New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity

Phi Hung Nguyen; Trong Tuan Dao; Jayeon Kim; Do Tuan Phong; Derek Tantoh Ndinteh; Joseph Tanyi Mbafor; Won Keun Oh

doi:10.1016/j.bmc.2011.04.037

New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity

Phi Hung Nguyen, Trong Tuan Dao, Jayeon Kim, Do Tuan Phong, Derek Tantoh Ndinteh, Joseph Tanyi Mbafor, Won Keun Oh

31 Citations (Scopus)

Abstract

In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC₅₀ values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC ₅₀ 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC ₅₀ 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.

Original language	English
Journal	Bioorganic & Medicinal Chemistry
Volume	19
Issue number	11
Pages (from-to)	3378-83
Number of pages	6
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2011.04.037
Publication status	Published - 1 Jun 2011

Keywords

Circular Dichroism
Enzyme Inhibitors
Erythrina
Flavonoids
Humans
Magnetic Resonance Spectroscopy
Molecular Conformation
Plant Bark
Plant Roots
Protein Tyrosine Phosphatase, Non-Receptor Type 1
Journal Article
Research Support, Non-U.S. Gov't

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10.1016/j.bmc.2011.04.037

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@article{e5e5a94e0aa045db89ea6d8dba91a59f,

title = "New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity",

abstract = "In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC50 values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC 50 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC 50 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.",

keywords = "Circular Dichroism, Enzyme Inhibitors, Erythrina, Flavonoids, Humans, Magnetic Resonance Spectroscopy, Molecular Conformation, Plant Bark, Plant Roots, Protein Tyrosine Phosphatase, Non-Receptor Type 1, Journal Article, Research Support, Non-U.S. Gov't",

author = "Nguyen, {Phi Hung} and Dao, {Trong Tuan} and Jayeon Kim and Phong, {Do Tuan} and Ndinteh, {Derek Tantoh} and Mbafor, {Joseph Tanyi} and Oh, {Won Keun}",

year = "2011",

month = jun,

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doi = "10.1016/j.bmc.2011.04.037",

language = "English",

volume = "19",

pages = "3378--83",

journal = "Bioorganic & Medicinal Chemistry",

issn = "0968-0896",

publisher = "Pergamon Press",

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}

TY - JOUR

T1 - New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity

AU - Nguyen, Phi Hung

AU - Dao, Trong Tuan

AU - Kim, Jayeon

AU - Phong, Do Tuan

AU - Ndinteh, Derek Tantoh

AU - Mbafor, Joseph Tanyi

AU - Oh, Won Keun

PY - 2011/6/1

Y1 - 2011/6/1

N2 - In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC50 values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC 50 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC 50 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.

AB - In the course of our program to search for protein tyrosine phosphatase 1B (PTPB) inhibitors, five new 5-deoxyflavonoids along with eight known derivatives were isolated from EtOAc layer of the root bark of Erythrina abyssinica. Their structures were elucidated on the basis of spectroscopic (IR, UV, MS, CD, 1D- and 2D-NMR) and physicochemical analyses. All isolates exhibited moderate inhibitory effects on the enzyme assay with IC50 values ranging from 14.9 ± 1.6 to 98.1 ± 11.3 μM. Compounds with prenyl and methoxy groups in the B ring (1, 2, 4, 8, and 13) possessed strong activity (IC 50 14.9 ± 1.6 to 19.2 ± 1.1 μM), while compounds (3, 5, and 9) with 2,2-dimethylpyrano ring showed less inhibitory effect (IC 50 22.6 ± 2.3 to 72.9 ± 9.7 μM). These results suggest that prenyl and methoxy groups may be responsible for the increase on the activity of 5-deoxyflavonoids against PTP1B, but the presence of 2,2-dimethylpyrano ring on the B ring may be induced the decrease of PTP1B inhibitory activity.

KW - Circular Dichroism

KW - Enzyme Inhibitors

KW - Erythrina

KW - Flavonoids

KW - Humans

KW - Magnetic Resonance Spectroscopy

KW - Molecular Conformation

KW - Plant Bark

KW - Plant Roots

KW - Protein Tyrosine Phosphatase, Non-Receptor Type 1

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1016/j.bmc.2011.04.037

DO - 10.1016/j.bmc.2011.04.037

M3 - Journal article

C2 - 21571537

SN - 0968-0896

VL - 19

SP - 3378

EP - 3383

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 11

ER -

New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity

Abstract

Keywords

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