Abstract
To expand the applications and enhance the stability and bioactivity of resveratrol (RE), and to simultaneously include the potential health benefits of short chain fatty acids (SCFA) esters of RE were prepared by Steglich reactions with acetic, propionic, and butyric acids, respectively. RE and the esterified RE-SCFA products (including RAE, RPE, and RBE) were analyzed using nuclear magnetic resonance (NMR), Fourier-transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), differential thermal analysis (DTA), and liquid chromatography–mass spectrometry (LC–MS). The FTIR and 13C NMR spectra of the esterified products included ester-characteristic peaks at 1751 cm−1 and 171 ppm, respectively. Moreover, the peaks in the range of 1700 to 1600 cm−1 in the FTIR spectra of the esterified products indicated that the esterification of RE-SCFA was successful. The TGA results revealed that the RE-SCFA esters decomposed at lower temperatures than RE. The peaks in the LC–MS profiles of the esterified products indicated the formation of mono- and diesters, and the calculated monoester synthesis rates ranged between 45.81 and 49.64%. The RE esters inhibited the Cu2+-induced low-density lipoprotein oxidation reaction, exhibited antioxidant activity in bulk oil, and effectively inhibited the hydroxyl radical-induced DNA scission. Moreover, the RE-SCFA esters had better hydrogen peroxide scavenging activity than RE. Our results are the first in the literature to successfully including short chain fatty acids in the esters of resveratrol, and the products could be used as a functional food ingredient in processed foods or can be used as dietary supplements to promote health.
Highlights
ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC), DMAP, and the urea byproduct dissolved in water, the catalyst was disengaged during this step, and pale yellow RE-short chain fatty acids (SCFA) esters were obtained after freeze-drying
The main upward peak in the range of 170–200 ◦ C in the differential thermal analysis (DTA) curves of the RE esters was attributed to the thermal decomposition of the esters. These results suggested that the RE-SCFA esters were thermally less stable than RE, a similar result reported in the previous study which indicated the resveratrol butyric ester (RBE) after esterification more thermo sensitivity [9]
The results indicated that the antioxidant capacity of RE was significantly higher than those of resveratrol acetic acid ester (RAE), resveratrol-propionic acid ester (RPE), and RBE, which was ascribed to the substitution of the hydroxyl groups of RE with ester groups after esterification (Table 3)
Summary
Licensee MDPI, Basel, Switzerland.Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/).The synthesis of resveratrol derivatives and their novel functional properties have been a research hotspot recently. Resveratrol (RE; 3,40 ,5 trihydroxystilbene) is a C6-C2-C6 stilbene natural phenolic compound with three hydroxyl groups [1] that is found in more than 70 plants and plays an important role in the defense against pathogens, infections, injury, and abiotic stress [1,2]. Resveratrol presents numerous therapeutic benefits, including anti-inflammatory, antioxidant, anti-platelet, anti-hyperlipidemia, immune-modulator, anti-carcinogenic, cardioprotective, vasorelaxant, and neuroprotective properties. In vitro, Antioxidants 2021, 10, 420. https://doi.org/10.3390/antiox10030420 https://www.mdpi.com/journal/antioxidants
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