Small Molecule Wnt Pathway Modulators from Natural Sources: History, State of the Art and Perspectives
Abstract
:1. Introduction
1.1. Drugs from Natural Sources—A Brief Overview
1.2. Wnt Pathway and Its Biomedical Importance
2. Wnt Activators from Natural Sources
3. Wnt Inhibitors from Natural Sources
4. Discussion and Perspectives
Activators | ||||
Source organism | Acting substance | Mechanism/target | Reference | |
Plant | Plants (Indigo Naturalis, Isatis indigotica, Indigofera suffruticosa), mollusks (Nucella lapillus) and bacteria (Providencia, Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae) | Indirubin | Inhibits GSK3β and GSK3α | [45,47,48] |
Synthetic derivative 6-bromo-indirubin-3′-oxime (6BIO) | [45,46,49] | |||
Synthetic derivative indirubin-5-nitro-3′-oxime (INO) | [45,50] | |||
Andrographis paniculata | Andrographolide (labdane diterpenoid) | [45,51] | ||
Garcinia xanthochymus | Fukugetin (flavone) | [45,52] | ||
Ricinus communis | Ricinine (pyridone alkaloid) | Inhibits GSK3β and CK1 | [56] | |
Bauhinia championi | Polysaccharides | Overexpression of Wnt4, β-catenin, FZD2 and cyclin D and downregulation of GSK3β at both mRNA and protein levels | [76] | |
Cannabis sativa | Cannabidiol (phytocannabinoid) | [62] | ||
Salvia miltiorrhizae | Extract | [62] | ||
Siegesbeckia genus | Kirenol (diterpenoid) | [70] | ||
Guava fruit | Triterpene-enriched extract | Inhibits GSK3β | [71] | |
Ginkgo biloba | bilobalide (terpenic trilactone) | - | [68] | |
Ginkgolide B | - | [69] | ||
Extract | Increases β-catenin levels | [67] | ||
Rosmarinus officinalis, Lamiaceae, and Asteraceae family | Rosmarinic acid | [73] | ||
Curculigo orchioides | Curculigoside (phenolic glycoside) | [75] | ||
Euodia sutchuenensis | Extract | [66] | ||
Coptis chinensis | Berberine (alkaloid) | Increases total and nuclear β-catenin level | [86] | |
Cannabis sativa | Cannabidiol | Inhibits GSK3β and DKK1 | [80] | |
Achyranthes bidentata | Polysaccharide fraction | Increases nuclear β-catenin | [87] | |
Salvia miltiorrhizae | Salvianolic acid B | Inhibits GSK3β, increases nuclear β-catenin level | [63] | |
Dalbergia odorifera | 2,4,5-trimethoxyldalbergiquinol | [88] | ||
Morinda citrifolia | Extract | Inhibits GSK3β, increases β-catenin through PI3K/Akt | [72] | |
Vernonia anthelmintica | Flavonoids | Inhibits GSK3β through PI3K/Akt | [41] | |
Aconitum ciliare | Extract | β-catenin transcription | [78] | |
Soybeans | Genistein (isoflavonoid) | Inhibits GSK3β via ERK (increases nuclear β-catenin) | [83] | |
Rehmannia sp. | Extract | Downregulation of the Wnt inhibitors SOST and DKK, GSK3β phosphorylation | [61] | |
Sanguisorba officinalis | Extract | - | [57] | |
Hovenia dulcis | Methyl vanyllate | - | [43,58] | |
Sapindaceae family, Elaeagnaceae family | l-quebrachitol (2-O-methyl-l-chiro-inositol) (methoxy analog of inositol) | - | [60] | |
Epimedium wushanense | Flavonoids | - | [84] | |
Nicotiana tabacum | Extract of cigarette tobacco | - | [79] | |
Many plants | Calycosin | - | [85] | |
Algae | Undariopsis peterseniana | Extract | Increases of β-catenin accumulation and GSK3β phosphorylation | [98] |
Capsosiphon fulvescens | Polysaccharide fraction | Increases nuclear β-catenin level | [99] | |
Chlorella vulgaris | Extract | - | [100] | |
Marine rtebratesorganisms | Holothurian Molpadia musculus | Extract | - | [96] |
Polychaete Travisia sp. | Extract | - | [96] | |
Deep-sea anemone Phelliactis callicyclus | Extract | - | [96] | |
Oyster Crassostrea gigas | Extract | - | [97] | |
Fungi | Ganoderma lucidum | β-glucan | - | [215] |
Coriolus versicolor | Extract | - | [81] | |
Bacteria | Escherichia coli | Lipopolysaccharides | - | [77] |
Others | Plants, meat, milk, fungi | Alpha-lipoic acid | Downregulations of DKK1 and upregulation of LRP5 | [74] |
Synthetic derivative oxepanes | Binds Vangl1 and restores the signaling activity of DVL | [89] | ||
