Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative
Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes Buceros bicornis (great hornbill) and Penelopides panini (Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-choles...
Gespeichert in:
| Veröffentlicht in: | Lipids 2016-06, Vol.51 (6), p.757-768 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 768 |
|---|---|
| container_issue | 6 |
| container_start_page | 757 |
| container_title | Lipids |
| container_volume | 51 |
| creator | Satoh, Rika Ogata, Hiroaki Saito, Tetsuya Zhou, Biao Omura, Kaoru Kurabuchi, Satoshi Mitamura, Kuniko Ikegawa, Shigeo Hagey, Lee R. Hofmann, Alan F. Iida, Takashi |
| description | Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes
Buceros bicornis
(great hornbill) and
Penelopides panini
(Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24
R
,25
S
)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to
B. bicornis
and
P. panini.
The previous stereochemical assignment for (24
R
,25
S
)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24
S
,25
S
)-configuration. |
| doi_str_mv | 10.1007/s11745-016-4150-0 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1792370484</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1792370484</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3077-f8111543c89ceb4e23465a67a27adeee05e5aa8825beb0f5d805af90f9f651d03</originalsourceid><addsrcrecordid>eNqFkMFuEzEQhi0EoqHwAFyQj60U07HXjnePpaUkUlARhLPl3Z0ljjbrYmfb7rlPVB4kz4SjLRzhMLJG-r9f44-QtxzecwB9FjnXUjHgMya5AgbPyIQrlbMiA_2cTACEZFIAPyKvYtyklctCvSRHQnPIIZMT8rC68_Sz3fhAP7gW6Xnl6khdR3drpHMfutK1bZzSEyG_ToX6dsqy_eNUp0nVq-DWQx38_cDU_her1r7FuLMdE5r5oaUr2wfXIbVdTRe7SLnYP7L5SNBLDO7W7twtviYvGttGfPP0HpPvVx9XF3O2vP60uDhfsip9R7Mm55wrmVV5UWEpUWRypuxMW6FtjYigUFmb50KVWEKj6hyUbQpoimameA3ZMTkZe2-C_9mnS83WxQrb1nbo-2i4LkSmQeYyRfkYrYKPMWBjboLb2jAYDubg3ozuTXJvDu7Nof7dU31fbrH-S_yRnQJ6DNwl08P_G81y8eUStNKJFCMZE9T9wGA2vg9dkvWPe34DxXufWg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1792370484</pqid></control><display><type>article</type><title>Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><source>Springer Nature - Complete Springer Journals</source><creator>Satoh, Rika ; Ogata, Hiroaki ; Saito, Tetsuya ; Zhou, Biao ; Omura, Kaoru ; Kurabuchi, Satoshi ; Mitamura, Kuniko ; Ikegawa, Shigeo ; Hagey, Lee R. ; Hofmann, Alan F. ; Iida, Takashi</creator><creatorcontrib>Satoh, Rika ; Ogata, Hiroaki ; Saito, Tetsuya ; Zhou, Biao ; Omura, Kaoru ; Kurabuchi, Satoshi ; Mitamura, Kuniko ; Ikegawa, Shigeo ; Hagey, Lee R. ; Hofmann, Alan F. ; Iida, Takashi</creatorcontrib><description>Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes
Buceros bicornis
(great hornbill) and
Penelopides panini
(Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24
R
,25
S
)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to
B. bicornis
and
P. panini.
The previous stereochemical assignment for (24
R
,25
S
)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24
S
,25
S
)-configuration.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-016-4150-0</identifier><identifier>PMID: 27108034</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>(24R,25S)‐3α,7α,12α,24‐Tetrahydroxy‐5β‐cholestan‐27‐oyl taurine ; (24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl taurine ; 24‐Hydroxylated bile acid ; Animals ; Bile Acids and Salts - analysis ; Bile Acids and Salts - chemistry ; Biomedical and Life Sciences ; Birds - metabolism ; Cholestanoic acid ; Chromatography, High Pressure Liquid ; Crystallography, X-Ray ; Gallbladder - chemistry ; Great hornbill ; Life Sciences ; Lipidology ; Medical Biochemistry ; Medicinal Chemistry ; Microbial Genetics and Genomics ; Molecular Structure ; Neurochemistry ; NMR ; Nutrition ; Original Article ; RP‐HPLC ; Stereoisomerism ; Taurine - analogs & derivatives ; Taurine - chemistry ; Taurine - isolation & purification ; Varanic acid ; Visayan tarictic hornbill ; X‐ray crystallography</subject><ispartof>Lipids, 2016-06, Vol.51 (6), p.757-768</ispartof><rights>AOCS 2016</rights><rights>2016 American Oil Chemists' Society (AOCS)</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3077-f8111543c89ceb4e23465a67a27adeee05e5aa8825beb0f5d805af90f9f651d03</citedby><cites>FETCH-LOGICAL-c3077-f8111543c89ceb4e23465a67a27adeee05e5aa8825beb0f5d805af90f9f651d03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11745-016-4150-0$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11745-016-4150-0$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,41467,42536,45553,45554,51298</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27108034$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Satoh, Rika</creatorcontrib><creatorcontrib>Ogata, Hiroaki</creatorcontrib><creatorcontrib>Saito, Tetsuya</creatorcontrib><creatorcontrib>Zhou, Biao</creatorcontrib><creatorcontrib>Omura, Kaoru</creatorcontrib><creatorcontrib>Kurabuchi, Satoshi</creatorcontrib><creatorcontrib>Mitamura, Kuniko</creatorcontrib><creatorcontrib>Ikegawa, Shigeo</creatorcontrib><creatorcontrib>Hagey, Lee R.</creatorcontrib><creatorcontrib>Hofmann, Alan F.</creatorcontrib><creatorcontrib>Iida, Takashi</creatorcontrib><title>Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative</title><title>Lipids</title><addtitle>Lipids</addtitle><addtitle>Lipids</addtitle><description>Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes
