Antiviral activity of sulphated specialized metabolites from sea urchin Clypeaster humilis : in vitro and in silico studies
Chemical investigations of the sea urchin has led to separation of twelve compounds including one new sulfonic acid derivative (7 ) tridec-1-en-7-yl hydrogen sulphate (1), first isolated from natural source, pyridine-3-yl methane sulfonate (2), and first isolated from marine organisms, boldine (12),...
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| creator | Abdelkarem, Fahd M Assaf, Hamdy K Mostafa, Yaser A Mahdy, Aldoushy Hussein, Modather F Ross, Samir A Mohamed, Nesma M |
| description | Chemical investigations of the sea urchin
has led to separation of twelve compounds including one new sulfonic acid derivative (7
) tridec-1-en-7-yl hydrogen sulphate (1), first isolated from natural source, pyridine-3-yl methane sulfonate (2), and first isolated from marine organisms, boldine (12), in addition to nine known compounds (3-11), which were isolated for the first time from the genus Clypeaster. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR), HR-ESI-MS as well as comparison with the previously reported data. The antiviral activity of the crude extract and sulphated compounds were evaluated using MTT colorimetric assay against Coxsackie B4 virus. The crude extract and compound 1 showed very potent antiviral activity with a percentage of inhibition equal to 89.7 ± 0.53% and 86.1 ± 0.92%, respectively. Results of the molecular docking analysis of the isolated compounds within Coxsackie Virus B4 (COX-B4) X-ray crystal structure and quantum chemical calculation for three sulphated compounds are in a consistent adaptation with the
antiviral results. The pharmacokinetic properties (ADME) of isolated compounds were determined. |
| doi_str_mv | 10.1039/d4ra01966k |
| format | Article |
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has led to separation of twelve compounds including one new sulfonic acid derivative (7
) tridec-1-en-7-yl hydrogen sulphate (1), first isolated from natural source, pyridine-3-yl methane sulfonate (2), and first isolated from marine organisms, boldine (12), in addition to nine known compounds (3-11), which were isolated for the first time from the genus Clypeaster. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR), HR-ESI-MS as well as comparison with the previously reported data. The antiviral activity of the crude extract and sulphated compounds were evaluated using MTT colorimetric assay against Coxsackie B4 virus. The crude extract and compound 1 showed very potent antiviral activity with a percentage of inhibition equal to 89.7 ± 0.53% and 86.1 ± 0.92%, respectively. Results of the molecular docking analysis of the isolated compounds within Coxsackie Virus B4 (COX-B4) X-ray crystal structure and quantum chemical calculation for three sulphated compounds are in a consistent adaptation with the
antiviral results. The pharmacokinetic properties (ADME) of isolated compounds were determined.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d4ra01966k</identifier><identifier>PMID: 38690113</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemistry ; Crystal structure ; Metabolites ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Quantum chemistry ; Sulfonic acid ; Two dimensional analysis</subject><ispartof>RSC advances, 2024-04, Vol.14 (20), p.14185-14193</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2024</rights><rights>This journal is © The Royal Society of Chemistry 2024 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c366t-5dcbf90f6d5a0741ca9b2815503920b6fa3c9713111ac1e79cc5d402129fe57a3</cites><orcidid>0000-0002-9700-8724 ; 0000-0002-6388-0821 ; 0000-0002-3807-1299 ; 0000-0001-8357-6942 ; 0000-0002-9845-0020</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11058476/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC11058476/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38690113$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Abdelkarem, Fahd M</creatorcontrib><creatorcontrib>Assaf, Hamdy K</creatorcontrib><creatorcontrib>Mostafa, Yaser A</creatorcontrib><creatorcontrib>Mahdy, Aldoushy</creatorcontrib><creatorcontrib>Hussein, Modather F</creatorcontrib><creatorcontrib>Ross, Samir A</creatorcontrib><creatorcontrib>Mohamed, Nesma M</creatorcontrib><title>Antiviral activity of sulphated specialized metabolites from sea urchin Clypeaster humilis : in vitro and in silico studies</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>Chemical investigations of the sea urchin
has led to separation of twelve compounds including one new sulfonic acid derivative (7
