Two new pterocarpans and a new pyrone derivative with cytotoxic activities from Ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone

Background Ptycholobium is a genus related to Tephrosia which comprises only three species. Compared to Tephrosia , which has been phytochemically and pharmacologically studied, Ptycholobium species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic act...

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Veröffentlicht in:BMC chemistry 2016-10, Vol.10 (1), p.58-58, Article 58
Hauptverfasser: Ngnintedo, Dominique, Fotso, Ghislain W., Kuete, Victor, Nana, Frederic, Sandjo, Louis P., Karaosmanoğlu, Oğuzhan, Sivas, Hülya, Keumedjio, Felix, Kirsch, Gilbert, Ngadjui, Bonaventure T., Andrae-Marobela, Kerstin
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container_end_page 58
container_issue 1
container_start_page 58
container_title BMC chemistry
container_volume 10
creator Ngnintedo, Dominique
Fotso, Ghislain W.
Kuete, Victor
Nana, Frederic
Sandjo, Louis P.
Karaosmanoğlu, Oğuzhan
Sivas, Hülya
Keumedjio, Felix
Kirsch, Gilbert
Ngadjui, Bonaventure T.
Andrae-Marobela, Kerstin
description Background Ptycholobium is a genus related to Tephrosia which comprises only three species. Compared to Tephrosia , which has been phytochemically and pharmacologically studied, Ptycholobium species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic activities of its secondary metabolites have been previously documented. Results From the non polar fractions of the roots bark of Ptycholobium contortum (syn Tephrosia contorta ), two new pterocarpans: seputhecarpan C 1 and seputhecarpan D 2 and a new pyrone derivative, ptycholopyrone A 3 were isolated. Alongside, five known compounds identified as 3-α,α-dimethylallyl-4-methoxy-6-styryl-α-pyrone or mundulea lactone 4 , glyasperin F 5 , seputhecarpan A 6 , seputheisoflavone 7 and 5- O -methyl-myo-inositol or sequoyitol 8 were also obtained. Their structures were established by the mean means of spectroscopic data in conjunction to those reported in literature. The NMR assignment of the major compound mundulea lactone 4 is revised in this paper. In addition, the cytotoxicity of the isolated metabolites was evaluated on two lung cancer cell lines A549 and SPC212. 8 was not active while compounds 1, 2, 4–7 displayed antiproliferative effects against the two carcinoma cell lines with IC 50 values below 75 µM. IC 50 values below 10 µM were obtained for 4, 6 and 7 on SPC212 cells. Conclusion Based on the obtained results, Ptycholobium contortum turns to be a rich source of phenolic metabolites among them some bearing prenyl moieties. This study reports for the first time the isolation of pyrone derivatives 3 and 4 from Ptycholobium genus. The cytotoxicity observed for the isolate is also reported for the first time and shows that 4, 6 and 7 could be chemically explored in order to develop a hit candidate against lung cancer. Graphical abstract Two new pterocarpans and a new pyrone derivative with cytotoxic activities from ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.
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Brummitt (Leguminosae): revised NMR assignment of mundulea lactone</title><source>DOAJ Directory of Open Access Journals</source><source>SpringerNature Journals</source><source>PubMed Central Open Access</source><source>Springer Nature OA Free Journals</source><source>Access via BioMed Central</source><source>PubMed Central</source><source>Free Full-Text Journals in Chemistry</source><creator>Ngnintedo, Dominique ; Fotso, Ghislain W. ; Kuete, Victor ; Nana, Frederic ; Sandjo, Louis P. ; Karaosmanoğlu, Oğuzhan ; Sivas, Hülya ; Keumedjio, Felix ; Kirsch, Gilbert ; Ngadjui, Bonaventure T. ; Andrae-Marobela, Kerstin</creator><creatorcontrib>Ngnintedo, Dominique ; Fotso, Ghislain W. ; Kuete, Victor ; Nana, Frederic ; Sandjo, Louis P. ; Karaosmanoğlu, Oğuzhan ; Sivas, Hülya ; Keumedjio, Felix ; Kirsch, Gilbert ; Ngadjui, Bonaventure T. ; Andrae-Marobela, Kerstin</creatorcontrib><description>Background Ptycholobium is a genus related to Tephrosia which comprises only three species. Compared to Tephrosia , which has been phytochemically and pharmacologically studied, Ptycholobium species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic activities of its secondary metabolites have been previously documented. Results From the non polar fractions of the roots bark of Ptycholobium contortum (syn Tephrosia contorta ), two new pterocarpans: seputhecarpan C 1 and seputhecarpan D 2 and a new pyrone derivative, ptycholopyrone A 3 were isolated. Alongside, five known compounds identified as 3-α,α-dimethylallyl-4-methoxy-6-styryl-α-pyrone or mundulea lactone 4 , glyasperin F 5 , seputhecarpan A 6 , seputheisoflavone 7 and 5- O -methyl-myo-inositol or sequoyitol 8 were also obtained. Their structures were established by the mean means of spectroscopic data in conjunction to those reported in literature. The NMR assignment of the major compound mundulea lactone 4 is revised in this paper. In addition, the cytotoxicity of the isolated metabolites was evaluated on two lung cancer cell lines A549 and SPC212. 