Oleanolic Acid Research Articles

Systematic elucidation of the multi-target pharmacological mechanism of Terminalia arjuna against congestive cardiac failure via network pharmacology and molecular modelling approaches

Congestive cardiac failure (CCF) is a pathophysiologic state when the heart is not able to maintain its cardiac output to meet the demand of metabolising tissues. CCF is responsible for approximately 2.9 million deaths worldwide. The heterogeneous nature of CCF draws the attention of researchers to find more enthralling and promising diagnostic and treatment options. Terminalia arjuna (Arjuna) is an evergreen, deciduous tree exhibited various astringent, anti-bacterial, and anti-microbial properties. T. arjuna is being used in various regions for anginal pain, hypertension, congestive heart failure, and dyslipidemia. Although previous in vitro studies have demonstrated the therapeutic potential of T. arjuna, the exact molecular mechanism underlying its protective effect on the heart remains unclear. In this study, a network pharmacology technique was used to explore the active ingredients, potential targets in T. arjuna for the treatment of CCF. In the framework of this study, we explored the active ingredient–target–pathway network and figured out that oleanolic acid, arjunolic acid, luteolin, kaempferol, cholesterol, ellagic acid 4-O-xylopyranoside 3,3’-dimethyl ether, and cyclohexyl (2,4-dimethyl phenyl) methanone contributed significantly to the development of CCF by affecting AKT1, MAPK14, TNF, IL6, ESR1, and HSP90AA1 genes. Molecular docking analysis further validated the activities of these compounds against potential targets. To sum up, integrated network pharmacology and docking analysis revealed that T. arjuna exerts its cardioprotective effect by acting on various signalling pathways, including the thyroid hormone, VEGF signalling pathway, AGE-RAGE signalling pathway in diabetic complications, HIF signalling pathway, sphingolipid signalling pathway, and oestrogen signalling pathways. Overall, this study provides valuable insights into the molecular mechanism of T. arjuna in CCF and highlights its potential as a promising preventive treatment for this condition.

Study on the accumulation pattern of anthocyanins, sugars and organic acids in medicinal Vitis vinifera ‘SuoSuo’ during ripening

In this study, targeted metabolomics technology was used to accurately and quantitatively analyze the metabolic pathways of anthocyanin, sugars and organic acid metabolites during the ripening of ‘SuoSuo’ grape berries. Results, 33, 10 and 36 metabolites of anthocyanins, sugars and organic acids, respectively, were detected. The anthocyanin with the highest content was cyanidin-3-O-glucoside (136.343 ng/g), which reached a maximum at 135 days after full bloom. The highest fructose content in sugar was 167.69 ng/g (135 days after full bloom). Among the organic acids, tartaric acid exhibited the highest content (37,196.67 mg/kg, 105 days after full bloom). The content of oleanolic acid (230.064 mg/kg, 135 days after full bloom) was higher in organic acids. These results clarify how anthocyanin, sugar and organic acid metabolites accumulate and change as ‘SuoSuo’ grapes ripen and provide a reference for the development and utilization of ‘SuoSuo’.

Hexaphenyl-butadiene derivative with aggregation-induced emission characteristic for high-sensitive detection of ursolic acid, oleanolic acid, and glycyrrhizic acid

Plant natural products (PNPs) have a wide range of pharmacological effects and biological activities, including antitumor, antiinflammatory, antibacterial, and antiviral properties. These properties can be beneficial for their use in the health care industry. As representative PNPs, ursolic acid (UA), oleanolic acid (OA), and glycyrrhizic acid (GA) have been efficiently biosynthesized in microbial cells. In this study, hexaphenyl-butadiene methylpyridine salt (HPB-I) with an aggregation-induced emission characteristic (AIE) was developed as a simple, real-time, and efficient quantitative probe for detection of PNPs. Experimental results showed that HPB-I has a highly selective fluorescence response to UA, OA, and GA among 18 PNPs. Three detection methods were employed. Dilution of a PNP aqueous solution with dimethyl sulfoxide was optimal with low limits of detection of 0.16 (UA), 0.23 (OA), and 0.066 (GA) nmol/mL. Scanning electron microscopy, dynamic light scattering, and zeta potential analyses revealed that the PNPs were effectively adsorbed on the surface of HPB-I aggregates, which resulted in an increase in the fluorescence response based on restriction of intramolecular motion. HPB-I could also effectively and quantitatively detect the three PNPs in a synthetic dropout (SD) culture medium. This study provides a valuable approach toward the development of a real-time low-cost method for in-situ PNP detection of biosynthesis processes in microbial cells.

