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Sesamum indicum; seeds; furans; lignans; spectral analysis; chemical structure; biosynthesis; biochemical pathways; chemical reactions; chemical constituents of plants
... The phytochemical (+)-Medioresinol, a furofuran type lignan identification and isolation on the stem bark of Sambucus williamsii, which is a folk medicinal plant used in traditional medicine. (+)-Medioresinol is known to possess a lesishmanicidal activity and cardiovascular disease risk reduction but its antifungal effects have not yet been identified. In this study, to confirm (+)-Medioresinol's ...
... Depression is a mood disorder that is related to neuroinflammation and cognition loss. This study is aimed to determine the potential antidepressant effects of (+)-sesamin, a lignan component of sesame, in a mild stress-induced depression mouse model. CD-1 mice were treated with chronic unpredictable mild stress (CUMS) process and orally administrated with sesamin (50 mg/kg/d) for 6 weeks. Behavio ...
... The progression of chronic kidney disease (CKD) increases the risks of cardiovascular morbidity and end-stage kidney disease. Indoxyl sulfate (IS), which is derived from dietary l-tryptophan by the action of bacterial l-tryptophan indole-lyase (TIL) in the gut, serves as a uremic toxin that exacerbates CKD-related kidney disorder. A mouse model previously showed that inhibition of TIL by 2-aza-l-t ...
... Sesamum spp. (sesame) are known to accumulate a variety of lignans in a lineage‐specific manner. In cultivated sesame (Sesamum indicum), (+)‐sesamin, (+)‐sesamolin and (+)‐sesaminol triglucoside are the three major lignans found richly in the seeds. A recent study demonstrated that SiCYP92B14 is a pivotal enzyme that allocates the substrate (+)‐sesamin to two products, (+)‐sesamolin and (+)‐sesami ...
... Endothelial inflammation is an increasingly prevalent condition in the pathogenesis of many cardiovascular diseases. (-)-7(S)-hydroxymatairesinol (7-HMR), a naturally occurring plant lignan, possesses both antioxidant and anti-cancer properties and therefore would be a good strategy to suppress tumor necrosis factor-α (TNF-α)-mediated inflammation in vascular endothelial cells (VECs).: The objecti ...
... As one of the major global health issues, allergic disease represents a considerable burden both on individual patients and public health. (-)-Asarinin (Asa), a lignan isolated from the roots of Asiasari radix, was reported to be associated with anti-allergic effect, but its efficacy and mechanism of action remain unclear. This study investigated the inhibitory effect of Asa on allergic reaction a ...
... The neuroprotective effects and potential mechanisms of (-)-Syringaresinol-4-O-β-D-glucopyranoside (SRG), a natural lignan glycoside extracted from Cortex Albizziae, were investigated using corticosterone (CORT)-induced PC12 cells as an in vitro anxiety model. PC12 cells were treated with 100 μM CORT and 5, 10, or 20 μM SRG for 48 h. Cell viability and lactate dehydrogenase (LDH) leakage were meas ...
... (7R, 8S)-9-Acetyl-dehydrodiconiferyl alcohol (ADDA), a novel lignan compound isolated from Clematis armandii Franch (Ranunculaceae) stems, has been found to exert potential anti-inflammatory activities in vitro.To investigate the pharmacological effects and molecular mechanisms of ADDA on lipopolysaccharide (LPS)-induced activation and migration of macrophages.Macrophages were stimulated with LPS ...
... There is continuously accruing evidence to suggest the health benefits of consuming fruits and vegetables. Food supplements may represent an effective and acceptable method to deliver a way of providing bioactive compounds to consumers. The aim of this work was to characterize the (poly)phenolic composition of three plant-based food supplements designed to integrate and increase the daily intake o ...
Lu Yuanyuan; Xue Yongbo; Liu Junjun; Yao Guangmin; Li Dongyan; Sun Bin; Zhang Jinwen; Liu Yanfei; Qi Changxing; Xiang Ming; Luo Zengwei; Du Guang; Zhang Yonghui
... Three pairs of new 8-O-4′-type dinorneolignan enantiomers, (±)-acortatarinowins A–C (1a/1b–3a/3b), a pair of new 8-O-4′-type (4a/4b) and a pair of rare C7–C8′-type (5a/5b) neolignan enantiomers, (±)-acortatarinowins D and E, and a pair of new furofuran-type lignan enantiomers, (±)-acortatarinowin F (6a/6b), along with two pairs of known lignan enantiomers (7a/7b and 8a/8b), were obtained from the ...
