New erythritol derivatives from the fertile form of Roccella montagnei
Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical str...
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| Veröffentlicht in: | Phytochemistry (Oxford) 2017-05, Vol.137, p.156-164 |
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| creator | Duong, Thuc Huy Huynh, Bui Linh Chi Chavasiri, Warinthorn Chollet-Krugler, Marylene Nguyen, Van Kieu Nguyen, Thi Hoai Thu Hansen, Poul Erik Le Pogam, Pierre Thüs, Holger Boustie, Joël Nguyen, Kim Phi Phung |
| description | Chemical investigation of the methanol extract of the fertile form of Roccella montagnei collected in Vietnam afforded twelve secondary metabolites, including five new montagnetol derivatives, orsellinylmontagnetols A-D and a furanyl derivative together with seven known compounds. Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC
value of 68.39 ± 3.46 μM. |
| doi_str_mv | 10.1016/j.phytochem.2017.02.012 |
| format | Article |
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value of 68.39 ± 3.46 μM.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - isolation & purification</subject><subject>Ascomycota - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Chemical Sciences</subject><subject>Erythritol - analogs & derivatives</subject><subject>Erythritol - chemistry</subject><subject>Erythritol - isolation & purification</subject><subject>Humans</subject><subject>Lichens - chemistry</subject><subject>Molecular Structure</subject><subject>Salicylates - chemistry</subject><subject>Salicylates - isolation & purification</subject><subject>Vietnam</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kE1PwkAQhjdGI4j-Be1RD62zH-22R0JETIgmRs-bpczakpbF3QXDv7cV5PQmk2fmnTyE3FFIKNDscZVsqn2wZYVtwoDKBFgClJ2RIc0lj7kEOCdDAE7jQjA2IFferwAgTbPskgxYzhjLCxiS6Sv-ROj2oXJ1sE20RFfvdKh36CPjbBuFCiODLtRNl9a1kTXRuy1LbBodtXYd9Nca62tyYXTj8eaYI_I5ffqYzOL52_PLZDyPS15kIWZC5NrwPDVoug9YZpYcqZAUsYSFWDAml4UWMmVGIhclmA4zVPJCCuCc8hF5ONytdKM2rm612yurazUbz1U_A5p2HjKx69n7A7tx9nuLPqi29n9_r9FuvepMQZFnkMoOlQe0dNZ7h-Z0m4LqhauVOglXvXAFrOti3ebtsWS7aHF52vs3zH8BGk1-Mg</recordid><startdate>201705</startdate><enddate>201705</enddate><creator>Duong, Thuc Huy</creator><creator>Huynh, Bui Linh Chi</creator><creator>Chavasiri, Warinthorn</creator><creator>Chollet-Krugler, Marylene</creator><creator>Nguyen, Van Kieu</creator><creator>Nguyen, Thi Hoai Thu</creator><creator>Hansen, Poul Erik</creator><creator>Le Pogam, Pierre</creator><creator>Thüs, Holger</creator><creator>Boustie, Joël</creator><creator>Nguyen, Kim Phi Phung</creator><general>Elsevier</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><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-3936-3859</orcidid><orcidid>https://orcid.org/0000-0002-3351-4708</orcidid></search><sort><creationdate>201705</creationdate><title>New erythritol derivatives from the fertile form of Roccella montagnei</title><author>Duong, Thuc Huy ; 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Their chemical structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The relative stereochemistry of two chiral centers (C-2 and C-3) of orsellinylmontagnetols A and B was elucidated by comparison of their coupling constants and the specific rotation with those reported in the literature while the absolute stereochemistry was determined by the application of a modified Mosher method for the hydroxy group at C-3. The absolute configuration (2R,3S) of the butanetetraol moiety of these compounds is in accordance with that of erythrin, a recognized chemotaxonomic marker of the genus Roccella. Five of these compounds were evaluated for their cytotoxic activities against four cancer cell lines. Only orsellinylmontagnetol A exerted a moderate activity against MCF-7 cell line with an IC
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| subjects | Antineoplastic Agents - chemistry Antineoplastic Agents - isolation & purification Ascomycota - chemistry Cell Line, Tumor Chemical Sciences Erythritol - analogs & derivatives Erythritol - chemistry Erythritol - isolation & purification Humans Lichens - chemistry Molecular Structure Salicylates - chemistry Salicylates - isolation & purification Vietnam |
| title | New erythritol derivatives from the fertile form of Roccella montagnei |
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