Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges
Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents. Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans. The sponges were extracted in methanol-dichloromethane and their constituents were purified and charact...
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| Veröffentlicht in: | Pharmaceutical biology 2021-01, Vol.59 (1), p.573-581 |
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| creator | Heidary Jamebozorgi, Fatemeh Yousefzadi, Morteza Firuzi, Omidreza Nazemi, Melika Zare, Somayeh Chandran, Jima N. Schneider, Bernd Baldwin, Ian T. Jassbi, Amir Reza |
| description | Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents.
Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans.
The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells.
Three furanosesquiterpoids; furodysin (1), ent-furodysinin (2) and furoircin (3) and ten sterols were characterised in I. mutans, for the first time. Cholesterol (4), cholesta-5, 7-dien-3β-ol (5) and ergosterol (6) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol (7), 24-methyldesmosterol (8), campesterol (9), stigmasterol (10), γ-ergostenol (11), chondrillasterol (12) and γ-sitosterol (13) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC
50
values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC
50
= 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC
50
values = 2.3-7.8 µg/mL.
The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research. |
| doi_str_mv | 10.1080/13880209.2021.1920620 |
| format | Article |
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Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans.
The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells.
Three furanosesquiterpoids; furodysin (1), ent-furodysinin (2) and furoircin (3) and ten sterols were characterised in I. mutans, for the first time. Cholesterol (4), cholesta-5, 7-dien-3β-ol (5) and ergosterol (6) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol (7), 24-methyldesmosterol (8), campesterol (9), stigmasterol (10), γ-ergostenol (11), chondrillasterol (12) and γ-sitosterol (13) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC
50
values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC
50
= 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC
50
values = 2.3-7.8 µg/mL.
The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research.</description><identifier>ISSN: 1388-0209</identifier><identifier>EISSN: 1744-5116</identifier><identifier>DOI: 10.1080/13880209.2021.1920620</identifier><identifier>PMID: 34043935</identifier><language>eng</language><publisher>England: Taylor & Francis</publisher><subject><![CDATA[Animals ; Antineoplastic Agents - administration & dosage ; Antineoplastic Agents - isolation & purification ; Antineoplastic Agents - pharmacology ; Antitumor agents ; Breast cancer ; Breast Neoplasms - drug therapy ; Breast Neoplasms - pathology ; Cell Line, Tumor ; Cholesterol ; Colon cancer ; Colonic Neoplasms - drug therapy ; Colonic Neoplasms - pathology ; Colorectal cancer ; Colorimetry ; Column chromatography ; Cytotoxicity ; Dichloromethane ; Drug development ; Ergosterol ; Female ; Furanosesquiterpenes ; HT29 Cells ; Humans ; Inhibitory Concentration 50 ; Ircinia mutans ; Leukemia ; Leukemia - drug therapy ; Leukemia - pathology ; marine sponge ; MCF-7 Cells ; Molting ; Natural products ; Porifera - chemistry ; Sesquiterpenes - administration & dosage ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology ; Steroid hormones ; Steroids ; Steroids - administration & dosage ; Steroids - isolation & purification ; Steroids - pharmacology ; Sterols ; stigmasterol ; Summer ; Tumor cell lines ; Winter ; γ-sitosterol]]></subject><ispartof>Pharmaceutical biology, 2021-01, Vol.59 (1), p.573-581</ispartof><rights>2021 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2021</rights><rights>2021 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. This work is licensed under the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. 2021 The Author(s)</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c562t-11124f6bcdeeaa37e9209595907aaccc7c0cc4cb1623e57b41701fccf18ccdf43</citedby><cites>FETCH-LOGICAL-c562t-11124f6bcdeeaa37e9209595907aaccc7c0cc4cb1623e57b41701fccf18ccdf43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8168774/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8168774/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,2096,27481,27903,27904,53769,53771,59119,59120</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34043935$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Heidary Jamebozorgi, Fatemeh</creatorcontrib><creatorcontrib>Yousefzadi, Morteza</creatorcontrib><creatorcontrib>Firuzi, Omidreza</creatorcontrib><creatorcontrib>Nazemi, Melika</creatorcontrib><creatorcontrib>Zare, Somayeh</creatorcontrib><creatorcontrib>Chandran, Jima N.</creatorcontrib><creatorcontrib>Schneider, Bernd</creatorcontrib><creatorcontrib>Baldwin, Ian T.</creatorcontrib><creatorcontrib>Jassbi, Amir Reza</creatorcontrib><title>Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges</title><title>Pharmaceutical biology</title><addtitle>Pharm Biol</addtitle><description>Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents.
Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans.
The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells.
Three furanosesquiterpoids; furodysin (1), ent-furodysinin (2) and furoircin (3) and ten sterols were characterised in I. mutans, for the first time. Cholesterol (4), cholesta-5, 7-dien-3β-ol (5) and ergosterol (6) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol (7), 24-methyldesmosterol (8), campesterol (9), stigmasterol (10), γ-ergostenol (11), chondrillasterol (12) and γ-sitosterol (13) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC
50
values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC
50
= 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC
50
values = 2.3-7.8 µg/mL.
The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research.</description><subject>Animals</subject><subject>Antineoplastic Agents - administration & dosage</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor agents</subject><subject>Breast cancer</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Breast Neoplasms - pathology</subject><subject>Cell Line, Tumor</subject><subject>Cholesterol</subject><subject>Colon cancer</subject><subject>Colonic Neoplasms - drug therapy</subject><subject>Colonic Neoplasms - pathology</subject><subject>Colorectal cancer</subject><subject>Colorimetry</subject><subject>Column chromatography</subject><subject>Cytotoxicity</subject><subject>Dichloromethane</subject><subject>Drug development</subject><subject>Ergosterol</subject><subject>Female</subject><subject>Furanosesquiterpenes</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Ircinia mutans</subject><subject>Leukemia</subject><subject>Leukemia - drug therapy</subject><subject>Leukemia - pathology</subject><subject>marine sponge</subject><subject>MCF-7 Cells</subject><subject>Molting</subject><subject>Natural products</subject><subject>Porifera - chemistry</subject><subject>Sesquiterpenes - administration & dosage</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Steroid hormones</subject><subject>Steroids</subject><subject>Steroids - administration & dosage</subject><subject>Steroids - isolation & purification</subject><subject>Steroids - pharmacology</subject><subject>Sterols</subject><subject>stigmasterol</subject><subject>Summer</subject><subject>Tumor cell lines</subject><subject>Winter</subject><subject>γ-sitosterol</subject><issn>1388-0209</issn><issn>1744-5116</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>0YH</sourceid><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><sourceid>DOA</sourceid><recordid>eNp9kU1vEzEQhlcIREvgJ4BW4sIlweOP9fqCQFELkSpxgbPlnbWDo107tXeB_HucJq0oB-SDPfY774znqarXQFZAWvIeWNsSStSKEgorUJQ0lDypLkFyvhQAzdNyLprlUXRRvch5RwgRjInn1QXjhDPFxGW1WR-mOMXfHms3JxNitvl29pNNexui73NtQl_nEt8FLsWx3iT0wZt6nCcTcp33MWxtflk9c2bI9tV5X1Tfr6--rb8sb75-3qw_3SxRNHRaAgDlrumwt9YYJm3pXImyiDQGESUSRI4dNJRZITsOkoBDdNAi9o6zRbU5-fbR7PQ--dGkg47G67uLmLbapMnjYDXtWrSKo5Sd5KCcMoz0HB1Rtm_RyOL14eS1n7vR9mjDlMzwyPTxS_A_9Db-1C00rZTHZt6dDVK8nW2e9Ogz2mEwwcY5ayoYb4CSMuxF9fYf6S7OKZRRadooKKxAiaISJxWmmHOy7qEZIPoIXt-D10fw-gy-5L35-ycPWfeki-DjSeCDi2k0v2Iaej2ZwxCTK-DRZ83-X-MPHhy-4w</recordid><startdate>20210101</startdate><enddate>20210101</enddate><creator>Heidary Jamebozorgi, Fatemeh</creator><creator>Yousefzadi, Morteza</creator><creator>Firuzi, Omidreza</creator><creator>Nazemi, Melika</creator><creator>Zare, Somayeh</creator><creator>Chandran, Jima N.</creator><creator>Schneider, Bernd</creator><creator>Baldwin, Ian T.