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Ri Ryu, Tae-Sook Jeong, Ye Jin Kim, Ji-Young Choi, Su-Jung Cho, Eun-Young Kwon, Un Ju Jung, Hyeon-Seon Ji, Dong-Ha Shin, Myung-Sook Choi
Pterocarpans are known to have antifungal and anti-inflammatory properties. However, little is known about the changes in transcriptional profiles in response to a pterocarpan-high soybean leaf extract (PT). Therefore, this study investigated the effects of PT on blood glucose and lipid levels, as well as on the inflammation-related gene expression based on a peripheral blood mononuclear cells (PBMCs) mRNA sequencing analysis in Korean overweight and obese subjects with mild metabolic syndrome. The participants were randomly assigned to two groups and were administered either placebo (starch, 3 g/day) or PT (2 g/day) for 12 weeks...
November 18, 2016: Nutrients
Mary Snow Setzer, Javad Sharifi-Rad, William N Setzer
Recently, the emergence and spread of pathogenic bacterial resistance to many antibiotics (multidrug-resistant strains) have been increasing throughout the world. This phenomenon is of great concern and there is a need to find alternative chemotherapeutic agents to combat these antibiotic-resistant microorganisms. Higher plants may serve as a resource for new antimicrobials to replace or augment current therapeutic options. In this work, we have carried out a molecular docking study of a total of 561 antibacterial phytochemicals listed in the Dictionary of Natural Products, including 77 alkaloids (17 indole alkaloids, 27 isoquinoline alkaloids, 4 steroidal alkaloids, and 28 miscellaneous alkaloids), 99 terpenoids (5 monoterpenoids, 31 sesquiterpenoids, 52 diterpenoids, and 11 triterpenoids), 309 polyphenolics (87 flavonoids, 25 chalcones, 41 isoflavonoids, 5 neoflavonoids, 12 pterocarpans, 10 chromones, 7 condensed tannins, 11 coumarins, 30 stilbenoids, 2 lignans, 5 phenylpropanoids, 13 xanthones, 5 hydrolyzable tannins, and 56 miscellaneous phenolics), 30 quinones, and 46 miscellaneous phytochemicals, with six bacterial protein targets (peptide deformylase, DNA gyrase/topoisomerase IV, UDP-galactose mutase, protein tyrosine phosphatase, cytochrome P450 CYP121, and NAD⁺-dependent DNA ligase)...
September 12, 2016: Antibiotics
Xinzhou Yang, Mi Huang, Jinyan Cai, Dan Lv, Jingnan Lv, Sijian Zheng, Xinhua Ma, Ping Zhao, Qiang Wang
An EtOAc fraction from the roots of Caragana tangutica Maxim. (CTEA) displayed promising anti-hepatocellular carcinoma (HCC) activity during screening of a traditional Chinese ethnic herb library against HepG2 and Hep3B cell lines. HPLC-based activity profiling of CTEA by combination of MS-guided large-scale semi-preparative HPLC and NMR methods led to the identification of a new pterocarpan glycoside, (-)-maackiain 3-O-6'-O-methyl malonyl-β-d-glucopyranoside (1), together with three known pterocarpan glycosides, (-)-maackiain 3-O-β-d-glucopyranoside (2), 3-O-6'-O-acrylyl-β-d-galactopyranoside (3), and (-)-maackiain 3-O-6'-O-acetyl-β-d-glucopyranoside (4)...
September 14, 2016: Natural Product Research
Wei Peng, Liang Wang, Xu-Hui Qiu, Yi-Ping Jiang, Lan Pan, Xiao-Guang Jia, Lu-Ping Qin, Cheng-Jian Zheng
A new pterocarpan derivative, pruinosanone D (1), a new isoflavonoid, pruinosanone E (2), and a new chalcone, pruinosanone F (3), were isolated from Caragana pruinosa roots, along with four known analogues (4-7), identified as 2,4-dihydroxy-3'-methoxy-4'-ethoxychalcone, 7,4-dihydroxyflavanone, butin and scutellaprostin C, respectively. Their structures were elucidated by detailed analyses of NMR, IR, and MS data. The ability of the isolated compounds to prevent nitric oxide (NO) production by LPS-stimulated RAW 264...
