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plant lignans

Joël Doussot, Véronique Mathieu, Cyril Colas, Roland Molinié, Cyrielle Corbin, Josiane Montguillon, Laeticia Moreno Y Banuls, Sullivan Renouard, Frédéric Lamblin, Patricia Dupré, Benoit Maunit, Robert Kiss, Christophe Hano, Eric Lainé
Podophyllotoxin, a lignan still extracted from the rhizomes of Podophyllum hexandrum (Berberidaceae), is the starting molecule for the semisynthesis of widely used anticancer drugs such as etoposide. However, this source is threatened by the over-collection of P. hexandrum. Plants belonging to the Linaceae and Cupressaceae families could be attractive alternative sources with species that contain the lignan podophyllotoxin or its precursors and derivatives. Wild flax species, such as Linum flavum, as well as some Juniperus and Callitris species were investigated for their lignan content, and the in vitro antiproliferative capacity of their extracts was assayed on four tumor cell lines...
October 24, 2016: Planta Medica
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
Hong Jin, Shu Yang, Jun-Xing Dong
Four new lignan glycosides (1-4), named procumbenosides I, K, L, and M, together with cleistanthin B (5) reported for the first time in the genus Justicia, and 5 other known arylnaphthalene lignan glycosides (6-10) were isolated from the whole plant of Justicia procumbens. The structures of the new compounds were elucidated by extensive one-dimensional (1D) and two-dimensional (2D) NMR experiments and mass spectrometry. Procumbenoside M (4) was a rare sesquilignan glycoside never previously reported in the species of Justicia...
October 21, 2016: Journal of Asian Natural Products Research
Fadia S Youssef, Mohamed L Ashour, Mansour Sobeh, Hesham A El-Beshbishy, Abdel Nasser Singab, Michael Wink
BACKGROUND: The Australian plant Eremophila maculata F. Muell (Scrophulariaceae) is cultivated worldwide as an ornamental plant. PURPOSE: This study was designed to assess the antioxidant and hepatoprotective activities of a methanol extract from E. maculata leaves (EMM) both in vitro and in vivo (rats) experiments. Detailed phytochemical study was done on the extract followed by molecular docking experiments on TNF-α ascertain the efficacy of the isolated compounds...
November 15, 2016: Phytomedicine: International Journal of Phytotherapy and Phytopharmacology
Raphael Gasper, Isabelle Effenberger, Piotr Kolesinski, Barbara Terlecka, Eckhard Hofmann, Andreas Schaller
Dirigent proteins impart stereoselectivity to phenoxy radical coupling reactions in plants and thus play an essential role in the biosynthesis of biologically active natural products. This includes the regio- and enantioselective coupling and subsequent cyclization of two coniferyl alcohol radicals to pinoresinol as the committed step of lignan biosynthesis. The reaction is controlled by dirigent proteins which, depending on the species and protein, direct the reaction to either (+)- or (-)-pinoresinol. We present the crystal structure of the (-)-pinoresinol forming Dirigent Protein 6 from Arabidopsis thaliana (AtDIR6) with data to 1...
October 17, 2016: Plant Physiology
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 quantification of free and total content (free + bound) of eight plant lignans (matairesinol, hydroxymatairesinol, secoisolariciresinol, lariciresinol, isolariciresinol, syringaresinol, medioresinol and pinoresinol) and the two enterolignans (enterodiol and enterolactone) in cereal based diets/bread and feces...
October 14, 2016: Journal of Agricultural and Food Chemistry
Li-Long Pan, Xi-Ling Wang, Xiao-Ling Luo, Si-Yu Liu, Peng Xu, Jin-Feng Hu, Xin-Hua Liu
Previously, we have shown that boehmenan, a natural product isolated from the dried stem of Caulis clematidis armandii, exhibits various biological activities. The current study investigated the effects of boehmenan on the growth of human epidermoid carcinoma A431 cells. Cell viability and 50% inhibiting concentration (IC50) were assessed by CellTiter-Glo luminescent cell viability assay. Cell cycle arrest was measured by flow cytometry. Intracellular reactive oxygen species production and mitochondrial membrane potential (ΔΨm) collapse were analyzed by a fluorescence spectrophotometer...