Buceros bicornis
(great hornbill) and
Penelopides panini
(Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24
R
,25
S
)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to
B. bicornis
and
P. panini.
The previous stereochemical assignment for (24
R
,25
S
)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24
S
,25
S
)-configuration.</description><subject>(24R,25S)‐3α,7α,12α,24‐Tetrahydroxy‐5β‐cholestan‐27‐oyl taurine</subject><subject>(24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl taurine</subject><subject>24‐Hydroxylated bile acid</subject><subject>Animals</subject><subject>Bile Acids and Salts - analysis</subject><subject>Bile Acids and Salts - chemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Birds - metabolism</subject><subject>Cholestanoic acid</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Crystallography, X-Ray</subject><subject>Gallbladder - chemistry</subject><subject>Great hornbill</subject><subject>Life Sciences</subject><subject>Lipidology</subject><subject>Medical Biochemistry</subject><subject>Medicinal Chemistry</subject><subject>Microbial Genetics and Genomics</subject><subject>Molecular Structure</subject><subject>Neurochemistry</subject><subject>NMR</subject><subject>Nutrition</subject><subject>Original Article</subject><subject>RP‐HPLC</subject><subject>Stereoisomerism</subject><subject>Taurine - analogs & derivatives</subject><subject>Taurine - chemistry</subject><subject>Taurine - isolation & purification</subject><subject>Varanic acid</subject><subject>Visayan tarictic hornbill</subject><subject>X‐ray crystallography</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFuEzEQhi0EoqHwAFyQj60U07HXjnePpaUkUlARhLPl3Z0ljjbrYmfb7rlPVB4kz4SjLRzhMLJG-r9f44-QtxzecwB9FjnXUjHgMya5AgbPyIQrlbMiA_2cTACEZFIAPyKvYtyklctCvSRHQnPIIZMT8rC68_Sz3fhAP7gW6Xnl6khdR3drpHMfutK1bZzSEyG_ToX6dsqy_eNUp0nVq-DWQx38_cDU_her1r7FuLMdE5r5oaUr2wfXIbVdTRe7SLnYP7L5SNBLDO7W7twtviYvGttGfPP0HpPvVx9XF3O2vP60uDhfsip9R7Mm55wrmVV5UWEpUWRypuxMW6FtjYigUFmb50KVWEKj6hyUbQpoimameA3ZMTkZe2-C_9mnS83WxQrb1nbo-2i4LkSmQeYyRfkYrYKPMWBjboLb2jAYDubg3ozuTXJvDu7Nof7dU31fbrH-S_yRnQJ6DNwl08P_G81y8eUStNKJFCMZE9T9wGA2vg9dkvWPe34DxXufWg</recordid><startdate>201606</startdate><enddate>201606</enddate><creator>Satoh, Rika</creator><creator>Ogata, Hiroaki</creator><creator>Saito, Tetsuya</creator><creator>Zhou, Biao</creator><creator>Omura, Kaoru</creator><creator>Kurabuchi, Satoshi</creator><creator>Mitamura, Kuniko</creator><creator>Ikegawa, Shigeo</creator><creator>Hagey, Lee R.</creator><creator>Hofmann, Alan F.</creator><creator>Iida, Takashi</creator><general>Springer Berlin Heidelberg</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>201606</creationdate><title>Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative</title><author>Satoh, Rika ; Ogata, Hiroaki ; Saito, Tetsuya ; Zhou, Biao ; Omura, Kaoru ; Kurabuchi, Satoshi ; Mitamura, Kuniko ; Ikegawa, Shigeo ; Hagey, Lee R. ; Hofmann, Alan F. ; Iida, Takashi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3077-f8111543c89ceb4e23465a67a27adeee05e5aa8825beb0f5d805af90f9f651d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>(24R,25S)‐3α,7α,12α,24‐Tetrahydroxy‐5β‐cholestan‐27‐oyl taurine</topic><topic>(24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl taurine</topic><topic>24‐Hydroxylated bile acid</topic><topic>Animals</topic><topic>Bile Acids and Salts - analysis</topic><topic>Bile Acids and Salts - chemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Birds - metabolism</topic><topic>Cholestanoic acid</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Crystallography, X-Ray</topic><topic>Gallbladder - chemistry</topic><topic>Great hornbill</topic><topic>Life Sciences</topic><topic>Lipidology</topic><topic>Medical Biochemistry</topic><topic>Medicinal Chemistry</topic><topic>Microbial