) tridec-1-en-7-yl hydrogen sulphate (1), first isolated from natural source, pyridine-3-yl methane sulfonate (2), and first isolated from marine organisms, boldine (12), in addition to nine known compounds (3-11), which were isolated for the first time from the genus Clypeaster. Their structures were elucidated based on spectroscopic analyses (1D and 2D NMR), HR-ESI-MS as well as comparison with the previously reported data. The antiviral activity of the crude extract and sulphated compounds were evaluated using MTT colorimetric assay against Coxsackie B4 virus. The crude extract and compound 1 showed very potent antiviral activity with a percentage of inhibition equal to 89.7 ± 0.53% and 86.1 ± 0.92%, respectively. Results of the molecular docking analysis of the isolated compounds within Coxsackie Virus B4 (COX-B4) X-ray crystal structure and quantum chemical calculation for three sulphated compounds are in a consistent adaptation with the
antiviral results. The pharmacokinetic properties (ADME) of isolated compounds were determined.</description><subject>Chemistry</subject><subject>Crystal structure</subject><subject>Metabolites</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Quantum chemistry</subject><subject>Sulfonic acid</subject><subject>Two dimensional analysis</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkVFrFDEUhYNYbGn74g-QgC9SWJs7mWQmvsiy2losCKLP4U4m46ZmJmOSKaz-ebO2lmpecnLzcTiHS8hzYK-BcXXe1xEZKCm_PyFHFavlqmJSPX2kD8lpSjesHCmgkvCMHPJWKgbAj8iv9ZTdrYvoKZq9yjsaBpoWP28x256m2RqH3v0serQZu-BdtokOMYw0WaRLNFs30Y3fzRZTtpFul9F5l-gbWubFMQaKU79_pDI3gaa89M6mE3IwoE_29P4-Jl8v3n_ZfFhdf7q82qyvV4ZLmVeiN92g2CB7gaypwaDqqhaEKPUr1skBuVENcABAA7ZRxoi-ZhVUarCiQX5M3t75zks32t7YKZe-eo5uxLjTAZ3-92dyW_0t3GoAJtq6kcXh1b1DDD8Wm7IeXTLWe5xsWJLmrC4J2gp4QV_-h96EJU6lX6EEB6bqVhXq7I4yMaQU7fCQBpje71W_qz-v_-z1Y4FfPM7_gP7dIv8NCNqfqA</recordid><startdate>20240425</startdate><enddate>20240425</enddate><creator>Abdelkarem, Fahd M</creator><creator>Assaf, Hamdy K</creator><creator>Mostafa, Yaser A</creator><creator>Mahdy, Aldoushy</creator><creator>Hussein, Modather F</creator><creator>Ross, Samir A</creator><creator>Mohamed, Nesma M</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-9700-8724</orcidid><orcidid>https://orcid.org/0000-0002-6388-0821</orcidid><orcidid>https://orcid.org/0000-0002-3807-1299</orcidid><orcidid>https://orcid.org/0000-0001-8357-6942</orcidid><orcidid>https://orcid.org/0000-0002-9845-0020</orcidid></search><sort><creationdate>20240425</creationdate><title>Antiviral activity of sulphated specialized metabolites from sea urchin Clypeaster humilis : in vitro and in silico studies</title><author>Abdelkarem, Fahd M ; Assaf, Hamdy K ; Mostafa, Yaser A ; Mahdy, Aldoushy ; Hussein, Modather F ; Ross, Samir A ; Mohamed, Nesma M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c366t-5dcbf90f6d5a0741ca9b2815503920b6fa3c9713111ac1e79cc5d402129fe57a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Chemistry</topic><topic>Crystal structure</topic><topic>Metabolites</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Quantum chemistry</topic><topic>Sulfonic acid</topic><topic>Two dimensional analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Abdelkarem, Fahd M</creatorcontrib><creatorcontrib>Assaf, Hamdy K</creatorcontrib><creatorcontrib>Mostafa, Yaser A</creatorcontrib><creatorcontrib>Mahdy, Aldoushy</creatorcontrib><creatorcontrib>Hussein, Modather F</creatorcontrib><creatorcontrib>Ross, Samir A</creatorcontrib><creatorcontrib>Mohamed, Nesma M</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Abdelkarem, Fahd M</au><au>Assaf, Hamdy K</au><au>Mostafa, Yaser A</au><au>Mahdy, Aldoushy</au><au>Hussein, Modather F</au><au>Ross, Samir A</au><au>Mohamed, Nesma M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antiviral activity of sulphated specialized metabolites from sea urchin Clypeaster humilis : in vitro and in silico studies</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2024-04-25</date><risdate>2024</risdate><volume>14</volume><issue>20</issue><spage>14185</spage><epage>14193</epage><pages>14185-14193</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>Chemical investigations of the sea urchin
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central; PubMed Central Open Access |
| subjects | Chemistry Crystal structure Metabolites Molecular docking NMR Nuclear magnetic resonance Quantum chemistry Sulfonic acid Two dimensional analysis |
| title | Antiviral activity of sulphated specialized metabolites from sea urchin Clypeaster humilis : in vitro and in silico studies |
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