Marine Bioactive Steryl Esters from the Red Sea Black Coral Antipathes dichotoma
Two new marine steryl hexadecanoates, 3β‐hexadecanoylcholest‐5‐en‐7‐one (1) and 3β‐hexadecanoylcholest‐5‐en‐7β‐ol (2), along with seven known compounds, cholest‐5‐en‐3β‐yl‐formate (3), thymidine (4), indole‐3‐carboxaldehyde (5), 3β‐hydroxycholest‐5‐en‐7‐one (6), cholesterol (7), 22‐dehydrocholestrol...
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creator | Alarif, Walied M. Abdel-lateff, Ahmed AL-lihaibi, Sultan S. Ayyad, Seif-Eldin N. Badria, Farid A. Alsofyani, Abdulmohsin A. Abou-Elnaga, Zeinab S. |
description | Two new marine steryl hexadecanoates, 3β‐hexadecanoylcholest‐5‐en‐7‐one (1) and 3β‐hexadecanoylcholest‐5‐en‐7β‐ol (2), along with seven known compounds, cholest‐5‐en‐3β‐yl‐formate (3), thymidine (4), indole‐3‐carboxaldehyde (5), 3β‐hydroxycholest‐5‐en‐7‐one (6), cholesterol (7), 22‐dehydrocholestrol (8), and 24‐methylenecholesterol (9), were isolated from the anthozoan black coral, Antipathes dichotoma. The structures of all isolated compounds were determined by interpretation of their spectral data 1D (1H, 13C and DEPT) and 2D (COSY, HSQC and HMBC) NMR, UV, IR, and MS. Compounds 1–5 were evaluated for their anticancer activities, employing four cancer panels; HepG2, WI 38, VERO, and MCF‐7. All tested compounds, except 4, showed moderate activities. Compound 4 exhibited significant anticancer activity against VERO and MCF‐7, with IC50 20.5 and 20.2 µg/mL, respectively.
Antipathes dichotoma is a source of several secondary metabolites; most of them were already isolated from, e.g., sponges, octocorallia, and macro‐algae. The spreading of these metabolites in the macro‐organisms (marine invertebrates) strongly indicates that dietary or symbiotic micro‐organisms are involved in the production of these isolates. |
doi_str_mv | 10.1002/clen.201200409 |
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Antipathes dichotoma is a source of several secondary metabolites; most of them were already isolated from, e.g., sponges, octocorallia, and macro‐algae. The spreading of these metabolites in the macro‐organisms (marine invertebrates) strongly indicates that dietary or symbiotic micro‐organisms are involved in the production of these isolates.</description><identifier>ISSN: 1863-0650</identifier><identifier>EISSN: 1863-0669</identifier><identifier>DOI: 10.1002/clen.201200409</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkaloids ; Antipathes ; Cytotoxicity ; Hexacorallia ; Marine ; Octocorallia ; Steroids</subject><ispartof>Clean : soil, air, water, 2013-11, Vol.41 (11), p.1116-1121</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3889-90af0069373dddb4e101108b5e64d8c1f99e75dc831a7bcbcbfb1176c1300dfd3</citedby><cites>FETCH-LOGICAL-c3889-90af0069373dddb4e101108b5e64d8c1f99e75dc831a7bcbcbfb1176c1300dfd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fclen.201200409$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fclen.201200409$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Alarif, Walied M.</creatorcontrib><creatorcontrib>Abdel-lateff, Ahmed</creatorcontrib><creatorcontrib>AL-lihaibi, Sultan S.</creatorcontrib><creatorcontrib>Ayyad, Seif-Eldin N.</creatorcontrib><creatorcontrib>Badria, Farid A.</creatorcontrib><creatorcontrib>Alsofyani, Abdulmohsin A.</creatorcontrib><creatorcontrib>Abou-Elnaga, Zeinab S.</creatorcontrib><title>Marine Bioactive Steryl Esters from the Red Sea Black Coral Antipathes dichotoma</title><title>Clean : soil, air, water</title><addtitle>Clean Soil Air Water</addtitle><description>Two new marine steryl hexadecanoates, 3β‐hexadecanoylcholest‐5‐en‐7‐one (1) and 3β‐hexadecanoylcholest‐5‐en‐7β‐ol (2), along with seven known compounds, cholest‐5‐en‐3β‐yl‐formate (3), thymidine (4), indole‐3‐carboxaldehyde (5), 3β‐hydroxycholest‐5‐en‐7‐one (6), cholesterol (7), 22‐dehydrocholestrol (8), and 24‐methylenecholesterol (9), were isolated from the anthozoan black coral, Antipathes dichotoma. The structures of all isolated compounds were determined by interpretation of their spectral data 1D (1H, 13C and DEPT) and 2D (COSY, HSQC and HMBC) NMR, UV, IR, and MS. Compounds 1–5 were evaluated for their anticancer activities, employing four cancer panels; HepG2, WI 38, VERO, and MCF‐7. All tested compounds, except 4, showed moderate activities. Compound 4 exhibited significant anticancer activity against VERO and MCF‐7, with IC50 20.5 and 20.2 µg/mL, respectively.
