2(5H)-Furanone sesquiterpenes from Eremophila bignoniiflora: High-resolution inhibition profiling and PTP1B inhibitory activity

Yong Zhao; Louise Kjaerulff; Kenneth Thermann Kongstad; Allison Maree Heskes; Birger Lindberg Møller; Dan Stærk

doi:10.1016/j.phytochem.2019.112054

2(5H)-Furanone sesquiterpenes from Eremophila bignoniiflora: High-resolution inhibition profiling and PTP1B inhibitory activity

Yong Zhao, Louise Kjaerulff, Kenneth Thermann Kongstad, Allison Maree Heskes, Birger Lindberg Møller, Dan Stærk

Section for Plant Biochemistry

6 Citations (Scopus)

Abstract

Eremophila bignoniiflora is a shrub distributed throughout inland northern and eastern Australia, and it has been used in several medicinal applications by some Australian Aboriginal people. In our continued search for anti-diabetic constituents from natural resources, the crude ethyl acetate extract of E. bignoniiflora was found to have protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC₅₀ value of 23.9 ± 1.9 μg/mL. High-resolution PTP1B inhibition profiling combined with HRMS and NMR were subsequently used to investigate the individual compounds responsible for the observed bioactivity of the crude extract. This led to identification of five undescribed 2(5H)-furanone sesquiterpenes, together with 13 flavonoids and phenolic compounds. Dose-response curves of the isolated compounds revealed that two 2(5H)-furanone sesquiterpene cinnamates and three flavonoids exhibited moderate PTP1B inhibitory activity with IC₅₀ values from 41.4 ± 1.4 to 154.5 ± 8.9 μM.

Original language	English
Article number	112054
Journal	Phytochemistry
Volume	166
Pages (from-to)	1-8
ISSN	0031-9422
DOIs	https://doi.org/10.1016/j.phytochem.2019.112054
Publication status	Published - Oct 2019

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@article{4da04b305a4b435abeec80787f27d92b,

title = "2(5H)-Furanone sesquiterpenes from Eremophila bignoniiflora: High-resolution inhibition profiling and PTP1B inhibitory activity",

abstract = "Eremophila bignoniiflora is a shrub distributed throughout inland northern and eastern Australia, and it has been used in several medicinal applications by some Australian Aboriginal people. In our continued search for anti-diabetic constituents from natural resources, the crude ethyl acetate extract of E. bignoniiflora was found to have protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC50 value of 23.9 ± 1.9 μg/mL. High-resolution PTP1B inhibition profiling combined with HRMS and NMR were subsequently used to investigate the individual compounds responsible for the observed bioactivity of the crude extract. This led to identification of five undescribed 2(5H)-furanone sesquiterpenes, together with 13 flavonoids and phenolic compounds. Dose-response curves of the isolated compounds revealed that two 2(5H)-furanone sesquiterpene cinnamates and three flavonoids exhibited moderate PTP1B inhibitory activity with IC50 values from 41.4 ± 1.4 to 154.5 ± 8.9 μM.",

author = "Yong Zhao and Louise Kjaerulff and Kongstad, {Kenneth Thermann} and Heskes, {Allison Maree} and M{\o}ller, {Birger Lindberg} and Dan St{\ae}rk",

year = "2019",

month = oct,

doi = "10.1016/j.phytochem.2019.112054",

language = "English",

volume = "166",

pages = "1--8",

journal = "Phytochemistry",

issn = "0031-9422",

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T1 - 2(5H)-Furanone sesquiterpenes from Eremophila bignoniiflora

T2 - High-resolution inhibition profiling and PTP1B inhibitory activity

AU - Zhao, Yong

AU - Kjaerulff, Louise

AU - Kongstad, Kenneth Thermann

AU - Heskes, Allison Maree

AU - Møller, Birger Lindberg

AU - Stærk, Dan

PY - 2019/10

Y1 - 2019/10

N2 - Eremophila bignoniiflora is a shrub distributed throughout inland northern and eastern Australia, and it has been used in several medicinal applications by some Australian Aboriginal people. In our continued search for anti-diabetic constituents from natural resources, the crude ethyl acetate extract of E. bignoniiflora was found to have protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC50 value of 23.9 ± 1.9 μg/mL. High-resolution PTP1B inhibition profiling combined with HRMS and NMR were subsequently used to investigate the individual compounds responsible for the observed bioactivity of the crude extract. This led to identification of five undescribed 2(5H)-furanone sesquiterpenes, together with 13 flavonoids and phenolic compounds. Dose-response curves of the isolated compounds revealed that two 2(5H)-furanone sesquiterpene cinnamates and three flavonoids exhibited moderate PTP1B inhibitory activity with IC50 values from 41.4 ± 1.4 to 154.5 ± 8.9 μM.

AB - Eremophila bignoniiflora is a shrub distributed throughout inland northern and eastern Australia, and it has been used in several medicinal applications by some Australian Aboriginal people. In our continued search for anti-diabetic constituents from natural resources, the crude ethyl acetate extract of E. bignoniiflora was found to have protein-tyrosine phosphatase 1B (PTP1B) inhibitory activity with an IC50 value of 23.9 ± 1.9 μg/mL. High-resolution PTP1B inhibition profiling combined with HRMS and NMR were subsequently used to investigate the individual compounds responsible for the observed bioactivity of the crude extract. This led to identification of five undescribed 2(5H)-furanone sesquiterpenes, together with 13 flavonoids and phenolic compounds. Dose-response curves of the isolated compounds revealed that two 2(5H)-furanone sesquiterpene cinnamates and three flavonoids exhibited moderate PTP1B inhibitory activity with IC50 values from 41.4 ± 1.4 to 154.5 ± 8.9 μM.

U2 - 10.1016/j.phytochem.2019.112054

DO - 10.1016/j.phytochem.2019.112054

M3 - Journal article

C2 - 31284174

SN - 0031-9422

VL - 166

SP - 1

EP - 8

JO - Phytochemistry

JF - Phytochemistry

M1 - 112054

ER -

2(5H)-Furanone sesquiterpenes from Eremophila bignoniiflora: High-resolution inhibition profiling and PTP1B inhibitory activity

Abstract

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