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
Hauptverfasser: Kikuchi, Haruhisa, Hoshi, Tomoko, Kitayama, Minoru, Sekiya, Mizuki, Katou, Yasuhiro, Ueda, Kazunori, Kubohara, Yuzuru, Sato, Hiroki, Shimazu, Mitsuaki, Kurata, Shoichiro, Oshima, Yoshiteru
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container_end_page 477
container_issue 2
container_start_page 469
container_title Tetrahedron
container_volume 65
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
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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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