Nitric Oxide as a Target for Phytochemicals in Anti-Neuroinflammatory Prevention Therapy
Abstract
:1. Introduction
1.1. The role of NO in Various Neurological Disorders
Stimulator | Cell Type | References |
---|---|---|
LPS | Murine microglia (BV2), primary microglia, and RAW cells | [49,50] |
TNF-α | Macrophages | [51] |
IL-1β | Murine N9 microglia | [52] |
Estrogen | Human umbilical vein cells (HUVEC) and human neuroblastoma cells (SK-N-SH) | [53] |
IFN-γ | Macrophages | [51] |
Hypoxia | Rat insulinoma cell line (INS-1), rat islet cells | [54] |
Ethanol | Hypothalamic neuronal cell cultures | [55] |
Advanced glycation end products | BV2 cells, endothelial cells | [56] |
1.2. Anti-Neuroinflammatory and NO-Inhibiting Activity of Lignans and Neolignans
1.3. Anti-Neuroinflammatory and NO-Inhibiting Effects of Flavonoids
1.4. Anti-Neuroinflammatory and NO-Inhibiting Activity of Polyphenols
1.5. Anti-Neuroinflammatory and NO-Inhibiting Activity of Triterpenoids
1.6. Anti-Neuroinflammatory and NO-Inhibiting Activity of Phytoestrogens
1.7. Anti-Neuroinflammatory and NO-Inhibiting Activity of Coumarins
1.8. Anti-Inflammatory and NO-Inhibiting Activity of other Compounds
Scientific Name | Compound | IC50 | Class | Pharmacological Target | Pharmacological Effects | References |
---|---|---|---|---|---|---|
Abies holophylla | Holophyllane A | 12.75 | Triterpenoid | NO | Anti-inflammatory Anticancer | [89] |
Holophyllane B | 18.96 | |||||
Artemisia argyi | Sesquiterpene dimer | NA | Terpenoid | NO, PGE2, TNF-α, IL-1β, GM-CSF, MIP-1α, p38 MAPKs., JNK, JAK2/STAT3 | Anti-inflammation Anticancer Antioxidant Antidiabetic | [93] |
Artemisia asiatica | Eupatilin | NA | Flavone | NF-κB | Anti-inflammatory Neuroprotective | [68] |
Betula schmidtii | 2α-O-benzoyl-3β,19α-dihydroxy-urs-12-en-28-oic acid | 4.92 | Triterpenoids | NO | Anti-inflammatory | [86,102] |
2α-O-benzoyl-19α-hydroxy-3-oxo-urs-12-en-28-oic acid | 9.68 | |||||
Corosolic acid 11-Oxo-erythrodiol | 12.93 16.58 | NO | ||||
Maslinic acid | 4.46 | TNF-α, NF-κB, a COX-2, NO | ||||
Morolic acid 3-O-caffeate | 8.62 | |||||
Ambradiolic acid | ||||||
Isotachioside 4-allyl-2-hydrophenyl 1-O-β- | 23.9 | Phenolic derivatives | ||||
D-apiosyl-(1 → 6)- β -D-glucopyranoside | 25.3 | |||||
Genistein 5-O-β-D-glucoside | 28.8 | |||||
Prunetinoside | 34.0 | |||||
Brassica olifera | Sulforaphane | 5.85 | isothiocyanate | Anti-inflammatory Antioxidant Anti-amnesic Neuroprotective | [56,103,104] | |
Bupleurum falcatum | Saikosaponins | NA | Terpenoid | NO, TNF-α, IL-6, IL-1β, iNOS, NF-κB |
Immune modulator Antibacterial Anti-inflammatory Antihepatoma | [92] |
Capsella Bursa-pastoris | Sesquilignan glycoside | 75.13 | Phenolic glycosides | Anti-inflammatory | [105] | |