Vanderlisa Rita Meleti; Viviane Rodrigues Esperandim; Luzio Gabriel Bocalon Flauzino; Anna Helena Prizantelli; Lucas Antônio de Lima Paula; Lizandra Guidi Magalhães; Wilson Roberto Cunha; Rosângela da Silva Laurentiz; Ana Paula da Rocha Pissurno; N.P. Dhammika Nanayakkara; Ana Carolina Pereira; Jairo Kenupp Bastos; Renato Luis Tâme Parreira; Renato Pereira Orenha; Márcio Luis Andrade e Silva
... This paper reports the synthesis of (±)-licarin A 1, a dihydrobenzofuran neolignan, resultant of an oxidative coupling reaction of isoeugenol and horseradish peroxidase (HRP) enzyme. Following, three semi-synthetic derivatives from this compound were obtained: benzylated (±)-licarin A 2, methylated (±)-licarin A 3 and acetylated (±)-licarin A 4. After structural elucidation and assignment by Nucle ...
... (±)-Torreyunlignans A–D (1a/1b–4a/4b), four pairs of new 8–9′ linked neolignan enantiomers featuring a rare (E)-2-styryl-1,3-dioxane moiety, were isolated from the trunk of Torreya yunnanensis. The structures were determined by combined spectroscopic and chemical methods, and the absolute configurations were elucidated by ECD calculations. The compounds were screened by using tritium-labeled adeno ...
... Guided by a feeding stimulant activity test on the olive weevil (Dyscerus perforatus), two compounds that showed potent feeding stimulant activity were isolated from the olive tree (Olea europaea). Based on their spectral data and a literature survey, they were identified as (−)-olivil (1) and (+)-1-acetoxypinoresinol (2). The activities of these minor lignans were significantly higher for the fem ...
... Flaxseed lignan, secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of secoisolariciresinol and found that (−)-secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes. Here we show the effects of (−)-secoisolariciresinol on high-fat diet-induced obesity in C57BL/6 male mice. Oral administrat ...
... 1,4-Benzodioxane lignans are a class of bioactive compounds that have received much attention through the years. Herein research pertaining to both 1,4-benzodioxane flavonolignans and 1,4-benzodioxane neolignans is presented. A novel synthesis of both traditional 1,4-benzodioxane flavonolignans and 3-deoxyflavonolignans is described. The antiviral and cytotoxic activities of 1,4-benzodioxane neoli ...
Apiaceae; lignans; lactones; spectral analysis; chemical structure; antineoplastic agents; humans; ovarian diseases; chemical constituents of plants; Tanzania
... Five compounds of iridoids, lignan and phenylpropanoid glycosides were isolated from the roots ofValeriana jatamansi by column chromatography. Their structures were elucidated as 11-methoxyviburtinal (1), baldrinal (2), prinsepiol-4-O-β-D-glucoside (3), coniferin (4), and hexacosanic acid (5) by spectroscopic analysis. 11-Methoxyviburtinal was a new compound, and others were isolated from the plan ...
... Thirteen naturally occurring 1H-cyclopenta[b]benzofuran lignans of the rocaglamide type as well as one naturally occurring aglain congener all of them isolated from three Aglaia species (Aglaia duperreana, A. oligophylla and A. spectabilis) collected in Vietnam were studied for their antiproliferative effects using the human monocytic leukemia cell lines MONO-MAC-1 and MONO-MAC-6. Only rocaglamide ...
... An activity-directed fractionation and purification process was used to identify the antioxidative components of adlay hulls. Hulls of adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) were extracted with methanol and then separated into water, 1-butanol, ethyl acetate, and hexane fractions. The 1-butanol-soluble fraction exhibited greater capacity to scavenge 2,2'-diphenyl-1-picrylhydrazyl (DPPH) ...
