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. 2021 Sep 8;10(9):1431. doi: 10.3390/antiox10091431

Table 4.

Meroterpenoids from macroalgae with antioxidant activity.

Compound Isolation Source Assay/Activity Reference
125 Cymopolia barbata
(Chlorophyta, Ulvophyceae, Dasycladales)		 DPPH scavenging: strong
exogenous ROS scavenging in TPA-treated HL-60 cells (DCFH-DA): IC50 = 4.0 μM		 [91]
126 C. barbata
(Chlorophyta, Ulvophyceae, Dasycladales)		 DPPH scavenging: strong
exogenous ROS scavenging in TPA-treated HL-60 cells (DCFH-DA): IC50 >14.6 μM		 [91]
127 Cystoseira crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging: 94.1% at 230 μM
O2− generation (PCL assay)
TBARS assay: 66.8% inhibition at 164 μM		 [177]
128 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging activity: 92.5% at 230 μM
O2− generation (PCL assay)
TBARS assay: 66.5% inhibition at 164 μM 		[177]
129 Cystoseira usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 33.3 ± 2.3 μM; 0.78 TE [178]
130 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 51.6 ± 4.8 μM; 0.50 TE [178]
131 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 44.7 ± 1.1 μM; 0.58 TE [178]
132 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 55.9 ± 9.9 μM; 0.46 TE [178]
133 Dictyopteris undulata
(Ochrophyta, Phaeophyceae, Dictyotales)		 DPPH scavenging: IC50 = 71 μM [179]
134 D. undulata
(Ochrophyta, Phaeophyceae, Dictyotales)		 expression of phase-2 enzymes (i.e., NQO1, GSH S-transferase, HO-1 and PRDX4)
Nrf2/ARE signaling pathway
oxidative stress in HT22 hippocampal neuronal cells		 [180]
135 D. undulata
(Ochrophyta, Phaeophyceae, Dictyotales)		 DPPH scavenging: IC50 = 121 μM [179]
136 G. salicornia
(Rhodophyta, Florideophyceae, Gracilariales)		 ABTS+ scavenging: IC50 = 1.88 ± 0.02 mM
DPPH scavenging: IC50 = 1.51 ± 0.01 mM		 [181]
137 G. salicornia
(Rhodophyta, Florideophyceae, Gracilariales)		 ABTS+ scavenging: IC50 = 1.96 ± 0.01 mM
DPPH scavenging: IC50 = 1.85 ± 0.02 mM		 [181]
138 G. salicornia
(Rhodophyta, Florideophyceae, Gracilariales)		 ABTS+ scavenging: IC50 = 1.57 ± 0.02 mM
DPPH scavenging: IC50 = 1.33 ± 0.01 mM		 [181]
139 D. undulata
(Ochrophyta, Phaeophyceae, Dictyotales)		 DPPH scavenging: IC50 = 145 μM [179]
140 G. salicornia
(Rhodophyta, Florideophyceae, Gracilariales)		 ABTS+ scavenging: IC50 = 1.50 mM
DPPH scavenging: IC50 = 1.40 mM		 [182]
141 G. salicornia
(Rhodophyta, Florideophyceae, Gracilariales)		 ABTS+ scavenging: IC50 = 1.33 mM
DPPH scavenging: IC50 = 1.17 mM		 [182]
142 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 25.5 μM
lipid peroxidation in rat liver: IC50 = 0.26 μM		 [183]
143 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 3.0% at 0.23 mM
lipid peroxidation in rat liver: IC50 = 2.22 μM		 [184]
144 Cystoseira abies-marina
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 29% at 1.06 mM [185]
145 C. abies-marina
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 30% at 1.02 mM [185]
146 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging: 94.4% at 230 μM
O2− radical generation (PCL assay)
TBARS: 70.8% inhibition at 164 μM		 [177]
147 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.14 mM
DPPH scavenging: 95.4% at 230 μM
O2− radical generation (PCL assay): 1.35
TBARS: 71.8% inhibition at 164 μM		 [177]
148 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging: 96.1% at 230 μM
O2− radical generation (PCL assay)
TBARS: 68.9% inhibition at 164 μM		 [177]
149 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging: 95.5% at 230 μM
O2− radical generation (PCL assay)
TBARS: 70.3% inhibition at 164 μM		 [177]
150 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.37 mM
DPPH scavenging: 95.5% at 230 μM
O2− radical generation (PCL assay): 1.39
TBARS: 72.2% inhibition at 164 μM		 [177]
151 C. crinita 
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.09 mM
DPPH scavenging: 95.7% at 230 μM
O2− radical generation (PCL assay): 0.72
TBARS: 71.1% inhibition at 164 μM		 [177]
152 C. crinita 
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.09 mM
DPPH scavenging: 96.4% at 230 μM
O2− radical generation (PCL assay): 0.59
TBARS: 73.7% inhibition at 164 μM		 [177]
153 C. crinita 
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.09 mM
DPPH scavenging: 96.7% at 230 μM
O2− radical generation (PCL assay): 0.51
TBARS: 73.4% inhibition at 164 μM		 [177]
154 C. crinita 
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.08 mM
DPPH scavenging: 65.4% at 230 μM
O2− radical generation (PCL assay): 1.06
TBARS: 74.9% inhibition at 164 μM		 [177]
