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pinoresinol
phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diylbis(2-methoxy-, (1S-(1a,3aa,4a,6aa))-

Supplier Sponsors

Name:4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
CAS Number: 487-36-5Picture of molecule3D/inchi
FDA UNII: V4N1UDY811
Nikkaji Web:J322.968H
MDL:MFCD07784516
XlogP3-AA:2.30 (est)
Molecular Weight:358.39054000
Formula:C20 H22 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 556.00 to 557.00 °C. @ 760.00 mm Hg (est)
Flash Point: 555.00 °F. TCC ( 290.40 °C. ) (est)
logP (o/w): 1.591 (est)
Soluble in:
 water, 104 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
(+)-Pinoresinol 98%
BOC Sciences
For experimental / research use only.
Pinoresinol
Coompo
For experimental / research use only.
Pinoresinol from Plants ≥96%
Odor: characteristic
Use: Pinoresinol inhibits the enzyme a-glucosidase in vitro and may therefore act as a hypoglycemic agent. Pinoresinol possess in vitro chemoprevention properties. Increased apoptosis and cellular arrest at the G2/M stage in p53-proficient cells occurred. Pinoresinol dose-dependently decreased IL-6 and macrophage chemoattractant protein-1 secretions and NF-?B activity. Our findings suggest that plant lignans can be absorbed and metabolized in the small intestine and, among the plant lignans tested, Pinoresinol exhibited the strongest antiinflammatory properties by acting on the NF-?B signaling pathway, possibly in relation to its furofuran structure and/or its intestinal metabolism. Pinoresinol is found to occur as a minor component in the defensive secretion produced by glandular hairs of caterpillars of the cabbage butterfly, Pieris rapae. Pinoresinol was shown to be absent from the secretion if the larva was given a cabbage-free diet but present in the effluent if that diet was supplemented with pinoresinol. Pinoresinol is shown to be a feeding deterrent to ants (Formica exsectoides), indicating that it can complement the defensive action of the primary components of the secretion, a set of previously reported lipids called mayolenes. In the test with F. exsectoides, pinoresinol proved to be more potent than concomitantly tested mayolene-16.
Sigma-Aldrich: Sigma
For experimental / research use only.
Pinoresinol ≥95% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for pinoresinol usage levels up to:
 not for fragrance use.
 
Recommendation for pinoresinol flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73399
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
Chemidplus:0000487365
 
References:
 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73399
Pubchem (sid):135032830
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
Metabolomics Database:Search
KEGG (GenomeNet):C05366
HMDB (The Human Metabolome Database):Search
FooDB:FDB002760
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 elder black elder
Search Trop Picture
 flax
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 salsify black salsify
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 sesame
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Synonyms:
4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxyphenol
 phenol, 4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diylbis(2-methoxy-, (1S-(1a,3aa,4a,6aa))-
 phenol, 4,4'-[(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-
(±)-pinoresinol
(1S-(1alpha,3aalpha,4alpha,6aalpha))-4,4'-(tetrahydro-1H,3H-furo(3,4-c)furan-1,4-diyl bis(2-methoxyphenol)
4,4'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(2-methoxyphenol)
 

Articles:

PubMed:Isolation and Identification of α-Glucosidase and Protein Glycation Inhibitors from Stereospermum colais.
PubMed:Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG).
PubMed:Lignans and neolignans from the stems of Vibrunum erosum and their neuroprotective and anti-inflammatory activity.
PubMed:New guaian-type sesquiterpene from Wikstroemia indica.
PubMed:Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis.
PubMed:Plant lignans inhibit growth and trichothecene biosynthesis in Fusarium graminearum.
PubMed:Bioconversion of pinoresinol into matairesinol by use of recombinant Escherichia coli.
PubMed:Nutritional characterisation and bioactive components of commercial carobs flours.
PubMed:[Chemical constituents from stems of Aquilaria sinensis].
PubMed:Ultrasound-assisted emulsification-microextraction for the determination of phenolic compounds in olive oils.
PubMed:Lignans 7-hydroxymatairesinol and 7-hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells.
PubMed:Urease inhibitory constituents from Daphne retusa.
