Table 2.
Biological activity of reported metabolites from Aspergillus ochraceus.
| Compound Name | Biological Activity | Assay, Organism or Cell Line | Biological Results | Ref. | |
|---|---|---|---|---|---|
| Compound | Positive Control | ||||
| 3R-Mellein (1) | Anti HCV protease | SPA | 35.0 µM (IC50) | - | [20] |
| Antioxidant | Spectrophotometry/DPPH | 25.0 µM (IC50) | l-ascorbic acid 20.0 μM (IC50) | [72] | |
| (3R,4S)-4-Hydroxymellein (2) | Antioxidant | Spectrophotometry/DPPH | 129.36 µM (IC50) | BHT 91.35 µM (IC50) | [21] |
| Spectrophotometry/ABTS | 140.23 µM (IC50) | Trolox 101.23 µM (IC50) | [21] | ||
| Spectrophotometry/FRAP | 11.96 µM (IC50) | Trolox 1.80 µM (IC50) | [21] | ||
| (R)-7-Hydroxymellein (4) | Antibacterial | Well diffusion/A. hydrophilia | 64.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 32.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 8.0 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| (R)-(–)-5-Bromomellein (5) | Antioxidant | Spectrophotometry/DPPH | 24.0 µM (IC50) | l-ascorbic acid 20.0 μM (IC50) | [72] |
| (±)-4,7-dihydroxymellein (6) | Antioxidant | Spectrophotometry/DPPH | 62.90 µM (IC50) | BHT 91.35 µM (IC50) | [21] |
| Spectrophotometry/ABTS | 70.92 µM (IC50) | Trolox 101.23 µM (IC50) | [21] | ||
| Spectrophotometry/FRAP | 2.53 µM (IC50) | Trolox 1.80 µM (IC50) | [21] | ||
| Ochratoxin B (18) | Cytotoxicity | MTT/A2780 | 3.0 µM (IC50) | Cisplatin 2.2 µM (IC50) | [17] |
| Flavacol (25) | Inhibition of mitochondrial NADH oxidase | SMP/NADH oxidase | 34.6 µM (IC50) | - | [86] |
| CJ-17,665 = Avrainvillamide (43) | Antibacterial | Microdilution/S. aureus | 12.5 μg/mL (MIC) | Vancomycin 1.56 μg/mL (MIC) | [88] |
| Microdilution/S. pyogenes | 12.5 μg/mL (MIC) | Vancomycin 0.39 μg/mL (MIC) | [88] | ||
| Microdilution/E. pyogenes | 25.0 μg/mL (MIC) | Vancomycin 12.5 μg/mL (MIC) | [88] | ||
| Cytotoxicity | MTT/HeLa | 1.1 μg/mL (IC90) | - | [88] | |
| Stephacidin A (44) | Cytotoxicity | MTT/PC-3 | 2.1 µM (IC50) | - | [89] |
| MTT/LNCaP | 1.0 µM (IC50) | - | [89] | ||
| MTT/A2780 | 4.0 µM (IC50) | - | [89] | ||
| MTT/A2780/DDP | 6.8 µM (IC50) | - | [89] | ||
| MTT/A2780/Tax | 3.6 µM (IC50) | - | [89] | ||
| MTT/HCT-116 | 2.1 µM (IC50) | - | [89] | ||
| MTT/HCT116/mdr+ | 6.7 µM (IC50) | - | [89] | ||
| MTT/HCT116/topo | 13.1 µM (IC50) | - | [89] | ||
| MTT/MCF-7 | 4.2 µM (IC50) | - | [89] | ||
| MTT/SKBR3 | 2.15 µM (IC50) | - | [89] | ||
| MTT/LX-1 | 4.22 µM (IC50) | - | [89] | ||
| Inhibition of mitochondrial NADH Oxidase | SMP/NADH oxidase | 13.0 µM (IC50) | - | [86] | |
| Anti-Parkinson’s disease | MPP+-induced SH-SY5Y cells | 2.45 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] | |
| Stephacidin B (45) | Cytotoxicity | MTT/PC-3 | 0.37 µM (IC50) | - | [89] |
| MTT/LNCaP | 0.06 µM (IC50) | - | [89] | ||
| MTT/A2780 | 0.33 µM (IC50) | - | [89] | ||
| MTT/A2780/DDP | 0.43 µM (IC50) | - | [89] | ||
| MTT/A2780/Tax | 0.26 µM (IC50) | - | [89] | ||
| MTT/HCT-116 | 0.46 µM (IC50) | - | [89] | ||
| MTT/HCT116/mdr+ | 0.46 µM (IC50) | - | [89] | ||
| MTT/HCT116/topo | 0.42 µM (IC50) | - | [89] | ||
| MTT/MCF-7 | 0.27 µM (IC50) | - | [89] | ||
| MTT/SKBR3 | 0.32 µM (IC50) | - | [89] | ||
| MTT/LX-1 | 0.38 µM (IC50) | - | [89] | ||
| Speramide A (46) | Antibacterial | 2-Fold dilution/ P. aeruginosa | 0.8 µM (MIC) | - | [23] |
