Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities
Abstract
:1. Introduction
2. Molecular Mechanisms of Inflammation and Oxidative Stress
3. Lignans with Antioxidant and Anti-Inflammatory Action
Lignan | Source | Model/Assay | Target | Concentration | Ref. |
---|---|---|---|---|---|
Aryltetralinstructure group | |||||
(−)-Isoguaiacin | Machilusthunbergii Sieb, et Zucc. | CCl4-induced hepatotoxicity | ↓GPT level | 50–100 μM | [24] |
↓MDA content, ↑GSH/GSSG level, ↑SOD1, ↑CAT | 50 μM | ||||
(+)-Isolariciresinol | Riesling wine | TEAC assay | radical scavenging capacity | 2.5 mmol Trolox/mmol | [25] |
Ephedra viridis | DCFH assay in HL-60 cells | ↓iROS level | IC50 21 μg/mL | [26] | |
Euterpe oleracea Mart. | HO assay | HO• scavenging | IC50 0.68 ± 0.02 μg/mL | [27] | |
DPPH assay | DPPH radical scavenging | IC50 37.4 ± 0.9 μg/mL | |||
(±)-Isolariciresinol | Synthetic | DPPH assay | DPPH radical scavenging | IC50 53.0 μM | [28] |
(−)-Isolariciresinol 5-methoxy-9-β-D-xylopyranoside | Saracaasoca (Roxb.) De Wilde | DPPH assay | DPPH radical scavenging | IC50 44 μM | [29] |
(+)-Isolariciresinol 3a-O-β-D-glucopyranoside | Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 45.7 ± 1.5 μM | [30] |
FRAP assay | ferric-reducing potentiality | 33 mmol Fe2+/g | |||
H2O2-induced L02 cells cytotoxicity | ↓iROS level | 5 μM | |||
Isolariciresinol-9’-O-α-L-arabinofuranoside | Pinus massoniana Lamb. | H2O2-induced HUVECs cytotoxicity | ↑PI3K, ↑p-Akt, ↑p-Bad, ↓Bax | 31.3–125 μg/mL | [31] |
Lyoniresinol | Berberis vulgaris Linn. | HO assay | HO• scavenging | IC50 1.4 ± 0.12 μg/mL | [32] |
Viscum album Linn. | ABTS assay | ABTS radical scavenging | 10–100 μM | [33] | |
DPPH assay | DPPH radical scavenging | ||||
Glu-treated HT22 cells | ↓iROS level | 25 μM | |||
(+)-Lyoniresinol-3α-O-β-glucopyranoside | Strychnosvanprukii | DPPH assay | DPPH radical scavenging | IC50 31.2 μM | [34] |
Sauchinone | Synthetic | AngII-induced mesangial cells | ↓iROS level | 1 μM | [35] |
Dibenzocyclooctadiene structure group | |||||
Gomisin A | Synthetic | ZnPP/high glucose-injured MC3T3 E1 cells | ↓iROS level, ↑SOD, ↑HO-1 | 1–10 μM | [36] |
Gomisin N | Synthetic | HeLa cells | ↑iROS level | 100 μM | [37] |
ethanol-treated HepG2 cells | ↓iROS level, ↑GSH/GSSG level, ↑CAT, ↑SOD, ↑GPx ↑SIRT1/AMPK, ↓CYP2E1 | 50–100 μM | [38] | ||
Schisandrin A | Schisandra chinensis Baill. | CCl4-treated HepG2 cells | ↓TBARS level, ↓iROS level | 50 μM | [39] |
Synthetic | LPS-stimulated RAW 264.7 macrophages | ↓iROS level ↓Keap1, ↑Nrf2, ↑HO-1 | 200 μM | [40] | |
H2O2-induced C2C12 cell cytotoxicity | ↓iROS level, ↑AMPK, ↑Bcl-2/Bax | 200 μM | [41] | ||
DON-induced cytotoxicity in HT-29 cells | ↓iROS level, ↓TBARS level, ↓CAT, ↓SOD, ↓GPx, ↑Nrf2, ↑HO-1, ↑GST, ↑GSH/GSSG level | 2.5–10 μM | [42] | ||
RANKL-induced osteoclast differentiation model | ↓iROS level, ↑Nrf2, ↑HO-1, ↑CAT ↓TRAF6, ↓Nox1 | 50–200 μM | [43] | ||
Schisandrin B | Schisandra chinensis (Turcz.) Baill. | CCl4-treated HepG2 cells | ↓TBARS level | 50 μM | [39] |
↓iROS level | 10–50 μM | ||||
↑CYP3A4 expression and activity | 50 μM | ||||
Synthetic | PQ-induced PC12 cells cytotoxicity | ↓iROS level, ↑GSH/GSSG level | 15 μM | [44] | |
solar-irradiated BJ human fibroblast | ↓iROS level, ↓MMP, ↑GSH/GSSG level | 25–75 μM | [45] | ||
intact lymphocytes | ↑iROS level, ↓GSH/GSSG level, ↑Nrf2, ↑HO-1, ↑TR, ↑GCLC | 25–50 μM | [46] | ||
H2O2-induced PC12 cells cytotoxicity | ↓iROS level, ↓MDA content, ↑SOD | 2.5–10 μM | [47] | ||
↑Bcl-2/Bax, ↑p-Akt/Akt | 10 μM | ||||
CsA-induced cytotoxicity in HK-2 cells | ↓iROS level, ↑GSH/GSSG level, ↑Nrf2, ↑HO-1, ↑NQO1, ↑GCLM ↑Bcl-2/Bax | 2.5–10 μM | [48] | ||
tBHP-induced HaCaT cell injury | ↓iROS level, ↑Nrf2, ↑HO-1, ↑SOD, ↑GPx, ↑CAT, ↑p-AMPK, ↑p-Akt, ↑p-Erk1/2, ↑p-JNK, ↑p-p38 | 2.5–10 μM | [49] | ||
H/R-induced H9c2 cell injury | ↓iROS level, ↑SOD, ↑GPx, ↑Nrf2, ↑NQO-1, ↑HO-1, ↓Keap1, ↑AMPK | 20 μM | [50,51] | ||
Schisandrin C | Synthetic | solar-irradiated BJ human fibroblast | ↓iROS level, ↓MMP, ↑GSH/GSSG level | 25–75 μM | [45] |
LPS-stimulated HDPCs | ↓iROS level, ↑SOD ↑HO-1, ↑PGC-1α, ↑Nrf2, ↑p-Akt | 10–20 μM | [52] | ||
Schisantherin A | Schisandra chinensis (Turcz.) Baill. | CCl4-treated HepG2 cells | ↓TBARS level | 50 μM | [39] |
↓iROS level | 2–50 μM | ||||
Schisandra sphenanthera | H/R-induced HK-2 cells | ↓iROS level, ↑SOD, ↑MDA content ↑Bcl2/Bax, ↑PI3K/AKT | 5–20 μM | [53] | |
LPS-stimulated BV-2 microglial cells | ↓iROS level, ↑HO-1, ↑NQO-1 | 2.5–50 μM | [54] | ||
↑Nrf2 | 50 μM | ||||
Synthetic | LPS-stimulated NRK-52E cells | ↑γGCS, ↑Nrf2 | 25–50 μM | [55] | |
Dibenzylbutane structure group | |||||
(–)-Carinol | Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 20.2 μM | [56] |
Synthetic | DPPH assay | DPPH radical scavenging | IC50 4.4 μg/mL | [57] | |
XOD assay | ↓xanthine oxidase enzyme | IC50 219.4 μg/mL | |||
Meso-dihydroguaiaretic acid | Machilusthunbergii Sieb, et Zucc. | CCl4-induced hepatotoxicity | ↓GPT level | 10–100 μM | [24] |
↓MDA content, ↑GSH/GSSG level, ↑SOD1, ↑CAT | 50 μM | ||||
Machilusphilippinensis Merr. | fMLF-activated human neutrophils | ↓O2•– level | IC50 0.78 ± 0.17 μM | [58] | |
↓iROS level | IC50 0.79 ± 0.26 μM | ||||
↓p-ERK, ↓p-JNK, ↓p-Akt | 10 μM | ||||
MMK-1-activated human neutrophils | ↓O2•– level | IC50 1.17 ± 0.64 μM | |||
PMA-activated human neutrophils | ↓iROS level | IC50 3.57 ± 3.93 μM | |||
ABTS assay | ABTS radical scavenging | 1–10 μM | |||
