New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

Phi Hung Nguyen; Govinda Sharma; Trong Tuan Dao; Mohammad Nasir Uddin; Keon Wook Kang; Derek Tantoh Ndinteh; Joseph Tanyi Mbafor; Won Keun Oh

doi:10.1016/j.bmc.2012.08.024

New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

Phi Hung Nguyen
, Govinda Sharma
, Trong Tuan Dao
, Mohammad Nasir Uddin
, Keon Wook Kang
, Derek Tantoh Ndinteh
, Joseph Tanyi Mbafor
, Won Keun Oh

Research output: Contribution to journal › Article › peer-review

46 Citations (Scopus)

Abstract

Bioassay-guided fractionation of the EtOAc extract of the root of Erythrina addisoniae (Leguminosae) resulted in the isolation of four new (1-4), along with 2 known prenylated isoflavonoids (5-6). The structures of the isolates were assigned on the basis of spectroscopic data analysis, focusing on interpretation of 1D and 2D NMR, and MS data. All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), as well as their growth inhibition on MCF7, adriamycin-resistant MCF7 (MCF7/ADR), and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.6 ± 0.3 to 24.2 ± 2.1 μM) showed potential cytotoxic activity (IC(50) values ranging from 3.97 ± 0.17 to 11.4 ± 1.9 μM). Taken together, our data suggest that prenylated isoflavonoids, especially the isoflavone-type skeleton could be considered as new lead compounds against breast cancer via PTP1B inhibition.

Original language	English
Pages (from-to)	6459-6464
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	21
DOIs	https://doi.org/10.1016/j.bmc.2012.08.024
Publication status	Published - 1 Nov 2012
Externally published	Yes

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10.1016/j.bmc.2012.08.024

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@article{fc2bbfc2378a48bfaf3578ce0d2cb83d,

title = "New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae",

abstract = "Bioassay-guided fractionation of the EtOAc extract of the root of Erythrina addisoniae (Leguminosae) resulted in the isolation of four new (1-4), along with 2 known prenylated isoflavonoids (5-6). The structures of the isolates were assigned on the basis of spectroscopic data analysis, focusing on interpretation of 1D and 2D NMR, and MS data. All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), as well as their growth inhibition on MCF7, adriamycin-resistant MCF7 (MCF7/ADR), and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.6 ± 0.3 to 24.2 ± 2.1 μM) showed potential cytotoxic activity (IC(50) values ranging from 3.97 ± 0.17 to 11.4 ± 1.9 μM). Taken together, our data suggest that prenylated isoflavonoids, especially the isoflavone-type skeleton could be considered as new lead compounds against breast cancer via PTP1B inhibition.",

keywords = "Antineoplastic Agents, Phytogenic/chemistry, Cell Proliferation/drug effects, Cell Survival/drug effects, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Enzyme Inhibitors/chemistry, Erythrina/chemistry, Humans, Isoflavones/chemistry, MCF-7 Cells, Molecular Structure, Plant Extracts/chemistry, Plant Roots/chemistry, Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists \& inhibitors, Recombinant Proteins/antagonists \& inhibitors, Structure-Activity Relationship, Tumor Cells, Cultured",

author = "Nguyen, \{Phi Hung\} and Govinda Sharma and Dao, \{Trong Tuan\} and Uddin, \{Mohammad Nasir\} and Kang, \{Keon Wook\} and Ndinteh, \{Derek Tantoh\} and Mbafor, \{Joseph Tanyi\} and Oh, \{Won Keun\}",

year = "2012",

month = nov,

day = "1",

doi = "10.1016/j.bmc.2012.08.024",

language = "English",

volume = "20",

pages = "6459--6464",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "21",

}

TY - JOUR

T1 - New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

AU - Nguyen, Phi Hung

AU - Sharma, Govinda

AU - Dao, Trong Tuan

AU - Uddin, Mohammad Nasir

AU - Kang, Keon Wook

AU - Ndinteh, Derek Tantoh

AU - Mbafor, Joseph Tanyi

AU - Oh, Won Keun

PY - 2012/11/1

Y1 - 2012/11/1

N2 - Bioassay-guided fractionation of the EtOAc extract of the root of Erythrina addisoniae (Leguminosae) resulted in the isolation of four new (1-4), along with 2 known prenylated isoflavonoids (5-6). The structures of the isolates were assigned on the basis of spectroscopic data analysis, focusing on interpretation of 1D and 2D NMR, and MS data. All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), as well as their growth inhibition on MCF7, adriamycin-resistant MCF7 (MCF7/ADR), and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.6 ± 0.3 to 24.2 ± 2.1 μM) showed potential cytotoxic activity (IC(50) values ranging from 3.97 ± 0.17 to 11.4 ± 1.9 μM). Taken together, our data suggest that prenylated isoflavonoids, especially the isoflavone-type skeleton could be considered as new lead compounds against breast cancer via PTP1B inhibition.

AB - Bioassay-guided fractionation of the EtOAc extract of the root of Erythrina addisoniae (Leguminosae) resulted in the isolation of four new (1-4), along with 2 known prenylated isoflavonoids (5-6). The structures of the isolates were assigned on the basis of spectroscopic data analysis, focusing on interpretation of 1D and 2D NMR, and MS data. All the isolates were evaluated for their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B), as well as their growth inhibition on MCF7, adriamycin-resistant MCF7 (MCF7/ADR), and MDA-MB-231 breast cancer cell lines. Compounds which exhibited PTP1B inhibitory activity (IC(50) values ranging from 4.6 ± 0.3 to 24.2 ± 2.1 μM) showed potential cytotoxic activity (IC(50) values ranging from 3.97 ± 0.17 to 11.4 ± 1.9 μM). Taken together, our data suggest that prenylated isoflavonoids, especially the isoflavone-type skeleton could be considered as new lead compounds against breast cancer via PTP1B inhibition.

KW - Antineoplastic Agents, Phytogenic/chemistry

KW - Cell Proliferation/drug effects

KW - Cell Survival/drug effects

KW - Dose-Response Relationship, Drug

KW - Drug Screening Assays, Antitumor

KW - Enzyme Inhibitors/chemistry

KW - Erythrina/chemistry

KW - Humans

KW - Isoflavones/chemistry

KW - MCF-7 Cells

KW - Molecular Structure

KW - Plant Extracts/chemistry

KW - Plant Roots/chemistry

KW - Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors

KW - Recombinant Proteins/antagonists & inhibitors

KW - Structure-Activity Relationship

KW - Tumor Cells, Cultured

U2 - 10.1016/j.bmc.2012.08.024

DO - 10.1016/j.bmc.2012.08.024

M3 - Article

C2 - 23022281

SN - 0968-0896

VL - 20

SP - 6459

EP - 6464

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 21

ER -

New prenylated isoflavonoids as protein tyrosine phosphatase 1B (PTP1B) inhibitors from Erythrina addisoniae

Abstract

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