| Notoamide B (53) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 5.31 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Notoamide C (54) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 7.39 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Notoamide F (55) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 2.98 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Notoamide I (56) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 2.30 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Versicolamide B (61) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 6.01 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Circumdatin A (64) | Antioxidant | Spectrophotometry/DPPH | 32.0 µM (IC50) | l-ascorbic acid 20.0 μM (IC50) | [72] |
| 2-Hydroxycircumdatin C (67) | Antioxidant | Spectrophotometry/DPPH | 9.9 µM (IC50) | BHT 88.2 µM (IC50) | [26] |
| Cytotoxicity | CTG/U251 | 8.95 µM (IC50) | Adramycin 0.19 µM (IC50) | [31] | |
| Circumdatin E (69) | Inhibition of Mitochondrial NADH Oxidase | SMP/NADH oxidase | 2.5 µM (IC50) | - | [86] |
| Circumdatin F (70) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 5.44 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Circumdatin G (71) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 7.39 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Circumdatin H (72) | Inhibition of Mitochondrial NADH Oxidase | SMP/NADH oxidase | 1.5 µM (IC50) | - | [86] |
| Circumdatin N (75) | Anti-Parkinson’s disease | MPP+-induced SH-SY5Y cells | 10.77 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Ochrazepine A (76) | Cytotoxicity | CTG/MV-4-11 | 3.94 µM (IC50) | Adramycin 0.16 µM (IC50) | [31] |
| CTG/K562 | 6.05 µM (IC50) | Adramycin 0.02 µM (IC50) | [31] | ||
| CTG/A673 | 3.10 µM (IC50) | Adramycin 0.13 µM (IC50) | [31] | ||
| CTG/U87 | 8.67 µM (IC50) | Adramycin 0.12 µM (IC50) | [31] | ||
| CTG/A549 | 9.62 µM (IC50) | Adramycin 0.10 µM (IC50) | [31] | ||
| CTG/N87 | 6.10 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/H1299 | 7.14 µM (IC50) | Adramycin 0.49 µM (IC50) | [31] | ||
| CTG/HUCCT1 | 11.32 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/B16F10 | 11.22 µM (IC50) | Adramycin 0.02 µM (IC50) | [31] | ||
| CTG/Karpass299 | 5.89 µM (IC50) | Adramycin 0.39 µM (IC50) | [31] | ||
| CTG/HEK-293F | 12.91 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/L02 | 27.42 µM (IC50) | Adramycin 0.10 µM (IC50) | [31] | ||
| Ochrazepine B (77) | Cytotoxicity | CTG/U251 | 9.91 µM (IC50) | Adramycin 0.19 µM (IC50) | [31] |
| CTG/HEK-293F | 73.96 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| Ochrazepine C (78) | Cytotoxicity | CTG/A673 | 8.24 µM (IC50) | Adramycin 0.13 µM (IC50) | [31] |
| CTG/U87 | 9.04 µM (IC50) | Adramycin 0.12 µM (IC50) | [31] | ||
| CTG/HepB3 | 10.28 µM (IC50) | Adramycin 17.58 µM (IC50) | [31] | ||
| CTG/HEK-293F | 73.03 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| Ochrazepine D (79) | Cytotoxicity | CTG/U251 | 8.26 µM (IC50) | Adramycin 0.19 µM (IC50) | [31] |
| CTG/HEK-293F | 54.58 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| Perlolyrine (84) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 9.97 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Ochracesol A (85) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 17.84 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| 6β,9α-Dihydroxy-14-p-nitrobenzoylcinnamolide (90) | Cytotoxicity | CCK-8/H1975 | 2.08 µM (IC50) | Trichostatin A 0.09 µM (IC50) | [32] |
| CCK-8/U937 | 1.95 µM (IC50) | Trichostatin A 0.05 µM (IC50) | [32] | ||
