Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities
A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5–10. The structures of these co...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2012-04, Vol.75 (4), p.605-609 |
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| creator | Yoshikawa, Kazuko Ito, Takuya Iseki, Kanako Baba, Chihiro Imagawa, Hiroshi Yagi, Yasuyuki Morita, Hiroshi Asakawa, Yoshinori Kawano, Sachiko Hashimoto, Toshihiro |
| description | A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5–10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 μM) against HL-60 cells. Compounds 4–9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3–52.4 μM. |
| doi_str_mv | 10.1021/np200788u |
| format | Article |
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The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 μM) against HL-60 cells. Compounds 4–9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3–52.4 μM.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np200788u</identifier><identifier>PMID: 22537363</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - isolation & purification ; Antineoplastic Agents, Phytogenic - pharmacology ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; HL-60 Cells ; Humans ; Inhibitory Concentration 50 ; Japan ; Molecular Conformation ; Molecular Structure ; Orchidaceae - chemistry ; Phenanthrenes - chemistry ; Phenanthrenes - isolation & purification ; Phenanthrenes - pharmacology ; Plant Roots - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2012-04, Vol.75 (4), p.605-609</ispartof><rights>Copyright © 2012 American Chemical Society and American Society of Pharmacognosy</rights><rights>2012 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-d1472eebc7d9ffd7edab9c5116d717a80dd3e7ecf0ea247c937120be871e67523</citedby><cites>FETCH-LOGICAL-a315t-d1472eebc7d9ffd7edab9c5116d717a80dd3e7ecf0ea247c937120be871e67523</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/np200788u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np200788u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22537363$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoshikawa, Kazuko</creatorcontrib><creatorcontrib>Ito, Takuya</creatorcontrib><creatorcontrib>Iseki, Kanako</creatorcontrib><creatorcontrib>Baba, Chihiro</creatorcontrib><creatorcontrib>Imagawa, Hiroshi</creatorcontrib><creatorcontrib>Yagi, Yasuyuki</creatorcontrib><creatorcontrib>Morita, Hiroshi</creatorcontrib><creatorcontrib>Asakawa, Yoshinori</creatorcontrib><creatorcontrib>Kawano, Sachiko</creatorcontrib><creatorcontrib>Hashimoto, Toshihiro</creatorcontrib><title>Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5–10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 μM) against HL-60 cells. Compounds 4–9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3–52.4 μM.</description><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - isolation & purification</subject><subject>Antineoplastic Agents, Phytogenic - pharmacology</subject><subject>Crystallography, X-Ray</subject><subject>Drug Screening Assays, Antitumor</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Japan</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Orchidaceae - chemistry</subject><subject>Phenanthrenes - chemistry</subject><subject>Phenanthrenes - isolation & purification</subject><subject>Phenanthrenes - pharmacology</subject><subject>Plant Roots - chemistry</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkL1OwzAURi0EoqUw8ALICxIMAf8kcTKWQgtSEQxljhz7hrpKnGInRX17jFo6Md3l3CN9B6FLSu4oYfTerhkhIsv6IzSkCSNRSlhyjIaEpjziWRoP0Jn3K0IIJ3lyigaMJVzwlA-Rfl-ClbZbOrCAH8GZjezMBjyuXNvgybYpjTZ9g2cOZIendfsNDr9KZwDPZR--lLFYWo0XSzAOP5i2bj-NkjUeqyAynQF_jk4qWXu42N8R-pg-LSbP0fxt9jIZzyPJadJFmsaCAZRK6LyqtAAty1wllKZaUCEzojUHAaoiIFksVM4FZaSETFBIRcL4CN3svGvXfvXgu6IxXkFdSwtt7wtKQi7OY5EF9HaHKtd676Aq1s400m0DVPxGLQ5RA3u11_ZlA_pA_lUMwPUOkMoXq7Z3Nqz8R_QDymh_QQ</recordid><startdate>20120427</startdate><enddate>20120427</enddate><creator>Yoshikawa, Kazuko</creator><creator>Ito, Takuya</creator><creator>Iseki, Kanako</creator><creator>Baba, Chihiro</creator><creator>Imagawa, Hiroshi</creator><creator>Yagi, Yasuyuki</creator><creator>Morita, Hiroshi</creator><creator>Asakawa, Yoshinori</creator><creator>Kawano, Sachiko</creator><creator>Hashimoto, Toshihiro</creator><general>American Chemical Society and American Society of Pharmacognosy</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></search><sort><creationdate>20120427</creationdate><title>Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities</title><author>Yoshikawa, Kazuko ; Ito, Takuya ; Iseki, Kanako ; Baba, Chihiro ; Imagawa, Hiroshi ; Yagi, Yasuyuki ; Morita, Hiroshi ; Asakawa, Yoshinori ; Kawano, Sachiko ; Hashimoto, Toshihiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-d1472eebc7d9ffd7edab9c5116d717a80dd3e7ecf0ea247c937120be871e67523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - isolation & purification</topic><topic>Antineoplastic Agents, Phytogenic - pharmacology</topic><topic>Crystallography, X-Ray</topic><topic>Drug Screening Assays, Antitumor</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Japan</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Orchidaceae - chemistry</topic><topic>Phenanthrenes - chemistry</topic><topic>Phenanthrenes - isolation & purification</topic><topic>Phenanthrenes - pharmacology</topic><topic>Plant Roots - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoshikawa, Kazuko</creatorcontrib><creatorcontrib>Ito, Takuya</creatorcontrib><creatorcontrib>Iseki, Kanako</creatorcontrib><creatorcontrib>Baba, Chihiro</creatorcontrib><creatorcontrib>Imagawa, Hiroshi</creatorcontrib><creatorcontrib>Yagi, Yasuyuki</creatorcontrib><creatorcontrib>Morita, Hiroshi</creatorcontrib><creatorcontrib>Asakawa, Yoshinori</creatorcontrib><creatorcontrib>Kawano, Sachiko</creatorcontrib><creatorcontrib>Hashimoto, Toshihiro</creatorcontrib><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>Yoshikawa, Kazuko</au><au>Ito, Takuya</au><au>Iseki, Kanako</au><au>Baba, Chihiro</au><au>Imagawa, Hiroshi</au><au>Yagi, Yasuyuki</au><au>Morita, Hiroshi</au><au>Asakawa, Yoshinori</au><au>Kawano, Sachiko</au><au>Hashimoto, Toshihiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2012-04-27</date><risdate>2012</risdate><volume>75</volume><issue>4</issue><spage>605</spage><epage>609</epage><pages>605-609</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5–10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC50 2.8 μM) against HL-60 cells. Compounds 4–9 also showed weak cytotoxic activity against the HL-60 cell line with IC50 values of 19.3–52.4 μM.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>22537363</pmid><doi>10.1021/np200788u</doi><tpages>5</tpages></addata></record> |
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| subjects | Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - isolation & purification Antineoplastic Agents, Phytogenic - pharmacology Crystallography, X-Ray Drug Screening Assays, Antitumor HL-60 Cells Humans Inhibitory Concentration 50 Japan Molecular Conformation Molecular Structure Orchidaceae - chemistry Phenanthrenes - chemistry Phenanthrenes - isolation & purification Phenanthrenes - pharmacology Plant Roots - chemistry |
| title | Phenanthrene Derivatives from Cymbidium Great Flower Marie Laurencin and Their Biological Activities |
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