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Yun Zhu, Kayoko Kawaguchi, Ryoiti Kiyama
Mammalian lignans or enterolignans are metabolites of plant lignans, an important category of phytochemicals. Although they are known to be associated with estrogenic activity, cell signaling pathways leading to specific cell functions, and especially the differences among lignans, have not been explored. We examined the estrogenic activity of enterolignans and their precursor plant lignans and cell signaling pathways for some cell functions, cell cycle and chemokine secretion. We used DNA microarray-based gene expression profiling in human breast cancer MCF-7 cells to examine the similarities, as well as the differences, among enterolignans, enterolactone and enterodiol, and their precursors, matairesinol, pinoresinol and sesamin...
2017: PloS One
Labib Noman, Feyza Oke-Altuntas, Amar Zellagui, Ayse Sahin Yaglioglu, Ibrahim Demirtas, Susana M Cardoso, Salah Akkal, Noureddine Gherraf, Salah Rhouati
A new compound (microphybenzimidazole, 7) along with the six known compounds matairesinol (1), prestegane B (2), umbelliferone (3), daphnoretin (4), microphynolide A (5) and microphynolide B (6) were isolated from Thymelaea microphylla. The structures of the pure compounds were elucidated by spectroscopic and mass-spectrometric analyses, including 1D-, 2D-NMR, and HPLC-TOF/MS. Compounds 2 and 4, as well as three fractions (F6, F6-C5, and F6-W42) obtained from a 50% (v:v) CH2Cl2:MeOH extract exhibited a selective activity against rat brain glioma cells (C6)...
January 20, 2017: Natural Product Research
Chang-Ling Hu, Juan Xiong, Peng Xu, Ke-Jun Cheng, Guo-Xun Yang, Jin-Feng Hu
During a further and comprehensive phytochemical investigation on the shed trunk barks of the critically endangered plant Abies beshanzuensis, one new (1) and ten known (2-11) lignans with diverse structures were isolated. On the basis of spectroscopic methods, the new structure was established to be (7S,8R,8'R)-4'-methoxyl-α-conidendrin (1). Among the isolated lignans, (-)-matairesinol (5) and (-)-arctigenin (6) showed significant anti-neuroinflammatory activities by inhibiting the overproduction of nitric oxide in lipopolysaccharide-stimulated murine BV-2 microglial cells, with IC50 values of 11...
October 23, 2016: Natural Product Research
Akira Shiraishi, Jun Murata, Erika Matsumoto, Shin Matsubara, Eiichiro Ono, Honoo Satake
Forsythia spp. are perennial woody plants which are one of the most extensively used medicinal sources of Chinese medicines and functional diets owing to their lignan contents. Lignans have received widespread attention as leading compounds in the development of antitumor drugs and healthy diets for reducing the risks of lifestyle-related diseases. However, the molecular basis of Forsythia has yet to be established. In this study, we have verified de novo deep transcriptome of Forsythia koreana leaf and callus using the Illumina HiSeq 1500 platform...
2016: PloS One
Natalja P Nørskov, Knud Erik Bach Knudsen
Despite the extensive literature describing the biological effects of phenolic compounds from cereals, little is known about their bioaccessibility in the food matrix. This paper describes a validated LC-MS/MS method for the quantification of free and total content (free + bound) of eight plant lignans (matairesinol, hydroxymatairesinol, secoisolariciresinol, lariciresinol, isolariciresinol, syringaresinol, medioresinol, and pinoresinol) and two enterolignans (enterodiol and enterolactone) in cereal-based diets/bread and feces...
November 9, 2016: Journal of Agricultural and Food Chemistry
Qiang Zhang, Hongliang Feng, Bakare Qluwakemi, Jiaqi Wang, Songpo Yao, Guangdong Cheng, Hui Xu, Hongbin Qiu, Liling Zhu, Mingxia Yuan
This updated meta-analysis was performed to clarify the relationship between phytoestrogens and prostate cancer risk. Twenty one case-control and two cohort studies were finally selected for this meta-analysis, totaling 11,346 cases and 140,177 controls. Analytical results showed that daidzein (OR = 0.85; 95% CI: 0.75-0.96), genistein (OR = 0.87; 95% CI: 0.78-0.98), and glycitein (OR = 0.89; 95% CI: 0.81-0.98) were associated with a reduction of prostate cancer risk, but total isoflavones (OR = 0...
August 9, 2016: International Journal of Food Sciences and Nutrition
Rubia C G Corrêa, Rosane M Peralta, Charles W I Haminiuk, Giselle Maria Maciel, Adelar Bracht, Isabel C F R Ferreira
Aging is an inevitable process influenced by genetic, lifestyle and environmental factors. Indirect evidence shows that several phytochemicals can have anti-aging capabilities, although direct evidence in this field is still limited. This report aims to provide a critical review on aspects related to the use of novel phytochemicals as anti-aging agents, to discuss the obstacles found when performing most anti-aging study protocols in humans, and to analyze future perspectives. In addition to the extensively studied resveratrol, epicatechin, quercetin and curcumin, new phytochemicals have been reported to act as anti-aging agents, such as the amino acid L-theanine isolated from green tea, and the lignans arctigenin and matairesinol isolated from Arctium lappa seeds...
