Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B
Three carbamidocyclophanes, A, F and V, and carbamidocylindrofridin A were isolated from the cultured freshwater cyanobacterium Cylindrospermum stagnale, collected in the Canary Islands. The chemical structures of these compounds were elucidated through NMR, HRMS and ECD spectroscopy. The absolute c...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2020-12, Vol.180, p.112529-112529, Article 112529 |
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| container_title | Phytochemistry (Oxford) |
| container_volume | 180 |
| creator | Pérez, Víctor Tena Ticona, Luis Apaza Cabanillas, Alfredo H. Corral, Santiago Maderuelo Perles, Josefina Valencia, Diego Fernando Rosero Quintana, Antera Martel Domenech, Montserrat Ortega Sánchez, Ángel Rumbero |
| description | Three carbamidocyclophanes, A, F and V, and carbamidocylindrofridin A were isolated from the cultured freshwater cyanobacterium Cylindrospermum stagnale, collected in the Canary Islands. The chemical structures of these compounds were elucidated through NMR, HRMS and ECD spectroscopy. The absolute configuration of carbamidocyclophane A was confirmed using X-ray-diffraction. All compounds showed apoptotic capacity against the SK-MEL-1, SK-MEL-28 and SK-MEL-31 tumour cells. Carbamidocylindrofridin A had the highest anti-tumour potential, with an IC50 of 1 ± 0.3 μM in the SK-MEL-1 cell line.
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•An unknown carbamidocyclophane and a cylindrofridin were isolated from C. stagnale.•Absolute configurations were elucidated by crystal diffraction and ECD.•Compounds showed apoptotic capacity against human malignant melanoma cells. |
| doi_str_mv | 10.1016/j.phytochem.2020.112529 |
| format | Article |
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[Display omitted]
•An unknown carbamidocyclophane and a cylindrofridin were isolated from C. stagnale.•Absolute configurations were elucidated by crystal diffraction and ECD.•Compounds showed apoptotic capacity against human malignant melanoma cells.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2020.112529</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Anti-tumour ; Carbamidocyclophane ; Carbamidocylindrofridin ; Cyanobacterium ; Cylindrospermum stagnale ; Nostocaceae</subject><ispartof>Phytochemistry (Oxford), 2020-12, Vol.180, p.112529-112529, Article 112529</ispartof><rights>2020 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c397t-d2b36269c86756c4d7f432f9c69bd654402e995d223d1d93d3b1119960b50fa3</citedby><cites>FETCH-LOGICAL-c397t-d2b36269c86756c4d7f432f9c69bd654402e995d223d1d93d3b1119960b50fa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2020.112529$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Pérez, Víctor Tena</creatorcontrib><creatorcontrib>Ticona, Luis Apaza</creatorcontrib><creatorcontrib>Cabanillas, Alfredo H.</creatorcontrib><creatorcontrib>Corral, Santiago Maderuelo</creatorcontrib><creatorcontrib>Perles, Josefina</creatorcontrib><creatorcontrib>Valencia, Diego Fernando Rosero</creatorcontrib><creatorcontrib>Quintana, Antera Martel</creatorcontrib><creatorcontrib>Domenech, Montserrat Ortega</creatorcontrib><creatorcontrib>Sánchez, Ángel Rumbero</creatorcontrib><title>Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B</title><title>Phytochemistry (Oxford)</title><description>Three carbamidocyclophanes, A, F and V, and carbamidocylindrofridin A were isolated from the cultured freshwater cyanobacterium Cylindrospermum stagnale, collected in the Canary Islands. The chemical structures of these compounds were elucidated through NMR, HRMS and ECD spectroscopy. The absolute configuration of carbamidocyclophane A was confirmed using X-ray-diffraction. All compounds showed apoptotic capacity against the SK-MEL-1, SK-MEL-28 and SK-MEL-31 tumour cells. Carbamidocylindrofridin A had the highest anti-tumour potential, with an IC50 of 1 ± 0.3 μM in the SK-MEL-1 cell line.
