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Auraptene

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https://www.readbyqxmd.com/read/30283705/auraptene-inhibits-migration-and-invasion-of-cervical-and-ovarian-cancer-cells-by-repression-of-matrix-metalloproteinasas-2-and-9-activity
#1
Khadijeh Jamialahmadi, Sofia Salari, Nafiseh Sadat Alamolhodaei, Amir Avan, Leila Gholami, Gholamreza Karimi
Objectives: Auraptene, a natural citrus coumarin, found in plants of Rutaceae and Apiaceae families. In this study, we investigated the effects of auraptene on tumor migration, invasion and matrix metalloproteinase (MMP)-2 and -9 enzymes activity. Methods: The effects of auraptene on the viability of A2780 and Hela cell lines was evaluated by MTT assay. Wound healing migration assay and Boyden chamber assay were determined the effect of auraptene on migration and cell invasion, respectively...
September 2018: Journal of Pharmacopuncture
https://www.readbyqxmd.com/read/30126250/inhibitory-effects-of-auraptene-and-naringin-on-astroglial-activation-tau-hyperphosphorylation-and-suppression-of-neurogenesis-in-the-hippocampus-of-streptozotocin-induced-hyperglycemic-mice
#2
Satoshi Okuyama, Tatsumi Nakashima, Kumi Nakamura, Wakana Shinoka, Maho Kotani, Atsushi Sawamoto, Mitsunari Nakajima, Yoshiko Furukawa
Auraptene, a citrus-related compound, exerts anti-inflammatory effects in peripheral tissues, and we demonstrated these effects in the brains of a lipopolysaccharide-injected systemic inflammation animal model and a brain ischemic mouse model. Naringin, another citrus-related compound, has been shown to exert antioxidant effects in several animal models. Hyperglycemia induces oxidative stress and inflammation and causes extensive damage in the brain; therefore, we herein evaluated the anti-inflammatory and other effects of auraptene and naringin in streptozotocin-induced hyperglycemic mice...
August 19, 2018: Antioxidants (Basel, Switzerland)
https://www.readbyqxmd.com/read/29972213/auraptene-in-the-peels-of-citrus-kawachiensis-kawachibankan-contributes-to-the-preservation-of-cognitive-function-a-randomized-placebo-controlled-double-blind-study-in-healthy-volunteers
#3
M Igase, Y Okada, M Ochi, K Igase, H Ochi, S Okuyama, Y Furukawa, Y Ohyagi
OBJECTIVES: Dementia, which is characterized by a progressive decline in cognitive function, is a major concern in aging societies. Although a number of treatments have been approved, an effective therapy to prevent the disorder is lacking. A supplement that improves cognitive function would benefit patients. The aim of this study was to assess whether auraptene, a citrus coumarin, has a protective effect on cognitive decline. DESIGN: A randomized, placebo-controlled, double-blind study SETTING: Outpatient medical check-up program for cognitive disorders PARTICIPANTS: 84 adult volunteers (they are cognitively normal) met inclusion and exclusion criteria to participate...
2018: Journal of Prevention of Alzheimer's Disease
https://www.readbyqxmd.com/read/29747740/auraptene-regulates-th-1-th-2-t-reg-balances-nf-%C3%AE%C2%BAb-nuclear-localization-and-nitric-oxide-production-in-normal-and-th-2-provoked-situations-in-human-isolated-lymphocytes
#4
Vahid Reza Askari, Vafa Baradaran Rahimi, Seyed Abdolrahim Rezaee, Mohammad Hossein Boskabady
BACKGROUND: Auraptene as member of dietary coumarins, is found in citrus fruits. Former studies have demonstrated its anti-inflammatory and anti-cancer activity. PURPOSE: The mechanism of action and immune-modulatory property of this compound on human lymphocytes are greatly unknown. STUDY DESIGN/METHODS: The effect of three concentrations (10, 30 and 90 µM) of auraptene or dexamethasone (0.1 mM) were evaluated on percentage of cell proliferation and nitric oxide (NO) production as well as secretion and gene expression of cytokines, and NF-κB level in PHA-stimulated and non-stimulated lymphocytes...
April 1, 2018: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/29730190/natural-oxyprenylated-coumarins-are-modulators-of-melanogenesis
#5
Serena Fiorito, Francesco Epifano, Francesca Preziuso, Ivana Cacciatore, Antonio di Stefano, Vito Alessandro Taddeo, Philippe de Medina, Salvatore Genovese
Naturally occurring coumarins 7-isopentenyloxycoumarin, auraptene, and umbelliprenin are able to modulate the biosynthesis of melanin in murine Melan-a cells probably through the interaction with selected biological targets like estrogen receptor β and aryl hydrocarbon receptor. Such a modulation strictly depends on the individual structure of the coumarin: the presence of a 3,3-dimethylallyloxy side chain is a structural determinant for tanning activation whereas a farnesyl one leads to the opposite effect...
