Cytotoxic Polyketides Containing Tetramic Acid Moieties Isolated from the Fungus Myceliophthora Thermophila: Elucidation of the Relationship between Cytotoxicity and Stereoconfiguration
Resource
Chemistry - A European Journal 13 (24): 6985-6991
Journal
Chemistry-A European Journal
Pages
6985-6991
Date Issued
2007
Date
2007
Author(s)
Yang, Yu-Liang
Lu, Chun-Ping
Chen, Mao-Yen
Chen, Kuei-Yu
Wu, Yang-Chang
Wu, Shih-Hsiung
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)-l H/-pyrrol2(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 rela tive configurations of the chiral centers in 5-alkyl-5-hydroxyl (or 5-methoxyl)lH-pyrrol-2(5H)-one moieties were deduced from NOESY correlations. In the cytotoxic assay, the 5-(2-methylpropyldiene)-lH-pyrrol-2(5H)-one ana-logue (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 5alkyl-5-hydroxyl (or 5-methoxyl)-lHpyrrol-2(5H)-one moieties on their cytotoxicity potency against cancer cells. ? 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Subjects
Configuration determination; Cytotoxicity; Myceliothermophins; Polyketides; Structure elucidation
SDGs
Other Subjects
Configuration determination; Myceliothermophins; Polyketides; Structure elucidation; Cell death; Enzyme inhibition; Fungi; High performance liquid chromatography; Silica gel; Stereochemistry; Cytotoxicity; 2 pyrrolidone derivative; macrolide; tetramic acid; unclassified drug; article; cell survival; chemical structure; chemistry; drug effect; human; isolation and purification; mass spectrometry; nuclear magnetic resonance spectroscopy; Sordariales; stereoisomerism; tumor cell line; Cell Line, Tumor; Cell Survival; Humans; Macrolides; Magnetic Resonance Spectroscopy; Mass Spectrometry; Models, Molecular; Molecular Structure; Pyrrolidinones; Sordariales; Stereoisomerism
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