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Erika Tayse da Cruz Almeida, Maria Cristina Delgado da Silva, José Marcos Dos Santos Oliveira, Regianne Umeko Kamiya, Rodolfo Elleson Dos Santos Arruda, Danilo Abreu Vieira, Valdemir da Costa Silva, Pierre Barnabé Escodro, Irinaldo Diniz Basílio-Júnior, Ticiano Gomes do Nascimento
The aim of this study was to characterize tinctures and microcapsules loaded with an ethanol extract of red propolis through chemical, physicochemical and microbiological assays in order to establish quality control tools for nutraceutical preparations of red propolis. The markers (isoflavonoids, chalcones, pterocarpans, flavones, phenolic acids, terpenes and guttiferones) present in the tinctures A and B were identified and confirmed using LC/ESI/FTMS/Orbitrap. Four compositions (A, B, C and D) were prepared to contain B tincture of the red propolis with some pharmaceutical excipients and submitted to two drying processes, i...
October 2017: Journal of Pharmaceutical Analysis
Khan Mohammad Imran, Dahyeon Yoon, Tae-Jin Lee, Yong-Sik Kim
Natural pterocarpan Medicarpin (Med) has been shown to have various beneficial biological roles, including inhibition of osteoclastogenesis, stimulation of bone regeneration and induction of apoptosis. However, the effect of the Med on lipolysis in adipocytes has not been reported. Here, we show the effect of Med on lipolysis in different mouse adipocytes and elucidate the underlying mechanism. We observed that Med treatment promoted release of glycerol in the media. Differentiated mouse brown adipose tissue cells were treated with Med...
January 22, 2018: BMB Reports
Dan Tang, Ying-Bin Shen, Zhi-Hua Wang, Bao He, You-Hua Xu, Hong Nie, Quan Zhu
Isoflavonoids including isoflavones, isoflavans and pterocarpans, the principal components in Astragalus membranaceus, have a great deal of versatile health-promoting benefits. In this work, as a continuation of our searching for bioactive constituents from A. membranaceus, a fast UHPLC-DAD-MSn method was firstly used to analyze the isoflavonoids profile of A. membranaceus roots extract. Twelve diverse isoflavonoids with subclass of isoflavones, isoflavans and pterocarpans occurred in glycoside/aglycone pairs forms were tentatively characterized, of them eight major isoflavonoids were finally isolated guided and simultaneously quantified by the established fast UHPLC method...
November 1, 2017: Journal of Agricultural and Food Chemistry
Khan Mohammad Imran, Dahyeon Yoon, Yong-Sik Kim
Obesity poses a substantial threat of a worldwide epidemic and requires better understanding of adipose-tissue biology as well as necessitates research into the etiology and therapeutic interventions. In this study, Medicarpin (Med), a natural pterocarpan, was selected (by screening) as a small-molecule inducer of adipocyte differentiation among 854 candidates by using C3H10T1/2 mesenchymal stem cell; a cellular model of adipogenesis. Med induced the expression of brown-adipocyte commitment marker Bmp7 as well as the early regulators of brown fat fate Pparγ, Prdm16, and Pgc-1α during differentiation of C3H10T1/2 mesenchymal stem cells...
October 24, 2017: BioFactors
Masanori Morimoto, Charles L Cantrell, Shabana Khan, Babu L Tekwani, Stephen O Duke
Thirty-seven phytophenolics and their synthetic analogues were evaluated for activity against two protozoal pathogens, Leishmania donovani and Plasmodium falciparum (D6 and W2 clones), respectively. 4,6-Dimethoxyaurone demonstrated the highest activity with IC50 values of 13.2 and 16.9 μm against L. donovani and P. falciparum (W2 clone), respectively, without undesired cytotoxicity against VERO cells. The moiety having two benzene rings was critical to maintain the antiprotozoal activities based on the observation that both coumaranones and chromones were inactive while other test compounds, including coumarans and aurones, remained active...
December 2017: Chemistry & Biodiversity
Carla Araya-Cloutier, Jean-Paul Vincken, Roan van Ederen, Heidy M W den Besten, Harry Gruppen
Prenylated phenolics from the Fabaceae are promising lead compounds for new antibacterials. Pools enriched in prenylated phenolics were made from lupine, peanut and soybean seedlings. One pool was rich in chain prenylated isoflavones (cIsf), one in chain prenylated stilbenoids (cSti), one in chain prenylated (cPta) and one in ring-closed prenylated pterocarpans (rPta), as characterized by RP-UHPLC-UV-MS. Antibacterial activity of the pools and membrane permeabilization was investigated. Pools showed high antibacterial activity against Listeria monocytogenes: cIsf pool had a minimum inhibitory concentration of 10µg/ml prenylated compounds, followed by cPta pool (25µg/ml) and cSti pool (35µg/ml)...
