Advances in the Synthesis of Lignan Natural Products

Lignans comprise a family of secondary metabolites existing widely in plants and also in human food sources. As important components, these compounds play remarkable roles in plants’ ecological functions as protection against herbivores and microorganisms. Meanwhile, foods rich in lignans have revealed potential to decrease of risk of cancers. To date, a number of promising bioactivities have been found for lignan natural products and their unnatural analogues, including antibacterial, antiviral, antitumor, antiplatelet, phosphodiesterase inhibition, 5-lipoxygenase inhibition, HIV reverse transcription inhibition, cytotoxic activities, antioxidant activities, immunosuppressive activities and antiasthmatic activities. Therefore, the synthesis of this family and also their analogues have attracted widespread interest from the synthetic organic chemistry community. Herein, we outline advances in the synthesis of lignan natural products in the last decade.

• Publication year

  2018

• Venue

  Molecules

• Publication date

  2018-12-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.3390/molecules23123385PMID 30572693PMCID 6321261
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Naturally occurring furofuran lignans: structural diversity and biological activities

  2019cited by this paper
• Bioinspired total synthesis of (−)-gymnothelignan L

  2018cited by this paper
• Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps.

  2018cited by this paper
• Flow Photochemistry as a Tool for the Total Synthesis of (+)-Epigalcatin.

  2018cited by this paper
• Ni-Catalyzed Regioselective Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling and Application to the Concise Synthesis of Lignan Natural Products.

  2018influential reference
• Bioinspired Asymmetric Synthesis of (-)-Gymnothelignan V.

  2018cited by this paper
• Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities

  2018cited by this paper
• Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis.

  2018cited by this paper
• Asymmetric total synthesis of (+)-ovafolinins A and B.

  2018cited by this paper
• Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

  2018cited by this paper
• The total synthesis of sevanol, a novel lignan isolated from the thyme plant (Thymus armeniacus)

  2018cited by this paper
• Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis.

  2018cited by this paper
• Catalytic Enantioselective Synthesis of (-)-Podophyllotoxin.

  2017cited by this paper
• Asymmetric synthesis of ent-fragransin C1.

  2017cited by this paper
• Total Synthesis of Ovafolinins A and B: Unique Polycyclic Benzoxepin Lignans through a Cascade Cyclization.

  2017cited by this paper
• Asymmetric synthesis of furofurans

  2017cited by this paper
• An Optimized and General Synthetic Strategy To Prepare Arylnaphthalene Lactone Natural Products from Cyanophthalides

  2017cited by this paper
• SYNFORM ISSUE 2017/11

  2017cited by this paper
• Recent advances in research on lignans and neolignans

  2016cited by this paper
• The Chemical Synthesis of Aryltetralin Glycosides

  2016cited by this paper
• Dual Catalysis Strategies in Photochemical Synthesis

  2016cited by this paper
• Formal synthesis of (-)-podophyllotoxin through the photocyclization of an axially chiral 3,4-bisbenzylidene succinate amide ester--a flow photochemistry approach.

  2016cited by this paper
• The chemical synthesis of aryltetralin glycosides.

  2016cited by this paper
• Recent advances in research on lignans and neolignans.

  2016cited by this paper
• Silver(I)-Catalyzed Regioselective Construction of Highly Substituted α-Naphthols and Its Application toward Expeditious Synthesis of Lignan Natural Products.

  2015cited by this paper
• A bio-inspired total synthesis of tetrahydrofuran lignans.

  2015cited by this paper
• Essences in Metabolic Engineering of Lignan Biosynthesis

  2015cited by this paper
• The Total Synthesis of Retrojusticidin B, Justicidin E, and Helioxanthin.

  2015cited by this paper
• Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition-Metal-Catalyzed, and Radical Reaction Steps.

  2015cited by this paper
• Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.

  2015cited by this paper
• Asymmetric total synthesis of (−)-lingzhiol via a Rh-catalysed [3+2] cycloaddition

  2014cited by this paper
• Highly functionalized and potent antiviral cyclopentane derivatives formed by a tandem process consisting of organometallic, transition-metal-catalyzed, and radical reaction steps.

