Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations. / Liang, Chao; Ndi, Chi; Kjaerulff, Louise; Semple, Susan; Buirchell, Bevan; Coriani, Sonia; Møller, Birger Lindberg; Stærk, Dan.

In: Journal of Natural Products, Vol. 86, No. 4, 2023, p. 694–709.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Liang, C, Ndi, C, Kjaerulff, L, Semple, S, Buirchell, B, Coriani, S, Møller, BL & Stærk, D 2023, 'Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations', Journal of Natural Products, vol. 86, no. 4, pp. 694–709. https://doi.org/10.1021/acs.jnatprod.2c00692

APA

Liang, C., Ndi, C., Kjaerulff, L., Semple, S., Buirchell, B., Coriani, S., Møller, B. L., & Stærk, D. (2023). Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations. Journal of Natural Products, 86(4), 694–709. https://doi.org/10.1021/acs.jnatprod.2c00692

Vancouver

Liang C, Ndi C, Kjaerulff L, Semple S, Buirchell B, Coriani S et al. Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations. Journal of Natural Products. 2023;86(4):694–709. https://doi.org/10.1021/acs.jnatprod.2c00692

Author

Liang, Chao ; Ndi, Chi ; Kjaerulff, Louise ; Semple, Susan ; Buirchell, Bevan ; Coriani, Sonia ; Møller, Birger Lindberg ; Stærk, Dan. / Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations. In: Journal of Natural Products. 2023 ; Vol. 86, No. 4. pp. 694–709.

Bibtex

@article{8882fc4c47ae4e89a369619ffd97d813,
title = "Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations",
abstract = "Extracts of Eremophila phyllopoda subsp. phyllopoda showed α-glucosidase and PTP1B inhibitory activity with IC50 values of 19.6 and 13.6 μg/mL, respectively. High-resolution α-glucosidase/PTP1B/radical scavenging profiling was performed to establish a triple high-resolution inhibition profile that allowed direct pinpointing of the constituents responsible for one or more of the observed bioactivities. Subsequent targeted isolation and purification by analytical-scale HPLC led to the identification of 21 previously undescribed serrulatane diterpenoids, eremophyllanes A-U, as well as two known serrulatane diterpenoids, 1β-trihydroxyserrulatane (8) and 1α-trihydroxyserrulatane (10d), and five known furofuran lignans, (+)-piperitol (6), horsfieldin (7e), (―)-sesamin (9), (+)-sesamin (10h), and asarinin (10i). Their structures were elucidated by extensive analysis of HRMS and 1D and 2D NMR spectroscopic data. The relative configurations of the previously undescribed compounds were established by analysis of ROESY spectra as well as by DFT-GIAO NMR calculations followed by DP4+ probability analysis. The absolute configurations were determined by comparison of experimental and calculated ECD spectra. Serrulatane diterpenoids 7b and 14 exhibited α-glucosidase inhibitory activity with IC50 values of 28.4 and 64.2 μM respectively, while 11, 12, 14, and 15 exhibited PTP1B inhibitory activity with IC50 values ranging from 16.6 to 104.6 μM. Hypothetical routes for formation of all identified serrulatane diterpenoids are proposed.",
author = "Chao Liang and Chi Ndi and Louise Kjaerulff and Susan Semple and Bevan Buirchell and Sonia Coriani and M{\o}ller, {Birger Lindberg} and Dan St{\ae}rk",
year = "2023",
doi = "10.1021/acs.jnatprod.2c00692",
language = "English",
volume = "86",
pages = "694–709",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

T1 - Characterization of serrulatane diterpenoids in Eremophila phyllopoda subsp. phyllopoda by triple high-resolution α-glucosidase/PTP1B/radical scavenging profiling, NMR spectroscopy, DFT-GIAO NMR, and electronic circular dichroism calculations

AU - Liang, Chao

AU - Ndi, Chi

AU - Kjaerulff, Louise

AU - Semple, Susan

AU - Buirchell, Bevan

AU - Coriani, Sonia

AU - Møller, Birger Lindberg

AU - Stærk, Dan

PY - 2023

Y1 - 2023

N2 - Extracts of Eremophila phyllopoda subsp. phyllopoda showed α-glucosidase and PTP1B inhibitory activity with IC50 values of 19.6 and 13.6 μg/mL, respectively. High-resolution α-glucosidase/PTP1B/radical scavenging profiling was performed to establish a triple high-resolution inhibition profile that allowed direct pinpointing of the constituents responsible for one or more of the observed bioactivities. Subsequent targeted isolation and purification by analytical-scale HPLC led to the identification of 21 previously undescribed serrulatane diterpenoids, eremophyllanes A-U, as well as two known serrulatane diterpenoids, 1β-trihydroxyserrulatane (8) and 1α-trihydroxyserrulatane (10d), and five known furofuran lignans, (+)-piperitol (6), horsfieldin (7e), (―)-sesamin (9), (+)-sesamin (10h), and asarinin (10i). Their structures were elucidated by extensive analysis of HRMS and 1D and 2D NMR spectroscopic data. The relative configurations of the previously undescribed compounds were established by analysis of ROESY spectra as well as by DFT-GIAO NMR calculations followed by DP4+ probability analysis. The absolute configurations were determined by comparison of experimental and calculated ECD spectra. Serrulatane diterpenoids 7b and 14 exhibited α-glucosidase inhibitory activity with IC50 values of 28.4 and 64.2 μM respectively, while 11, 12, 14, and 15 exhibited PTP1B inhibitory activity with IC50 values ranging from 16.6 to 104.6 μM. Hypothetical routes for formation of all identified serrulatane diterpenoids are proposed.

AB - Extracts of Eremophila phyllopoda subsp. phyllopoda showed α-glucosidase and PTP1B inhibitory activity with IC50 values of 19.6 and 13.6 μg/mL, respectively. High-resolution α-glucosidase/PTP1B/radical scavenging profiling was performed to establish a triple high-resolution inhibition profile that allowed direct pinpointing of the constituents responsible for one or more of the observed bioactivities. Subsequent targeted isolation and purification by analytical-scale HPLC led to the identification of 21 previously undescribed serrulatane diterpenoids, eremophyllanes A-U, as well as two known serrulatane diterpenoids, 1β-trihydroxyserrulatane (8) and 1α-trihydroxyserrulatane (10d), and five known furofuran lignans, (+)-piperitol (6), horsfieldin (7e), (―)-sesamin (9), (+)-sesamin (10h), and asarinin (10i). Their structures were elucidated by extensive analysis of HRMS and 1D and 2D NMR spectroscopic data. The relative configurations of the previously undescribed compounds were established by analysis of ROESY spectra as well as by DFT-GIAO NMR calculations followed by DP4+ probability analysis. The absolute configurations were determined by comparison of experimental and calculated ECD spectra. Serrulatane diterpenoids 7b and 14 exhibited α-glucosidase inhibitory activity with IC50 values of 28.4 and 64.2 μM respectively, while 11, 12, 14, and 15 exhibited PTP1B inhibitory activity with IC50 values ranging from 16.6 to 104.6 μM. Hypothetical routes for formation of all identified serrulatane diterpenoids are proposed.

U2 - 10.1021/acs.jnatprod.2c00692

DO - 10.1021/acs.jnatprod.2c00692

M3 - Journal article

C2 - 36880726

VL - 86

SP - 694

EP - 709

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 4

ER -

ID: 336630818