Wrightia; flavonoids; glycosides; lignans; nuclear magnetic resonance spectroscopy
Abstract:
... A new aminobenzoyl glycoside, 2-aminobenzoyl O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and two new megastigmane glycosides, wrightiaionosides A (10), and B (11), were isolated along with 17 known compounds, including four benzoxazinoid glycosides (2-5), one indole diglycoside (6), three simple aromatic glycosides (7-9), three megastigmane glycosides (12-14), five flavonoid glycosides (15-1 ...
... The aqueous-ethanolic extract (AEE) of high altitude Podophyllum hexandrum has earlier been reported to render a radioprotective effect against lethal gamma radiation in in vitro model. AEE has also been reported to possess metal chelating and DNA protecting properties. The present study was undertaken to isolate and characterize the bioactive principle present in AEE and investigate its role in r ...
... Two new 5-methyl ether flavone glucosides (7,4′,5′-trihydroxy-5,3′-dimethoxyflavone 7-O-β-D-glucopyranoside and 7,4′-dihydroxy-5-methoxyflavone 7-O-β-D-glucopyranoside) were isolated from the leaves of Thai mangrove Bruguiera gymnorrhiza together with 7,3′,4′,5′-tetrahydroxy-5-methoxyflavone, 7,4′,5′-trihydroxy-5,3′-dimethoxyflavone, luteolin 5-methyl ether 7-O-β-D-glucopyranoside, 7,4′-dihydroxy- ...
Giorgio Biasiotto; Isabella Zanella; Federica Predolini; Ivonne Archetti; Moris Cadei; Eugenio Monti; Marcello Luzzani; Barbara Pacchetti; Paola Mozzoni; Roberta Andreoli; Giuseppe De Palma; Federico Serana; Annika Smeds; Diego Di Lorenzo
... 7-Hydroxymatairesinol (7-HMR) is a plant lignan abundant in various concentrations in plant foods. The objective of this study was to test HMRLignan™, a purified form of 7-HMR, and the corresponding Picea abies extract (total extract P. abies; TEP) as dietary supplements on a background of a high-fat diet (HFD)-induced metabolic syndrome in mice and in the 3T3-L1 adipogenesis model. Mice, 3 weeks ...
Human immunodeficiency virus 1; Illicium; antiviral properties; bark; chemistry; lignans; nuclear magnetic resonance spectroscopy; spectral analysis
Abstract:
... Two new 8-O-4′-neolignans, difenneolignans A and B (1 and 2), together with six known neolignans (3–8), were isolated from the stem bark of Illicium difengpi. The structures of 1–8 were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were also tested for their anti-HIV-1 activities. The results revealed significant activities for compounds 1 and ...
... The genus Clerodendrum Linn., originally belonging to Verbenaceae, was assigned to Lamiaceae by APG (Angiosperm Phylogeny Group) Ⅱ. Seven abietane diterpenoids (1–7) along with three anthraquinones (8–10) and one neolignan (11) were isolated and identified from the stems of Clerodendrum trichotomum Thunb.. Among them, compounds 4, 6 and 8–11 were reported from the genus Clerodendrum Linn. for the ...
... Four new abscisic acid related compounds (1-4), together with (+)-abscisic acid (5), (+)-β-D-glucopyranosyl abscisate (6), (6S,9R)-roseoside (7), and two lignan glucosides ((+)-pinoresinol mono-β-D-glucopyranoside (8) and 3-(β-D-glucopyranosyloxymethyl)-2- (4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (9)) were isolated from the antioxidative ethanol extract o ...
Macaranga tanarius; lignans; glucosides; chemical constituents of plants; chemical structure; spectral analysis; stereochemistry; antioxidant activity; Japan
Abstract:
... A lignan glucoside, (+)-pinoresinol 4-O-[6"-O-galloyl]-β-d-glucopyranoside (1), and two megastigmane glucosides, named macarangiosides E and F (2, 3), together with 15 known compounds (4-18) were isolated from leaves of Macaranga tanarius (L.) Müll.-Arg. (Euphorbiaceae). Their structures were elucidated by spectroscopic and chemical analyses. In addition, the absolute stereochemistry of macarangi ...
