Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents

Genistein was glucosylated to its 7-O-β-D-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-D-glucoside and 7-O-β-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-D-glucoside by I. batatas, and M. polymorpha...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry letters 2008-08, Vol.37 (8), p.876-877
Hauptverfasser: Shimoda, Kei, Kobayashi, Tatsunari, Akagi, Masaaki, Hamada, Hatsuyuki, Hamada, Hiroki
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 877
container_issue 8
container_start_page 876
container_title Chemistry letters
container_volume 37
creator Shimoda, Kei
Kobayashi, Tatsunari
Akagi, Masaaki
Hamada, Hatsuyuki
Hamada, Hiroki
description Genistein was glucosylated to its 7-O-β-D-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-D-glucoside and 7-O-β-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-D-glucoside by I. batatas, and M. polymorpha gave 3-O-β-D-glucoside and 7-O-β-D-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding β-maltosides and β-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-β-maltooligosaccharides, quercetin 3-O-β-glucoside, and quercetin 7-O-β-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.
doi_str_mv 10.1246/cl.2008.876
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1461011462</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3135401481</sourcerecordid><originalsourceid>FETCH-LOGICAL-c506t-dd430ca0363c87dcf6d31b3a2173d16aa7560e4e70c5b145a993c3661bd84a0a3</originalsourceid><addsrcrecordid>eNptkMFOwzAMhiMEEmNw4gUicUQtSdOm3XGaYCBNGgi4EnlJumVqk5Fkh749GduBA5dYsT__tn-EbinJaVHyB9nlBSFN3tT8DI0oK5uM1LQ6RyPCOM9qUhSX6CqELUnUhBUj9PU-2LjRwQTsWrzszNoFkHID3ij9m5tra0LUxmKwCr_ttZc6Hn4Bv7qobTTQ4WkKmbFtB30P0fkBT9epFK7RRQtd0DenOEafT48fs-dssZy_zKaLTFaEx0ypkhEJaUkmm1rJlitGVwwKWjNFOUBdcaJLXRNZrWhZwWTCZLqIrlRTAgE2RndH3Z1333sdoti6vbdppKAlp4Smt0jU_ZGS3oXgdSt23vTgB0GJOBgoZCcOBopkYKKbE73RvZFJy0mj47CFHdg_-v-0_gBMS3cV</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1461011462</pqid></control><display><type>article</type><title>Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents</title><source>Oxford University Press Journals All Titles (1996-Current)</source><creator>Shimoda, Kei ; Kobayashi, Tatsunari ; Akagi, Masaaki ; Hamada, Hatsuyuki ; Hamada, Hiroki</creator><creatorcontrib>Shimoda, Kei ; Kobayashi, Tatsunari ; Akagi, Masaaki ; Hamada, Hatsuyuki ; Hamada, Hiroki</creatorcontrib><description>Genistein was glucosylated to its 7-O-β-D-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-D-glucoside and 7-O-β-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-D-glucoside by I. batatas, and M. polymorpha gave 3-O-β-D-glucoside and 7-O-β-D-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding β-maltosides and β-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-β-maltooligosaccharides, quercetin 3-O-β-glucoside, and quercetin 7-O-β-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.</description><identifier>ISSN: 0366-7022</identifier><identifier>EISSN: 1348-0715</identifier><identifier>DOI: 10.1246/cl.2008.876</identifier><language>eng</language><publisher>Tokyo: The Chemical Society of Japan</publisher><ispartof>Chemistry letters, 2008-08, Vol.37 (8), p.876-877</ispartof><rights>The Chemical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2008</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c506t-dd430ca0363c87dcf6d31b3a2173d16aa7560e4e70c5b145a993c3661bd84a0a3</citedby><cites>FETCH-LOGICAL-c506t-dd430ca0363c87dcf6d31b3a2173d16aa7560e4e70c5b145a993c3661bd84a0a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Shimoda, Kei</creatorcontrib><creatorcontrib>Kobayashi, Tatsunari</creatorcontrib><creatorcontrib>Akagi, Masaaki</creatorcontrib><creatorcontrib>Hamada, Hatsuyuki</creatorcontrib><creatorcontrib>Hamada, Hiroki</creatorcontrib><title>Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents</title><title>Chemistry letters</title><addtitle>Chemistry Letters</addtitle><description>Genistein was glucosylated to its 7-O-β-D-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-D-glucoside and 7-O-β-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-D-glucoside by I. batatas, and M. polymorpha gave 3-O-β-D-glucoside and 7-O-β-D-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding β-maltosides and β-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-β-maltooligosaccharides, quercetin 3-O-β-glucoside, and quercetin 7-O-β-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.