Antipathes dichotoma is a source of several secondary metabolites; most of them were already isolated from, e.g., sponges, octocorallia, and macro‐algae. The spreading of these metabolites in the macro‐organisms (marine invertebrates) strongly indicates that dietary or symbiotic micro‐organisms are involved in the production of these isolates.</description><subject>Alkaloids</subject><subject>Antipathes</subject><subject>Cytotoxicity</subject><subject>Hexacorallia</subject><subject>Marine</subject><subject>Octocorallia</subject><subject>Steroids</subject><issn>1863-0650</issn><issn>1863-0669</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkEFP2zAUgKNpSOsK150tcdkl5b06duIjRF2H1hVEYZN2sVzbEYY0LnYK67-fq6IK7YJ8eJb8fdbTl2VfEEYIMD7Tre1GY8AxQAHiQzbAitMcOBcfD3cGn7LPMT4AcECOg-z6pwqus-TCeaV792zJordh25JJTDOSJvgV6e8tubGGLKwiF63Sj6T2QbXkvOvdWqXXSIzT9773K3WcHTWqjfbkdQ6zu2-T2_p7PruaXtbns1zTqhK5ANWkJQQtqTFmWVgERKiWzPLCVBobIWzJjK4oqnKp02mWiCXXSAFMY-gw-7r_dx3808bGXq5c1LZtVWf9JkoseMGAMRQJPf0PffCb0KXtEsVSB2CUJ2q0p3TwMQbbyHVwKxW2EkHuAstdYHkInASxF15ca7fv0LKeTeZv3XzvupT578FV4VHykpZM_p5P5Y96gdNf4o-c039i441B</recordid><startdate>201311</startdate><enddate>201311</enddate><creator>Alarif, Walied M.</creator><creator>Abdel-lateff, Ahmed</creator><creator>AL-lihaibi, Sultan S.</creator><creator>Ayyad, Seif-Eldin N.</creator><creator>Badria, Farid A.</creator><creator>Alsofyani, Abdulmohsin A.</creator><creator>Abou-Elnaga, Zeinab S.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QH</scope><scope>7ST</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>L.G</scope><scope>SOI</scope><scope>7TN</scope><scope>7U6</scope><scope>M7N</scope></search><sort><creationdate>201311</creationdate><title>Marine Bioactive Steryl Esters from the Red Sea Black Coral Antipathes dichotoma</title><author>Alarif, Walied M. ; Abdel-lateff, Ahmed ; AL-lihaibi, Sultan S. ; Ayyad, Seif-Eldin N. ; Badria, Farid A. ; Alsofyani, Abdulmohsin A. ; Abou-Elnaga, Zeinab S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3889-90af0069373dddb4e101108b5e64d8c1f99e75dc831a7bcbcbfb1176c1300dfd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkaloids</topic><topic>Antipathes</topic><topic>Cytotoxicity</topic><topic>Hexacorallia</topic><topic>Marine</topic><topic>Octocorallia</topic><topic>Steroids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Alarif, Walied M.</creatorcontrib><creatorcontrib>Abdel-lateff, Ahmed</creatorcontrib><creatorcontrib>AL-lihaibi, Sultan S.</creatorcontrib><creatorcontrib>Ayyad, Seif-Eldin N.</creatorcontrib><creatorcontrib>Badria, Farid A.</creatorcontrib><creatorcontrib>Alsofyani, Abdulmohsin A.</creatorcontrib><creatorcontrib>Abou-Elnaga, Zeinab S.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Aqualine</collection><collection>Environment Abstracts</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Environment Abstracts</collection><collection>Oceanic Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><jtitle>Clean : soil, air, water</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Alarif, Walied M.</au><au>Abdel-lateff, Ahmed</au><au>AL-lihaibi, Sultan S.</au><au>Ayyad, Seif-Eldin N.</au><au>Badria, Farid A.</au><au>Alsofyani, Abdulmohsin A.</au><au>Abou-Elnaga, Zeinab S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Marine Bioactive Steryl Esters from the Red Sea Black Coral Antipathes dichotoma</atitle><jtitle>Clean : soil, air, water</jtitle><addtitle>Clean Soil Air Water</addtitle><date>2013-11</date><risdate>2013</risdate><volume>41</volume><issue>11</issue><spage>1116</spage><epage>1121</epage><pages>1116-1121</pages><issn>1863-0650</issn><eissn>1863-0669</eissn><abstract>Two new marine steryl hexadecanoates, 3β‐hexadecanoylcholest‐5‐en‐7‐one (1) and 3β‐hexadecanoylcholest‐5‐en‐7β‐ol (2), along with seven known compounds, cholest‐5‐en‐3β‐yl‐formate (3), thymidine (4), indole‐3‐carboxaldehyde (5), 3β‐hydroxycholest‐5‐en‐7‐one (6), cholesterol (7), 22‐dehydrocholestrol (8), and 24‐methylenecholesterol (9), were isolated from the anthozoan black coral, Antipathes dichotoma. The structures of all isolated compounds were determined by interpretation of their spectral data 1D (1H, 13C and DEPT) and 2D (COSY, HSQC and HMBC) NMR, UV, IR, and MS. Compounds 1–5 were evaluated for their anticancer activities, employing four cancer panels; HepG2, WI 38, VERO, and MCF‐7. All tested compounds, except 4, showed moderate activities. Compound 4 exhibited significant anticancer activity against VERO and MCF‐7, with IC50 20.5 and 20.2 µg/mL, respectively.
Antipathes dichotoma is a source of several secondary metabolites; most of them were already isolated from, e.g., sponges, octocorallia, and macro‐algae. The spreading of these metabolites in the macro‐organisms (marine invertebrates) strongly indicates that dietary or symbiotic micro‐organisms are involved in the production of these isolates.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/clen.201200409</doi><tpages>6</tpages></addata></record> |
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subjects | Alkaloids Antipathes Cytotoxicity Hexacorallia Marine Octocorallia Steroids |
title | Marine Bioactive Steryl Esters from the Red Sea Black Coral Antipathes dichotoma |
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