PubMed:[Chemical constituents from stems of Brucea mollis and their cytotoxic activity].
PubMed:New phenanthrene derivatives with nitric oxide inhibitory and radical-scavenging activities from Pholidota imbricata Hook.
PubMed:Effects of water availability on emerald ash borer larval performance and phloem phenolics of Manchurian and black ash.
PubMed:Pinoresinol inhibits proliferation and induces differentiation on human HL60 leukemia cells.
PubMed:A new lignan glucoside from the whole plants of Salvia scapiformis.
PubMed:[Lignans from Machilus robusta].
PubMed:Dirigent proteins: molecular characteristics and potential biotechnological applications.
PubMed:[Chemical constituents from twigs and leaves of Melodinus hemsleyanus].
PubMed:Four new lignans from Schisandra sphenanthera.
PubMed:[Chemical constituents from twigs and leaves of Melodinus hemsleyanus].
PubMed:Looking beyond sugars: phytochemical profiling and standardization of manna exudates from Sicilian Fraxinus excelsior L.
PubMed:[Chemical constituents from Litsea greenmaniana].
PubMed:Heat shock factor 1 inducers from the bark of Eucommia ulmoides as cytoprotective agents.
PubMed:[Chemical constituents from the linseed meal].
PubMed:Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.
PubMed:Role of protein farnesylation events in the ABA-mediated regulation of the Pinoresinol-Lariciresinol Reductase 1 (LuPLR1) gene expression and lignan biosynthesis in flax (Linum usitatissimum L.).
PubMed:Dietary intake and main sources of plant lignans in five European countries.
PubMed:Cytotoxic constituents from the leaves of Broussonetia papyrifera.
PubMed:[Chemical constituents from leaves of Rhododendron rubiginosum var rubiginosum].
PubMed:Phenols, lignans and antioxidant properties of legume and sweet chestnut flours.
PubMed:Expressed sequence tags and molecular cloning and characterization of gene encoding pinoresinol/lariciresinol reductase from Podophyllum hexandrum.
PubMed:The Effect of the Aerial Part of Lindera akoensis on Lipopolysaccharides (LPS)-Induced Nitric Oxide Production in RAW264.7 Cells.
PubMed:Chemical constituents of the root of Jasminum giraldii.
PubMed:[Chemical constituents from Daphne acutiloba].
PubMed:Alkyl and phenolic glycosides from Saussurea stella.
PubMed:Melanogenesis-inhibitory activity of aromatic glycosides from the stem bark of Acer buergerianum.
PubMed:Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye.
PubMed:A validated method for the determination of selected phenolics in olive oil using high-performance liquid chromatography with coulometric electrochemical detection and a fused-core column.
PubMed:Combination of preparative HPLC and HSCCC methods to separate phosphodiesterase inhibitors from Eucommia ulmoides bark guided by ultrafiltration-based ligand screening.
PubMed:Dietary intake and major sources of plant lignans in Latvian men and women.
PubMed:A new triterpenoid from Teucrium viscidum.
PubMed:Identification and characterization of cis-acting elements involved in the regulation of ABA- and/or GA-mediated LuPLR1 gene expression and lignan biosynthesis in flax (Linum usitatissimum L.) cell cultures.
PubMed:[Chemical constituents of the roots of Vaccinium bracteatum].
PubMed:Discovery of pinoresinol reductase genes in sphingomonads.
PubMed:Dietary intake of lignans and risk of esophageal and gastric adenocarcinoma: a cohort study in Sweden.
PubMed:Optimized expression of the dirigent protein AtDIR6 in Pichia pastoris and impact of glycosylation on protein structure and function.
PubMed:PPARγ agonist from Chromolaena odorata.
PubMed:A new lignan with anti-HBV activity from the roots of Bombax ceiba.
PubMed:Synthesis and characterization of new 5-linked pinoresinol lignin models.
PubMed:Immunolocalization of 8-5' and 8-8' linked structures of lignin in cell walls of Chamaecyparis obtusa using monoclonal antibodies.
PubMed:Comprehensive analysis of polyphenols in 55 extra virgin olive oils by HPLC-ECD and their correlation with antioxidant activities.
