Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia
Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated fro...
Gespeichert in:
| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2014-08, Vol.77 (8), p.1948-1954 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1954 |
|---|---|
| container_issue | 8 |
| container_start_page | 1948 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 77 |
| creator | Zeng, Junfen Xue, Yongbo Shu, Penghua Qian, Huiqin Sa, Rongjian Xiang, Ming Li, Xiao-Nian Luo, Zengwei Yao, Guangmin Zhang, Yonghui |
| description | Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1–4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA. |
| doi_str_mv | 10.1021/np500465g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1710985928</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1710985928</sourcerecordid><originalsourceid>FETCH-LOGICAL-a315t-51ff4702ea86a550bdc4e993fa02f2569de7356a434390c28cfaad0831024bca3</originalsourceid><addsrcrecordid>eNpt0D1PwzAYBGALgWgpDPwBlAUJhsDrr9Qeq1CgUiUWmCPXscFVHQc7KeLfE9TSiemWRyfdIXSJ4Q4DwfdNywFYwd-P0BhzAnkBhB-jMeCC5lQUbITOUloDAAXJT9GIcBBSMD5G8wfXmdiaJrg6ZV-u-8gW3vdNSH3bRpOS25pspju3dZ0zKbMx-Kx0TaN88L3PtBqIOkcnVm2SudjnBL09zl_L53z58rQoZ8tcUcy7nGNr2RSIUaJQnMOq1sxISa0CYgkvZG2mlBeKUUYlaCK0VaoGQYeVbKUVnaCbXW8bw2dvUld5l7TZbFRjQp8qPMUgBZdEDPR2R3UMKUVjqzY6r-J3haH6fa06vDbYq31tv_KmPsi_mwZwvQNKp2od-tgMK_8p-gH8tHPm</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1710985928</pqid></control><display><type>article</type><title>Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia</title><source>MEDLINE</source><source>ACS Publications</source><creator>Zeng, Junfen ; Xue, Yongbo ; Shu, Penghua ; Qian, Huiqin ; Sa, Rongjian ; Xiang, Ming ; Li, Xiao-Nian ; Luo, Zengwei ; Yao, Guangmin ; Zhang, Yonghui</creator><creatorcontrib>Zeng, Junfen ; Xue, Yongbo ; Shu, Penghua ; Qian, Huiqin ; Sa, Rongjian ; Xiang, Ming ; Li, Xiao-Nian ; Luo, Zengwei ; Yao, Guangmin ; Zhang, Yonghui</creatorcontrib><description>Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1–4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np500465g</identifier><identifier>PMID: 25089845</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Cinnamomum aromaticum - chemistry ; Concanavalin A - pharmacology ; Crystallography, X-Ray ; Diterpenes - chemistry ; Diterpenes - immunology ; Diterpenes - isolation & purification ; Drugs, Chinese Herbal - chemistry ; Drugs, Chinese Herbal - isolation & purification ; Drugs, Chinese Herbal - pharmacology ; Immunosuppressive Agents - chemistry ; Immunosuppressive Agents - immunology ; Immunosuppressive Agents - isolation & purification ; Mice ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Plant Bark - chemistry ; T-Lymphocytes - drug effects</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-08, Vol.77 (8), p.1948-1954</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-51ff4702ea86a550bdc4e993fa02f2569de7356a434390c28cfaad0831024bca3</citedby><cites>FETCH-LOGICAL-a315t-51ff4702ea86a550bdc4e993fa02f2569de7356a434390c28cfaad0831024bca3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np500465g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np500465g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25089845$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zeng, Junfen</creatorcontrib><creatorcontrib>Xue, Yongbo</creatorcontrib><creatorcontrib>Shu, Penghua</creatorcontrib><creatorcontrib>Qian, Huiqin</creatorcontrib><creatorcontrib>Sa, Rongjian</creatorcontrib><creatorcontrib>Xiang, Ming</creatorcontrib><creatorcontrib>Li, Xiao-Nian</creatorcontrib><creatorcontrib>Luo, Zengwei</creatorcontrib><creatorcontrib>Yao, Guangmin</creatorcontrib><creatorcontrib>Zhang, Yonghui</creatorcontrib><title>Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1–4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.