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Vito Alessandro Taddeo, Francesco Epifano, Francesca Preziuso, Serena Fiorito, Nicolas Caron, Arnaud Rives, Philippe de Medina, Marc Poirot, Sandrine Silvente-Poirot, Salvatore Genovese
Umbelliprenin has recently been shown to have great potential as a skin whitening agent. Wishing to investigate the same effect in plant species known to biosynthesize this coumarin, three plants belonging to the Apiaceae family, namely Anethum graveolens L. (dill), Pimpinella anisum L. (anise), and Ferulago campestris (Besser) Grecescu (field ferula) were screened by HPLC analysis for their respective content of umbelliprenin in extracts obtained with different solvent mixtures and by maceration and ultrasound-assisted processes...
January 30, 2019: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Serena Fiorito, Francesca Preziuso, Francesco Epifano, Luca Scotti, Tonino Bucciarelli, Vito Alessandro Taddeo, Salvatore Genovese
Spinach leaves, goji berries and quinoa seeds are claimed to have a great nutraceutical potential due to their high content of compounds providing benefits for human health, such as amino acids, polyunsaturated fatty acids, carotenoids, betaine, vitamins, fibre, minerals and polyphenols. Samples of these plants were extracted with different solvent mixtures (e.g. EtOH, H2 O/EtOH 3:7 and H2 O/EtOH 7:3) and extractions were accomplished using a microwave apparatus. Subsequent UHPLC analysis and photodiode array detection were employed for the quantification of biologically active compounds like 7-isopentenyloxycoumarin, auraptene, umbelliprenin, boropinic acid and 4'-geranyloxyferulic acid...
March 15, 2019: Food Chemistry
Mohamad Naderi Alizadeh, Mohsen Rashidi, Ahad Muhammadnejad, Taraneh Moeini Zanjani, Seyed Ali Ziai
Umbelliprenin is a sesquiterpene coumarin with vitro anti-carcinogenic activities. The aim of this study was to investigate the antitumor effects of umbelliprenin in animal models of colorectal cancer. The cytotoxic effects of umbelliprenin were explored on CT26 and L929by MTT assay. In this study, colorectal tumors developed in mice by intradermal injection of CT26 cell line. Tumor size, serum levels of IFN-γ and IL-4 by ELISA, and Ki-67, MMP2, MMP9, VEGF and E-cadherin markers by IHC method were evaluated...
2018: Iranian Journal of Pharmaceutical Research: IJPR
Mohsen Rashidi, Ahad Khalilnezhad, Davar Amani, Hamidreza Jamshidi, Ahad Muhammadnejad, Ali Bazi, Seyed Ali Ziai
Umbelliprenin (UMB) has shown various pharmacological properties in vitro. We investigated the antineoplastic and immunostimulatory effects of UMB in 4T1 mammary-tumor-bearing mice. Two-hundred microliter of UMB (12.5 mg/ml) was intraperitoneally administrated to healthy and tumor-bearing female Balb/c mice for a period of 18 days. Data was analyzed using GraphPad Prism 5 software for Windows (version 5, La Jolla, CA). UMB caused a significant decrease in tumor size (P < 0.01). Serum interferon gamma (IFNγ) was augmented in both healthy and tumor-bearing animals (P < 0...
November 2018: Journal of Cellular Physiology
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
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
Salvatore Genovese, Vito Alessandro Taddeo, Francesco Epifano, Serena Fiorito, Cécile Bize, Arnaud Rives, Philippe de Medina
Umbelliprenin is a secondary plant metabolite that displays promising chemopreventive, anti-inflammatory, and antigenotoxic properties. It possesses potential for applications to human welfare notably to prevent the emergence of cancer. For this purpose, stability studies are needed to define proper storage conditions and adapted formulations for this drug candidate. The identification of degradative products is a major concern for the preclinical development of umbelliprenin, providing also interesting information related to potential original phytochemicals formed in plants exposed to stressors...
September 22, 2017: Journal of Natural Products
Narges Khaghanzadeh, Afshin Samiei, Zahra Mojtahedi, Mohammad Ramezani, Massood Hosseinzadeh, Abbas Ghaderi
OBJECTIVES: Umbelliprenin is a prenyloxy-coumarin with pharmacologically polyvalent activity. Several studies have shown Several studies have been shown its anti-inflammatory, anti-tumor, antioxidant, and antigenotoxic activities. However, the exact mechanism of action of this compound on the immune response has not yet been shown. Here, we investigated umbelliprenin effects on the predominance of Th1 and Th2 responses in normal C57/BL6 mice. MATERIALS AND METHODS: Umbelliprenin (2...
