Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates

Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates Full article

Journal

Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171

Output data

Year: 2019, Volume: 68, Number: 5, Pages: 1052-1060 Pages count : 9 DOI: 10.1007/s11172-019-2519-y

Tags

berberine; berberrubine; sulfonate; cholesterol; hyperlipidemia; antifungal; activity; Cryptococcus neoformans; cytotoxicity

Authors

Nechepurenko I.V. ¹ , Shirokova E.D. ^1,2 , Khvostov M.V. ^1,2 , Frolova T.S. ^2,3 , Sinitsyna O.I. ^2,3 , Maksimov A.M. ¹ , Bredikhin R.A. ¹ , Komarova N.I. ¹ , Fadeev D.S. ¹ , Luzina O.A. ¹ , Tolstikova T.G. ¹ , Salakhutdinova N.F. ^1,2

Affiliations

1	Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, 9 Prosp Akad Lavrentieva, Novosibirsk 630090, Russia
2	Novosibirsk State Univ, 2 Ul Pirogova, Novosibirsk 630090, Russia
3	Russian Acad Sci, Branch, Inst Cytol & Genet, 10 Prosp Akad Lavrentieva, Novosibirsk 630090, Russia

The paper describes the synthesis of new tetrahydroberberrubine derivatives containing polyfl uorophenyl- or alkylsulfonate groups at the O(9) position as well as those containing or not containing a bromine atom at the C(12) position. In a model of acute Triton-induced hyperlipidemia, tetrahydroberberrubine 9-O-(heptafluoro-4'-toluene)sulfonate was shown to reduce the cholesterol level by 23.5%, which is comparable with the eff ect of Simvastatin. At a concentration of 32 g mL(-1), tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3 +/- 3.5%.

Nechepurenko I.V. , Shirokova E.D. , Khvostov M.V. , Frolova T.S. , Sinitsyna O.I. , Maksimov A.M. , Bredikhin R.A. , Komarova N.I. , Fadeev D.S. , Luzina O.A. , Tolstikova T.G. , Salakhutdinova N.F.
Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates
Russian Chemical Bulletin. 2019. V.68. N5. P.1052-1060. DOI: 10.1007/s11172-019-2519-y WOS Scopus РИНЦ

Нечепуренко И.В. , Гладкова Е.Д. , Хвостов М.В. , Фролова Т.С. , Синицына О.И. , Максимов А.М. , Бредихин Р.А. , Комарова Н.И. , Фадеев Д.С. , Лузина О.А. , Толстикова Т.Г. , Салахутдинов Н.Ф.
Синтез, гиполипидемическая и противогрибковая активность сульфонатов тетрагидроберберрубина
Известия Академии наук. Серия химическая.(RUSS CHEM B+). 2019. №5. С.1052-1060. РИНЦ

Submitted:	Jan 25, 2019
Accepted:	Mar 22, 2019
Published print:	Jun 11, 2019
Published online:	Jun 11, 2019

Web of science	WOS:000471201700017
Scopus	2-s2.0-85067051044
Elibrary	41628568
OpenAlex	W2950110168