7S, 8R, 8′R-(−)-lariciresinol-4,4′-bis-O-glucopyranoside | 48.80 | |||||
Lariciresinol4′-O-β-d-glucoside | 30.70 | |||||
(+)-Pinoresinol-β-d-glucoside | 17.80 | |||||
Salidroside | 31.14 | |||||
3-(4-β-D-glucopyranosyloxy-3,5-dimethoxy)-phenyl-2E-propanol | 62.21 | |||||
β-Hydroxy-propiovanillone 3-O-β-d-glucopyranoside | 27.91 | |||||
Coniferin | 49.21 | |||||
Chaenomeles sinensis | 3β-O-cis-feruloyl-2α,19α- dihydroxyurs-12-en-28-oic acid | 37.1 | Triterpenoids | NO | Anti-inflammatory | [106] |
Maslinic acid | 17.8 | |||||
2α,3α-Dihydroxyolean-12-en-28-oic acid | 21.6 | |||||
2α-Hydroxyursolic acid | 47.1 | |||||
Betulinic acid | 4.5 | NF-κB, NO, prostaglandin E2, TNF-α, IL-1β, IL-6, COX-2 | ||||
Alphitolic acid | 14.5 | |||||
3-O-cis-caffeoylbetulinic | 13.4 | |||||
Ilekudinol C | 25.5 | |||||
Chaenomin | 48.37 | |||||
Berbekorin A | 49.29 | |||||
Aucuparin | 50.15 | NO | ||||
2′-Hydroxyaucuparin | 38.06 | |||||
2′-Methoxyaucuparin | 28.09 | |||||
2′,4′-Dimethoxyaucuparin | 39.64 | |||||
ε-Cotonefuran | 17.78 | NO | ||||
Chaenomeles speciosa | Chaenomin B | 283.33 | Biphenyl derivatives | Anticancer Anti-inflammatory Neuroprotective | [88] | |
Chaenomin A | 86.02 | |||||
2′,4′-Dimethoxyaucuparin | 272.72 | |||||
Aucuparin | 20.04 | |||||
2′-Methoxyaucuparin | 22.02 | |||||
Maslinic acid | 26.96 | |||||
Dihydrotomentosolic acid | 19.41 | |||||
Ilexgenin B, | 12.72 | |||||
Betulinic acid | 2.38 | NF-κB, NO, prostaglandin E2, TNF-α, IL-1β, IL-6, COX-2 | ||||
23-Hydroxybetulinic acid and pycarenic acid | 6.70 | |||||
Pycarenic acid | 67.50 | |||||
Citrus aurantium | Tangeretin | NA | Flavone | Anti-neuroinflammatory | [73] | |
Citrus unshiu | Citrusin XI | 70 | Cyclopeptide | NO, iNOS, NF-κB | Anti-inflammatory Anti-fungal Anti-bacterial Antioxidant | [98] |
Clematis armandii | (7R, 8S)-dehydrodiconferyl alcohol | 9.3 | Lignan | NO, COX-2, iNOS, NF-κB, AKT, JNK, src, fak | Anti-aging Anti-inflammatory | [59,60] |
Cudrania tricuspidata Bureau | Cudraflavanone A | 22.2 | Flavonoid | NO, PGE2, iNOS, NF-κB, P38, JNK MAPK | Anti-inflammatory Neuroprotective Antioxidant | [64] |
Dioscorea nipponica | Tsaokarylone | 13.36 | Phenols | NO | Anti-diabetic Anti-inflammatory | [75] |
(4E,6E)-1-(3ʹ,4ʹ-dihydroxyphenyl)-7-(4ʹʹ-hydroxyphenyl)-hepta-4, 6-dien-3-one | 14.36 | |||||
Firmiana simplex | 4-[(1S,2R)-1,3-dihydroxy-2-[4-[(1E)-3-hydroxy-1-propenyl]-2- methoxyphenoxy] propyl]-2-methoxyphenyl β-D-glucopyranoside | 59.83 | Lignan glycosides | NO, PGE2, TNF-α, IL-1β, COX2, MAPKs, ERK, JNK, p38 MAPK | Anti-neuroinflammatory Anti-inflammatory Neuroprotective | [107] |
Balanophonin | 10.25 | Neolignan derivative | [57] | |||
Firmianols A | 35.39 | Lignan derivatives | ||||
