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
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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
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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