PubMed:Validation of FFQ-based assessment of dietary lignans compared with serum enterolactone in Swedish women.
PubMed:Influence of harvest year, cultivar and geographical origin on Greek extra virgin olive oils composition: a study by NMR spectroscopy and biometric analysis.
PubMed:Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells.
PubMed:Analytical evaluation of two monovarietal virgin olive oils cultivated in the south of Tunisia: Jemri-Bouchouka and Chemlali-Tataouin cultivars.
PubMed:Characterisation and phenolic profiles of two rare olive oils from southern Tunisia: Dhokar and Gemri-Dhokar cultivars.
PubMed:[Study on HPCE fingerprint of Eucommiae Cortex].
PubMed:Opposite stereoselectivities of dirigent proteins in Arabidopsis and schizandra species.
PubMed:Two new compounds isolated from Liriope muscari.
PubMed:Lignan constituents of Tilia amurensis and their biological evaluation on antitumor and anti-inflammatory activities.
PubMed:(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
PubMed:[Non-alkaloid chemical constituents from Coptis chinensis].
PubMed:[Study on the chemical constituents of the roots of Dendropanax chevalieri].
PubMed:Determinants of dietary lignan intake in a representative sample of young Spaniards: association with lower obesity prevalence among boys but not girls.
PubMed:The effect of light on gene expression and podophyllotoxin biosynthesis in Linum album cell culture.
PubMed:A new lignan with anti-tumour activity from Polygonum perfoliatum L.
PubMed:A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum.
PubMed:Orthoquinone and naphthalenone derivatives from Berrya ammonilla and their anti-inflammatory activity.
PubMed:Phenolic compounds from the aerial parts of Diplomorpha canescens.
PubMed:A model of dirigent proteins derived from structural and functional similarities with allene oxide cyclase and lipocalins.
PubMed:[Studies on chemical constitutes from callus cultures of Stellera chamaejasme].
PubMed:Natural hypolignification is associated with extensive oligolignol accumulation in flax stems.
PubMed:Time-course changes in fungal elicitor-induced lignan synthesis and expression of the relevant genes in cell cultures of Linum album.
PubMed:A clinical trial testing the safety and efficacy of a standardized Eucommia ulmoides Oliver bark extract to treat hypertension.
PubMed:Multiple component quantitative analysis for the pattern recognition and quality evaluation of Kalopanacis Cortex using HPLC.
PubMed:Antioxidant phenolic compounds of cassava (Manihot esculenta) from Hainan.
PubMed:Validation of a HPLC-tandem MS/MS method for pharmacokinetics study of (+)-pinoresinol-di-β-D-glucopyranoside from Eucommia ulmoides Oliv extract in rats' plasma.
PubMed:Inhibitory constituents of Nardostachys chinensis on nitric oxide production in RAW 264.7 macrophages.
PubMed:Structure identification and fermentation characteristics of pinoresinol diglucoside produced by Phomopsis sp. isolated from Eucommia ulmoides Oliv.
PubMed:Sesquiterpenoids and lignans from the roots of Valeriana officinalis L.
PubMed:Nigerian foodstuffs with prostate cancer chemopreventive polyphenols.
PubMed:Phytoestrogen consumption from foods and supplements and epithelial ovarian cancer risk: a population-based case control study.
PubMed:Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae).
PubMed:Milled wood lignin: a linear oligomer.
PubMed:Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds.
PubMed:[Simultaneous determination of four active compounds in tiangou capsules by HPLC].
PubMed:Phenolic compounds from the roots of Jordanian viper's grass, Scorzonera judaica.
PubMed:Bioactive neolignans and lignans from the bark of Machilus robusta.
PubMed:Constituents from Senecio scandens and their antioxidant bioactivity.
PubMed:Identification and quantitative determination of lignans in Cedrus atlantica resins using 13C NMR spectroscopy.
PubMed:Antinociceptive, free radical-scavenging, and cytotoxic activities of Acanthus hirsutus Boiss.
PubMed:[Aromatic constituents of Heteroplexis micocephal and their bioactivities].
PubMed:[Quantitative determination of pinoresinol diglucoside in Eucommiae unloads by NIRS].