May 25, 2018: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/29721568/hepatoprotection-of-auraptene-from-peels-of-citrus-fruits-against-thioacetamide-induced-hepatic-fibrosis-in-mice-by-activating-farnesoid-x-receptor
#6
Xiaoguang Gao, Changyuan Wang, Chenqing Ning, Kexin Liu, Xinyuan Wang, Zhihao Liu, Huijun Sun, Xiaodong Ma, Pengyuan Sun, Qiang Meng
Hepatic fibrosis is a pathological process that eventually leads to the development of cirrhosis and liver cancer by various types of chronic liver disease. To date, there is no standard treatment for the progression of liver fibrosis. This study aims to investigate the hepatoprotection of auraptene (AUR), a simple coumarin contained in the peels of citrus fruits such as grapefruit, against thioacetamide (TAA)-induced hepatic fibrosis in mice. The involvement of farnesoid X receptor (FXR) in the anti-fibrotic effect of AUR was further elucidated using in vivo and in vitro experiments...
May 23, 2018: Food & Function
https://www.readbyqxmd.com/read/29619675/a-new-terpene-coumarin-microbial-transformed-by-mucor-polymorphosporus-induces-apoptosis-of-human-gastric-cancer-cell-line-mgc-803
#7
Guangzhi Li, Junchi Wang, Xiaojin Li, Jianguo Xu, Zhao Zhang, Jianyong Si
2'-Z auraptene (1) is a synthesized monoterpene coumarin with anticancer activity against human gastric cancer cells. In order to find new potential anticancer agent, Mucor polymorphosporus was used to transform cis-auraptene. Four new terpene coumarins with notable changes in the skeletal backbone, 2'-Z auraptene A-D (2-5), were obtained and evaluated for their antiproliferative effects against human normal gastric epithelium cells and human gastric cancer cells. These new compounds showed selective cytotoxic activity against MGC-803 cells with IC50 values from 0...
June 2018: Archives of Pharmacal Research
https://www.readbyqxmd.com/read/29549856/analysis-of-biologically-active-oxyprenylated-phenylpropanoids-in-tea-tree-oil-using-selective-solid-phase-extraction-with-uhplc-pda-detection
#8
Luca Scotti, Salvatore Genovese, Tonino Bucciarelli, Filippo Martini, Francesco Epifano, Serena Fiorito, Francesca Preziuso, Vito Alessandro Taddeo
An efficient analytical strategy based on different extraction methods of biologically active naturally occurring oxyprenylated umbelliferone and ferulic acid derivatives 7-isopentenyloxycoumarin, auraptene, umbelliprenin, boropinic acid, and 4'-geranyloxyferulic acid and quantification by UHPLC with spectrophotometric (UV/Vis) detection from Tea tree oil is reported. Absorption of the pure oil on Al2 O3 (Brockmann activity II) prior washing the resulting solid with MeOH and treatment of this latter with CH2 Cl2 resulted the best extraction methodology in terms of yields of oxyprenylated secondary metabolites...
May 30, 2018: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/29527955/antidepressant-like-effect-of-casimiroa-pubescens-root-extracts
#9
Denisse Ubaldo-Suárez, Rosa Estrada Reyes, Roberto De la Rosa-Sierra, Mariano Martínez-Vázquez
In this study, we investigated the antidepressant-like effects of the hexane (HCP), ethyl acetate (ECP) and methanol (MCP) extracts of the roots of Casimiroa pubescens Ramírez (Rutaceae) using the forced swim test (FST). In an initial experiment, each extract was orally administered to mice only once 60 min before to the FST. In a second experiment, doses were administered 24, 7 and 1 h before testing. Our results showed that the triple administration of the extracts provided a stronger effect than single administration...
March 12, 2018: Natural Product Research
https://www.readbyqxmd.com/read/29413613/preparation-characterization-and-optimization-of-auraptene-loaded-solid-lipid-nanoparticles-as-a-natural-anti-inflammatory-agent-in-vivo-and-in-vitro-evaluations
#10
Sara Daneshmand, Mahmoud Reza Jaafari, Jebrail Movaffagh, Bizhan Malaekeh-Nikouei, Mehrdad Iranshahi, Atieh Seyedian Moghaddam, Zahra Tayarani Najaran, Shiva Golmohammadzadeh
Auraptene (AUR) is a bioactive antioxidant coumarin with valuable pharmacological properties; however, poor water solubility is a substantial issue for the topical application of AUR. Therefore, we sought to prepare solid lipid nanoparticles (SLNs) containing AUR (AUR-SLNs) to enhance its anti-inflammatory effect. The prepared formulations were optimized by applying the response surface method. Furthermore, AUR-SLNs were compared to conventional cream containing AUR regarding both the permeation rate of the nanoparticles and the anti-inflammatory effect through both in vitro and in vivo studies...
