Structures of New Phenolics Isolated from Licorice, and the Effectiveness of Licorice Phenolics on Vancomycin-Resistant Enterococci
Abstract
:1. Introduction
2. Results and Discussion
2.1. Structures of the New Compounds
Position | 4'-O-Methylglycybenzofuran (8) | Neoglycybenzofuran (14) | ||||||
---|---|---|---|---|---|---|---|---|
δC | HSQC a | δH ( J in Hz) | HMBC b | δC | HSQC a | δH ( J in Hz) | HMBC b | |
C-2 | 145.7 | C | H-10 | 145.5 | C | H-10 | ||
C-3 | 114.2 | C | H-10 | 114.4 | C | H-10 | ||
C-4 | 119.6 | CH | 7.30, d (8.4) | 119.3 | CH | 7.23, d (9.0) | ||
C-5 | 111.5 | CH | 6.77, dd (2.4, 8.4) | H-4 | 111.4 | CH | 6.71, dd (2.4, 9.0) | |
C-6 | 155.8 | C | H-5, 7 | 155.7 | C | H-4, 5, 7 | ||
C-7 | 97.9 | CH | 6.87, d (2.4) | 97.8 | CH | 6.82, d (2.4) | ||
C-8 | 156.2 | C | H-4, 7 | 156.2 | CH | H-4, 7 | ||
C-9 | 123.0 | C | H-5, 7, 10 | 123.8 | CH | H-5, 7, 10 | ||
C-10 | 7.9 | CH3 | 1.89 s | 8.7 | CH3 | 1.97 s | ||
C-1' | 102.1 | C | H-5' | 103.5 | C | H-5' | ||
C-2' | 158.9 | C | H-1" | 159.1 | C | H-1" | ||
C-3' | 114.2 | C | H-5', H-2" | 112.9 | C | H-5', 1", 2" | ||
C-4' | 160.0 | C | H-5', H-1" | 160.0 | C | H-5', 1" | ||
C-5' | 96.6 | CH | 6.41 s | 98.7 | CH | 6.28 s | ||
C-6' | 153.1 | C | H-5' | 155.7 | C | H-5' | ||
C-1" | 22.5 | CH2 | 3.32, d (6.6) | 22.9 | CH2 | 3.13, d (6.6) | ||
C-2" | 124.3 | CH | 5.16, t (6.6) | 124.6 | CH | 5.12, t (6.6) | ||
C-3" | 129.9 | C | H-4", H-5" | 129.7 | C | H-4", 5" | ||
C-4" | 17.2 | CH3 | 1.60 s | 17.8 | CH3 | 1.69 s | ||
C-5" | 25.3 | CH3 | 1.70 s | 25.5 | CH3 | 1.63 s | ||
-OCH3 | 60.7 | CH3 | 3.82 s | H-11 | 60.6 | CH3 | 3.28 s | H-11 |
-OCH3 | 55.0 | CH3 | 3.35 s | H-12 |
2.2. Antibacterial Effects of Licorice Phenolics on VRE
Compounds | Number of -OH Groups | Number of Prenyl Groups | MIC (10−5 M) | ||
---|---|---|---|---|---|
Enterococcus faecium FN-1 | Enterococcus faecalis NCTC12201 | ||||
Isoflavones | |||||
7-O-Methylluteone (3) | 3 | 1 | 8.7 | 8.7 | |
Isoangustone A (6) | 4 | 2 | 3.8 | 3.8 | |
Glycyrrhisofavone (11) | 4 | 1 | 9.0 | 9.0 | |
Glycyrrhiza-isoflavone B (15) | 2 | 0 | 35 | 35 | |
8-(γ,γ-Dimethylallyl)-wighteone (17) | 3 | 2 | 1.9 | 3.8 | |
Glicoricone (22) a | 3 | 1 | >35 | >35 | |
6,8-Diprenylorobol (25) a | 4 | 2 | 30 | 30 | |
Isoflavans | |||||
Licoricidin (2) | 3 | 2 | 1.9 | 1.9 | |
Glyasperin C (13) | 3 | 1 | 4.5 | 4.5 | |
Isoflavanones | |||||
Glyasperin J trimethyl ether (4) | 0 | 1 | 14 | 14 | |
3'-(γ,γ-Dimethylallyl)-kievitone (5) | 4 | 2 | 3.8 | 3.8 | |
