Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan.
J Agric Food Chem. 2010 Jul 14;58(13):7777-81. doi: 10.1021/jf101064v.
The biotransformation of bergapten (1) by the fungus Glomerella cingulata gave the corresponding reduced acid, 6,7-furano-5-methoxy hydrocoumaric acid (2), a new compound. Xanthotoxin (3) was also converted to the corresponding reduced acid cnidiol b (4) and demethylated metabolite xanthotoxol (5) by G. cingulata. The structure of the new compound 2 was elucidated by high-resolution mass spectrometry, extensive NMR techniques, including (1)H NMR and (13)C NMR, (1)H-(1)H correlation spectroscopy, heteronuclear multiple quantum coherence, and heteonuclear multiple bond coherence. The methyl ester or methyl ether or methyl ester and ether derivatives of 2 and 4 were synthesized. All compounds were tested for the beta-secretase (BACE1) inhibitory activity in vitro. The methyl ester and ether derivative 8 was shown to possess BACE1 inhibitory activity, and a IC(50) value was 0.64 +/- 0.04 mM.
真菌层出镰刀菌（Glomerella cingulata）使佛手柑内酯（1）发生生物转化，生成相应的还原酸 6,7-呋喃-5-甲氧基氢桂皮酸（2），这是一种新化合物。黄杉毒素（3）也被真菌层出镰刀菌转化为相应的还原酸 cnidiol b（4）和去甲基代谢物黄杉毒醇（5）。新化合物 2 的结构通过高分辨质谱、广泛的 NMR 技术（包括 1H NMR 和 13C NMR、1H-1H 相关谱、异核多量子相干和异核多键相干）进行了阐明。还合成了 2 和 4 的甲酯、甲醚或甲酯和醚衍生物。所有化合物均在体外进行了β-分泌酶（BACE1）抑制活性测试。甲酯和醚衍生物 8 表现出 BACE1 抑制活性，IC50 值为 0.64±0.04mM。