February 1, 2018: Food Chemistry
Khaled A Selim, Hend Abdelrasoul, Mohamed Aboelmagd, Ahmed M Tawila
Reactive oxygen species (ROS) are common products of mitochondrial oxidative phosphorylation, xenobiotics metabolism and are generated in response to several environmental stress conditions. Some of them play important biochemical roles in cellular signal transduction and gene transcription. On the other hand, ROS are known to be involved in a wide range of human diseases, including cancer. The excessive production of such ROS together with disruption of homeostasis detoxifying mechanisms can mediate a series of cellular oxidative stresses...
April 26, 2017: Diseases (Basel)
L Pistelli, V Ulivieri, S Giovanelli, L Avio, M Giovannetti, L Pistelli
Secondary metabolites may be affected by arbuscular mycorrhizal fungi (AMF), which are beneficial symbionts associated with the roots of most plant species. Bituminaria bituminosa (L.) C.H.Stirt is known as a source of several phytochemicals and therefore used in folk medicine as a vulnerary, cicatrising, disinfectant agent. Characteristic metabolites found in B. bituminosa are furanocoumarins and pterocarpans, which are used in cosmetics and as chemotherapeutic agents. Here we address the question whether AMF inoculation might affect positively the synthesis of these phytochemicals...
November 2017: Plant Biology
Zhong-Lin Sun, Jian-Ming He, Jiang-Er Lan, Qing Mu
INTRODUCTION: High-speed counter-current chromatography (HSCCC) is an efficient and non-absorption separation technique, but limitations still exist in simultaneous isolation of complex structures of natural products. Moreover, particular methods are various for different kinds of natural products. OBJECTIVE: A novel HSCCC strategy combined with an online storage recycling elution (OSR-CCC) technique was developed for the quick separation of naturally occurring dihydroflavonoids from the extract of the herb Sophora alopecuroides L...
June 6, 2017: Phytochemical Analysis: PCA
Kai Uchida, Tomoyoshi Akashi, Toshio Aoki
Pterocarpan forms the basic structure of leguminous phytoalexins, and most of the isoflavonoid pathway genes encoding the enzymes responsible for its biosynthesis have been identified. However, the last step of pterocarpan biosynthesis is a ring closure reaction, and the enzyme that catalyzes this step, 2'-hydroxyisoflavanol 4,2'-dehydratase or pterocarpan synthase (PTS), remains as an unidentified 'missing link'. This last ring formation is assumed to be the key step in determining the stereochemistry of pterocarpans, which plays a role in their antimicrobial activity...
February 1, 2017: Plant & Cell Physiology
Jutatip Boonsombat, Vilailak Prachyawarakorn, Acharavadee Pansanit, Chulabhorn Mahidol, Somsak Ruchirawat, Sanit Thongnest
Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (2), eight pterocarpans (3 - 10), and eleven isoflavonoids (11 - 21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D- and 2D-NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities...
July 2017: Chemistry & Biodiversity
R V Bandeira Reidel, S Giovanelli, A Pipitone, P Minissale, L Pistelli
The first phytochemical investigation of the aerial parts of Bituminaria basaltica, an endemic species from the Aeolian Islands, led to the isolation and identification of eight compounds including plicatin B (3), two furanocoumarins: angelicin (1), psoralen (2), three pterocarpans: erybraedin C (4), 3,9-dihydroxy-4-isoprenyl-pterocarpan (5), bitucarpin A (8) and two flavonoid glycosides: isoorientin (6), daidzin (7). Their structures were elucidated by spectroscospic techniques and compared with data reported in the literature...
March 28, 2017: Natural Product Research
Ashutosh Raghuvanshi, Amit Kumar, Abdul M Tyagi, Jyoti Kureel, Pallavi Awasthi, Deepak Purohit, Mohd Nizam Mansoori, Priyanka Shukla, Kamini Srivastava, Abnish K Gautam, Ruchi Saxena, Anila Dwivedi, Divya Singh, Atul Goel
A series of new 6H-benzofuro[3, 2-c]chromenes (BFC, pterocarpans) with structure-activity relationships were investigated for their potential use in osteoporosis treatment. One of the BFCs 3-piperidylethoxypterocarpan 20 promotes osteoblast differentiation and mineralization at a dose as low as 1 pM via activation of ER/P38MAPK/BMP-2 pathway. When evaluated for in-vivo osteogenic activity in female Sprague-Dawley rats, BFC 20 increased bone mineral density and new bone formation, compared with control at 1...
June 15, 2017: Molecular and Cellular Endocrinology
Sukanda Sudanich, Suppachai Tiyaworanant, Chavi Yenjai
A new flavonoid, crotakanda (1), and seven known compounds including a flavonoid, four isoflavonoids, a pterocarpan and a cinnamaldehyde were isolated from the stems and roots of Crotalaria bracteata. Their structures were elucidated by a combination of spectroscopic methods. Compound 2 showed cytotoxicity against MCF-7 with an IC50 value of 79.90 μM whereas 2 and 4 exhibited cytotoxicity against the NCI-H187 cell line with IC50 values of 71.57 and 95.47 μM, respectively.
