Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Standard

Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum. / Liang, Chao; Kjaerulff, Louise; Hansen, Paul Robert; Kongstad, Kenneth Thermann; Stærk, Dan.

I: Journal of Natural Products, Bind 84, 2021, s. 2454-2467.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Liang, C, Kjaerulff, L, Hansen, PR, Kongstad, KT & Stærk, D 2021, 'Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum', Journal of Natural Products, bind 84, s. 2454-2467. https://doi.org/10.1021/acs.jnatprod.1c00454

APA

Liang, C., Kjaerulff, L., Hansen, P. R., Kongstad, K. T., & Stærk, D. (2021). Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum. Journal of Natural Products, 84, 2454-2467. https://doi.org/10.1021/acs.jnatprod.1c00454

Vancouver

Liang C, Kjaerulff L, Hansen PR, Kongstad KT, Stærk D. Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum. Journal of Natural Products. 2021;84:2454-2467. https://doi.org/10.1021/acs.jnatprod.1c00454

Author

Liang, Chao ; Kjaerulff, Louise ; Hansen, Paul Robert ; Kongstad, Kenneth Thermann ; Stærk, Dan. / Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum. I: Journal of Natural Products. 2021 ; Bind 84. s. 2454-2467.

Bibtex

@article{525192b2e85c46a0978281c72197820c,
title = "Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum",
abstract = "Thirteen previously undescribed chromene meroterpenoids, capitachromenic acids A-M (3-6, 7a, 7b, 8a, 8b, 9a, 9b, 10a, 10b, and 11b), were identified from an ethyl acetate extract of Rhododendron capitatum, using dual high-resolution α-glucosidase and PTP1B inhibition profiling in combination with HPLC-PDA-HRMS-SPE-NMR. In addition, one known chromene meroterpenoid daurichromenic acid (15) and its biosynthetic precursor, grifolic acid (12), two C-methylated flavanones, (2S)-5,7,4'-trihydroxy-8-methylflavanone (1) and farrerol (2), and two triterpenoids, oleanolic acid (14a) and ursolic acid (14b) were identified. New structures were elucidated by extensive 1D and 2D NMR analysis, and absolute configurations of new chromene meroterpenoids were assigned by analysis of their ECD spectra on the basis of the empirical chromane/chromene helicity rule and from Rh2(OCOCF3)4-induced ECD spectra by applying the bulkiness rule. Compounds 5, 9a, 9b, 12, and 15 showed α-glucosidase inhibitory activity with IC50 values ranging from 8.0 to 93.5 μM, while compounds 3, 5, 8b, 9a, 9b, 10b, 11b, 12, and 15 showed PTP1B inhibitory activity with IC50 values ranging from 2.5 to 68.1 μM.",
author = "Chao Liang and Louise Kjaerulff and Hansen, {Paul Robert} and Kongstad, {Kenneth Thermann} and Dan St{\ae}rk",
year = "2021",
doi = "10.1021/acs.jnatprod.1c00454",
language = "English",
volume = "84",
pages = "2454--2467",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",

}

RIS

TY - JOUR

T1 - Dual high-resolution α-glucosidase and PTP1B profiling combined with HPLC-PDA-HRMS-SPE-NMR analysis for the identification of potentially antidiabetic chromene meroterpenoids in Rhododendron capitatum

AU - Liang, Chao

AU - Kjaerulff, Louise

AU - Hansen, Paul Robert

AU - Kongstad, Kenneth Thermann

AU - Stærk, Dan

PY - 2021

Y1 - 2021

N2 - Thirteen previously undescribed chromene meroterpenoids, capitachromenic acids A-M (3-6, 7a, 7b, 8a, 8b, 9a, 9b, 10a, 10b, and 11b), were identified from an ethyl acetate extract of Rhododendron capitatum, using dual high-resolution α-glucosidase and PTP1B inhibition profiling in combination with HPLC-PDA-HRMS-SPE-NMR. In addition, one known chromene meroterpenoid daurichromenic acid (15) and its biosynthetic precursor, grifolic acid (12), two C-methylated flavanones, (2S)-5,7,4'-trihydroxy-8-methylflavanone (1) and farrerol (2), and two triterpenoids, oleanolic acid (14a) and ursolic acid (14b) were identified. New structures were elucidated by extensive 1D and 2D NMR analysis, and absolute configurations of new chromene meroterpenoids were assigned by analysis of their ECD spectra on the basis of the empirical chromane/chromene helicity rule and from Rh2(OCOCF3)4-induced ECD spectra by applying the bulkiness rule. Compounds 5, 9a, 9b, 12, and 15 showed α-glucosidase inhibitory activity with IC50 values ranging from 8.0 to 93.5 μM, while compounds 3, 5, 8b, 9a, 9b, 10b, 11b, 12, and 15 showed PTP1B inhibitory activity with IC50 values ranging from 2.5 to 68.1 μM.

AB - Thirteen previously undescribed chromene meroterpenoids, capitachromenic acids A-M (3-6, 7a, 7b, 8a, 8b, 9a, 9b, 10a, 10b, and 11b), were identified from an ethyl acetate extract of Rhododendron capitatum, using dual high-resolution α-glucosidase and PTP1B inhibition profiling in combination with HPLC-PDA-HRMS-SPE-NMR. In addition, one known chromene meroterpenoid daurichromenic acid (15) and its biosynthetic precursor, grifolic acid (12), two C-methylated flavanones, (2S)-5,7,4'-trihydroxy-8-methylflavanone (1) and farrerol (2), and two triterpenoids, oleanolic acid (14a) and ursolic acid (14b) were identified. New structures were elucidated by extensive 1D and 2D NMR analysis, and absolute configurations of new chromene meroterpenoids were assigned by analysis of their ECD spectra on the basis of the empirical chromane/chromene helicity rule and from Rh2(OCOCF3)4-induced ECD spectra by applying the bulkiness rule. Compounds 5, 9a, 9b, 12, and 15 showed α-glucosidase inhibitory activity with IC50 values ranging from 8.0 to 93.5 μM, while compounds 3, 5, 8b, 9a, 9b, 10b, 11b, 12, and 15 showed PTP1B inhibitory activity with IC50 values ranging from 2.5 to 68.1 μM.

U2 - 10.1021/acs.jnatprod.1c00454

DO - 10.1021/acs.jnatprod.1c00454

M3 - Journal article

C2 - 34460246

VL - 84

SP - 2454

EP - 2467

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

ER -

ID: 275446280