Department of Food Science and Biotechnology, Daegu University, Gyeongsan, Republic of Korea.
Institute of Animal Medicine, College of Veterinary Medicine, Gyeongsang National University, Jinju, Republic of Korea.
Biosci Biotechnol Biochem. 2021 Nov 24;85(12):2352-2359. doi: 10.1093/bbb/zbab168.
Enzymatic structure modification of the representative chalcone phloretin (1) with polyphenol oxidase from Agaricus bisporus origin produced 2 new biphenyl-type phloreoxin (2) and phloreoxinone (3), and a previously undescribed (2R)-5,7,3',5'-tetrahydroxyflavanone (4). The structure of these new oxidized products 2-4 elucidated by interpreting the spectroscopic data (NMR and FABMS) containing the absolute stereochemistry is established by the analysis of the circular dichroism spectrum. Compared to the original phloretin, the new products (2) and (3) showed highly improved antiadipogenic potencies both toward pancreatic lipase and accumulation of 3T3-L1 cells. Also, phloreoxin (2) effectively inhibited the expression of C/EBPβ, PPARγ, and aP2 at the mRNA level in the 3T3 adipocytes. Thus, phloreoxin (2), containing a biphenyl moiety catalyzed by A. bisporus polyphenol oxidase, have the potential to influence the antiadipogenic capacity.
酶促结构修饰代表性查尔酮根皮素（1）与双孢蘑菇来源的多酚氧化酶一起产生了 2 种新的联苯型根皮素（2）和根皮素酮（3），以及一种以前未描述的（2R）-5,7,3',5'-四羟基黄烷酮（4）。这些新氧化产物 2-4 的结构通过解释包含绝对立体化学的光谱数据（NMR 和 FABMS）来阐明，并通过圆二色谱分析确定。与原始根皮素相比，新产物（2）和（3）对胰腺脂肪酶和 3T3-L1 细胞积累的抗脂肪生成能力均有显著提高。此外，根皮素（2）在 3T3 脂肪细胞中有效抑制 C/EBPβ、PPARγ 和 aP2 的 mRNA 水平表达。因此，含有双苯部分的根皮素（2），由双孢蘑菇多酚氧化酶催化，有可能影响抗脂肪生成能力。
