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Most absorption enhancers boost the oral absorption of drugs via increasing intestinal permeability. However, they often damage intestinal mucosa and induce inflammatory reactions. The aim of this study is to synthesize a new absorption enhancer, punicic acid ethyl ester (PAEE), with excellent absorption-prompting effect and low toxicity. The structure of PAEE was confirmed by NMR, MS, IR and UV. Setting oleic acid (OA) as the control, the three forms of punicic acid (PA), ie, free PA, PAEE, and pomegranate seed oil, in which PA exists in the form of triglyceride, were formulated into nanoemulsions (NE). The stability, physiochemical properties of the oils and NE were compared. The permeation-enhancing effect was estimated by phenol red intestinal transport experiments. The potential damage on small intestines was assessed by biochemical assay and pathological section. Though the three forms of PA had various strength in enhancing intestinal permeability, the difference was not significant (p > 0.05). Moreover, the effect was notably stronger than that of OA (p < 0.05) and was inversely related to the density and required HLB value of the oils. Compared to the corresponding oils, the NE exhibited much weaker effect in prompting intestinal permeability. Oral administration of OA and OA NE for 10 d impaired intestinal mucosa and villi along with strong inflammatory reactions in the small intestines. In contrast, the oils from PA series and their NE did not induce obvious intestinal inflammation. PAEE and its NE hindered the release of cytokines and increased the ratio of intestinal villus length to crypt depth. PAEE is a promising absorption enhancer with a strong permeability-prompting effect and mucosa-protecting capacity against intestinal inflammation. It provides a practical strategy to enhance the bioavailability of the drugs with poor biological membrane penetration.

Enzymatic pretreatment of seeds is a novel approach that enhances the health benefits of the extracted oil. The study investigated the influence of the enzymatic pretreatment of seeds on the quality of oil from different pomegranate cultivars. The quality of the ultrasound-assisted (and ethanol-extracted) oil was studied, with respect to the refractive index (RI), yellowness index (YI), conjugated dienes (K232), peroxide value (PV) ρ-anisidine value (AV), total oxidation value (TOTOX), total carotenoid content (TCC), total phenolic compounds (TPC), fatty acid composition, phytosterol composition, ferric reducing antioxidant power (FRAP), and 2.2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging capacity. The seeds of three different pomegranate cultivars (‘Wonderful’, ‘Herskawitz’, and ‘Acco’) were digested with an equal mixture of Pectinex Ultra SPL, Flavourzyme 100 L, and cellulase crude enzymes, at a concentration, pH, temperature, and time of 1.7%, 4.5, 40 °C, and 5 h, respectively. Enzymatic pretreatment of PS increased oil yield, PV, TPC, TCC, and DPPH radical scavenging capacity, but decreased the YI. The levels of K232, AV and TOTOX, fatty acids, phytosterols, RI, and FRAP, were not significantly affected by enzymatic pretreatment of PS. Principal component analysis (PCA) established that oil extracted from the ‘Acco’ seed after enzymatic pretreatment had higher yield, TPC, TCC, and DPPH radical scavenging capacity. Therefore, enzyme-pretreated ‘Acco’ pomegranate fruit seed is a source of quality seed oil with excellent antioxidant properties.

Over the last decades, we have witnessed an increasing interest in food-related products containing vegetable oils. These oils can be obtained either by extraction or by mechanical pressing of different parts of plants (e.g., seeds, fruit, and drupels). Producers of nutraceuticals have ceaselessly searched for unique and effective natural ingredients. The enormous success of argan oil has been followed by discoveries of other interesting vegetable oils (e.g., pomegranate oil) containing several bioactives. This work describes the pomegranate fruit extract and seed oil as a rich source of conjugated linolenic acid as a metabolite of punicic acid (PA), deriving from the omega-5 family (ω-5). Through the chemical characterization of PA, its nutritional and therapeutic properties are highlighted together with the physiological properties that encourage its use in human nutrition. We analyzed the composition of all fatty acids with beneficial properties occurring in pomegranate seed oil using gas chromatography (GC) with flame-ionization detection (FID) analysis combined with Fourier transform infrared spectroscopy (FTIR). Pomegranate seed oil mainly consists of 9,11,13-octadic-trienoic acid (18:3), corresponding to 73 wt % of the total fatty acids. Nine components were identified by GC in PSO, varying between 0.58 and 73.19 wt %. Using midinfrared (MIR) spectroscopy, we compared the composition of pomegranate seed oil with that of meadowfoam seed oil (MSO), which is also becoming increasingly popular in the food industry due to its high content of long chain fatty acids (C20-22), providing increased oil stability. From the results of FTIR and MIR spectroscopy, we found that punicic acid is unique in PSO (73.19 wt %) but not in MSO.