  2014cited by this paper
• Bioinspired total synthesis of gymnothelignan N.

  2014cited by this paper
• Collective synthesis of several 2,7'-cyclolignans and their correlation by chemical transformations.

  2013cited by this paper
• Recent advances in the metabolic engineering of lignan biosynthesis pathways for the production of transgenic plant-based foods and supplements.

  2013cited by this paper
• Conformation and reactivity in dibenzocyclooctadienes (DBCOD). A general approach to the total synthesis of fully substituted DBCOD lignans via borostannylative cyclization of α,ω-diynes

  2013influential reference
• Total synthesis of (±)-sacidumlignans D and A through Ueno-Stork radical cyclization reaction.

  2013cited by this paper
• Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

  2013cited by this paper
• Palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes: synthesis of justicidin B and retrojusticidin B.

  2013cited by this paper
• Enantioselective Total Synthesis of (+)‐Galbulin via Organocatalytic Domino Michael—Michael—Aldol Condensation.

  2012cited by this paper
• Shining light on photoredox catalysis: theory and synthetic applications.

  2012cited by this paper
• A concise total synthesis of deoxyschizandrin and exploration of its antiproliferative effects and those of structurally related derivatives.

  2012cited by this paper
• Enantioselective total synthesis of (+)-galbulin via organocatalytic domino Michael-Michael-aldol condensation.

  2012cited by this paper
• On the stereochemistry of acetylide additions to highly functionalized biphenylcarbaldehydes and multi-component cyclization of 1,n-diynes. Syntheses of dibenzocyclooctadiene lignans

  2012cited by this paper
• Asymmetric synthesis of (+)-galbelgin, (-)-kadangustin J, (-)-cyclogalgravin and (-)-pycnanthulignenes A and B, three structurally distinct lignan classes, using a common chiral precursor.

  2011cited by this paper
• Nickel-catalyzed asymmetric Ullmann coupling for the synthesis of axially chiral tetra-ortho-substituted biaryl dials.

  2010cited by this paper
• Synthesis and the Biological Evaluation of Arylnaphthalene Lignans as Anti‐hepatitis B Virus Agents

  2010cited by this paper
• Nickel‐Catalyzed Asymmetric Ullmann Coupling for the Synthesis of Axially Chiral Tetra‐ortho‐Substituted Biaryl Dials.

  2010cited by this paper
• An Acyl-Claisen Approach toTetrasubstituted Tetrahydrofuran Lignans: Synthesis of FragransinA2, Talaumidin, and Lignan Analogues

  2009cited by this paper
• Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins.

  2009cited by this paper
• An update on lignans: natural products and synthesis.

  2009cited by this paper
• Stereoselective synthesis of 3-alkyl-2-aryltetrahydrofuran-4-ols: total synthesis of (+/-)-paulownin.

  2008cited by this paper
• Advances in the Synthesis of Aryltetralin Lignan Lactones

  2007cited by this paper
• Biosynthesis of lignans and norlignans

  2007cited by this paper
• Synthesis and Insecticidal Activity of Lignan Analogs (1)

  2006cited by this paper
• Cytotoxic arylnaphthalene lignans from Phyllanthus oligospermus.

  2006cited by this paper
• Progress on the chemistry of dibenzocyclooctadiene lignans.

  2005cited by this paper
• Synthesis and antiviral activity of helioxanthin analogues.

  2005cited by this paper
• Inhibition of Hepatitis B Virus Gene Expression and Replication by Helioxanthin and its Derivative

  2005cited by this paper
• Synthesis of medium-ring and iodinated biaryl compounds by organocuprate oxidation.

  2005cited by this paper
• A versatile stereoselective synthesis of endo,exo-furofuranones: application to the enantioselective synthesis of furofuran lignans.

  2004cited by this paper
• Two New Arylnaphthalide Lignans and Antiplatelet Constituents from Justicia procumbens

  2004cited by this paper
• Synthesis of Furofuran Lignans

  2004cited by this paper
• Diversity in lignan biosynthesis

  2004cited by this paper
• Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans.

  2004cited by this paper
• Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization.

  2003cited by this paper
• Phenylnaphthalene compounds from the subterranean part of Vitex rotundifolia and their antibacterial activity against methicillin-resistant Staphylococcus aureus.

