Tronina Tomasz, Strugała Paulina, Popłoński Jarosław, Włoch Aleksandra, Sordon Sandra, Bartmańska Agnieszka, Huszcza Ewa
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland.
Molecules. 2017 Jul 21;22(7):1230. doi: 10.3390/molecules22071230.
The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol () and ()-6,4'-dihydroxy-4-methoxy-7-prenylaurone ()) was performed in one step reactions from xanthohumol ()-major prenylated chalcone naturally occurring in hops. Obtained flavonoids (-) and xanthohumol () were used as substrates for regioselective fungal glycosylation catalyzed by two species and . As a result six glycosides (-) were formed, of which four glycosides (-) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4--methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone () had the highest binding affinity to HSA (8.624 × 10⁴ M) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than α,β-dihydrochalcone () and aurone (). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity.
从啤酒花中天然存在的主要异戊烯基化查耳酮黄腐酚出发，通过一步反应合成了不同类别的异戊烯基化苷元（α,β-二氢黄腐酚（）和（）-6,4'-二羟基-4-甲氧基-7-异戊烯基月桂酮（））。所得到的类黄酮（-）和黄腐酚（）被用作由两种物种和催化的区域选择性真菌糖基化反应的底物。结果形成了六种糖苷（-），其中四种糖苷（-）迄今尚未见报道。研究了类黄酮骨架以及类黄酮分子中吡喃葡萄糖和4--甲基吡喃葡萄糖部分的存在对与血浆中的主要蛋白质人血清白蛋白（HSA）结合以及对环氧合酶COX-1和COX-2的抑制作用的影响。结果表明，在所有测试化合物中，查耳酮（）对HSA的结合亲和力最高（8.624×10⁴ M）。它还表现出对环氧合酶活性的最高抑制作用，并且是比α,β-二氢查耳酮（）和月桂酮（）强两倍的抑制剂。类黄酮分子中糖部分的存在导致HSA结合活性丧失以及环氧合酶活性抑制作用降低。
