Phenolic Lipids Research Articles

Distribution of tyrosol fatty acid esters in the gastrointestinal tracts of mice and their hydrolysis characteristics by gut microbiota.

Phenolic lipids have been approved as safe and effective antioxidants, and are a potential ingredient for functional foods. However, the characteristics of gastrointestinal distribution and microbial hydrolysis in the gastrointestinal tract (GI) are not clear. In this study, the above characteristics of tyrosol-myristic acid ester (T-C14:0), tyrosol-palmitic acid ester (T-C16:0) and tyrosol-stearic acid ester (T-C18:0) were estimated by an in vivo mice model and in vitro anaerobic fermentation model. HPLC-UV measurements indicate that tyrosol (TYr) was rapidly and almost completely absorbed in the small intestine. By contrast, oral T-C14:0, T-C16:0 and T-C18:0 were remarkably stable in the stomach environments of the mice, and could be further hydrolyzed to free TYr by gut microbiota including Lactobacillus johnsonii, Lactobacillus reuteri and Lactobacillus gasseri (in the colon and cecum). Further, the liberated TYr and fatty acids can participate in regulating the composition of the gut microorganisms, which may lead to some additional health benefits. Therefore, the production of phenolic lipids such as tyrosol fatty acid esters provides a new approach to prolong the action time of polyphenol in vivo, and could also lead to additional health benefits including the regulation of gut microorganisms.

Ordered structure of preformed V-amylose inclusion complex with 5-heptadecylresorcinol

5-Heptadecylresorcinol (ARs-17) is an amphiphilic phenolic lipid in grain bran with multiple bioactivities. In this study, the relationship between the crystalline structure, thermostability, morphological properties and in vitro digestibility of high amylose maize starch (HAMS) and preformed V-amylose (V6a, V6h, V7a, V7h, V8a, V8h) inclusion complexes with ARs-17 were investigated by X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC), and scanning electron microscope (SEM). XRD and FTIR results revealed that both HAMS and V-amylose could form V6-type crystalline inclusion complexes with ARs-17, and the hydrophobic alkyl chain of ARs-17 located in the amylose helix cavity, while the hydrophilic phenolic hydroxyl group of ARs-17 located outside the helix. DSC analysis demonstrated that the complexation of V-amylose and ARs-17 was beneficial to the formation of stable type VIIb complexes with higher peak temperature over 140 °C, while the endothermal peak of HAMS-ARs-17 inclusion complex was only around 115 °C. SEM images detected that V-amylose and their complexes were spherical shape with the close-packed structure and aggregated together. By parameterizing digestion kinetics through logarithm-of-slope analysis (LOS) plot fitting, V6a-ARs-17 and V6h-ARs-17 inclusion complexes exhibited the lowest digestibility. This study suggests the great potential to apply V-amylose as functional ingredient for improving both processing and digestion stability of alkylresorcinols and thereby enhancing its bioaccessibility.

Effect of boiling and oven roasting on some physicochemical properties of sunflower seeds produced in Far North, Cameroon.

The effects of different processing methods on proximate composition, total phenolic content, antioxidant activity, lipid oxidation, and mineral contents of sunflower seeds produced in Far North Region of Cameroon were evaluated. Mean moisture, ash, lipid, protein, fiber, and carbohydrate contents of raw sunflower seeds were 6.60%, 2.55%, 44.65%, 20.17%, 4.08%, and 21.25%, respectively. The changes in moisture, ash (excepted in boiled samples), lipid, protein, fiber, and carbohydrate (excepted in roasted samples) were found to be significant for all cooking methods. Ash and lipid contents of samples roasted at 120°C were found to be significant when compared with other cooking methods. Antioxidant activity increased with treatment. After processing, the acid, peroxide, and thiobarbituric acid values increased significantly, whereas iodine value decreased. The roasting process improved the induction time, and samples roasted at 120°C were found to have the highest induction time (2.29 ± 0.09 hr). Raw sunflower seeds were good sources of potassium (K), magnesium (Mg), calcium (Ca), iron (Fe), zinc (Zn), and manganese (Mn). Increase in contents of Ca, Mg, Zn, Cu, and Fe was observed during processing. Roasting compared with boiling appeared to be the best cooking method of sunflower seeds concerning nutrient content, antioxidant stability, and lipid stability.