Inhibitors | ||||
Natural sources | Compound | Mechanism/Target | Reference | |
Plants | Syzygium guineense | Tannins | Destabilize Wnt proteins | [187] |
different vegetable oils | γ-Tocotrienol (vitamin e) | Inductions of expression of DKK1 | [166,167] | |
Mallotus philippensis | Rottlerin (polyphenol) | Suppresses expression and phosphorylation of LRP6 | [174] | |
genus Magnolia | Honokiol (lignan) | Increases expression CK1α and GSK3β | [168] | |
Lonicera japonica | Hydnocarpin (lignan) | Increases cytoplasmic levels of Axin | [169] | |
Solanaceae family | Analogs of withanolides (steroids) | Stabilize Axin | [208] | |
Scutellaria barbata | Extract | Reduces Wnt target genes and β-catenin | [162] | |
Berberis vulgaris | Berberine (alkaloid) and its synthetic 13-arylalkyl derivatives | Reduces β-catenin | [161] | |
Orchidaceae family | Gigantol (alkaloid) | Reduces phosphorylated LRP6, total LRP6 and cytoplasmic β-catenin | [165] | |
Saussurea lappa | Dehydrocostus lactone | Arrests β-catenin translocation to nucleus | [175] | |
Costunolide | ||||
Leuconotis griffithii | Bisleuconothine A (alkaloid) | Promotes phosphorylation of β-catenin and inhibits its nuclear translocation | [176] | |
Tabernaemontana divaricata | Coronaridine (alkaloid) | Decreases β-catenin mRNA | [180] | |
Ocimum sanctum | Vicenin-2 (flavonoid) | Decreases β-catenin | [181] | |
Cephalotaxus fortunei | Ginkgetin (biflavone) | - | [150] | |
Green and black tea, fruits, vegetables | Quercetin (flavonoid) | Suppresses binding within the TCF-based transcription factor complexes | [103,104,105,106,107] | |
Isoquercetin (flavonoid) | [111] | |||
EGCG ((−)−epigallocatechin-3-gallate) (flavonoid) | - | [183] | ||
Gallic acid | Increases GSK3β and p-β-catenin | [184] | ||
Grapes, wine, cacao, hazelnuts | Resveratrol (stilbene) | Downregulates TCF4 by interacting with relevant microRNAs | [134,142,143] | |
Curcuma longa | Curcumin (flavonoid) | Decreases the levels of TCF4, CBP and p300, reduces nuclear β-catenin | [115,116,117,130,131,132] | |
Demethoxycurcumin | Downregulates p300 by interacting with relevant microRNAs | [117] | ||
Bisdemethoxycurcumin | ||||
Tetrahydrocurcumin | ||||
Curcuma zedoaria | β-elemene (sesquiterpene) | Decreases β-catenin and TCF7 | [164] | |
Cruciferae family | 1-Benzyl-indole-3-carbinol (synthetic analogue of the natural phytochemical indole-3-carbinol) | Increases GSK3β and Axin, decreases β-catenin | [185] | |
Periploca sepium | Periplocin (cardiac glycoside) | Reduces binding of TCF complex to specific DNA binding site | [147] | |
Telectadium dongnaiense | - | [160] | ||
Isodon rubescens var. lushanensis | Henryin (diterpenoid) | Impairs association of β-catenin/TCF4 transcriptional complex | [148] | |
Tanacetum parthenium | Parthenolide (sesquiterpene) | Synthesis TCF4/LEF1 | [182] | |
Gossypium genus | Gossypol (polyphenol) | Inhibitor of MSI1 | [153] | |
Gossypolone | - | [154] | ||
Matricaria recutita, tanacetum parthenium, citrus | Apigenin (flavonoid) | Regulatory microRNAs | [155] | |
Sanguis Draxonis | Loureirin B (flavonoid) | Upregulates miR-148-3p | [156] | |
Artemisia annua | Dihydroartemisinin | Increases phosphorylated β-catenin | [157] [158] | |
Malus pumila Miller cv. ‘Annurca’ | Extract | - | [163] | |
Malus domestica cv ‘Limoncella’ | Extract | - | ||
Mangifera indica | Mangiferin | Downregulates the LEF1 coactivator protein WT1 | [149] | |
Rehmannia glutinosa | Glycoside fraction | - | [64] | |
Salvia miltiorrhizae | Dihydrotanshinone | - | [65] | |
Helianthus tuberosus | Extract | - | [159] | |
Ampelopsis japonica | Extract | - | ||
Gynura divaricata | Extract | - | [171] | |
Oryza sativa (rice) | extract | Upregulates CK1 | [172] | |
Inositol hexaphosphate | - | [173] | ||
Many plants | Cardamonin | Inhibits the deactivating phosphorylation of GSK3β by Akt | [151] | |
Bocquillonia nervosa | 12-deoxyphorbol esters | - | [152] | |
