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Synthesis of two possible diastereomers of reticulatain-1 |
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| Authors: | Hidefumi Makabe Aya Miyawaki Yasunao Hattori Masato Abe |
| Institution: | a Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, 8304 Minami-minowa, Kamiina, Nagano 399-4598, Japan b Department of Biological Science and Technology, Faculty of Engineering University of Tokushima, 2-1 Minamijosanjimacho, Tokushima 770-8506, Japan c Division of Applied Sciences, Graduate School of Agriculture, Kyoto University, Kita-shirakawa, Sakyo-ku, Kyoto 606-8502, Japan |
| Abstract: | A convergent synthesis of two possible diastereomers of reticulatain-1 (1a and 1b) was accomplished. Comparison of the specific optical rotations of 1a and 1b did not allow for the strict determination of the absolute configuration. However, bis-(R)-MTPA esters of 1a and 1b showed a clear difference in chemical shifts in the 1H NMR spectra. If the bis-(R)-MTPA ester of natural reticulatain-1 (1) is available, the absolute configuration of 1 will be determined. Inhibitory action of these compounds was examined with bovine heart mitochondrial complex I. Both compounds showed almost the same activity. |
| Keywords: | Annonaceous acetogenin Antitumor Mitochondrial complex I |
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