PubMed:Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans.
PubMed:Identification and quantification of lignans in wheat bran by gas chromatography-electron capture detection.
PubMed:[Determination of pinoresinol diglucoside in Qing' e Pills by ultra performance liquid chromatography].
PubMed:Large-scale co-expression approach to dissect secondary cell wall formation across plant species.
PubMed:[Alkaloids and lignans from stems of Piper betle].
PubMed:Lignin composition and structure in young versus adult Eucalyptus globulus plants.
PubMed:Antinociceptive and anti-inflammatory activities of ethyl acetate fraction from Zanthoxylum armatum in mice.
PubMed:Effect of dietary intervention on serum lignan levels in pregnant women - a controlled trial.
PubMed:[Studies on the chemical constituents of Pachysandra terminalis and their antioxidant activity].
PubMed:[Studies on the chemical constituents of Solanum nigrum].
PubMed:[Chemical constituents of stems and branches of Adina polycephala].
PubMed:Antifungal effect of (+)-pinoresinol isolated from Sambucus williamsii.
PubMed:Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: kinetics of an endwise process.
PubMed:Salicylic acid improves podophyllotoxin production in cell cultures of Linum album by increasing the expression of genes related with its biosynthesis.
PubMed:Pinoresinol from the fruits of Forsythia koreana inhibits inflammatory responses in LPS-activated microglia.
PubMed:[Studies on the chemical constituents of extract with water from Forsythia suspensa].
PubMed:Development and validation of an ultra high-performance liquid chromatographic method for the determination of a diastereomeric impurity in (+)-pinoresinol diglucoside chemical reference substance.
PubMed:Characterization of phenolic compounds in Helichrysum melaleucum by high-performance liquid chromatography with on-line ultraviolet and mass spectrometry detection.
PubMed:[Study on the quality standards of decoction pieces of salt Eucommia].
PubMed:Pinoresinol-lariciresinol reductases with opposite enantiospecificity determine the enantiomeric composition of lignans in the different organs of Linum usitatissimum L.
PubMed:Lignans from the tuber-barks of Colocasia antiquorum var. esculenta and their antimelanogenic Activity.
PubMed:Effect of olive ripeness on chemical properties and phenolic composition of Chétoui virgin olive oil.
PubMed:[Chemical constituents of Galium verum].
PubMed:Cytotoxic phenolic compounds from Chionanthus retusus.
PubMed:Crystal structure and catalytic mechanism of leucoanthocyanidin reductase from Vitis vinifera.
PubMed:Mass fragmentation study of the trimethylsilyl derivatives of arctiin, matairesinoside, arctigenin, phylligenin, matairesinol, pinoresinol and methylarctigenin: their gas and liquid chromatographic analysis in plant extracts.
PubMed:Hepatoprotective effect of pinoresinol on carbon tetrachloride-induced hepatic damage in mice.
PubMed:Quantitative analysis and chromatographic fingerprinting for the quality evaluation of Forsythia suspensa extract by HPLC coupled with photodiode array detector.
PubMed:An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols.
PubMed:Improved method for identifying and quantifying olive oil phenolic compounds and their metabolites in human plasma by microelution solid-phase extraction plate and liquid chromatography-tandem mass spectrometry.
PubMed:Tentative characterization of novel phenolic compounds in extra virgin olive oils by rapid-resolution liquid chromatography coupled with mass spectrometry.
PubMed:Metabolic engineering of lignan biosynthesis in Forsythia cell culture.
PubMed:Structural characterization of the lignin from jute (Corchorus capsularis) fibers.
PubMed:Dietary intake and urinary excretion of lignans in Finnish men.
PubMed:Molecular cloning and characterization of a novel isoflavone reductase-like gene (FcIRL) from high flavonoids-producing callus of Fagopyrum cymosum.
PubMed:Conferin, potent antioxidant and anti-inflammatory isoflavone from Caragana conferta Benth.
PubMed:Absolute configuration of (+)-pinoresinol 4-O-[6''-O-galloyl]-beta-D-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tanarius.
PubMed:Characterization of variation in the lignan content and composition of winter rye, spring wheat, and spring oat.
