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This work aimed to evaluate chemical profile, antioxidant activity and topical application safety of the raw Osage orange (Maclura pomifera (Raf.) Schneid) fruit extracts obtained by maceration using ethanol and acetone. Out of eighteen different compounds registered in the extracts, fifteen were identified by ultra-high-performance liquid chromatography-tandem mass spectrometry. Pomiferin and osajin were characteristic and representative compounds in both ethanolic and acetone extracts of the Osage orange fruit. Both extracts showed good antioxidant activity (EC50 = 0.03 mg/cm3) after 20 min of incubation. The topical administration safety of the extracts was evaluated in vivo by measuring skin biophysical parameters: electrical capacitance and erythema index, as indicators of stratum corneum hydration and irritation, respectively. Based on the results of the in vivo skin tests, it can be concluded that both of the Osage orange fruit extracts are safe for topical administration - they increased skin hydration and reduced skin irritation under the occlusion. [ABSTRACT FROM AUTHOR]

Despite efforts to find effective drugs for sepsis-associated acute kidney injury (SA-AKI), mortality rates in patients with SA-AKI have not decreased. Our study evaluated the protective effects of isoflavone osajin (OSJ) on SA-AKI in rats by targeting inflammation, oxidative stress, and apoptosis, which represent the cornerstones in the pathophysiological mechanism of SA-AKI. Polymicrobial sepsis was induced in rats via the cecal ligation and puncture (CLP) technique. Markers of oxidative stress were evaluated in kidney tissues using biochemical methods. The expression of interleukin-33 (IL-33), 8-hydroxydeoxyguanosine (8-OHdG), caspase-3, and kidney injury molecule-1 (KIM-1) was evaluated as indicators of inflammation, DNA damage, apoptosis, and SA-AKI respectively in the kidney tissues using immunohistochemical and immunofluorescent detection methods. The CLP technique significantly (p

This paper aimed to examine the impact of flavonoid osajin (OSJ) on liver damage induced by sepsis. A total of 30 male rats were divided into 5 groups (Sham, sepsis, OSJ 150, OSJ 300 and reference). During sepsis, elevated lipid peroxidation (LPO) level and catalase activity (CAT) and decreased glutathione (GSH) level and superoxide dismutase (SOD) activity were observed in hepatic tissues of sepsis group in comparison with Sham group. A strong interleukin-33 and caspase-3 expressions were detected in hepatic tissues of sepsis group. On the contrary, OSJ administration to OSJ 300 group showed a significant decrease (P < 0.001) in LPO level (176±2.926) and significant increase (P < 0.001) in GSH level (10.586±0.083) and SOD activity (29.152±0.094) in comparison with sepsis group (185.777±1.735, 8.246±0.124, 24.307±0.379 respectively). In addition, the consumption of OSJ reduced expressions of interleukin-33 and caspase-3 and improved histopathological integrity. In conclusions, OSJ has hepatoprotective effect against sepsis-induced liver injury.

This paper aimed to examine the impact of flavonoid osajin (OSJ) on liver damage induced by sepsis. A total of 30 male rats were divided into 5 groups (Sham, sepsis, OSJ 150, OSJ 300 and reference). During sepsis, elevated lipid peroxidation (LPO) level and catalase activity (CAT) and decreased glutathione (GSH) level and superoxide dismutase (SOD) activity were observed in hepatic tissues of sepsis group in comparison with Sham group. A strong interleukin-33 and caspase-3 expressions were detected in hepatic tissues of sepsis group. On the contrary, OSJ administration to OSJ 300 group showed a significant decrease (P < 0.001) in LPO level (176±2.926) and significant increase (P < 0.001) in GSH level (10.586±0.083) and SOD activity (29.152±0.094) in comparison with sepsis group (185.777±1.735, 8.246±0.124, 24.307±0.379 respectively). In addition, the consumption of OSJ reduced expressions of interleukin-33 and caspase-3 and improved histopathological integrity. In conclusions, OSJ has hepatoprotective effect against sepsis-induced liver injury. [ABSTRACT FROM AUTHOR]

