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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
Lorenzo Cecchi, Marzia Innocenti, Fabrizio Melani, Marzia Migliorini, Lanfranco Conte, Nadia Mulinacci
Herein we describe the influence of olive oil refining processes on the lignan profile. The detection of new isobaric lignans is suggested to reveal frauds in commercial extra-Virgin Olive Oils. We analyzed five commercial olive oils by HPLC-DAD-TOF/MS to evaluate their lignan content and detected, for the first time, some isobaric forms of natural (+)-pinoresinol and (+)-1-acetoxypinoresinol. Then we analyzed partially and fully-refined oils from Italy, Tunisia and Spain. The isobaric forms occur only during the bleaching step of the refining process and remain unaltered after the final deodorizing step...
March 15, 2017: Food Chemistry
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
Gorazd Drevenšek, Mojca Lunder, Eva Tavčar Benković, Borut Štrukelj, Samo Kreft
BACKGROUND: Silver fir trunk extract (SFTE) is a complex mixture of antioxidative polyphenols (lignans and phenolic acids) from the trunks of silver fir trees (Abies alba, lignum). In our previous study, we have shown that SFTE exerts strong antioxidative and protective effects against atherogenic, diet-induced arterial wall damage. OBJECTIVE: The aim of the present study was to test the potential protective effects of SFTE and its compounds, two phenolic acids (p-coumaric and protocatechuic acids) in ischemia-reperfusion injury of isolated rat hearts...
2016: Food & Nutrition Research
Sanna Nybacka, Heléne Bertéus Forslund, Maria Hedelin
A diet questionnaire (DQ) designed to assess habitual diet and phyto-oestrogen intake was developed. This study aimed to examine the validity of the DQ in men, with and without having prostate cancer. The DQ was validated against alkylresorcinol metabolites measured in urine as objective biomarkers of whole grain wheat and rye (WG) intake, and a 4-d estimated food record (FR) was used for relative comparison. Participants (n 61) completed both methods and provided spot urine samples. We found a statistically significant correlation between the DQ and FR for reported whole grain intake and isoflavonoids, as well as for intake of macronutrients, except protein...
2016: Journal of Nutritional Science
Tania Fernández-Navarro, Nuria Salazar, Isabel Gutiérrez-Díaz, Borja Sánchez, Patricia Rúas-Madiedo, Clara G de Los Reyes-Gavilán, Abelardo Margolles, Miguel Gueimonde, Sonia González
PURPOSE: Short-chain fatty acids (SCFAs) formation by intestinal bacteria is regulated by many different factors, among which dietary fibre is currently receiving most attention. However, since fibre-rich foods are usually good dietary sources of phenolic compounds, which are also known to affect the microbiota, authors hypothesize that the regular intake of these bioactive compounds could be associated with a modulation of faecal SCFA production by the intestinal microbiota. METHODS: In this work, food intake was recorded by means of a validated Food Frequency Questionnaire...
October 15, 2016: European Journal of Nutrition
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
Lennard Schröder, Dagmar Ulrike Richter, Birgit Piechulla, Mareike Chrobak, Christina Kuhn, Sandra Schulze, Sybille Abarzua, Udo Jeschke, Tobias Weissenbacher
Hereinwe investigated the effect of elderflower extracts (EFE) and of enterolactone/enterodiol on hormone production and proliferation of trophoblast tumor cell lines JEG-3 and BeWo, as well as MCF7 breast cancer cells. The EFE was analyzed by mass spectrometry. Cells were incubated with various concentrations of EFE. Untreated cells served as controls. Supernatants were tested for estradiol production with an ELISA method. Furthermore, the effect of the EFE on ER/ER/PR expression was assessed by immunocytochemistry...
October 8, 2016: Nutrients
Mirka Laavola, Tiina Leppänen, Heikki Eräsalo, Mari Hämäläinen, Riina Nieminen, Eeva Moilanen
Nortrachelogenin is a pharmacologically active lignan found in knot extracts of Pinus sylvestris. In previous studies, some lignans have been shown to have anti-inflammatory properties, which made nortrachelogenin an interesting candidate for our study. In inflammation, bacterial products and cytokines induce the expression of inducible nitric oxide synthase, cyclooxygenase-2, and microsomal prostaglandin E synthase-1. These enzymes synthesize factors, which, together with proinflammatory cytokines, are important mediators and drug targets in inflammatory diseases...
October 13, 2016: Planta Medica
Ryota Araki, Yosuke Hiraki, Shoji Nishida, Yuka Inatomi, Takeshi Yabe
Emotional impairments such as depressive symptoms often develop in patients with sustained and systemic immune activation. The objective of this study is to investigate the effect of gomisin N, a dibenzocyclooctadiene lignan isolated from the dried fruits of Schisandra chinensis (Turcz.) Baill., which exhibited inhibitory effects of the bacterial endotoxin lipopolysaccharide (LPS)-induced NO production in a screening assay, on inflammation-induced depressive symptoms. We examined the effects of gomisin N on inflammation induced by LPS in murine microglial BV-2 cells and on LPS-induced behavioral changes in mice...