PubMed:[Isolation and identification of compounds from marine mangrove plant Avicennia marina].
PubMed:Intake of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol in relation to vascular inflammation and endothelial dysfunction in middle age-elderly men and post-menopausal women living in Northern Italy.
PubMed:Flavan-3-ols having a gamma-lactam from the roots of Actinidia arguta inhibit the formation of advanced glycation end products in vitro.
PubMed:Lignan derivatives from the stem bark of Syzygium cumini (L.) Skeels.
PubMed:Pinoresinol-4,4'-di-O-beta-D-glucoside from Valeriana officinalis root stimulates calcium mobilization and chemotactic migration of mouse embryo fibroblasts.
PubMed:Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy.
PubMed:Isolation and bioactivities of furfuran type lignan compounds from edible plants.
PubMed:tabAnti-HER2 (erbB-2) oncogene effects of phenolic compounds directly isolated from commercial Extra-Virgin Olive Oil (EVOO).
PubMed:Anti-inflammatory and analgesic components from "hierba santa," a traditional medicine in Peru.
PubMed:Study of antimalarial activity of chemical constituents from Diospyros quaesita.
PubMed:Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil.
PubMed:[Studies on lignan constituents of Clematis parviloba].
PubMed:Comparison of atmospheric pressure chemical ionization and electrospray ionization mass spectrometry for the detection of lignans from sesame seeds.
PubMed:Furofuranic glycosylated lignans: a gas-phase ion chemistry investigation by tandem mass spectrometry.
PubMed:Analyzing effects of extra-virgin olive oil polyphenols on breast cancer-associated fatty acid synthase protein expression using reverse-phase protein microarrays.
PubMed:Minor compounds from the stem bark of Chinese mangrove associate Catunaregam spinosa.
PubMed:Lignans and other constituents of the fruits of Euterpe oleracea (Acai) with antioxidant and cytoprotective activities.
PubMed:Dietary consumption of phytochemicals and breast cancer risk in Mexican women.
PubMed:Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
PubMed:Lignan and flavonoid glycosides from Urtica laetevirens Maxim.
PubMed:Correlations of the phenolic compounds and the phenolic content in some Spanish and French olive oils.
PubMed:Glycosides from whole plants of Glechoma hederacea L.
PubMed:Tracking monolignols during wood development in lodgepole pine.
PubMed:Hinokinin biosynthesis in Linum corymbulosum Reichenb.
PubMed:Rearranged ent-kauranes from the stems of Tricalysia dubia and their biological activities.
PubMed:Lignan glycosides from the leaves of Osmanthus heterophyllus.
PubMed:Stereochemistry of lignans in Phaleria macrocarpa (Scheff.) Boerl.
PubMed:Characterization of Arabidopsis thaliana pinoresinol reductase, a new type of enzyme involved in lignan biosynthesis.
PubMed:Asymmetric biomimetic oxidations of phenols: the mechanism of the diastereo- and enantioselective synthesis of thomasidioic acid.
PubMed:Enhancing lignan biosynthesis by over-expressing pinoresinol lariciresinol reductase in transgenic wheat.
PubMed:A new neolignan glycoside from the leaves of Acer truncatum.
PubMed:Dietary phytoestrogens, including isoflavones, lignans, and coumestrol, in nonvitamin, nonmineral supplements commonly consumed by women in Canada.
PubMed:Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell lines.
PubMed:Lignan profile in seeds of modern and old Italian soft wheat (Triticum aestivum L.) cultivars as revealed by CE-MS analyses.
PubMed:[Non-saponins from Solanum nigrum L].
PubMed:Inhibitory effects of olive oil phenolics on invasion in human colon adenocarcinoma cells in vitro.
PubMed:[Studies on lignin glycosides in root from Ilex pubescens].
PubMed:[Chemical constituents from Pyrethrum tatsienense].
PubMed:[Research on the quality changes in pre- and post-processed pieces of Eucommia ulmoides].
PubMed:Lignans from the stems of Sambucus williamsii and their effects on osteoblastic UMR106 cells.
PubMed:Irrigation effects on quality, phenolic composition, and selected volatiles of virgin olive oils cv. Leccino.
