Biological Properties, Health Benefits and Enzymatic Modifications of Dietary Methoxylated Derivatives of Cinnamic Acid

Rychlicka, Magdalena; Rot, Agata; Gliszczyńska, Anna

doi:10.3390/foods10061417

Cited by 24 publications

(20 citation statements)

References 88 publications

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“…Table 3 shows the comparison of identified compounds with previous studies [ 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 ,…”

Section: Resultsmentioning

confidence: 99%

Naturally Occurring Functional Ingredient from Filamentous Thermophilic Cyanobacterium Leptolyngbya sp. KC45: Phytochemical Characterizations and Their Multiple Bioactivities

et al. 2022

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Cyanobacteria are rich in phytochemicals, which have beneficial impacts on the prevention of many diseases. This study aimed to comprehensively characterize phytochemicals and evaluate multifunctional bioactivities in the ethanolic extract of the cyanobacterium Leptolyngbya sp. KC45. Results found that the extract mainly contained chlorophylls, carotenoids, phenolics, and flavonoids. Through LC–ESI–QTOF–MS/MS analysis, 38 phenolic compounds with promising bioactivities were discovered, and a higher diversity of flavonoids was found among the phenolic compounds identified. The extract effectively absorbed the harmful UV rays and showed high antioxidant activity on DPPH, ABTS, and PFRAP. The extract yielded high-efficiency inhibitory effects on enzymes (tyrosinase, collagenase, ACE, and α-glucosidase) related to diseases. Interestingly, the extract showed a strong cytotoxic effect on cancer cells (skin A375, lung A549, and colon Caco-2), but had a much smaller effect on normal cells, indicating a satisfactory level of safety for the extract. More importantly, the combination of the DNA ladder assay and the TUNEL assay proved the appearance of DNA fragmentation in cancer cells after a 48 h treatment with the extract, confirming the apoptosis mechanisms. Our findings suggest that cyanobacterium extract could be potentially used as a functional ingredient for various industrial applications in foods, cosmetics, pharmaceuticals, and nutraceuticals.

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Section: Resultsmentioning

confidence: 99%

Naturally Occurring Functional Ingredient from Filamentous Thermophilic Cyanobacterium Leptolyngbya sp. KC45: Phytochemical Characterizations and Their Multiple Bioactivities

et al. 2022

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“…Esterification of cinnamic acid can increase the stability, solubility/lipophilicity, and antioxidant effect of oil-based formulations, and it is also more suitable for human absorption in terms of physiological activity. Several studies have been attempted regarding the lipase-catalyzed modification of cinnamic acid derivatives with fatty acids or triacylglycerols, but it takes a long time to obtain synthetic products [ 32 ]. The hydrophilic character of phenolic acids has been reported to reduce their antioxidant effect in inhibiting the autoxidation of fats and oils.…”

Section: Resultsmentioning

confidence: 99%

Ultrasound Plus Vacuum-System-Assisted Biocatalytic Synthesis of Octyl Cinnamate and Response Surface Methodology Optimization

Tsai

Huang

et al. 2022

Molecules

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Cinnamic acid is one of the phenolic compounds that is isolated from cinnamon, or other natural plants, and has a wide range of physiological activities. However, the application of cinnamic acid is limited due to its poor solubility and low oral bioavailability. In this study, the feasibility of producing octyl cinnamate by ultrasonic assistance, combined with a rotary evaporation under vacuum, was studied using methyl cinnamate and octanol as the starting materials. A Box–Behnken design (BBD) was employed to evaluate the effects of the operation parameters, including reaction temperature (55–75 °C), reaction time (4–12 h), and ultrasonic power (90–150 W) on the production of octyl cinnamate. Meanwhile, the synthesis process was further optimized by the modeling response surface methodology (RSM). The data indicated that octyl cinnamate was efficiently synthesized from methyl cinnamate and octanol using the ultrasound plus vacuum system; further, this system was superior to the conventional method. According to the RSM model for the actual experiments, a reaction temperature of 74.6 °C, a reaction time of 11.1 h, and an ultrasound power of 150 W were determined to be the best conditions for the maximum molar conversion of octyl cinnamate (93.8%). In conclusion, the highly efficient synthesis of octyl cinnamate by a rotary evaporator with an ultrasound plus vacuum system was achieved via RSM optimization.

