Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites
Abstract
:1. Introduction
2. Results and Discussion
2.1. Biotransformation of Two Isoflavonoids, Licoisoflavanone (1) and Glycyrrhisoflavone (2) with A. niger KCCM 60332
2.2. Biotransformation of Two Chalcones, Echinatin (3) and Isobavachalcone (4) with A. niger KCCM 60332
2.3. Proposed Metabolic Pathways of Isobavachalcone (4) Catalyzed by A. niger KCCM 60332
2.4. Cytotoxicity Evaluation
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation of Substrates 1 and 2
3.4. Synthesis of Substrates 3 and 4
3.5. Microorganisms and Screening for Biostransformation
3.6. Scale-up Fermentation, Extraction, and Isolation of Metabolites 5–21
3.7. Spectroscopic Data of Metabolites 5–21
3.7.1. Spectroscopic Data of the New Compounds 5–7, 10–17, and 19
- Compound 5
- 2.
- Compound 6
- 3.
- Compound 7
- 4.
- Compound 10
- 5.
- Compound 11
- 6.
- Compound 12
- 7.
- Compound 13
- 8.
- Compound 14
- 9.
- Compound 15
- 10.
- Compound 16
- 11.
- Compound 17
- 12.
- Compound 19
3.7.2. 1H-NMR Data of the Compounds 8, 9, 18, 20, and 21
- Compound 8
- 2.
- Compound 9
- 3.
- Compound 18
- 4.
- Compound 20
- 5.
- Compound 21
3.8. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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No. | 5 | 6 | 7 | |||
---|---|---|---|---|---|---|
C/H | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b |
2 | 4.65 t (8.3) | 70.5 | 8.04 s | 153.5 | 8.03 s | 153.6 |
3 | 4.53 dd (10.0, 5.4) 4.23 dd (10.0, 5.4) | 46.9 | 127.2 | 123.3 | ||
4 | 197.9 | 180.9 | 180.8 | |||
5 | 156.0 | 162.4 | 162.4 | |||
6 | 5.99 s | 95.4 | 6.22 d (2.1) | 98.7 | 6.22 d (2.0) | 98.8 |
7 | 157.0 | 164.6 | 164.5 | |||
8 | 125.3 | 6.34 d (2.1) | 93.4 | 6.33 d (2.0) | 93.5 | |
9 | 149.2 | 158.3 | 158.3 | |||
10 | 102.0 | 104.9 | 104.9 | |||
1′ | 115.7 | 123.6 | 122.7 | |||
2′ | 150.7 | 6.81 d (2.1) | 122.3 | 6.75 d (2.1) | 120.8 | |
3′ | 110.9 | 143.9 | 141.2 | |||
4′ | 153.3 | 145.1 | 145.3 | |||
5′ | 6.34 d (8.3) | 108.5 | 122.0 | 120.6 | ||
6′ | 6.91 d (8.3) | 129.3 | 6.92 d (2.1) | 114.2 | 6.86 s | 113.8 |
1″ | 6.69 d (10.0) | 116.6 | 2.97 dd (14.0, 1.9) 2.68 dd (14.0, 10.2) | 32.8 | 3.03 dd (16.7, 5.4) 2.74 dd (16.7, 7.3) | 30.7 |
2″ | 5.68 d (10.0) | 129.1 | 3.65 dd (10.2, 1.9) | 79.2 | 3.79 m | 69.2 |
3″ | 75.1 | 72.5 | 77.4 | |||
4″ | 1.40 s | 26.5 | 1.25 s | 24.3 | 1.39 s | 24.4 |
5″ | 1.40 s | 26.4 | 1.25 s | 23.6 | 1.31 s | 19.6 |
No. | 10 a | 11 a | 12 b | 13 b | ||||
---|---|---|---|---|---|---|---|---|
