New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation
To date, entomopathogenic fungi have not been extensively examined by natural product chemists. In this study, we isolated novel pyrone diterpene-type compounds, metarhizins A ( 1) and B ( 2), from methanol extracts of entomopathogenic fungus, Metarhizium flavoviride. They showed potent and selectiv...
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Veröffentlicht in: | Tetrahedron 2009-01, Vol.65 (2), p.469-477 |
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creator | Kikuchi, Haruhisa Hoshi, Tomoko Kitayama, Minoru Sekiya, Mizuki Katou, Yasuhiro Ueda, Kazunori Kubohara, Yuzuru Sato, Hiroki Shimazu, Mitsuaki Kurata, Shoichiro Oshima, Yoshiteru |
description | To date, entomopathogenic fungi have not been extensively examined by natural product chemists. In this study, we isolated novel pyrone diterpene-type compounds, metarhizins A (
1) and B (
2), from methanol extracts of entomopathogenic fungus,
Metarhizium flavoviride. They showed potent and selective antiproliferative activity against both insect and human cancer cell lines. These results indicate that metarhizins A (
1) and B (
2) can be used as novel lead compounds for anti-cancer agents and probes for cell cycle regulation. To further investigate the structural requirements for this inhibitory activity, we synthesized many metarhizin derivatives and evaluated their antiproliferative activities.
[Display omitted] |
doi_str_mv | 10.1016/j.tet.2008.11.014 |
format | Article |
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1) and B (
2), from methanol extracts of entomopathogenic fungus,
Metarhizium flavoviride. They showed potent and selective antiproliferative activity against both insect and human cancer cell lines. These results indicate that metarhizins A (
1) and B (
2) can be used as novel lead compounds for anti-cancer agents and probes for cell cycle regulation. To further investigate the structural requirements for this inhibitory activity, we synthesized many metarhizin derivatives and evaluated their antiproliferative activities.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2008.11.014</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Antineoplastic agents ; Biological and medical sciences ; Chemistry ; Condensed benzenic and aromatic compounds ; Exact sciences and technology ; General aspects ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Medical sciences ; Metarhizium flavoviride ; Organic chemistry ; Pharmacology. Drug treatments ; Preparations and properties ; Terpenoids</subject><ispartof>Tetrahedron, 2009-01, Vol.65 (2), p.469-477</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-8171e257efcacc3e267aef3f153add31bcd99e4534b9b17765085530f37349b63</citedby><cites>FETCH-LOGICAL-c358t-8171e257efcacc3e267aef3f153add31bcd99e4534b9b17765085530f37349b63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0040402008019558$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21048458$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kikuchi, Haruhisa</creatorcontrib><creatorcontrib>Hoshi, Tomoko</creatorcontrib><creatorcontrib>Kitayama, Minoru</creatorcontrib><creatorcontrib>Sekiya, Mizuki</creatorcontrib><creatorcontrib>Katou, Yasuhiro</creatorcontrib><creatorcontrib>Ueda, Kazunori</creatorcontrib><creatorcontrib>Kubohara, Yuzuru</creatorcontrib><creatorcontrib>Sato, Hiroki</creatorcontrib><creatorcontrib>Shimazu, Mitsuaki</creatorcontrib><creatorcontrib>Kurata, Shoichiro</creatorcontrib><creatorcontrib>Oshima, Yoshiteru</creatorcontrib><title>New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation</title><title>Tetrahedron</title><description>To date, entomopathogenic fungi have not been extensively examined by natural product chemists. In this study, we isolated novel pyrone diterpene-type compounds, metarhizins A (
1) and B (
2), from methanol extracts of entomopathogenic fungus,
Metarhizium flavoviride. They showed potent and selective antiproliferative activity against both insect and human cancer cell lines. These results indicate that metarhizins A (
1) and B (
2) can be used as novel lead compounds for anti-cancer agents and probes for cell cycle regulation. To further investigate the structural requirements for this inhibitory activity, we synthesized many metarhizin derivatives and evaluated their antiproliferative activities.
[Display omitted]</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>General aspects</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Medical sciences</subject><subject>Metarhizium flavoviride</subject><subject>Organic chemistry</subject><subject>Pharmacology. 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Drug treatments</topic><topic>Preparations and properties</topic><topic>Terpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kikuchi, Haruhisa</creatorcontrib><creatorcontrib>Hoshi, Tomoko</creatorcontrib><creatorcontrib>Kitayama, Minoru</creatorcontrib><creatorcontrib>Sekiya, Mizuki</creatorcontrib><creatorcontrib>Katou, Yasuhiro</creatorcontrib><creatorcontrib>Ueda, Kazunori</creatorcontrib><creatorcontrib>Kubohara, Yuzuru</creatorcontrib><creatorcontrib>Sato, Hiroki</creatorcontrib><creatorcontrib>Shimazu, Mitsuaki</creatorcontrib><creatorcontrib>Kurata, Shoichiro</creatorcontrib><creatorcontrib>Oshima, Yoshiteru</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kikuchi, Haruhisa</au><au>Hoshi, Tomoko</au><au>Kitayama, Minoru</au><au>Sekiya, Mizuki</au><au>Katou, Yasuhiro</au><au>Ueda, Kazunori</au><au>Kubohara, Yuzuru</au><au>Sato, Hiroki</au><au>Shimazu, Mitsuaki</au><au>Kurata, Shoichiro</au><au>Oshima, Yoshiteru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation</atitle><jtitle>Tetrahedron</jtitle><date>2009-01-01</date><risdate>2009</risdate><volume>65</volume><issue>2</issue><spage>469</spage><epage>477</epage><pages>469-477</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>To date, entomopathogenic fungi have not been extensively examined by natural product chemists. In this study, we isolated novel pyrone diterpene-type compounds, metarhizins A (
1) and B (
2), from methanol extracts of entomopathogenic fungus,
Metarhizium flavoviride. They showed potent and selective antiproliferative activity against both insect and human cancer cell lines. These results indicate that metarhizins A (
1) and B (
2) can be used as novel lead compounds for anti-cancer agents and probes for cell cycle regulation. To further investigate the structural requirements for this inhibitory activity, we synthesized many metarhizin derivatives and evaluated their antiproliferative activities.
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subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Antineoplastic agents Biological and medical sciences Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology General aspects Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Medical sciences Metarhizium flavoviride Organic chemistry Pharmacology. Drug treatments Preparations and properties Terpenoids |
title | New diterpene pyrone-type compounds, metarhizins A and B, isolated from entomopathogenic fungus, Metarhizium flavoviride and their inhibitory effects on cellular proliferation |
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