Convergent evolution of plant specialized 1,4-naphthoquinones: metabolism, trafficking, and resistance to their allelopathic effects

We highlight how recent discoveries have revealed insight into the evolution of plant specialized 1,4-naphthoquinone metabolism and trafficking, and offer a perspective for investigating mechanisms plants use to tolerate allelopathic 1,4-naphthoquinones.

• Publication year

  2020

• Venue

  Journal of Experimental Botany

• Publication date

  2020-12-01

• Fields of study

  Biology, Medicine, Environmental Science

• Identifiers
  DOI 10.1093/jxb/eraa462PMID 33258472PMCID 7853596
• 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.

• Discovery and engineering of colchicine alkaloid biosynthesis

  2020cited by this paper
• Potential role of two cytochrome P450s obtained from Lithospermum erythrorhizon in catalyzing the oxidation of geranylhydroquinone during Shikonin biosynthesis.

  2020cited by this paper
• Effects of (±)-dunnione and quinone-containing extracts from in vitro-cultured plantlets of Streptocarpus dunnii Hook. f. and a hybrid ‘Ruby’ on seed germination

  2020cited by this paper
• Advances in biosynthesis, regulation, and metabolic engineering of plant specialized terpenoids.

  2020cited by this paper
• A Cytosol-Localized Geranyl Diphosphate Synthase from Lithospermum erythrorhizon and Its Molecular Evolution1[OPEN]

  2020cited by this paper
• Comparative genome/transcriptome analysis probes Boraginales' phylogenetic position, WGDs in Boraginales, and key enzyme genes in the alkannin/shikonin core pathway

  2020cited by this paper
• Quinone perception in plants via leucine-rich-repeat receptor-like kinases

  2020cited by this paper
• Hybrid de novo genome assembly of red gromwell (Lithospermum erythrorhizon) reveals evolutionary insight into shikonin biosynthesis

  2020cited by this paper
• Mechanisms of evolved herbicide resistance

  2020cited by this paper
• Hybrid de novo genome assembly of red gromwell (Lithospermum erythrorhizon) reveals evolutionary insight into shikonin biosynthesis.

  2020cited by this paper
• Specialized naphthoquinones present in Impatiens glandulifera nectaries inhibit the growth of fungal nectar microbes

  2019cited by this paper
• The renaissance of comparative biochemistry.

  2019cited by this paper
• Sequencing a Juglans regia × J. microcarpa hybrid yields high-quality genome assemblies of parental species

  2019cited by this paper
• Lygodium japonicum (Thunb.) Sw

  2019cited by this paper
• Synthesis, biological function and evaluation of Shikonin in cancer therapy.

  2019cited by this paper
• The origin and biosynthesis of the naphthalenoid moiety of juglone in black walnut

  2018cited by this paper
• Genomic Variation Among and Within Six Juglans Species

  2018cited by this paper
• Involvement of LeMRP, an ATP-binding cassette transporter, in shikonin transport and biosynthesis in Lithospermum erythrorhizon.

  2018cited by this paper
• Beyond Defense: Multiple Functions of Benzoxazinoids in Maize Metabolism.

  2018cited by this paper
• Biosynthesis of redox-active metabolites in response to iron deficiency in plants

  2018influential reference
• Influence of lipophilicity in O-acyl and O-alkyl derivatives of juglone and lawsone: a structure-activity relationship study in the search for natural herbicide models.

  2018cited by this paper
• Trichomes and naphthoquinones protect Streptocarpus dunnii Hook.f. against environmental stresses

  2018cited by this paper
• CYP76B74 Catalyzes the 3′′-Hydroxylation of Geranylhydroquinone in Shikonin Biosynthesis1

  2018cited by this paper
• Contribution of isopentenyl phosphate to plant terpenoid metabolism

  2018cited by this paper
• Involvement of LeMDR, an ATP-binding cassette protein gene, in shikonin transport and biosynthesis in Lithospermum erythrorhizon

  2017cited by this paper
• Naphthalene glycosides in the Thai medicinal plant Diospyros mollis

  2017cited by this paper
• Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.: E. plantagineum and E. gaditanum.

  2017cited by this paper
• General Introduction to Glucosinolates

  2016cited by this paper
• The walnut (Juglans regia) genome sequence reveals diversity in genes coding for the biosynthesis of non-structural polyphenols.

  2016cited by this paper
• Convergent evolution of caffeine in plants by co-option of exapted ancestral enzymes

  2016cited by this paper
• From low- to high-potential bioenergetic chains: Thermodynamic constraints of Q-cycle function.