DPPH assay | DPPH radical scavenging | ||||
ORAC assay | ROS scavenging | ||||
XOD assay | superoxide anion scavenging | ||||
Nordihydroguaiaretic acid | Larrea tridentate | DCFH assay in HL-60 cells | ↓iROS level | IC50 0.7 μg/mL | [59] |
Synthetic | FL5.12 cells | ↑p-ERK1/2, ↑p-JNK, ↑p-p38 | 20 μM | [60] | |
HOCl assay | hypochlorous acid scavenging | IC50 622 ± 42 μM | [61] | ||
O2•– assay | superoxide anion scavenging | IC50 15 ± 1 μM | |||
OH assay | OH radical scavenging | IC50 0.15 ± 0.02 μM | |||
1O2 assay | singlet oxygen scavenging | IC50 151 ± 20 μM | |||
ONOO assay | ONOO anion scavenging | IC50 4 ± 0.94 μM | |||
H2O2/3-NP-induced CGNs neurotoxicity | ↑Nrf2, ↑HO-1 | 20 μM | [62] | ||
OH assay | OH radical scavenging | 10 μM | [63] | ||
TPA-treated mouse model | ↑GPx, ↑GR, ↑GST, ↑GSH/GSSG level, ↑SOD, ↑CAT | 15–25 μM | [64] | ||
H2O2-induced LLC-PK1/MEFs cells cytotoxicity | ↓iROS level, ↑Nrf2, ↑HO-1 ↑p-Akt, ↑p-ERK1/2, ↑p-p38, ↑p-JNK, ↑p-GSK-3 | 15 μM | [65] | ||
IAA/H2O2-induced cytotoxicity in MN and THP-1 cells | ↓iROS level, ↑GSH/GSSG level ↑CD33 | 20 μM | [66] | ||
Daoy cells | ↑GSH/GSSG level | 75 μM | [67] | ||
(–)-Secoisolariciresinol | Taxus yunnanensis | DPPH assay | DPPH radical scavenging | IC50 28.9 μM | [68] |
Araucaria angustifolia | rat liver microsomes | ↓lipid peroxidation activity | IC50 0.1–0.15 μM | [69] | |
O2•– assay | superoxide anion scavenging | IC50 4.8 nM | |||
ROO assay | peroxyl radicals scavenging | SF 3.1–4.0 mole/mole | |||
Piceaabies | DPPH assay | DPPH radical scavenging | IC50 9.0 ± 1.0 μM | [70] | |
Linum usitatissimum Linn. | L-α-phosphatidylcholine liposome/pBR322 plasmid DNA | AAPH radical scavenging | 50–100 μM | [71] | |
DPPH radical scavenging | 25–200 μM | ||||
Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 26.2 μM | [56] | |
Secoisolariciresinol-7-hydroxyl | Piceaabies | DPPH assay | DPPH radical scavenging | IC50 12.7 ± 1.5 μM | [70] |
Secoisolariciresinol diglucoside | Linum usitatissimum Linn. | L-α-phosphatidylcholine liposome/pBR322 plasmid DNA | AAPH radical scavenging | 10–100 μM | [71] |
DPPH radical scavenging | 25–200 μM | ||||
Synthetic | DPPH assay | DPPH radical scavenging | IC50 78.9 ± 0.29 μg/mL | [72] | |
Linum usitatissimum Linn. | iron treated H9c2 cells | ↓iROS level, ↑SOD, ↑Bcl-2/Bax ↓MMP-2, ↓MMP-9, ↓FOXO3a, ↓p70S6K1, ↑AMPK | 500 μM | [73] | |
Synthetic (LGM2605) | asbestos-exposed MFs | ↓iROS level, ↓MDA content, ↓8-isoP, ↑Nrf2, ↑NQO-1, ↑HO-1, ↑GST, ↑TR, ↓nitrate/nitrite ratio | 50–100 μM | [74,75] | |
LPS-stimulated AC16 cells | ↓iROS level | 50 μM | [76] | ||
Dibenzylbutyrolactone structure group | |||||
Arctigenin | Synthetic | glutamate-treated rat cortical cells | ↓iROS level | IC50 33.2 μM | [77] |
LPS-treated Raw264.7 cells | ↓iROS level | 5–50 μM | [78] | ||
Arctium lappa Linn. | glucose-starved A549 cells | ↓iROS level | 10 μM | [79] | |
H2O2-treated L6 cells | ↑Nrf2, ↑SOD, ↑GR, ↑GPx, ↑Trx1, ↑UCP2, ↑p-AMPK, ↑p-p53, ↑p21, ↑PGC-1α, ↑PPARα | 1–20 μM | [80] | ||
Synthetic | MDA-MB-231 cells | ↑iROS level, ↓GSH/GSSG level, ↑Nox, ↑p-p38, ↑p-ATF-2, ↓Bcl-2 | 5 μM | [81] | |
H2O2-treated astrocytes | ↓iROS level | 10–20 μM | [82] | ||
intact astrocytes | ↑HO-1, ↑Nrf2, ↑c-Jun, ↑p-Akt | ||||
TGF-β1-induced HK-2 cells | ↓iROS level, ↓Nox ↓p-Akt, ↓p-ERK1/2, ↓p-IκBα | 0.5–1 μM | [83] | ||
Arctium lappa Linn. | DPPH assay | DPPH radical scavenging | IC50 31.47 ± 2.33 μM | [84] | |
H2DCF-DA assay | ↓iROS level | 10–100 μM | |||
Synthetic | OA-treated WRL68 hepatocytes | ↓MDA content ↑p-PI3K, ↑p-Akt, ↑p-AMPK | 50 μM | [85] | |
Hep G2 cells | ↑iROS level, ↓GSH/GSSG level | 5–100 μM | [86] | ||
↑p-p38, ↑p-JNK | 20 μM | ||||
OGD-injured H9c2 cardiomyocytes | ↓iROS level, ↓MDA content, ↑SOD ↑AMPK/SIRT1 | 50–200 μM | [87] | ||
silica-injured RAW 264.7 macrophages | ↓iROS level | 1 μM | [88] | ||
Hinokinin | Synthetic | antioxidant assay | inhibition of H2O2 produced by Trypanosoma cruzi mitochondria | IC50 17.84 μM | [89] |
Matairesinol | Cedrus deodara | DPPH assay | DPPH radical scavenging | IC50 33.24 ± 0.47 μM | [90] |
Piceaabies | rat liver microsomes | ↓lipid peroxidation activity | IC50 0.28 μM | [69] | |
O2•– assay | superoxide anion scavenging | IC50 40 nM | |||
ROO assay | peroxyl radicals scavenging | SF 1.0 mole/mole | |||
DPPH assay | DPPH radical scavenging | IC50 14.0 ± 0.0 μM | [70] | ||
Arctium lappa | DPPH assay | DPPH radical scavenging | IC50 14.95 ± 0.38 μM | [84] | |
H2DCF-DA assay | ↓iROS level | 100 μM | |||
Synthetic | DPPH assay | DPPH radical scavenging | 20 μM | [91] | |
O2•– assay | superoxide anion scavenging | ||||
hypoxia-induced HeLa cells | ↓miROS levels ↓HIF-1α, ↓VEGF | 10–50 μM | [92] | ||
LPS-stimulated NSC-34 neurons and BV2 microglia | ↓MDA content, ↑SOD, ↑CAT, ↑GPx, ↑Nrf2, ↑HO-1, ↑AMPK | 5–20 μM | [93] | ||
Matairesinol-7′-hydroxyl | Piceaabies | rat liver microsomes | ↓lipid peroxidation activity | IC50 0.15–0.18 μM | [69] |
O2•– assay | superoxide anion scavenging | IC50 217 nM | |||
ROO assay | peroxyl radicals scavenging | SF 2.1–2.7 mole/mole | |||
DPPH assay | DPPH radical scavenging | IC50 15.7 ± 0.6 μM | [70] | ||
DPPH assay | DPPH radical scavenging | IC50 20.0 ± 0.1 μM | [94] | ||
(+)-Nortrachelogenin | Wikstroemia indica | DPPH assay | DPPH radical scavenging | IC50 90.1 μM | [95] |
(–)-Nortrachelogenin | Cedrus deodara | DPPH assay | DPPH radical scavenging | IC50 36.79 ± 1.69 μM | [90] |
