(−)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

Jang Hoon Kim; Sang Hyun Lee; Hyun Woo Lee; Ya Nan Sun; Won Hee Jang; Seo Young Yang; Hae Dong Jang; Young Ho Kim

doi:10.1016/j.ijbiomac.2016.06.069

(−)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

Jang Hoon Kim
, Sang Hyun Lee
, Hyun Woo Lee
, Ya Nan Sun
, Won Hee Jang
, Seo Young Yang
, Hae Dong Jang
, Young Ho Kim

Department of Biology Education

Chungnam National University
United States Food and Drug Administration
Hannam University

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

32 Scopus citations

Abstract

Cholinesterase inhibitors block the bioconversion of neurotransmitters by cholinesterase in the nervous system. Epicatechin derivatives (1, 3 and 5), polyphenols (6 and 7) from Orostachys japonicus, and catechin derivatives (2 and 4) from our in-house library were evaluated for their inhibitory activity on cholinesterase. Compound 5 exhibited IC₅₀ values of 58.3 ± 2.4 and 17.8 ± 3.8 μg/mL on AChE and BuChE, respectively. Compound 5 inhibited BuChE more strongly than AChE through a competitive behavior. In silico binding positions of 5 in the active site were predicted using Autodock 4.2 and processed in a 10000-ps molecular dynamics simulation to assess the stability of compound 5 binding.

Original language	English
Pages (from-to)	1033-1039
Number of pages	7
Journal	International Journal of Biological Macromolecules
Volume	91
DOIs	https://doi.org/10.1016/j.ijbiomac.2016.06.069
State	Published - 1 Oct 2016

Keywords

Cholinesterase
Competitive inhibitor
Crassulaceae
Molecular dymanics
Orostachys japonicus A. berger

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10.1016/j.ijbiomac.2016.06.069

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title = "(−)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase",

abstract = "Cholinesterase inhibitors block the bioconversion of neurotransmitters by cholinesterase in the nervous system. Epicatechin derivatives (1, 3 and 5), polyphenols (6 and 7) from Orostachys japonicus, and catechin derivatives (2 and 4) from our in-house library were evaluated for their inhibitory activity on cholinesterase. Compound 5 exhibited IC50 values of 58.3 ± 2.4 and 17.8 ± 3.8 μg/mL on AChE and BuChE, respectively. Compound 5 inhibited BuChE more strongly than AChE through a competitive behavior. In silico binding positions of 5 in the active site were predicted using Autodock 4.2 and processed in a 10000-ps molecular dynamics simulation to assess the stability of compound 5 binding.",

keywords = "Cholinesterase, Competitive inhibitor, Crassulaceae, Molecular dymanics, Orostachys japonicus A. berger",

author = "Kim, \{Jang Hoon\} and Lee, \{Sang Hyun\} and Lee, \{Hyun Woo\} and Sun, \{Ya Nan\} and Jang, \{Won Hee\} and Yang, \{Seo Young\} and Jang, \{Hae Dong\} and Kim, \{Young Ho\}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier B.V.",

year = "2016",

month = oct,

day = "1",

doi = "10.1016/j.ijbiomac.2016.06.069",

language = "English",

volume = "91",

pages = "1033--1039",

journal = "International Journal of Biological Macromolecules",

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T1 - (−)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

AU - Kim, Jang Hoon

AU - Lee, Sang Hyun

AU - Lee, Hyun Woo

AU - Sun, Ya Nan

AU - Jang, Won Hee

AU - Yang, Seo Young

AU - Jang, Hae Dong

AU - Kim, Young Ho

PY - 2016/10/1

Y1 - 2016/10/1

N2 - Cholinesterase inhibitors block the bioconversion of neurotransmitters by cholinesterase in the nervous system. Epicatechin derivatives (1, 3 and 5), polyphenols (6 and 7) from Orostachys japonicus, and catechin derivatives (2 and 4) from our in-house library were evaluated for their inhibitory activity on cholinesterase. Compound 5 exhibited IC50 values of 58.3 ± 2.4 and 17.8 ± 3.8 μg/mL on AChE and BuChE, respectively. Compound 5 inhibited BuChE more strongly than AChE through a competitive behavior. In silico binding positions of 5 in the active site were predicted using Autodock 4.2 and processed in a 10000-ps molecular dynamics simulation to assess the stability of compound 5 binding.

AB - Cholinesterase inhibitors block the bioconversion of neurotransmitters by cholinesterase in the nervous system. Epicatechin derivatives (1, 3 and 5), polyphenols (6 and 7) from Orostachys japonicus, and catechin derivatives (2 and 4) from our in-house library were evaluated for their inhibitory activity on cholinesterase. Compound 5 exhibited IC50 values of 58.3 ± 2.4 and 17.8 ± 3.8 μg/mL on AChE and BuChE, respectively. Compound 5 inhibited BuChE more strongly than AChE through a competitive behavior. In silico binding positions of 5 in the active site were predicted using Autodock 4.2 and processed in a 10000-ps molecular dynamics simulation to assess the stability of compound 5 binding.

KW - Cholinesterase

KW - Competitive inhibitor

KW - Crassulaceae

KW - Molecular dymanics

KW - Orostachys japonicus A. berger

UR - https://www.scopus.com/pages/publications/84976873404

U2 - 10.1016/j.ijbiomac.2016.06.069

DO - 10.1016/j.ijbiomac.2016.06.069

M3 - Article

C2 - 27341781

AN - SCOPUS:84976873404

SN - 0141-8130

VL - 91

SP - 1033

EP - 1039

JO - International Journal of Biological Macromolecules

JF - International Journal of Biological Macromolecules

ER -

(−)-Epicatechin derivate from Orostachys japonicus as potential inhibitor of the human butyrylcholinesterase

Abstract

Keywords

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