Research Advances of Bioactive Sesquiterpenoids Isolated from Marine-Derived Aspergillus sp.
Abstract
:1. Introduction
2. Characteristics of Sesquiterpenoids from Marine Aspergillus sp.
3. Bioactivity of Sesquiterpenoids from Aspergillus sp.
3.1. Antibacterial Activity
3.2. Antitumor Activity
3.3. Anti-Inflammatory Activity
3.4. Enzymatic Inhibitory Activity
3.5. Other Activities
4. Chemical Synthesis and Biosynthesis of Sesquiterpenoids from Marine Aspergillus sp.
4.1. Chemically Induced Synthesis
4.2. Biosynthetic Pathways
5. Potency of Sesquiterpenoids from Marine Aspergillus sp.
6. Conclusions and Perspective
Author Contributions
Funding
Conflicts of Interest
References
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Compound Name/Chemical Class | Marine Source | Type of Strains | Activity (MIC) | Reference |
---|---|---|---|---|
Compounds 1,3 and 5 | Marine-sponge-derived fungus Aspergillus | not reported | not reported | [14] 2012 |
Compound 2 | S. albus, M. tetragenus | 1.25–5 µM | ||
Compound 4 | S. albus, B. subtilis | 2.5–5 µM | ||
Compound 6 | Marine-sponge-derived fungus Aspergillus sydowii ZSDS1-F6 | A. hydrophila and K. pneumonia | 4.3 and 21.4 µM | [15] 2014 |
Compound 7 | K. pneumonia | 10.7 µM | ||
Compound 8 | E. faecalis | 18.8 µM | ||
Flavilane A(9) | Fresh-seawater-derived fungus Aspergillus flavipes 297 | Pathogenic bacteria | 2–64 µM | [16] 2021 |
Compound 10 | Pathogenic bacteria and Pathogenic fungus V. mari | |||
Compounds 11,12 | Deep sea sediment fungus Aspergillus versicolor SD-330 | A. hydrophilia, E. coli, E. tarda, and V. harveyi | 2–8 µM | [17] 2021 |
Compound 13 | E. coli | 1 µM | ||
Compound 14 | Seawater-derived fungus Aspergillus sydowii SW9 | E. coli and S. pneumonise | 2–4 µM | [18] 2019 |
Compounds 15,16 | Deep sea sediment fungus Aspergillus versicolor SD-330 | E. coli, E. trada, V. harveyi, and V. parahaemolyticus | 8 µM | [19] 2019 |
Compound 17 | E. coli, Aeromonas hydrophilia, E. tarda, V. anguillarum, and V. harveyi | 1–4 µM | ||
Compound 18 | not reported | not reported | ||
Compounds 19–21 | Marine-gorgonian-derived fungus Aspergillus | S. aureus | Inhibition zones were 5–11 mm at 100µg/mL | [20] 2010 |
Compounds 22–28 | Mangrove endophytic fungus Aspergillus xy02 | S. aureus | 31.5–41.9 µM | [21] 2018 |
Asperchondols A, B(29, 30) | Marine-sponge-derived fungus Aspergillus | S. aureus | 25–50 µM | [22] 2016 |
Albican-11,14-diol (31) | Marine-alga-derived fungus Aspergillus versicolor | E. coli and S. aureus | Inhibition zones were 7–10.3 mm at 30 μg/disk | [23] 2012 |
Compounds 32–35 | Marine-alga-derived fungus Aspergillus RR-YLW-12 | V. harveyi, V. splendidus, V. parahaemolytics, and V. anguillarum | not reported | [24] 2021 |
Compounds 36–38 | Marine-coral-derived fungus Aspergillus versicolor ZJ-2008015 | S. aureus and S. albus | 2.6–6.4 µM | [25] 2012 |
Compounds 39,40 | Marine-sponge-derived fungus Aspergillus insuetus OY-207 | N. crassa | 140–242 µM | [26] 2011 |
Compound Name/Chemical Class | Marine Source | Cell lines | Activity (IC50/EC50/ED50/inhibition rate) | Reference |
Asperorlactone (41) | Marine sediment fungus Aspergillus oryzae | A549, HepG2, and MCF-7 | <100 µM | [27] 2021 |
Echinolactone D (42) | not reported | |||
Asperienes A-D (43–46) | Marine fungus Aspergillus flavus CF13–11 | A549, HeLa, MGC-803, and MCF-7 | 1.4–8.3 µM | [28] 2019 |
Compounds 47,48 | Marine sediment fungus Aspergillus flocculosus | Neuro-2a and 22Rv1 | 3–31.5 µM | [29] 2019 |
Compounds 49,50 | Marine fungus Aspergillus ochraceus Jcma1F17 | H1975, U937, K562, BGC-823, MOLT-4, MCF-7 A549, HeLa, HL60, and Huh-7 | 1.95–6.35 µM | [30] 2014 |
Insulicolide A (51) | Marine-sponge-derived fungus Aspergillus insulicola MD10-2 | H-460 | 6.9 µM | [31] 2016 |
Compounds 52, 53 | Marine fungus Aspergillus ochraceus Jcma1F17 | 786-O, ACHN, and OS-RC-2 | 2.3–11 µM | [32] 2018 |
Compound 54 | 0.89–1.5 µM | |||
Compounds 57, 58 | Marine-sponge-derived fungus Aspergillus insulicola | AsPC-1 and PANC-1 | 2.3–4.6 µM | [33] 2022 |
Compounds 59, 61 | Marine-sponge-derived fungus Aspergillus ustus | L5178Y | 0.6–5.3 µM | [34] 2009 |
Compound 60 | L5178Y, PC12, and HeLa | 0.6–7.2 µM | ||
Compound 62 | Mangrove endophytic fungus Aspergillus ustus | P388 | 8.7 µM | [35] 2011 |
