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水飞蓟宾和2,3-脱氢水飞蓟宾二聚体的化学酶法合成。

Chemo-enzymatic synthesis of silybin and 2,3-dehydrosilybin dimers.

作者信息

Vavříková Eva, Vacek Jan, Valentová Kateřina, Marhol Petr, Ulrichová Jitka, Kuzma Marek, Křen Vladimír

机构信息

Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic.

Department of Medical Chemistry and Biochemistry, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, CZ-775 15 Olomouc, Czech Republic.

出版信息

Molecules. 2014 Apr 2;19(4):4115-34. doi: 10.3390/molecules19044115.

DOI:10.3390/molecules19044115
PMID:24699152
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271273/
Abstract

Divalent or multivalent molecules often show enhanced biological activity relative to the simple monomeric units. Here we present enzymatically and chemically prepared dimers of the flavonolignans silybin and 2,3-dehydrosilybin. Their electrochemical behavior was studied by in situ and ex situ square wave voltammetry. The oxidation of monomers and dimers was similar, but adsorption onto the electrode and cell surfaces was different. A 1,1-diphenyl-2-picrylhydrazyl (DPPH) and an inhibition of microsomal lipoperoxidation assay were performed with same trend of results for silybin and 2,3-dehydrosilybin dimers. Silybin dimer showed better activity than the monomer, while on the contrary 2,3-dehydrosilybin dimer presented weaker antioxidant/antilipoperoxidant activity than its monomer. Cytotoxicity was evaluated on human umbilical vein endothelial cells, normal human adult keratinocytes, mouse fibroblasts (BALB/c 3T3) and human liver hepatocellular carcinoma cell line (HepG2). Silybin dimer was more cytotoxic than the parent compound and in the case of 2,3-dehydrosilybin its dimer showed weaker cytotoxicity than the monomer.

摘要

相对于简单的单体单元，二价或多价分子通常表现出增强的生物活性。在此，我们展示了通过酶法和化学法制备的黄酮木脂素水飞蓟宾和2,3-脱氢水飞蓟宾的二聚体。通过原位和非原位方波伏安法研究了它们的电化学行为。单体和二聚体的氧化过程相似，但在电极和细胞表面的吸附情况不同。对水飞蓟宾和2,3-脱氢水飞蓟宾二聚体进行了1,1-二苯基-2-苦基肼基（DPPH）和微粒体脂质过氧化抑制试验，结果趋势相同。水飞蓟宾二聚体比单体表现出更好的活性，而相反，2,3-脱氢水飞蓟宾二聚体的抗氧化/抗脂质过氧化活性比其单体弱。在人脐静脉内皮细胞、正常成人人类角质形成细胞、小鼠成纤维细胞（BALB/c 3T3）和人肝癌细胞系（HepG2）上评估了细胞毒性。水飞蓟宾二聚体比母体化合物的细胞毒性更强，而对于2,3-脱氢水飞蓟宾，其二聚体的细胞毒性比单体弱。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/617a37cdcd8b/molecules-19-04115-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/9b7c0576dd7f/molecules-19-04115-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/29c0ca2d2cfd/molecules-19-04115-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/2d0d55c31648/molecules-19-04115-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/ff70fb95bcb6/molecules-19-04115-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/8efa3f277a04/molecules-19-04115-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/5aa98a455932/molecules-19-04115-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/617a37cdcd8b/molecules-19-04115-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/9b7c0576dd7f/molecules-19-04115-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/29c0ca2d2cfd/molecules-19-04115-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/2d0d55c31648/molecules-19-04115-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/ff70fb95bcb6/molecules-19-04115-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/8efa3f277a04/molecules-19-04115-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/5aa98a455932/molecules-19-04115-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e86/6271273/617a37cdcd8b/molecules-19-04115-g004.jpg

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