October 2016: Fitoterapia
Hyun Woo Lee, Hyung Won Ryu, Myung-Gyun Kang, Daeui Park, Sei-Ryang Oh, Hoon Kim
Monoamine oxidase (MAO) catalyzes the oxidation of monoamines and its two isoforms, MAO-A and MAO-B, break down neurotransmitter amines. Of the compounds isolated from the roots of Sophora flavescens, (-)-maackiain (4), a pterocarpan, was found to potently and selectively inhibit human MAO-B, with an IC50 of 0.68μM, and to have a selectivity index of 126.2 for MAO-B. As compared with other herbal natural products, the IC50 value of 4 for MAO-B is one of the lowest reported to date. Genistein (1) highly, effectively and non-selectively inhibited MAO-A and MAO-B with IC50 values of 3...
October 1, 2016: Bioorganic & Medicinal Chemistry Letters
Lauana Greicy Tonon Lemos, Gabriela Nestal de Moraes, Deborah Delbue, Flavia da Cunha Vasconcelos, Paula Sabbo Bernardo, Eric W-F Lam, Camilla Djenne Buarque, Paulo Ribeiro Costa, Raquel Ciuvalschi Maia
UNLABELLED: Multidrug resistance is the major obstacle for successful treatment of breast cancer, prompting the investigation of novel anticancer compounds. PURPOSE: In this study, we tested whether LQB-223, an 11a-N-Tosyl-5-deoxi-pterocarpan newly synthesized compound, could be effective toward breast cancer cells. METHODS: Human breast cell lines MCF-7, MDA-MB-231, HB4a and MCF-7 Dox(R) were used as models for this study. Cell culture, MTT and clonogenic assay, flow cytometry and Western blotting were performed...
October 2016: Journal of Cancer Research and Clinical Oncology
Mohamed A Farag, Hattem Mekky, Sawsan El-Masry
An MS-based metabolomic approach was used to profile the secondary metabolite of the ornamental plant Erythrina lysistemon via ultra-performance liquid chromatography coupled to photodiode array detection and high resolution q-TOF mass spectrometry (UPLC-PDA-MS). Cultures maintained the capacity to produce E. lysistemon flavonoid subclasses with pterocarpans amounting for the most abundant ones suggesting that it could provide a resource of such flavonoid subclass. In contrast, alkaloids, major constituents of Erythrina genus, were detected at trace levels in suspension cultures...
September 2016: Journal of Advanced Research
Pravin Mahajan, Rajaraman Gnana Oli, Sanjay M Jachak, Sandip B Bharate, Bhabatosh Chaudhuri
OBJECTIVES: This study aimed to investigate the anticancer potential of indigocarpan (1), a pterocarpan isolated from Indigofera aspalathoides, a plant found in India which has been used in Ayurveda for centuries for the treatment of oedematous tumours. METHODS: The antiproliferative activity in a panel of four human cancer cell lines was studied. The mechanism of its antiproliferative activity in human colorectal adenocarcinoma LS174T cells was investigated in detail...
October 2016: Journal of Pharmacy and Pharmacology
Orsolya Roza, Ana Martins, Judit Hohmann, Wan-Chun Lai, Jacobus Eloff, Fang-Rong Chang, Dezső Csupor
The present paper reports the chemical analysis of the methanolic extracts of fermented and non-fermented Cyclopia genistoides herbs and an investigation of the xanthine oxidase inhibitory activity of the isolated constituents. Chemical analysis of the leaves and stems of C. genistoides yielded the isolation and identification of two benzophenone glucosides, iriflophenone 2-O-β-glucopyranoside (1) and iriflophenone 3-C-β-glucopyranoside (2), two pterocarpans, (6aR,11aR)-(-)-2-methoxymaackiain (5) and (6aR,11aR)-(-)-maackiain (6), along with the flavanones liquiritigenin (9) and hesperetin (10), the flavone diosmetin (11), the isoflavones afrormosin (7) and formononetin (8), piceol (3), and 4-hydroxybenzaldehid (4)...