September 28, 2016: Journal of Pharmacological Sciences
Kuo Xu, Ya-Nan Yang, Zi-Ming Feng, Jian-Shuang Jiang, Pei-Cheng Zhang
Two new phenolic glycosides with a rare β-d-glucopyranosyl-(1→3)-α-l-rhamnopyranosyl moiety (1, 2), one new dihydrobenzofuran derivative (3), one new pyrazine derivative (4), two new furofuran lignan glycosides (5, 6), and six known compounds (7-12) were isolated from the rhizomes of Atractylodes lancea. The structures of these compounds were elucidated by extensive spectroscopic analyses combined with the experimental and calculated electronic circular dichroism and the Rh2(OCOCF3)4-induced circular dichroism for configurational assignments...
September 29, 2016: Bioorganic & Medicinal Chemistry Letters
Yuki Nakano, Masaaki Nasu, Mana Kano, Hiroshi Kameoka, Tetsuya Okuyama, Mikio Nishizawa, Yukinobu Ikeya
Guaiac resin, extracted from the heartwood of Guaiacum officinale L. or G. sanctum L., is speculated to have anti-inflammatory effects. Lignans were purified from guaiac resin (also known as gum guaiacum) by monitoring the nitric oxide (NO) production in rat hepatocytes treated with an inflammatory cytokine interleukin-1β (IL-1β). Six lignans were purified from guaiac resin and identified as: dehydroguaiaretic acid (1), (+)-trans-1,2-dihydrodehydroguaiaretic acid (2), furoguaiaoxidin (3), meso-dihydroguaiaretic acid (4), furoguaiacin (i...
October 5, 2016: Journal of Natural Medicines
Soroush Rahimi Khoigani, Ahmad Rajaei, Sayed Amir Hossein Goli
The aim of this study was to evaluate phenolics profile and antioxidant activity of Stachys lavandulifolia. Total phenolics (TP), total flavonoids (TF), DPPH• assay (IC50), ferric ion reducing antioxidant power (FRAP) and total antioxidant capacity (TAC) of the methanolic extract were measured. The content of TP, TF, IC50, FRAP and TAC, were obtained as 16.59 gallic acid equiv./g dry matter (DM), 4.48 mg quercetin equiv./g DM, 2.07 (μg/mL), 0.014 (absorbance/mg phenolic) and 14.61 (mg BHT equiv./g DM), respectively...
October 6, 2016: Natural Product Research
Ban-Ban Li, Jia-Lin Li, Na Li, Shi-Zhou Qi, Hyun-Sun Lee, Le Zhang, Shan-Shan Xing, Zhen-Dong Tuo, Long Cui
Two new furofuran lignans were isolated from the stems of Acanthopanax senticosus, along with seven known compounds. Their structures were all determined by spectroscopic analyses and chemical methods. All the isolates were evaluated for in vitro inhibitory activity against DGAT1 and DGAT2. Compounds 1 and 2 were found to exhibit selective inhibitory activity on DGAT1 with IC50 values 89.5 ± 1.5 and 57.5 ± 1.3 µM, respectively.
October 4, 2016: Archives of Pharmacal Research
Chung Sub Kim, Lalita Subedi, Oh Wook Kwon, Hyun Bong Park, Sun Yeou Kim, Sang Un Choi, Kang Ro Lee
Five new lignan glycosides, wasabisides A-E (1-5), and four known phenolic compounds (6-9), were isolated from the roots of Wasabia japonica. The chemical structures of the new compounds (1-5) were determined through spectroscopic analysis and chemical methods. All isolated compounds (1-9) were evaluated for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells, for their effects on nitric oxide levels in lipopolysaccharide-stimulated murine microglia BV2 cells, and for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and BT549)...
October 4, 2016: Journal of Natural Products
Yusnita Rifai, Harold B Tani, Muhammad Nur, Muhammad Aswad, Subehan Lallo, Elly Wahyudin
The oxidative demethylation procedure for a new epoxy lignan isolated from Piper nigrum was applied to the synthesis of 3'-methoxy-3",4"-(methylenedioxy)-2,5-epoxylignan-4'-ol-6'-one. This compound inhibited the mRNA expression of the protein patched homolog (Ptch) in human pancreatic cancer cells (PANC1) and therefore might be valuable as a probe for tumor-related disease. The pharmacokinetic profile of 3'-methoxy-3",4"-(methylenedioxy)-2,5-epoxylignan-4'-ol-6'-one was rapidly determined using ultra-fast liquid chromatography...
October 4, 2016: Archiv der Pharmazie
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
Vinod Bhatt, Sushila Sharma, Neeraj Kumar, Upendra Sharma, Bikram Singh
The current study presents isolation and characterization of twelve compounds including catechin (1), isovitexin (2), hesperidin (3), psoralin (4), eudesmin (5), kobusin (6), fargesin (7), sesamin (8), asarinin (9), planispine-A (10), α-sanshool (11) and vitexin (12), from the leaves of Zanthoxylum armatum. Further, two rapid and simple ultra performance liquid chromatography-diode array detection (UPLC-DAD) methods were developed for the simultaneous quantitative determination of isolated compounds from Z...
September 26, 2016: Journal of Pharmaceutical and Biomedical Analysis
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