Stereochemistries of monapinones produced by Talaromyces pinophilus FKI-3864

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• 作者：Ryuji Uchida ; Mio Kawaguchi ; Noriko Sato ; Hiroshi Tomoda ; ^{tomodah@pharm.kitasato-u.ac.jp}
• 关键词：Monapinone ; Stereochemistry ; Triacylglycerol synthesis inhibitor ; Dinapinone ; Talaromyces pinophilus
• 刊名：Acta Pharmaceutica Sinica B
• 出版年：2013
• 出版时间：May, 2013
• 年：2013
• 卷：3
• 期：3
• 页码：163-166
• 全文大小：303 K

文摘

Monapinones A (class=""boldFont"">1) to E (class=""boldFont"">5), half parts of dinapinones, were produced by fermentation of Talaromyces pinophilus FKI-3864 in seawater-containing medium and have a common dihydronaphthopyranone skeleton with a different long alkyl chain. The relative stereochemistries of class=""boldFont"">3-class=""boldFont"">5 were elucidated by various NMR experiments including analysis of ¹H NMR coupling constants, ROESY and the dihedral angles. The absolute stereochemistries of class=""boldFont"">3-class=""boldFont"">5 at C-3 were determined by the circular dichroism spectra in comparison to the data of (R)- and (S)-semivioxanthins (class=""boldFont"">6 and class=""boldFont"">7). Accordingly, total absolute stereochemistries of class=""boldFont"">3-class=""boldFont"">5 were concluded to be 3S,13R,15R,17R,19R,3S,13R,15R,17R and 3S,13R,15R, respectively.