Pinus contorta | rat liver microsomes | ↓lipid peroxidation activity | IC50 0.14–0.19 μM | [69] | |
O2•– assay | superoxide anion scavenging | IC50 1.4 nM | |||
ROO assay | peroxyl radicals scavenging | SF 2.0–2.2 mole/mole | |||
Piceaabies | DPPH assay | DPPH radical scavenging | IC50 17.7 ± 1.5 μM | [70] | |
Carissa carandas Linn. | DPPH assay | DPPH radical scavenging | IC50 30.2 μM | [96] | |
Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 35.8 μM | [56] | |
Galactites elegans | DPPH assay | DPPH radical scavenging | IC50 38.6 ± 2.7 μM | [97] | |
BHP-treated Jurkat cells | peroxyl radicals scavenging | 50 μM | |||
Furanoid structure group | |||||
(+)-Lariciresinol | Abies balsamea | rat liver microsomes | ↓lipid peroxidation activity | IC50 0.17–0.35 μM | [69] |
O2•– assay | superoxide anion scavenging | IC50 35 nM | |||
ROO assay | peroxyl radicals scavenging | SF 1.0–2.6 mole/mole | |||
Hemerocallis fulva | LUVs assay | ↓lipid peroxidation activity | 50 μg/mL | [98] | |
Piceaabies | DPPH assay | DPPH radical scavenging | IC50 10.7 ± 1.2 μM | [70] | |
Ephedra viridis | DCFH assay in HL-60 cells | ↓iROS level | IC50 17.7 μg/mL | [26] | |
Euterpe oleracea Mart. | HO assay | HO• scavenging | IC50 0.70 ± 0.13 μg/mL | [27] | |
DPPH assay | DPPH radical scavenging | IC50 22.4 ± 3.0 μg/mL | |||
Rubia philippinensis | ABTS assay | ABTS radical scavenging | 12.5–50 μM | [99] | |
DPPH assay | DPPH radical scavenging | ||||
HO assay | HO• scavenging | 1.5–6 μM | |||
ORAC assay | ↓ROO•-induced oxidation | ||||
CUPRAC assay | cupric-reducing potentiality | 6.25–50 μM | |||
FRAP assay | ferric-reducing potentiality | ||||
AAPH-treated RAW 264.7 cells | ↓iROS level | 12.5–50 μM | |||
RAW 264.7 cells | ↑Nrf2, ↑SOD1, ↑CAT, ↑GPx, ↑HO-1, ↑NQO1, ↑GCLc, ↑GCLm ↑p-p38, ↑p-ERK1/2 | ||||
Nectandrin B | Myristica fragrans | DPPH assay | DPPH radical scavenging | 5–50 μg/mL | [100] |
old HDFs | ↓p-AMPK, ↑p-PI3K, ↑p-Akt, ↓p-ERK1/2, ↓p-p38 | 10–20 μg/mL | |||
H2O2/palmitic acid-treated old HDFs | ↓iROS level, ↑SOD1,2 | ||||
(−)-Olivil | Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 18.1 μM | [56] |
Taxiresinol | Taxus yunnanensis | DPPH assay | DPPH radical scavenging | IC50 18.4 μM | [68] |
Furofuranoid structure group | |||||
4-ketopinoresinol | Coixlachryma-jobi Linn. var. ma-yuen Stapf | DPPH assay | DPPH radical scavenging | IC50 52.7 ± 4.6 μg/mL | [101] |
H2O2-induced HSC-3 cell cytotoxicity | ↓iROS level | 12.5–50 μM | [102] | ||
↑GSH/GSSG level | 50 μM | ||||
↑Nrf2 | 6.25–50 μM | ||||
↑HO-1, ↑AKR1C1-3, ↑ABCC2, ↑GR, ↑GCLC, ↑GCLM, ↑TR, ↑ABCC5, ↑PI3K/Akt | 25 μM | ||||
Galactites elegans | DPPH assay | DPPH radical scavenging | IC50 143.3 ± 13.1 μM | [97] | |
BHP-treated Jurkat cells | peroxyl radicals scavenging | 50 μM | |||
Dendranlignan A | Dendranthema morifolium (Ramat.) | LPS-induced H9c2 cells | ↓iROS level | 10 μM | [103] |
Isoeucommin A | Eucommia ulmoides Oliv. | high-glucose-stimulated HRMCs | ↓MDA content, ↑SOD,↑p-GSK-3β, ↑Nrf2, ↑HO-1 | 62.5–125 μM | [104] |
Koreanaside A | Forsythia koreana | ORAC assay | ↓ROO•-induced oxidation | 25 μg/mL | [105] |
MOVAS cells | ↓VCAM-1 | ||||
Pinoresinol | Forsythia suspensa (Thunb.) | Cu2+-induced LDL lipid peroxidation | ↓lipid peroxidation activity | IC50 1.39 μM | [106] |
Eucalyptus globulus Labill | rat liver microsomes | ↓lipid peroxidation activity | IC50 7.9 μg/mL | [107] | |
Piceaabies | DPPH assay | DPPH radical scavenging | IC50 17.7 ± 0.6 μM | [70] | |
Euterpe oleracea Mart. | DPPH assay | DPPH radical scavenging | IC50 34.7 ± 5.0 μg/mL | [27] | |
HO assay | HO• scavenging | IC50 1.8 ± 0.2 μg/mL | |||
Carissa spinarum Linn. | DPPH assay | DPPH radical scavenging | IC50 43.4 μM | [56] | |
Forsythia koreana | ORAC assay | ↓ROO•-induced oxidation | 25 μg/mL | [105] | |
Galactites elegans | DPPH assay | DPPH radical scavenging | IC50 50.8 ± 3.1 μM | [97] | |
Cinnamon | intact Beas-2B cells | ↑Nrf2, ↑NQO1, ↑γ-GCS | 25 μM | [108] | |
As(III)-induced Beas-2B cells injury | ↓iROS level, ↑GSH/GSSG level | ||||
Pinoresinol diglucoside | Eucommia ulmoides | oxLDL-induced HUVECs cytotoxicity | ↓iROS level, ↓MDA content, ↑SOD | 1 μM | [109] |
Sesamin | Sesamum indicum Linn. | oxLDL-induced HUVECs cytotoxicity | ↓iROS level, ↑SOD1 ↑Bcl-2/Bax level | 12.5–100 μM | [110] |
Synthetic | KA-induced PC12 and BV-2 cells | ↓iROS level, ↓MDA content | 0.1–2 μM | [111] | |
Sesamum indicum Linn. | dexamethasone-treated osteoblasts | ↓iROS level, ↑Bcl-2/Bax, ↑p-Akt | 5–20 μM | [112] | |
H2O2-induced Caco-2 cell cytotoxicity | ↓iROS, ↑GSH/GSSG level, ↓MDA content, ↑SOD, ↑Nrf2, ↓Keap1, ↑HO-1, ↑NQO1, ↑GCLC, ↑GCLM, ↑GR, ↑p-AKT, ↑p-ERK1/2 | 20–80 μM | [113] | ||
H2O2-induced SH-SY5Y cell cytotoxicity | ↓iROS level, ↑SOD2, ↑CAT ↑FoxO3a, ↑SIRT1, ↑SIRT3 | 1 μM | [114] | ||
Syringaresinol | Coixlachryma-jobi Linn. var. ma-yuen Stapf | DPPH assay | DPPH radical scavenging | IC50 24.6 ± 3.1 μg/mL | [101] |
Euterpe oleracea Mart. | DPPH assay | DPPH radical scavenging | IC50 29.7 ± 2.0 μg/mL | [27] | |
HO assay | HO• scavenging | IC50 0.40 ± 0.13 μg/mL | |||
Panax ginseng C.A. Meyer | H/R-induced H9c2 cells | ↓iROS level, ↑MnSOD, ↑CAT, ↑LC3, ↑Bcl-2/Bax, ↓HIF-1, ↑FoxO3a, ↓BNIP3, ↓cCYC, ↑mCYC | 25 μM | [115] | |
Sargentodoxa cuneata | high glucose-injured NRVMs | ↑Nrf2, ↑NQO-1, ↑HO-1, ↓Keap1, ↑SOD, ↑Bcl-2/Bax | 50–100 μM | [116] |
3.1. Arylnaphthalene Skeletons
Sevanol
3.2. Aryltetralin Skeletons
