Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities

Duc Hung Nguyen; U Min Seo; Bing Tian Zhao; Duc Dat Le; Su Hui Seong; Jae Sue Choi; Byung Sun Min; Mi Hee Woo

doi:10.1016/j.bioorg.2017.04.017

Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities

Bioorg Chem. 2017 Jun:72:293-300. doi: 10.1016/j.bioorg.2017.04.017. Epub 2017 Apr 30.

Authors

Duc Hung Nguyen¹, U Min Seo², Bing Tian Zhao², Duc Dat Le², Su Hui Seong³, Jae Sue Choi³, Byung Sun Min², Mi Hee Woo⁴

Affiliations

¹ College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea; Phutho College of Pharmacy, Viettri City, Phutho Province 290000, Viet Nam.
² College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea.
³ Department of Food Science & Nutrition, Pukyong National University, Busan 48513, Republic of Korea.
⁴ College of Pharmacy, Drug Research and Development Center, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea. Electronic address: [email protected].

PMID: 28499190
DOI: 10.1016/j.bioorg.2017.04.017

Abstract

A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa Ledeb. These compounds were evaluated for PTP1B inhibitory activity. Among them, compounds 9 and 18 displayed potential inhibitory activity against PTP1B with IC₅₀ values of 7.14±1.75 and 7.73±0.24μM, respectively. In addition, compound 1 showed significant inhibitory effect with an IC₅₀ value of 17.03±0.09μM. Furthermore, these compounds were tested in AChE inhibitory assays. Most of them were found to have moderate inhibitory effects, with IC₅₀ values ranging from 60.20±1.09 to 92.85±1.12μM. Except compounds 3, 8, and 18 were inactive.

Keywords: Acetylcholinesterase; Agriflavone; Agrimonia pilosa; Agritannin; Protein tyrosine phosphatase 1B.

Publication types

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

MeSH terms

Acetylcholinesterase / metabolism*
Agrimonia / chemistry*
Butyrylcholinesterase / metabolism
Carbonic Anhydrase I / antagonists & inhibitors
Carbonic Anhydrase I / metabolism
Carbonic Anhydrase II / antagonists & inhibitors
Carbonic Anhydrase II / metabolism
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / isolation & purification
Enzyme Inhibitors / pharmacology*
Flavonoids / chemistry
Flavonoids / isolation & purification
Flavonoids / pharmacology*
Humans
Hydrolyzable Tannins / chemistry
Hydrolyzable Tannins / isolation & purification
Hydrolyzable Tannins / pharmacology*
Molecular Structure
Plant Extracts / chemistry
Plant Extracts / isolation & purification
Plant Extracts / pharmacology*
Protein Tyrosine Phosphatases / antagonists & inhibitors*
Protein Tyrosine Phosphatases / metabolism
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Flavonoids
Hydrolyzable Tannins
Plant Extracts
ellagitannin
Acetylcholinesterase
Butyrylcholinesterase
Protein Tyrosine Phosphatases
Carbonic Anhydrase I
Carbonic Anhydrase II