</creator><creator>Jassbi, Amir Reza</creator><general>Taylor & Francis</general><general>Taylor & Francis Ltd</general><general>Taylor & Francis Group</general><scope>0YH</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>8FD</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>P64</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>RC3</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20210101</creationdate><title>Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges</title><author>Heidary Jamebozorgi, Fatemeh ; Yousefzadi, Morteza ; Firuzi, Omidreza ; Nazemi, Melika ; Zare, Somayeh ; Chandran, Jima N. ; Schneider, Bernd ; Baldwin, Ian T. ; Jassbi, Amir Reza</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c562t-11124f6bcdeeaa37e9209595907aaccc7c0cc4cb1623e57b41701fccf18ccdf43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - administration & dosage</topic><topic>Antineoplastic Agents - isolation & purification</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor agents</topic><topic>Breast cancer</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Breast Neoplasms - pathology</topic><topic>Cell Line, Tumor</topic><topic>Cholesterol</topic><topic>Colon cancer</topic><topic>Colonic Neoplasms - drug therapy</topic><topic>Colonic Neoplasms - pathology</topic><topic>Colorectal cancer</topic><topic>Colorimetry</topic><topic>Column chromatography</topic><topic>Cytotoxicity</topic><topic>Dichloromethane</topic><topic>Drug development</topic><topic>Ergosterol</topic><topic>Female</topic><topic>Furanosesquiterpenes</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Ircinia mutans</topic><topic>Leukemia</topic><topic>Leukemia - drug therapy</topic><topic>Leukemia - pathology</topic><topic>marine sponge</topic><topic>MCF-7 Cells</topic><topic>Molting</topic><topic>Natural products</topic><topic>Porifera - chemistry</topic><topic>Sesquiterpenes - administration & dosage</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Steroid hormones</topic><topic>Steroids</topic><topic>Steroids - administration & dosage</topic><topic>Steroids - isolation & purification</topic><topic>Steroids - pharmacology</topic><topic>Sterols</topic><topic>stigmasterol</topic><topic>Summer</topic><topic>Tumor cell lines</topic><topic>Winter</topic><topic>γ-sitosterol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Heidary Jamebozorgi, Fatemeh</creatorcontrib><creatorcontrib>Yousefzadi, Morteza</creatorcontrib><creatorcontrib>Firuzi, Omidreza</creatorcontrib><creatorcontrib>Nazemi, Melika</creatorcontrib><creatorcontrib>Zare, Somayeh</creatorcontrib><creatorcontrib>Chandran, Jima N.</creatorcontrib><creatorcontrib>Schneider, Bernd</creatorcontrib><creatorcontrib>Baldwin, Ian T.</creatorcontrib><creatorcontrib>Jassbi, Amir Reza</creatorcontrib><collection>Taylor & Francis Open Access</collection><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>Technology Research Database</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>Engineering Research Database</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>Biotechnology and BioEngineering Abstracts</collection><collection>Publicly Available Content Database</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>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Pharmaceutical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Heidary Jamebozorgi, Fatemeh</au><au>Yousefzadi, Morteza</au><au>Firuzi, Omidreza</au><au>Nazemi, Melika</au><au>Zare, Somayeh</au><au>Chandran, Jima N.</au><au>Schneider, Bernd</au><au>Baldwin, Ian T.</au><au>Jassbi, Amir Reza</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges</atitle><jtitle>Pharmaceutical biology</jtitle><addtitle>Pharm Biol</addtitle><date>2021-01-01</date><risdate>2021</risdate><volume>59</volume><issue>1</issue><spage>573</spage><epage>581</epage><pages>573-581</pages><issn>1388-0209</issn><eissn>1744-5116</eissn><abstract>Ircinia mutans Wilson (Irciniidae) is a sponge with antimicrobial and cytotoxic constituents.