3.2.1. Isoguaiacin
3.2.2. Isolariciresinol and Isolariciresinol Glucoconjugates
3.2.3. Lyoniresinol and Its Derivatives
3.2.4. Podophyllotoxin
3.2.5. Sauchinone
Lignan | Source | Model | Target | Dose, Road | Ref. | |
---|---|---|---|---|---|---|
Dibenzocyclooctadiene structure group | ||||||
Gomisin A | Schisandra chinensis Baill. | CCl4-induced hepatotoxicity | ↓MDA content, ↑SOD | 50–100 mg/kg of rat, i.p. | [127] | |
Gomisin N | Synthetic | ethanol-injured model | ↓iROS, ↑GSH/GSSG, ↑CAT, ↑SOD, ↑GPx, ↑SIRT1/AMPK, ↓CYP2E1 | 5–20 mg/kg of mice, p.o. | [38] | |
Schisandrin A | Synthetic | ovariectomy-induced osteoporosis | ↓iROS level, ↑Nrf2 | 100 mg/kg of mice, i.p. | [43] | |
Schisandrin B | Schisandra chinensis (Turcz.) Baill. | I/R injury model | ↑GSH/GSSG level | 1.2 mmol/kg of rat, e.v.p. | [128] | |
Synthetic | CCl4-induced hepatotoxicity | ↑mtGSH/GSSG level, ↓mtMDA content, ↑GR, ↑GST, ↑GPx | 2 mmol/kg of mice, p.o. | [129,130] | ||
ethanol-injured model | ↓iROS, ↑GSH/GSSG level, ↑α-TOC, ↓MDA content, ↑GR, ↑GST, ↑MnSOD, ↑GPx | 10 mg/kg of rat, i.g. | [131] | |||
Aβ-infused model | inhibition of ROO•-induced oxidation, ↑ORAC, ↑GSH/GSSG level, ↓MDA content, ↑SOD | 25–50 mg/kg of rat, p.o. | [132] | |||
TSCI model | ↑SOD | 50 mg/kg of rat, p.o. | [133] | |||
I/R injury model | ↓MDA content, ↑SOD | 80 mg/kg of rat, p.o. | [134] | |||
STZ-induced diabetic model | ↓iROS level, ↑Nrf2 ↑Bcl-2/Bax | 20 mg/kg of mice, p.o. | [135] | |||
acute stress-induced anxiety | ↓iROS level, ↓Keap1, ↑Nrf2, ↑SOD, ↑GSH/GSSG level | 30–60 mg/kg of mice, p.o. | [136] | |||
pirarubicin-induced cardiotoxicity | ↑SOD2, ↑CAT ↑Bcl-2/Bax | 50 mg/kg of rat, diet | [137] | |||
Schisandrin C | Synthetic | Ang II-induced endothelial deficit model | ↓iROS level ↑Nrf2, ↑NQO-1, ↑HO-1, ↓Keap1 | 10 mg/kg of mice, i.g. | [138] | |
Schisantherin A | Schisandra chinensis (Turcz.) Baill. | Aβ-infused model | ↓MDA content, ↑GSH/GSSG level, ↑SOD, ↑GPx | 0.1 mg/kg of mice, i.c.v. | [139] | |
chronic fatigue/D-galactose-induced LMI model | ↑GSH/GSSG level, ↓MDA content, ↓Keap1, ↑Nrf2, ↑HO-1, ↑SOD, ↑CAT, ↑Bcl-2/Bax | 2.5–5 mg/kg of mice, i.g. | [140,141] | |||
Synthetic | MCAO/R-induced brain injury | ↓MDA level, ↑SOD, ↑Trx, ↑PRDx, ↓NOX4 | 5–10 mg/kg of rat, i.g. | [142] | ||
Dibenzylbutane structure group | ||||||
Nordihydroguaiaretic acid | Synthetic | ozone-induced lung injury | ↓tyrosine nitration level | 20 mg/kg of rat, Alzet osmotic pumps | [61] | |
K2Cr2O7-induced renal injury | ↓NAG, ↑GPx | 17 mg/kg of rat, mini-osmotic pumps | [143] | |||
Larrea tridentata | ALIOS-fed model | ↑GPx4, ↑PRDx3, ↑PPARα | 2.5 g/kg of mice, diet | [144] | ||
Secoisolariciresinol diglucoside | Linum usitatissimum Linn. | metabolic syndrome model | ↓TBARS, ↓iROS, ↑GSH/GSSG level, ↑SOD, ↑CAT, ↑GPx | 20 mg/kg of rat, p.o. | [145] | |
Synthetic | CCl4-induced hepato- and nephrotoxicity | ↓MDA content, ↑CAT, ↑SOD, ↑POX, ↓LPO | 12.5–25 mg/kg of rat, p.o. | [72] | ||
MCT-induced heart failure | ↓iROS level, ↑SOD, ↑CAT, ↑GPx | 25 mg/kg of rat, p.o. | [146] | |||
Synthetic (LGM2605) | CLP-induced sepsis | ↓iROS level | 100 mg/kg of mice, i.p. | [76] | ||
NRC painful model | ↓8-OHG | 200 mg/kg of rat, s.c. | [147] | |||
Linum usitatissimum Linn. | CdCl2-injured model | ↑SOD, ↑CAT, ↑GPx, ↑GR | 10 mg/kg of rat, s.c. | [148] | ||
Synthetic | BaP-injured model | ↑GSH/GSSG, ↓MDA, ↑SOD, ↑CAT ↓p-p38, ↓p-ERK, ↑MKP-1, ↓miR-101A | 100 mg/kg of mice, i.g. | [149] | ||
aging ovaries | ↓iROS level | 7–70 mg/kg of mice, i.g. | [150] | |||
Dibenzylbutyrolactone structure group | ||||||
Arctigenin | Arctium lappa Linn. | WFST model | ↑Nrf2, ↑SOD, ↑GR, ↑GPx, ↑Trx1, ↑UCP2, ↑p-AMPK, ↑p-p53, ↑p21, ↑PGC-1α, ↑PPARα | 15 mg/kg of rat, i.p. | [80] | |
ethanol-induced gastric ulcer | ↓MDA content, ↑SOD | 0.05–0.45 mg/kg of rat, p.o. | [151] | |||
Synthetic | JEV-infected model | ↓ROS level, ↑SOD1 | 10 mg/kg of mice, i.p. | [152] | ||
LPS-injured model | ↑GSH/GSSG level, ↓MDA content, ↑SOD, ↑CAT, ↑HO-1 | 50 mg/kg of mice, i.p. | [153] | |||
I/R injury model | ↓MDA content, ↑SOD, ↑GPx ↑Nox1, ↑Trx1, ↑Nrf2 | 50–200 mg/kg of rat, i.g. | [154] | |||
AMI model | ↓MDA content, ↑SOD, ↑GPx, ↑CAT, ↑HO-1 | 100–200 μmol/kg of rat | [155] | |||
Hep G2 xenograft model | ↑p-p38, ↑p-JNK,↑Bax,↑TNF-α | 20 mg/kg of mice, s.c. | [86] | |||
BLM-induced skin fibrosis | ↑GSH/GSSG level, ↓MDA content, ↑SOD, ↑Nrf2, ↑HO-1 | 3 mg/kg of mice, i.p. | [156] | |||
I/R injury model | ↓iROS level, ↓MDA content, ↑SOD ↑AMPK/SIRT1 | 100 μmol/kg of rat, i.p. | [87] | |||
cadmium-intoxicated model | ↑GSH/GSSG, ↓8-oxo-dG level, ↓MDA, ↑GSR, ↑GCL, ↑GPx, ↑CAT ↑Nrf2, ↑HO-1, ↑NQO1 | 80 mg/kg of rat, i.g. | [157] | |||
Hinokinin | Synthetic | HFD/STZ-induced type 2 diabetes | ↓MDA, ↑SOD, ↑CAT, ↑GPx, ↑GST, ↑HO-1, ↑Nrf2, ↓Keap-1 | 20–40 mg/kg of mice, p.o. | [158] | |
Matairesinol | Synthetic | CLP-induced sepsis | ↓MDA content, ↑SOD, ↑CAT, ↑GPx, ↑Nrf2, ↑HO-1, ↑AMPK | 5–20 mg/kg of rat, p.o. | [93] | |
Furofuranoid structure group | ||||||
Fargesin | Synthetic | I/R injury model | ↓MDA content, ↓ROS level, ↑SOD, ↑GPx, ↑CAT | 15 μmol/kg of rat, i.v. | [159] | |
Isoeucommin A | Eucommia ulmoides Oliv. | H2O2-injured RTECs | ↑SOD, ↑HO-1, ↑Nrf2 | 31.25–125 μM | [104] | |
↑GSH/GSSG level | 62.5–125 μM | |||||
↓MDA content | 125 μM | |||||
STZ-induced diabetic nephropathy | ↓MDA content, ↑GSH/GSSG level | 2.5–10 mg/kg of rat, i.v. | ||||