  2001cited by this paper
• Antitumor agents. Synthesis and biological evaluation of new compounds related to podophyllotoxin, containing the 2,3-dihydro-1,4-benzodioxin system.

  2001cited by this paper
• Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans

  2000cited by this paper
• Synthesis and in vitro pharmacology of a series of new chiral histamine H3-receptor ligands: 2-(R and S)-Amino-3-(1H-imidazol-4(5)-yl)propyl ether derivatives.

  1999cited by this paper
• 1-Arylnaphthalene lignan: a novel scaffold for type 5 phosphodiesterase inhibitor.

  1999cited by this paper
• Six lignans from Phyllanthus myrtifolius.

  1996cited by this paper
• Antiplatelet arylnaphthalide lignans from Justicia procumbens.

  1996cited by this paper
• Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans.

  1996cited by this paper
• Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: structure-activity relationship study directed toward the improvement of metabolic stability.

  1996cited by this paper
• Differential inhibition of reverse transcriptase and cellular DNA polymerase-alpha activities by lignans isolated from Chinese herbs, Phyllanthus myrtifolius Moon, and tannins from Lonicera japonica Thunb and Castanopsis hystrix.

  1995cited by this paper
• Soybean phytoestrogen intake and cancer risk.

  1995cited by this paper
• Dietary soybean may be antiestrogenic in male mice.

  1995cited by this paper
• Lignans, neolignans, and related compounds.

  1995cited by this paper
• Urinary lignan and isoflavonoid excretion in men and women consuming vegetable and soy diets.

  1995cited by this paper
• Urinary lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder.

  1994cited by this paper
• Naphthalenic lignan lactones as selective, nonredox 5-lipoxygenase inhibitors. Synthesis and biological activity of (methoxyalkyl)thiazole and methoxytetrahydropyran hybrids.

  1994cited by this paper
• Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes.

  1994cited by this paper
• Justicidin E: A new leukotriene biosynthesis inhibitor.

  1993cited by this paper
• Lignans, neolignans, and related compounds.

  1993cited by this paper
• Anti-Oxidant Activity of Dibenzocyclooctene Lignans Isolated from Schisandraceae

  1992cited by this paper
• Synthesis and Insecticidal Activity of Haedoxan Analogs. Part IV. Effect on Insecticidal Activity of Substituents at the 1,4-Benzodioxanyl Moiety of Haedoxan.

  1992cited by this paper
• Magnolia virginiana Neolignan compounds as chemical barriers to swallowtail butterfly host use

  1992cited by this paper
• Influence on Insecticidal Activity of the 3-(3, 4-Methylenedioxyphenyl) Group in the 1, 4-Benzodioxanyl Moiety of Haedoxan

  1992cited by this paper
• Suppression of mitogen-induced proliferation of human peripheral blood lymphocytes by plant lignans.

  1991cited by this paper
• Synthesis and Insecticidal Activity of Lignan Analogs (II).

  1991cited by this paper
• A total synthesis of racemic paulownin using a type II photocyclization reaction

  1990cited by this paper
• Asymmetric total synthesis of (-)-podophyllotoxin

  1988cited by this paper
• Lignans, neolignans, and related compounds.

  1987cited by this paper
• Lignans and Neolignans

  1986cited by this paper
• Synthesis of lignan lactones by conjugate addition of thioacetal carbanions to butenolide

  1983cited by this paper
• Chirality transfer in stereoselective synthesis. A highly stereoselective synthesis of optically active vitamin E side chains

  1983cited by this paper
• Silafunctional compounds in organic synthesis. Part 20. Hydrogen peroxide oxidation of the silicon-carbon bond in organoalkoxysilanes

  1983cited by this paper
• Antitumor activity of Bursera schlechtendalii (burseraceae): isolation and structure determination of two new lignans.

  1972cited by this paper
• The chemistry of the lignan group of natural products

  1942cited by this paper

• Catalytic Asymmetric Total Synthesis of Schibitubin G and Revision of Its Absolute Configuration.

  2026cites this paper
• Dimerization of Allylbenzenes into Cyclolignans by a Metathesis-Oxidation Sequence.