New essential dietary lipids?

•Studies involving foods, like whole fat dairy, that contain odd-chain fatty acids show a correlation between good health and how much an individual consumes. There is a similar correspondence with whole grains intake, possibly an effect of odd-chain phenolic lipids in these foods.These bioactive compounds show antioxidant and anti-inflammatory capabilities in animal and in vitro studies, but clinical studies to determine efficacy and dosing have not yet been conducted. •Are odd-chain fatty acids the next omega-3s, and should consumers consider taking supplements?

Cashew Nut Shell Liquid (CNSL) as a Source of Drugs for Alzheimer's Disease.

Alzheimer’s disease (AD) is a complex neurodegenerative disorder with a multifaceted pathogenesis. This fact has long halted the development of effective anti-AD drugs. Recently, a therapeutic strategy based on the exploitation of Brazilian biodiversity was set with the aim of discovering new disease-modifying and safe drugs for AD. In this review, we will illustrate our efforts in developing new molecules derived from Brazilian cashew nut shell liquid (CNSL), a natural oil and a byproduct of cashew nut food processing, with a high content of phenolic lipids. The rational modification of their structures has emerged as a successful medicinal chemistry approach to the development of novel anti-AD lead candidates. The biological profile of the newly developed CNSL derivatives towards validated AD targets will be discussed together with the role of these molecular targets in the context of AD pathogenesis.

Effect of extraction solvents on total phenolic compound, lipid peroxidation, antioxidant and cytotoxic activity of leaves of Rubus armeniacus (Himalayan blackberry)

Effect of extraction solvents on total phenolic compound, lipid peroxidation, antioxidant and cytotoxic activity of leaves of Rubus armeniacus (Himalayan blackberry)

Pouteria lucuma Pulp and Skin: In Depth Chemical Profile and Evaluation of Antioxidant Activity.

Pouteria lucuma Ruiz and Pav., known as the ‘Gold of the Incas’ or ‘lucuma’, is a subtropical fruit belonging to the Sapotaceae family, with a very sweet flavor, used to prepare cakes, ice creams as well as in the baking and dairy industries. To date, the content of primary metabolites is known, but little information is reported about the composition in specialized metabolites. Moreover, no study is reported on skin which represent an important agricultural waste due to the high demand for lucuma. In order to have a preliminary metabolite profile of Pouteria lucuma, the extracts of pulp and skin have been analyzed by LC-ESI/LTQOrbitrap/MS/MS in negative ion mode. The careful analysis of the accurate masses, of the molecular formulas and of the ESI/MS spectra allowed to identify specialized metabolites belonging to phenolic, flavonoid and polar lipid classes. The LC-MS/MS analysis guided the isolation of compounds occurring in the pulp extract whose structures have been characterized by spectroscopic methods including 1D- and 2D-NMR experiments and ESI-MS analysis. Furthermore, the phenolic content of the extracts along with the antioxidant activity of extracts and isolated compounds was evaluated.

Antioxidant and Biological Activities of Novel Structured Monoacylglycerol Derivatives with Phenolic Acids

AbstractNovel structured monoacylglycerol (MAG)‐based phenolic lipids are synthesized from11‐bromoundecanoic acid, phenolic acids, and solketal. Selected phenolic acids namely 4‐hydroxy benzoic, vanillic, syringic, cinnamic, p‐coumaric, sinapic, 4‐fluorocinnamic, 4‐hydroxyphenyl acetic acid, 3‐(4‐hydroxyphenyl) propanoic and dihydrocaffeic acids are employed for the synthesis of ten novel MAG‐based phenolic lipids. The synthesized phenolic lipids are characterized by FT‐IR, NMR, and mass spectra analysis. All the compounds are evaluated for antioxidant, antimicrobial, and cytotoxic activities. MAG derivative 8g of sinapic acid exhibits excellent antioxidant activity in both DPPH assay and inhibition of lipid oxidation assay. MAG derivative 8f bearing p‐coumaric acid shows good antimicrobial activity against both Gram‐positive and Gram‐negative bacterial strains with a minimum inhibitory concentration (MIC) value of 6.25 µm mL−1. All the synthesized compounds are found to exhibit cytotoxicity against B16, DU145, and CHO cell lines, while sinapic and p‐coumaric acid derivatives exhibit better activities compared to other derivatives.

