The phenolic profile of skin and flesh from Manifera indica main commercial cultivars (Keitt and Tommy Atkins) in Costa Rica was studied using ultra performance liquid chromatography coupled with high resolution mass spectrometry (UPLC-ESI-MS) on enriched phenolic extracts. A total of 71 different compounds were identified, including 32 gallates and gallotannins (of different polymerization degree, from galloyl hexose monomer up to decagalloyl hexoses and undecagalloyl hexoses); seven hydroxybenzophenone (maclurin and iriflophenone) derivatives, six xanthonoids (including isomangiferin and mangiferin derivatives); 11 phenolic acids (hydroxybenzoic and hydroxycinnamic acid derivatives); and eight flavonoids (rhamnetin and quercetin derivatives). The findings for T. Atkins skin constitute the first report of such a high number and diversity of compounds. Also, it is the first time that the presence of gallotannin decamers and undecamers are reported in the skin and flesh of Keitt cultivar and in T. Atkins skins. In addition, total phenolic content (TPC) was measured with high values especially for fruits’ skins, with a TPC of 698.65 and 644.17 mg gallic acid equivalents/g extract, respectively, for Keitt and T. Atkins cultivars. Antioxidant potential using 2,2-diphenyl-1-picrylhidrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) methods were evaluated, with T. Atkins skin showing the best values for both DPPH (IC50 = 9.97 µg/mL) and ORAC (11.02 mmol TE/g extract). A significant negative correlation was found for samples between TPC and DPPH antioxidant values (r = −0.960, p < 0.05), as well as a significant positive correlation between TPC and ORAC (r = 0.910, p < 0.05) and between DPPH and ORAC antioxidant methods (r = 0.989, p < 0.05). Also, cytotoxicity was evaluated in gastric adenocarcinoma (AGS), hepatocarcinoma (HepG2), and colon adenocarcinoma (SW620), with T. Atkins skin showing the best results (IC50 = 138–175 µg/mL). Finally, for AGS and SW 620 cell lines particularly, a high significant negative correlation was found between cytotoxic activity and gallotannins (r = −0.977 and r = −0.940, respectively) while for the HepG2 cell line, the highest significant negative correlation was found with xanthonoids compounds (r = −0.921).
There is an increased interest in plum research because of their metabolites’ potential bioactivities. In this study, the phenolic profiles of Prunus domestica commercial cultivars (Methley, Pisardii and Satsuma) in Costa Rica were determined by Ultra Performance Liquid Chromatography coupled with High Resolution Mass Spectrometry using a quadrupole-time-of-flight analyzer (UPLC-ESI-QTOF MS) on enriched phenolic extracts obtained through Pressurized Liquid Extraction (PLE) under acidic and neutral extraction conditions. In total, 41 different phenolic compounds were identified in the skin and flesh extracts, comprising 11 flavan-3-ols, 14 flavonoids and 16 hydroxycinnamic acids and derivatives. Neutral extractions for the skins and flesh from all of the cultivars yielded a larger number of compounds, and were particularly rich in the number of procyanidin trimers and tetramers when compared to the acid extractions. The total phenolic content (TPC) and antioxidant potential using the DPPH and ORAC methods exhibited better results for neutral extracts with Satsuma skins and Methley flesh, which showed the best values (685.0 and 801.6 mg GAE/g extract; IC50 = 4.85 and 4.39 µg/mL; and 12.55 and 12.22 mmol TE/g extract, respectively). A Two-Way ANOVA for cytotoxicity towards AGS gastric adenocarcinoma and SW620 colon adenocarcinoma indicated a significant difference (p < 0.05) for PLE conditions, with better results for neutral extractions, with Satsuma skin delivering the best results (IC50 = 60.7 and 46.7 µg/mL respectively) along with Methley flesh (IC50 = 76.3 and 60.9 µg/mL, respectively). In addition, a significant positive correlation was found between TPC and ORAC (r = 0.929, p < 0.05), as well as a significant negative correlation (p < 0.05) between TPC and cytotoxicity towards AGS and SW620 cell lines (r = −0.776, and −0.751, respectively). A particularly high, significant, negative correlation (p < 0.05) was found between the number of procyanidins and cytotoxicity against the AGS (r = −0.868) and SW620 (r = −0.855) cell lines. Finally, the PCA clearly corroborated that neutral extracts are a more homogenous group exhibiting higher antioxidant and cytotoxic results regardless of the part or cultivar; therefore, our findings suggest that PLE extracts under neutral conditions would be of interest for further studies on their potential health benefits.
