Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Experimental Procedures
2.2. Production and Purification of Fungal Metabolites
2.3. X-ray Experimental
2.4. Bioassays
2.4.1. Phytotoxic Activity
2.4.2. Antimicrobial Activity
2.4.3. Cytotoxic Activity
2.4.4. Insecticidal Activity
2.4.5. Zootoxicity Assay
2.4.6. Esterase Inhibitory Activity
3. Results
3.1. Structure Elucidation
3.2. Biological Activity
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Position (in 1 and 5) | Literature Assignment (5a) [24] | 1 | 5 | ||
---|---|---|---|---|---|
δH (J in Hz) | δC | δH (J in Hz) | δC | ||
1 | 1 | 124.0 | - | 148.8 | |
2 | 5 | 7.25 1H, s | 124.4 | - | 155.7 |
3 | 8 | 144.7 | 7.40 1H, d (9.0) | 125.4 | |
4 | 9 | 131.1 | 7.45 1H, d (9.0) | 121.7 | |
4a | 6a | 151.9 | - | 150.5 | |
4b | 4 | 155.7 | - | 161.2 | |
5 | 6 | 6.88 1H, d (8.0) | 111.5 | 6.64 1H, s | 111.3 |
6 | 10 | 7.66 1H, t (8.0) | 137.3 | - | 151.9 |
7 | 3 | 7.06 1H, d (8.0) | 107.2 | 6.75 1H, s | 107.2 |
8 | 10a | 161.7 | - | 155.7 | |
8a | 2 | 108.5 | - | 114.7 | |
9 | MeCO | 180.5 | - | 180.3 | |
9a | 10b | 116.7 | - | 118.5 | |
10 | 7 | 169.0 | - | 168.9 | |
11 | OMe | 4.04 3H, s | 53.2 | 4.03 3H, s | 53.1 |
12 | MeCO | 2.46 3H, s | 20.9 | 2.45 3H, s | 22.6 |
8-OH | 12.10 s | 12.23 s |
Position (in 2 and 9) | Literature Assignment (9a) [24] | 2 | 9 | ||
---|---|---|---|---|---|
δH (J in Hz) | δC | δH (J in Hz) | δC | ||
1 | 10a | 132.3 | 130.3 | ||
2 | 8 | 127.5 | 128.8 | ||
3 | 9 | 7.56 1H, d (8.5) | 122.7 | 7.48 1H, d (7.5) | 122.1 |
4 | 10 | 7.43 1H, d (8.5) | 128.9 | 7.36 1H, t (7.5) | 130.9 |
5 | 2 | 125.2 | 7.15 1H, d (7.5) | 121.4 | |
6 | 6a | 147.8 | 153.6 | ||
7 | COMe | 197.0 | 199.0 | ||
8 | 10b | 109.1 | 107.5 | ||
9 | 5 | 160.5 | 160.2 | ||
10 | 3 | 6.23 2H, s | 109.3 | 6.24 2H, s | 109.4 |
11 | 1 | 148.9 | 148.8 | ||
12 | 6 | 6.23 2H, s | 109.3 | 6.24 2H, s | 109.4 |
13 | 4 | 160.5 | 160.2 | ||
14 | 7 | 166.0 | 167.3 | ||
15 | OMe | 3.76 3H, s | 52.6 | 3.65 3H, s | 52.5 |
16 | COMe | 2.26 3H, s | 22.1 | 2.25 3H, s | 22.1 |
Compound | Phytotoxic | Antimicrobial 3 | Insecticidal 4 | |||
---|---|---|---|---|---|---|
Sonchus arvensis1 | Elytrigia repens2 | Bacillus subtilis | Escherichia coli | Candida tropicalis | Wheat Aphid | |
1 | 0 | 0 | NA | NA | NA | 43.8 ± 12.1 |
2 | 2.4 ± 0.2 | 1.1 ± 0.3 | 10 | NA | 50 | nt |
3 | 1.5 ± 0.3 | 1.0 ± 0 | NA | NA | NA | 58.8 ± 17.8 |
4 | 0 | 0 | <5 | 100 | <5 | 80.0 ± 8.5 |
5 | 0 | 0.5 ± 0 | NA | NA | NA | 60.0 ± 4.8 |
6 | 0 | 0 | NA | NA | NA | 41.3 ± 8.7 |
7 | 0 | 0 | NA | NA | NA | 11.3 ± 6.5 |
8 | 0.9 ± 0.2 | 0 | <0.5 | <0.5 | 1 | nt |
9 | 1.7 ± 0.2 | 1.2 ± 0.4 | 20 | 20 | 100 | 42.5 ± 23.6 |
10 | 1.6 ± 0.5 | 2.0 ± 0.4 | 100 | NA | NA | 73.8 ± 9.1 |
11 | 0.7 ± 0.2 | 2.0 ± 0 | 50 | NA | NA | NA |
12 | 0.6 ± 0.2 | 1.7 ± 0.3 | 100 | NA | NA | 41.3 ± 12.6 |
13 | 0 | 0 | 50 | NA | 20 | 14.5 ± 9.4 |
Compound | Anti-CE Activity, % 1 | Anti-BCE Activity, % 1 | CE/BCE Activity |
---|---|---|---|
1 | 61.3 | 89.3 | 0.69 |
2 | 14.1 | 83.8 | 0.17 |
3 | 28.7 | 80.6 | 0.36 |
4 | 65.7 | 91.5 | 0.72 |
6 | 2.9 | 62.6 | 0.05 |
7 | 55.4 | 80.6 | 0.69 |
9 | 68.6 | 55.1 | 1.24 |
13 | 91.3 | 96.7 | 0.94 |
Compound | IC50, µM | |
---|---|---|
U937 | K562 | |
