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

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

3 Цитирования (Scopus)

Аннотация

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%.

Язык оригинала	английский
Страницы (с-по)	1052-1060
Число страниц	9
Журнал	Russian Chemical Bulletin
Том	68
Номер выпуска	5
DOI	https://doi.org/10.1007/s11172-019-2519-y
Состояние	Опубликовано - 1 мая 2019

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10.1007/s11172-019-2519-y

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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. В: Russian Chemical Bulletin. 2019 ; Том 68, № 5. стр. 1052-1060.

@article{6720030895644a1098ec44ba132523fc,

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,

day = "1",

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

language = "English",

volume = "68",

pages = "1052--1060",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer Nature",

number = "5",

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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, том. 68, № 5, стр. 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.

В: Russian Chemical Bulletin, Том 68, № 5, 01.05.2019, стр. 1052-1060.

Результат исследования: Научные публикации в периодических изданиях › статья › рецензирование

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%.

KW - activity

KW - antifungal

KW - berberine

KW - berberrubine

KW - cholesterol

KW - Cryptococcus neoformans

KW - cytotoxicity

KW - hyperlipidemia

KW - sulfonate

KW - BERBERINE

KW - ANTIMICROBIAL ACTIVITY

UR - http://www.scopus.com/inward/record.url?scp=85067051044&partnerID=8YFLogxK

U2 - 10.1007/s11172-019-2519-y

DO - 10.1007/s11172-019-2519-y

M3 - Article

AN - SCOPUS:85067051044

VL - 68

SP - 1052

EP - 1060

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 5

ER -