155 C. crinita 
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.28 mM
DPPH scavenging: 95.8% at 230 μM
O2− radical generation (PCL assay): 0.79
TBARS: 74.6% inhibition at 164 μM		 [177]
156 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.77 TE [186]
157 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 24.5 ± 1.6 μM; 1.06 TE [178]
158 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.77 TE [186]
159 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 26.3 ± 2.3 μM; 0.98 TE [178]
160 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.87 TE [186]
161 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 33.1 ± 5.1 μM; 0.78 TE [178]
162 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.67 TE [186]
163 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.81 TE [186]
164 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 43.1 ± 3.1 μM; 0.60 TE [178]
165 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.53 TE [186]
166 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.37 TE [186]
167 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.66 TE [186]
168 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.45 TE [186]
169 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.65 TE [186]
170 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.50 TE [186]
171 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: 0.62 TE [186]
172 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 24.4 ± 0.9 μM; 1.06 TE [178]
173 C. usneoides
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: IC50 = 22.5 ± 2.1 μM; 1.15 TE [178]
174 Sargassum siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.54 μM [187]
175 Sargassum elegans, S. siliquastrum, Sargassum thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.40; 46.9 μM
ONOO scavenging: 78.03% at 23.4 μM
ONOO− derived from SIN-1 scavenging: 100% at 23.4 μM
electrochemistry-guided isolation of antioxidant metabolites (using square wave and cyclic voltammetry methods)		 [157,187,188,189]
176 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 52.6% inhibition at 143.6 μM
lipid peroxidation in rat liver: IC50 = 63.6 μM		 [184]
177 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 32.3% inhibition at 144.0 μM
lipid peroxidation in rat liver: IC50 = 1.66 μM		 [184]
178 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.27 μM [187]
179 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.25 μM [187]
180 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.68 μM [187]
181 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.64 μM [187]
182 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.62 μM [187]
183 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 0.21 μM [187]
184 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 23.3 μM [187]
185 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 26.1 μM [187]
186 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 25.4 μM [187]
187 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 37.9 μM [187]
188 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 35.4 μM [187]
189 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 18.7 μM [187]
190 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 25.9 μM [187]
191 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 30.4 μM [187]
192 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 47.9 μM [187]
193 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 26.3 μM [187]
194 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 25.1 μM [187]
195 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 933.3 μM
lipid peroxidation in rat liver: IC50 = 2.33 μM		 [183]
196 S. elegans
(Ochrophyta, Phaeophyceae, Fucales)		 electrochemistry-guided isolation of antioxidant metabolites (using square wave and cyclic voltammetry methods) [157]
197 S. elegans, S. micracanthum, S. thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 63.6; 100.2 μM; 69.82% at 250 μM
ONOO scavenging: 64.18% at 23.6 μM
ONOO− derived from SIN-1 scavenging activity: 75.39% at 23.6 μM
electrochemistry-guided isolation of antioxidant metabolites (using square wave and cyclic voltammetry methods)		 [157,188,189,190]
198 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging
DPPH scavenging: 29.0% at 230 μM
O2− generation (PCL assay)
TBARS: 43.3% inhibition at 164 μM		 [177]
199 C. crinita
(Ochrophyta, Phaeophyceae, Fucales)		 ABTS+ scavenging: TEAC = 0.30 mM
DPPH scavenging: 38.6% at 230 μM
O2− generation (PCL assay): 1.41
TBARS: 54.4% inhibition at 164 μM		 [177]
200 C. barbata