Genetics and Genomics</topic><topic>Molecular Structure</topic><topic>Neurochemistry</topic><topic>NMR</topic><topic>Nutrition</topic><topic>Original Article</topic><topic>RP‐HPLC</topic><topic>Stereoisomerism</topic><topic>Taurine - analogs & derivatives</topic><topic>Taurine - chemistry</topic><topic>Taurine - isolation & purification</topic><topic>Varanic acid</topic><topic>Visayan tarictic hornbill</topic><topic>X‐ray crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Satoh, Rika</creatorcontrib><creatorcontrib>Ogata, Hiroaki</creatorcontrib><creatorcontrib>Saito, Tetsuya</creatorcontrib><creatorcontrib>Zhou, Biao</creatorcontrib><creatorcontrib>Omura, Kaoru</creatorcontrib><creatorcontrib>Kurabuchi, Satoshi</creatorcontrib><creatorcontrib>Mitamura, Kuniko</creatorcontrib><creatorcontrib>Ikegawa, Shigeo</creatorcontrib><creatorcontrib>Hagey, Lee R.</creatorcontrib><creatorcontrib>Hofmann, Alan F.</creatorcontrib><creatorcontrib>Iida, Takashi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Satoh, Rika</au><au>Ogata, Hiroaki</au><au>Saito, Tetsuya</au><au>Zhou, Biao</au><au>Omura, Kaoru</au><au>Kurabuchi, Satoshi</au><au>Mitamura, Kuniko</au><au>Ikegawa, Shigeo</au><au>Hagey, Lee R.</au><au>Hofmann, Alan F.</au><au>Iida, Takashi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative</atitle><jtitle>Lipids</jtitle><stitle>Lipids</stitle><addtitle>Lipids</addtitle><date>2016-06</date><risdate>2016</risdate><volume>51</volume><issue>6</issue><spage>757</spage><epage>768</epage><pages>757-768</pages><issn>0024-4201</issn><eissn>1558-9307</eissn><abstract>Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes
Buceros bicornis
(great hornbill) and
Penelopides panini
(Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24
R
,25
S
)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to
B. bicornis
and
P. panini.
The previous stereochemical assignment for (24
R
,25
S
)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24
S
,25
S
)-configuration.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>27108034</pmid><doi>10.1007/s11745-016-4150-0</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0024-4201 |
| ispartof | Lipids, 2016-06, Vol.51 (6), p.757-768 |
| issn | 0024-4201 1558-9307 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1792370484 |
| source | MEDLINE; Wiley Online Library Journals Frontfile Complete; Springer Nature - Complete Springer Journals |
| subjects | (24R,25S)‐3α,7α,12α,24‐Tetrahydroxy‐5β‐cholestan‐27‐oyl taurine (24R,25S)‐3α,7α,24‐Trihydroxy‐5β‐cholestan‐27‐oyl taurine 24‐Hydroxylated bile acid Animals Bile Acids and Salts - analysis Bile Acids and Salts - chemistry Biomedical and Life Sciences Birds - metabolism Cholestanoic acid Chromatography, High Pressure Liquid Crystallography, X-Ray Gallbladder - chemistry Great hornbill Life Sciences Lipidology Medical Biochemistry Medicinal Chemistry Microbial Genetics and Genomics Molecular Structure Neurochemistry NMR Nutrition Original Article RP‐HPLC Stereoisomerism Taurine - analogs & derivatives Taurine - chemistry Taurine - isolation & purification Varanic acid Visayan tarictic hornbill X‐ray crystallography |
| title | Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T08%3A36%3A33IST&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=Two%20Major%20Bile%20Acids%20in%20the%20Hornbills,%20(24R,25S)-3%CE%B1,7%CE%B1,24-Trihydroxy-5%CE%B2-cholestan-27-oyl%20Taurine%20and%20Its%2012%CE%B1-Hydroxy%20Derivative&rft.jtitle=Lipids&rft.au=Satoh,%20Rika&rft.date=2016-06&rft.volume=51&rft.issue=6&rft.spage=757&rft.epage=768&rft.pages=757-768&rft.issn=0024-4201&rft.eissn=1558-9307&rft_id=info:doi/10.1007/s11745-016-4150-0&rft_dat=%3Cproquest_cross%3E1792370484%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=1792370484&rft_id=info:pmid/27108034&rfr_iscdi=true |