Pomolic Acids Research Articles

Nuts as functional foods: Variation of nutritional and phytochemical profiles and their in vitro bioactive properties.

The aim of the present study was to examine the nutritional (fat, fatty acids, minerals, sugars) and bioactive compounds (polyphenols, tocochromanols, triterpene) and their influence on in vitro anti-diabetic (pancreatic α-amylase and intestinal α-glucosidase), anti-obesity (pancreatic lipase) and anti-cholinergic (AChE and BuChE) inhibitory activity of 8 different popular nuts-pecan, pine, hazelnuts, pistachio, almonds, cashew, walnuts, and macadamia. The total content of phenolic compounds in nuts ranged from 432.9 (walnuts) to 5.9 (pistachio) mg/100g. The dominant polyphenols are polymeric procyanidins (walnuts - 415.1mg/100g). Nuts are rich in tocochromanols (832.9-4377.5μg/100g), especially α- and γ-tocopherols. The highest content of α-tocopherol (vitamin E) was detected in hazelnuts and almonds (2551.0 and 2489.7μg/100g, respectively) while the lowest amounts were detected in macadamia, cashew and walnuts. The most abundant in nuts are oleanic and pomolic acids (35 and 22% of total, respectively), while betulin, uvaol and erythrodiol are less characteristic triterpenes for nuts (<1%). Pine nuts are the nuts with the highest content of triterpene (690.3mg/100g). Pistachio and almonds are the richest in total fat (>45%), but monounsaturated (17.5-79.3%; hazelnuts, almonds, cashew, macadamia, pistachio and pecan) and polyunsaturated (7.5-69.3%; pine, walnuts) are the dominant fatty acids. Moreover, nuts are low in Cu, Zn, Mn and Na content, but rich in K (464.5-1772.3mg/100g) and Mg (197.0-502.5mg/100g). Macadamia, walnuts and cashew are good sources of Se. Pistachio, almonds and cashew were characterized by the highest content of sugars, but the dominant sugar was saccharose (58.2-2399.3mg/100g). All nuts showed high activity in inhibiting intestinal α-glucosidase (>90%), but lower ability to inhibit pancreatic α-amylase and pancreatic lipase activity. The activity in inhibiting acetyl- and butylcholinesterase was up to 30%. As described above, all nuts contain various compounds that improve the nutritional value. Therefore they should be one of the important components of the daily human diet rich in functional foods.

Bioguided identification of pentacyclic triterpenoids as anti-inflammatory bioactive constituents of Ocimum gratissimum extract

Ethnopharmacological relevanceOcimum gratissimum is a plant spice widely used in African traditional medicine to treat pain-related conditions. However, the anti-inflammatory mechanisms underlying this activity and the main active ingredients in O. gratissimum have not yet been fully characterized. Aim of the studyTo isolate and identify the main anti-inflammatory active constituents of Ocimum gratissimum extract and their underlying mechanisms in murine macrophages. Material and methodsChromatographic techniques and spectroscopic data were used for compounds isolation and identification. Inflammatory conditions were produced in cultured RAW 264.7 macrophage cells by the application of lipopolysaccharide (LPS). The WST-1 assay was used to evaluate the cell viability, and the nitric oxide production was quantified by the Griess reagent method. The fluorometric cyclooxygenase (COX) activity assay kit was used to assess the activity of COX-1 and COX-2 enzymes. The levels of IFN-γ, TNF-α, IL-2, IL-4, IL-6, and IL-10 cytokines and the apoptosis-inducing effect were measured by flow cytometer using the cytometric Bead Array (CBA) Human Th1/Th2 Cytokine Kit II and FITC Annexin V Apoptosis Detection kit, respectively. ResultsThe results showed that the extract and fractions of Ocimum gratissimum inhibit nitric oxide production and the proliferation of Raw 264.7 macrophage cells. The bioguided fractionation led to the identification of pentacyclic triterpenes as anti-inflammatory bioactive compounds. Pomolic and tormentic acids being the most active, inhibiting the secretion of IFN-γ cytokine, COX enzyme, and inducing apoptosis in activated Raw 264.7 macrophage cells. ConclusionsThis study revealed that pomolic and tormentic acids are the main active principles responsible at least in part for the anti-inflammatory effect of the extract of Ocimum gratissimum. Besides of providing more evidence for the traditional use of Ocimum gratissimum against inflammatory disorders, this study reveals the multitarget potential of pomolic and tormentic acids as promising future drugs against inflammatory diseases.