Potentials of Terpenoids as Inhibitors of Multiple Plasmodium falciparum Protein Drug Targets.

The resistance of parasite to readily affordable antimalarial drugs, the high cost of currently potent drugs, and the resistance of vector mosquitoes to insecticides threaten the possibility of malaria eradication in malaria endemic areas. Due to the fact that quinine and artemisinin were isolated from plants sources, researchers have been encouraged to search for new antimalarials from medicinal plants. This is especially the case in Africa where a large percentage of the population depends on medicinal plant to treat malaria and other ailments. In this study, we evaluated previously characterized Plasmodium-cidal compounds obtained from the African flora to identify their likely biochemical targets, for an insight into their possible antimalarial chemotherapy. Molecular docking study was first conducted, after which remarkable compounds were submitted for molecular dynamic (MD) simulations studies. From a total of 38 Plasmodium-cidal compounds docked with confirmed Plasmodium falciparum protein drug targets [plasmepsin II (PMII), histo-aspartic protein (HAP) and falcipain-2 (FP)], two pentacyclic triterpene, cucurbitacin B and 3 beta-O-acetyl oleanolic acid showed high binding affinity relative to artesunate. This implies their capacity to inhibit the three selected P. falciparum target proteins, and consequently, antimalarial potential. From the MD simulations studies and binding free energy outcomes, results confirmed that the two compounds are stable in complex with the selected antimalarial targets; they also showed excellent binding affinities during the 100 ns simulation. These results showed that cucurbitacin B and 3 beta-O-acetyl oleanolic acid are potent antimalarials and should be considered for further studies.

Interactions of Oleanolic Acid, Apigenin, Rutin, Resveratrol and Ferulic Acid with Phosphatidylcholine Lipid Membranes—A Spectroscopic and Machine Learning Study

Biologically active compounds present in the diet can interact with biological membranes (such as cell membranes), changing their properties. Their mutual interactions can influence their respective activities. In this study, we analyzed the interactions of oleanolic acid and phenolic compounds such as apigenin, rutin, resveratrol and ferulic acid with phosphatidylcholine membranes. Spectroscopic methods (fluorescence spectroscopy, dynamic light scattering) and machine learning were applied. The results of structural studies were compared with the antioxidant activity of the investigated substances in lipid membranes. In liposomes loaded with oleanolic acid, the pro-oxidant activity of resveratrol arises from changes in membrane structure, leading to an increased exposure of its hydrophilic region to external radicals. A similar mechanism may be involved in the pro-oxidant action of oleanolic acid. By contrast, apigenin, rutin and ferulic acid are present at the membrane surface. Their presence in this region protects the bilayer from radicals generated in the aqueous phase. Lower antioxidant activity observed in the case of ferulic aid is probably related to weaker interactions of this compound with the membrane, compared to the investigated flavonoids. Appropriate machine learning models for predicting oleanolic acid and phenolic compounds have been developed for the future application of intelligent predictive systems to optimizing manufacturing processes involving liposomes. The most effective regression model turned out to be the MLP 1:1-100-50-50-6:1, identifying resveratrol with a determination index of 0.83.

Reductive Aldol Approach to Natural Products: Bioinspired Synthesis of abeo-11(12 → 13)-Oleanane Triterpenoids.

