Department of Food Science and Biotechnology, Daegu University, Gyeongsan 38453, Republic of Korea.
Institute of Animal Medicine, College of Veterinary Medicine, Gyeongsang National University, Jinju 52828, Republic of Korea.
Bioorg Med Chem Lett. 2019 Aug 15;29(16):2079-2084. doi: 10.1016/j.bmcl.2019.07.008. Epub 2019 Jul 5.
Convenient structure modification of (+)-catechin (1) induced by nonthermal dielectric barrier discharge (DBD) plasma treatment afforded three novel methylene-linked flavan-3-ol oligomers, methylenetetracatechin (2), methylenetricatechin (3), and methylenedicatechin (4), together with two known catechin dimers, bis 8,8'-catechinylmethane (5) and bis 6,8'-catechinylmethane (6). The structures of the three new catechin oligomers 2-4 with methylene bridges were elucidated by detailed 1D- and 2D-NMR analysis, and the absolute configurations were established by the observation of circular dichroism (CD). The novel products 2 and 3 showed significantly enhanced anti-adipogenic capacities against both pancreatic lipase and differentiation of 3T3-L1 preadipocytes compared to the parent (+)-catechin.
非热等离子体处理（DBD）诱导（+）-儿茶素（1）的方便结构修饰，提供了三种新型的亚甲基连接黄烷-3-醇低聚物，即亚甲基四儿茶素（2）、亚甲基三儿茶素（3）和亚甲基二儿茶素（4），以及两种已知的儿茶素二聚体，双 8,8'-儿茶素基甲烷（5）和双 6,8'-儿茶素基甲烷（6）。通过详细的 1D 和 2D-NMR 分析，阐明了具有亚甲基桥的三种新型儿茶素低聚物 2-4 的结构，并通过圆二色性（CD）的观察确定了绝对构型。与母体（+）-儿茶素相比，新型产物 2 和 3 对胰腺脂肪酶和 3T3-L1 前脂肪细胞分化均显示出显著增强的抗脂肪生成能力。