Firmianols B | >500 | |||||
(+)-Piperitol | 32.65 | |||||
(+)-Pinoresinol | 25.1 | |||||
(+)-Syringaresinol | 27.53 | |||||
Buddlenol E | 19.22 | |||||
(+)-Sesamin | 26.26 | |||||
(−)-Pinoresinol | 31.1 | |||||
(+)-7′-Methoxylariciresinol | 32.99 | |||||
(−)-5-Methoxybalanophonin | 10.0 | |||||
Buddlenol A Threo-(7R,8R)- | 15.23 | |||||
Guaiacylglycerol-β-coniferyl aldehyde ether | 1.05 | |||||
Erythro-(7S,8R)-Guaiacylglycerol-β-coniferyl aldehyde ether | 0.929 | |||||
Threo-Guaiacylglycerol-8-O-4′-sinapyl alcohol ether | 9.14 | |||||
Erythro-Syringylglycerol-8-O-4′-coniferyl alcohol ether | 9.14 | |||||
Threo-Guaiacylglycerol-8-O-4′-coniferyl alcohol ether | 32.56 | |||||
Threo-Guaiacylglycerol 8′-vanillin ether | 47.59 | |||||
Fraxinus rhynchophylla | Oleuropein | NO, ROS, ERK/p38/NF-κB | [77] | |||
Glycine max | Daidzein | 93.15 | Isoflavones | NO, AMP kinase, NF-κB | Anti-inflammatory Neuroprotective | [65] |
Daidzein | 14.09 | |||||
Genistein | 137.50 | |||||
Genistein | 10.63 | |||||
Equol | 3.45 | |||||
Impatiens balsamina | Balsamisides A | 33.33 | Biflavonoid glycosides | NO | Anti-neurodegenerative | [71] |
Balsamisides B | 56.86 | |||||
Balsamisides C | 39.16 | |||||
Balsamisides D | 31.02 | |||||
Kaempferol | 8.86 | |||||
Kaempferol 3-O-β-D-glucopyranoside, | 23.50 | |||||
Kaempferol3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside | 31.73 | |||||
Kaempferol3-O-α-L-rhamnopyranosyl-(1→6)-β-Dglucopyranoside | 44.44 | |||||
Kaempferol 3-O-β-D-allopyranoside | 80.35 19.11 | |||||
Quercetin | 19.11 | |||||
Quercetin3-O-β-D-glucospyranoide, | 55.59 | |||||
Quercetin3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside | 24.29 | |||||
Dihydromyricetin | 32.66 | |||||
Lagerstroemia indica | Pterospermin A | 21.4 | Phenolic derivative | Anti-inflammatory | [108] | |
Dihydrodehydroconiferyl alcohol | 14.6 | |||||
Alatusol | 35.4 | |||||
Ficusol | 36.0 | |||||
Evofolin-B | 22.0 | |||||
Marphenol | 44.9 | |||||
Ligustrum obtusifolium | Obtusifolisides A | 33.85 | Secoiridoid glycosides | LPS-activated microglia neuroinflammation | [109] | |
Obtusifolisides B | 5.45 | |||||
Oleoside-11-methylester | 38.67 | |||||
Oleoside-7,11-dimethylester 10-Hydroxyoleuropein | 38.89 11.17 | |||||
Oleuropein | 14.62 | |||||
Ligstroside | 61.25 | |||||
(2″R)-2″- methoxyoleuropein | 15.45 | |||||
Neonuezhenide | 14.96 | |||||
4,4′-(1E,1′E,3E,3′E)-3,3′-(hydrazine-1,2-diylidene) bis-(prop-1-ene-1-yl-3-ylidene) bis-(2-methoxyphenol) | 12.47 | Azine derivative | [110] | |||
Lindera glauca | Eudeglaucone | 15.90 | Eudesmane sesquiterpene | Anti-inflammatory | [87,111] | |
(+)-Faurinone | 3.67 | |||||
3α-Hydroxycostic acid | 26.48 | |||||
Ilicic acid | 14.92 | |||||
γ-Costic acid | 24.44 | |||||