  2026cites this paper
• Recent Advances in Cycloaddition Reactions of Donor-Acceptor Oxiranes via Carbon-Carbon Bond Cleavage.

  2025cites this paper
• Unified Asymmetric Synthesis of Aryltetralin Lactone Cyclolignans via Conformation-Assisted Radical C–H Cyclization

  2025cites this paper
• Integrative metabolomic and transcriptomic analyses reveal key mechanisms of lignan biosynthesis during sesame (Sesamum indicum L.) seed development

  2025cites this paper
• EXPLORING METABOLOMIC AND TRANSCRIPTOMIC INSIGHTS INTO LIGNAN BIOSYNTHESIS PATHWAYS IN POLYGONATUM SIBIRICUM AND POLYGONATUM KINGIANUM VAR. GRANDIFOLIUM

  2025cites this paper
• Hairy Roots as Producers of Coumarins, Lignans, and Xanthones

  2025cites this paper
• Total Synthesis of (-)-Steganacin via Stereocontrolled Atroposelective Intramolecular Mizoroki-Heck Reaction and Evaluation of Biological Activity.

  2025cites this paper
• Natural active botanical metabolites: targeting AMPK signaling pathway to treat metabolic dysfunction-associated fatty liver disease

  2025cites this paper
• Synthetic studies towards (–)-plicatic acid: A Ni-catalyzed reductive cyclization strategy for the construction of its aryltetralin framework

  2025cites this paper
• Comprehensive assessment of the nutritional, phytochemical, and volatile components present in the roots of Asparagus racemosus, an underutilized plant for food applications

  2025cites this paper
• Total Synthesis of the Furopyran Lignans Sumatranin A-D and the Proposed Structure of Sumatranin H.

  2025cites this paper
• Exploring Advances in Natural Plant Molecules for Allergic Rhinitis Immunomodulation in Vivo and in Vitro

  2025cites this paper
• Botany, traditional uses, phytochemistry, pharmacological activities, and toxicity of the mangrove plant Avicennia marina: a comprehensive review

  2025cites this paper
• Phytochemical Profile and Anticancer Potential of Helichrysum arenarium Extracts on Glioblastoma, Bladder Cancer, and Breast Cancer Cells

  2025cites this paper
• Efficient synthesis of dihydronaphthalenes via cerium-catalyzed annulation of 1-alkoxy substituted 1H-isochromenes with cinnamic acids.

  2025cites this paper
• The OsDIR55 gene increases salt tolerance by altering the root diffusion barrier.

  2024cites this paper
• Cyclolignan synthesis streamlined by enantioselective hydrogenation of tetrasubstituted olefins

  2024cites this paper
• Polyphenols and Functionalized Hydrogels for Osteoporotic Bone Regeneration

  2024cites this paper
• Unveiling the Power of Flax Lignans: From Plant Biosynthesis to Human Health Benefits

  2024cites this paper
• Recent advances in dietary polyphenols (DPs): antioxidant activities, nutrient interactions, delivery systems, and potential applications.

  2024cites this paper
• Therapeutic Potential of Resveratrol and Lignans in the Management of Tuberculosis

  2024cites this paper
• Total Syntheses and Absolute Stereochemical Correction of Negundin B, Vitexin 1, and Vitexin 6.

  2024cites this paper
• Intramolecular Ni-catalyzed reductive coupling enables enantiodivergent synthesis of linoxepin.

  2023cites this paper
• Novel lignans from Zanthoxylum nitidum and antiproliferation activity of sesaminone in osimertinib-resistant non-small cell lung cancer cells.

  2023cites this paper
• Recent developments in nickel-catalyzed asymmetric cyclization and cycloaddition of carbonyl-alkynes, cyano-alkynes, and enynes.

  2023cites this paper
• Acenaphthoimidazolylidene-Ligated Palladacycle Enabled Suzuki-Miyaura Cross-Coupling Employing Equimolar Organoboron for Tri-Ortho-Substituted Bi(hetero)aryls and Teraryls.

