Flavonoid Glucuronides and a Chromone from the Aquatic Macrophyte Stratiotes aloides
The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (1) and chrysoeriol 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (2), as well as the new 2-(2-hyd...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2009-05, Vol.72 (5), p.835-840 |
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| creator | Conrad, Jürgen Förster-Fromme, Bernhard Constantin, Mihaela-Anca Ondrus, Vladimir Mika, Sabine Mert-Balci, Fadime Klaiber, Iris Pfannstiel, Jens Möller, Wolfgang Rösner, Harald Förster-Fromme, Karin Beifuss, Uwe |
| description | The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (1) and chrysoeriol 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (2), as well as the new 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone (5) and chrysoeriol 7-O-β-(6-O-malonyl)glucopyranoside (3), which has been assigned via NMR data for the first time. Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside α-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-β-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50−300 μg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 μM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens. |
| doi_str_mv | 10.1021/np800769g |
| format | Article |
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Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside α-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-β-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50−300 μg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 μM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np800769g</identifier><identifier>PMID: 20560646</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Northbrook, IL: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Biological and medical sciences ; Chromones - chemistry ; Chromones - isolation & purification ; Chromones - pharmacology ; Drug Screening Assays, Antitumor ; Enterobacter cloacae - drug effects ; Escherichia coli - drug effects ; Flavonoids - chemistry ; Flavonoids - isolation & purification ; Flavonoids - pharmacology ; Fresh Water ; General pharmacology ; Germany ; Glucuronides - chemistry ; Glucuronides - isolation & purification ; Glucuronides - pharmacology ; Humans ; Hydrocharitaceae - chemistry ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Plants, Medicinal - chemistry ; Pseudomonas putida - drug effects ; Stereoisomerism</subject><ispartof>Journal of natural products (Washington, D.C.), 2009-05, Vol.72 (5), p.835-840</ispartof><rights>Copyright © 2009 American Chemical Society and American Society of Pharmacognosy</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a344t-532920d772839679308f4b44024809da61f86d2e9503339f5f7f8e4ba8ab61963</citedby><cites>FETCH-LOGICAL-a344t-532920d772839679308f4b44024809da61f86d2e9503339f5f7f8e4ba8ab61963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np800769g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np800769g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21566723$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20560646$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Conrad, Jürgen</creatorcontrib><creatorcontrib>Förster-Fromme, Bernhard</creatorcontrib><creatorcontrib>Constantin, Mihaela-Anca</creatorcontrib><creatorcontrib>Ondrus, Vladimir</creatorcontrib><creatorcontrib>Mika, Sabine</creatorcontrib><creatorcontrib>Mert-Balci, Fadime</creatorcontrib><creatorcontrib>Klaiber, Iris</creatorcontrib><creatorcontrib>Pfannstiel, Jens</creatorcontrib><creatorcontrib>Möller, Wolfgang</creatorcontrib><creatorcontrib>Rösner, Harald</creatorcontrib><creatorcontrib>Förster-Fromme, Karin</creatorcontrib><creatorcontrib>Beifuss, Uwe</creatorcontrib><title>Flavonoid Glucuronides and a Chromone from the Aquatic Macrophyte Stratiotes aloides</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (1) and chrysoeriol 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (2), as well as the new 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone (5) and chrysoeriol 7-O-β-(6-O-malonyl)glucopyranoside (3), which has been assigned via NMR data for the first time. Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside α-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-β-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50−300 μg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 μM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens.</description><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Chromones - chemistry</subject><subject>Chromones - isolation & purification</subject><subject>Chromones - pharmacology</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Enterobacter cloacae - drug effects</subject><subject>Escherichia coli - drug effects</subject><subject>Flavonoids - chemistry</subject><subject>Flavonoids - isolation & purification</subject><subject>Flavonoids - pharmacology</subject><subject>Fresh Water</subject><subject>General pharmacology</subject><subject>Germany</subject><subject>Glucuronides - chemistry</subject><subject>Glucuronides - isolation & purification</subject><subject>Glucuronides - pharmacology</subject><subject>Humans</subject><subject>Hydrocharitaceae - chemistry</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Plants, Medicinal - chemistry</subject><subject>Pseudomonas putida - drug effects</subject><subject>Stereoisomerism</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1OwzAQhC0EoqVw4AWQLwhxCKx_4sTHqqIFqYgD5Rw5iU1TJXFrJ0h9e1y1tBdOI62-md0dhG4JPBGg5LldpwCJkN9naEhiCpEAGp-jIRDBIpYKPkBX3q8AgIGML9GAQixAcDFEi2mtfmxrqxLP6r7onW2rUnus2hIrPFk629hWYxMUd0uNx5tedVWB31Xh7Hq57TT-7FwY2W7nqu3OfY0ujKq9vjnoCH1NXxaT12j-MXubjOeRYpx3UcyopFAmCU2ZFIlkkBqecw6UpyBLJYhJRUm1jIExJk1sEpNqnqtU5YJIwUboYZ-7dnbTa99lTeULXdeq1bb3WRJs4eOEB_JxT4arvXfaZGtXNcptMwLZrsPs2GFg7w6pfd7o8kj-lRaA-wOgfKFq41RbVP7EkViIhLITpwqfrWzv2lDGPwt_AUtBg8Y</recordid><startdate>20090522</startdate><enddate>20090522</enddate><creator>Conrad, Jürgen</creator><creator>Förster-Fromme, Bernhard</creator><creator>Constantin, Mihaela-Anca</creator><creator>Ondrus, Vladimir</creator><creator>Mika, Sabine</creator><creator>Mert-Balci, Fadime</creator><creator>Klaiber, Iris</creator><creator>Pfannstiel, Jens</creator><creator>Möller, Wolfgang</creator><creator>Rösner, Harald</creator><creator>Förster-Fromme, Karin</creator><creator>Beifuss, Uwe</creator><general>American