title: Sulfur-containing constituents and one 1H-pyrrole-2-carboxylic acid derivative from pineapple [Ananas comosus (L.) Merr.] fruit.
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.
authors.affiliation: School of Biological Sciences, The University of Hong Kong, Hong Kong, PR China.
authors.forename: Zong-Ping
authors.initials: ZP
authors.lastname: Zheng
authors.forename: Jinyu
authors.initials: J
authors.lastname: Ma
authors.forename: Ka-Wing
authors.initials: KW
authors.lastname: Cheng
authors.forename: Jianfei
authors.initials: J
authors.lastname: Chao
authors.forename: Qin
authors.initials: Q
authors.lastname: Zhu
authors.forename: Raymond Chuen-Chung
authors.initials: RC
authors.lastname: Chang
authors.forename: Ming
authors.initials: M
authors.lastname: Zhao
authors.forename: Zhi-Xiu
authors.initials: ZX
authors.lastname: Lin
authors.forename: Mingfu
authors.initials: M
authors.lastname: Wang
mesh_terms: D031230:Ananas / Q000737:chemistry*; D057886:Bleaching Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D019906:Nuclear Magnetic Resonance, Biomolecular; D010421:Pentanoic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011758:Pyrroles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012867:Skin / Q000187:drug effects; D013457:Sulfur Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C555470:(S)-2-amino-5-((R)-1-(carboxymethylamino)-3-((E)-3-(4-hydroxyphenyl)allylthio)-1-oxopropan-2-ylamino)-5-oxopentanoic acid; C555469:(S)-2-amino-5-((R)-1-carboxy-2-((E)-3-(4-hydroxy-3-methoxyphenyl)allylthio)ethyl-amino)-5-oxopentanoic acid; C555471:6-(3-(1H-pyrrole-2-carbonyloxy)-2-hydroxypropoxy)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylic acid; D057886:Bleaching Agents; D002264:Carboxylic Acids; D010421:Pentanoic Acids; D011758:Pyrroles; D013457:Sulfur Compounds; D014442:Monophenol Monooxygenase