A synthesis of alstoscholarinoid B (1) and 3β-acetoxy-11α-hydroxy-11(12 → 13)abeooleanan-12-al (2) has been accomplished in 7-9 steps and 10%-16% overall yield from oleanolic acid. This synthesis featured a bioinspired SmI2-mediated reductive aldol reaction to establish the abeo-11(12 → 13)-oleanane framework of both 1 and 2 and a retro-aldol/aldol/lactonization cascade to fully construct the skeleton of 1. Moreover, the investigation of the bioinspired aldol reaction also sheds light on the potential biogenesis of natural products.

Melatonin-mediated alleviation of drought stress by modulation of physio-biochemical and metabolic status in Dracocephalum kotschyi Boiss. (Lamiaceae)

Dracocephalum kotschyi Boiss., a fragrant perennial plant belonging to the Lamiaceae family, contains many bioactive substances, including essential oil, terpenoids, phenolics, and flavonoids that possess a wide range of biological and pharmaceutical properties. Due to the importance of plant exploitation in dry and low-yield lands, the present study was conducted to explore the effect of the exogenous application of melatonin (0, 50, 100, 150, and 200 μM) on physiological, biochemical, and phytochemical traits of the plant subjected to different levels of water deficit stress (80 %, 60 %, and 40 % of field capacity). The results showed that the application of 150 μM melatonin caused the highest content in the relative growth rate (1.84 g/g d), chlorophyll content (14.55 mg/g FW), relative water content (93 %), and chlorophyll fluorescence (0.9) at different irrigation regimes. Reduced irrigation significantly reduced chlorophyll content and fluorescence, while exogenously applied melatonin enhanced their contents at all levels. Reduced irrigation caused a significant increase in the levels of malondialdehyde (7.47 µmol/g FW) and hydrogen peroxide (51.86 nmol/g). Total phenol content, antioxidant activity, and antioxidant power were increased by applying of melatonin up to 200 μM, while the irrigation rate decreased. The essential oil content was increased by reducing irrigation, so the highest content (3.0 % w/w) was observed at 40 % FC and 150 μM melatonin. Geranyl acetate (44.6–60.4 %), α-pinene (9.0–19.1 %), and geranial (6.2–16.2 %) were the major essential oil components of the treated plants. Reduced irrigation and application of melatonin up to 150 μM caused an increase in coumaric acid, rosmarinic acid, and rutin despite a decrease in the content of chicoric acid and apigenin. The highest oleanolic acid content (52.69 mg/g DW) was measured in the plants subjected to 40 % FC. The highest (132 mg/g DW) and lowest (43.58 mg/g DW) ursolic acid content was measured in 40 % FC with 200 μM melatonin and 80 % FC without melatonin treatment, respectively.

α-Glucosidase Inhibitors Based on Oleanolic Acid for the Treatment of Immunometabolic Disorders

Using oleanolic acid as a starting compound, a series of new oleanane-type triterpenic derivatives were synthesized via O-acylation (with nicotinic, isonicotinic, and methoxycinnamic acid acyl chlorides), N-amidation (with cyclic- or polyamines), the Mannich reaction (with secondary cyclic amines), and Claisen–Schmidt condensation (with aromatic aldehydes), and their potencies as treatments for immunometabolic disorders were investigated. The compounds were evaluated against α-glucosidase and PTP1B enzymes and LPS-stimulated murine macrophages. It was found that the target compounds are highly effective α-glucosidase inhibitors but lack activity against PTP1B. A leading compound, N-methylpiperazine methylated 2,3-indolo-oleanolic propargyl amide 15, is also a micromolar inhibitor of NO synthesis in LPS-stimulated macrophages and suppresses oxidative bursts in neutrophils with similar efficiency. These results, in addition to its ability to stimulate glucose uptake in rat fibroblasts and improve maltose tolerance in rats, allow us to consider compound 15 a promising prototype drug for the treatment of immunometabolic defects in type 2 diabetes.

Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

A new compound, C23H20BrN3OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å3. The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R22(14) and R22(16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.

Antimicrobial, Cytotoxic, and α-Glucosidase Inhibitory Activities of Ethanol Extract and Chemical Constituents Isolated from Homotrigona apicalis Propolis-In Vitro and Molecular Docking Studies.

