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Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists
► Three new steroids 1–3 were isolated from a marine organism Dendronephthya gigantea. ► Relative stereochemistry was elucidated by the analysis of HRMS and 2-D NMR. ► New steroids 1 and 2 showed potent inhibitory activity against FXR. Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxochole...
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| Published in: | Steroids 2012-04, Vol.77 (5), p.355-359 |
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| container_end_page | 359 |
| container_issue | 5 |
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| container_title | Steroids |
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| creator | Shin, Kyoungjin Chin, Jungwook Hahn, Dongyup Lee, Jaehwan Hwang, Hoosang Won, Dong Hwan Ham, Jungyeob Choi, Hyukjae Kang, Eunsoo Kim, Hiyoung Ju, Moon Kyeong Nam, Sang-Jip Kang, Heonjoong |
| description | ► Three new steroids 1–3 were isolated from a marine organism Dendronephthya gigantea. ► Relative stereochemistry was elucidated by the analysis of HRMS and 2-D NMR. ► New steroids 1 and 2 showed potent inhibitory activity against FXR.
Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC50’s 14 and 15μM. |
| doi_str_mv | 10.1016/j.steroids.2011.12.027 |
| format | article |
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Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC50’s 14 and 15μM.</description><identifier>ISSN: 0039-128X</identifier><identifier>EISSN: 1878-5867</identifier><identifier>DOI: 10.1016/j.steroids.2011.12.027</identifier><identifier>PMID: 22266736</identifier><identifier>CODEN: STEDAM</identifier><language>eng</language><publisher>Kidlington: Elsevier Inc</publisher><subject>Animals ; Anthozoa - chemistry ; Biological and medical sciences ; Cell Line ; Cell Survival - drug effects ; Cholestasis ; Cholesterol - analogs & derivatives ; Cholesterol - chemistry ; Cholesterol - pharmacology ; Dendronephthya gigantea ; Dose-Response Relationship, Drug ; Farnesoid X-activated receptor ; Fundamental and applied biological sciences. Psychology ; Gastroenterology. Liver. Pancreas. Abdomen ; Humans ; Inhibitory Concentration 50 ; Liver. Biliary tract. Portal circulation. Exocrine pancreas ; Magnetic Resonance Spectroscopy ; Medical sciences ; Molecular Structure ; Other diseases. Semiology ; Receptors, Cytoplasmic and Nuclear - antagonists & inhibitors ; Receptors, Cytoplasmic and Nuclear - genetics ; Receptors, Cytoplasmic and Nuclear - metabolism ; Sterols - chemistry ; Sterols - isolation & purification ; Sterols - pharmacology ; Transfection ; Vertebrates: endocrinology</subject><ispartof>Steroids, 2012-04, Vol.77 (5), p.355-359</ispartof><rights>2012 Elsevier Inc.</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c397t-4555a6456fbe5e4ab5cfbe7174650ac51b5155ed2ecaed9ba144d723aa131b6e3</citedby><cites>FETCH-LOGICAL-c397t-4555a6456fbe5e4ab5cfbe7174650ac51b5155ed2ecaed9ba144d723aa131b6e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25795742$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22266736$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shin, Kyoungjin</creatorcontrib><creatorcontrib>Chin, Jungwook</creatorcontrib><creatorcontrib>Hahn, Dongyup</creatorcontrib><creatorcontrib>Lee, Jaehwan</creatorcontrib><creatorcontrib>Hwang, Hoosang</creatorcontrib><creatorcontrib>Won, Dong Hwan</creatorcontrib><creatorcontrib>Ham, Jungyeob</creatorcontrib><creatorcontrib>Choi, Hyukjae</creatorcontrib><creatorcontrib>Kang, Eunsoo</creatorcontrib><creatorcontrib>Kim, Hiyoung</creatorcontrib><creatorcontrib>Ju, Moon Kyeong</creatorcontrib><creatorcontrib>Nam, Sang-Jip</creatorcontrib><creatorcontrib>Kang, Heonjoong</creatorcontrib><title>Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists</title><title>Steroids</title><addtitle>Steroids</addtitle><description>► Three new steroids 1–3 were isolated from a marine organism Dendronephthya gigantea. ► Relative stereochemistry was elucidated by the analysis of HRMS and 2-D NMR. ► New steroids 1 and 2 showed potent inhibitory activity against FXR.
Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC50’s 14 and 15μM.</description><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Cholestasis</subject><subject>Cholesterol - analogs & derivatives</subject><subject>Cholesterol - chemistry</subject><subject>Cholesterol - pharmacology</subject><subject>Dendronephthya gigantea</subject><subject>Dose-Response Relationship, Drug</subject><subject>Farnesoid X-activated receptor</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gastroenterology. Liver. Pancreas. Abdomen</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Liver. Biliary tract. Portal circulation. Exocrine pancreas</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Other diseases. Semiology</subject><subject>Receptors, Cytoplasmic and Nuclear - antagonists & inhibitors</subject><subject>Receptors, Cytoplasmic and Nuclear - genetics</subject><subject>Receptors, Cytoplasmic and Nuclear - metabolism</subject><subject>Sterols - chemistry</subject><subject>Sterols - isolation & purification</subject><subject>Sterols - pharmacology</subject><subject>Transfection</subject><subject>Vertebrates: endocrinology</subject><issn>0039-128X</issn><issn>1878-5867</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkMFu1DAQhi0EokvhFSpfEBcSbCe2kxuohYJUiQMg9WYmzmTrVTZePN5KfXu82m05cpo5fP8_o4-xCylqKaT5sKkpY4phpFoJKWupaqHsM7aSne0q3Rn7nK2EaPpKqu72jL0i2gghTNOrl-xMKWWMbcyK_f5xqJmJTyluOXCKU-Y-Jpjf8ytcxhQX3N3luwfg67CGJSNwKDSkBamc57cV-BzuIePIE3rc5Zh44WAdl0CZXrMXE8yEb07znP368vnn5dfq5vv1t8tPN5VvepurVmsNptVmGlBjC4P2ZbPStkYL8FoOWmqNo0IPOPYDyLYdrWoAZCMHg805e3fs3aX4Z4-U3TaQx3mGBeOeXK-6xpQ-U0hzJH2KRAknt0thC-nBSeEOct3GPcp1B7lOKlfkluDF6cR-2OL4FHu0WYC3JwDIwzwlWHygf5y2vbatKtzHI4dFyH3A5MgHXDyOoSjMbozhf7_8BbEDnbM</recordid><startdate>20120401</startdate><enddate>20120401</enddate><creator>Shin, Kyoungjin</creator><creator>Chin, Jungwook</creator><creator>Hahn, Dongyup</creator><creator>Lee, Jaehwan</creator><creator>Hwang, Hoosang</creator><creator>Won, Dong Hwan</creator><creator>Ham, Jungyeob</creator><creator>Choi, Hyukjae</creator><creator>Kang, Eunsoo</creator><creator>Kim, Hiyoung</creator><creator>Ju, Moon Kyeong</creator><creator>Nam, Sang-Jip</creator><creator>Kang, Heonjoong</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><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>20120401</creationdate><title>Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists</title><author>Shin, Kyoungjin ; Chin, Jungwook ; Hahn, Dongyup ; Lee, Jaehwan ; Hwang, Hoosang ; Won, Dong Hwan ; Ham, Jungyeob ; Choi, Hyukjae ; Kang, Eunsoo ; Kim, Hiyoung ; Ju, Moon Kyeong ; Nam, Sang-Jip ; Kang, Heonjoong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c397t-4555a6456fbe5e4ab5cfbe7174650ac51b5155ed2ecaed9ba144d723aa131b6e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Cholestasis</topic><topic>Cholesterol - analogs & derivatives</topic><topic>Cholesterol - chemistry</topic><topic>Cholesterol - pharmacology</topic><topic>Dendronephthya gigantea</topic><topic>Dose-Response Relationship, Drug</topic><topic>Farnesoid X-activated receptor</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gastroenterology. Liver. Pancreas. Abdomen</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Liver. Biliary tract. Portal circulation. Exocrine pancreas</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Other diseases. 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Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC50’s 14 and 15μM.</abstract><cop>Kidlington</cop><pub>Elsevier Inc</pub><pmid>22266736</pmid><doi>10.1016/j.steroids.2011.12.027</doi><tpages>5</tpages></addata></record> |
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| subjects | Animals Anthozoa - chemistry Biological and medical sciences Cell Line Cell Survival - drug effects Cholestasis Cholesterol - analogs & derivatives Cholesterol - chemistry Cholesterol - pharmacology Dendronephthya gigantea Dose-Response Relationship, Drug Farnesoid X-activated receptor Fundamental and applied biological sciences. Psychology Gastroenterology. Liver. Pancreas. Abdomen Humans Inhibitory Concentration 50 Liver. Biliary tract. Portal circulation. Exocrine pancreas Magnetic Resonance Spectroscopy Medical sciences Molecular Structure Other diseases. Semiology Receptors, Cytoplasmic and Nuclear - antagonists & inhibitors Receptors, Cytoplasmic and Nuclear - genetics Receptors, Cytoplasmic and Nuclear - metabolism Sterols - chemistry Sterols - isolation & purification Sterols - pharmacology Transfection Vertebrates: endocrinology |
| title | Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists |
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