</description><subject>Animals</subject><subject>Cinnamomum aromaticum - chemistry</subject><subject>Concanavalin A - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - immunology</subject><subject>Diterpenes - isolation & purification</subject><subject>Drugs, Chinese Herbal - chemistry</subject><subject>Drugs, Chinese Herbal - isolation & purification</subject><subject>Drugs, Chinese Herbal - pharmacology</subject><subject>Immunosuppressive Agents - chemistry</subject><subject>Immunosuppressive Agents - immunology</subject><subject>Immunosuppressive Agents - isolation & purification</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Plant Bark - chemistry</subject><subject>T-Lymphocytes - drug effects</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0D1PwzAYBGALgWgpDPwBlAUJhsDrr9Qeq1CgUiUWmCPXscFVHQc7KeLfE9TSiemWRyfdIXSJ4Q4DwfdNywFYwd-P0BhzAnkBhB-jMeCC5lQUbITOUloDAAXJT9GIcBBSMD5G8wfXmdiaJrg6ZV-u-8gW3vdNSH3bRpOS25pspju3dZ0zKbMx-Kx0TaN88L3PtBqIOkcnVm2SudjnBL09zl_L53z58rQoZ8tcUcy7nGNr2RSIUaJQnMOq1sxISa0CYgkvZG2mlBeKUUYlaCK0VaoGQYeVbKUVnaCbXW8bw2dvUld5l7TZbFRjQp8qPMUgBZdEDPR2R3UMKUVjqzY6r-J3haH6fa06vDbYq31tv_KmPsi_mwZwvQNKp2od-tgMK_8p-gH8tHPm</recordid><startdate>20140822</startdate><enddate>20140822</enddate><creator>Zeng, Junfen</creator><creator>Xue, Yongbo</creator><creator>Shu, Penghua</creator><creator>Qian, Huiqin</creator><creator>Sa, Rongjian</creator><creator>Xiang, Ming</creator><creator>Li, Xiao-Nian</creator><creator>Luo, Zengwei</creator><creator>Yao, Guangmin</creator><creator>Zhang, Yonghui</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20140822</creationdate><title>Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia</title><author>Zeng, Junfen ; Xue, Yongbo ; Shu, Penghua ; Qian, Huiqin ; Sa, Rongjian ; Xiang, Ming ; Li, Xiao-Nian ; Luo, Zengwei ; Yao, Guangmin ; Zhang, Yonghui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-51ff4702ea86a550bdc4e993fa02f2569de7356a434390c28cfaad0831024bca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Animals</topic><topic>Cinnamomum aromaticum - chemistry</topic><topic>Concanavalin A - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - immunology</topic><topic>Diterpenes - isolation & purification</topic><topic>Drugs, Chinese Herbal - chemistry</topic><topic>Drugs, Chinese Herbal - isolation & purification</topic><topic>Drugs, Chinese Herbal - pharmacology</topic><topic>Immunosuppressive Agents - chemistry</topic><topic>Immunosuppressive Agents - immunology</topic><topic>Immunosuppressive Agents - isolation & purification</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Plant Bark - chemistry</topic><topic>T-Lymphocytes - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeng, Junfen</creatorcontrib><creatorcontrib>Xue, Yongbo</creatorcontrib><creatorcontrib>Shu, Penghua</creatorcontrib><creatorcontrib>Qian, Huiqin</creatorcontrib><creatorcontrib>Sa, Rongjian</creatorcontrib><creatorcontrib>Xiang, Ming</creatorcontrib><creatorcontrib>Li, Xiao-Nian</creatorcontrib><creatorcontrib>Luo, Zengwei</creatorcontrib><creatorcontrib>Yao, Guangmin</creatorcontrib><creatorcontrib>Zhang, Yonghui</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeng, Junfen</au><au>Xue, Yongbo</au><au>Shu, Penghua</au><au>Qian, Huiqin</au><au>Sa, Rongjian</au><au>Xiang, Ming</au><au>Li, Xiao-Nian</au><au>Luo, Zengwei</au><au>Yao, Guangmin</au><au>Zhang, Yonghui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2014-08-22</date><risdate>2014</risdate><volume>77</volume><issue>8</issue><spage>1948</spage><epage>1954</epage><pages>1948-1954</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1–4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>25089845</pmid><doi>10.1021/np500465g</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2014-08, Vol.77 (8), p.1948-1954 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1710985928 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Cinnamomum aromaticum - chemistry Concanavalin A - pharmacology Crystallography, X-Ray Diterpenes - chemistry Diterpenes - immunology Diterpenes - isolation & purification Drugs, Chinese Herbal - chemistry Drugs, Chinese Herbal - isolation & purification Drugs, Chinese Herbal - pharmacology Immunosuppressive Agents - chemistry Immunosuppressive Agents - immunology Immunosuppressive Agents - isolation & purification Mice Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plant Bark - chemistry T-Lymphocytes - drug effects |
| title | Diterpenoids with Immunosuppressive Activities from Cinnamomum cassia |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T10%3A15%3A01IST&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=Diterpenoids%20with%20Immunosuppressive%20Activities%20from%20Cinnamomum%20cassia&rft.jtitle=Journal%20of%20natural%20products%20(Washington,%20D.C.)&rft.au=Zeng,%20Junfen&rft.date=2014-08-22&rft.volume=77&rft.issue=8&rft.spage=1948&rft.epage=1954&rft.pages=1948-1954&rft.issn=0163-3864&rft.eissn=1520-6025&rft_id=info:doi/10.1021/np500465g&rft_dat=%3Cproquest_cross%3E1710985928%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=1710985928&rft_id=info:pmid/25089845&rfr_iscdi=true |