PubMed:Isolation and purification of lignans from Magnolia biondii Pamp by isocratic reversed-phase two-dimensional liquid chromatography following microwave-assisted extraction.
PubMed:A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol.
PubMed:Inhibitory activity against tobacco mosaic virus (TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var. roxburghiana.
PubMed:Assessing phytochemical intake in a group of Mexican women.
PubMed:A new lignan glycoside from the stem bark of Styrax japonica S. et Z.
PubMed:Lignans from the fruits of Cornus kousa Burg. and their cytotoxic effects on human cancer cell lines.
PubMed:Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.
PubMed:Relation between plasma enterodiol and enterolactone and dietary intake of lignans in a Dutch endoscopy-based population.
PubMed:Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin.
PubMed:Lipoxygenase inhibitory constituents of the fruits of noni (Morinda citrifolia) collected in Tahiti.
PubMed:Dietary lignan intake and postmenopausal breast cancer risk by estrogen and progesterone receptor status.
PubMed:Comparison of analytical methodologies based on 1h and 31p NMR spectroscopy with conventional methods of analysis for the determination of some olive oil constituents.
PubMed:(+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B.
PubMed:Simultaneous determination of 12 major constituents in Forsythia suspensa by high performance liquid chromatography--DAD method.
PubMed:[Content comparison of pinoresinol diglucoside in original and reborn bark of Eucommia ulmoides].
PubMed:[Studies on chemical constituents of Serissa serissoides roots].
PubMed:Pinoresinol: A lignol of plant origin serving for defense in a caterpillar.
PubMed:Phenols and lignans from Chenopodium album.
PubMed:Assessing exposure to lignans and their metabolites in humans.
PubMed:Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan.
PubMed:Intakes of 4 dietary lignans and cause-specific and all-cause mortality in the Zutphen Elderly Study.
PubMed:Pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds.
PubMed:Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin.
PubMed:Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester.
PubMed:Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans.
PubMed:Capillary electrophoresis-electrospray ionization-mass spectrometry method to determine the phenolic fraction of extra-virgin olive oil.
PubMed:Lignans from Arnica species.
PubMed:Antifungal and antibacterial activities of Araucaria araucana (Mol.) K. Koch heartwood lignans.
PubMed:Evaluation of phenolic compounds in virgin olive oil by direct injection in high-performance liquid chromatography with fluorometric detection.
PubMed:[Chemical constituents from root of Lasianthus acuminatissimus I].
PubMed:Tyrosinase inhibitory lignans from the methanol extract of the roots of Vitex negundo Linn. and their structure-activity relationship.
PubMed:Cytotoxic lignans from the stems of Helicteres hirsuta collected in Indonesia.
PubMed:Quantification of lignans in food using isotope dilution gas chromatography/mass spectrometry.
PubMed:Lignans and secoiridoids from the root bark of Chionanthus virginicus L.: isolation, identification and HPLC analysis.
PubMed:Electrophoretic identification and quantitation of compounds in the polyphenolic fraction of extra-virgin olive oil.
PubMed:Preclinical evaluation of rapeseed, raspberry, and pine bark phenolics for health related effects.
PubMed:Lignin primary structures and dirigent sites.
PubMed:Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum.
PubMed:Separation and identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with postcolumn solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR).
PubMed:Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol.
PubMed:Intake of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in Dutch men and women.
PubMed:Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits.
PubMed:Antitumor and antiinflammatory constituents from Celtis sinensis.
PubMed:Piperidinyl amides with insecticidal activity from the maritime plant Otanthus maritimus.
PubMed:Lignans and their degraded derivatives from Sarcostemma acidum.
PubMed:Polyphenols from plants used in traditional Indonesian medicine (Jamu): uptake and antioxidative effects in rat H4IIE hepatoma cells.
PubMed:A new pinoresinol-type lignan from Ligularia kanaitizensis.
PubMed:Involvement of extracellular dilignols in lignification during tracheary element differentiation of isolated Zinnia mesophyll cells.
PubMed:Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values.
PubMed:Crystal structures of apo-form and binary/ternary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans.
PubMed:New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica.