1 | NA | NA |
2 | >100 | >100 |
3 | >100 | >100 |
4 | 72 | >100 |
5 | NA | >100 |
6 | 90 | >100 |
7 | NA | NA |
8 | nt | nt |
9 | NA | NA |
10 | >100 | NA |
11 | NA | NA |
12 | >100 | >100 |
13 | >100 | >100 |
Etoposide | 0.85 | 83 |
Compound | Yield from Solid Culture of A. sonchi, mg/kg | Known Producers/Yield | Biological Activity |
---|---|---|---|
methyl 8-dihydroxy-3-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (1) | 6 | – * | Weak insecticidal * |
5-chloromoniliphenone (2) | 7 | – * | Phytotoxic *, cytotoxic *, antiesterase * |
4-chloropinselin (3) | 1879 | Monilinia fructicola [40]/15 mg/L; Bipolaris sorokiniana [42]/2 mg/kg; | Insecticidal * |
methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) | 29 | B. sorokiniana [42]/1 mg/kg; | Antimicrobial [42], insecticidal *, cytotoxic * |
pinselin (5) | 223 | Penicillium amarum [71]/ND *; Aspergillus sydowii [58]/4.4 mg/kg; Phomopsis sp. [59]/<1 mg/L; Xylaria sp. [72]/ND; P. citrinum [60]/<1 mg/L; Engyodontium album [73]/3.3 mg/kg; Scopulariopsis sp. [74]/1.8 mg/kg; Cassia occidentalis [75]/ND; | Immunosuppressive [58], cytotoxic [59], insecticidal * |
methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (6) | 56 | Microsphaeropsis sp. [47]/<1 mg/L; Scopulariopsis sp. [74]/2.5 mg/kg; Aspergillus iizukae [76]/<1 mg/L; | antiviral [76];antiesterase * |
methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (7) | 46 | M. fructicola [40]/ND; A. sydowii [58]/2.3 mg/kg; P. citrinum [60]/<1 mg/L; | immunosuppressive [58] |
chloromonilicin (8) | 11 | M. fructicola [40]/74 mg/L; A. sonchi [27]/ND; Cochliobolus australiensis [45]/2.23 mg/L; | antimicrobial [40], antifungal [27] |
moniliphenone (9) | 154 | M. fructicola [40]/87.4 mg/L; Hypocreales MSX 17022 [61]/112 mg/kg; A. sydowii [58]/6.3 mg/kg; P. citrinum [60]/<1 mg/L; Leptosphaeria sp. [77]/26 mg/kg; | cytotoxic [61] |
chloromonilinic acid B (10) | 10 | M. fructicola [44]/8 mg/L; B. sorokiniana [42]/<1 mg/L; C. australiensis [45]/16.8 mg/L; | phytotoxic [45], insecticidal * |
chloromonilinic acid C (12) | 7 | C. australiensis [45]/3.0 mg/L; | phytotoxic [45], cytotoxic * |
chloromonilinic acid D (11) | 3 | C. australiensis [45]/6.2 mg/L; | phytotoxic [45] |
α- and β-diversolonic esters (13) | 12 | P. diversum [46]/2.4 mg/L; P. citrinum [60]/<1 mg/L | cytotoxic [61] |
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Dalinova, A.; Chisty, L.; Kochura, D.; Garnyuk, V.; Petrova, M.; Prokofieva, D.; Yurchenko, A.; Dubovik, V.; Ivanov, A.; Smirnov, S.; et al. Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi. Biomolecules 2020, 10, 81. https://doi.org/10.3390/biom10010081
Dalinova A, Chisty L, Kochura D, Garnyuk V, Petrova M, Prokofieva D, Yurchenko A, Dubovik V, Ivanov A, Smirnov S, et al. Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi. Biomolecules. 2020; 10(1):81. https://doi.org/10.3390/biom10010081
Chicago/Turabian StyleDalinova, Anna, Leonid Chisty, Dmitry Kochura, Varvara Garnyuk, Maria Petrova, Darya Prokofieva, Anton Yurchenko, Vsevolod Dubovik, Alexander Ivanov, Sergey Smirnov, and et al. 2020. "Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi" Biomolecules 10, no. 1: 81. https://doi.org/10.3390/biom10010081