Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 69, Issue 6, Pages 1816-1830Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c06085
Keywords
Momordica charantia; cucurbitane-type triterpenoids; NMR chemical shift calculation; protein tyrosine phosphatase
Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIT) [2018R1A2B2006879, 2019R1A5A2027340]
- Bio & Medical Technology Development Program of the National Research Foundation of Korea (NRF) - Korean government (MSIT) [NRF-2012M3A9C4048775]
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Qualitative analysis using ultraperformance liquid chromatography quadrupole time-of-flight mass spectrometry revealed 27 promising cucurbitane-type triterpenoids in bitter melon. Further chemical analysis led to the isolation and structural characterization of 22 cucurbitane-type triterpenoids, including 8 new triterpenoidal saponins. The compounds showed potential as antidiabetic agents, with 9 of them exhibiting significant inhibitory effects against PTPN2.
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.
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