  2023cites this paper
• Synthesis of (±)-Phyltetralin by Cu/Pd-Catalyzed Arylboration

  2023cites this paper
• Antioxidant capacity of simplified oxygen heterocycles and proposed derivatives by theoretical calculations

  2023cites this paper
• Natural products as the calcium channel blockers for the treatment of arrhythmia: Advance and prospect.

  2023cites this paper
• Enhancing bioavailability of natural extracts for nutritional applications through dry powder inhalers (DPI) spray drying: technological advancements and future directions

  2023cites this paper
• Nutritional Value, Phytochemical Potential, and Biological Activities in Lentils (Lens Culinaris Medik.): A Review

  2023cites this paper
• Isolation, Identification, Anti-Inflammatory, and In Silico Analysis of New Lignans from the Resin of Ferula sinkiangensis

  2023cites this paper
• Dracocephalum moldavica L.: An updated comprehensive review of its botany, traditional uses, phytochemistry, pharmacology, and application aspects.

  2023cites this paper
• Divergent Total Syntheses of Gymnothelignan N, Beilschmin A, and Eupomatilones 1, 3, 4, and 7.

  2022cites this paper
• Plant Phenolics as Dietary Antioxidants: Insights on Their Biosynthesis, Sources, Health-Promoting Effects, Sustainable Production, and Effects on Lipid Oxidation

  2022cites this paper
• Antiviral, Anticancer and Hypotensive Potential of Diphyllin Glycosides and their Mechanisms of Action.

  2022cites this paper
• Rapid Assembly of Stereochemically Rich Polycyclic Tetrahydrofurans by a Conjugate Addition-Rh(II) Catalysis Sequence

  2022cites this paper
• Progress on Total Synthesis and Their Divergent Transformations of Aryltetrahydrofuran-type Lignans

  2022cites this paper
• Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities

  2022cites this paper
• A Concise Synthesis of Sacidumlignan B

  2022cites this paper
• Antioxidant, Anti-Inflammatory, Anti-Menopausal, and Anti-Cancer Effects of Lignans and Their Metabolites

  2022cites this paper
• Triflic‐Acid‐Catalyzed Tandem Epoxide Rearrangement and Annulation with Alkynes: An Efficient Approach for Regioselective Synthesis of Naphthalenes

  2022cites this paper
• Design, synthesis, and evaluation of cytotoxic activities of arylnaphthalene lignans and aza‐analogs

  2021cites this paper
• Diastereoselective Construction of Eight-Membered Carbocycles through Palladium-Catalyzed C(sp3)-H Functionalization.

  2021cites this paper
• Biological functions of lignans in plants

  2021cites this paper
• Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

  2021cites this paper
• Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions.

  2021cites this paper
• Synthesis of Lignans based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes.

  2021cites this paper
• Tandem UGT71B5s Catalyze Lignan Glycosylation in Isatis indigotica With Substrates Promiscuity

  2021influential citation
• Lignans of Sesame (Sesamum indicum L.): A Comprehensive Review

  2021cites this paper
• Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans

  2020cites this paper
• Melipatulinones A-C, Three Lignan-Phloroglucinol Hybrids from Melicope patulinervia.

  2020cites this paper
• A Review of Traditional Uses, Phytochemistry, and Pharmacological Properties of the Genus Saururus.

  2020cites this paper
• Diastereoselective Synthesis of 2,3,4-Trisubstituted Tetrahydrofurans via Thermally Reactive 1,5-Diene-tert-butyl Carbonates.

  2020cites this paper
• Patulignans A-C, three structurally unique lignans from the leaves of Melicope patulinervia.

  2020cites this paper
• HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes

  2020influential citation
• Syringaresinol Inhibits UVA-Induced MMP-1 Expression by Suppression of MAPK/AP-1 Signaling in HaCaT Keratinocytes and Human Dermal Fibroblasts

  2020cites this paper
• Recent Advances in the Total Synthesis of Natural Products Containing Eight-Membered Carbocycles (2009-2019).

  2020cites this paper
• A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

  2019cites this paper
• Lignans

  2019cites this paper
• Lignans in Diets

  2019cites this paper
• Cyclolignan Synthesis Streamlined by Enantioselective Hydrogenation of Tetrasubstituted Ole�ns

  year unknowninfluential citation