Plant-derived conjugated linolenic acids (CLnA) have been widely studied for their preventive and therapeutic properties against diverse diseases such as cancer. In particular, punicic acid (PunA), a conjugated linolenic acid isomer (C18:3 c9t11c13) present at up to 83% in pomegranate seed oil, has been shown to exert anti-cancer effects, although the mechanism behind its cytotoxicity remains unclear. Ferroptosis, a cell death triggered by an overwhelming accumulation of lipid peroxides, has recently arisen as a potential mechanism underlying CLnA cytotoxicity. In the present study, we show that PunA is highly cytotoxic to HCT-116 colorectal and FaDu hypopharyngeal carcinoma cells grown either in monolayers or as three-dimensional spheroids. Moreover, our data indicate that PunA triggers ferroptosis in carcinoma cells. It induces significant lipid peroxidation and its effects are prevented by the addition of ferroptosis inhibitors. A combination with docosahexaenoic acid (DHA), a known polyunsaturated fatty acid with anticancer properties, synergistically increases PunA cytotoxicity. Our findings highlight the potential of using PunA as a ferroptosis-sensitizing phytochemical for the prevention and treatment of cancer.

Immunomodulators are agents able to affect the immune system, by boosting the immune defences to improve the body reaction against infectious or exogenous injuries, or suppressing the abnormal immune response occurring in immune disorders. Moreover, immunoadjuvants can support immune system acting on nonimmune targets, thus improving the immune response. The modulation of inflammatory pathways and microbiome can also contribute to control the immune function. Some plant-based nutraceuticals have been studied as possible immunomodulating agents due to their multiple and pleiotropic effects. Being usually more tolerable than pharmacological treatments, their adjuvant contribution is approached as a desirable nutraceutical strategy. In the present review, the up to date knowledge about the immunomodulating properties of polysaccharides, fatty acids and labdane diterpenes have been analyzed, in order to give scientific basic and clinical evidence to support their practical use. Since promising evidence in preclinical studies, limited and sometimes confusing results have been highlighted in clinical trials, likely due to low methodological quality and lacking standardization. More investigations of high quality and specificity are required to describe in depth the usefulness of these plant-derived nutraceuticals in the immune system modulation, for health promoting and disease preventing purposes.

Pomegranate seed oil (PSO) is recognized as a major by-product of the agro-food industry. This study evaluates thirty Iranian pomegranate cultivars with respect to their seed oil yield and fatty acid composition. Cultivars with the highest oil yields were selected for further analysis of oil stability and quality. Oxidative stability was assessed through standardized oxidation tests, and chemical changes were monitored using 1 H NMR spectroscopy under various storage conditions. The findings revealed that punicic acid was the dominant fatty acid, while stearic acid was the least prevalent. 1 H NMR analysis confirmed the isomerization of punicic acid (C18:3 9c, 11t, 13c) to β-eleostearic acid (C18:3 9t, 11t, 13t), caused by the conversion of cis bonds to trans under direct sunlight exposure. A notable degradation in oil quality was observed under oxidative conditions. Based on these results, storage at room temperature, protected from sunlight and air (to limit oxygen exposure), is recommended to maintain PSO quality. This study offers valuable insights into the potential of PSO as a functional food by-product and highlights essential technical considerations for its storage in the food industry.

Pomegranate (Punica granatum L.), commonly known as a seeded or granular apple, is a delectable fruit eaten worldwide. Pomegranate is one of the healthiest fruits, with a high concentration of phenolic compounds. Large quantities of byproducts, such as seeds and peels, are produced during the pomegranate juice extraction process, which causes disposal problems and environmental contamination. Pomegranate peel (PoP), which accounts for around 30%–40% of the fruit component, is a byproduct of the fruit juice manufacturing industry. PoP is a rich source of polyphenols including phenolic acids, tannins, and flavonoids, especially anthocyanin. These peels offer several functional and nutraceutical qualities owing to their bioactive ingredients, including lowering blood pressure, reducing oxidative stress, lowering cholesterol levels, and restoring heart health. PoPs have a variety of biological effects, including the ability to resist pathogenic microbes effectively, and used as an additive in various food applications. The current review focuses on the PoP's nutritional and practical attributes, as well as their functions as food additives and functional food preparations. The current review focuses on the pomegranate peel's nutritional and practical attributes, as well as their functions as food additives and functional food preparations.