Costic acid | 12.13 | |||||
Lindera neesiana | Koaburaside | NA | Phenolic glycoside | NO, MAPK, COX-2, INOS | Anti-inflammatory, Neuroprotection | [99] |
Medicago sativa Linn | Coumestrol | NA | Phytoestrogen | NO, 1 (IRF-1), stat1, MCP-1, IL-6 | Antidiabetic Lower liver cholesterol | [95] |
Phaeanthus vietnamensis | (7S,8R,8′R)-9,9′-epoxy-3,5,3′,5′-tetramethoxylignan-4,4′,7-triol | 65.2 | Alkaloids | Anti-inflammatory | [94] | |
8R,8′R-bishydrosyringenin | 25.3 | |||||
(+)-5,5’-Dimethoxylariciresinol | 73.9 | |||||
(+)-Pinoresinol | 60 | |||||
8α-Hydroxyoplop-11(12)-en-14-one | 46.3 | |||||
Spathulenol | 15.7 | NO | ||||
1αH,5βH-aromandendrane-4β,10α-diol | 29.3 | |||||
1αH,5βH-aromandendrane-4α,10α-diol10α-diol | 23.0 | |||||
1βH,5βH-aromandendrane-4α,10β-diol | 22.6 | |||||
3α,4β-dihydroxybisabola-1,10-diene | 39.9 | |||||
Nerolidol | 50.8 | |||||
(1R,2S,4S)-4-acetyl-2-[(E)-(cinnamoyloxy)]-1-methylcyclohexan-1-ol | 45.7 | |||||
Pinus koraiensis | Koraiensides E | 24.1 | Diterpenoid Glycosides | Anti-inflammatory Neuroprotective | [112] | |
Raphanus sativus | Sinapoyl desulfoglucoraphenin | 45.36 | 4-Methylthio-butanyl derivatives | NO | Anti-inflammatory Anti-proliferative | [100] |
Genistein | 137.50 | |||||
Genistein | 10.63 | |||||
Equol | 3.45 | |||||
Salix glandulosa | Saliglandin | 120.18 | Salicin derivatives | NO | Anti-inflammatory | [79] |
6′-O-(Z)-p-coumaroylsalicin | 31.55 | |||||
Salicin | 85.40 | |||||
2′-O-acetylsalicin | 123.36 | |||||
3′-O-acetylsalicin | 27.27 | |||||
Fragilin | 206.12 | |||||
Trumuloidin | 114.30 | |||||
2′-O-(E)-p-coumaroylsalicin 2′-O-(Z)-p-coumaroylsalicin | 29.77 25.47 | |||||
6′-O-(E)-p-coumaroylsalicin | 38.25 | |||||
Salicortin | 13.57 | NO | ||||
2′-O-acetylsalicortin | 14.61 | |||||
3′-O-acetylsalicortin | 18.27 | |||||
6′-O-acetylsalicortin | 22.78 | |||||
Tremulacin | 18.59 | |||||
Cochinchiside A | 23.40 | |||||
Sambucus williamsii | Sambucasinol B | 0.9 | New iridoid glycosides Lignan | NO | Anti-inflammatory Neuroprotective | [63] |
Sambucuside C | 1.3 | |||||
Sambucuside E | 1.2 | |||||
Sambucasinol A | 6.82 | |||||
Lariciresinol | 72.58 | |||||
(7αH,8′αH)-4,4′,8α,9-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan | >500 | |||||
Berchemol | 215.41 | |||||
7-Hydroxylariciresinol | 128.97 | |||||
(−)-Medioresinol | 45.59 | |||||
(−)-Pinoresinol | 34.25 | |||||
7R,8S-dihydrodehydrodiconiferyl alcohol | 39.97 | |||||
Selagginella tamariscina | (2R, 3S) dihydro-2-(3,5-dimethoxy-4-hydroxyphenyl)-7-methoxy-5-acetyl-benzofuran | 32.3 | Lignanoside | NO, iNOS, TNF-α, and NF-κB | Anti-inflammatory | [62] |
Tamariscinoside E | NA | |||||
Smenospongia cerebriformis | Smenohaimiens A | 30.13 | Sesquiterpene derivatives | Anti-inflammatory | [90] | |