October 3, 2016: Integrative Cancer Therapies
Samah M El Sohafy, Aly M Metwally, Abdalla A Omar, Masouda E Amer, Mohamed M Radwan, Maged S Abdel-Kader, Sayed A El Toumy, Mahmoud A ElSohly
The ethanol extract of Cynara cornigera L. was fractionated and the fractions were subjected to hepatoprotective assays using Wistar albino rats at a dose of 500 and 250mg/kg. The liver injury was induced in rats using carbon tetrachloride. Biochemical parameters such as aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP) and total bilirubin were estimated as reflections of the liver condition, with silymarin as a positive control. Phytochemical investigation and chromatographic separation of the hepatoprotective fractions led to the isolation of a new sesqui-lignan namely cornigerin (1), along with eight known compounds: apigenin (2), luteolin (3), β-sitosterol glycoside (4), apigenin 7-O-β-D-glucopyranoside (5), luteolin-7-O-β-D-glucopyranoside (6), apigenin-7-O-rutinoside (7), cynarin 1,5-di-O-caffeoylquinic acid (8), and apigenin-7-O-β-D-glucuronide (9)...
September 28, 2016: Fitoterapia
Qi Li, Yan Zhang, Junling Shi, Yilin Wang, Haobin Zhao, Dongyan Shao, Qingsheng Huang, Hui Yang, Mingling Jin
Pinoresinol (Pin) and pinoresinol monoglucoside (PMG) are plant-derived lignan molecules with multiple functions. We showed previously that the endophytic fungus Eucommiaulmoides Oliverendophytic Phomopsis sp. XP-8 is able to produce Pin and PMG. Cultured XP-8 showed inhibition on HepG-2 and K562 cells and the major effective compounds were identified. The fungal culture significantly inhibited the activities of HepG-2 and K562 cells by decreasing their viability and inducing apoptosis via up-regulating the expression of apoptosis-related genes...
September 22, 2016: Anti-cancer Agents in Medicinal Chemistry
Anita Kumari, Dharam Singh, Sanjay Kumar
Podophyllotoxin is an aryltetralin lignan synthesized in several plant species, which is used in chemotherapies for cancers and tumor treatment. More potent semisynthetic derivatives of podophyllotoxin such as etoposide and teniposide are being developed and evaluated for their efficacy. To meet the ever increasing pharmaceutical needs, species having podophyllotoxin are uprooted extensively leading to the endangered status of selective species mainly Sinopodophyllum hexandrum. This has necessitated bioprospection of podophyllotoxin from different plant species to escalate the strain on this endangered species...
September 20, 2016: Critical Reviews in Biotechnology
Xifeng Zhai, George Binh Lenon, Charlie C L Xue, Chun-Guang Li
Euonymus alatus (E. alatus) is a medicinal plant used in some Asian countries for treating various conditions including cancer, hyperglycemia, and diabetic complications. This review outlines the phytochemistry and bioactivities of E. alatus related to antidiabetic actions. More than 100 chemical constituents have been isolated and identified from E. alatus, including flavonoids, terpenoids, steroids, lignans, cardenolides, phenolic acids, and alkaloids. Studies in vitro and in vivo have demonstrated the hypoglycemic activity of E...
2016: Evidence-based Complementary and Alternative Medicine: ECAM
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
Andrei Mocan, Gokhan Zengin, Gianina Crişan, Adriano Mollica
Considerable interest has been shown in natural sources and their compounds in developing new therapeutically agents for different diseases. In this framework, investigations performed on this topic play a central role for human health and drug development process. Schisandra chinensis (Turcz.) Baill is a medicinal and edible plant showing highly advantageous bioactivity and nutritional value. The main bioactive compounds from its fruits are lignans, derivatives of dibenzocyclooctadiene whereas concerning its leaves, phenolic acids, and flavonoids are dominant...