April 1, 2018: Colloids and Surfaces. B, Biointerfaces
https://www.readbyqxmd.com/read/29287412/a-green-deep-eutectic-solvent-dispersive-liquid-liquid-micro-extraction-des-dllme-for-the-uhplc-pda-determination-of-oxyprenylated-phenylpropanoids-in-olive-soy-peanuts-corn-and-sunflower-oil
#11
Vincenzo Ferrone, Salvatore Genovese, Maura Carlucci, Matteo Tiecco, Raimondo Germani, Francesca Preziuso, Francesco Epifano, Giuseppe Carlucci, Vito Alessandro Taddeo
A green dispersive liquid-liquid microextraction (DLLME) using deep eutectic solvent (DES) as the extracting solvent has been developed and applied for the simultaneous quantification of ferulic acid, umbelliferone, boropinic acid, 7-isopentenyloxycoumarin, 4'-geranyloxyferulic acid (GOFA), and auraptene in some vegetable oils using ultra high performance liquid chromatography (UHPLC) with photodiode array detection (PDA). All parameters in the extraction step, including selection and loading of both extracting and dispersing solvents, amount of both extractant and disperser solvent were investigated and optimized...
April 15, 2018: Food Chemistry
https://www.readbyqxmd.com/read/29144746/oxyprenylated-phenylpropanoids-bind-to-mt1-melatonin-receptors-and-inhibit-breast-cancer-cell-proliferation-and-migration
#12
Mahmud Hasan, Salvatore Genovese, Serena Fiorito, Francesco Epifano, Paula A Witt-Enderby
Oxyprenylated compounds (i.e., ferulic acid and coumarin derivatives) demonstrate neuroprotection and anticancer properties as reported in previous studies. We have tested the affinity of oxyprenylated ferulic acid (1-4) and umbelliferone derivatives (5-11) to melatonin receptors as well as their antiproliferation and antimigratory properties against breast cancer (BC) cell lines. All the compounds except for ferulic acid, boropinic acid, and umbelliferone had binding affinities to melatonin receptors in the nM to μM range, and both auraptene and umbellinprenin reduced BC cell proliferation and migration in phenotypically diverse BC including triple negative...
December 22, 2017: Journal of Natural Products
https://www.readbyqxmd.com/read/29080847/safety-evaluation-of-auraptene-in-rats-in-acute-and-subacute-toxicity-studies
#13
Tooraj Vakili, Mehrdad Iranshahi, Hosseinali Arab, Bamdad Riahi, Nama Mohammadian Roshan, Gholamreza Karimi
Auraptene (AUR) is a natural, bioactive, monoterpene coumarin ether. It has anti-inflammatory, anti-carcinogenic, anti-bacterial, neuroprotective, and hepatoprotective properties. The aim of the present study was to assess the acute and subacute toxicity of oral administration of AUR in rats by evaluating clinical signs, haematology, biochemical factors, pathological changes and immune-toxicity. Acute administration of AUR in doses of 125, 250, 500, 1000 and 2000 mg/kg body weight had no mortality or clinical signs in a period of two days...
December 2017: Regulatory Toxicology and Pharmacology: RTP
https://www.readbyqxmd.com/read/28987596/computational-discovery-and-experimental-verification-of-farnesoid-x-receptor-agonist-auraptene-to-protect-against-cholestatic-liver-injury
#14
Xiaoguang Gao, Ting Fu, Changyuan Wang, Chenqing Ning, Yulong Kong, Zhihao Liu, Huijun Sun, Xiaodong Ma, Kexin Liu, Qiang Meng
Recently obeticholic acid (OCA) which is a farnesoid X receptor (FXR) agonist was approved by FDA to treat cholestatic liver diseases, which provided us a novel therapeutic strategy against cholestasis. Herein, we used a novel computational strategy with two-dimensional virtual screening for FXR agonists. For the first time, we found that auraptene (AUR), a natural product, can activate FXR to exert hepatoprotective effect against cholestatic liver injury in vivo and in vitro. Importantly, AUR was found to significantly decrease the mortality of cholestatic mice...
December 15, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28915362/efficacy-of-hyperthermia-in-human-colon-adenocarcinoma-cells-is-improved-by-auraptene
#15
Mahdi Moussavi, Farhang Haddad, Maryam M Matin, Mehrdad Iranshahi, Fatemeh B Rassouli
Colon adenocarcinoma is one of the most common cancers worldwide, and resistance to current therapeutic modalities is a serious drawback in its treatment. Auraptene is a natural coumarin with considerable anticancer effects. The goal of this study was to introduce a novel combinatorial approach for treatment against colon adenocarcinoma cells. To do so, HT29 cells were pretreated with nontoxic auraptene and then hyperthermia was induced. Afterwards, the viability of the cells was assessed, changes induced in the cell cycle were analyzed, and the expression patterns of candidate genes were studied...