C/H | δH c (J/Hz) | δC d | δH c (J/Hz) | δC d | δH c (J/Hz) | δC d | δH c (J/Hz) | δC d |
α | 3.17 t (7.6) | 38.9 | 7.71 s | 117.3 | 3.18 t (7.4) | 40.0 | 3.17 t (7.4) | 39.9 |
β | 2.81 t (7.6) | 29.3 | 7.71 s | 143.6 | 2.97 t (7.4) | 29.9 | 2.97 t (7.4) | 29.9 |
C=O | 203.9 | 191.1 | 204.0 | 203.9 | ||||
1 | 131.0 | 125.6 | 133.2 | 133.3 | ||||
2,6 | 7.04 d (8.6) | 129.2 | 7.73 d (8.6) | 131.0 | 7.10 d (8.2) | 129.6 | 7.11 d (8.3) | 129.6 |
3,5 | 6.66 d (8.6) | 115.0 | 6.84 d (8.6) | 115.9 | 6.77 d (8.2) | 115.5 | 6.77 d (8.3) | 115.5 |
4 | 155.5 | 160.5 | 154.2 | 154.1 | ||||
1′ | 111.5 | 112.0 | 112.8 | 112.3 | ||||
2′ | 162.3 | 163.7 | 162.3 | 163.0 | ||||
3′ | 115.2 | 115.4 | 116.8 | 109.3 | ||||
4′ | 13.13 s (OH) | 162.3 | 14.05 s (OH) | 163.7 | 13.10 s (OH) | 162.6 | 13.17 s (OH) | 160.8 |
5′ | 6.41 d (8.9) | 107.8 | 6.47 d (8.9) | 107.9 | 6.41 d (8.9) | 108.7 | 6.32 d (9.0) | 109.3 |
6′ | 7.63 d (8.9) | 129.8 | 7.97 d (8.9) | 129.5 | 7.53 d (8.9) | 129.6 | 7.51 d (9.0) | 128.9 |
1″ | 2.50 (overlay) | 16.6 | 2.53 m | 16.7 | 2.74 t (6.8) | 15.5 | 2.69 t (6.8) | 16.4 |
2″ | 1.52 m | 37.4 | 1.55 m | 37.4 | 1.77 t (6.8) | 41.6 | 1.81 t (6.8) | 32.0 |
3″ | 73.9 | 73.9 | 76.3 | 75.9 | ||||
4″ | 1.12 s | 25.0 | 1.14 s | 25.0 | 1.21 s | 24.7 | 1.34 s | 26.8 |
5″ | 1.12 s | 25.0 | 1.14 s | 25.0 | 1.21 s | 24.7 | 1.34 s | 26.8 |
1′′′ | 3.13 s | 48.4 | 3.15 s | 48.4 | 3.56 q (7.0) | 57.6 | ||
2′′′ | 1.29 t (7.0) | 15.6 |
No. | 14 | 15 | 16 | 17 | 19 | |||||
---|---|---|---|---|---|---|---|---|---|---|
C/H | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b | δH a (J/Hz) | δC b |
α | 3.12 t (7.3) | 44.9 | 3.23 t (7.7) | 39.5 | 3.23 t (7.1) | 39.0 | 7.72 s | 117.5 | 3.17 t (7.7) | 38.9 |
β | 2.75 t (7.3) | 29.5 | 2.82 t (7.7) | 29.2 | 2.82 t (7.1) | 29.1 | 7.72 s | 143.6 | 2.81 t (7.7) | 29.3 |
C=O | 198.6 | 204.6 | 204.6 | 191.1 | 203.8 | |||||
1 | 131.7 | 130.9 | 130.8 | 125.7 | 131.0 | |||||
2,6 | 7.00 d (8.1) | 128.9 | 7.06 d (8.0) | 129.2 | 7.06 d (8.3) | 129.1 | 7.74 d (8.0) | 131.1 | 7.06 d (8.2) | 129.2 |
3,5 | 6.66 d (8.1) | 115.0 | 6.67 d (8.0) | 115.1 | 6.67 d (8.3) | 115.0 | 6.84 d (8.0) | 125.7 | 6.67 d (8.2) | 115.0 |
4 | 155.3 | 155.6 | 155.5 | 160.4 | 155.5 | |||||
1′ | 118.2 | 113.7 | 112.0 | 112.0 | 111.4 | |||||
2′ | 155.2 | 159.4 | 162.1 | 163.8 | 162.3 | |||||
3′ | 108.1 | 113.3 | 107.8 | 115.8 | 115.6 | |||||
4′ | 161.2 | 12.80 s (OH) | 166.8 | 13.18 s (OH) | 159.3 | 14.06 s (OH) | 163.8 | 13.13 s (OH) | 162.3 | |