Our objective was to characterise the cytotoxic constituents of two seasonal collections of I. mutans.
The sponges were extracted in methanol-dichloromethane and their constituents were purified and characterised using column chromatography, GC-MS, 1 D and 2 D NMR. Anti-proliferative activities of the compounds, were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay (0.25-100 μg/mL, 72 h) against leukaemia (MOLT-4), breast (MCF-7) and colon cancer (HT-29) human cells.
Three furanosesquiterpoids; furodysin (1), ent-furodysinin (2) and furoircin (3) and ten sterols were characterised in I. mutans, for the first time. Cholesterol (4), cholesta-5, 7-dien-3β-ol (5) and ergosterol (6) were determined in the sponge from the winter collections, while cholesta-5, 22-dien-3β-ol (7), 24-methyldesmosterol (8), campesterol (9), stigmasterol (10), γ-ergostenol (11), chondrillasterol (12) and γ-sitosterol (13) were detected in the summer samples. The steroids from the winter collection exhibited cytotoxic activity with IC
50
values of 13.0 ± 0.9, 11.1 ± 1.7 and 1.1 ± 0.4 µg/mL, against the mentioned cancer cell lines, respectively, while those from the summer sample, showed greater activity, IC
50
= 1.1 ± 0.2 μg/mL against MOLT-4. The purified steroids showed potent MOLT-4 cytotoxic activity, IC
50
values = 2.3-7.8 µg/mL.
The present study suggests that I. mutans is a rich source of cytotoxic steroids, and introduces 3 as new natural product. Considering the high cytotoxic activity of the steroids, these structures could be candidates for anticancer drug development in future research.</abstract><cop>England</cop><pub>Taylor & Francis</pub><pmid>34043935</pmid><doi>10.1080/13880209.2021.1920620</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Pharmaceutical biology, 2021-01, Vol.59 (1), p.573-581 |
| issn | 1388-0209 1744-5116 |
| language | eng |
| recordid | cdi_proquest_journals_2691138195 |
| source | Taylor & Francis Open Access; MEDLINE; DOAJ Directory of Open Access Journals; PubMed Central; Alma/SFX Local Collection |
| subjects | Animals Antineoplastic Agents - administration & dosage Antineoplastic Agents - isolation & purification Antineoplastic Agents - pharmacology Antitumor agents Breast cancer Breast Neoplasms - drug therapy Breast Neoplasms - pathology Cell Line, Tumor Cholesterol Colon cancer Colonic Neoplasms - drug therapy Colonic Neoplasms - pathology Colorectal cancer Colorimetry Column chromatography Cytotoxicity Dichloromethane Drug development Ergosterol Female Furanosesquiterpenes HT29 Cells Humans Inhibitory Concentration 50 Ircinia mutans Leukemia Leukemia - drug therapy Leukemia - pathology marine sponge MCF-7 Cells Molting Natural products Porifera - chemistry Sesquiterpenes - administration & dosage Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology Steroid hormones Steroids Steroids - administration & dosage Steroids - isolation & purification Steroids - pharmacology Sterols stigmasterol Summer Tumor cell lines Winter γ-sitosterol |
| title | Cytotoxic furanosesquiterpenoids and steroids from Ircinia mutans sponges |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T15%3A47%3A09IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Cytotoxic%20furanosesquiterpenoids%20and%20steroids%20from%20Ircinia%20mutans%20sponges&rft.jtitle=Pharmaceutical%20biology&rft.au=Heidary%20Jamebozorgi,%20Fatemeh&rft.date=2021-01-01&rft.volume=59&rft.issue=1&rft.spage=573&rft.epage=581&rft.pages=573-581&rft.issn=1388-0209&rft.eissn=1744-5116&rft_id=info:doi/10.1080/13880209.2021.1920620&rft_dat=%3Cproquest_doaj_%3E2534612039%3C/proquest_doaj_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2691138195&rft_id=info:pmid/34043935&rft_doaj_id=oai_doaj_org_article_2b8ce94c77b7419f9a30d4cf09ed8ca7&rfr_iscdi=true |