Cytotoxic polyketides containing tetramic acid moieties isolated from the fungus Myceliophthora thermophila: Elucidation of the relationship between cytotoxicity and stereoconfiguration

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Title:	Cytotoxic polyketides containing tetramic acid moieties isolated from the fungus Myceliophthora thermophila: Elucidation of the relationship between cytotoxicity and stereoconfiguration
Authors:	Yang, Yu-Liang Lu, Chun-Ping Chen, Mao-Yen Chen, Kuei-Yu Wu, Yang-Chang Wu, Shih-Hsiung
Contributors:	生科系
Keywords:	configuration determination cytotoxicity myceliothermophins polyketides structure elucidation
Date:	2007
Issue Date:	2009-11-11 10:58:35 (UTC+8)
Abstract:	Five new polyketides that contain tetramic acids, myceliothermophins A-E, were isolated from the thermophilic fungus Myceliophthora thermophila. Two sets of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one diastereomers, myceliothermophins A/B and C/D, were separated as pure compounds by using silica-gel column chromatography and recycling reverse-phase high-performance liquid chromatography (RP-HPLC). The relative configurations of the chiral centers in 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties were deduced from NOESY correlations. In the cytotoxic assay, the 5-(2-methylpropyldiene)-1 H-pyrrol-2(5H)-one analogue (myceliothermophin E) exhibited inhibition against four cancer cell lines. In addition, the significant inhibitory effect of myceliothermophins A and C and the inactivity of myceliothermophins B and D revealed the importance of the relative configurations of 5-alkyl-5-hydroxyl (or 5-methoxyl)-1H-pyrrol-2(5H)-one moieties on their cytotoxicity potency against cancer cells.
Relation:	CHEMISTRY-A EUROPEAN JOURNAL Volume: 13 Issue: 24 Pages: 6985-6991
Appears in Collections:	[Department of Biology ] journal articles

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