Glyasperin J (7) | 3 | 1 | 7.5 | 7.5 | |
3-Arylcoumarins | |||||
Licopyranocoumarin (12) | 2 | 0 | >33 | 33 | |
Glycyrin (20) a | 2 | 1 | 4.2 | 8.4 | |
Glycycoumarin (21) a | 3 | 1 | 4.3 | 4.3 | |
Coumestans | |||||
Glycyrol (18) a | 2 | 1 | 35 | >35 | |
Pterocarpans | |||||
Demethylhomopterocarpan (10) | 1 | 0 | 12 | 12 | |
2-Aryl-3-methylbenzofurans | |||||
Gancaonin I (1) a | 2 | 1 | 4.5 | 4.5 | |
4'-O-Methylglycybenfuran (8) | 2 | 1 | 8.7 | 8.7 | |
Noeglycybenzofuran (14) | 3 | 1 | 4.5 | 4.5 | |
Glycybenzofuran (16) | 3 | 1 | 18 | 18 | |
Benzylphenylketones | |||||
Licoriphenone (9) | 3 | 1 | >34 | 34 | |
Standard antibacterial agents | |||||
Vancomycin a | >6.9 | >6.9 | |||
Linezolid a | 0.74 | 0.74 | |||
EtOAc extract from Tohoku licorice | 16 µg/mL | 32 µg/mL |
2.3. HPLC Analyses of Anti-VRE Phenolics for the Evaluation of EtOAc Extract from G. uralensis as a Source of Antibacterial Agent
Compound | Content (% w/w) a |
---|---|
Glycyrol (18) | 0.54 ± 0.036 |
Gancaonin I (1) | 0.49 ± 0.025 |
Isoangustone A (6) | 0.34 ± 0.031 |
Glycyrin (20) | 0.26 ± 0.015 |
Glycycoumarin (21) | 0.24 ± 0.010 |
Glicoricone (22) | 0.18 ± 0.023 |
6,8-Diprenylorobol (25) | 0.094 ± 0.013 |
Licoriphenone (9) | 0.082 ± 0.017 |
3. Experimental Section
3.1. General Information
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectral Data
3.5. Methylation of Compounds A and B, and Glycybenzofuran
3.6. Antibacterial Assay
3.7. Simultaneous HPLC Analysis of Phenolic Constituents in the EtOAc Extract of Licorice
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Eerdunbayaer; Orabi, M.A.A.; Aoyama, H.; Kuroda, T.; Hatano, T. Structures of New Phenolics Isolated from Licorice, and the Effectiveness of Licorice Phenolics on Vancomycin-Resistant Enterococci. Molecules 2014, 19, 13027-13041. https://doi.org/10.3390/molecules190913027
Eerdunbayaer, Orabi MAA, Aoyama H, Kuroda T, Hatano T. Structures of New Phenolics Isolated from Licorice, and the Effectiveness of Licorice Phenolics on Vancomycin-Resistant Enterococci. Molecules. 2014; 19(9):13027-13041. https://doi.org/10.3390/molecules190913027
Chicago/Turabian StyleEerdunbayaer, Mohamed A. A. Orabi, Hiroe Aoyama, Teruo Kuroda, and Tsutomu Hatano. 2014. "Structures of New Phenolics Isolated from Licorice, and the Effectiveness of Licorice Phenolics on Vancomycin-Resistant Enterococci" Molecules 19, no. 9: 13027-13041. https://doi.org/10.3390/molecules190913027