September 2016: Planta Medica
Jyoti Kureel, Aijaz A John, Ashutosh Raghuvanshi, Pallavi Awasthi, Atul Goel, Divya Singh
Osteogenic activity was identified in medicarpin (Med), a natural pterocarpan. Further, it was decided to study the differentially regulated protein expression during osteoblast differentiation in the presence of Med. Using 2D proteomic approach, we found that Med treatment to osteoblasts significantly downregulated GRP78, an ER chaperone with anti-apoptotic properties which also controls the activation of unfolded protein response signaling, a pro-survival strategy for normal ER functioning. However, severe stress leads to triggering of apoptotic responses and signaling switches to pro-apoptotic...
July 2016: Molecular and Cellular Biochemistry
Jennifer B Chang, Majella E Lane, Min Yang, Michael Heinrich
In order to understand the chemical relationship between a traditional hexa-herbal Chinese medicine formula and botanical drugs it is derived from, an analytical platform comprising liquid chromatography coupled with triple quadrupole mass spectrometry and data mining was developed to separate and identify key chemical components. The hexa-herbal formula comprises the rootstock of Scutellaria baicalensis, Rheum tanguticum, Sophora flavescens, the root bark of Dictamnus dasycarpus, the bark of Phellodendron chinense, and the fruit of Kochia scoparia...
July 2016: Planta Medica
Elvira E Shults, Makhmut M Shakirov, Mikhail A Pokrovsky, Tatijana N Petrova, Andrey G Pokrovsky, Petr G Gorovoy
Twenty-one phenolic compounds (1-21) including dihydrocinnamic acid, isoflavonoids, flavonoids, coumestans, pterocarpans, chalcones, isoflavan and isoflaven, were isolated from the roots of Glycyrrhiza pallidiflora Maxim. Phloretinic acid (1), chrysin (6), 9-methoxycoumestan (8), isoglycyrol (9), 6″-O-acetylanonin (19) and 6″-O-acetylwistin (21) were isolated from G. pallidiflora for the first time. Isoflavonoid acetylglycosides 19, 21 might be artefacts that could be produced during the EtOAc fractionation process of whole extract...
May 22, 2016: Natural Product Research
Eduardo J Salustiano, Matheus L Dumas, Gabriel G Silva-Santos, Chaquip D Netto, Paulo R R Costa, Vivian M Rumjanek
Cancer is a malignancy of worldwide prevalence, and although new therapeutic strategies are under investigation, patients still resort to reductive or palliative chemotherapy. Side effects are a great concern, since treatment can render patients susceptible to infections or secondary cancers. Thus, design of safer chemotherapeutic drugs must consider the risk of immunotoxicity. Pterocarpans are natural isoflavones that possess immunomodulatory and antineoplastic properties. Ubiquitous in nature, quinones are present in chemotherapeutic drugs such as doxorubicin and mitoxantrone...
October 2016: Investigational New Drugs
Shih-Chang Chien, Hsi-Lin Chiu, Wei-Yi Cheng, Yong-Han Hong, Sheng-Yang Wang, Jyh-Horng Wu, Chun-Ching Shih, Jung-Chun Liao, Yueh-Hsiung Kuo
Six compounds were isolated from Derris laxiflora Benth., including two new pterocarpans, 7,6'-dihydroxy-3'-methoxypterocarpan (1) and derrispisatin (2), as well as four known ones, lespedezol D, (3), secundiflorol 1 (4), 6a-hydroxymaackiain (5) and pisatin (6). The structures of these compounds were determined by analysis of their spectroscopic data.
January 2016: Natural Product Communications
Nóra Gampe, András Darcsi, Szilvia Lohner, Szabolcs Béni, László Kursinszki
Restharrow root has been used in traditional medicine for thousands of years; however, the active ingredients responsible for the diuretic effect are still unknown. Previous studies have proved that the root extract contains isoflavonoids, however only few derivatives were identified, mostly relying on retention times or UV data. The aim of our work was to perform a detailed structural characterization of the complete isoflavonoid profile in the aqueous-methanolic extract of Ononis spinosa root by high-performance liquid chromatography coupled with electrospray ionization accurate-mass quadrupole time-of-flight and tandem mass spectrometry in positive ionization mode (HPLC-ESI-QTOF-MS, HPLC-ESI-MS/MS) and nuclear magnetic resonance spectroscopy (NMR)...
