifier.citationPhytochemistry, 2010, v. 71 n. 17-18, p. 2046-2051en_HK
dc.identifier.issn0031-9422en_HK
dc.identifier.urihttp://hdl.handle.net/10722/136239-
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.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/phytochemen_HK
dc.relation.ispartofPhytochemistryen_HK
dc.subject1H-pyrrole-2- carboxylic acid derivativeen_HK
dc.subjectAnanas comosusen_HK
dc.subjectPoalesen_HK
dc.subjectSulfur-containing constituentsen_HK
dc.subjectTyrosinase inhibitorsen_HK
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.titleSulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruiten_HK
dc.typeArticleen_HK
dc.identifier.openurlhttp://library.hku.hk:4550/resserv?sid=HKU:IR&issn=0031-9422&volume=71&issue=17-18&spage=2046&epage=2051&date=2010&atitle=Sulfur-containing+constituents+and+one+1H-pyrrole-2-carboxylic+acid+derivative+from+pineapple+[Ananas+comosus+(L.)+Merr.]+fruit-
dc.identifier.emailChang, RCC: rccchang@hku.hken_HK
dc.identifier.emailWang, M: mfwang@hku.hken_HK
dc.identifier.authorityChang, RCC=rp00470en_HK
dc.identifier.authorityWang, M=rp00800en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.phytochem.2010.08.014en_HK
dc.identifier.pmid20843530en_HK
dc.identifier.scopuseid_2-s2.0-78249262932en_HK
dc.identifier.hkuros186776en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-78249262932&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume71en_HK
dc.identifier.issue17-18en_HK
dc.identifier.spage2046en_HK
dc.identifier.epage2051en_HK
dc.identifier.isiWOS:000285325500012-
dc.publisher.placeUnited Kingdomen_HK
dc.relation.projectNatural tyrosinase inhibitors as skin whitening agents-
dc.identifier.scopusauthoridZheng, ZP=8451746600en_HK
dc.identifier.scopusauthoridMa, J=9248720900en_HK
dc.identifier.scopusauthoridCheng, KW=12141247000en_HK
dc.identifier.scopusauthoridChao, J=24558959000en_HK
dc.identifier.scopusauthoridZhu, Q=54909442800en_HK
dc.identifier.scopusauthoridChang, RCC=7403713410en_HK
dc.identifier.scopusauthoridZhao, M=7403535102en_HK
dc.identifier.scopusauthoridLin, ZX=26433004200en_HK
dc.identifier.scopusauthoridWang, M=7406691844en_HK
dc.identifier.citeulike7883048-

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