Smenohaimiens B | 28.33 | |||||
Smenohaimiens C | >40 | |||||
Smenohaimiens D | >40 | |||||
Smenohaimiens E 19-Hydroxy-polyfibrospongol | 24.37 24.44 | |||||
Ilimaquinone, | 10.40 | NO | ||||
Dictyoceratin C, | >40 | |||||
Polyfibrospongol A, | >40 | |||||
Polyfibrospongol B | 30.43 | |||||
Solanum melongena L | Melongenamide C | 16.4 | Lignanamides | NO | Anti-inflammatory | [61] |
Cannabisin F | 16.2 | |||||
Sophora alopecuroides | Sophoraflavanone G | NA | Flavonoid | NO, PGE2, TNF-α, IL-1β, IL-6, iNOS, COX-2, JAK/STAT, P13K/AKT, MAPKs | Anti-neuroinflammatory | [72] |
Sorbus commixta | Sorcomisides A | NA | Phenolic glycosides | Anti-inflammatory Neuroprotective Anticancer | [113] | |
Sorcomisides B | ||||||
Sorcomic acid | 180.12 | Fatty Acids | Anti-inflammatory Neuroprotective Anticancer | [114] | ||
Methyl (3S,5S)-3,5-dihydroxyhexanoate | 165.03 | |||||
(S)-(E)-4-hydroxy-2-nonenoic acid | >500 | |||||
3(R)-hydroxyoctanoic acid | >500 | |||||
9-Hydroxynonanoic acid | 187.87 | |||||
Methyl 9-hydroxynonanoate | 196.67 | |||||
Azelaric acid | 150.22 | |||||
Monomethyl azelate | >500 | |||||
(9S,12S,13R)-(E)-9,12,13-trihydroxy-10-octadecaenoic acid | 186.67 | |||||
(9S,12R,13R)-(E)-9,12,13-trihydroxy-10-octadecaenoic acid | 71.25 | |||||
Tilia amurensis | Orobol4’-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside | 23.42 | Isoflavonoid glycoside | NO | Anti-neuroinflammatory Anti-proliferative | [70] |
Pratensein-7-O-β- D-glucoside | 32.23 | |||||
Orobol 7-O-β-D-glucoside | 31.85 | |||||
Orobol 4′-O-β-glucopyranoside | >200 | |||||
Kelampayoside A | >200 | |||||
Osmanthuside H | 25.99 | |||||
Salidroside | 35.64 | |||||
Dihydroconiferin | 158.49 | |||||
Isotachioside | 50.29 | |||||
Tachioside | 116.66 | |||||
Koaburside | >200 | |||||
2-Methoxyhydroquinone | 58.87 | |||||
Scopoletin | 37.69 | |||||
Scopolin | 148.92 | |||||
Fraxin | 30.02 | |||||
n-Butyl β-D-glucopyranoside | >200 | |||||
Adenosine | >200 | |||||
Toddaliae asiaticae | Omphalocarpin | 7.4 | Phytoestrogen | NO, TNF-α, IL-1β, COX-2 | Anti-inflammatory | [96] |
Toxicodendron verniciflumm | Butein | 11.68 | Phenols | NO | Cytotoxic Anti-inflammatory | [74] |
Ulmus davidiana | Fraxetin | 18.72 | chromane derivative | Anti-inflammatory Neuroprotective | [115] | |
(+)-lyoniresinol | 12.31 | |||||
4-O-β-D-glucopyranosyl vanillic acid | 21.40 | |||||
Wasabi japonica | Allyl isothiocyanate | 20.10 | Aliphatic isothiocyanate | LPS-activated microglia neuroinflammation | [116] | |
Zanthoxylum schinifolium | Zanthplanispine | 36.8 | Lignan | NO | Anti-inflammatory | [101] |
Zinginber officinale | Gingerols | NA | Polyphenols | NO, NF-κB, IL-6, IL-1β, TNF-α | Anti-inflammatory Neuroprotective | [76] |