Curcumin (CUR) is a phenolic compound that is safe for human consumption. It exhibits chemopreventive, antiproliferative, antiangiogenic, and antimetastatic effects. However, these benefits can be hampered due to the lipophilic nature, rapid metabolism, low bioavailability, and fast elimination of the molecule. Considering this, the present work reviews the use of CUR-based nanosystems as anticancer agents, including conventional nanosystems (i.e., liposomes, nanoemulsions, nanocrystals, nanosuspensions, polymeric nanoparticles) and nanosystems that respond to external stimuli (i.e., magnetic nanoparticles and photodynamic therapy). Previous studies showed that the effects of CUR were improved when loaded into nanosystems as compared to the free compound, as well as synergist effects when it is co-administrated alongside with other molecules. In order to maximize the beneficial health effects of CUR, critical factors need to be strictly controlled, such as particle size, morphology, and interaction between the encapsulating material and CUR. In addition, there is an area of study to be explored in the development of CUR-based smart materials for nanomedical applications. Imaging-guided drug delivery of CUR-based nanosystems may also directly target specific cells, thereby increasing the therapeutic and chemopreventive efficacy of this versatile compound.
: Pharmaceutical materials which comprise drugs and excipients are mainly organic molecules. These materials frequently exhibit physicochemical properties that can impact formulation, manufacturing and packing processes as well as product performance and safety. In this context, crystal engineering (CE) has intensively grown in recent years as a strategy to reinvent bioactive molecules with well-known and approved pharmacological effects. It aims to improve their physicochemical properties without affecting the molecules’ intrinsic characteristics or compromising their stability. CE is based on molecular recognition involving non-covalent interactions, which in organic materials, are responsible for the regular arrangement of molecules in the crystal lattice. Modern CE encompasses any manipulation that results in an alteration of the crystal packing as well as methods that cause crystal lattice disruption, crystal size reduction or a combination of them. Nowadays, cocrystallization has been the most explore strategy to improve solubility, dissolution rate and bioavailability. However, its combinatorial nature involving two or more small organic molecules, and the use of diverse crystallization processes increase the possible outcomes. As a result, numerous organic materials can be obtained as well as several physicochemical and mechanical properties can be improved. Therefore, this review will focus on novel organic solids obtained when CE is applied including crystalline and amorphous, single and multicomponent as well as nanosized ones, that have contributed to improving not only solubility, dissolution rate, bioavailability permeability but also, chemical and physical stability and mechanical properties.
There is increasing interest in research into fruits as sources of secondary metabolites because of their potential bioactivities. In this study, the phenolic profiles of Malus domestica Anna and Jonagold cultivars from Costa Rica were determined by Ultra Performance Liquid Chromatography coupled with High Resolution Mass Spectrometry (HRMS) using a quadrupole-time-of-flight analyzer (UPLC-QTOF-ESI MS), on enriched-phenolic extracts from skins and flesh, obtained through Pressurized Liquid Extraction (PLE). In total, 48 different phenolic compounds were identified in the skin and flesh extracts, comprising 17 flavan-3-ols, 12 flavonoids, 4 chalcones, 1 glycosylated isoprenoid and 14 hydroxycinnamic acids and derivatives. Among extracts, the flesh of Jonagold exhibits a larger number of polyphenols and is especially rich in procyanidin trimers, tetramers and pentamers. Evaluating total phenolic content (TPC) and antioxidant activities using ORAC and DPPH procedures yields higher values for this extract (608.8 mg GAE/g extract; 14.80 mmol TE/g extract and IC50 = 3.96 µg/mL, respectively). In addition, cytotoxicity evaluated against SW620 colon cancer cell lines and AGS gastric cancer cell lines also delivered better effects for Jonagold flesh (IC50 = 62.4 and 60.0 µg/mL, respectively). In addition, a significant negative correlation (p < 0.05) was found between TPC and cytotoxicity values against SW620 and AGS adenocarcinoma (r = −0.908, and −0.902, respectively). Furthermore, a significant negative correlation (p < 0.05) was also found between the number of procyanidins and both antioxidant activities and cytotoxicity towards SW620 (r = −0.978) and AGS (r = −0.894) cell lines. These results align with Jonagold flesh exhibiting the highest abundance in procyanidin oligomers and yielding better cytotoxic and antioxidant results. In sum, our findings suggest the need for further studies on these Costa Rican apple extracts—and particularly on the extracts from Jonagold flesh—to increase the knowledge on their potential benefits for health.