July 2017: Iranian Journal of Basic Medical Sciences
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
Omid Gholami
No abstract text is available yet for this article.
April 2017: Dose-response: a Publication of International Hormesis Society
Narges Khaghanzadeh, Kazuyuki Nakamura, Yasuhiro Kuramitsu, Abbas Ghaderi, Zahra Mojtahedi
Umbelliprenin (Umb), a natural coumarin, has demonstrated anti-tumor activities, both in vitro and particularly in vivo, in several types of cancer, including lung cancer. The present study aimed to identify molecular targets of Umb using a high-throughput approach. Lung cancer cell lines, QU-DB (large-cell lung carcinoma) and A549 (adenocarcinoma), were treated with Umb. Differentially-expressed proteins were identified using two-dimensional electrophoresis coupled to mass spectrometry. In the QU-DB cells, differential expression of proteins, including downregulation of the tumorigenic protein heat shock protein 90 kDa and upregulation of the potential anti-tumor proteins Nipsnap1 and glycine-tRNA ligase (GRS), suggested that Umb is a strong anti-tumor compound...
December 2016: Oncology Letters
Vito Alessandro Taddeo, Salvatore Genovese, Philippe de Medina, Roberta Palmisano, Francesco Epifano, Serena Fiorito
An analytical strategy based on different extraction methodologies and HPLC with spectrophotometric (UV-vis) detection has been developed to investigate the presence of and to quantitate biologically active selected unprenylated and O-prenylated phenylpropanoids, namely umbelliferone, 4'-geranyloxyferulic acid, 7-isopentenyloxycoumarin, auraptene, and umbelliprenin in dill (Anethum graveolens L.), anise (Pimpinella anisum L.), and wild celery (Angelica archangelica L.). Absolute ethanol or 7:3 water/ethanol mixtures were seen to be the most powerful extraction solvents to perform "classic" maceration or ultrasound-assisted one in terms of yields in secondary metabolites...
February 5, 2017: Journal of Pharmaceutical and Biomedical Analysis
Mohsen Rashidi, Seyed Ali Ziai, Taraneh Moini Zanjani, Ahad Khalilnezhad, Hamidreza Jamshidi, Davar Amani
BACKGROUND: Resistance to chemotherapy is a growing concern, thus natural anticancer agents are drawing the attention of many scientists and clinicians. One natural anticancer agent, umbelliprenin, is a coumarin produced by many species of Ferula. OBJECTIVES: We aimed to examine the inhibitory effect of umbelliprenin on human and mouse bone marrow-derived stem cells (BMDSCs), peripheral blood mononuclear cells (PBMCs), and different cancer cell lines. MATERIALS AND METHODS: In this in vitro experimental study, the HT29, CT26, MCF-7, 4T1, A172, and GL26 cancer cells and human and mouse BMDSCs and PBMCs were cultured in RPMI-1640 medium supplemented with 10% fetal bovine serum (FBS), incubated at 37°C for 24 hours in a 5% CO2 atmosphere, and then were treated with different concentrations of umbelliprenin dissolved in dimethyl sulfoxide (DMSO) (3, 6, 12, 25, 50, 100, and 200 µg/mL) for 24, 48, and 72 hours at 37°C...
July 2016: Iranian Red Crescent Medical Journal
Mohsen Rashidi, Alireza Ahmadzadeh, Seyed Ali Ziai, Mahsa Narenji, Hamidreza Jamshidi
Cytotoxicity of umbelliprenin has been found in various cancer cell lines such as, prostate, breast, CLL, and skin. Encapsulating chemotherapeutic agents with nanoliposomes have been resulted in improved cytotoxicity effects than their free forms. However, whether nanoliposomal form of umbelliprenin could have higher cytotoxic effect than free umbelliprenin is not clarified yet. After synthesizing umbelliprenin, different concentrations (3, 6, 12, 25, 50, 100, 200 μg/ml) applied on the mouse mammary carcinoma cell line (4T1) for 24, 48, and 72 h at 37°C...