Neoguillauminia cleopatra | ||||
Euphorbia dracunculoides | Tigliane (diterpenoids) | - | [177] | |
Euphorbia croton tiglium | PMA (diterpene ester) | PKCα (cross-talk with Wnt pathway) | [179] | |
Euphorbia peplus | PEP005 (diterpene ester) | PKCα (cross-talk with Wnt pathway) | [179] | |
Citrus bergamia (bergamot) | Brutieridin and Melitidin | - | [170] | |
Plants: rhubarb, buckthorn and Japanese knotweed (Reynoutria japonica) Fungi: Aspergillus, Pyrenochaeta and Pestalotiopsis | Emodin (anthraquinone) | Interacts with TCF/LEF, downregulates p300, upregulates the repressor HBP | [146] | |
Polygonum cuspidatum | 2-methoxystypandrone | Targets β-catenin destruction complex, decreases β-catenin | [186] | |
Solanaceae family | Synthetic derivatives of withanolides | Stabilize Axin | [208] | |
Lichens (Platismatia glauca, Cladonia uncialis, Parmelia sulcata, Hypogymnia physodes, and Hypocenomyce scalaris) | Caperatic acid | - | [199] | |
Lichens | Lichens (Platismatia glauca, Cladonia uncialis, Parmelia sulcata, Hypogymnia physodes, and Hypocenomyce scalaris) | Physodic acid | - | [199,210,211] |
Synthetic riminophenazine derivative: Clofazimine | - | |||
Penicillium vulpinum | Patulin (mycotoxin) polyketide | - | [188] | |
Fungi | Penicillium sp. sh18 | Isopenicin (meroterpenoid) | - | [189] |
Streptomyces griseolus | Anisomycin (antibiotic) | Decreases β-catenin | [190] | |
Ganoderma lucidum | Extract | Inhibits phosphorylation of LRP6 | [192] | |
Metarhizium anisopliae | Destruxin B (mycotoxin) cyclodepsipeptide | Downregulates β-catenin and TCF4 and β-catenin/TCF4 transcriptional activity | [193,194] | |
Cordyceps sinensis | Cordycepin (3′-deoxyadenosine) | Stimulates adenosine A3 receptors | [195] | |
Streptomyces griseus | Bafilomycin (antibiotic) | Acts upstream of GSK3β | [196] | |
Neosartorya pseudofischeri | Gliotoxin | Degradations of β-catenin | [191] | |
Inonotus obliquus | Ergosterol peroxide (Steroid) | Decreases nuclear β-catenin | [197] | |
Inonotus obliquus Actinomycetes species | Inotodiol (lanostane triterpenoid) | Decreases nuclear β-catenin Inhibits TCF/β-catenin transcriptional activity | [198] | |
Bioactive secondary metabolites of aromatic and heterocyclic nature | [200] | |||
Bacteria | marine actinomycetes (CKK1019 strain) | chromomycins A2 and A3 | - | [201] |
Marine sponge | Smenospongidine (sesquiterpenoid quinone) | Promotes the proteasomal degradation of intracellular β-catenin | [204] | |
Marine organisms | Marine sponge Holothuria Peniagone sp. | Aeroplysinin-1 (brominated tyrosine) | Promotes the proteasomal degradation of intracellular β-catenin - | [205] |
Sesterterpenoid and Steroid Metabolites | [206] | |||
Quinones | - | [207] | ||
Extract | - | [96] | ||
Holothuria Molpadia musculus | Extract | - | [96,202] | |
Crustacean Calocarides quinqueseriatus | Extract | - | ||
Crustacean Munidopsis antonii | Extract | - | ||
Brittle star Ophiura irrorata | Extract | - | ||
Toads | Telocinobufagin (Bufadienolides) | Phosphorylation of GSK3β | ||
Others | Buthus martensi | Peptide rBMK AGAP | Decreases β-catenin and p-GSK3β | [203] |
Funding
Conflicts of Interest
References
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Blagodatski, A.; Klimenko, A.; Jia, L.; Katanaev, V.L. Small Molecule Wnt Pathway Modulators from Natural Sources: History, State of the Art and Perspectives. Cells 2020, 9, 589. https://doi.org/10.3390/cells9030589
Blagodatski A, Klimenko A, Jia L, Katanaev VL. Small Molecule Wnt Pathway Modulators from Natural Sources: History, State of the Art and Perspectives. Cells. 2020; 9(3):589. https://doi.org/10.3390/cells9030589
Chicago/Turabian StyleBlagodatski, Artem, Antonina Klimenko, Lee Jia, and Vladimir L. Katanaev. 2020. "Small Molecule Wnt Pathway Modulators from Natural Sources: History, State of the Art and Perspectives" Cells 9, no. 3: 589. https://doi.org/10.3390/cells9030589