Objectives: Maclura pomifera (Rafin.) Schneider is a widespread species all around the world, which is also frequently cultured for ornamental purposes. Previous studies revealed that M. pomifera fruits are rich in prenylated isoflavonoids, exhibit noteworthy biological activities, and have probable benefits, particularly, when applied topically. Considering that phenolic compounds are important sources in the development of antiaging cosmetic products, this study investigated the anti-aging potential of M. pomifera 80% methanolic extract (MPM) by evaluating antioxidant and extracellular matrix degrading enzymes inhibiting activity. Materials and Methods: For this study, the inhibitory potential of 80% MPM against different enzymes associated with the aging process was evaluated. Given the unequivocal role of oxidative stress in aging, in vitro antioxidant tests were employed as well. Moreover, osajin was determined as the major bioactive isoflavonoid of the sample by high performance thin layer chromatography analysis. Results: Results of the mechanistically different antioxidant assays exhibited notable antioxidant potential of the extract. Inhibition potential of MPM against hyaluronidase, collagenase, and elastase enzymes, which are directly linked to acceleration of the aging process, was investigated and results revealed that MPM inhibited the aforementioned enzymes explicitly. MPM had notable phenolic and flavonoid content; 113.92 ± 2.26 mg gallic acid equivalent/g and 66.41 ± 0.74 mg QE/g, respectively. When total antioxidant capacity assays were considered, it is possible to suggest that MPM is a promising anti-aging agent. Conclusion: As a result, this study discloses that extracts of fruits of M. pomifera have significant anti-aging potential and may be used for this purpose. [ABSTRACT FROM AUTHOR]

Flemingia macrophylla merupakan tumbuhan perdu yang termasuk keluarga Fabaceae. Senyawa fenolik Flemingia mengandung senyawa flavonoid dan isoflavonoid. Penelitian ini bertujuan untuk menentukan aktivitas sitotoksik senyawa isoflavonoid dari Flemingia macrophylla terhadap sel kanker payudara T47D. Ekstraksi dan isolasi senyawa isoflavonoid menggunakan metanol pada suhu kamar. Dua senyawa isoflavonoid terisoprenilasi, 8-(1.1-dimetil-prop-2-enil) genistein (1) dan osajin (2) telah berhasil dipisahkan dari ranting Flemingia macrophylla. Penentuan struktur senyawa isoflavonoid menggunakan data spektroskopi ultraviolet (UV), inframerah (IR), 1D dan 2D NMR. Sitotoksik 8-(1.1-dimetil-prop-2-enil) genistein (1) dan osajin (2) terhadap sel kanker payudara T47D memperlihatkan nilai IC50 sebesar 10,91 ± 0,17 dan 3,72 ± 0,23 µg/mL.

Osage orange trees (Maclura pomifera (Raf.) C.K.Schneid.) are distributed worldwide, particularly in south-east states of the USA. They produce large quantities of strong yellow fruits, bigger than oranges, but these fruits are inedible, with an acid milky juice which is little consumed by birds and insects. Extracts prepared from Osage orange fruits (hedge apple) have revealed a range of pharmacological properties of interest in human and veterinary medicine. In addition, Osage orange extracts can be used in agriculture and aquaculture, and as dyeing agent for the textile industry. Extracts contain potent antioxidant compounds, notably the isoflavonoids pomiferin and auriculasin, together with other terpenoids and flavonoids. The structural characteristics and pharmacological properties of the major prenylated isoflavones isolated from M. pomifera are discussed here, with a focus on the two phenolic compounds osajin and warangalone, and the two catechol analogues pomiferin and auriculasin. The mechanisms at the origin of their potent antioxidant and anti-inflammatory effects are presented, notably inhibition of xanthine oxidase, phosphodiesterase 5A and kinases such as RKS2 and kRAS. Osajin and auriculasin display marked anticancer properties, owing to their ability to inhibit tumor cell proliferation, migration and tumor angiogenesis. Different molecular mechanisms are discussed, including osajin‑copper complexation and binding to quadruplex DNA. An overview of the mechanism of action of the prenylated isoflavones from Osage orange is presented, with the objective to promote their knowledge and to raise opportunities to better exploit the fruits of Osage orange, abundant but largely neglected at present. [Display omitted] • Osage orange (Maclura pomifera) trees produce large quantities of an inedible fruit, little exploited. • Extracts of Osage orange exhibit a range of useful properties to combat human pathologies. • Four main prenylated isoflavonoids can be extracted from the fruits, notably osajin and pomiferin. • The isoflavonoids display marked antioxidant and anti-inflammatory properties. • The potential applications of the plant and its phytochemicals are discussed. [ABSTRACT FROM AUTHOR]