↑SOD | 5–10 mg/kg of rat, i.v. | |||||
Pinoresinol diglucoside | Synthetic | Aβ-infused model | ↓iROS level, ↓MDA content, ↑SOD, ↑CAT, ↑Nrf2, ↑HO-1 ↑Bcl-2/Bax | 5–10 mg/kg of mice, i.g. | [160] | |
MCAO model | ↓iROS level, ↓MDA content, ↑GSH/GSSG level, ↑SOD, ↑GPx, ↑Nrf2, ↑NQO-1, ↑HO-1 | 5–10 mg/kg of mice, i.v. | [161] | |||
Sesamin | Synthetic | STZ-induced diabetes | ↓MDA content, ↑SOD | 20 mg/kg of rat, p.o. | [162] | |
nickel-induced hepatotoxicity | ↓iROS, ↓TBARS, ↑GSH/GSSG level, ↓8-OHdG, ↑SOD, ↑CAT, ↑GPx ↑PI3K/AKT, ↑Bcl-2/Bax | 60–120 mg/kg of mice, p.o. | [163] | |||
CCl4-induced hepatotoxicity | ↓iROS, ↓TBARS level ↓p-JNK, ↓p-c-Jun, ↓cCYC, ↓Bax, ↓Bak, ↓Bcl-2 | 60–120 mg/kg of mice, p.o. | [164] | |||
fluoride-exposed model | ↓iROS, ↓TBARS, ↑GSH/GSSG level, ↑SOD, ↑CAT, ↑GPx, ↑GST ↓p-JNK, ↓p-c-Jun, ↑Bcl-2/Bax | 0.5–1 g/kg of carp, diet | [165] | |||
Sesamum indicum Linn. | DOX-treated model | ↓iROS level, ↓MDA content ↑SOD, ↑CAT, ↑GPx | 20–40 mg/kg of rat, i.g. | [166] | ||
6-OHDA model | ↓iROS level, ↓MDA content, ↑SOD | 20 mg/kg of rat, p.o. | [167] | |||
LPS-treated model | ↑SOD, ↓MDA content | 10 mg/kg of rat, p.o. | [168] | |||
LPS-treated model | ↑GSH/GSSG level, ↓MDA content ↑SOD, ↑CAT, ↑Nrf2 | 100 mg/kg of mice, p.o. | [169] | |||
DSS-induced colitis | ↓iROS level, ↑GSH/GSSG level, ↓MDA content, ↑SOD, ↑Nrf2, ↓Keap1, ↑HO-1, ↑NQO1, ↑GCLC, ↑GCLM, ↑GR, ↑p-AKT, ↑p-ERK1/2 | 50–100 mg/kg of mice, i.g. | [113] | |||
cisplatin-injured model | ↓MDA content, ↑SOD, ↑Nrf2 ↓nitrate/nitrite ratio | 5 mg/kg of rat, p.o. | [170] | |||
adult Drosophila | ↑Nrf2/Cnc | 2 mg/mL, diet | [171] | |||
Syringaresinol | Panax ginseng C.A. Meyer | Sod1–/– double-mutant model | ↓iROS level, ↓8-isoprostane level ↓FoxO3a, ↓MMP-2 | 50 mg/kg of mice, p.o. | [172] | |
Sargentodoxa cuneata | STZ-induced diabetes | ↑Nrf2, ↑NQO-1, ↑HO-1, ↓Keap1, ↑SOD, ↑Bcl-2/Bax | 25 mg/kg of mice, p.o. | [116] |
3.3. Dibenzocyclooctadiene Skeletons
3.3.1. Gomisins
3.3.2. Schisandrins
3.3.3. Schisantherin A
Lignan | Source | In Vitro Model | Target | Concentration | Ref. |
---|---|---|---|---|---|
Arylnaphthalene structure group | |||||
Sevanol | Thymus armeniacus | HEO of X. laevis | ↓hASIC3 | IC50 353 ± 23 μM | [119] |
↓rASIC1a | IC50 2.2 ± 0.6 mM | ||||
Synthetic | HEO of X. laevis | ↓rASIC3 | IC50 175 ± 18 μM | [120,121] | |
↓rASIC1a | IC50 227.5 ± 37.4 μM | ||||
RA-treated SH-SY5Y cells | ↓hASIC1a | 300 μM | [118] | ||
Aryltetralin structure group | |||||
(+)-Isolariciresinol 3a-O-β-D-glucopyranoside | Carissa spinarum Linn. | COX-2 assay | ↓COX-2 | IC50 0.3 μM | [30] |
Sauchinone | Saururus chinensis | LPS-stimulated RAW264.7 | ↓NO production | IC50 4.08 μM | [124] |
↓iNOS, ↓TNF-α, ↓COX-2 | 1–30 μM | [125] | |||
Synthetic | AngII-induced mesangial cells | ↓TGF-β, | 0.1–1 μM | [35] | |
↓NLRP3, ↓ICAM-1, ↓MCP-1, ↓IL-1β, ↓NF-κB p65 | 1 μM | ||||
Dibenzocyclooctadiene structure group | |||||
Schisandrin A | Schisandra chinensis (Turcz.) Baill. | LPS-stimulated RAW 264.7 macrophages | ↓NO level, ↓iNOS, ↓PGE2, ↓COX-2, ↓NF-κB, ↑IκBα, ↓p-JNK, ↓p-p38 MAPK | 25–100 μM | [173] |
Synthetic | LPS-stimulated RAW 264.7 macrophages | ↓iNOS, ↓COX-2, ↓TNF-α, ↓IL-1β, ↑IκB-α, ↓p-JNK, ↓p-p38 MAPK, ↓p-ERK, ↓p-PI3K, ↓p-Akt | 200 μM | [40] | |
DON-induced cytotoxicity in HT-29 cells | ↓PGE2, ↓COX-2, ↓NF-κB, ↓IL8, ↓p-p38, ↓p-ERK | 2.5–10 μM | [42] | ||
RANKL-induced osteoclast differentiation | ↓PGE2, ↓COX-2, ↓NF-κB, ↓IL8, ↓p-p38, ↓p-ERK | 50–200 μM | [43] | ||
Schisandrin B | Synthetic | Con A-induced lymphocytes | ↓NF-κB, ↓p-MEK, ↓p-p38, ↓p-ERK, ↓p-JNK, ↑IκBα, ↓IL-2, ↓IL-4, ↓IL-6, ↓IFN-γ | 25–50 μM | [46] |
Ang II/TNF-α/ROS-induced HUVECs | ↓NF-κB, TNF-α, ↓p-Smad2/3, ↓vimentin, ↓α-SMA, ↓Snail/slug, ↓TGF-β, ↓Twist, ↑VE-cadherin | 10 μM | [176] | ||
TH17 cell differentiation | ↓p-STAT3 | 1 μM | [178] | ||
H/R-induced H9c2 cell injury | ↓IL-1β, ↓TNF-α, ↓IL-6, ↓IL-8, ↓TGF-β, ↑IL-10 | 20 μM | [50,51] | ||
LPS+ATP-treated intestinal epithelial cells | ↓TNF-α, ↓IL-6, ↓IL-18, ↓IL-1β, ↓NLRP3, ↑p-AMPK | 40 μM | [177] | ||
Schisandrin C | Synthetic | LPS-stimulated HDPCs | ↓NO level, ↓p-ERK1/2, ↓p-SAPK/JNK, ↓p-p38, ↓NF-κB | 10–20 μM | [52] |
Schisantherin A | Schisandra chinensis (Turcz.) Baill. | H/R-induced HK-2 cells | ↓TNF-α, ↓IL-1β, ↓IL-6 | 5–20 μM | [53] |
LPS-stimulated BV-2 microglial cells | ↓NF-κB, ↓IKK, ↑IκB, ↓TNF-α, ↓IL-6, ↓IL-1β, ↑IL-10 ↓iNOS, ↓COX-2 ↓p-p38, ↑p-ERK, ↓p-JNK, ↓p-Akt | 50 μM | [54] | ||
Synthetic | LPS-stimulated NRK-52E cells | ↓NF-κB, ↓TNF-α, ↓Rantes | 25–50 μM | [55] | |
Dibenzylbutane structure group | |||||
Nordihydroguaiaretic acid | Synthetic | IL-1β-induced PC12 cells | ↓APP secretion and processing | 10 μM | [183] |
IFN-γ- induced rat brain astrocytes/C6 cells | ↓IRF-1, ↓IP-10 ↓p-STAT1, ↓p-STAT3,↓p-↓JAK2 | 5–20 μM | [184] | ||
RANKL-induced bone marrow-derived macrophage/RAW-D cells | ↓osteoclast differentiation, ↓RANKL-induced signal cascade ↓NFATc1, ↓p-ERK | 1–10 μM | [185] | ||
Secoisolariciresinol diglucoside | Linum usitatissimum Linn. | iron treated H9c2 cells | ↓TNF-α, ↑IL-10 | 500 μM | [73] |
CdCl2-injured model | ↓MPO, ↓NO level | 10 mg/kg of rat | [148] | ||
Synthetic (LGM2605) | asbestos-exposed MFs | ↓iNOS, ↓IL-1β, ↓IL-6, ↓IL-18, ↓TNFα | 50–100 μM | [74,75] | |
Dibenzylbutyrolactone structure group | |||||
Arctigenin | Forsythia fructus | pro-inflammatory enzyme assays | ↓PLA2, ↓COX-1, ↓COX-2, ↓5-LOX | 100 μM | [186] |