René Velázquez-Jiménez; J. Martín Torres-Valencia; Carlos M. Cerda-García-Rojas; Juan D. Hernández-Hernández; Luisa U. Román-Marín; J. Jesús Manríquez-Torres; Mario A. Gómez-Hurtado; Alejandro Valdez-Calderón; Virginia Motilva; Sofía García-Mauriño; Elena Talero; Javier Ávila; Pedro Joseph-Nathan
... The ethanol extract from the dried exudate of Bursera fagaroides (Burseraceae) showed significant cytotoxic activity in the HT-29 (human colon adenocarcinoma) test system. The extract provided four podophyllotoxin related lignans, identified as (7′R,8R,8′R)-(−)-deoxypodophyllotoxin (3), (7′R,8R,8′R)-(−)-morelensin (4), (8R,8′R)-(−)-yatein (5), and (8R,8′R)-(−)-5′-desmethoxyyatein (6), whose spectr ...
... Plant lignans are diphenolic compounds ingested with whole grains and seeds and converted to enterolignans by the colonic microbiota. In the present study, we investigated absorption and metabolism of plant lignans and enterolignans in vivo after consumption of cereal-based diets. Six pigs fitted with catheters in the mesenteric artery and portal vein and with a flow probe attached to the portal v ...
... SCOPE: Sesamin is a major lignan in sesame seeds and has various physiological effects. Although metabolism of sesamin by cytochrome P450 or intestinal microflora has been reported, little is known concerning the mass balance, pharmacokinetics, and tissue distribution of sesamin. METHODS AND RESULTS: Absorption, distribution, metabolism, and excretion of [¹⁴C]sesamin were investigated after a sing ...
Taiwania cryptomerioides; biosynthesis; environmental factors; enzymes; genetic factors; genotype; heartwood; heritability; lignans; linear models; liquid chromatography; mass spectrometry; nuclear magnetic resonance spectroscopy; prediction; principal component analysis; provenance; secondary metabolites; wood quality
Abstract:
... Lignans are major bioactive secondary metabolites, which are also formed in the heartwood (hW) of Taiwania (Taiwania cryptomerioides). Their biosynthesis pathways are complex and involve many enzymes and intermediates. To evaluate the extent of the genetic components leading to the variety of lignans in Taiwania hW, 35 Taiwania genotypes of four provenances were surveyed using the proton nuclear m ...
Linum; biomass; callus; cytotoxicity; high performance liquid chromatography; in vitro culture; lignans; medicinal plants; neoplasm cells; plantlets; seedlings; shoots
Abstract:
... Justicidin B, an arylnaphthalene lignan, has strong cytotoxicity on chronic myeloid and chronic lymphoid leukemia cell lines. The first report of the production of justicidin B in a Linum species concerned in vitro culture of Linum austriacum. Therefore, culture characterization and presence of arylnaphthalene-type lignans in calli and plantlets of Linum tenuifolium from section Linastrum, Linum b ...
... Aconitum carmichaelii, belonging to the Ranunculaceae family, is a widely used traditional herbal plant in Asian countries, especially in China. The lateral (“Fuzi”) and mother (“Chuanwu”) roots are the two main plant parts used in Traditional Chinese Medicine (TCM), where they are used in the treatment of acute myocardial infarction, heart failure, rheumatoid arthritis, and as analgesics. In orde ...
... Acorus Linnaeus is a genus of perennial herbs distributed from the northern temperate to the subtropical regions, and has been widely used as traditional folk medicine in China and India since ancient times. Phytochemical studies have shown the presence of numerous beneficial compounds, such as phenylpropanoids, lignans, sesquiterpenoids, alkaloids and others. Neuropharmacological studies have rev ...
... The stability and reactivity of five different thermostable fungal laccases from the species Trametes hirsuta, Melanocarpus albomyces, Thielavia arenaria (two laccases) and Chaetomium thermophilum were investigated in the presence of organic solvents. Oxidations of small organic phenolic compounds, matairesinol and 7-hydroxymatairesinol lignans, as well as synthetic lignin dehydrogenation polymer ...
... (+)-Conocarpan (CNCP), a neolignan frequently found in many medicinal and edible plants displays a broad spectrum of bioactivity. Here, we demonstrated that CNCP induced apoptotic cell death in human kidney-2 (HK-2) cells in a concentration-dependent manner (IC₅₀ = 19.3 μM) and led to the sustained elevation of intracellular Ca²⁺ ([Ca²⁺]ᵢ). Lower extracellular Ca²⁺ concentrations from 2.3 mM to 0 ...