  2016influential reference
• Biosynthesis and molecular actions of specialized 1,4-naphthoquinone natural products produced by horticultural plants

  2016cited by this paper
• Characterization of Shikonin Derivative Secretion in Lithospermum erythrorhizon Hairy Roots as a Model of Lipid-Soluble Metabolite Secretion from Plants

  2016cited by this paper
• Plastoquinone and Ubiquinone in Plants: Biosynthesis, Physiological Function and Metabolic Engineering

  2016cited by this paper
• Dissecting the mechanism of Solanum lycopersicum and Solanum chilense flower colour formation.

  2015cited by this paper
• Rethinking how volatiles are released from plant cells.

  2015cited by this paper
• Synteny analysis in Rosids with a walnut physical map reveals slow genome evolution in long-lived woody perennials

  2015cited by this paper
• Hydroxycinnamic Acid Degradation, a Broadly Conserved Trait, Protects Ralstonia solanacearum from Chemical Plant Defenses and Contributes to Root Colonization and Virulence.

  2015cited by this paper
• Soil hypha‐mediated movement of allelochemicals: arbuscular mycorrhizae extend the bioactive zone of juglone

  2014cited by this paper
• A familiar ring to it: biosynthesis of plant benzoic acids.

  2014cited by this paper
• Inhibitory Potential of Naphthoquinones Leached from Leaves and Exuded from Roots of the Invasive Plant Impatiens glandulifera

  2014cited by this paper
• Arbuscular mycorrhizal fungal hyphae enhance transport of the allelochemical juglone in the field

  2014cited by this paper
• Cellular responses to naphthoquinones: juglone as a case study

  2014cited by this paper
• 1,4-Naphthoquinones: From Oxidative Damage to Cellular and Inter-Cellular Signaling

  2014cited by this paper
• Natural Compounds as Next-Generation Herbicides

  2014cited by this paper
• Bioactive Naphthoquinones from Higher Plants

  2014cited by this paper
• Chemopreventive Activities of Shikonin in Breast Cancer

  2014cited by this paper
• Biosynthesis, function and metabolic engineering of plant volatile organic compounds.

  2013cited by this paper
• On the universal core of bioenergetics.

  2013cited by this paper
• Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

  2013cited by this paper
• Network analysis of the MVA and MEP pathways for isoprenoid synthesis.

  2013cited by this paper
• Coupling deep transcriptome analysis with untargeted metabolic profiling in Ophiorrhiza pumila to further the understanding of the biosynthesis of the anti-cancer alkaloid camptothecin and anthraquinones.

  2013cited by this paper
• Bioactive styryllactones, two new naphthoquinones and one new styryllactone, and other constituents from Goniothalamus scortechinii

  2012cited by this paper
• Gene network reconstruction identifies the authentic trans-prenyl diphosphate synthase that makes the solanesyl moiety of ubiquinone-9 in Arabidopsis.

  2012cited by this paper
• Vitamin K1 (Phylloquinone): Function, Enzymes and Genes

  2011cited by this paper
• Enhanced plumbagin production in elicited Plumbago indica hairy root cultures.

  2011cited by this paper
• Ability of the Oriental Fruit Moth Grapholita molesta (Lepidoptera: Tortricidae) to Detoxify Juglone, the Main Secondary Metabolite of the Non-host Plant Walnut

  2011cited by this paper
• Evolution of photosynthesis.

  2011cited by this paper
• How the oligophage codling moth Cydia pomonella survives on walnut despite its secondary metabolite juglone.

  2011cited by this paper
• Convergent evolution in plant specialized metabolism.

  2011cited by this paper
• New naphthoquinone from the root of Lygodium japonicum (Thunb.) Sw.

  2010cited by this paper
• Phenylpropanoid biosynthesis.

  2010cited by this paper
• 5-Hydroxy-1,4-naphthoquinone (juglone) and 2-hydroxy-1,4-naphthoquinone (lawsone) influence on jack bean urease activity: Elucidation of the difference in inhibition activity.

  2010influential reference
• Detoxification without Intoxication: Herbicide Safeners Activate Plant Defense Gene Expression1[C]

  2010cited by this paper
• Alkaloid biosynthesis: metabolism and trafficking.

  2008cited by this paper
• How plants cope with foreign compounds. Translocation of xenobiotic glutathione conjugates in roots of barley (Hordeum vulgare).

  2007cited by this paper
• How Plants Cope with Foreign Compounds. Translocation of xenobiotic glutathione conjugates in roots of barley (Hordeum vulgare) (9 pp)

  2007cited by this paper
• Metabolism-based herbicide resistance: regulationby safeners

  2004cited by this paper
• Genetics and biochemistry of secondary metabolites in plants: an evolutionary perspective.

  2000cited by this paper
• Fungal Resistance to Plant Antibiotics as a Mechanism of Pathogenesis

  1999cited by this paper
• Insight into naphthoquinone metabolism: beta-glucosidase-catalysed hydrolysis of hydrojuglone beta-D-glucopyranoside.