Lipase catalysed transesterification of palm stearin with ferulic acid in solvent-free media

Recently, several scientific groups investigated the suitable enzymatic route for synthesis of structured phenolic lipids for cosmetic and nutritive purposes. The feruloylated palm stearin (FPS) was obtained from enzymatic transesterification reactions of palm stearin with ferulic acid in solvent-free media with 1 mmol of glycerol or without it, using non-specific lipases, NovoCor ADL (Candida antarctica lipase A); Novozyme435® (Candida antarctica lipase B), and 1,3-specific lipase Lipozyme TL 100L from Thermomyces lanuginosus. The individual lipases and their combinational systems were examined. ESI+-MS/MS confirmed the formation of 19 feruloylated compounds. FPSs were produced by all lipases and their combinations. The positive synergetic effect occurred for 1,3-specific lipase and unspecified lipases with mass ratio 8:2, respectively. The antioxidant activities of all FPSs were examined. FPS produced by NovoCor ADL lipase in presence of free glycerol showed an antioxidant activity 10.3-times higher. In conclusion, the two low-cost lipases NovoCor ADL and Lipozyme TL 100L and its combi-lipase system could be considered suitable low-cost alternative to the expensive wide use N435 lipase in the solvent free production process of FPS for food and cosmetic applications.

Review Article Recent Advances in Preventing Dental Erosion

Dental erosion is defined as an irreversible loss of dental hard tissue due to exposure to chelating agents or non-bacterial acids. The occurrence of this condition was noted and the incidence and prevalence of dental erosion has been increasingly documented.The Ant erosive agents such as Anacardic acid in which the key component is the cashewnut shell liquid is phenolic lipids. It is a mixture of molecules which are saturated and unsaturated. It is also considered to have an anti-microbial effect and has been studied for the treatment of cancer, oxidative damage, inflammation and obesity disorders. Other anti-erosive agent like Fluoride helps in tooth remineralization. Fluorapatite, rather than hydroxyapatite, forms during the process of remineralization when fluoride is found in oral fluids. In apatite crystal lattice formation, fluoride ions replace hydroxy ions. Fluorapatite, even under acidic conditions, is less soluble than hydroxyapatite, which helps to regenerate tooth enamel. Fluoride is therefore a stronger anti-erosive agent. Various Recent advances in anti-erosive agents are Calcium and phosphate, Casein phosphopeptide amorphous calcium phosphate (CPP-ACP), Protease inhibitors, Oils, Chitosan chitosan and Multivalent metal ions Various techniques to evaluate dental erosion are in vitro techniques and in vivo techniques. In vitro techniques are Scanning electron microscope, Surface Profilometry, Polarized Light Microscopyand Non-Contact Confocal Laser Scanning Microscopy (CLSM). And iv vivo techniques are Photographs Clinical review and indices. The most important point of treatment is identifying and removing the erosion factor, above all current materials and methods. Therefore, early identification of the lesions, evaluation and removal of the etiological variables are relevant topics.

Dietary Bioactive Lipids: A Review on Absorption, Metabolism, and Health Properties.

Dietary lipids are an indispensable source of energy and nutrition in human life. Numerous studies have shown that dietary bioactive lipids have many health benefits, including prevention or treatment of chronic diseases. The different chemical compositions and structural characteristics of bioactive lipids not only affect their digestion, absorption, and metabolism but also affect their health properties. In this review, the major dietary bioactive lipids (fatty acids, carotenoids, phytosterols, phenolic lipids, fat-soluble vitamins, and sphingomyelins) in foods are systematically summarized, from the aspects of composition, digestion, absorption, metabolism, source, structural characteristics, and their health properties. In particular, the relationship between the compositional and structural changes of bioactive lipids and their absorption and metabolism is discussed as well as their effect on health properties. This review provides a comprehensive summary toward health properties of dietary bioactive lipids.