Extraction of Cecropia Pachystachya Leaves by Supercritical Carbon Dioxide: Kinetics, Phytochemical Characterization, Antibacterial and Antioxidant Activities

Cecropia pachystachya Trécul is popularly known in Brazil as embaúva or embaúba. Pharmacological activities were reported in extant studies including the development of anxiolytic, antidepressant, hypoglycemic, antioxidant, cardiotonic, sedative, anti-inflammatory, antimicrobial and leishmanicidal properties for aqueous and alcoholic extracts prepared by infusion or maceration of C. pachystachya leaves. However, there is a paucity of studies examining extracts of leaves of C. pachystachya obtained by supercritical fluid technology. This study evaluated the extraction of Cecropia pachystachya oil using supercritical carbon dioxide (CO2). Extractions were performed at 35 °C, 45 °C, and 55 °C and 14 MPa, 17 MPa, and 20 MPa. The extraction yield, characteristics of the oil, antioxidant and antibacterial potentials were evaluated. The highest extraction yield obtained from C. pachystachya leaves was 1.48% using supercritical CO2 at 55 °C and 20 MPa. The main identified compounds include terpenoids (ursolic and pomolic acids, squalene and β-sitosterol). The most promising results for antibacterial activity relative to Staphylococcus aureus and antioxidant potentials were observed on the extract obtained at 55 °C and 14 MPa. The mathematical Sovová model satisfactorily represented the experimental data.

Triterpene Acid and Phenolics from Ancient Apples of Friuli Venezia Giulia as Nutraceutical Ingredients: LC-MS Study and In Vitro Activities

Triterpene acid and phenolic constituents from nine ancient varieties of apple (Malus domestica) fruits cultivated in Fanna, Friuli Venezia Giulia region, northeast Italy, were analyzed and compared with four commercial apples (‘Golden Delicious’, ‘Red Delicious’, ‘Granny Smith’ and ‘Royal Gala’). Total phenolic and flavonoid contents were measured by spectrophotometric assays. The quali-quantitative fingerprint of secondary metabolites including triterpene acid was obtained by LC-DAD-(ESI)-MS and LC-(APCI)-MS, respectively. Based on the two LC-MS datasets, multivariate analysis was used to compare the composition of ancient fruit varieties with those of four commercial apples. Significant differences related mainly to the pattern of triterpene acids were found. Pomolic, euscaphyc, maslinic and ursolic acids are the most abundant triterpene in ancient varieties pulps and peels, while ursolic and oleanolic acids were prevalent in the commercial fruits. Also, the content of the phenolic compounds phloretin-2-O-xyloglucoside and quercetin-3-O-arabinoside was greater in ancient apple varieties. The antioxidant (radical scavenging, reducing power, metal chelating and phosphomolybdenum assays) and enzyme inhibitory effects (against cholinesterase, tyrosinase, amylase and glucosidase) of the samples were investigated in vitro. Antioxidant assays showed that the peels were more active than pulps. However, all the samples exhibited similar enzyme inhibitory effects. Ancient Friuli Venezia Giulia apple cultivars can be a source of chlorogenic acid and various triterpene acids, which are known for their potential anti-inflammatory activity and beneficial effects on lipid and glucose metabolism. Our results make these ancient varieties suitable for the development of new nutraceutical ingredients.

Fragmentation of the main triterpene acids of apple by LC-APCI-MSn.

In this paper, we investigated the fragmentation of the main triterpene acids of apple using an liquid chromatography atmospheric pressure chemical ionization mass spectrometry (LC-APCI-MSn ) approach and high-resolution mass spectrometry (HR-MS) (Q-TOF). Triterpenes were isolated using semipreparative high-performance liquid chromatography, and chemical structures were elucidated by HR-MS and nuclear magnetic resonance spectroscopy. Finally, compounds were used to study MSn behavior in ion trap. Isolated triterpenes present similar structures, bearing carboxyl group linked to C-17 and different substitutions. We observed significant changes in MS2 spectra, which were useful for further compound identification. The observed fragments allowed the discrimination of different derivatives, namely, pomaceic, annurcoic, euscaphic, pomolic, corosolic, maslinic, betulinic, oleanolic, and ursolic acids. The proposed method allows a rapid identification of triterpene acids, and it could be useful for the analysis of these compounds in apple fruits and in other natural sources.

Apoptosis as the basic mechanism of cytotoxic action of ursolic and pomolic acids in glioma cells

Apoptosis as the basic mechanism of cytotoxic action of ursolic and pomolic acids in glioma cells

Apoptosis as the basic mechanism of cytotoxic action of ursolic and pomolic acids in glioma cells

Pentacyclic triterpene acids are of great interest as compounds that exhibit selective cytotoxicity against malignant tumor cells. If earlier studies were carried out mainly in cancer cells of epithelial origin, in the present work the cytotoxic effect of ursolic and pomolic acids on the primary and permanent glioma cell lines was analyzed. Both compounds are toxic to oncotransformed cells and induce apoptosis in U-87 MG line. Using molecular docking, it has been shown that Akt1 and MDM2 may be potential targets of the studied triterpene acids. It has been suggested that ursolic and pomolic acids induce apoptosis in glioma cells through inhibition of the PI3K/Akt signaling pathway, and they can be considered as potentially promising agents for the treatment of glioblastoma.

Pharmacogenomic Characterization of Cytotoxic Compounds from Salvia officinalis in Cancer Cells.

