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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?
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.
Persistent Identifierhttp://hdl.handle.net/10722/136239
ISSN
2014 Impact Factor: 2.547
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

 

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.pmid20843530-
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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