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“…Cinnamic acid is a phenolic compound which is known to be an antioxidant [ 43 ] and anticancer [ 44 ]. While its methoxylated derivatives are potentially hepatoprotective, antidiabetic, neuroprotective, and chemopreventive [ 45 ]. In this study, the contents p -coumaric acid ( 4 ) and 4-methoxycinnamic acid ( 5 ) isolated from the extract were not significantly high, whereas BBES had the highest content of both compounds which were 0.00059 mg/g ± 0.03 and 0.00278 mg/g ± 0.02, respectively; thus, the high TPC value and the antioxidant activity of the extracts were also contributed by other phenolic and secondary metabolites present in the extract.…”

Section: Discussionmentioning

confidence: 99%

Effects of Extraction Methods on Phenolic Content in the Young Bamboo Culm Extracts of Bambusa beecheyana Munro

et al. 2022

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Nowadays, many studies focus on the potential of bamboo as a source of bioactive compounds and natural antioxidants for nutraceutical, pharmaceutical, and food sources. This study is a pioneering effort to determine the total phenolic content, total flavonoid content and free radical scavenging activity, as well as the phenolic identification and quantification of Bambusa beecheyana. The study was conducted by using ethanol, methanol, and water for solvent extraction by applying cold maceration, Soxhlet, and ultrasonic-assisted extraction techniques. The results showed that Soxhlet and ultrasonic-assisted Bambusa beecheyana culm extracts had an increase in the extract’s dry yield (1.13–8.81%) but a constant p-coumaric acid (4) content (0.00035 mg/g) as compared to the extracts from the cold maceration. The ultrasonic-assisted extraction method required only a small amount (250 mL) of solvent to extract the bamboo culms. A significant amount of total phenolics (107.65 ± 0.01 mg GAE/g) and flavonoids (43.89 ± 0.05 mg QE/g) were found in the Soxhlet methanol culm extract. The extract also possessed the most potent antioxidant activity with an IC50 value of 40.43 µg/mL as compared to the positive control, ascorbic acid. The UHPLC–ESI–MS/MS analysis was carried out on the Soxhlet methanol extract, ultrasonic-assisted extract at 40 min, and cold methanol extract. The analysis resulted in the putative identification of a total of five phenolics containing cinnamic acid derivatives. The two cinnamic acid derivatives, p-coumaric acid (4) and 4-methoxycinnamic acid (5), were then used as markers to quantify the concentration of both compounds in all the extracts. Both compounds were not found in the water extracts. These results revealed that the extract from Soxhlet methanol of Bambusa beecheyana could be a potential botanical source of natural antioxidants. This study provides an important chemical composition database for further preclinical research on Bambusa beecheyana.

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Biological Properties, Health Benefits and Enzymatic Modifications of Dietary Methoxylated Derivatives of Cinnamic Acid

Cited by 24 publications

References 88 publications

Naturally Occurring Functional Ingredient from Filamentous Thermophilic Cyanobacterium Leptolyngbya sp. KC45: Phytochemical Characterizations and Their Multiple Bioactivities

Naturally Occurring Functional Ingredient from Filamentous Thermophilic Cyanobacterium Leptolyngbya sp. KC45: Phytochemical Characterizations and Their Multiple Bioactivities

Ultrasound Plus Vacuum-System-Assisted Biocatalytic Synthesis of Octyl Cinnamate and Response Surface Methodology Optimization

Effects of Extraction Methods on Phenolic Content in the Young Bamboo Culm Extracts of Bambusa beecheyana Munro

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