January 2017: In Vitro Cellular & Developmental Biology. Animal
Teijo Yrjönen, Manu Eeva, Tiina J Kauppila, Olli Martiskainen, Jari Summanen, Pia Vuorela, Heikki Vuorela
The coumarin composition of Peucedanum palustre (L.) Moench populations growing in Finland was investigated. A total of 132 flowering P. palustre specimens from 43 locations in southern and central Finland were collected, divided into root, stem, leaf, and umbel samples, and analyzed by HPLC. HPLC coupled to high-resolution mass spectrometry was used to aid the identification of coumarins. A total of 13 coumarin-structured compounds were quantitatively analyzed from the samples. The coumarin profile of root samples was found to differ from the aerial plant parts...
June 2016: Chemistry & Biodiversity
Seyed Hadi Mousavi, Atiyeh-Sadat Davari, Mehrdad Iranshahi, Sarvenaz Sabouri-Rad, Zahra Tayarani Najaran
OBJECTIVE: 7-prenyloxycoumarins are a group of secondary metabolites that are found mainly in plants belonging to the Rutaceae and Umbelliferae families. This study was designed to evaluate and compare the cytotoxic and apoptotic activity of 7-prenyloxycoumarin compounds and herniarin on MCF-7, a breast carcinoma cell line. MATERIALS AND METHODS: Cells were cultured in RPMI medium and incubated with different concentrations of auraptene, herniarin, umbelliferone, and umbelliprenin...
November 2015: Avicenna Journal of Phytomedicine
Shahrzad Zamani Taghizadeh Rabe, Mehrdad Iranshahi, Mahmoud Mahmoudi
Ferula species (Apiaceae) are considered important medicinal plants. The present in vitro study sought to investigate the immunomodulatory and anti-inflammatory properties of terpenoid coumarins isolated from Ferula szowitsiana on immune cells isolated from naïve mice and to elucidate possible underlying mechanisms of action. With splenocytes, effects of the agents on PHA-induced proliferation and interleukin (IL)-4 and interferon (IFN)-γ release were assessed. With peritoneal macrophages, anti-inflammatory potentials were evaluated in lipopolysaccharide (LPS)/IFNγ-stimulated cells via measures of changes in nitric oxide (NO) and PGE(2) secretion...
2016: Journal of Immunotoxicology
Jamal Kasaian, Fatemeh Mosaffa, Javad Behravan, Milena Masullo, Sonia Piacente, Morteza Ghandadi, Mehrdad Iranshahi
In the present study, fifteen sesquiterpene coumarins were isolated and purified from different Ferula species, and were tested for their MDR reversal properties. Enhancement of doxorubicin cytotoxicity in MCF-7/Adr cells (doxorubicin resistant derivatives of MCF-7 cells overexpressing P-gp), when combined with very non-toxic concentrations of the sesquiterpene coumarins (50 μM) including umbelliprenin, farnesiferol B, farnesiferol C and lehmferin, proved significant MDR reversal activity of these coumarins...
June 2015: Fitoterapia
Omid Gholami, Mahmood Jeddi-Tehrani, Mehrdad Iranshahi, Amir Hassan Zarnani, Seyed Ali Ziai
Chronic lymphocytic leukaemia (CLL) is the most common B-cell malignancy in the western world and exists as subtypes with very different clinical courses. Myeloid cell leukemia 1 (Mcl-1) is one member of Bcl-2 family proteins that has been shown to be expressed in various tissues and malignant cells, including CLL, where its expression is significantly associated with a failure to achieve complete remission following cytotoxic therapy. Induction of apoptosis by prenylated coumarin, umbelliprenin, in Jurkat cells was previously shown...
2014: Iranian Journal of Pharmaceutical Research: IJPR
Abolfazl Shakeri, Milad Iranshahy, Mehrdad Iranshahi
7-Prenyloxycoumarins are a group of secondary metabolites found mainly in plants belonging to the families Rutaceae and Apiaceae. Auraptene, umbelliprenin (UM), and 7-isopentenyloxycoumarin are some examples of prenylated coumarins. UM occurs in various edible plant species including celery, coriander, angelica, lemon, and particularly, Ferula species. Although UM was isolated more than 50 years ago, its biological activities have been studied since the last two decades. Besides anticancer activities, biological activities including anti-inflammatory, antioxidant, and antileishmanial activities have been reported from this natural compound...
2014: Journal of Asian Natural Products Research
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