Compounds 63, 65 | Marine-sponge-derived fungus Aspergillus | HePG-2 and Caski | 2.91–12.4 µM | [36] 2012 |
Compound 64 | not reported | |||
β-D-glucopyranosylaspergillusene A (66) | Marine-sponge-derived fungus Aspergillus sydowii J05B7F-4 | HePG-2, HCT116, and KB | 50–70 µM | [37] 2017 |
Compound 67 | Mangrove endophytic fungus Aspergillus terreus GX3-3B | MCF-7, HL-60 | 3.43–4.49 µM | [38] 2013 |
Compound 68 | MCF-7 | 2.79 µM | ||
Compound 70 | HL-60 | 0.6 µM | ||
Aspergiketone (71) | Coastal saline soil fungus Aspergillus fumigatus | HL-60 and A549 | 12.4–22.1 µM | [39] 2016 |
Oxalicine B (72) | Sea-urchin-derived fungus Aspergillus fumigatus | P388 | 55.9 µM | [40] 2012 |
Compound 73 | Marine fungus Aspergillus ustus 094102 | HL-60 and A549 | 20.6–30 µM | [41] 2009 |
Compounds 74, 75 | 9–10.5 µM | |||
Compound 76 | Marine-sponge-derived fungus Aspergillus ustus | L5178Y | 1.9 µM | [42] 2008 |
Compound 77 | Marine sediment fungus Aspergillus fumigatus YK-7 | U937 | 84.9 µM | [43] 2015 |
Asperflavinoid A (78) | Marine fungus Aspergillus flavipes 297 | HepG2 and MKN-45 | 26.8–38.5 µM | [44] 2021 |
Compound Name/Chemical Class | Marine Source | Target Enzyme | Activity (IC50/inhibitory rate) | Reference |
7-Deoxy-7,14-didehydrosydonol (79) | Mangrove endophytic fungus Aspergillus versicolor SYSU-SKS025 | inhibit NO production in RAW 264.7 macrophages | 12.5 µM | [45] 2018 |
Compounds 80–82 | Marine-algal-derived fungus Aspergillus ZL0-1B14 | inhibit LPS-stimulated RAW264.7 macrophages | not reported | [46] 2015 |
Compound 83 | inhibit LPS-stimulated RAW264.7 macrophages and exhibited an inhibitory effect against IL-6 production | 69% at 40 µM | ||
Compound 84,85 | Marine fungus Aspergillus terreus | inhibitory activity of NO production | 37.3% and 47.7% at 40 μM | [47] 2018 |
Compound 86,87,89 | Marine sediment fungus Aspergillus sydowii | not reported | not reported | [48] 2013 |
Compounds 88,90 | inhibition against fMLP/CB-induced superoxide anion generation by human neutrophils and inhibitory activity against the release of elastase induced by fMLP/CB | 5.23–16.39 µM | ||
Compound 91–94 | Marine sediment fungus Aspergillus SCSIOW2 | inhibitory activity of NO production | not reported | [49] 2016 |
Compounds 95–99 | Mangrove endophytic fungus Aspergillus GXNU-MA1 | inhibitory activity of NO production | 16.15–27.08 µM | [50] 2022 |
Compounds 100,102–107 | Marine sediment fungus Aspergillus sydowii MCCC3A00324 | against NO secretion in LPS-activited BV-2 microglia cells | 32.6%-45.4% at 10 µM | [51] 2020 |
Compound 101 | against NO secretion in LPS-activited BV-2 microglia cells and anti-inflammatory effect | 45% at 10 µM | ||
inhibiting NF-κB activation pathway | not reported | |||
Compound 108 | Marine fungus Aspergillus ochraceus | suppressed the RANKL-induced osteoclats formation and bone resorption by targeting NF-κB | not reported | [52] 2020 |
Compound Name/Chemical Class | Marine Source | Target Enzyme | Activity/(IC50) | Reference |
7-Deoxy-7,14-didehydrosydonol (79) | Mangrove endophytic fungus Aspergillus versicolor SYSU-SKS025 | inhibitory effect on α-glucosidase | 7.5 µM | [45] 2018 |
Compounds 109–112 | Mangrove endophytic fungus Aspergillus flavus QQSG-3 | inhibitory effect on α-glucosidase | 1.5–4.5 µM | [53] 2018 |
Compound 113 | Marine-coral-derived fungus Aspergillus EGF15-0-3 | inhibit ChE | not reported | [54] 2020 |
2-deoxy-2β-hydroxysubergorgic (114) | ||||
Compounds 115–118 | Marine-ascidian-derived fungus Aspergillus ustus TK-5 | inhibitory activity against neuraminidase | 28.4–37.3 µM | [55] 2018 |
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Sun, L.; Wang, H.; Yan, M.; Sai, C.; Zhang, Z. Research Advances of Bioactive Sesquiterpenoids Isolated from Marine-Derived Aspergillus sp. Molecules 2022, 27, 7376. https://doi.org/10.3390/molecules27217376
Sun L, Wang H, Yan M, Sai C, Zhang Z. Research Advances of Bioactive Sesquiterpenoids Isolated from Marine-Derived Aspergillus sp. Molecules. 2022; 27(21):7376. https://doi.org/10.3390/molecules27217376
Chicago/Turabian StyleSun, Lixiang, Huannan Wang, Maocai Yan, Chunmei Sai, and Zhen Zhang. 2022. "Research Advances of Bioactive Sesquiterpenoids Isolated from Marine-Derived Aspergillus sp." Molecules 27, no. 21: 7376. https://doi.org/10.3390/molecules27217376