The chemical investigation of Homotrigona apicalis propolis collected in Binh Dinh province, Vietnam, led to the isolation of nine compounds, including four sesquiterpenes: spathulenol (1), 1αH,5βH-aromandendrane-4β,10α-diol (2), 1β,6α-dihydroxy-4(15)-eudesmene (3), and 1βH,5βH-aromandendrane-4α,10β-diol (4); three triterpenes: acetyl oleanolic acid (5), 3α-hydroxytirucalla-8,24-dien-21-oic acid (6), and ursolic acid (7); and two xanthones: cochinchinone A (8) and α-mangostin (9). Sesquiterpens 1-4 and triterpene 6 were isolated for the first time from stingless bee propolis. Plants in the Cratoxylum and Aglaia genus were suggested as resin sources of the propolis sample. In the antibacterial activity evaluation, the EtOH extract only showed moderate activity on S. aureus, while the isolated compounds 7-9 showed good antibacterial activity, with IC50 values of 0.56 to 17.33 µg/mL. The EtOH extract displayed selective cytotoxicity against the A-549 cancer cell line, with IC50 values of 22.82 ± 0.86 µg/mL, and the xanthones 8 and 9 exhibited good activity against the KB, HepG-2, and A-549 cancer cell lines, with IC50 values ranging from 7.55 ± 0.25 µg/mL to 29.27 ± 2.07 µg/mL. The cytotoxic effects of xanthones 8 and 9 were determined by the inhibition of the EGFR and HER2 pathways using a molecular docking study. Compounds 8 and 9 displayed strong binding affinity with EFGR and HER2, with values of -9.3 to -9.9 kcal/mol. Compounds 5, 8, and 9 showed potential α-glucosidase inhibitory activities, which were further confirmed by computational studies. The binding energies of compounds 5, 8, and 9 were lower than that of arcabose.

Effects of oleanolic acid and ursolic acid on depression-like behaviors induced by maternal separation in mice

Oleanolic acid (OA) and ursolic acid (UA) are structural isomeric triterpenoids. Both triterpenoids have been reported to be able to improve depression. However, no studies have compared their effects in the same system. Whether OA or UA could ameliorate depression-like behaviors in maternal separation (MS)-induced depression-like model was investigated. MS model is a well-accepted mouse model that can reflect the phenotype and pathogenesis of depression. Depression is a mental illness caused by neuroinflammation or changes in neuroplasticity in certain brain regions, such as the prefrontal cortex and hippocampus. Depression-like behaviors were measured using splash test or forced swimming test. In addition, anxiety-like behaviors were also measured using the open field test or elevated plus-maze test. MS-treated female mice showed greater depression-like behaviors than male mice, and that OA improved several depression-like behaviors, whereas UA only relieved anxiety-like behavior of MS-treated mice. Microglial activation, expression levels of TNF-α, and mRNA levels of IDO1 were increased in the hippocampi of MS-treated female mice. However, OA and UA treatments attenuated such increases. In addition, expression levels of synaptophysin and PSD-95 were decreased in the hippocampi of MS-treated female mice. These decreased expression levels of synaptophysin were reversed by both OA and UA treatments, although decreased PSD-95 expression levels were only reversed by OA treatment. Our findings suggest that MS cause depression-like behaviors through female-specific neuroinflammation, changes of tryptophan metabolism, and alterations of synaptic plasticity. Our findings also suggest that OA could reverse MS-induced depression-like behaviors more effectively than UA.

Multi-component content determination of Dracocephalum tanguticum by quantitative analysis of multi-components by single-marker