September 5, 2016: Journal of Enzyme Inhibition and Medicinal Chemistry
Jingjing Wu, Haoliang Li, Guoli Huang, Yegao Chen
A new cyclopeptide, neriitide A (1) and a new lignan, neriilignan (2), along with six known compounds including two diterpenoids, three sesquiterpenoids and one sterol were isolated from the leaves of Podocarpus neriifolius. Their structures were elucidated by means of extensive spectroscopic analysis including HREIMS, 1D and 2D NMR techniques. This is the first report of cyclopeptide and lignan separated from this plant.
August 31, 2016: Natural Product Research
Meyada Khaled, Ghania Belaaloui, Zhen-Zhou Jiang, Xiong Zhu, Lu-Yong Zhang
Recently, biologically active compounds isolated from plants used in herbal medicine have been the center of interest. Deoxypodophyllotoxin (DPT), structurally closely related to the lignan podophyllotoxin, was found to be a potent antitumor and antiproliferative agent, in several tumor cells, in vitro. However, DPT has not been used clinically yet because of the lack of in vivo studies. This study is the first report demonstrating the antitumor effect of DPT on MDA-MB-231 human breast cancer xenografts in nude mice...
October 2016: Journal of Infection and Chemotherapy: Official Journal of the Japan Society of Chemotherapy
Bao Vue, Qiao-Hong Chen
BACKGROUND: The generic name "flavonolignan" was created in 1968 for a relatively small class of naturally occurring hybrid molecules biogenetically originated from ubiquitous flavonoids and lignans (phenylpropanoids). The first group of flavonolignans was extracted from Silybum marianum that has long been used for hepatoprotection. Recently, the medicinal merit of flavonolignans has been extended to the prostate cancer management. METHODS: Systematic interpretation and summarization of the relevant literature...
August 23, 2016: Current Medicinal Chemistry
Madumani Amararathna, Michael R Johnston, H P Vasantha Rupasinghe
Lung cancer may be prevented by a diet rich in fruits and vegetables as they are enriched with dietary antioxidant polyphenols, such as flavonoids, proanthocyanidins, lignans, stilbenes, and phenolic acids. Dietary polyphenols exert a wide range of beneficial biological functions beyond their antioxidative properties and are involved in regulation of cell survival pathways leading to anticarcinogenic and antimutagenic functions. There are sufficient evidence from in vitro, in vivo, and epidemiological studies to suggest that the dietary intervention of polyphenols in cancer prevention, including the chemopreventive ability of dietary polyphenols, act against lung carcinogens...
2016: International Journal of Molecular Sciences
Pilar Gaya, Margarita Medina, Abel Sánchez-Jiménez, José Mᵃ Landete
Phytoestrogens are plant-derived polyphenols with a structure similar to human estrogens. The three main groups of phytoestrogens, isoflavones, ellagitannins, and lignans, are transformed into equol, urolithins, and enterolignans, respectively, by bacteria. These metabolites have more estrogenic/antiestrogenic and antioxidant activities than their precursors, and they are more bioavailable. The aim of this study was to analyze the metabolism of isoflavones, lignans and ellagitannins by gut microbiota, and to study the possible correlation in the metabolism of these three groups of phytoestrogens...
2016: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Cara L Frankenfeld
Recent evidence supports that the gut microbial community, independently and/or interactively with dietary intake, is a target for reducing CVD risk through its effects on cardiometabolic risk factors. Dietary phytoestrogens may be a source for interactive effects. Phytoestrogens, such as isoflavones, lignans, and flavonoids, are compounds found in plants that have estrogenic or anti-estrogenic activities, as well as antioxidant, anti-proliferative, or apoptotic actions. Given these physiological activities, phytoestrogens may have a role in cardiometabolic health...
July 28, 2016: Molecular Nutrition & Food Research
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