Curcuma longa constitutes an important source of secondary metabolites that have been associated with multiple health benefits. For instance, curcumin, demethoxycurcumin and bisdemethoxycurcumin, have been found to perform important biological activities, such as anti-inflammatory, antioxidant, anticancer, antimicrobial, antihypertensive and anticoagulant. These promising results prompted this research to evaluate the polyphenols of C. longa rhizomes in Costa Rica. The present work reports a comprehensive study on the polyphenolic profile and the contents of the three main curcuminoids as well as the antioxidant activity of extracts from C. longa rhizomes (n = 12) produced in Costa Rica. Through UPLC-QTOF-ESI MS, a total of 33 polyphenols were identified, grouped in eight types of structures. In addition, our findings on the main curcuminoids using UPLC-DAD show all rhizomes complying with total curcuminoids (TC) content established by the United States Pharmacopeia (USP). At an individual level, samples NW-3 and NE-1 show the higher contents (118.7 and 125.0 mg/g dry material), representing more than twice the average values of the lowest samples. These samples also exhibit the highest Folin–Ciocalteu (FC) reducing capacity results as well as the best DPPH (IC50 15.21 and 16.07 µg extract/mL) and NO (IC50 between 52.5 and 54.3 µg extract/mL) antioxidant values. Further, Pearson correlation analysis findings indicated positive correlation (p < 0.05) between TC, CUR with FC results (r = 0.833 and r = 0.867 respectively) and negative correlation (p < 0.05) between CUR, TC and FC with DPPH results (r = −0.898, r = −0.911, and r = −0.890, respectively) and between NO results and DPPH (r = −0.805, p < 0.05). Finally, results for Principal Component Analysis (PCA) showed composition variability associated with their region of origin with products from the Northeastern (NE) region exhibiting higher average values for FC, TC and antioxidant activities. Further, PCA confirmed that two samples, namely NE-1 and NW-3, stand out by presenting the highest PC1 due to their particularly high TC, CUR and antioxidant activities. Consequently, our findings agree with previous results indicating the importance of C. longa extracts to elaborate products with potential benefits for health, while delivering extracts with higher levels of curcuminoids than previous reports and exhibiting high antioxidant activity.
Bovine Serum Albumin (BSA) lipid hybrid nanoparticles are part of the new solutions to overcome low bioavailability of poor solubility drugs such as curcuminoids, which possess multiple biological advantages; however, they are counterbalanced by its short biological half-life. In this line, we prepared the three main curcuminoids: curcumin (CUR), desmethoxycurcumin (DMC), and bisdemethoxycurcumin (BDM)-loaded BSA nanoparticles. The three formulations were characterized by the average size, size distribution, crystallinity, weight loss, drug release, kinetic mechanism, and antioxidant activity. The developed method produced CUR-, DMC-, and BDM-loaded BSA nanoparticles with a size average of 15.83 ± 0.18, 17.29 ± 3.34, and 15.14 ± 0.14 nm for CUR, DMC, and BDM loaded BSA, respectively. FT-IR analysis confirmed the encapsulation, and TEM images showed their spherical shape. The three formulations achieved encapsulation efficiency upper to 96% and an exhibited significantly increased release from the nanoparticle compared to free compounds in water. The antioxidant activity was enhanced as well, in agreement with the improvement in water release, obtaining IC50 values of 9.28, 11.70, and 15.19 µg/mL for CUR, DMC, and BDM loaded BSA nanoparticles, respectively, while free curcuminoids exhibited considerably lower antioxidant values in aqueous solution. Hence, this study shows promises for such hybrid systems, which have been ignored so far, regarding proper encapsulation, protection, and delivery of curcuminoids for the development of functional foods and pharmaceuticals.
Polymeric lipid hybrid nanoparticles (PLHNs) are the new generation of drug delivery systems that has emerged as a combination of a polymeric core and lipid shell. We designed and optimized a simple method for the preparation of Pluronic F-127-based PLHNs able to load separately demethoxycurcumin (DMC) and bisdemethoycurcumin (BDM). CUR was used as a model compound due to its greater availability from turmeric and its structure similarity with DMC and BDM. The developed method produced DMC and BDM-loaded PLHNs with a size average of 75.55 ± 0.51 and 15.13 ± 0.014 nm for DMC and BDM, respectively. An FT-IR analysis confirmed the encapsulation and TEM images showed their spherical shape. Both formulations achieved an encapsulation efficiency ≥ 92% and an exhibited significantly increased release from the PLHN compared with free compounds in water. The antioxidant activity was enhanced as well, in agreement with the improvement in water dissolution; obtaining IC50 values of 12.74 ± 0.09 and 16.03 ± 0.55 for DMC and BDM-loaded PLHNs, respectively, while free curcuminoids exhibited considerably lower antioxidant values in an aqueous solution. Hence, the optimized PHLN synthesis method using CUR as a model and then successfully applied to obtain DMC and BDM-loaded PLHNs can be extended to curcuminoids and molecules with a similar backbone structure to improve their bioactivities.
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