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New cytotoxic azaphilones from Monascus purpureus-fermented rice (red yeast rice)

Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic...

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Published in:	Molecules (Basel, Switzerland) Switzerland), 2010-03, Vol.15 (3), p.1958-1966
Main Authors:	Li, Jin-Jie, Shang, Xiao-Ya, Li, Ling-Ling, Liu, Ming-Tao, Zheng, Jian-Quan, Jin, Zong-Lian
Format:	Article
Language:	English
Subjects:	absolute configurations azaphilones Benzopyrans - isolation & purification Benzopyrans - pharmacology Biological Products - chemistry Cell Line, Tumor Circular Dichroism Cytotoxicity Drug Screening Assays, Antitumor Humans Magnetic Resonance Spectroscopy Medical research Monascus purpureus Pigments, Biological - isolation & purification Pigments, Biological - pharmacology Spectrophotometry, Ultraviolet Spectroscopy, Fourier Transform Infrared Toxicity
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creator	Li, Jin-Jie Shang, Xiao-Ya Li, Ling-Ling Liu, Ming-Tao Zheng, Jian-Quan Jin, Zong-Lian
description	Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4 microM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration.
doi_str_mv	10.3390/molecules15031958
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Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4 microM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules15031958</identifier><identifier>PMID: 20336024</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>absolute configurations ; azaphilones ; Benzopyrans - isolation & purification ; Benzopyrans - pharmacology ; Biological Products - chemistry ; Cell Line, Tumor ; Circular Dichroism ; Cytotoxicity ; Drug Screening Assays, Antitumor ; Humans ; Magnetic Resonance Spectroscopy ; Medical research ; Monascus purpureus ; Pigments, Biological - isolation & purification ; Pigments, Biological - pharmacology ; Spectrophotometry, Ultraviolet ; Spectroscopy, Fourier Transform Infrared ; Toxicity</subject><ispartof>Molecules (Basel, Switzerland), 2010-03, Vol.15 (3), p.1958-1966</ispartof><rights>Copyright MDPI AG 2010</rights><rights>2010 by the authors; 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c492t-bafe8028cf6a9a50710bad5d3bc88bd16f95ac2fbce9009a67dbfc1c753406a33</citedby><cites>FETCH-LOGICAL-c492t-bafe8028cf6a9a50710bad5d3bc88bd16f95ac2fbce9009a67dbfc1c753406a33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/1531570090/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/1531570090?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20336024$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Jin-Jie</creatorcontrib><creatorcontrib>Shang, Xiao-Ya</creatorcontrib><creatorcontrib>Li, Ling-Ling</creatorcontrib><creatorcontrib>Liu, Ming-Tao</creatorcontrib><creatorcontrib>Zheng, Jian-Quan</creatorcontrib><creatorcontrib>Jin, Zong-Lian</creatorcontrib><title>New cytotoxic azaphilones from Monascus purpureus-fermented rice (red yeast rice)</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). 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Shang, Xiao-Ya ; Li, Ling-Ling ; Liu, Ming-Tao ; Zheng, Jian-Quan ; Jin, Zong-Lian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c492t-bafe8028cf6a9a50710bad5d3bc88bd16f95ac2fbce9009a67dbfc1c753406a33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>absolute configurations</topic><topic>azaphilones</topic><topic>Benzopyrans - isolation & purification</topic><topic>Benzopyrans - pharmacology</topic><topic>Biological Products - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Circular Dichroism</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical research</topic><topic>Monascus purpureus</topic><topic>Pigments, Biological - isolation & purification</topic><topic>Pigments, Biological - pharmacology</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jin-Jie</creatorcontrib><creatorcontrib>Shang, Xiao-Ya</creatorcontrib><creatorcontrib>Li, Ling-Ling</creatorcontrib><creatorcontrib>Liu, Ming-Tao</creatorcontrib><creatorcontrib>Zheng, Jian-Quan</creatorcontrib><creatorcontrib>Jin, Zong-Lian</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Access via ProQuest (Open Access)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jin-Jie</au><au>Shang, Xiao-Ya</au><au>Li, Ling-Ling</au><au>Liu, Ming-Tao</au><au>Zheng, Jian-Quan</au><au>Jin, Zong-Lian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New cytotoxic azaphilones from Monascus purpureus-fermented rice (red yeast rice)</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2010-03-18</date><risdate>2010</risdate><volume>15</volume><issue>3</issue><spage>1958</spage><epage>1966</epage><pages>1958-1966</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>Using a cell-based cytotoxicity assay three new cytotoxic azaphilones, including two stereoisomers and designated monapurones A-C (1-3), were isolated from the extract of Monascus purpureus-fermented rice (red yeast rice). Their structures were elucidated by detailed interpretation of spectroscopic and chemical data. The relative configurations were assigned on the basis of analysis of NOE data, and the absolute configurations were determined by direct comparison of their CD spectra with those of known azaphilones and chemical correlations. In the in vitro assays, monapurones A-C (1-3) showed selective cytotoxicity against human cancer cell line A549 with IC50 values of 3.8, 2.8 and 2.4 microM respectively, while exhibiting no significant toxicity to normal MRC-5 and WI-38 cells at the same concentration.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>20336024</pmid><doi>10.3390/molecules15031958</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record>
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subjects	absolute configurations azaphilones Benzopyrans - isolation & purification Benzopyrans - pharmacology Biological Products - chemistry Cell Line, Tumor Circular Dichroism Cytotoxicity Drug Screening Assays, Antitumor Humans Magnetic Resonance Spectroscopy Medical research Monascus purpureus Pigments, Biological - isolation & purification Pigments, Biological - pharmacology Spectrophotometry, Ultraviolet Spectroscopy, Fourier Transform Infrared Toxicity
title	New cytotoxic azaphilones from Monascus purpureus-fermented rice (red yeast rice)
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