Salvia officinalis is used as a dietary supplement with diverse medicinal activity (e.g. antidiabetic and antiatherosclerotic effects). The plant also exerts profound cytotoxicity toward cancer cells. Here, we investigated possible modes of action to explain its activity toward drug-resistant tumor cells. Log10IC50 values of two constituents of S. officinalis (ursolic acid, pomolic acid) were correlated to the expression of ATP-binding cassette (ABC) transporters (P-glycoprotein/ABCB1/MDR1, MRP1/ABCC1, BCRP/ABCG2) and epidermal growth factor receptor (EGFR) or mutations in RAS oncogenes and the tumor suppressor gene TP53 of the NCI panel of cell lines. Gene expression profiles predicting sensitivity and resistance of tumor cells to these compounds were determined by microarray-based mRNA expressions, COMPARE, and hierarchical cluster analyses. Furthermore, the binding of both plant acids to key molecules of the NF-κB pathway (NF-κB, I-κB, NEMO) was analyzed by molecular docking. Neither expression nor mutation of ABC transporters, oncogenes, or tumor suppressor genes correlated with log10IC50 values for ursolic acid or pomolic acid. In microarray analyses, many genes involved in signal transduction processes correlated with cellular responsiveness to these compounds. Molecular docking indicated that the two plant acids strongly bound to target proteins of the NF-κB pathway with even lower free binding energies than the known NF-κB inhibitor MG-132. They interacted more strongly with DNA-bound NF-κB than free NF-κB, pointing to inhibition of DNA binding by these compounds. In conclusion, the lack of cross-resistance to classical drug resistance mechanisms (ABC-transporters, oncogenes, tumor suppressors) may indicate a promising role of the both plant acids for cancer chemotherapy. Genes involved in signal transduction may contribute to the sensitivity or resistance of tumor cells to ursolic and pomolic acids. Ursolic and pomolic acid may target different steps of the NF-κB pathway to inhibit NF-κB-mediated functions.

Chemical constituents of Distictella elongata (Vahl) Urb. (Bignoniaceae)

Pectolinarin, a flavone heteroside, was isolated from Distictella elongata (Vahl) Urb. leaves ethanol extract, along with a mixture of ursolic, pomolic and oleanolic acids, besides β-sitosterol. Their structures were established on the basis of spectral analysis (1H and 13C NMR, 1D and 2D) and they were compared with literature. This is the first report on the occurrence of this flavonoid in a species of the Bignoniaceae family.

Antiviral activity of Distictella elongata (Vahl) Urb. (Bignoniaceae), a potentially useful source of anti-dengue drugs from the state of Minas Gerais, Brazil

To investigate the in vitro antiviral activity of Distictella elongata (Vahl) Urb. ethanol extracts from leaves (LEE), fruits (FEE), stems and their main components. The antiviral activity was evaluated against human herpesvirus type 1 (HSV-1), murine encephalomyocarditis virus (EMCV), vaccinia virus Western Reserve (VACV-WR) and dengue virus 2 (DENV-2) by the 3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) colorimetric assay. LEE presented anti-HSV-1 [EC(50) 142.8 ± 5.3 μg ml(-1); selectivity index (SI) 2.0] and anti-DENV-2 activity (EC(50) 9.8 ± 1.3 μg ml(-1) ; SI 1.5). The pectolinarin (1) isolated from LEE was less active against HSV-1 and DENV-2. A mixture of the triterpenoids ursolic, pomolic and oleanolic acids was also obtained. Ursolic and oleanolic acids have shown antiviral activity against HSV-1. A mixture of pectolinarin (1) and acacetin-7-O-rutinoside (2) was isolated from FEE and has presented anti-DENV-2 activity (EC(50) 11.1 ± 1.6 μg ml(-1) ; SI > 45). Besides the antiviral activity, D. elongata has disclosed antioxidant effect. These data shows that D. elongata has antiviral activity mainly against HSV-1 and DENV-2, besides antioxidant activity. These effects might be principally attributed to flavonoids isolated. Distictella elongata might be considered a promising source of anti-dengue fever phytochemicals.

A New Acylated Triterpene from the Roots of Chaenomeles japonica.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Pentacyclic triterpenes from Chrysobalanaceae species: cytotoxicity on multidrug resistant and sensitive leukemia cell lines

Plants are known as important source in the search for new anti-cancer agents. Cytotoxicity-guided fractionation of leaves and fruits from Licania tomentosa Bench and leaves from Chrysobalanus icaco L. resulted in the isolation of betulinic, oleanolic and pomolic acids. These triterpenoids inhibited the growth and induced apoptosis of K562, an erythroleukemia cell line. Most importantly, they also inhibited the proliferation of Lucena 1, a vincristine-resistant derivative of K562 that displays several multidrug resistance (MDR) characteristics. Taken together, our findings emphasize the anti-tumor activity of these triterpenes on leukemia cell lines and call attention to their potential as anti MDR agents.

A new acylated triterpene from the roots of Chaenomeles japonica.

A new acylated triterpene together with prunasin, (-)-epicatechin, daucosterol, and three triterpenes, ursolic, oleanolic, and pomolic acids was isolated from the root of Chaenomeles japonica (THUNB.) LINDL. (Rosaceae) and determined to be 3-O-(E)-3, 5-dihydroxycinnamoylursolic acid on the basis of NMR and FAB-MS experiments.