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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-hydroxyl-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxy-phenyl)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...
April 4, 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...
March 10, 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
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
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