| CCK-8/K562 | 4.33 µM (IC50) | Trichostatin A 0.16 µM (IC50) | [32] | ||
| CCK-8/BGC823 | 2.32 µM (IC50) | Trichostatin A 0.08 µM (IC50) | [32] | ||
| CCK-8/Molt-4 | 2.39 µM (IC50) | Trichostatin A 0.03 µM (IC50) | [32] | ||
| CCK-8/MCF-7 | 4.25 µM (IC50) | Trichostatin A 0.06 µM (IC50) | [32] | ||
| CCK-8/A549 | 2.41 µM (IC50) | Trichostatin A 0.05 µM (IC50) | [32] | ||
| CCK-8/HeLa | 6.12 µM (IC50) | Trichostatin A 0.10 µM (IC50) | [32] | ||
| CCK-8/HL-60 | 2.44 µM (IC50) | Trichostatin A 0.03 µM (IC50) | [32] | ||
| CCK-8/Huh-7 | 3.28 µM (IC50) | Trichostatin A 0.09 µM (IC50) | [32] | ||
| CCK-8/ACHN | 11.0 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] | ||
| CCK-8/OS-RC-2 | 8.2 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 4.3 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| Antiviral | CCK-8/H3N2 | 17.0 µM (IC50) | Oseltamivir A 0.008 µM (IC50) | [32] | |
| CCK-8/EV71 | 9.4 µM (IC50) | Oseltamivir A 0.06 µM (IC50) | [32] | ||
| Insulicolide A (91) | Cytotoxicity | CCK-8/H1975 | 4.63 µM (IC50) | Trichostatin A 0.09 µM (IC50) | [32] |
| CCK-8/U937 | 3.97 µM (IC50) | Trichostatin A 0.05 µM (IC50) | [32] | ||
| CCK-8/K562 | 4.76 µM (IC50) | Trichostatin A 0.16 µM (IC50) | [32] | ||
| CCK-8/BGC823 | 2.78 µM (IC50) | Trichostatin A 0.08 µM (IC50) | [32] | ||
| CCK-8/Molt-4 | 2.11 µM (IC50) | Trichostatin A 0.03 µM (IC50) | [32] | ||
| CCK-8/MCF-7 | 6.08 µM (IC50) | Trichostatin A 0.06 µM (IC50) | [32] | ||
| CCK-8/A549 | 2.86 µM (IC50) | Trichostatin A 0.05 µM (IC50) | [32] | ||
| CCK-8/HeLa | 6.35 µM (IC50) | Trichostatin A 0.10 µM (IC50) | [32] | ||
| CCK-8/HL-60 | 2.34 µM (IC50) | Trichostatin A 0.03 µM (IC50) | [32] | ||
| CCK-8/Huh-7 | 2.35 µM (IC50) | Trichostatin A 0.09 µM (IC50) | [32] | ||
| CCK-8/ACHN | 1.5 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] | ||
| CCK-8/OS-RC-2 | 1.5 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 0.89 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| 14-O-Acetylinsulicolide A (92) | Cytotoxicity | CCK-8/ACHN | 4.1 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] |
| CCK-8/OS-RC-2 | 5.3 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 2.3 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| 9-Deoxyinsulicolide A (93) | Cytotoxicity | CCK-8/ACHN | 25.0 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] |
| CCK-8/OS-RC-2 | 30.0 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 20.0 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| Insulicolide B (94) | Cytotoxicity | CCK-8/ACHN | 30.0 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] |
| CCK-8/OS-RC-2 | 23.0 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 24.0 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| Insulicolide C (95) | Cytotoxicity | CCK-8/ACHN | 13.0 µM (IC50) | Sorafenib 3.4 µM (IC50) | [97] |
| CCK-8/OS-RC-2 | 11.0 µM (IC50) | Sorafenib 7.0 µM (IC50) | [97] | ||
| CCK-8/786-O | 14.0 µM (IC50) | Sorafenib 4.9 µM (IC50) | [97] | ||
| Penicillic acid (97) | Antibacterial | Well diffusion/A. hydrophilia | 1.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 32.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 0.5 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| Chlorohydroasperlactone A (100) | Antibacterial | Well diffusion/A. hydrophilia | 16.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 16.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 16.0 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| Asperochrin A (104) | Antibacterial | Well diffusion/A. hydrophilia | 8.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 16.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 8.0 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| Aspyrone (117) | Cytotoxicity | CTG/MV-4-11 | 2.54 µM (IC50) | Adramycin 0.16 µM (IC50) | [31] |
