https://scholars.lib.ntu.edu.tw/handle/123456789/143732
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 |
Keywords: | Configuration determination; Cytotoxicity; Myceliothermophins; Polyketides; Structure elucidation | Issue Date: | 2007 | Start page/Pages: | 6985-6991 | Source: | Chemistry-A European Journal | 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. |
URI: | http://ntur.lib.ntu.edu.tw//handle/246246/163111 | DOI: | 10.1002/chem.200700038 | SDG/Keyword: | 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 |
Appears in Collections: | 生化科學研究所 |
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