Komoda Toshikazu, Yoshida Kayo, Abe Naoki, Sugiyama Yasumasa, Imachi Misako, Hirota Hiroshi, Koshino Hiroyuki, Hirota Akira
Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan.
Biosci Biotechnol Biochem. 2004 Jan;68(1):104-11. doi: 10.1271/bbb.68.104.
A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C26H33NO7, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a beta-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the 1H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM.
设计了一种用于脂氧合酶抑制剂的简单新测定法。该测定法用于寻找新型脂氧合酶抑制剂四花瓣酮A（1）。四花瓣酮A（1），化学式为C26H33NO7，是从链霉菌属USF - 4727菌株中分离得到的。其平面结构通过光谱证据以及用重氮甲烷甲基化来确定，以显示存在一种新型四环骨架和一个β - D - 鼠李糖基部分。通过1H - NMR谱中的耦合常数、NOE相关、改良的莫舍尔方法和推导研究了1的立体化学。我们在之前的论文中报道了1的结构解析。然而，进一步的研究给出了1的另一种结构，本文对此进行了描述。四花瓣酮A对大豆脂氧合酶的抑制活性与两种著名的脂氧合酶抑制剂曲酸和去甲二氢愈创木酸相似，而甲基化的四花瓣酮A（2）即使在浓度为1 mM时也几乎没有抑制活性。