PubMed:Triterpenic derivatives of Achillea alexandri-regis BORNM. & RUDSKI.
PubMed:The content of lignan glycosides in Forsythia flowers and leaves.
PubMed:Qualitative and semiquantitative analysis of phenolic compounds in extra virgin olive oils as a function of the ripening degree of olive fruits by different analytical techniques.
PubMed:Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry.
PubMed:A new seco-abietane-type diterpene from the stem bark of Picea glehni.
PubMed:Constituents of the seeds of Hernandia ovigera with inhibitory activity against cyclooxygenase-2.
PubMed:Bioactive lignans from a cultivar of Helianthus annuus.
PubMed:Chiral silylation reagents: determining configuration via NMR-spectroscopic coanalysis.
PubMed:Lignoids in insects: chemical probes for the study of ecdysis, excretion and Trypanosoma cruzi-triatomine interactions.
PubMed:Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in foods.
PubMed:Stability control of valerian ground material and extracts: a new HPLC-method for the routine quantification of valerenic acids and lignans.
PubMed:Antitubercular constituents of Valeriana laxiflora.
PubMed:Plant lignans in soy-based health supplements.
PubMed:Lignans of Rosa multiflora roots.
PubMed:A comprehensive approach for quantitative lignin characterization by NMR spectroscopy.
PubMed:Acetylated glucuronide triterpene bidesmosidic saponins from Symplocos glomerata.
PubMed:Kinetic study of coniferyl alcohol radical binding to the (+)-pinoresinol forming dirigent protein.
PubMed:Effect of cultivar and processing method on the contents of polyphenols in table olives.
PubMed:Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC).
PubMed:Liquid chromatography method for plant and mammalian lignans in human urine.
PubMed:The formation of beta-beta structures in lignin biosynthesis--are there two different pathways?
PubMed:Crystal structures of pinoresinol-lariciresinol and phenylcoumaran benzylic ether reductases and their relationship to isoflavone reductases.
PubMed:Chemical constituents from Amentotaxus yunnanensis and Torreyayunnanensis.
PubMed:[Chemical constituents from Alyxia sinensis (II)].
PubMed:Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol.
PubMed:Rye bread in the diet of pigs enhances the formation of enterolactone and increases its levels in plasma, urine and feces.
PubMed:Antifungal effects of different organic extracts from Melia azedarach L. on phytopathogenic fungi and their isolated active components.
PubMed:Bioactive constituents of Leptadenia arborea.
PubMed:Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds.
PubMed:[Studies on the chemical constituents of the herba of Cuscuta chinensis].
PubMed:New biflavanones and bioactive compounds from Stellera chamaejasme L.
PubMed:[Development of healthy beverage from Eucommla ulmoides foliage].
PubMed:[Studies on the chemical constituents of the root of Pimpinella thellungiana].
PubMed:[Studies on chemical constituents of Ligustrum obtusifolium Sieb. et Zucc].
PubMed:Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis.
PubMed:Pinoresinol from Ipomoea cairica cell cultures.
PubMed:Lignans isolated from valerian: identification and characterization of a new olivil derivative with partial agonistic activity at A(1) adenosine receptors.
PubMed:Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oil.
PubMed:Stereochemical diversity in lignan biosynthesis of Arctium lappa L.
PubMed:Secondary and quaternary structures of the (+)-pinoresinol-forming dirigent protein.
PubMed:Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.
PubMed:The western red cedar (Thuja plicata) 8-8' DIRIGENT family displays diverse expression patterns and conserved monolignol coupling specificity.
PubMed:Olive-oil consumption and health: the possible role of antioxidants.
PubMed:Acid hydrolysis of secoiridoid aglycons during storage of virgin olive oil.
PubMed:Lignans from the rhizomes of Coptis japonica differentially act as anti-inflammatory principles.
PubMed:In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol.
PubMed:Effects of some lignans and neolignans on the development and excretion of Rhodnius prolixus.
PubMed:In situ hybridization and immunolocalization of lignan reductases in woody tissues: implications for heartwood formation and other forms of vascular tissue preservation.
PubMed:Antimalarial compounds from Rhaphidophora decursiva.
PubMed:Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection.