Gingerone | NA | |||||
Shogaol | NA | NO | ||||
Zingerone | NA | IL-1β, IL-6, TNF-α, NF-κB, TLR4, MyD88, TRIF | ||||
Paradol | NA | TNF-α, iNOS | ||||
Honokiol | 17.0 | Pyrazole analogs | Anti-inflammatory | [117] | ||
Positive control | L-NMMA | 20.53 | Methyl-arginine | Anti-inflammatory | [89] |
2. Discussion and Future Prospective
Author Contributions
Funding
Conflicts of Interest
References
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No. | Potential NO Inhibitor | IC50 (μM) |
---|---|---|
1. | Sambucasinol B | 0.9 |
2. | Erythro-(7S,8R)-Guaiacylglycerol-β-coniferyl aldehyde ether | 0.925 |
3. | Threo-(7R,8R)-Guaiacylglycerol-β-coniferyl aldehyde ether | 1.05 |
4. | sambucuside E | 1.2 |
5. | sambucuside C | 1.3 |
6. | Betulinic acid | 2.38 |
7. | Equol | 3.45 |
8. | (+)-faurinone | 3.67 |
9. | Maslinic acid | 4.46 |
10. | 2α-O-benzoyl-3β,19α-dihydroxy-urs-12-en-28-oic acid | 4.92 |
11. | Obtusifolisides B | 5.45 |
12. | 23-hydroxybetulinic acid | 6.7 |
13. | Sulforaphane | 5.85 |
14. | Sambucasinol A | 6.82 |
15. | 1-cinnamoyltrichilinin | 7.73 |
16. | Morolic acid 3-O-caffeate | 8.62 |
17. | kaempferol | 8.86 |
18. | Erythro-syringylglycerol-8-O-4′-coniferyl alcohol ether | 9.14 |
19. | 2α-O-benzoyl-19α-hydroxy-3-oxo-urs-12-en-28-oic acid | 9.68 |
20. | Methoxy-Balanophonin | 10 |
21. | Balanophonin | 10.25 |
22. | Ilimaquinone | 10.4 |
23. | Genistein | 10.63 |
24. | Oleuropein | 11.17 |
25. | Costic acid | 12.13 |
26. | (+)-lyoniresinol | 12.31 |
27. | Holophyllane A | 12.74 |
28. | Ilexgenin B | 12.72 |
29. | 3-O-cis-caffeoylbetulinic | 13.4 |
30. | Daidzein | 14.09 |
31. | Alphitolic acid | 14.5 |
32. | Dihydrodehydroconiferyl alcohol | 14.6 |
33. | Neonuezhenide | 14.69 |
34. | Ilicic acid | 14.92 |
35. | Trichilinin B | 15.28 |
36. | Eudeglaucone | 15.9 |
37. | (2″R)-2″- methoxyoleuropein | 15.45 |
38. | Fraxetin | 18.72 |
39. | 1-desacetylnimbolinin B | 18.75 |
40. | L-NMMA | 20.53 |
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Subedi, L.; Gaire, B.P.; Kim, S.-Y.; Parveen, A. Nitric Oxide as a Target for Phytochemicals in Anti-Neuroinflammatory Prevention Therapy. Int. J. Mol. Sci. 2021, 22, 4771. https://doi.org/10.3390/ijms22094771
Subedi L, Gaire BP, Kim S-Y, Parveen A. Nitric Oxide as a Target for Phytochemicals in Anti-Neuroinflammatory Prevention Therapy. International Journal of Molecular Sciences. 2021; 22(9):4771. https://doi.org/10.3390/ijms22094771
Chicago/Turabian StyleSubedi, Lalita, Bhakta Prasad Gaire, Sun-Yeou Kim, and Amna Parveen. 2021. "Nitric Oxide as a Target for Phytochemicals in Anti-Neuroinflammatory Prevention Therapy" International Journal of Molecular Sciences 22, no. 9: 4771. https://doi.org/10.3390/ijms22094771