  1998cited by this paper
• Inhibition and regulation of shikonin biosynthesis in suspension cultures of Lithospermum

  1996cited by this paper
• Naphthohydroquinone glucosides of Drosera rotundifolia and D. intermedia from in vitro cultures

  1996cited by this paper
• Levels of a Hydrojuglone Glucoside in Developing Pecan Leaves in Relation to Scab Susceptibility

  1994cited by this paper
• Different Mode of Incorporation of o-Succinylbenzoic Acid into the Naphthoquinones Juglone and Lawsone in Higher Plants

  1994cited by this paper
• Evidence that stilbene synthases have developed from chalcone synthases several times in the course of evolution

  1994cited by this paper
• Degradation of juglone by soil bacteria

  1988cited by this paper
• Quinonoid and other constituents of Aristea ecklonii

  1985cited by this paper
• Distribution of juglone and related compounds in pecan and their effect on Fusicladium effusam.

  1980cited by this paper
• Metabolic relation between naphthalene derivatives in Juglans

  1978cited by this paper
• p-hydroxybenzoic acid and mevalonic acid as precursors of the plant naphthoquinone alkannin.

  1971cited by this paper
• Notizen: On the mode of incorporation of shikimic acid into 2-hydroxy-1,4-naphthoquinone (lawsone)

  1967cited by this paper

• Pollination versus carnivory: functional distribution of naphthoquinones in Nepenthes khasiana

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• Metabolic and Physiological Coordination of Drought Response and Recovery in Porlieria chilensis

  2026cites this paper
• Allelopathic compound 2-methoxy-1,4-naphthoquinone is broadly effective against pathogenic Prototheca species in vitro and in vivo

  2025cites this paper
• Naphthoquinones Isolated from Fusarium solani, an Endophytic Fungi of Cola nitida, with Potentials for Pharmaceutical and Industrial Applications

  2025cites this paper
• Visible Light and Hypervalent Iodine‐Induced C(sp2)H Difunctionalization: Metal‐Free Dual Synthetic Approach for Carboaminated Naphthoquinones

  2025cites this paper
• Extracellular respiration is a latent energy metabolism in Escherichia coli.

  2025cites this paper
• Shikonin-induced secondary metabolite modulation in grape berries (Vitis vinifera L. cv. ‘Öküzgözü’) under salinity stress

  2025cites this paper
• Impatiens glandulifera Royle: From ecological threat to biotechnological opportunity - A narrative review.

  2025cites this paper
• Distribution of Acetogenic Naphthoquinones in Droseraceae and Their Chemotaxonomic Utility

  2024cites this paper
• Quinone scaffolds as potential therapeutic anticancer agents: Chemistry, mechanism of Actions, Structure-Activity relationships and future perspectives

  2024cites this paper
• A Prenyltransferase Participates in the Biosynthesis of Anthraquinones in Rubia cordifolia.

  2024cites this paper
• Riparian invader: A secondary metabolite of Impatiens glandulifera impairs the development of the freshwater invertebrate key species Chironomus riparius

  2024cites this paper
• Lawsone Unleashed: A Comprehensive Review on Chemistry, Biosynthesis, and Therapeutic Potentials

  2024cites this paper
• Mechanism of action of the toxic proline mimic azetidine 2-carboxylic acid in plants.

  2024cites this paper
• Strategies to study the metabolic origins of specialized plant metabolites: The specialized 1,4-naphthoquinones.

  2023cites this paper
• Impact of cytotoxic plant naphthoquinones, juglone, plumbagin, lawsone and 2-methoxy-1,4-naphthoquinone, on Chlamydomonas reinhardtii reveals the biochemical mechanism of juglone toxicity by rapid depletion of plastoquinol.

  2023cites this paper
• Carnivorous Plants from Nepenthaceae and Droseraceae as a Source of Secondary Metabolites

  2023cites this paper
• A comparative investigation of catalytic mechanism and domain between catechol-O-methyltransferase isoforms by isomeric shikonin and alkannin.

  2023cites this paper
• The Discovery and Characterization of 1,4-Dihydroxy-2-naphthoic Acid Prenyltransferase Involved in the Biosynthesis of Anthraquinones in Rubia cordifolia

  2023cites this paper
• Ethnobotany, Pharmacology and Major Bioactive Metabolites from Impatiens Genus Plants and their Related Applications

  2023cites this paper
• Quinones as Promising Compounds against Respiratory Viruses: A Review

  2023cites this paper
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  2023cites this paper
• Resource efficiency and environmental impact of juglone in Pericarpium Juglandis: A review

  2022cites this paper
• Genomic insights into the evolution of plant chemical defense.

  2022cites this paper
• Allelopathy as an evolutionary game

  2022cites this paper
• Allelopathy as an evolutionarily stable strategy

  2021cites this paper
• Integrative analysis of the shikonin metabolic network identifies new gene connections and reveals evolutionary insight into shikonin biosynthesis

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