Carthamusuchuric acid, an enolic glucoside of phenylpyruvic acid from the florets of Carthamus tinctorius and anti-adipogenic phenolic compounds

Su Cheol Baek; Bum Soo Lee; Sang Ah Yi; Jaecheol Lee; Ki Hyun Kim

doi:10.1016/j.tetlet.2020.152237

Carthamusuchuric acid, an enolic glucoside of phenylpyruvic acid from the florets of Carthamus tinctorius and anti-adipogenic phenolic compounds

Su Cheol Baek, Bum Soo Lee, Sang Ah Yi, Jaecheol Lee, Ki Hyun Kim

Department of Pharmacy

Sungkyunkwan University

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

4 Scopus citations

Abstract

A new unique enolic glucoside of phenylpyruvic acid, carthamusuchuric acid (1), and five known phenolic compounds (2–6) were isolated from the florets of Carthamus tinctorius. The structure of the new compound was elucidated by extensive spectroscopic analyses using one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry, and enzymatic hydrolysis. The anti-adipogenic activity of compounds 1–6 was evaluated by staining lipid droplets in 3T3-L1 preadipocytes with Oil Red O and assessing mRNA expression of adipocyte markers. The results showed that compounds 2 and 4 inhibited the differentiation of 3T3-L1 preadipocytes to adipocytes.

Original language	English
Article number	152237
Journal	Tetrahedron Letters
Volume	61
Issue number	34
DOIs	https://doi.org/10.1016/j.tetlet.2020.152237
State	Published - 20 Aug 2020

Keywords

Adipogenesis
Carthamus tinctorius
NMR
Phenylpyruvic acid

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title = "Carthamusuchuric acid, an enolic glucoside of phenylpyruvic acid from the florets of Carthamus tinctorius and anti-adipogenic phenolic compounds",

abstract = "A new unique enolic glucoside of phenylpyruvic acid, carthamusuchuric acid (1), and five known phenolic compounds (2–6) were isolated from the florets of Carthamus tinctorius. The structure of the new compound was elucidated by extensive spectroscopic analyses using one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry, and enzymatic hydrolysis. The anti-adipogenic activity of compounds 1–6 was evaluated by staining lipid droplets in 3T3-L1 preadipocytes with Oil Red O and assessing mRNA expression of adipocyte markers. The results showed that compounds 2 and 4 inhibited the differentiation of 3T3-L1 preadipocytes to adipocytes.",

keywords = "Adipogenesis, Carthamus tinctorius, NMR, Phenylpyruvic acid",

author = "Baek, \{Su Cheol\} and Lee, \{Bum Soo\} and Yi, \{Sang Ah\} and Jaecheol Lee and Kim, \{Ki Hyun\}",

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doi = "10.1016/j.tetlet.2020.152237",

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T1 - Carthamusuchuric acid, an enolic glucoside of phenylpyruvic acid from the florets of Carthamus tinctorius and anti-adipogenic phenolic compounds

AU - Baek, Su Cheol

AU - Lee, Bum Soo

AU - Yi, Sang Ah

AU - Lee, Jaecheol

AU - Kim, Ki Hyun

PY - 2020/8/20

Y1 - 2020/8/20

N2 - A new unique enolic glucoside of phenylpyruvic acid, carthamusuchuric acid (1), and five known phenolic compounds (2–6) were isolated from the florets of Carthamus tinctorius. The structure of the new compound was elucidated by extensive spectroscopic analyses using one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry, and enzymatic hydrolysis. The anti-adipogenic activity of compounds 1–6 was evaluated by staining lipid droplets in 3T3-L1 preadipocytes with Oil Red O and assessing mRNA expression of adipocyte markers. The results showed that compounds 2 and 4 inhibited the differentiation of 3T3-L1 preadipocytes to adipocytes.

AB - A new unique enolic glucoside of phenylpyruvic acid, carthamusuchuric acid (1), and five known phenolic compounds (2–6) were isolated from the florets of Carthamus tinctorius. The structure of the new compound was elucidated by extensive spectroscopic analyses using one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, high-resolution electrospray ionization mass spectrometry, and enzymatic hydrolysis. The anti-adipogenic activity of compounds 1–6 was evaluated by staining lipid droplets in 3T3-L1 preadipocytes with Oil Red O and assessing mRNA expression of adipocyte markers. The results showed that compounds 2 and 4 inhibited the differentiation of 3T3-L1 preadipocytes to adipocytes.

KW - Adipogenesis

KW - Carthamus tinctorius

KW - NMR

KW - Phenylpyruvic acid

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DO - 10.1016/j.tetlet.2020.152237

M3 - Article

AN - SCOPUS:85089066463

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Carthamusuchuric acid, an enolic glucoside of phenylpyruvic acid from the florets of Carthamus tinctorius and anti-adipogenic phenolic compounds

Abstract

Keywords

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