PDF(Pubmed)
Abstract：
Chalcones are intermediate products in the biosynthesis of flavonoids, which possess a wide range of biological properties, including antimicrobial and anticancer activities. The introduction of a chlorine atom and the glucosyl moiety into their structure may increase their bioavailability, bioactivity, and pharmacological use. The combined chemical and biotechnological methods can be applied to obtain such compounds. Therefore, 2-chloro-2\'-hydroxychalcone and 3-chloro-2\'-hydroxychalcone were synthesized and biotransformed in cultures of two strains of filamentous fungi, i.e. Isaria fumosorosea KCH J2 and Beauveria bassiana KCH J1.5 to obtain their novel glycosylated derivatives. Pharmacokinetics, drug-likeness, and biological activity of them were predicted using cheminformatics tools. 2-Chloro-2\'-hydroxychalcone, 3-chloro-2\'-hydroxychalcone, their main glycosylation products, and 2\'-hydrochychalcone were screened for antimicrobial activity against several microbial strains. The growth of Escherichia coli 10,536 was completely inhibited by chalcones with a chlorine atom and 3-chlorodihydrochalcone 2\'-O-β-D-(4″-O-methyl)-glucopyranoside. The strain Pseudomonas aeruginosa DSM 939 was the most resistant to the action of the tested compounds. However, chalcone aglycones and glycosides with a chlorine atom almost completely inhibited the growth of bacteria Staphylococcus aureus DSM 799 and yeast Candida albicans DSM 1386. The tested compounds had different effects on lactic acid bacteria depending on the tested species. In general, chlorinated chalcones were more effective in the inhibition of the tested microbial strains than their unchlorinated counterparts and aglycones were a little more effective than their glycosides.
摘要：
查尔酮是生物合成黄酮类化合物的中间产物，具有广泛的生物学特性，包括抗菌和抗癌活性。在其结构中引入氯原子和葡萄糖基部分可以增加其生物利用度，生物活性，和药理使用。组合的化学和生物技术方法可用于获得此类化合物。因此,2-氯-2'-羟基查耳酮和3-氯-2'-羟基查耳酮在两株丝状真菌的培养物中合成并生物转化，即镰刀菌KCHJ2和球孢白僵菌KCHJ1.5获得其新型糖基化衍生物。药代动力学，药物相似，并使用化学信息学工具预测它们的生物活性。2-氯-2'-羟基查耳酮，3-氯-2'-羟基查耳酮，它们的主要糖基化产物，并筛选了2'-氢chyclone对几种微生物菌株的抗菌活性。带有氯原子的查耳酮和3-氯二氢查耳酮2\'-O-β-D-（4“-O-甲基）-吡喃葡萄糖苷完全抑制了大肠杆菌10,536的生长。菌株铜绿假单胞菌DSM939对测试化合物的作用最具抗性。然而,具有氯原子的查尔酮苷元和糖苷几乎完全抑制了细菌金黄色葡萄球菌DSM799和白色念珠菌DSM1386的生长。取决于测试的物种,测试的化合物对乳酸菌具有不同的作用。总的来说,氯化查耳酮在抑制所测试的微生物菌株方面比未氯化的对应物更有效，而糖苷配基比其糖苷更有效。
