Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322-4105, USA.
Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322-4105, USA.
J Biosci Bioeng. 2024 Aug;138(2):144-152. doi: 10.1016/j.jbiosc.2024.05.009. Epub 2024 Jun 10.
Flavonoids comprise a group of natural compounds with diverse bioactivities; however, their low water solubility and limited bioavailability often impede their potential health benefits for humans. In this study, five derivatives, namely 2',5'-dihydroxyflavanone (1), 2'-dihydroxyflavanone-5'-O-4″-O-methyl-β-d-glucoside (2), 2'-dihydroxyflavanone-6-O-4″-O-methyl-β-d-glucoside (3), 2'-dihydroxyflavanone-3'-O-4″-O-methyl-β-d-glucoside (4) and hydroxyflavanone-2'-O-4″-O-methyl-β-d-glucoside (5), were biosynthesized from 2'-hydroxyflavanone through microbial transformation using Beauveria bassiana ATCC 7159. Product 1 was identified as a known compound while 2-5 were structurally characterized as new structures through extensive 1D and 2D NMR analysis. The water solubility of biotransformed products 1-5 was enhanced by 30-280 times compared to the substrate 2'-hydroxyflavanone. Moreover, the antioxidant assay revealed that 1 and 2 exhibited improved 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity relative to the substrate, decreasing the logIC from 8.08 ± 0.11 μM to 6.19 ± 0.08 μM and 7.15 ± 0.08 μM, respectively. Compound 5 displayed significantly improved anticancer activity compared to the substrate 2'-hydroxyflavanone against Glioblastoma 33 cancer stem cells, decreasing the IC from 25.05 μM to 10.59 μM. Overall, fungal biotransformation represents an effective tool to modify flavonoids for enhanced water solubility and bioactivities.
类黄酮是一组具有多种生物活性的天然化合物；然而，它们的低水溶性和有限的生物利用度常常阻碍了它们对人类的潜在健康益处。在这项研究中，五种衍生物，即 2'，5'-二羟基黄烷酮（1）、2'-二羟基黄烷酮-5'-O-4″-O-甲基-β-D-葡萄糖苷（2）、2'-二羟基黄烷酮-6-O-4″-O-甲基-β-D-葡萄糖苷（3）、2'-二羟基黄烷酮-3'-O-4″-O-甲基-β-D-葡萄糖苷（4）和羟基黄烷酮-2'-O-4″-O-甲基-β-D-葡萄糖苷（5），是通过利用白僵菌 ATCC 7159 对 2'-羟基黄烷酮进行微生物转化生物合成的。产物 1 被鉴定为已知化合物，而 2-5 通过广泛的 1D 和 2D NMR 分析被结构表征为新结构。与底物 2'-羟基黄烷酮相比，生物转化产物 1-5 的水溶性提高了 30-280 倍。此外，抗氧化测定表明，1 和 2 对 2,2-二苯基-1-苦基肼（DPPH）自由基清除活性的改善优于底物，使 logIC 从 8.08±0.11μM 分别降低到 6.19±0.08μM 和 7.15±0.08μM。与底物 2'-羟基黄烷酮相比，化合物 5 对神经胶质瘤 33 癌症干细胞的抗癌活性显著提高，使 IC 从 25.05μM 降低至 10.59μM。总的来说，真菌生物转化是一种有效的方法，可以修饰类黄酮以提高其水溶性和生物活性。