This study aims to establish a method for the simultaneous determination of 7 active components in Dracocephalum tanguticum and to evaluate the quality of medicinal materials from different habitats. The method was established with high performance liquid chromatography(HPLC) and the gradient elution was performed with the mobile phase of acetonitrile-methanol-0.2% phosphoric acid solution at a column temperature of 35 ℃, an injection volume of 15 μL, and a flow rate of 0.6 mL·min~(-1). The detection wavelength was set as 215 nm. With rosmarinic acid as the internal reference, the relative correction factors and the content of other 6 components were calculated. The results were compared with those obtained with the external standard method. The results showed that the samples from Huangzhong county, Qinghai province had the best quality, with the highest content of p-hydroxybenzoic acid, cosmosiin, rosmarinic acid, oleanolic acid, and ursolic acid(9.29, 12.14, 6.02, 3.11, 17.67 mg·g~(-1) respectively). The samples from Chaya county, Tibet autonomous region ranked the second, with the highest content of betulin and betulinic acid(15.53, 7.17 mg·g~(-1), respectively). The method is accurate, reliable, and repeatable and suitable for the simultaneous determination of multiple components in D. tanguticum. The content of functional components varied in the samples from different producing areas and can be used as the indicator for the quality evaluation of medicinal materials.

Bioinspired Gram-Scale Synthesis of Alstoscholarinoid B.

Herein, we describe a gram-scale synthesis of alstoscholarinoid B, a rearranged triterpenoid with potent antihyperuricemic bioactivity. This synthesis was inspired by the biogenetic hypothesis and achieved in seven steps from oleanolic acid with an overall yield of 51%.

Berberine oleanolic acid complex salt grafted hyaluronic acid/silk fibroin (BOA-g-HA/SF) composite scaffold promotes cartilage tissue regeneration under IL-1β caused stress

Since inflammatory cytokines cause stress to chondrocytes and the failure of cartilage defects repair with cartilage tissue engineering, it is necessary to develop a scaffold to maintain cartilage regeneration under inflammatory factors caused stress. Following a berberine-oleanolic acid (OA) complex salt (BOA) was grafted to hyaluronic acid (HA) to obtain water soluble BOA-g-HA, it mixed with silk fibroin (SF) to prepared 4 solutions, which contained 30 mg/mL SF and 0.75, 1.5, 2.25, and 3.0 mg/mL BOA-g-HA respectively. They were lyophilized to fabricate BOA-g-HA/SF-1, BOA-g-HA/SF-2, BOA-g-HA/SF-3, and BOA-g-HA/SF-4 composite scaffolds respectively. All prepared scaffolds displayed porous network structure and exhibited promising mechanical properties for tissue engineering applications. Among them, the BOA-g-HA/SF-3 composite scaffold showed the highest influence on maintaining chondrocytic phenotype of chondrocytes under IL-1β induced stress. Following SF, HA/SF, and BOA-g-HA/SF-3 composite scaffolds with seeded chondrocytes were treated with IL-1β induction for 1 week, specimens were incubated with cell culture medium for 3 week or were subcutaneously implanted into nude mice for 4 weeks. The results demonstrated that the BOA-g-HA/SF-3 composite scaffold promotes cartilage tissue regeneration in vitro and in vivo under IL-1β caused stress, suggesting that it can be potential applied for repairing cartilage defects in osteoarthritis patients.

Network Pharmacology and Molecular Docking Reveal the Mechanism of Isodon ternifolius (D. Don) Kudo Against Liver Fibrosis.

Many studies have demonstrated the hepatoprotective or anti-fibrotic effects of Isodon ternifolius, but its pharmacological basis and mechanism remain unclear. In this study, we used in vitro models to validate the predicted results and revealed the potential mechanism of action and active ingredients through network pharmacology methods and molecular docking. The chemical components of Isodon ternifolius were identified by literatures. Potential targets of Isodon ternifolius were predicted by Swiss Target Prediction. The disease targets were collected through the databases of Gene Card. Common targets of Isodon ternifolius and liver fibrosis were obtained by online tool Venny 2.1. PPI protein interaction network was obtained using String database, and target protein interaction network was drawn using Cytoscape software. Signaling pathway enrichment analysis was performed on drug-disease targets with of DAVID database. Twenty-one potential active ingredients and 298 potential targets were predicted by Swiss Target Prediction platform. Ninety pathways related to liver fibrosis were obtained by KEGG enrichment. The TLR4, MAPK and PI3K-Akt signaling pathways are mostly associated with liver fibrosis. Molecular docking techniques were used to validate the core target proteins TNF, Akt1, MAPK1, EGFR and TLR4 binding to the ingredients of Isodon ternifolius, which showed that a multitude of ingredients of Isodon ternifolius were able to bind to the above target proteins, especially 2α-hydroxy oleanolic acid and (-)-Lambertic acid. Our experimental validation results showed that Isodon ternifolius inhibited the activation of PI3K-Akt and ERK1/2 signaling pathways. Through a network pharmacology approach and in vitro cell assay, we predicted and validated the active compounds of Isodon ternifolius and its potential targets for LF treatment. The results suggest that the mechanism of Isodon ternifolius treating LF by inhibiting angiogenesis may be related to the ERK1/2 and PI3K/Akt signaling pathways.