</description><issn>0366-7022</issn><issn>1348-0715</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNptkMFOwzAMhiMEEmNw4gUicUQtSdOm3XGaYCBNGgi4EnlJumVqk5Fkh749GduBA5dYsT__tn-EbinJaVHyB9nlBSFN3tT8DI0oK5uM1LQ6RyPCOM9qUhSX6CqELUnUhBUj9PU-2LjRwQTsWrzszNoFkHID3ij9m5tra0LUxmKwCr_ttZc6Hn4Bv7qobTTQ4WkKmbFtB30P0fkBT9epFK7RRQtd0DenOEafT48fs-dssZy_zKaLTFaEx0ypkhEJaUkmm1rJlitGVwwKWjNFOUBdcaJLXRNZrWhZwWTCZLqIrlRTAgE2RndH3Z1333sdoti6vbdppKAlp4Smt0jU_ZGS3oXgdSt23vTgB0GJOBgoZCcOBopkYKKbE73RvZFJy0mj47CFHdg_-v-0_gBMS3cV</recordid><startdate>20080805</startdate><enddate>20080805</enddate><creator>Shimoda, Kei</creator><creator>Kobayashi, Tatsunari</creator><creator>Akagi, Masaaki</creator><creator>Hamada, Hatsuyuki</creator><creator>Hamada, Hiroki</creator><general>The Chemical Society of Japan</general><general>Chemical Society of Japan</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20080805</creationdate><title>Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents</title><author>Shimoda, Kei ; Kobayashi, Tatsunari ; Akagi, Masaaki ; Hamada, Hatsuyuki ; Hamada, Hiroki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c506t-dd430ca0363c87dcf6d31b3a2173d16aa7560e4e70c5b145a993c3661bd84a0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shimoda, Kei</creatorcontrib><creatorcontrib>Kobayashi, Tatsunari</creatorcontrib><creatorcontrib>Akagi, Masaaki</creatorcontrib><creatorcontrib>Hamada, Hatsuyuki</creatorcontrib><creatorcontrib>Hamada, Hiroki</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shimoda, Kei</au><au>Kobayashi, Tatsunari</au><au>Akagi, Masaaki</au><au>Hamada, Hatsuyuki</au><au>Hamada, Hiroki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents</atitle><jtitle>Chemistry letters</jtitle><addtitle>Chemistry Letters</addtitle><date>2008-08-05</date><risdate>2008</risdate><volume>37</volume><issue>8</issue><spage>876</spage><epage>877</epage><pages>876-877</pages><issn>0366-7022</issn><eissn>1348-0715</eissn><abstract>Genistein was glucosylated to its 7-O-β-D-glucoside by cultured cells of Ipomoea batatas, while cultured Marchantia polymorpha cells produced 4′-O-β-D-glucoside and 7-O-β-D-glucoside of genistein. On the other hand, quercetin was converted into its 3-O-β-D-glucoside by I. batatas, and M. polymorpha gave 3-O-β-D-glucoside and 7-O-β-D-glucoside of quercetin. These four glucosides were further glycosylated to the corresponding β-maltosides and β-maltotriosides by cyclodextrin glucanotransferase. Genistein 7-O-β-maltooligosaccharides, quercetin 3-O-β-glucoside, and quercetin 7-O-β-maltooligosaccharides showed potent inhibitory effects on histamine release from rat peritoneal mast cells.</abstract><cop>Tokyo</cop><pub>The Chemical Society of Japan</pub><doi>10.1246/cl.2008.876</doi><tpages>2</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0366-7022
ispartof Chemistry letters, 2008-08, Vol.37 (8), p.876-877
issn 0366-7022
1348-0715
language eng
recordid cdi_proquest_journals_1461011462
source Oxford University Press Journals All Titles (1996-Current)
title Synthesis of Oligosaccharides of Genistein and Quercetin as Potential Anti-inflammatory Agents
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T20%3A48%3A38IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Oligosaccharides%20of%20Genistein%20and%20Quercetin%20as%20Potential%20Anti-inflammatory%20Agents&rft.jtitle=Chemistry%20letters&rft.au=Shimoda,%20Kei&rft.date=2008-08-05&rft.volume=37&rft.issue=8&rft.spage=876&rft.epage=877&rft.pages=876-877&rft.issn=0366-7022&rft.eissn=1348-0715&rft_id=info:doi/10.1246/cl.2008.876&rft_dat=%3Cproquest_cross%3E3135401481%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1461011462&rft_id=info:pmid/&rfr_iscdi=true