Amethod for assay of total isoflavonoids in an oil extract of the osage orange by spectrophotometry in the visible part of the spectrum was developed, based on selective interaction of aluminum chloride solution with compounds of flavonoid structure. The results were validated by their demonstrated specificity and the linear relationship between optical density and product concentration, with a correlation coefficient of r = 0.9988, with satisfactory reproducibility with a relative error of the mean result of ±2.57%. [ABSTRACT FROM AUTHOR]

The aim of this study is to purify carbonic anhydrase I and II isoenzymes from human erythrocyte, isolate two natural products osajin (OSJ) and pomiferin (PMF) fromMaclura pomiferafruits, and evaluate thein vitroeffect of these natural metabolites on these isoenzymes. These natural products may be used as starting points for drug discovery (like drugs used in several therapeutic applications, including antiglaucoma activity). For the purification procedure, the Sepharose-4B-l-tyrosine-sulphonamide affinity chromatography was used. Column chromatography and thin layer chromatography methods were used for isolation of OSJ and PMF fromM. pomiferafruits and their chemical structures were elucidated by IR, 1D, and 2D NMR methods. We compared inhibitory effects of these natural products with inhibitory effects of phenolic compounds and found that these products demonstrated average inhibition effects. We thought that this study will give inspiration to scientists interested in this issue. [ABSTRACT FROM AUTHOR]

The article discusses a study which assessed the antioxidant potential of various extracts obtained from the leaf and fruit of Maclura pomifera, Schneider and its major isoflavonoids. Topics covered include findings which show the antioxidant capacity of iso-osajin, iso-pomiferin, and macluraxanthone, and indications that pomiferin is a natural possible antioxidant agent.

omiferin and osajin have been isolated from the acetonic extract of M. pomifera fruits. Effects of total acetonic extract, pomiferin and osajin on the autooxidation of purified sunflower triacylglycerol were studied. Pomiferin showed a high antioxidant activity whereas total acetonic extract showed moderate and osajin revealed a low activity.

Reactive oxygen species (ROS) and inflammation play important roles in the pathogenesis of ischemia/reperfusion (I/R) ovarian injury. The purpose of this in-vivo study is to evaluate the effect of osajin, a prenylated flavonoid with antioxidant and anti-inflammatory properties, on oxidative balance and ovarian damage induced by unilateral I/R. The study used 48 adult, female Wistar albino rats. In the controls (CN), only laparotomy was performed. In group CNOsajin, 200 mg/kg osajin was administered. In group IRWHICLE, an ischemic period of 3 h was followed by reperfusion for 3 lithe bilateral ovaries were then removed. In groups and IROsajin100, and IROsajin200 after 3 h of ischemia, 100 and 200 mg/kg of osajin was given orally before reperfusion, respectively; after 3 h of reperfusion, the ovaries were removed. After the experiments, MPO, SOD and CAT enzyme activities and LPO levels was determined for the oxidative state and activities of PMNs. In addition, histopathological changes were examined in all rat ovarian tissues. Statistical analysis was performed using one-way ANOVA (with Duncan). According to biochemical and histopathological results, l/R increased LPO levels and MPO activities and infiltration of PMNs despite high-antioxidant SOD and CAT enzyme activity. Both dosage levels of osajin before I/R significantly decreased LPO level and MPO activity and PMN infiltration compared to those of the IRVEHICLE group, with the higher dosage causing greater decreases. In addition, results showed that treatment with osajin against ameliorated development of irreversible ovarian damage induced by I/R. These results suggest that osajin provides protections against ovarian I/R injury. Its mechanisms could be related to mitigation of oxidative stress and activities and to PMN infiltration. [ABSTRACT FROM AUTHOR]