Molecular Docking and Pharmacokinetic Prediction of Potential Compounds from Luffa acutangula as Antidiabetic Candidates

Luffa acutangula is commonly used, but its considerable potential as an alternative treatment for diabetics with a molecular target action is not yet known. Preliminary study of bioinformatics to decipher the compounds of L. acutangulaable to interact with the protein targets of antidiabetic therapy. This study aims to identify the potential compounds of L. acutangula that are thought to interact with the insulin receptor, aldose reductase, and PTP-1B, as well as provide predictions of pharmacokinetics and toxicity. Molecular docking was conducted in AutoDock 4.2.6 with the stages initiated by the preparation of macromolecules (PDB ID: 1IR3; 2PEV; 4Y14) and ligands, molecular docking, and visualization. The pharmacokinetic profiles are predictable by using the Swiss ADME and toxicity estimates by Toxtree. The results showed that cucurbitacin B, cucurbitacin E, oleanolic acid, catechin, ferulic acid and apigenin are the most potential compounds to interact with the macromolecular with a binding energy response similar to the native ligand. Pharmacokinetic predictions show that cucurbitacin B and cucurbitacin E deviate from one Lipinski rule (BM> 500), do not diffuse into the blood brain barrier, are not CYP450 inhibitors, as well as classified as Pgp substrates. The prediction of toxicity indicates that all potential compounds are classified as high toxicity compounds with a risk of narcosis, except oleanolic acid and ferulic acid. These compounds are not genotoxic or non-genotoxic carcinogens.

Unlocking the Potential: Novel NSAIDs Hybrids Unleash Chemopreventive Power toward Liver Cancer Cells through Nrf2, NF-κB, and MAPK Signaling Pathways.

HCC is a highly aggressive malignancy with limited treatment options. In this study, novel conjugates of non-steroidal anti-inflammatory drugs (NSAIDs)-Ibuprofen and Ketoprofen-with oleanolic acid oximes derivatives (OAO) were synthesized, and their activity as modulators of signaling pathways involved in HCC pathogenesis was evaluated in normal THLE-2 liver cells, and HCC-derived HepG2 cells. The results demonstrated that conjugation with OAO derivatives reduces the cytotoxicity of parent compounds in both cell lines. In THLE-2 cells, treatment with conjugates resulted in increased activation of the Nrf2-ARE pathway. An opposite effect was observed in HepG2 cells. In the later reduction of NF-κB, it was observed along with modulation of MAPK signaling pathways (AKT, ERK, p38, p70S6K, and JNK). Moreover, STAT3, STAT5, and CREB transcription factors on protein levels were significantly reduced as a result of treatment with IBU- and KET-OAO derivatives conjugates. The most active were conjugates with OAO-morpholide. Overall, the findings of this study demonstrate that IBU-OAO and KET-OAO derivative conjugates modulate the key signaling pathways involved in hepatic cancer development. Their effect on specific signaling pathways varied depending on the structure of the conjugate. Since the conjugation of IBU and KET with OAO derivatives reduced their cytotoxicity, the conjugates may be considered good candidates for the prevention of liver cancer.

Lavandula austroapennina: Assessment of the Antiviral Activity of Lipophilic Extracts from Its Organs.