Arctium lappa Linn. | bone marrow-derived MDSCs | ↑Arg-1, ↑iNOS | 10–20 μM | [187] | |
Synthetic | LPS-treated Raw264.7 cells | ↓iNOS, ↓p-STAT, ↓IL-1β, ↓IL-6, ↓MCP-1, ↓p-JAK2 | 5–50 μM | [78] | |
TGF-β1-induced HK-2 cells | ↓NF-κB p65, ↓MCP-1 | 0.5–1 μM | [83] | ||
OA-treated WRL68 hepatocytes | ↓ICAM-1, ↓IL-1β, ↓IL-6, ↓IL-7, ↓IL-8, ↓TNFα | 50 μM | [85] | ||
LPS-treated RAW264.7 cells | ↓TNF-α, ↓IFN-γ, ↓IL-17, ↓IL-1β, ↓CXCL10, ↑TGF-β1, ↑IL-4 | 10–100 μM | [188] | ||
LPS-treated RAW264.7 cells | ↓TNF-α, ↓IFN-γ, ↓IL-17, ↓IL-1β, ↓CXCL10, ↑TGF-β1, ↑IL-4 | 10–100 μM | [188] | ||
IL-1β–stimulated human chondrocytes | ↓TNF-α, ↓COX-2, ↓iNOS, ↓IL-6, ↓PGE2, ↓NO, ↑IκBα, ↓p65, ↓PI3K, ↓Akt | 10–50 μM | [189] | ||
scintillation proximity assay | ↓PDE4 | IC50 3.76 ± 0.28 μM | [190] | ||
LPS-stimulated human PBMCs | ↓TNF-α | IC50 35.18 ± 6.01 μM | |||
LPS-treated RAW264.7 cells | ↓TNF-α, ↑p-CREB, ↓PDE4 | 100 μM | |||
OGD-injured H9c2 cardiomyocytes | ↓NF-κB, ↑IKBα, ↓TNF-α, ↓IL-1β, ↓IL-6 | 50–200 μM | [87] | ||
silica-injured RAW 264.7 macrophages | ↓iNOS, ↓Arg-1, ↓TLR-4, ↓NLRP3, ↓TGF-β | 1 μM | [88] | ||
Hinokinin | Aristolochia indica L. | LPS-stimulated THP-1 cells | ↓IL-6 | 20.5 ± 0.5 μM | [191] |
↓TNF-α | 77.5 ± 27.5 μM | ||||
Matairesinol | Synthetic | naive CD4+ T cells | ↓p-p38, ↓p-ERK, ↓ROR-γt | 20 μM | [192] |
LPS-stimulatedNSC-34neurons andBV2microglia | ↓TNF-α, ↓IL-1β, ↓IL-6, ↓IFN-γ, ↓IL-8, ↓MCP1, ↓MAPK, ↓JNK, ↓NF-κB | 5–20 μM | [93] | ||
Matairesinol-7′-hydroxyl | Piceaabies | TNF-α-induced HAEC | ↓ICAM-1, ↓VCAM-1, ↓monocyte adhesion | 0.1–100 μM | [193] |
↓p-NF-κB | 10–100 μM | ||||
↓p-ERK | 100 μM | ||||
Nortrachelogenin | Synthetic | LPS-stimulated J774 macrophages | ↓PGE2, ↓NO, ↓iNOS | 1–30 μM | [194] |
↓MCP-1, ↓IL-6 | 3–30 μM | ||||
↓mPGES-1 | 30 μM | ||||
Furanoid structure group | |||||
(−)-Olivil | Osmanthus fragrans var. aurantiacus | LPS-activated RAW264.7 cells | ↓NO level | IC50 85.6 ± 1.49 μM | [195] |
Taxiresinol | Osmanthus fragrans var. aurantiacus | LPS-activated RAW264.7 cells | ↓NO level | IC50 58.1 ± 1.42 μM | [195] |
Perovskiaatriplicifolia Benth | RBL-1 leukemia cells | ↓leukotriene C4 release | IC50 3.4 ± 0.09 μM | [196] | |
Furofuranoid structure group | |||||
Dendranlignan A | Dendranthema morifolium (Ramat.) | LPS-induced H9c2 cells | ↓TNF-α, ↓IL-6, ↓IFN-γ ↓p-cJUN, ↓p-P65, ↓p-IRF3 | 10 μM | [103] |
(+)-Diayangambin | Piper fimbriulatum | human mononuclear cells | ↓proliferation | 1.5 μM | [197] |
LPS-stimulated RAW264.7 macrophages | ↓PGE2 | 10 μM | |||
Fargesin | Magnolia fargesii | PMA-stimulated THP-1 | ↓iNOS, ↓COX-2, ↓IL-1β, ↓TNF-α, ↓AP-1, ↓NF-κB, ↓JNK | 5–20 μM | [198] |
Magnolia sp. | LPS-stimulated RAW264.7 | ↓iNOS, ↓COX-2, ↓NF-κB | 25 μM | [199] | |
Koreanaside A | Forsythia koreana | LPS-stimulated RAW 264.7 macrophages | ↓iNOS, ↓COX-2, ↓IL-6, ↓TNF-α, ↓p-IκBα, ↓p-TAK1 | 20–80 μM | [200] |
↓AP-1, ↓p-c-Fos, ↓p-p65, ↓NF-κB, ↓p-IKKα/β, ↓p-STAT1, ↓p-STAT3, ↓p-JAK1, ↓p-JAK2 | 40–80 μM | ||||
Phillygenin | Forsythia koreana | RAW 264.7 cells | ↓PGE2, ↓NO, ↓iNOS, ↓NF-κB | 1–100 μM | [201] |
Pinoresinol | Synthetic | IL-1β-stimulated Caco-2 cells | ↓PGE2, ↓MCP-1, ↓NF-κB | 50–100 μM | [202] |
↓IL-6 | 10–100 μM | ||||
Pinoresinol diglucoside | Eucommia ulmoides | oxLDL-induced HUVEC cytotoxicity | ↓eNOS, ↓p-p38MAPK, ↓p-NF-κB p65 | 1 μM | [109] |
Sesamin | Sesamum indicum Linn. | oxLDL-induced HUVECs cytotoxicity | ↓NF-κB, ↓IL-8 | 12.5–100 μM | [110] |
FPR-transfected ETFR cells, THP1 cells | ↓cell migration, ↓NF-κB activation, ↓ERK1/2 phosphorylation | 6.25–50 μM | [203] | ||
KA-induced PC12 and BV-2 cells | ↓ERK1/2, ↓p38 MAPK, ↓COX-2 | 10–50 μM | [111] | ||
RPMC | ↓histamine release | 25–100 μM | [204] | ||
HMC-1 | ↓TNF-α, ↓IL-6, ↓p38 MAPK, ↓NF-κB | ||||
Synthetic | RLE-6TN and L2 cells | ↑A20, ↑TAX1BP1 | 10 μM | [205] | |
epi-Sesamin | Asarum siebodlii | HUVEC | ↓EPCR shedding | 1–10 μM | [206] |
Syringaresinol | Perovskiaatriplicifolia Benth | RBL-1 leukemia cells | ↓leukotriene C4 release | IC50 7.9 ± 0.04 μM | [196] |
Rubia philippinensis | LPS-stimulated RAW 264.7 cells | ↓iNOS, ↓COX-2, ↓TNF-α, ↓IL-1β, ↓IL-6, ↓PGE2, ↓ERK1/2, ↓JNK, ↓p38 MAPK | 25, 50, 100 μM | [207] | |
High glucose-treated NRVM | ↓TNF-α, ↓IL-6, ↓IL-1β, ↓TGF-β, ↓p-Smad2/3 | 50, 100 μM | [116] | ||
LPS+ ATP-treated H9c2 cells | ↓IL-1β, ↓IL-18, ↑SIRT1 expression, ↓NLRP3 inflammasome activation | 100 μM | [208] | ||
Albiziae cortex | BV2 microglia cells | ↓TNF-α, ↓IL-6, ↓IL-1β, ↓COX-2, ↓NO, ↑M2 phenotype, ↓NF-κB | 25, 50, 100 μM | [209] |
3.4. Dibenzylbutane Skeletons
3.4.1. Nordihydroguaiaretic Acid (NDGA) and Its Derivatives
3.4.2. Meso-Dihydroguaiaretic Acid
3.4.3. Secoisolariciresinol and Its Derivatives
Lignan | Source | Model | Target | Dose, Road | Ref. |
---|---|---|---|---|---|
Arylnaphthalene structure group | |||||
Sevanol | Thymus armeniacus | CFA-induced thermal hyperalgesia | ↑withdrawal latency of inflamed hind paw | 1–10 mg/kg of mice, i.v. | [119] |
Synthetic | CFA-induced paw edema | ↓paw edema | 0.1–1 mg/kg of mice, i.m., i.n., p.o. | [120,121] | |
Aryltetralin structure group | |||||
Podophyllotoxin | Synthetic (G-003M) | TGR-exposed model | ↑survival, ↓NO, ↓IL-6, ↓TNF-α, ↓TGF-β1 | 5 mg/kg of mice, i.m. | [122] |
Synthetic, conjugated with PAA dendrimer | HCC-induced model | ↓IL-6, ↓NF-κB, ↓α-SMA, ↓TGF-β | 10, 20 mg/kg of mice, p.o. | [123] | |