February 13, 2017: Natural Product Research
Daniela Guardado-Félix, Sergio O Serna-Saldivar, Edith O Cuevas-Rodríguez, Daniel A Jacobo-Velázquez, Janet A Gutiérrez-Uribe
Isoflavonoid compositions, phenylalanine ammonia lyase (PAL) activity and antioxidant capacity were evaluated in chickpea (Cicer arietinum L.) sprouts germinated after soaking with different sodium selenite (Na2SeO3) concentrations (0, 1 and 2mg/100g seeds). Chickpea seeds were germinated during four days at 24°C and the isoflavonoid profiles and concentrations evaluated by HPLC-UV daily during four days of germination. Eleven isoflavones and two pterocarpan phytoalexins forms were identified in sprouts, being malonylated formononetin glycoside, formononetin, isoformononetin glycoside and malonylated biochanin A glycoside the major compounds...
July 1, 2017: Food Chemistry
Chelliah Selvam, Brian C Jordan, Sandhya Prakash, Daniel Mutisya, Ramasamy Thilagavathi
Phytoalexins are substances produced by plants that act as potent inhibitors of pathogens. Pterocarpans are biologically active isoflavonoids most commonly found in the family Fabaceae that have the ability to act as phytoalexins. It is made up of a tetracyclic ring system possessing benzofuran-benzopyran. A very great number of pterocarpans have been isolated from natural sources and they are proved to have significant biological activities such as anti-microbial, anti-cancerous, anti-inflammatory and anti-malarial activities...
March 10, 2017: European Journal of Medicinal Chemistry
Stephen S Nyandoro, Joan J E Munissi, Msim Kombo, Clarence A Mgina, Fangfang Pan, Amra Gruhonjic, Paul Fitzpatrick, Yu Lu, Bin Wang, Kari Rissanen, Máté Erdélyi
Prenylated and O-methylflavonoids including one new pterocarpan (1), three new isoflavones (2-4), and nineteen known natural products (5-23) were isolated and identified from the root, stem bark, and leaf extracts of Erythrina schliebenii. The crude extracts and their constituents were evaluated for antitubercular activity against Mycobacterium tuberculosis (H37Rv strain), showing MICs of 32-64 μg mL(-1) and 36.9-101.8 μM, respectively. Evaluation of their toxicity against the aggressive human breast cancer cell line MDA-MB-231 indicated EC50 values of 13...
February 24, 2017: Journal of Natural Products
Marina M Silva, Eduarda O O Nascimento, Edeíldo F Silva, João Xavier de Araújo, Camilla C Santana, Luciano Aparecido M Grillo, Rafaela S de Oliveira, Paulo R R Costa, Camilla D Buarque, Josué Carinhanha C Santos, Isis M Figueiredo
The interaction of small molecules with DNA has been quite important, since this biomolecule is currently the major target for a wide range of drugs in clinical use or advanced clinical research phase. Thus, the present work aimed to assess the interaction process between the bioactive compound 11a-N-tosyl-5-carba-pterocarpan, (LQB-223), that presents antitumor activity, with DNA, employing spectroscopic techniques, electrophoresis, viscosity and theoretical studies. Through UV-vis and molecular fluorescence spectroscopy, it was possible to infer that the preferential quenching mechanism was static, characterized by non-fluorescent supramolecular complex formation between the LQB-223 and DNA...
March 2017: International Journal of Biological Macromolecules
Keisuke Yoneyama, Tomoyoshi Akashi, Toshio Aoki
Soybean (Glycine max) accumulates several prenylated isoflavonoid phytoalexins, collectively referred to as glyceollins. Glyceollins (I, II, III, IV and V) possess modified pterocarpan skeletons with C5 moieties from dimethylallyl diphosphate, and they are commonly produced from (6aS, 11aS)-3,9,6a-trihydroxypterocarpan [(-)-glycinol]. The metabolic fate of (-)-glycinol is determined by the enzymatic introduction of a dimethylallyl group into C-4 or C-2, which is reportedly catalyzed by regiospecific prenyltransferases (PTs)...
December 2016: Plant & Cell Physiology
Flavia Regina Sobreira Corrêa, Fernanda Seabra Schanuel, Nathalia Moura-Nunes, Andréa Monte-Alto-Costa, Julio Beltrame Daleprane
The use of natural products in wound healing has been extensively studied in the context of complementary and alternative medicine. Propolis, a natural product, is a polyphenol-rich resin used for this purpose. This study aimed to investigate the effect of Brazilian Red Propolis Extract (BRPE) on inflammation and wound healing in mice, using a tissue repair model. The BRPE polyphenol content was analyzed by liquid chromatography coupled to mass spectrometry (LC/MS). A full-thickness excision lesion was created, and mice were treated orally with daily doses of vehicle solution (water-alcohol solution containing 2% of ethanol, control group) or 100mg/kg of BRPE (P100 group) during nine consecutive days...
February 2017: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
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