Punicic acid (PuA) is a polyunsaturated fatty acid with significant medical, biological, and nutraceutical properties. The primary source of punicic acid is the pomegranate seed oil obtained from fruits of trees that are mainly cultivated in subtropical and tropical climates. To establish sustainable production of PuA, various recombinant microorganisms and plants have been explored as platforms with limited efficiencies. In this study, the oleaginous yeast Yarrowia lipolytica was employed as a host for PuA production. First, growth and lipid accumulation of Y. lipolytica were evaluated in medium supplemented with pomegranate seed oil, resulting in the accumulation of lipids up to 31.2%, consisting of 22% PuA esterified in the fraction of glycerolipids. In addition, lipid-engineered Y. lipolytica strains, transformed with the bifunctional fatty acid conjugase/desaturase from Punica granatum (PgFADX), showed the ability to accumulate PuA de novo. PuA was detected in both polar and neutral lipid fractions, especially in phosphatidylcholine and triacylglycerols. Promoter optimization for PgFADX expression resulted in improved accumulation of PuA from 0.9 to 1.8 mg/g of dry cell weight. The best-producing strain expressing PgFADX under the control of a strong erythritol-inducible promoter produced 36.6 mg/L PuA. These results demonstrate that the yeast Y. lipolytica is a promising host for PuA production.

Glioblastoma is one of the most lethal tumors, displaying striking cellular heterogeneity and drug resistance. The prognosis of patients suffering from glioblastoma after 5 years is only 5%. In the present work, capsaicin analogues bearing modifications on the acyl chain with long-chain fatty acids showed promising anti-tumoral activity by its cytotoxicity on U-87 and U-138 glioblastoma multiforme cells. The capsaicin analogues were enzymatically synthetized with cross-linked enzyme aggregates of lipase B from Candida antarctica (CALB). The catalytic performance of recombinant CALB-CLEAs was compared to their immobilized form on a hydrophobic support. After 72 h of reaction, the synthesis of capsaicin analogues from linoleic acid, docosahexaenoic acid, and punicic acid achieved a maximum conversion of 69.7, 8.3 and 30.3% with CALB-CLEAs, respectively. Similar values were obtained with commercial CALB, with conversion yields of 58.3, 24.2 and 22% for capsaicin analogues from linoleic acid, DHA and punicic acid, respectively. Olvanil and dohevanil had a significant cytotoxic effect on both U-87 and U-138 glioblastoma cells. Irrespective of the immobilization form, CALB is an efficient biocatalyst for the synthesis of anti-tumoral capsaicin derivatives. Key points • This is the first report concerning the enzymatic synthesis of capsaicin analogues from docosahexaenoic acid and punicic acid with CALB-CLEAs. • The viability U-87 and U-138 glioblastoma cells was significantly affected after incubation with olvanil and dohevanil. • Capsaicin analogues from fatty acids obtained by CALB-CLEAs are promising candidates for therapeutic use as cytotoxic agents in glioblastoma cancer cells.

Punicic acid is an uncommon ω-5 conjugated fatty acid with significant biological activity, mainly found in pomegranate seed oil. Due to limited natural availability, heterologous production of punicic acid in oleaginous yeasts offers a sustainable alternative. In this study, Yarrowia lipolytica was engineered for punicic acid biosynthesis by expressing the PgFADX gene from Punica granatum and subsequently modified to evaluate the influence of distinct diacylglycerol acyltransferases on punicic acid accumulation. The effects of seven acyltransferases, originating from P. granatum or Y. lipolytica, were compared under various cultivation conditions. The PgDGAT1 enzyme demonstrated the most favorable balance between total lipid content and punicic acid accumulation. Medium containing crude glycerol as a low-cost carbon source was initially tested in flask experiments with punicic acid accumulation in yeast cells of 129 mg/L. Further optimization of crude glycerol medium and subsequent scale-up experiments confirmed the potential of crude glycerol as an effective substrate, yielding up to 147.8 mg/L of punicic acid. Overall, this work identifies key enzymatic determinants for efficient punicic acid biosynthesis and supports Y. lipolytica as a robust host for the sustainable production of conjugated fatty acids from waste substrates.