| CTG/K562 | 5.22 µM (IC50) | Adramycin 0.02 µM (IC50) | [31] | ||
| CTG/A673 | 8.55 µM (IC50) | Adramycin 0.13 µM (IC50) | [31] | ||
| CTG/N87 | 4.57 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/H1299 | 5.83 µM (IC50) | Adramycin 0.49 µM (IC50) | [31] | ||
| CTG/HUCCT1 | 9.79 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/B16F10 | 5.89 µM (IC50) | Adramycin 0.02 µM (IC50) | [31] | ||
| CTG/Karpass299 | 2.57 µM (IC50) | Adramycin 0.39 µM (IC50) | [31] | ||
| CTG/HepB3 | 5.48 µM (IC50) | Adramycin 17.58 µM (IC50) | [31] | ||
| CTG/HA431 | 5.92 µM (IC50) | Adramycin 0.17 µM (IC50) | [31] | ||
| CTG/143B | 6.32 µM (IC50) | Adramycin 0.10 µM (IC50) | [31] | ||
| CTG/MKN-45 | 5.79 µM (IC50) | Adramycin 0.20 µM (IC50) | [31] | ||
| CTG/H1975 | 2.99 µM (IC50) | Adramycin 0.09 µM (IC50) | [31] | ||
| CTG/Hl-60 | 6.89 µM (IC50) | Adramycin 0.21 µM (IC50) | [31] | ||
| CTG/DU145 | 5.61 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/SPC-A1 | 9.51 µM (IC50) | Adramycin 0.19 µM (IC50) | [31] | ||
| CTG/HEK-293F | 50.35 µM (IC50) | Adramycin 0.05 µM (IC50) | [31] | ||
| CTG/L02 | 14.20 µM (IC50) | Adramycin 0.10 µM (IC50) | [31] | ||
| Chlorohydroaspyrone A (118) | Antibacterial | Well diffusion/A. hydrophilia | 16.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 32.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 16.0 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| Chlorohydroaspyrone B (119) | Antibacterial | Well diffusion/A. hydrophilia | 16.0 μg/mL (MIC) | Chloramphenicol 4.0 μg/mL (MIC) | [71] |
| Well diffusion/V. anguillarum | 32.0 μg/mL (MIC) | Chloramphenicol 1.0 μg/mL (MIC) | [71] | ||
| Well diffusion/V. harveyi | 32.0 μg/mL (MIC) | Chloramphenicol 8.0 μg/mL (MIC) | [71] | ||
| Viomellein (132) | Cytotoxicity | MTT/L5178Y | 5.3 µM (IC50) | Kahalalide F 4.3 µM (IC50) | [17] |
| MTT/A2780 | 5.0 µM (IC50) | Cisplatin 2.2 µM (IC50) | [17] | ||
| (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (143) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 35.71 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Ochrasterone (150) | Antioxidant | DPPH | 189.10 µM (IC50) | BHT 91.35 µM (IC50) | [21] |
| ABTS | 60.21 µM (IC50) | Trolox 101.23 µM (IC50) | [21] | ||
| FRAP | 57.20 µM (IC50) | Trolox 1.80 µM (IC50) | [21] | ||
| Gymnasterone D (151) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 38.75 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Isocyathisterol (152) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 46.18 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Herbarulide (153) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 37.67 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Demethylincisterol A2 (154) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 49.53 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |
| Clavatol (156) | Antioxidant | DPPH | 30.0 µM (IC50) | l-ascorbic acid 20.0 μM (IC50) | [72] |
| Di-(2-ethylhexyl) phthalate (159) | Anti-Parkinson’s disease | MPP+--induced SH-SY5Y cells | 80.21 µM (EC50) | Levodopa 2.06 µM (EC50) | [24] |