Abstract
To facilitate broad applications and enhance bioactivity, resveratrol was esterified to resveratrol butyrate esters (RBE). Esterification with butyric acid was conducted by the Steglich esterification method at room temperature with N-ethyl-N′-(3-dimethylaminopropyl) carbodiimide (EDC) and 4-dimethyl aminopyridine (DMAP). Our experiments demonstrated the synthesis of RBE through EDC- and DMAP-facilitated esterification was successful and that the FTIR spectra of RBE revealed absorption (1751 cm−1) in the ester region. 13C-NMR spectrum of RBE showed a peak at 171 ppm corresponding to the ester group and peaks between 1700 and 1600 cm−1 in the FTIR spectra. RBE treatment (25 or 50 μM) decreased oleic acid-induced lipid accumulation in HepG2 cells. This effect was stronger than that of resveratrol and mediated through the downregulation of p-ACC and SREBP-2 expression. This is the first study demonstrating RBE could be synthesized by the Steglich method and that resulting RBE could inhibit lipid accumulation in HepG2 cells. These results suggest that RBE could potentially serve as functional food ingredients and supplements for health promotion.
Highlights
Resveratrol (RE) is a phenolic stilbenoid compound with aC6–C2–C6 structure with three hydroxyl groups
Our study demonstrates that resveratrol butyrate esters can be produced from resveratrol and butyric acid using ethyl-N -(3-dimethylaminopropyl) carbodiimide (EDC) and DMAP
Fourier-transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and LC/mass spectrometry (MS)/MS analyses confirmed the structure of resveratrol butyrate esters (RBE), which was found to be more thermosensitive than RE
Summary
It has been found in over 70 types of plants, including grape skin, grape seeds, giant knotweed, peanut, cassia seed, passion fruit, white tea, plums, and peanuts. It has powerful antioxidant activity and plays a role in the defense against pathogen infection, injury, and abiotic stress [1,2,3,4,5,6,7]. Molecules 2020, 25, 4199 and functional foods, and the excellent health benefits of RE have been confirmed by several studies It has preventive effects on oxidative stress, inflammation, and cardiovascular disease, and shows anti-carcinogenic activity [3,8,9,10]. RE has been proven to reduce the risk of developing diseases by inhibiting advanced glycation end product formation [11]
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