Pomiferin and osajin are major bioactive isoflavones found in Maclura pomifera (Rafin.) Schneider (Moraceae). A simple, reproducible, and sensitive method for analysis of pomiferin and osajin in different parts of M. pomifera has been developed and validated. The compounds were separated on a C8 column by gradient elution at a flow rate at 1.0 mL min−1. Column eluent was monitored at 280 nm by use of a diode-array detector. Linear range, peak purity, selectivity, system performance, precision, accuracy, and robustness were shown to be acceptable. LC–MS with atmospheric pressure electrospray ionization was used for identification of the compounds; use of positive-ion mode resulted in protonated pseudomolecular ions of the compounds. [ABSTRACT FROM AUTHOR]

Heteroleptic copper(II) complexes, containing prenylated flavonoid osajin isolated from the fruits of Maclura pomifera Schneid., were prepared and thoroughly characterized, including single crystal X-ray analysis. Some of the following complexes of the general composition [Cu(L)(bpy)]NO 3 (1), [Cu(L)(dimebpy)]NO 3 ·2MeOH (2) [Cu(L)(phen)]NO 3 ·H 2 O (3), [Cu(L)(bphen)]NO 3 (4) and [Cu(L)(dppz)]NO 3 (5), where HL stands for 3-(4-hydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-ene-1-yl)-4 H ,8 H -benzo[1,2- b :3,4- b' ]dipyran-4-one (osajin), bpy = 2,2′-bipyridine, dimebpy = 4,4′-dimethyl-2,2′-bipyridine, phen = 1,10-phenanthroline, bphen = 4,7-diphenyl-1,10-phenanthroline and dppz = dipyrido[3,2- a :2′,3′- c ]phenazine, were also monitored for their solution stability and interactions with cysteine and glutathione by mass spectrometry. The in vitro cytotoxicity of the complexes was evaluated against a panel of eight human cancer cell lines: (MCF-7, HOS, A549, PC-3, A2780, A2780R, Caco-2, and THP-1). The results revealed high antiproliferative activity of the complexes with the best IC 50 values of 0.5–3.4 μM for complexes (4) and (5), containing the bulkier N , N' -donor ligands (bphen, and dppz, respectively). The complexes also revealed a relatively low toxicity towards human hepatocytes (IC 50 values are higher than 100 μM in some cases), and thus proved to be highly selective towards the cancer cells. On the other hand, the complexes showed a strong in vitro nuclease effect using the model pUC-19 plasmid. In the model of lipopolysaccharide-stimulated (LPS) THP-1 monocytes, the complexes revealed ability to lower the activity of nuclear factor kappa-B/activator protein 1 (NF-κB /AP-1) system and decrease the secretion of tumor necrosis factor alpha (TNF-α). Thus, the complexes have been identified as strong antiproliferative and anti-inflammatory compounds. [Display omitted] • Heteroleptic Cu(II) complexes with prenylated flavonoid osajin are reported. • Complexes revealed significant in vitro cytotoxicity on eight human cancer cell lines. • Complexes showed negligible toxicity against human hepatocytes. • Complexes induce oxidative stress, initiate apoptosis and cleave pUC19 plasmid DNA. • Complexes inhibit nuclear factor kappa-B activity and tumor necrosis factor alpha levels. [ABSTRACT FROM AUTHOR]