PubMed:Sesquiterpene lactones and other constituents of Disynaphia multicrenulata from Argentina.
PubMed:[A reversed-phase high performance liquid chromatographic method for the determination of pinoresinol diglucopyranoside in Eucommia Ulmoides Oliv].
PubMed:7-feruloylloganin: an iridoid glucoside from stems of Lonicera insularis.
PubMed:Lignans from Strophanthus gratus.
PubMed:Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae).
PubMed:Effects of lignoids on a hematophagous bug, Rhodnius prolixus: feeding, ecdysis and diuresis.
PubMed:Phenylpropanoid derivatives and biflavones at different stages of differentiation and development of Araucaria angustifolia.
PubMed:Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum.
PubMed:Spectral comparisons of coniferyl and cinnamyl alcohol epoxide derivatives with a purported cis-epoxyconiferyl alcohol isolate.
PubMed:Identification of lignans as major components in the phenolic fraction of olive oil.
PubMed:The antioxidant/anticancer potential of phenolic compounds isolated from olive oil.
PubMed:Lipid peroxidation inhibitory activity of some constituents isolated from the stem bark of Eucalyptus globulus.
PubMed:Inhibition of low density lipoprotein oxidation by tetrahydrofurofuran lignans from Forsythia suspensa and Magnolia coco.
PubMed:An antioxidant lignan and other constituents from the root bark of Hibiscus syriacus.
PubMed:Isolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal.
PubMed:Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells.
PubMed:Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
PubMed:Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum.
PubMed:Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases.
PubMed:Inhibitory effect of lignans from the rhizomes of Coptis japonica var. dissecta on tumor necrosis factor-alpha production in lipopolysaccharide-stimulated RAW264.7 cells.
PubMed:Recombinant pinoresinol-lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions.
PubMed:Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG).
PubMed:Bioactive iridoids and a new lignan from Allamanda cathartica and Himatanthus fallax from the Suriname rainforest.
PubMed:Oxygen insertion in Sesamum indicum furanofuran lignans. Diastereoselective syntheses of enzyme substrate analogues.
PubMed:Enantioselective accumulation of (--)-pinoresinol through O-demethylation of (+/-)-eudesmin by Aspergillus niger.
PubMed:Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center.
PubMed:(+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase.
PubMed:[Effect of processing of the contents of pinoresinol diglucoside in cortex Eucommiae].
PubMed:[Studies on chemical constituents of roots of Euphorbia pekinensis].
PubMed:Pharmacologically active components of Todopon Puok (Fagraea racemosa), a medicinal plant from Borneo.
PubMed:Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc.
PubMed:Lignanes from the Brazilian Melia azedarach, and their activity in Rhodnius prolixus (Hemiptera, Reduviidae).
PubMed:Elicitor-Induced Spruce Stress Lignin (Structural Similarity to Early Developmental Lignins).
PubMed:A ferulic acid ester of sucrose and other constituents of Bhesa paniculata.
PubMed:A new phenylpropanoid glucoside and other constituents of Oenanthe javanica.
PubMed:[Biologically active lignins from Magnolia biondii Pamp].
PubMed:Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia.
PubMed:Lignification in cell suspension cultures of Pinus taeda. In situ characterization of a gymnosperm lignin.
PubMed:[Constituents of the leaves of Daphne pseudo-mezereum].
PubMed:An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol.
PubMed:On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol.
PubMed:Phenolic compounds from stem bark of Acanthopanax senticosus and their pharmacological effect in chronic swimming stressed rats.
PubMed:Lignans and other constituents from South and central american zanthoxylum species.
PubMed:[High performance liquid chromatography of pinoresinol diglucoside in Eucommaia ulmoides oliv bark].
PubMed:Wikstromol, antitumor lignan from Wikstroemia foetida var. oahuensis Gray and Wikstroemia uva-ursi Gray (Thymelaeaceae).
PubMed:Letter: Isolation and synthesis of pinoresinol diglucoside, a major antihypertensive principle of Tu-Chung(Eucommia ulmoides, Oliver).
PubMed:[Not Available].
 
Notes:
in plants; a furo[3,4-c]furan created from dimer of coniferyl alcohol.
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