Chemical Society and American Society of Pharmacognosy</general><general>American Society of Pharmacognosy</general><scope>IQODW</scope><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></search><sort><creationdate>20090522</creationdate><title>Flavonoid Glucuronides and a Chromone from the Aquatic Macrophyte Stratiotes aloides</title><author>Conrad, Jürgen ; Förster-Fromme, Bernhard ; Constantin, Mihaela-Anca ; Ondrus, Vladimir ; Mika, Sabine ; Mert-Balci, Fadime ; Klaiber, Iris ; Pfannstiel, Jens ; Möller, Wolfgang ; Rösner, Harald ; Förster-Fromme, Karin ; Beifuss, Uwe</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-532920d772839679308f4b44024809da61f86d2e9503339f5f7f8e4ba8ab61963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chromones - chemistry</topic><topic>Chromones - isolation & purification</topic><topic>Chromones - pharmacology</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Enterobacter cloacae - drug effects</topic><topic>Escherichia coli - drug effects</topic><topic>Flavonoids - chemistry</topic><topic>Flavonoids - isolation & purification</topic><topic>Flavonoids - pharmacology</topic><topic>Fresh Water</topic><topic>General pharmacology</topic><topic>Germany</topic><topic>Glucuronides - chemistry</topic><topic>Glucuronides - isolation & purification</topic><topic>Glucuronides - pharmacology</topic><topic>Humans</topic><topic>Hydrocharitaceae - chemistry</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Plants, Medicinal - chemistry</topic><topic>Pseudomonas putida - drug effects</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Conrad, Jürgen</creatorcontrib><creatorcontrib>Förster-Fromme, Bernhard</creatorcontrib><creatorcontrib>Constantin, Mihaela-Anca</creatorcontrib><creatorcontrib>Ondrus, Vladimir</creatorcontrib><creatorcontrib>Mika, Sabine</creatorcontrib><creatorcontrib>Mert-Balci, Fadime</creatorcontrib><creatorcontrib>Klaiber, Iris</creatorcontrib><creatorcontrib>Pfannstiel, Jens</creatorcontrib><creatorcontrib>Möller, Wolfgang</creatorcontrib><creatorcontrib>Rösner, Harald</creatorcontrib><creatorcontrib>Förster-Fromme, Karin</creatorcontrib><creatorcontrib>Beifuss, Uwe</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Conrad, Jürgen</au><au>Förster-Fromme, Bernhard</au><au>Constantin, Mihaela-Anca</au><au>Ondrus, Vladimir</au><au>Mika, Sabine</au><au>Mert-Balci, Fadime</au><au>Klaiber, Iris</au><au>Pfannstiel, Jens</au><au>Möller, Wolfgang</au><au>Rösner, Harald</au><au>Förster-Fromme, Karin</au><au>Beifuss, Uwe</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Flavonoid Glucuronides and a Chromone from the Aquatic Macrophyte Stratiotes aloides</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2009-05-22</date><risdate>2009</risdate><volume>72</volume><issue>5</issue><spage>835</spage><epage>840</epage><pages>835-840</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>The first phytochemical analysis of the aquatic macrophyte Stratiotes aloides afforded two new flavonoid glucuronides, luteolin 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (1) and chrysoeriol 7-O-β-d-glucopyranosiduronic acid-(1→2)-β-d-glucopyranoside (2), as well as the new 2-(2-hydroxypentyl)-5-carboxy-7-methoxychromone (5) and chrysoeriol 7-O-β-(6-O-malonyl)glucopyranoside (3), which has been assigned via NMR data for the first time. Additionally, free amino acids such as tryptophan, arginine, leucine, isoleucine, phenylalanine, and tyrosine along with choline, cis-aconitic acid, the phenolic glycoside α-arbutine, the chlorophyll derivative phaeophorbide a, and the flavonoid glycoside luteolin 7-O-β-(6-O-malonyl)glucopyranoside (4) were isolated. Despite the low quantities obtained in some cases (between 50−300 μg), the structures of all compounds were unambiguously elucidated by extensive NMR and MS experiments. With a delay of 2 days compound 1 (10 and 50 μM test concentration) strongly inhibited the growth of human SH-SY5Y neuroblastoma cells in a dose-dependent manner, whereas only a moderate growth inhibition of human Patu 8902 carcinoma cells could be observed. Compounds 1 and 2 showed no activities against the bacteria Escherichia coli BW25113, Pseudomonas pudida KT2440, and Enterobacter cloacae subsp. dissolvens.</abstract><cop>Northbrook, IL</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>20560646</pmid><doi>10.1021/np800769g</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 2009-05, Vol.72 (5), p.835-840 |
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| subjects | Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Biological and medical sciences Chromones - chemistry Chromones - isolation & purification Chromones - pharmacology Drug Screening Assays, Antitumor Enterobacter cloacae - drug effects Escherichia coli - drug effects Flavonoids - chemistry Flavonoids - isolation & purification Flavonoids - pharmacology Fresh Water General pharmacology Germany Glucuronides - chemistry Glucuronides - isolation & purification Glucuronides - pharmacology Humans Hydrocharitaceae - chemistry Medical sciences Microbial Sensitivity Tests Molecular Structure Nuclear Magnetic Resonance, Biomolecular Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Plants, Medicinal - chemistry Pseudomonas putida - drug effects Stereoisomerism |
| title | Flavonoid Glucuronides and a Chromone from the Aquatic Macrophyte Stratiotes aloides |
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