文献类型：期刊文献

英文题名：Synthesis of water-soluble ester-linked ursolic acid-gallic acid hybrids with various hydrolytic stabilities

作者：Popov, Sergey A.[1] Wang, Chengzhang[2] Qi, Zhiwen[2] Shults, Elvira E.[1] Turks, Maris[3]

第一作者：Popov, Sergey A.

通信作者：Popov, SA[1]

机构：[1]Novosibirsk Inst Organ Chem, Novosibirsk, Russia;[2]Chinese Acad Forestry, Inst Chem Ind Forest Prod, Nanjing, Peoples R China;[3]Riga Tech Univ, Fac Mat Sci & Appl Chem, Inst Technol Organ Chem, Riga, Latvia

年份：2021

卷号：51

期号：16

起止页码：2466-2477

外文期刊名：SYNTHETIC COMMUNICATIONS

收录：;Scopus(收录号：2-s2.0-85110790274);WOS:【SCI-EXPANDED(收录号:WOS:000667510400001)】；

基金：This research was financially supported by the ERA.Net RUS Plus project #RUS_ST2017-139 "AnticancerBet" (Foundation of Basic Research Grant 18-53-76001) and by Federal programs AAAA-A21-121011490016-8 and AAAA-A21-121011490015-1.

语种：英文

外文关键词：Ursolic acid; gallic acid; ester-type hybrids; antioxidant; water solubility

摘要：To obtain derivatives of ursolic acid with improved water solubility and antioxidant activity, new ester-linked hybrids of ursolic acid and gallic acid were synthesized. In the reaction of methyl gallate with ursoloyl chloride acetate, both mono- and diacylation products were obtained. To prepare mono-alkylated and mono-acylated derivatives of gallic acid, 4,5-O-methoxymethylene-protected methyl gallate was used. It was found that ursolic-gallic acid hybrids containing phenolic ester linkage readily underwent hydrolysis at C-28 of triterpenoid. The dioxolane protection allowed selective hydrolysis of the methyl ester at the aromatic moiety of the hybrid compound leaving intact the labile C-28 ester at the triterpenoid moiety. The hybrids possessing an ester-ether linker (terpenoid-COO-CH2CH2-O-aryl) are stable to the hydrolysis. The majority of the obtained ursolic-gallic acid hybrids containing free phenolic hydroxyl groups possess excellent antioxidant activity. Notable water solubilities (similar to 0.5mg/mL) of novel hybrids containing both carboxyl group and hydroxyls at aromatic moiety were found.