Odd chain fatty acids and odd chain phenolic lipids (alkylresorcinols) are essential for diet

AbstractOdd chain fatty acids (15:0 and 17:0) from dairy fat as well as odd chain phenolic lipids (alkylresorcinols) from whole grain are commonly reviewed as candidate biomarkers for dietary analysis and their ingestion are inversely related to chronic disease risks. Therefore, low levels of dietary intake of these odd chain molecules may be related to higher risk of physiological states that cause chronic diseases or mortality. It is a prerequisite to examine and understand their main role in beneficial health effects in disease prevention. We propose odd chain fatty acids (OC‐FA) and most importantly odd chain phenolic lipids (OC‐PL) as potential essential dietary compounds since they play key roles in physiological mechanisms. This review evaluates potential roles of OC‐FA and OC‐PL in mitigating chronic diseases in vitro and in vivo studies to support our hypothesis for odd chain molecules as essential dietary lipids. Further studies are needed to investigate the relationship between reduced intake of OC‐FA‐ and OC‐PL‐containing foods and susceptibilities to chronic diseases.

Molecular Networking Leveraging the Secondary Metabolomes Space of Halophila stipulaceae (Forsk.) Aschers. and Thalassia hemprichii (Ehrenb. ex Solms) Asch. in Tandem with Their Chemosystematics and Antidiabetic Potentials.

The Red Sea is one of the most biodiverse aquatic ecosystems. Notably, seagrasses possess a crucial ecological significance. Among them are the two taxa Halophila stipulacea (Forsk.) Aschers., and Thalassia hemprichii (Ehrenb. ex Solms) Asch., which were formally ranked together with the genus Enhalus in three separate families. Nevertheless, they have been recently classified as three subfamilies within Hydrocharitaceae. The interest of this study is to explore their metabolic profiles through ultra-high-performance liquid chromatography-high-resolution mass spectrometry (UPLC-HRMS/MS) analysis in synergism with molecular networking and to assess their chemosystematics relationship. A total of 144 metabolites were annotated, encompassing phenolic acids, flavonoids, terpenoids, and lipids. Furthermore, three new phenolic acids; methoxy benzoic acid-O-sulphate (16), O-caffeoyl-O-hydroxyl dimethoxy benzoyl tartaric acid (26), dimethoxy benzoic acid-O-sulphate (30), a new flavanone glycoside; hexahydroxy-monomethoxy flavanone-O-glucoside (28), and a new steviol glycoside; rebaudioside-O-acetate (96) were tentatively described. Additionally, the evaluation of the antidiabetic potential of both taxa displayed an inherited higher activity of H. stipulaceae in alleviating the oxidative stress and dyslipidemia associated with diabetes. Hence, the current research significantly suggested Halophila, Thalassia, and Enhalus categorization in three different taxonomic ranks based on their intergeneric and interspecific relationship among them and supported the consideration of seagrasses in natural antidiabetic studies.

Effect of Dietary Grape Pomace on Fattening Rabbit Performance, Fatty Acid Composition, and Shelf Life of Meat.

