Metabolite Profile of Cucurbitane-Type Triterpenoids of Bitter Melon (Fruit of Momordica charantia) and Their Inhibitory Activity against Protein Tyrosine Phosphatases Relevant to Insulin Resistance

Qualitative analysis of cucurbitane-type triterpenoids of bitter melon (fruit of Momordica charantia L.) using ultraperformance liquid chromatography quadrupole time-of-flight mass spectrometry revealed 27 promising cucurbitane-type triterpenoids, and LC/MS-guided chemical analysis of M. charantia f...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2021-02, Vol.69 (6), p.1816-1830
Main Authors: Lee, Yong Hoon, Yoon, Sun-Young, Baek, Jiyun, Kim, Sung Jin, Yu, Jae Sik, Kang, Heesun, Kang, Ki Sung, Chung, Sang J, Kim, Ki Hyun
Format: Article
Language:English
Subjects:
Bioactive Constituents, Metabolites, and Functions
Fruit - chemistry
Gas Chromatography-Mass Spectrometry
Glycosides
Insulin Resistance
Momordica charantia
Protein Tyrosine Phosphatases
Triterpenes - analysis
Triterpenes - pharmacology
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Summary:Qualitative analysis of cucurbitane-type triterpenoids of bitter melon (fruit of Momordica charantia L.) using ultraperformance liquid chromatography quadrupole time-of-flight mass spectrometry revealed 27 promising cucurbitane-type triterpenoids, and LC/MS-guided chemical analysis of M. charantia fruit extract led to the isolation and structural characterization of 22 cucurbitane-type triterpenoids (1–22), including 8 new cucurbitane-type triterpenoidal saponins, yeojoosides A–H (1–8). The structures of the new compounds (1–8) were elucidated by spectroscopic methods, including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry. Their absolute configurations were assigned by quantum chemical electronic circular dichroism calculations, chemical reactions, and DP4+ analysis using gauge-including atomic orbital NMR chemical shift calculations. All isolated compounds (1–22) were examined for inhibitory activity against protein tyrosine phosphatases relevant to insulin resistance. Nine compounds (7, 8, 9, 11, 14, 15, 19, 20, and 21) showed selective inhibitory effects of over 70% against PTPN2. The present results suggested that these compounds would be potential antidiabetic agents.
ISSN:0021-8561
1520-5118
DOI:10.1021/acs.jafc.0c06085