Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates

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

doi:10.1007/s11172-019-2519-y

Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates

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

Research output: Contribution to journal › Article › peer-review

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Abstract

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 μg mL⁻¹, tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3±3.5%.

Original language	English
Pages (from-to)	1052-1060
Number of pages	9
Journal	Russian Chemical Bulletin
Volume	68
Issue number	5
DOIs	https://doi.org/10.1007/s11172-019-2519-y
Publication status	Published - 1 May 2019

Keywords

activity
antifungal
berberine
berberrubine
cholesterol
Cryptococcus neoformans
cytotoxicity
hyperlipidemia
sulfonate
BERBERINE
ANTIMICROBIAL ACTIVITY

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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. (2019). Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates. Russian Chemical Bulletin, 68(5), 1052-1060. https://doi.org/10.1007/s11172-019-2519-y

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. In: Russian Chemical Bulletin. 2019 ; Vol. 68, No. 5. pp. 1052-1060.

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title = "Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates",

abstract = "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{\textquoteright}-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 μg mL−1, tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3±3.5%.",

keywords = "activity, antifungal, berberine, berberrubine, cholesterol, Cryptococcus neoformans, cytotoxicity, hyperlipidemia, sulfonate, BERBERINE, ANTIMICROBIAL ACTIVITY",

author = "Nechepurenko, {I. V.} and Shirokova, {E. D.} and Khvostov, {M. V.} and Frolova, {T. S.} and Sinitsyna, {O. I.} and Maksimov, {A. M.} and Bredikhin, {R. A.} and Komarova, {N. I.} and Fadeev, {D. S.} and Luzina, {O. A.} and Tolstikova, {T. G.} and Salakhutdinova, {N. F.}",

year = "2019",

month = may,

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doi = "10.1007/s11172-019-2519-y",

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Nechepurenko, IV, Shirokova, ED , Khvostov, MV , Frolova, TS , Sinitsyna, OI, Maksimov, AM, Bredikhin, RA, Komarova, NI, Fadeev, DS, Luzina, OA, Tolstikova, TG & Salakhutdinova, NF 2019, 'Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates', Russian Chemical Bulletin, vol. 68, no. 5, pp. 1052-1060. https://doi.org/10.1007/s11172-019-2519-y

Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates. / 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.

In: Russian Chemical Bulletin, Vol. 68, No. 5, 01.05.2019, p. 1052-1060.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis, hypolipidemic and antifungal activity of tetrahydroberberrubine sulfonates

AU - Nechepurenko, I. V.

AU - Shirokova, E. D.

AU - Khvostov, M. V.

AU - Frolova, T. S.

AU - Sinitsyna, O. I.

AU - Maksimov, A. M.

AU - Bredikhin, R. A.

AU - Komarova, N. I.

AU - Fadeev, D. S.

AU - Luzina, O. A.

AU - Tolstikova, T. G.

AU - Salakhutdinova, N. F.

PY - 2019/5/1

Y1 - 2019/5/1

N2 - 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 μg mL−1, tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3±3.5%.

AB - 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 μg mL−1, tetrahydroberberrubine 9-O-pentafluorobenzenesulfonate inhibits the growth of the fungus Cryptococcus neoformans by 81.3±3.5%.

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KW - antifungal

KW - berberine

KW - berberrubine

KW - cholesterol

KW - Cryptococcus neoformans

KW - cytotoxicity

KW - hyperlipidemia

KW - sulfonate

KW - BERBERINE

KW - ANTIMICROBIAL ACTIVITY

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U2 - 10.1007/s11172-019-2519-y

DO - 10.1007/s11172-019-2519-y

M3 - Article

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VL - 68

SP - 1052

EP - 1060

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

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ER -