The major constituents of fruits of Maclura pomifera are the prenylated isoflavones, osajin (1) and pomiferin (2). Since significant biological activities of extracts from the wood of M. pomifera were previously reported, the peroxynitrite scavenging activity, inhibition of lipid peroxidation, scavenging of DPPH and EROD activity of these two major substances were studied. [Copyright &y& Elsevier]

Background: Currently, antiprostate cancer (PCa) drugs, including androgen deprivation therapy (ADT), are initially effective; however, most patients with PCa who receive ADT eventually progress to deadly aggressiveness. There is an urgent need to seek alternative strategies to cure this lethal disease. Activation of lipogenesis has been demonstrated to lead to PCa progression. Therefore, targeting the aberrant lipogenic activity could be developed therapeutically in PCa. The aim of this study is to investigate the molecular basis and efficacy of osajin, a bioactive prenylated isoflavonoid, in PCa., Methods: PCa cells, LNCaP (androgen-sensitive) and C4-2 (androgen-insensitive/castration-resistant), were used in this study. Proliferation, migration, and invasion analyses were conducted by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method, a wound healing assay, and the transwell method. Lipogenesis was determined by a Fatty Acid Quantification Kit and oil red O staining. Apoptosis was assessed by annexin V-fluorescein isothiocyanate/propidium iodide staining, caspase enzymatic activity, and Western blot analyses., Results: Osajin inhibited fatty acid synthase (FASN) expression, a key enzyme for lipogenesis, in PCa cells. By inhibiting FASN, osajin decreased the fatty-acid levels and lipid accumulation. Significantly, osajin downregulated androgen receptor (AR) and prostate-specific antigen (PSA) in PCa cells. Moreover, osajin suppressed PCa cell growth, migration, and invasion. Through activation of the caspase-dependent pathway, osajin induced apoptosis in PCa cells., Conclusions: These data provide a novel molecular basis of osajin in PCa cells, and cotargeting lipogenesis and the AR axis via impairment of FASN and AR expression by osajin could be applied as a new and promising approach for the treatment of malignant PCa., (© 2019 Wiley Periodicals, Inc.)

Solar ultraviolet light (sUV) has been shown to promote the development of skin disorders including inflammation, photoaging, and skin carcinogenesis. Osajin is the major bioactive isoflavone present in the fruit of Maclura pomifera, commonly referred to as the Osage orange. In this study, we observed that osajin inhibited sUV-induced cyclooxygenase (COX)-2 protein expression in both HaCaT and JB6 cells. COX-2 is a major mediator of skin inflammation. sUV activated the transcription factors nuclear factor-κB and activator protein-1 which, in turn, induces COX-2 expression. Osajin inhibited transactivation of these transcription factors. We identified RSK2 as an inhibitory target of osajin by screening against 68 kinases related to inflammation. Osajin binds with RSK2 directly in an ATP-competitive manner. Computer modeling simulated a plausible binding orientation between osajin and RSK2. Osajin inhibited sUV-induced phosphorylation of histone H3, a substrate of RSK2. However, sUV-induced phosphorylation of extracellular signal-regulated kinases, p38 kinase, c-Jun N-terminal kinase and Akt, which are signaling factors upstream of RSK2, was unchanged in the presence of osajin. The anti-inflammatory effects and molecular mechanism of osajin suggest that it may have utility as a functional food for skin health and cosmetic ingredient. J. Cell. Biochem. 118: 4080-4087, 2017. © 2017 Wiley Periodicals, Inc., (© 2017 Wiley Periodicals, Inc.)

The fruit of the osage orange tree, Maclura pomifera (Raf) Schneid (Moraceae), has long been thought to be repellent to insects. A preliminary study reported here confirmed repellency of fruit extracts to the maize weevil, Sitophilus zeamais Motschulsky. Two isofiavones, osajin and pomiferin, were isolated from the mature fruit of M. potnifera in high purity (?95%). Testing of purified osajin and pomiferin failed to show repellency. Repellency is likely caused by factors other than isoflavones in the fruit. [ABSTRACT FROM AUTHOR]