Sauchinone | Saururus chinensis | OVA-induced asthma model | ↓neutrophil, lymphocyte, eosinophil infiltration in BALF, ↓IL-5, ↓IL-13, ↓Th2 cell development | 10, 100 mg/kg of mice, i.p. | [126] |
Dibenzocyclooctadiene structure group | |||||
Gomisin A | Schisandra chinensis Baill. | CCl4-induced hepatotoxicity | ↓TNF-α, ↓IL-1β, ↓iNOS, ↓NF-κB, ↓p-IκB | 50–100 mg/kg of rat, i.p. | [127] |
Gomisin N | Schisandra chinensis Baill. | ethanol-induced liver injury | ↓NF-κB p65, ↑IκB, ↓TNF-α, ↓IL-6, ↓MCP-1 | 5–20 mg/kg of mice, p.o. | [38] |
Schisandrin A | Schisandra chinensis (Turcz.) Baill. | LPS-treated model | ↓NO level | 100–200 mg/kg of mice, i.p. | [173] |
carrageenan-induced paw edema | ↓paw edema volume | ||||
xylene-induced ear edema | ↓ear edema degree | 25–50 mg/kg of mice, p.o. | [174] | ||
carrageenan-induced paw edema | ↓paw edema volume ↓TNF-α, ↓IL-1β, ↓MPO, ↓p-p65NF-κB, ↓p-IκB, ↓TLR4 | 25–50 mg/kg of mice, p.o. | |||
Schisandrin B | Synthetic | Con A-induced lymphocytes | ↓IL-2, ↓IL-4, ↓IL-6, ↓IFN-γ | 80 mg/kg of mice, i.p. | [46] |
myocardial infarction model | ↓in left ventricular end-systolic and end-diastolic diameter, ↓heart weight/body weight ratio, ↓infarct size, ↓NF-κB, ↓TGF-β1, ↓TNF-α | 80 mg/kg of mice, i.g. | [179] | ||
Aβ-infused model | ↓COX-2, ↓iNOS, ↓TNF-α, ↓IL-1β, ↓IL-6 | 25–50 mg/kg of rat, i.g. | [132] | ||
I/R injury model | ↓IL-1β, ↓TNF-α, ↓p-p38MAPK, ↓p-ERK1/2, ↓NF-κB p65 | 80 mg/kg of rat, p.o. | [134] | ||
TSCI model | ↓NF-κB p65, ↓TNF-α | 50 mg/kg of rat, p.o. | [133] | ||
IL-1β-induced rat chondrocytes | ↓IL-6, ↓iNOS, ↓MMP3, ↓MMP13, ↓NF-κB, ↓MAPK | 50 μM, i.a. | [180] | ||
STZ-induced diabetes | ↑IκBα, ↓VCAM-1, ↓TNF-α | 20 mg/kg of mice, p.o. | [135] | ||
Ang II-induced vascular injury model | ↓α-SMA, ↓p-Smad2/3, ↑VE-cadherin | 20 mg/kg of mice, p.o. | [176] | ||
DSS induced colitis | ↓TNF-α, ↓IL-6, ↓IL-18, ↓IL-1β, ↓NLRP3, ↑p-AMPK | 10 mg/kg of mice, i.p. | [177] | ||
Schisantherin A | Synthetic | MCAO/R-induced brain injury model | ↓IL-1β, ↓IL-6, ↓p-IκBα, ↓NF-κB, ↓p-ERK, ↓p-JNK, ↓p-p38, ↓TLR4, ↓C5aR1 | 5–10 mg/kg of rat, i.g. | [142] |
LPS-induced acute kidney injury | ↓accumulation neutrophils and T-lymphocytes, ↓NF-κB, ↓TNF-α, ↓Rantes | 40 mg/kg of mice, i.p. | [55] | ||
Dibenzylbutane structure group | |||||
Meso-dihydroguaiaretic acid | Machilusphilippinensis Merr. | LPS-induced ARDS model | ↓MPO, ↓4-HNE, ↓elastase accumulation | 30 mg/kg of mice, i.p. | [58] |
Nordihydroguaiaretic acid | Synthetic | TPA-treated model | ↓LPO level, ↓XOD, ↓MPO | 15–25 μM, shaved area of dorsal skin | [64] |
spinal cord injury | ↓MPO, ↓TNF-α, ↓IL-1β | 30 mg/kg of rat, i.p. | [211] | ||
leptin-deficient (ob/ob) mice | ↑PPARα, ↑p-AMPK ↑fatty acid oxidation pathway | 0.83 g/kg, 2.5 g/kg, diet | [212] | ||
CLP-induced sepsis | ↓lung edema, ↓lactate, ↓blood urea nitrogen, ↓histologic lung injury | 20 mg/kg of rat, i.p. | [213] | ||
Secoisolariciresinol diglucoside | Synthetic | CLP-induced sepsis | ↓p-IκBα, ↓NF-κΒ | 100 mg/kg of mice, i.p. | [76] |
BaP-injured model | ↓MPO, ↓NO level, ↓TNF-α, ↓IL-6, ↓IL-1β, ↓NF-κB | 100 mg/kg of mice, i.g. | [149] | ||
Dibenzylbutyrolactone structure group | |||||
Arctigenin | Forsythia fructus | OVA-induced asthma model | ↓PDE | 10–100 μM | [186] |
48/80-induced RPMCs | ↓histamine release | 10 μM | |||
IgE-rich mouse serum-induced PCA skin model | ↓amount of Evans blue leakage | 15–45 mg/kg of rat, p.o. | |||
anti-rat rabbit serum antibody-induced RCA skin model | ↓skin edema | ||||
SRBC-induced Arthus reaction model | ↓footpad thickness, ↓hemolysis tier, ↓hemagglutinin titer, ↓plaque-forming cells | 15–45 mg/kg of mice, p.o. | |||
SRBC-induced DTH model | ↓footpad thickness, ↓rosette-forming cells | ||||
DNFB/PC-induced contact dermatitis | ↓ear edema | 0.1–1 mg/ear of mice | |||
Arctium lappa Linn. | LPS-/PGN-stimulated peritoneal macrophages | ↓IL-6, ↓TNF-α, ↓IL-1β, ↑IL-10, ↑CD204, ↓p-PI3K, ↓p-Akt, ↓p-p65, ↓p-IKKβ | 10–20 μM | [216] | |
LPS-/PGN-induced model | ↓TNF-α, ↓IL-1β | 5 mg/kg of mice, i.p. | |||
TNBS-induced colitic model | ↓IL-6, ↓TNF-α, ↓IL-1β, ↓MPO, ↑IL-10, ↓p-PI3K, ↓p-Akt, ↓p-p65 | 30–60 mg/kg of mice, p.o. | |||
acetic acid-induced chronic ulcer model | ↓TNF-α, ↓IL-6, ↑IL-10, ↓CRP | 0.05–0.45 mg/kg of rat, p.o. | [151] | ||
LPS-induced acute inflammation model | ↓CD86, ↓IL-6, ↓IL-12, ↓TNF-α, ↓IL-1β, ↑IL-10, ↑G-MDSCs, ↓M-MDSCs, ↓IRF8, ↑miR-127-5p, ↓M1 macrophage polarization, ↑Arg-1, ↑iNOS | 50 mg/kg of mice, i.p. | [187] | ||
Synthetic | JEV-infected model | ↓iNOS, ↓TNF-α, ↓IFN-γ, ↓MCP-1, ↓IL-6, ↓p-p38 MAPK, ↓p-c-Jun ↓p-ERK-1/2, ↑p-Akt | 10 mg/kg of mice, i.p. | [152] | |
LPS-injured model | ↓nitrate/nitrite ratio, ↓iNOS, ↓TNF-α, ↓IL-6, ↓MIP-2, ↓p-ERK1/2, ↓p-JNK, ↓p-p38 | 50 mg/kg of mice, i.p. | [153] | ||
EAE model | ↓IFN-γ, ↓T-bet, ↓IL-17, ↓ROR-γt, ↓Th1, ↓Th17 | 5–10 mg/kg of mice, i.p. | [217] | ||
ConA-induced acute hepatitis | ↑IL-4, ↓F4/80, ↓CD49b, ↓CD4 T cells | 5–10 mg/kg of mice, i.p. | [188] | ||
AMI model | ↓iNOS, ↓COX-2, ↓IL-1β, ↓IL-6, ↓p-ERK1/2 | 100–200 μmol/kg of rat | [155] | ||
BLM-induced skin fibrosis model | ↓TGF-β1, ↓IL-1β, ↓IL-4, ↓IL-6, ↓TNF-α, ↓MCP-1 | 3 mg/kg of mice, i.p. | [156] | ||
DMM model | ↓cartilage erosion, ↓hypocellularity, ↓proteoglycan loss | 30 mg/kg of mice, p.o. | [189] | ||
imiquimod-induced murine psoriasis model | ↑p-CREB, ↑cAMP, ↑IL-10, ↓TNF-α, IFN-γ, ↓COX-2, ↓iNOS, ↓IL-2, ↓IL-6, ↓IL-12, ↓IL-17, ↓IL-22, ↓IL-23, ↓IL-27 | 5% cream | [190] | ||
silicosis model | ↓TGF-β, ↓TLR-4 | 30–60 mg/kg of rat, i.g. | [88] | ||