In a framework aimed at the recovery and enhancement of medicinal plants endemic to the territory of the Cilento and Vallo di Diano National Park, Lavandula austroapennina N.G. Passal., Tundis and Upson has aroused interest. An insight into the chemical composition of the corolla, calyx, leaf, stem, and root organs was carried out following ultrasound-assisted maceration in n-hexane. The obtained lipophilic extracts were explored using ultra-high-performance chromatography coupled to high-resolution mass spectrometry (UHPLC-ESI-QqTOF-MS/MS). The extracts from the different organs varied in their relative content of fatty acids, ursanes, and oleanane-type triterpenes. In particular, the oleanolic acid content appeared to increase in the order of corolla < leaf < stem. An MTT assay was performed to verify the possible cytotoxicity of the organ extracts of L. austroapennina at a concentration ranging from 12.5 to 400 µg/mL on the Vero CCL-81 cell line. Antiviral activity against herpes simplex virus type 1 (HSV-1), alpha human coronavirus 229E (HCoV-229E), and poliovirus type 1 (PV-1) was evaluated via a plaque reduction assay in the same cellular model. All the extracts did not show cytotoxic effects after 2 and 24 h exposure times, and the antiviral efficacy was particularly important for the stem extract, capable of completely inhibiting the tested viruses at low doses. The antiviral activity in a non-enveloped virus PV-1 allowed the assertion that the extracts from the organs of L. austroapennina, and especially the stem extract, interfered directly with the viral envelope. This study underlines how much knowledge of a territory's medicinal plant heritage is a harbinger of promising discoveries in the health field.

Gypsogenin Battling for a Front Position in the Pentacyclic Triterpenes Game of Thrones on Anti-Cancer Therapy: A Critical Review-Dedicated to the Memory of Professor Hanaa M. Rady.

In the last decade, gypsogenin has attracted widespread attention from medicinal chemists by virtue of its prominent anti-cancer potential. Despite its late identification, gypsogenin has proved itself as a new anti-proliferative player battling for a frontline position among other classic pentacyclic triterpenes such as oleanolic acid, glycyrrhetinic acid, ursolic acid, betulinic acid, and celastrol. Herein, we present the most important reactions of gypsogenin via modification of its four functional groups. Furthermore, we demonstrate insights into the anti-cancer activity of gypsogenin and its semisynthetic derivatives and go further by introducing our perspective to judiciously guide the prospective rational design. The present article opens a new venue for a better exploitation of gypsogenin chemical entity as a lead compound in cancer chemotherapy. To the best of our knowledge, this is the first review article exploring the anti-cancer activity of gypsogenin derivatives.

Novel molecularly imprinted aerogels: Preparation, characterization, and application in selective separation for oleanolic acid in lingonberry

An oleanolic acid (OA) surface molecularly imprinted polymer silylated porous composite aerogels (OA-MIP@Si-PC-aerogels) adsorbent material was successfully prepared and characterized. The material not only has a great selectivity for the target molecule OA but also has other noteworthy qualities including high stability, excellent repeatability, and a sizable adsorption capacity. via cellulose and sodium alginate as the main materials, the carrier Si-PC-aerogels were made through ionic cross-linking, chemical cross-linking, and silylation procedures. By adopting a surface molecular imprinting approach on Si-PC-aerogels, OA-MIP@Si-PC-aerogels were effectively created utilizing OA as the template molecule and MAA as the functional monomer. Due to the presence of a specific imprinted layer on the aerogel surface, the adsorption capacity of OA-MIP@Si-PC-aerogels for OA could reach 66.20 mg g−1. OA-MIP@Si-PC-aerogels could achieve a 68.86% yield of OA from the extracts of lingonberry (Vaccinium Vitis-Idaea L.). The adsorption capacity remained at 90% after five consecutive adsorption-desorption cycles. HepG2 cells were exposed to OA that was effectively enriched with OA-MIP@Si-PC-aerogels in lingonberry (Vaccinium Vitis-Idaea L.) fruit homogenates. This OA significantly inhibited the growth of HepG2 cells in vitro. It further demonstrated that OA-MIP@Si-PC-aerogels could efficiently target OA enrichment and separation with good recovery.