The use of agroindustry by-products in animal diets allows the use of residues that are not fit for human consumption. In this study, it was investigated whether fattening commercial rabbits during 30 days with a non-medicated feed, with 20% addition of grape pomace (GPD), affected production traits and the fatty acid composition, antioxidants properties, and the shelf life of the meat compared to a conventional strategy (CON). Furthermore, it was tested, by chromatographic analysis, whether this alternative diet allowed the transfer of phenolic compounds to the meat. Thirty-six weaned rabbits were allotted to the two treatments. In each treatment, 18 rabbits were fattened in three indoor cages, each housing three males and three female rabbits. No significant differences were found in live weights (p > 0.05), but the feed conversion rate and carcass weight and yield were found to be impaired in the GPD group (p ≤ 0.05). The GPD group had a higher intramuscular fat percentage (2.01 vs. 1.54), improved polyunsaturated/saturated fatty acids ratio (0.75 vs. 0.66), and better atherogenicity (0.71 vs. 0.83) and thrombogenicity (1.14 vs. 1.24) indexes, while the n-6/n-3 ratio was higher (25.4 vs. 20.3). Total volatile basic nitrogen in meat was lower in the GPD group (p = 0.01), suggesting a delayed spoilage. However, no improvements in total phenolic content, antioxidant capacity, reducing power, and lipid oxidation (p > 0.05) were found in the meat. Even though the GPD pellets offered to the animals had several grape-derived phenolic compounds, and higher antioxidant properties compared to the CON diet, none of the phenolic compounds detected in feeds were detected in the meat samples.

Seed anatomy and histochemistry of Myrciaria dubia (Kunth) McVaugh, an Amazonian Myrtaceace

Myrciaria dubia, or camu-camu, is a perennial species that produces fruits of great nutritional interest because they have high levels of antioxidant compounds. The species occurs spontaneously on Amazonian river margins and requires a low amount of nutritional resources. Further, Myrciaria dubia fruits are collected via extractivism and managing this process is still at an incipient stage. The present study investigated the anatomical and histochemical aspects of the seeds of five clones of Myrciaria dubia. The external seed coat has an epidermis comprising a single layer of tabular cells that are rich in phenolic content, pectins, alkaloids, and terpenes. The cotyledons have a uniseriate epidermis, polyhedral parenchyma cells with a high concentration of starch grains, dispersed vascular bundles, alkaloids, and idioblasts with phenolic content, lipids, and proteins. The embryonic axis has a protoderm with cuboid, juxtaposed cells with thin walls and a conspicuous nucleus. Secondary metabolites in the seeds are mainly in the seed coat. This work provides new information about the anatomical and histochemical aspects of Myrciaria dubia seeds. No differences in the structural characteristics of the seeds and ovules were recorded among the clones since these are the most conserved reproductive organs in seed plants.

Arı Poleni: Antioksidan Etkisi

Bee pollen is a honey bee product containing over 250 biologically active substances such as phenolic bases, amino acids, carbohydrates, lipids, enzymes and coenzymes, vitamins and bio-elements. The composition of bee pollen may vary due to plant sources and its botanical and geographical origin. Bee pollen has been used since ancient times in traditional medicine for its therapeutic effects such as wound healing and hepatoprotective. Bee pollen has been reported to possess antioxidant and radical scavenging activities usually attributed to the presence of phenolic acids and flavonoids which are plant-derived polyphenolic substances. The antioxidant capacity of bee pollen depends on the content of total polyphenolic substances. This review presents an overview of chemical composition and antioxidant activity of bee pollen.

Isolation of saturated alkylresorcinols from rye grains by countercurrent chromatography.

Alkylresorcinols (5-alkyl-1,3-dihydroxybenzenes) are amphiphilic phenolic lipid compounds that are abundant in cereals with highest contents in rye. Alkylresorcinols are suspected to show a wide range of favourable biological activities. For such and further testing, highly pure alkylresorcinol standards are required. Especially, purities>>98% were partly difficult to obtain in the past. Here, we aimed to isolate the most abundant (saturated) alkylresorcinols from rye using countercurrent chromatography. To achieve very high purity, alkylresorcinol-containing extract (∼7.14g) of rye grains (cold extracts with cyclohexane/ethyl acetate (46/54, w/w)) were preparatively transesterified followed by a preparative hydrogenation. Countercurrent chromatography separation of ∼1g hydrogenated and transesterified rye grain extract using the solvent system n-hexane-ethyl acetate-methanol-water (9:1:9:1, v/v/v/v) yielded 51.8mg AR17:0, 77.4mg AR19:0, 57.2mg AR21:0, 28.8mg AR23:0 and 11.5mg AR25:0 with purities>99% in either case. The isolated alkylresorcinol homologues can be used for subsequent bioassays.

