Synthesis of water-soluble ester-linked ursolic acid–gallic acid hybrids with various hydrolytic stabilities

Synthesis of water-soluble ester-linked ursolic acid–gallic acid hybrids with various hydrolytic stabilities Full article

Journal

Synthetic Communications
ISSN: 0039-7911 , E-ISSN: 1532-2432

Output data

Year: 2021, Volume: 51, Number: 16, Pages: 2466-2477 Pages count : 12 DOI: 10.1080/00397911.2021.1939057

Tags

antioxidant; ester-type hybrids; gallic acid; Ursolic acid; water solubility

Authors

Popov Sergey A. ¹ , Wang Chengzhang ² , Qi Zhiwen ² , Shults Elvira E. ¹ , Turks Māris ³

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Novosibirsk, Russian Federation
2	Chinese Academy of Forestry, Institute of Chemical Industry of Forest Products, Nanjing, China
3	Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, Riga, Latvia

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 (∼0.5 mg/mL) of novel hybrids containing both carboxyl group and hydroxyls at aromatic moiety were found. © 2021 Taylor & Francis Group, LLC.

Popov S.A. , Wang C. , Qi Z. , Shults E.E. , Turks M.
Synthesis of water-soluble ester-linked ursolic acid–gallic acid hybrids with various hydrolytic stabilities
Synthetic Communications. 2021. V.51. N16. P.2466-2477. DOI: 10.1080/00397911.2021.1939057 WOS Scopus РИНЦ

Published online:

Jun 27, 2021

Web of science	WOS:000667510400001
Scopus	2-s2.0-85110790274
Elibrary	46941465
OpenAlex	W3177188508