Identification and semi-synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist †

Changjin Lim; Jung Gyu Park; Kyo Bin Kang; Young Ger Suh

doi:10.3390/molecules24193487

Identification and semi-synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist ^†

Changjin Lim
, Jung Gyu Park
, Kyo Bin Kang
, Young Ger Suh^*

^*Corresponding author for this work

Department of Pharmacy

CHA University
Seoul National University
Sookmyung Women's University

Research output: Contribution to journal › Journal article › peer-review

3 Scopus citations

Abstract

The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic acid in three steps. In addition, we present the corrected NMR spectrum of 3-O-protocatechuoylceanothic acid based on our synthesis.

Original language	English
Article number	3487
Journal	Molecules
Volume	24
Issue number	19
DOIs	https://doi.org/10.3390/molecules24193487
State	Published - 2019.09.26

Keywords

3-O-protocatechuoylceanothic acid
Agonist
G protein-coupled receptor
GPR120
Semi-synthesis

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10.3390/molecules24193487

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title = "Identification and semi-synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist †",

abstract = "The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic acid in three steps. In addition, we present the corrected NMR spectrum of 3-O-protocatechuoylceanothic acid based on our synthesis.",

keywords = "3-O-protocatechuoylceanothic acid, Agonist, G protein-coupled receptor, GPR120, Semi-synthesis",

author = "Changjin Lim and Park, \{Jung Gyu\} and Kang, \{Kyo Bin\} and Suh, \{Young Ger\}",

note = "Publisher Copyright: {\textcopyright} 2019 by the authors.",

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day = "26",

doi = "10.3390/molecules24193487",

language = "English",

volume = "24",

journal = "Molecules",

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T1 - Identification and semi-synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist †

AU - Lim, Changjin

AU - Park, Jung Gyu

AU - Kang, Kyo Bin

AU - Suh, Young Ger

PY - 2019/9/26

Y1 - 2019/9/26

N2 - The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic acid in three steps. In addition, we present the corrected NMR spectrum of 3-O-protocatechuoylceanothic acid based on our synthesis.

AB - The identification and three step synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist, is described. This ceanothane-type triterpenoid was identified from the components of Ziziphus jujuba roots and was found to be a new GPR120 agonist with a novel structure. We synthetically converted ceanothic acid, which does not have GPR120 agonist activity, into 3-O-protocatechuoylceanothic acid in three steps. In addition, we present the corrected NMR spectrum of 3-O-protocatechuoylceanothic acid based on our synthesis.

KW - 3-O-protocatechuoylceanothic acid

KW - Agonist

KW - G protein-coupled receptor

KW - GPR120

KW - Semi-synthesis

UR - https://www.scopus.com/pages/publications/85072695370

U2 - 10.3390/molecules24193487

DO - 10.3390/molecules24193487

M3 - Journal article

C2 - 31561452

AN - SCOPUS:85072695370

SN - 1420-3049

VL - 24

JO - Molecules

JF - Molecules

IS - 19

M1 - 3487

ER -

Identification and semi-synthesis of 3-O-protocatechuoylceanothic acid, a novel and natural GPR120 agonist ^†

Abstract

Keywords

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