cadmium-intoxicated model | ↓NF-κB p65, ↓TNF-α, ↓IL-1β | 80 mg/kg of rat, i.g. | [157] | ||
Hinokinin | Synthetic | high-fat diet/STZ-induced type 2 diabetic | ↓TLR 4, ↓MYD88, ↓NF-κB p65, ↑IKBα, ↓TNF-α, ↓IL-1β, ↓p38, ↓ERK 1/2, ↓JNK, ↓MEK | 20–40 mg/kg of mice, p.o. | [158] |
Matairesinol | Synthetic | IRBP/CFA-induced EAU model | ↓T17 cells, ↓IL-17A, ↓IL-17F, ↓IL-21, ↓GM-CSF, ↓IRF-4, ↓Hif1, ↓Batf, ↓ROR-γt, ↓TNF-α | 1 mg/kg of mice, i.p. | [192] |
CLP-induced sepsis | ↓TNF-α, ↓IL-1β, ↓IL-6, ↓IFN-γ, ↓IL- 8, ↓MCP1, ↓MAPK, ↓JNK, ↓NF-κB | 5–20 mg/kg of rat, p.o. | [93] | ||
Nortrachelogenin | Synthetic | carrageenan-induced paw edema | ↓paw edema volume | 100 mg/kg of mice, i.p. | [194] |
Furanoid structure group | |||||
Nectandrin B | Guaiacum officinale L. | IL-1β-treated rat hepatocytes | ↓NO level | IC50 43.4 μM | [218] |
Taxiresinol | Taxus baccata Linn. | carrageenan-induced paw edema | ↓paw edema volume | 100 mg/kg of mice, p.o. | [219] |
Furofuranoid structure group | |||||
Acanthoside B | Salicornia europaea Linn. | Amnesic AD-like model | ↓iNOS, ↓COX-2, ↓TNF-α, ↓IL-1β, ↓IL-6, ↑IL-10 | 10, 20 mg/kg of mice, p.o. | [220] |
(+)-Diayangambin | Piper fimbriulatum | carrageenan-induced paw edema | ↓paw volume, ↓prostaglandin E2 | 40 mg/kg of mice, p.o. | [197] |
Fargesin | Magnolia sp. | DSS-induced colitis | ↓inflammatory infiltration, ↓MPO, ↓TNF-α, ↓NO, ↑IκBα, ↓NF-κB | 50 mg/kg of mice, p.o. | [199] |
Synthetic | ApoE−/− model | ↓macrophage infiltration, ↑M2 phenotype polarization, ↓TNF-α, ↓IL-1β, ↓IL-6, ↓MCP-1, ↑IL-10 | 50 mg/kg of mice, p.o. | [221] | |
Isoeucommin A | Eucommia ulmoides Oliv. | STZ-induced diabetic nephropathy | ↓immune infiltration, ↓TNF-α, ↓IL-1β, ↓IL-6 | 2.5–10 mg/kg of rat, i.v. | [104] |
Koreanaside A | Forsythia koreana | DSS-induced acute colitis | ↓iNOS, ↓COX-2, ↓IL-6, ↓TNF-α ↓p-c-Fos, ↓p-p65, ↓p-STAT1, ↓p-STAT3 | 5–20 mg/kg of mice, i.p. | [200] |
Phillygenin | Forsythia koreana | carrageenan-induced paw edema | ↓paw volume | 12.5–100 mg/kg of mice, i.p. | [201] |
Forsythia fructus | CCl4-induced liver fibrosis | ↓LPS, ↓MIP-1, ↓TNF-α, ↓IL-1β, ↓IL-6, ↓immune infiltration | 20, 40 mg/kg of mice, i.g. | [222] | |
Pinoresinol diglucoside | Synthetic | Aβ-infused model | ↓TLR4, ↓NF-κB p65, ↓TNF-α, ↓IL-1β | 5–10 mg/kg of mice, i.g. | [160] |
MCAO model | ↓TNF-α, ↓IL-1β, ↓IL-6, ↓p-IKKβ, ↓p-IkBα, ↑cNF-κB p65, ↓p-p65 | 5–10 mg/kg of mice, i.v. | [161] | ||
Sesamin | Sesamum indicum Linn. | fMLF-induced inflammation in a murine air-pouch model | ↓leukocyte infiltration | 12 mg/kg of mice, i.p. | [203] |
PCA model | ↓PCA reaction | 50–200 mg/kg of rat, p.o. | [204] | ||
LPS-treated model | ↓TNF-α, ↓MCP-1, ↓IL-1β | 10 mg/kg of rat, p.o. | [168] | ||
LPS-treated model | ↓NF-κB, ↓TLR4, ↓Cox2, ↓TNF-α, ↓IL-6 | 100 mg/kg of mice, p.o. | [169] | ||
DSS-induced colitis model | ↓IL-6, ↓IL-1β, ↓TNF-α | 50–100 mg/kg of mice, i.g. | [113] | ||
cisplatin-injured model | ↓TNF-α, ↓IL-1β, ↓TGF-β1, ↓MPO | 5 mg/kg of rat, p.o. | [170] | ||
Synthetic | CCl4-induced hepatotoxicity model | ↓TNF-α | 60–120 mg/kg of mice, p.o. | [164] | |
carrageenan-induced lung inflammation | ↑A20, ↑TAX1BP1, ↓IL-6, ↓IL-8, ↓IL-1β, ↓TNF-α, ↓MIP-2, ↓MPO, ↓β-glucuronidase, ↓p-p65, ↓TRAF6 | 50–100 mg/kg of rat, p.o. | [205] | ||
fluoride-exposed model | ↓TNF-α | 0.5–1 g/kg of carp, diet | [165] | ||
Syringaresinol | Rubia philippinensis | carrageenan-induced paw edema model | ↓paw edema volume | 50 mg/kg of mice, p.o. | [207] |
CLP-induced sepsis | ↓TNF-α, ↓IL-6, ↓IL-18, ↓IL-1β | 50 mg/kg of mice, p.o. | [208] | ||
STZ-induced type 1 diabetic model | ↓macrophage, monocyte, neutrophil infiltration in myocardium, ↓TNF-α, ↓IL-6, ↓IL-1β | 25 mg/kg of mice, p.o. | [116] | ||
Albiziae cortex | LPS-treated model | ↓IL-6, ↓IL-1β, ↓TNF-α, ↓COX-2, ↓iNOS, ↓microglia activation | 60 mg/kg of mice, p.o. | [209] |
3.5. Dibenzylbutyrolactone and Dibenzylbutyrolactol Skeletons
3.5.1. Arctigenin
3.5.2. Carissanol
3.5.3. Hinokinin
3.5.4. Matairesinol and Its Derivatives
3.5.5. Nortrachelogenin
3.6. Furanoid Skeletons
3.6.1. Lariciresinol
3.6.2. Nectandrin B
3.6.3. Olivil
3.6.4. Taxiresinol
3.7. Furofuran Skeletons
3.7.1. Acanthoside B
3.7.2. Dendranlignan A
3.7.3. Diayangambin
3.7.4. Fargesin
3.7.5. Isoeucommin A
3.7.6. Koreanaside A
3.7.7. Phylligenin
3.7.8. Pinoresinol and Its Derivatives
3.7.9. Sesamin
3.7.10. Syringaresinol
4. Main Approaches for Lignan Synthesis
4.1. Oxidative Dimerization
4.2. Classical Cyclization and Non-Phenolic Oxidative Dimerization
5. Conclusions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Osmakov, D.I.; Kalinovskii, A.P.; Belozerova, O.A.; Andreev, Y.A.; Kozlov, S.A. Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities. Int. J. Mol. Sci. 2022, 23, 6031. https://doi.org/10.3390/ijms23116031
Osmakov DI, Kalinovskii AP, Belozerova OA, Andreev YA, Kozlov SA. Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities. International Journal of Molecular Sciences. 2022; 23(11):6031. https://doi.org/10.3390/ijms23116031
Chicago/Turabian StyleOsmakov, Dmitry I., Aleksandr P. Kalinovskii, Olga A. Belozerova, Yaroslav A. Andreev, and Sergey A. Kozlov. 2022. "Lignans as Pharmacological Agents in Disorders Related to Oxidative Stress and Inflammation: Chemical Synthesis Approaches and Biological Activities" International Journal of Molecular Sciences 23, no. 11: 6031. https://doi.org/10.3390/ijms23116031