5′ | 6.40 d (8.6) | 107.0 | 6.41 d (8.7) | 101.7 | 6.34 d (8.9) | 108.5 | 6.43 d (9.0) | 108.0 | 6.40 d (8.8) | 107.9 |
6′ | 7.38 d (8.6) | 129.1 | 7.81 d (8.7) | 132.9 | 7.73 d (8.9) | 129.7 | 7.98 d (9.0) | 129.5 | 7.63 d (8.8) | 129.7 |
1″ | 2.55 t (6.7) | 17.0 | 3.04 d (8.8) | 26.5 | 2.78 dd (17.0, 5.1) 2.46 dd (17.0, 7.0) | 25.2 | 2.57 m | 17.5 | 2.54 m | 17.4 |
2″ | 1.76 t (6.7) | 31.1 | 4.71 t (8.8) | 91.2 | 3.67 t (5.1) | 67.0 | 1.50 m | 42.3 | 1.47 m | 42.3 |
3″ | 74.7 | 70.1 | 78.4 | 69.0 | 69.0 | |||||
4″ | 1.29 s | 26.5 | 1.13 s | 25.8 | 1.27 s | 25.2 | 1.14 s | 29.2 | 1.13 s | 29.1 |
5″ | 1.29 s | 26.5 | 1.12 s | 24.8 | 1.20 s | 20.9 | 1.14 s | 29.2 | 1.13 s | 29.1 |
Compound | IC50 ± SD (μM) | Compound | IC50 ± SD (μM) | ||||
---|---|---|---|---|---|---|---|
A375P | HT-29 | MCF-7 | A375P | HT-29 | MCF-7 | ||
1 | 8.09 ± 0.35 | 7.54 ± 0.70 | 9.20 ± 0.13 | 12 | 4.35 ± 0.35 | 5.77 ± 0.28 | 10.07 ± 1.11 |
2 | 25.48 ± 1.53 | 25.98 ± 0.72 | 26.99 ± 0.77 | 13 | 27.38 ± 0.67 | 60.15 ± 1.15 | 33.87 ± 1.80 |
3 | >100 | >100 | >100 | 14 | 31.90 ± 1.27 | 77.65 ± 1.33 | 47.43 ± 1.91 |
4 | 5.21 ± 0.39 | 21.34 ± 1.40 | 20.94 ± 0.19 | 15 | 66.57 ± 1.91 | >100 | >100 |
5 | >100 | >100 | >100 | 16 | 28.91 ± 1.99 | >100 | 82.77 ± 1.82 |
6 | >100 | >100 | >100 | 17 | 42.98 ± 0.62 | >100 | 43.58 ± 1.39 |
7 | >100 | >100 | >100 | 18 | 70.05 ± 1.27 | >100 | >100 |
8 | 29.41 ± 1.86 | 57.17 ± 4.28 | 59.44 ± 0.39 | 19 | 21.92 ± 2.26 | 70.39 ± 1.53 | 68.26 ± 2.28 |
9 | >100 | >100 | >100 | 20 | 57.60 ± 0.67 | >100 | 85.25 ± 1.51 |
10 | 14.20 ± 0.40 | 73.39 ± 0.48 | 47.23 ± 1.07 | 21 | >100 | >100 | >100 |
11 | 29.38 ± 0.59 | >100 | 61.75 ± 1.57 | DZ | 2.10 ± 0.06 | 10.13 ± 0.27 | 2.33 ± 0.05 |
Substrate | Substrate Amount (mg/Flask) | Number of Flasks | Total Extract Amount (g) |
---|---|---|---|
1 | 3 | 8 | 0.22 |
2 | 3 | 13 | 0.47 |
3 | 3 | 15 | 0.54 |
4 | 3 | 36 | 1.36 |
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Xiao, Y.; Han, F.; Lee, I.-S. Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites. Int. J. Mol. Sci. 2021, 22, 10109. https://doi.org/10.3390/ijms221810109
Xiao Y, Han F, Lee I-S. Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites. International Journal of Molecular Sciences. 2021; 22(18):10109. https://doi.org/10.3390/ijms221810109
Chicago/Turabian StyleXiao, Yina, Fubo Han, and Ik-Soo Lee. 2021. "Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites" International Journal of Molecular Sciences 22, no. 18: 10109. https://doi.org/10.3390/ijms221810109