September 13, 2016: Critical Reviews in Food Science and Nutrition
Entela Hodaj, Olga Tsiftsoglou, Sokol Abazi, Dimitra Hadjipavlou-Litina, Diamanto Lazari
The present phytochemical investigation of the seeds of Centaurea vlachorum led to the isolation and characterisation of four compounds including two indole alkaloids N-(p-coumaroyl) serotonin (1) and moschamine (2) and two dibenzylbutyrolactone lignans matairesinol (3) and arctiin (4). This is the first report on the isolation of non-volatile secondary metabolites from C. vlachorum. The chemataxonomic significance of these compounds was summarised. Moreover, the isolated compounds were tested for their free radical scavenging activity using the following in vitro assays: (i) interaction with the free stable radical of DPPH (1,1-diphenyl-2-picrylhydrazyl), (ii) inhibition of linoleic acid peroxidation with the dihydrochloric acid of 2,2-Azobis-2-amidinopropane (AAPH)...
September 9, 2016: Natural Product Research
M Arimoto, S Matsuura, C Muro, H Tsujibo, E Matsumura, H Yamaguchi, Y Inamori
All the lignans tested in a bioassay with Brassica campestris L. subsp. rapa Hook. fil. et Anders inhibited the root growth of this plant, except for deoxypicropodophyllin. The effects of functional groups in the molecule on the inhibitory activity of these compounds were studied. It is suggested that the methylenedioxyl group and the stereochemical configuration of the lactone junction of podophyllotoxin derivatives were closely related to the inhibitory activity. The O-methyl derivative of two hydroxyl groups of matairesinol greatly enhanced the inhibition of root growth in this plant...
January 1994: Bioscience, Biotechnology, and Biochemistry
Janne J Jokinen, Arno Sipponen
Significance: The treatment of chronic wounds results in an enormous drain on healthcare resources in terms of workload, costs, frustration, and impaired quality of life, and it presents a clinical challenge for physicians worldwide. Effective local treatment of a chronic wound has an important role, particularly in patients who are-because of their poor general condition, diminished life expectancy, or unacceptable operative risk-outside of surgical treatment. Recent Advances: Since 2002, our multidisciplinary research group has investigated the properties of Norway spruce (Picea abies) resin in wound healing and its therapeutic applications in wound care...
May 1, 2016: Advances in Wound Care
Yoon-Young Sung, A Yeong Lee, Ho Kyoung Kim
ETHNOPHARMACOLOGICAL RELEVANCE: Forsythia suspensa is used in traditional medicine to treat inflammation. To clarify the anti-inflammatory and anti-allergic effects of F. suspensa fruits, we determined the therapeutic effects of crude extract, fractions, and a constituent from F. suspensa fruits on a murine atopic dermatitis (AD) model. MATERIALS AND METHODS: We investigated the inhibitory effects of F. suspensa extract (FSE), extract fractions, and the constituent matairesinol on histamine release from MC/9 mast cells activated by compound 48/80 and the development of AD-like skin lesions and symptoms in NC/Nga mice exposed to Dermatophagoides farinae (mite) extract...
July 1, 2016: Journal of Ethnopharmacology
Andrea Quartieri, Rocío García-Villalba, Alberto Amaretti, Stefano Raimondi, Alan Leonardi, Maddalena Rossi, Francisco Tomàs-Barberàn
SCOPE: This study aimed to improve the knowledge of secoisolariciresinol diglucoside (SDG) transformation by human gut microbiota. METHODS AND RESULTS: SDG-supplemented microbiota cultures were inoculated with the feces of five subjects. The same volunteers received a flaxseed supplement for 7 days. SDG metabolites in cultures, feces, and urine were monitored by LC-ESI-QTOF and LC-DAD. In all cultures, SDG was deglycosylated to secoisolariciresinol (SECO) within 12 h...
July 2016: Molecular Nutrition & Food Research
Liisa Uusitalo, Maija Salmenhaara, Merja Isoniemi, Alicia Garcia-Alvarez, Lluís Serra-Majem, Lourdes Ribas-Barba, Paul Finglas, Jenny Plumb, Pirkko Tuominen, Kirsti Savela
The purpose of this study was to estimate the intake of selected bioactive compounds from fennel-containing plant food supplements (PFS) among Finnish consumers. The estimated average intake of estragole was 0.20mg/d, of trans-anethole 1.15mg/d, of rosmarinic acid 0.09mg/d, of p-coumaric acid 0.0068mg/d, of kaempferol 0.0034mg/d, of luteolin 0.0525μg/d, of quercetin 0.0246mg/d, of matairesinol 0.0066μg/d and of lignans 0.0412μg/d. The intakes of kaempferol, quercetin, luteolin, matairesinol and lignans from PFS were low in comparison with their dietary supply...