(Ochrophyta, Phaeophyceae, Fucales)		 antioxidant activity against ROS and reactive nitrogen species [141,183,184,189]
201 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 90.0% at 0.29 mM [191]
202 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 87.4% at 0.29 mM [191]
203 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 H2O2-induced lipid peroxidation in HT 1080 cells
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA) in HT 1080 cells		 [192]
204 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 90.5% at 0.24 mM [191]
205 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 89.6% at 0.23 mM
H2O2-induced lipid peroxidation in HT 1080 cells
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA) in HT 1080 cells: 67.2% decrease at 11.7 μM		 [191,192]
206 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 87.3% at 0.23 mM
H2O2-induced lipid peroxidation in HT 1080 cells
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA) in HT 1080 cells: 87.2% decrease at 11.7 μM		 [191,192]
207 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 88.2% at 0.23 mM [191]
208 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 90.4% at 0.23 mM
expression of osteoclastic marker gene in RANKL-stimulated RAW264.7 cells (TRAP, CTSK, MMP9 and CTR)
NF-κB activation in RANKL-stimulated RAW264.7 cells
osteoclast differentiation in RANKL-stimulated RAW264.7 cells
phosphorylation of MAPKs in RANKL-stimulated RAW264.7 cells		 [191,193]
209 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 89.2% at 0.23 mM
H2O2-induced lipid peroxidation in HT 1080 cells
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA assay) in HT 1080 cells		 [191,192]
210 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 87.8% at 0.23 mM [191]
211 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 90.4% at 0.23 mM [191]
212 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 89.1% at 0.23 mM [191]
213 S. micracanthum
(Ochrophyta, Phaeophyceae, Fucales)		 NADPH-dependent lipid peroxidation in rat microsomes: IC50 = 0.65 μM [194]
214 S. micracanthum, S. thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 75.4 μM; 78.85% at 250 μM
ONOO scavenging: 92.69% at 23.6 μM
ONOO− derived from SIN-1 scavenging: 99.51% at 23.6 μM		 [188,189,190]
215 S. thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 82.9 μM [189]
216 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 H2O2-induced lipid peroxidation in HT 1080 cells: 43.2% at 112.0 μM
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA) in HT 1080 cells		 [192]
217 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 H2O2-induced lipid peroxidation in HT 1080 cells: 38.9% at 112.0 μM
intracellular GSH level in HT 1080 cells
intracellular ROS generation (DCFH-DA) in HT 1080 cells		 [192]
218 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 88.8% at 0.24 mM [191]
219 S. thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 67.8 μM
ONOO scavenging: 60.0% at 11.3 μM
ONOO− derived from SIN-1 scavenging: 98.6% at 11.3 μM		 [195]
220 S. thunbergii
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: IC50 = 70.0 μM
ONOO scavenging: 57.1% at 11.3 μM
ONOO− derived from SIN-1 scavenging: 90.6% at 11.3 μM		 [195]
221 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 90.1% at 0.24 mM [191]
222 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 88.7% at 0.23 mM [191]
223 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 89.2% at 0.24 mM [191]
224 S. siliquastrum
(Ochrophyta, Phaeophyceae, Fucales)		 DPPH scavenging: 88.7% at 0.24 mM [191]

ABTS+: 2,2’-azino-bis (3-ethyl benzothiazoline-6-sulfonic acid) diammonium salt; ARE: antioxidant response element; CTR: calcitonin receptor; CTSK: cathepsin K; DCFH-DA: cell-based 2′,7′-dichlorodihydrofluorescein diacetate antioxidant assay; DPPH: 1,1-diphenyl-2-picrylhydrazyl free radical; GSH: glutathione; HO-1: heme oxygenase-1; HT 1080: human fibrosarcoma cell line; IC50: half maximal inhibitory concentration; MMP9: matrix metalloproteinase 9; NADPH: nicotinamide adenine dinucleotide phosphate; NQO1: NADPH quinone oxidoreductase 1; Nrf2: nuclear factor erythroid 2-related factor 2; ONOO−: peroxynitrite; O2−: superoxide anion; PCL: photochemiluminescence; PRDX4: peroxyredoxin 4; RANKL: receptor activator of NF-κB ligand; ROS: reactive oxygen species; SIN-1: 3-morpholinosydnonimine; SOD: superoxide dismutase; TBARS: thiobarbituric acid reactive substances; TE: trolox equivalents; TEAC: trolox equivalence antioxidant capacity; TPA: 12-O-tetradecanoylphorbol 13-acetate; TRAP: tartrate-resistant acid phosphatase.