Three Novel Dietary Phenolic Compounds from Pickled Raphanus Sativus L. Inhibit Lipid Accumulation in Obese Mice by Modulating the Gut Microbiota Composition.

Although pickled radish is widely consumed worldwide, few studies have investigated the nutritional benefits of bioactive compounds extracted from pickled radish. In this study, the authors investigate the relationship among dietary phenolic compounds, lipid accumulation, and gut microbiota. Three phenolic compounds 2,6-dihydroxyacetophenone (DHAP), 4-hydroxyphenethyl alcohol (4-HPEA), and 4-hydroxybenzaldehyde (HBA) are extracted from pickled radish. LO2 cells treated with free fatty acid are first used to explore the impact of the above three compounds at different doses on reducing lipid levels. The effects of the three compounds on obesity and the gut microbiota are further investigated in high-fat diet (HFD)-induced KM mice. Results show that three compounds inhibited the lipid accumulation in LO2 cells. The results of animal experiments reveal that three compounds prevented body weight gain and significantly decreased serum lipid levels. Treatment with DHAP, HPEA, and HBA reversed gut microbiome dysbiosis in HFD-induced mice. The three phenolic compounds increase Odoribacter, and decrease Helicobacter and Mucispirillum. Notably, DHAP and HBA reduce the HFD-induced increase in the Firmicutes/Bacteroidetes ratio. These data suggest that phenolic compounds extracted from pickled radish possess excellent lipid-lowering capacity, providing a theoretical basis for further analysis of the nutritional value of pickled radish.

Synthesis of cardanol-based 1,2,3-triazoles as potential green agents against neoplastic cells

The cashew plant (Anacardium occidentale L.) is the source of a wide variety of bioactive compounds consisting of phenolic lipids, mainly present in the spongy shells of cashew nuts. The liquid in the cashew nut shell generated after nut roasting in the food industry, which is usually treated as waste. However, it contains high amount of cardanol that could be used as a building block and are of innumerable applications. Herein, we report the synthesis of eleven 1,4-disubstituted 1,2,3-triazoles, derived from the cardanol, in an environmentally non-egregious fashion, and a cytotoxic evaluation study using the MCF-7 (breast carcinoma), 786-0 (kidney carcinoma) and HT-29 (colon carcinoma) cancer cell lines and cytotoxic evaluations against Trypanosoma cruzi. Five of the eleven triazoles presented high toxicity against the 786-0 kidney cancer cell line. However, no relevant toxicity to the T. cruzi amastigote was observed when compared with benznidazole (standard drug). A cell viability study demonstrated that these compounds act over a broad range of concentrations, which implies that they may be applied even in low doses. These results indicate an alternative use of cardanol in greener synthesis of potent anticancer drug candidates.

Encapsulation of saffron and sea buckthorn bioactives: Its utilization for development of low glycemic baked product for growing diabetic population of the world

In this study, bioactive compounds from saffron (Crocus sativus L.) and sea buckthorn (Hippophae rhamnoides L.) were extracted using ultrasound-assisted extraction method. The extracted bioactive compounds were encapsulated in sodium alginate. The encapsulation efficiency of SE (encapsulated saffron) and SBE(encapsulated sea buckthorn) was found to be 60.303%, and 64.662%, respectively. Further, the encapsulated powder were added in the wheat flour (1%) to prepare functional cookies and its effect on structural, thermal and antioxidant properties were studied. FTIR revealed a difference in the intensity of peaks between free and encapsulated saffron (SF and SE) and sea buckthorn (SBF and SBE) bioactives. DPPH scavenging activity, reducing power, total phenolic content and lipid peroxidation inhibition were performed which displayed that antioxidant activity was significantly higher. The in-vitro digestibility assay of cookies enriched with saffron and sea buckthorn showed slow digestion of cookies that means it hinders starch digestion and this approach is expected to design low glycemic bakery product for growing diabetic population of the world. Also, the cookies developed from encapsulated powder showed better consumer acceptability as compared to cookies with free bioactives.