February 2018: Biochemistry and Cell Biology, Biochimie et Biologie Cellulaire
https://www.readbyqxmd.com/read/28732810/the-interaction-of-auraptene-and-other-oxyprenylated-phenylpropanoids-with-glucose-transporter-type-4
#16
Salvatore Genovese, Hitoshi Ashida, Yoko Yamashita, Tomoya Nakgano, Masaki Ikeda, Shirasaya Daishi, Francesco Epifano, Vito Alessandro Taddeo, Serena Fiorito
BACKGROUND: Glucose transporter 4 (GLUT4) is firmly established to play a pivotal role in glucose metabolism and in particular in modulating the insulin-stimulated glucose transport in several tissues, such as skeletal muscle and adipose tissue. Stimulation of GLUT4 by insulin results in its translocation to the plasma membrane, activation of several kinases, and finally in a large glucose influx into cells. PURPOSE: In this study we investigated the modulating properties of four biologically active oxyprenylated ferulic acid and umbelliferone derivatives and of their unprenylated parent compounds on GLUT-4 mediated glucose uptake and translocation...
August 15, 2017: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
https://www.readbyqxmd.com/read/28675489/synergy-between-auraptene-ionizing-radiation-and-anticancer-drugs-in-colon-adenocarcinoma-cells
#17
Mahdi Moussavi, Farhang Haddad, Fatemeh B Rassouli, Mehrdad Iranshahi, Shokouhozaman Soleymanifard
Colorectal cancer is a growing health concern with increasing mortality rates, and resistance to anticancer drugs and radiotherapy is a serious drawback in its treatment. Auraptene is a natural prenyloxycoumarin with valuable anticancer effects. The aim of current study was to determine the synergy between auraptene, ionizing radiation, and chemotherapeutic drugs in colon adenocarcinoma cells for the first time. To do so, HT29 cells were treated with combination of auraptene + cisplatin, + doxorubicin, or + vincristine...
September 2017: Phytotherapy Research: PTR
https://www.readbyqxmd.com/read/28605679/a-re-investigation-of-the-phytochemical-composition-of-the-edible-herb-amaranthus-retroflexus-l
#18
Serena Fiorito, Francesco Epifano, Roberta Palmisano, Salvatore Genovese, Vito Alessandro Taddeo
In this paper the presence of selected prenylated and unprenylated phenylpropanoids of nutraceutical value, namely umbelliferone, apigenin, 4'-geranyloxyferulic acid, 7-isopentenyloxycoumarin, auraptene, and umbelliprenin have been determined in all parts of the edible herb Amaranthus retroflexus extracted with different methodologies. Roots were seen to contain the widest variety of unprenylated and prenylated phenylpropanoids both in terms of number of secondary metabolites and their quantitites. Findings described in the present study underline how A...
September 5, 2017: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/28412182/characterization-of-three-small-molecule-inhibitors-of-enterovirus-71-identified-from-screening-of-a-library-of-natural-products
#19
Guiming Li, Qianqian Gao, Shilin Yuan, Lili Wang, Ralf Altmeyer, Ke Lan, Feifei Yin, Gang Zou
Enterovirus 71 (EV-A71) is a major cause of hand, foot, and mouth disease (HFMD). Infection with EV-A71 is more often associated with neurological complications in children and is responsible for the majority of fatalities, but currently there is no approved antiviral therapy for treatment. Here, we identified auraptene, formononetin, and yangonin as effective inhibitors of EV-A71 infection in the low-micromolar range from screening of a natural product library. Among them, formononetin and yangonin selectively inhibited EV-A71 while auraptene could inhibit viruses within the enterovirus species A...
July 2017: Antiviral Research
https://www.readbyqxmd.com/read/28383142/auraptene-induces-apoptosis-via-myeloid-cell-leukemia-1-mediated-activation-of-caspases-in-pc3-and-du145-prostate-cancer-cells
#20
Jae Chul Lee, Eun Ah Shin, Bonglee Kim, Bo-Im Kim, Mahsa Chitsazian-Yazdi, Mehrdad Iranshahi, Sung-Hoon Kim
Although auraptene, a prenyloxy coumarin from Citrus species, was known to have anti-oxidant, anti-bacterial, antiinflammatory, and anti-tumor activities, the underlying anti-tumor mechanism of auraptene in prostate cancers is not fully understood to date. Thus, in the present study, we have investigated the anti-tumor mechanism of auraptene mainly in PC3 and DU145 prostate cancer cells, because auraptene suppressed the viability of androgen-independent PC3 and DU145 prostate cancer cells better than androgen-sensitive LNCaP cells...
June 2017: Phytotherapy Research: PTR
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