May 10, 2016: Journal of Pharmaceutical and Biomedical Analysis
Hee-Sung Chae, Hunseung Yoo, Young Hee Choi, Won Jun Choi, Young-Won Chin
Maackiapterocarpan B, one of the pterocarpan analogs found in Sophora tonkinensis, is known to display pharmacological activities. However, the anti-inflammatory effects of maackiapterocarpan B and its molecular mechanism have yet to be clearly elucidated. In the present study, the effects of maackiapterocarpan B on macrophage-mediated inflammation in vitro were assessed. Maackiapterocarpan B inhibited the production of nitric oxide, the expression of tumor necrosis factor α, colony stimulating factor 2, interleukin-1β and interleukin-6, and the activation of nuclear factor-κB and mitogen-activated protein kinases in lipopolysaccharide-stimulated macrophages...
2016: Biological & Pharmaceutical Bulletin
Luciano Pecetti, Mariella Mella, Aldo Tava
This study assessed the variation in herbage protein and fiber content as well as concentration of furocoumarins, plicatin B, (E)-werneria chromene, and pterocarpans of pitch trefoil (Bituminaria bituminosa) germplasm sampled in situ in both summer and autumn in Elba Island, Italy. Populations were sampled from a range of climatic and edaphic conditions, on light soils with pH > 7.5. Valuable variation occurred for forage quality and chemical composition. The quality features, relevant for a possible forage utilization of the species, were promising for the leaves, which represented about two-thirds of the total aerial biomass in early summer and the whole green regrowth in autumn...
January 13, 2016: Journal of Agricultural and Food Chemistry
Ruwida M K Omar, John Igoli, Alexander I Gray, Godwin Unekwuojo Ebiloma, Carol Clements, James Fearnley, Ru Angeli Edrada Ebel, Tong Zhang, Harry P De Koning, David G Watson
INTRODUCTION: A previous study showed the unique character of Nigerian red propolis from Rivers State, Nigeria (RSN), with regards to chemical composition and activity against Trypanosoma brucei in comparison with other African propolis. OBJECTIVE: To carry out fractionation and biological testing of Nigerian propolis in order to isolate compounds with anti-trypanosomal activity. To compare the composition of the RSN propolis with the composition of Brazilian red propolis...
March 2016: Phytochemical Analysis: PCA
Manisha Dixit, Ashutosh Raghuvanshi, Chandra Prakash Gupta, Jyoti Kureel, Mohd Nizam Mansoori, Priyanka Shukla, Aijaz A John, Kavita Singh, Dipak Purohit, Pallavi Awasthi, Divya Singh, Atul Goel
We evaluated the bone regeneration and healing effect of Medicarpin (med) in cortical bone defect model that heals by intramembranous ossification. For the study, female Sprague-Dawley rats were ovariectomized and rendered osteopenic. A drill hole injury was generated in mid femoral bones of all the animals. Med treatment was commenced the day after and continued for 15 days. PTH was taken as a reference standard. Fifteen days post-treatment, animals were sacrificed. Bones were collected for histomorphometry studies at the injury site by micro-computed tomography (μCT) and confocal microscopy...
2015: PloS One
Milou G M van de Schans, Jean-Paul Vincken, Pieter de Waard, Astrid R M Hamers, Toine F H Bovee, Harry Gruppen
Seven prenylated 6a-hydroxy-pterocapans and five prenylated 6a,11a-pterocarpenes with different kinds of prenylation were purified from an ethanolic extract of fungus-treated soybean sprouts. The activity of these compounds toward both human estrogen receptors (hERα and hERβ) was determined in a yeast bioassay and the activity toward hERα was additionally tested in an U2-OS based hERα CALUX bioassay. In the yeast bioassay, compounds with chain prenylation showed in general an agonistic mode of action toward hERα, whereas furan and pyran prenylation led to an antagonistic mode of action...
February 2016: Journal of Steroid Biochemistry and Molecular Biology
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