Piper; Trypanosoma cruzi; benznidazole; carbon; drugs; ethyl acetate; human cell lines; leaves; lignans; mechanism of action; metabolism; mice; nuclear magnetic resonance spectroscopy; parasites; spectral analysis; stable isotopes; toxicity; tropics; vegetation
Abstract:
... Piperaceae species are abundant in the tropics and are important components of secondary vegetation. Many of these plants have received considerable attention due to their wide range of biological activities. Here, the trypanocidal activity of extracts and fractions with different polarities obtained from Colombian Piper jericoense plant was evaluated. A furofuran lignan, (1S,3aS,4S,6aS)-1-(3′,4′- ...
Quercus acutissima; additives; antioxidant activity; antioxidants; bark; industry; lignans; lignin; mass spectrometry; nuclear magnetic resonance spectroscopy; polyphenols
Abstract:
... Acutissimanide (1), a new lignin, together with 11 known polyphenols (2–12) were isolated from the bark of the deciduous oak tree, Quercus acutissima Carruth. The structure of compound 1 was determined using multidimensional ¹H and ¹³C NMR and mass spectroscopy. The antioxidant properties of compounds 1–12 were investigated using a 1,1-diphenyl-2-picryhydrazyl radical-scavenging assay with compoun ...
... Two new acyl flavone glucosides, luteolin-4⿲-O-(6-p-hydroxybenzoyl)-β-d-glucopyranoside (leontopodioside A, 1) and luteolin-4⿲-O-[6-(2-methylbutyryl)]-β-d-glucopyranoside (leontopodioside B, 2), and a new acyl lignan glucoside, lariciresinol-9-angeloyl-4-O-β-d-glucopyranoside (leontopodiosideC, 3) were isolated from the whole plants of Leontopodium leontopodioides (Asteraceae). Their structures we ...
... Nine new acyl glycosides, obtusifosides A–I (1–9), and eight known compounds have been isolated from an EtOH extract of the stems of Erycibe obtusifolia. Their structures were elucidated on the basis of a spectroscopic data analysis (NMR, HRESIMS, and CD) and chemical evidence. The hepatoprotective effects of some of the compounds from d-galactosamine-induced cytotoxicity in HL-7702 hepatic cells ...
Asteraceae; Trypanosoma congolense; aerial parts; animals; bovine trypanosomiasis; enantiomers; high performance liquid chromatography; lignans; nuclear magnetic resonance spectroscopy
Abstract:
... Eight isovaleryllignans (1–4 and 8–11), three isovalerylphenylpropanoids (5–7), three known lignans (12–14), and four known compounds were isolated from an extract of the aerial part of Brachanthemum gobicum. The structures of the isolated compounds were elucidated based on NMR and MS data analyses. The enantiomers of compounds 1–3, 5, 8, and 9 were isolated using chiral-phase HPLC, and the absolu ...
matairesinol; data collection; nutrient databanks; lignans; plant-based foods; food composition; East Asia
Abstract:
... The dietary lignans secoisolariciresinol (SEC) and matairesinol (MAT) are phytoestrogens structurally similar to the hormone estrogen and may exert estrogenic effects in the body. Quantification of dietary intake of phytoestrogens is of particular interest for the study of hormone-related diseases. The purpose of this project was to expand the Cancer Research Center of Hawaii Food Composition Tabl ...
Nan Shang; José A. Guerrero-Analco; Lina Musallam; Ammar Saleem; Asim Muhammad; Brendan Walshe-Roussel; Alain Cuerrier; John T. Arnason; Pierre S. Haddad
... ETHNOPHARMACOLOGICAL RELEVANCE: Diabetes is a growing epidemic worldwide, especially among indigenous populations. Larix laricina was identified through an ethnobotanical survey as a traditional medicine used by Healers and Elders of the Cree of Eeyou Istchee of northern Quebec to treat symptoms of diabetes and subsequent in vitro screening confirmed its potential. MATERIALS AND METHODS: We used a ...