[Display omitted]
•An unknown carbamidocyclophane and a cylindrofridin were isolated from C. stagnale.•Absolute configurations were elucidated by crystal diffraction and ECD.•Compounds showed apoptotic capacity against human malignant melanoma cells.</description><subject>Anti-tumour</subject><subject>Carbamidocyclophane</subject><subject>Carbamidocylindrofridin</subject><subject>Cyanobacterium</subject><subject>Cylindrospermum stagnale</subject><subject>Nostocaceae</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFUclOwzAUtBBIlMI34COXFC-Jg49pxSZV4sLdcuwX6iqJg-0i5Sv4ZYyKEDdOb5sZvdEgdE3JihIqbveraTcnb3YwrBhheUtZxeQJWtC7mhe8JuQULQjhtJAlY-foIsY9IaSqhFigz2ZMLh0GH3SPJ58gj7nzHTY6tHpw1pvZ9H7a6REi1qP9e-jdaIPvgrNuxA120fc6gcVd8ANOO8Bm1qNvtUkQ3GHAmx9GnCAMeY5Jv426B7y-bzARpFpforNO9xGufuoSvT7cv26eiu3L4_Om2RaGyzoVlrVcMCHNnagrYUpbdyVnnTRCtlZUZUkYSFlZxrilVnLLW0qplIK0Fek0X6Kbo-wU_PsBYlKDiwb6Prv0h6hYWWa6EEJmaH2Emvx3DNCpKbhBh1lRor4TUHv1m4D6TkAdE8jM5siEbOTDQVDROBgNWBfAJGW9-1fjCxBTllM</recordid><startdate>202012</startdate><enddate>202012</enddate><creator>Pérez, Víctor Tena</creator><creator>Ticona, Luis Apaza</creator><creator>Cabanillas, Alfredo H.</creator><creator>Corral, Santiago Maderuelo</creator><creator>Perles, Josefina</creator><creator>Valencia, Diego Fernando Rosero</creator><creator>Quintana, Antera Martel</creator><creator>Domenech, Montserrat Ortega</creator><creator>Sánchez, Ángel Rumbero</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>202012</creationdate><title>Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B</title><author>Pérez, Víctor Tena ; Ticona, Luis Apaza ; Cabanillas, Alfredo H. ; Corral, Santiago Maderuelo ; Perles, Josefina ; Valencia, Diego Fernando Rosero ; Quintana, Antera Martel ; Domenech, Montserrat Ortega ; Sánchez, Ángel Rumbero</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c397t-d2b36269c86756c4d7f432f9c69bd654402e995d223d1d93d3b1119960b50fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Anti-tumour</topic><topic>Carbamidocyclophane</topic><topic>Carbamidocylindrofridin</topic><topic>Cyanobacterium</topic><topic>Cylindrospermum stagnale</topic><topic>Nostocaceae</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pérez, Víctor Tena</creatorcontrib><creatorcontrib>Ticona, Luis Apaza</creatorcontrib><creatorcontrib>Cabanillas, Alfredo H.</creatorcontrib><creatorcontrib>Corral, Santiago Maderuelo</creatorcontrib><creatorcontrib>Perles, Josefina</creatorcontrib><creatorcontrib>Valencia, Diego Fernando Rosero</creatorcontrib><creatorcontrib>Quintana, Antera Martel</creatorcontrib><creatorcontrib>Domenech, Montserrat Ortega</creatorcontrib><creatorcontrib>Sánchez, Ángel Rumbero</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pérez, Víctor Tena</au><au>Ticona, Luis Apaza</au><au>Cabanillas, Alfredo H.</au><au>Corral, Santiago Maderuelo</au><au>Perles, Josefina</au><au>Valencia, Diego Fernando Rosero</au><au>Quintana, Antera Martel</au><au>Domenech, Montserrat Ortega</au><au>Sánchez, Ángel Rumbero</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B</atitle><jtitle>Phytochemistry (Oxford)</jtitle><date>2020-12</date><risdate>2020</risdate><volume>180</volume><spage>112529</spage><epage>112529</epage><pages>112529-112529</pages><artnum>112529</artnum><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Three carbamidocyclophanes, A, F and V, and carbamidocylindrofridin A were isolated from the cultured freshwater cyanobacterium Cylindrospermum stagnale, collected in the Canary Islands. The chemical structures of these compounds were elucidated through NMR, HRMS and ECD spectroscopy. The absolute configuration of carbamidocyclophane A was confirmed using X-ray-diffraction. All compounds showed apoptotic capacity against the SK-MEL-1, SK-MEL-28 and SK-MEL-31 tumour cells. Carbamidocylindrofridin A had the highest anti-tumour potential, with an IC50 of 1 ± 0.3 μM in the SK-MEL-1 cell line.
[Display omitted]
•An unknown carbamidocyclophane and a cylindrofridin were isolated from C. stagnale.•Absolute configurations were elucidated by crystal diffraction and ECD.•Compounds showed apoptotic capacity against human malignant melanoma cells.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.phytochem.2020.112529</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record> |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Anti-tumour Carbamidocyclophane Carbamidocylindrofridin Cyanobacterium Cylindrospermum stagnale Nostocaceae |
| title | Antitumoral potential of carbamidocyclophanes and carbamidocylindrofridin A isolated from the cyanobacterium Cylindrospermum stagnale BEA 0605B |
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