March 1, 2016: Food Chemistry
Susana Alejandra Palma-Duran, Graciela Caire-Juvera, María del Refugio Robles-Burgeño, María Isabel Ortega-Vélez, María de Lourdes Gutiérrez-Coronado, María del Carmen Bermúdez Almada, Karina Chávez-Suárez, Melissa Campa-Siqueiros, Patricia Grajeda-Cota, María del Socorro Saucedo-Tamayo, Ana Isabel Valenzuela-Quintanar
Phytoestrogens have generated interest in human health in view of their potential effect to reduce the risk of developing chronic diseases. Serum levels of phytoestrogens have been proposed as an alternative to measure the exposure of phytoestrogens. We evaluated the use of serum as a biomarker of phytoestrogen's intake in healthy women. Phytoestrogens in serum (luteolin, kaempferol, equol, biochanin A, formononetin, quercetin, naringenin, coumestrol, secoisolariciresinol, genistein, matairesinol, enterolactone, enterodiol, daidzein, glycitein and resveratrol) were analyzed by HPLC-ESI-MS...
2015: International Journal of Food Sciences and Nutrition
Sonja L B Arneaud, John R Porter
Podophyllotoxin (PPT) is a plant natural product that serves as a precursor for the synthesis of many well-known chemotherapeutic drugs. The limited availability and high demand for the source plants of PPT have led to the exploration of alternative sources for this compound. In this study, we utilized the endophytic fungus Phialocephala podophylli (strain PPE7) that we isolated from the rhizomes of Podophyllum peltatum and is known to produce detectable amounts of PPT in broth culture. To date, the complete PPT biosynthetic pathway has yet to be determined in any species...
December 2015: Molecular Biotechnology
Shan Su, Michael Wink
Arctium lappa is a well-known traditional medicinal plant in China (TCM) and Europe that has been used for thousands of years to treat arthritis, baldness or cancer. The plant produces lignans as secondary metabolites, which have a wide range of bioactivities. Yet, their antiaging potential has not been explored. In this study, we isolated six lignans from A. lappa seeds, namely arctigenin, matairesinol, arctiin, (iso)lappaol A, lappaol C, and lappaol F. The antioxidant and antiaging properties of the isolated lignans were studied using Caenorhabditis elegans as a relevant animal model...
September 2015: Phytochemistry
Rong Tang, Minjian Chen, Kun Zhou, Daozhen Chen, Jing Yu, Weiyue Hu, Ling Song, Bo Hang, Xinru Wang, Yankai Xia
During pregnancy, human exposure to endogenous estrogens and xenoestrogens (such as lignans) may comprehensively impact the gestational maintenance and fetal growth. We measured the concentrations of 5 lignans and the profile of 13 estrogen metabolites (EMs) in the urine samples of 328 pregnant women and examined their associations with birth outcomes. We found significantly positive associations between gestational age and urinary matairesinol (MAT), enterodiol (END) and enterolactone (ENL), as well as 16-hydroxylation pathway EMs...
October 2015: Environmental Pollution
Natalja P Nørskov, Anja Olsen, Anne Tjønneland, Anne Katrine Bolvig, Helle Nygaard Lærke, Knud Erik Bach Knudsen
Lignans have gained nutritional interest due to their promising role in the prevention of lifestyle diseases. However, epidemiological studies are in need of more evidence to link the intake of lignans to this promising role. In this context, it is necessary to study large population groups to obtain sufficient statistical power. Therefore, there is a demand for fast, sensitive, and accurate methods for quantitation with high throughput of samples. This paper presents a validated LC-MS/MS method for the quantitation of eight plant lignans (matairesinol, hydroxymatairesinol, secoisolariciresinol, lariciresinol, isolariciresinol, syringaresinol, medioresinol, and pinoresinol) and two enterolignans (enterodiol and enterolactone) in both human and pig plasma and urine...
July 15, 2015: Journal of Agricultural and Food Chemistry
Nathalie Jullian-Pawlicki, Michelle Lequart-Pillon, Luyen Huynh-Cong, David Lesur, Dominique Cailleu, François Mesnard, Jean Claude Laberche, Eric Gontier, Michèle Boitel-Conti
INTRODUCTION: Hairy root cultures of Linum sp. are an alternative for the high production of lignans. Linum perenne is known to produce arylnaphthalene-type lignans such as justicidin B, isojusticidin and diphyllin. OBJECTIVE: To elucidate the presence of aryltetralin-type lignan diastereoisomers, besides the known arylnaphthalene-type lignans, in hairy roots of Linum perenne, and to determine the configurations of one diastereoisomer of 6-methoxypodophyllotoxin (6-MPTOX)...
September 2015: Phytochemical Analysis: PCA
Shan Su, Xinlai Cheng, Michael Wink
OBJECTIVES: Arctigenin and matairesinol possess a diversity of bioactivities. Here we investigated the cytotoxicity of arctigenin and matairesinol against a T-cell lymphoma cell line CCRF-CEM and the underlying mechanisms that have not been explored before. METHODS: The cytotoxic activity was investigated using MTT assay. The cell cycle arrest and reactive oxygen species (ROS) accumulation were determined by flow cytometric analysis. The apoptosis induction was assessed using Annexin V/Propidium Iodide assay...
September 2015: Journal of Pharmacy and Pharmacology
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