8 was not active while compounds 1, 2, 4–7 displayed antiproliferative effects against the two carcinoma cell lines with IC 50 values below 75 µM. IC 50 values below 10 µM were obtained for 4, 6 and 7 on SPC212 cells. Conclusion Based on the obtained results, Ptycholobium contortum turns to be a rich source of phenolic metabolites among them some bearing prenyl moieties. This study reports for the first time the isolation of pyrone derivatives 3 and 4 from Ptycholobium genus. The cytotoxicity observed for the isolate is also reported for the first time and shows that 4, 6 and 7 could be chemically explored in order to develop a hit candidate against lung cancer. Graphical abstract Two new pterocarpans and a new pyrone derivative with cytotoxic activities from ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.</description><identifier>ISSN: 1752-153X</identifier><identifier>EISSN: 1752-153X</identifier><identifier>EISSN: 2661-801X</identifier><identifier>DOI: 10.1186/s13065-016-0204-x</identifier><identifier>PMID: 28316643</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Cytotoxicity ; Metabolites ; Organic and Medicinal Chemistry ; Phytochemicals ; Research Article</subject><ispartof>BMC chemistry, 2016-10, Vol.10 (1), p.58-58, Article 58</ispartof><rights>The Author(s) 2016</rights><rights>Chemistry Central Journal is a copyright of Springer, 2016.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c470t-3cf35467df9bbff75010e14c874ae30ef41a488173c126eb670105bc4903736a3</citedby><cites>FETCH-LOGICAL-c470t-3cf35467df9bbff75010e14c874ae30ef41a488173c126eb670105bc4903736a3</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/PMC5050614/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5050614/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28316643$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ngnintedo, Dominique</creatorcontrib><creatorcontrib>Fotso, Ghislain W.</creatorcontrib><creatorcontrib>Kuete, Victor</creatorcontrib><creatorcontrib>Nana, Frederic</creatorcontrib><creatorcontrib>Sandjo, Louis P.</creatorcontrib><creatorcontrib>Karaosmanoğlu, Oğuzhan</creatorcontrib><creatorcontrib>Sivas, Hülya</creatorcontrib><creatorcontrib>Keumedjio, Felix</creatorcontrib><creatorcontrib>Kirsch, Gilbert</creatorcontrib><creatorcontrib>Ngadjui, Bonaventure T.</creatorcontrib><creatorcontrib>Andrae-Marobela, Kerstin</creatorcontrib><title>Two new pterocarpans and a new pyrone derivative with cytotoxic activities from Ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone</title><title>BMC chemistry</title><addtitle>Chemistry Central Journal</addtitle><addtitle>Chem Cent J</addtitle><description>Background Ptycholobium is a genus related to Tephrosia which comprises only three species. Compared to Tephrosia , which has been phytochemically and pharmacologically studied, Ptycholobium species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic activities of its secondary metabolites have been previously documented. Results From the non polar fractions of the roots bark of Ptycholobium contortum (syn Tephrosia contorta ), two new pterocarpans: seputhecarpan C 1 and seputhecarpan D 2 and a new pyrone derivative, ptycholopyrone A 3 were isolated. Alongside, five known compounds identified as 3-α,α-dimethylallyl-4-methoxy-6-styryl-α-pyrone or mundulea lactone 4 , glyasperin F 5 , seputhecarpan A 6 , seputheisoflavone 7 and 5- O -methyl-myo-inositol or sequoyitol 8 were also obtained. Their structures were established by the mean means of spectroscopic data in conjunction to those reported in literature. The NMR assignment of the major compound mundulea lactone 4 is revised in this paper. In addition, the cytotoxicity of the isolated metabolites was evaluated on two lung cancer cell lines A549 and SPC212. 8 was not active while compounds 1, 2, 4–7 displayed antiproliferative effects against the two carcinoma cell lines with IC 50 values below 75 µM. IC 50 values below 10 µM were obtained for 4, 6 and 7 on SPC212 cells. Conclusion Based on the obtained results, Ptycholobium contortum turns to be a rich source of phenolic metabolites among them some bearing prenyl moieties. This study reports for the first time the isolation of pyrone derivatives 3 and 4 from Ptycholobium genus. The cytotoxicity observed for the isolate is also reported for the first time and shows that 4, 6 and 7 could be chemically explored in order to develop a hit candidate against lung cancer. Graphical abstract Two new pterocarpans and a new pyrone derivative with cytotoxic activities from ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Cytotoxicity</subject><subject>Metabolites</subject><subject>Organic and Medicinal Chemistry</subject><subject>Phytochemicals</subject><subject>Research Article</subject><issn>1752-153X</issn><issn>1752-153X</issn><issn>2661-801X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>C6C</sourceid><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNp1ks9u1DAQxiMEoqXwAFyQJS7bQxZPHDtZDpVo1QLSUhAqEjfLcSa7rhJ7sZ3981y8YF1tqRYkTjOa-c03M9KXZa-BTgFq8S4Ao4LnFEROC1rm2yfZMVS8yIGzn08P8qPsRQi3lPIaRPU8OypqBkKU7Dj7fbNxxOKGrCJ6p5VfKRuIsi1R-_LOO4ukRW_WKpo1ko2JS6J30UW3NZoonaomGgyk824g3-JOL13vGjMORDsbnY8pm1xPL6fnfnpKzv04DCZGMpnjYhyMdUHh6XvicW0CtuT6y3eiQjALO6CNxHVkGG079qhIn5ala15mzzrVB3z1EE-yH1eXNxef8vnXj58vPsxzXVY05kx3jJeiartZ03RdxSlQhFLXVamQUexKUGVdQ8U0FAIbUSWAN7qcUVYxodhJdrbXXY3NgK1O53jVy5U3g_I76ZSRf3esWcqFW0tOORVQJoHJg4B3v0YMUQ4maOx7ZdGNQUJdzWDGASChb_9Bb93obXovUYIXJfBCJAr2lPYuBI_d4zFA5b0l5N4SMllC3ltCbtPMm8MvHif-eCABxR4IqWUX6A9W_1f1DvYaxc0</recordid><startdate>20161005</startdate><enddate>20161005</enddate><creator>Ngnintedo, Dominique</creator><creator>Fotso, Ghislain W.</creator><creator>Kuete, Victor</creator><creator>Nana, Frederic</creator><creator>Sandjo, Louis P.</creator><creator>Karaosmanoğlu, Oğuzhan</creator><creator>Sivas, Hülya</creator><creator>Keumedjio, Felix</creator><creator>Kirsch, Gilbert</creator><creator>Ngadjui, Bonaventure T.</creator><creator>Andrae-Marobela, Kerstin</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>C6C</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7SR</scope><scope>7X7</scope><scope>7XB</scope><scope>8AO</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>K9.</scope><scope>KB.</scope><scope>M0S</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20161005</creationdate><title>Two new pterocarpans and a new pyrone derivative with cytotoxic activities from Ptycholobium contortum (N.E.Br.) 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Brummitt (Leguminosae): revised NMR assignment of mundulea lactone</atitle><jtitle>BMC chemistry</jtitle><stitle>Chemistry Central Journal</stitle><addtitle>Chem Cent J</addtitle><date>2016-10-05</date><risdate>2016</risdate><volume>10</volume><issue>1</issue><spage>58</spage><epage>58</epage><pages>58-58</pages><artnum>58</artnum><issn>1752-153X</issn><eissn>1752-153X</eissn><eissn>2661-801X</eissn><abstract>Background Ptycholobium is a genus related to Tephrosia which comprises only three species. Compared to Tephrosia , which has been phytochemically and pharmacologically studied, Ptycholobium species have only few or no reports on their chemical constituents. Moreover, no studies on the cytotoxic activities of its secondary metabolites have been previously documented. Results From the non polar fractions of the roots bark of Ptycholobium contortum (syn Tephrosia contorta ), two new pterocarpans: seputhecarpan C 1 and seputhecarpan D 2 and a new pyrone derivative, ptycholopyrone A 3 were isolated. Alongside, five known compounds identified as 3-α,α-dimethylallyl-4-methoxy-6-styryl-α-pyrone or mundulea lactone 4 , glyasperin F 5 , seputhecarpan A 6 , seputheisoflavone 7 and 5- O -methyl-myo-inositol or sequoyitol 8 were also obtained. Their structures were established by the mean means of spectroscopic data in conjunction to those reported in literature. The NMR assignment of the major compound mundulea lactone 4 is revised in this paper. In addition, the cytotoxicity of the isolated metabolites was evaluated on two lung cancer cell lines A549 and SPC212. 8 was not active while compounds 1, 2, 4–7 displayed antiproliferative effects against the two carcinoma cell lines with IC 50 values below 75 µM. IC 50 values below 10 µM were obtained for 4, 6 and 7 on SPC212 cells. Conclusion Based on the obtained results, Ptycholobium contortum turns to be a rich source of phenolic metabolites among them some bearing prenyl moieties. This study reports for the first time the isolation of pyrone derivatives 3 and 4 from Ptycholobium genus. The cytotoxicity observed for the isolate is also reported for the first time and shows that 4, 6 and 7 could be chemically explored in order to develop a hit candidate against lung cancer. Graphical abstract Two new pterocarpans and a new pyrone derivative with cytotoxic activities from ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><pmid>28316643</pmid><doi>10.1186/s13065-016-0204-x</doi><tpages>1</tpages><oa>free_for_read</oa></addata></record>
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subjects Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Cytotoxicity
Metabolites
Organic and Medicinal Chemistry
Phytochemicals
Research Article
title Two new pterocarpans and a new pyrone derivative with cytotoxic activities from Ptycholobium contortum (N.E.Br.) Brummitt (Leguminosae): revised NMR assignment of mundulea lactone
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