Identification of Antioxidative Hydrolyzable Tannins in Water Chestnut
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation and Characterization of Phenolic Constituents
2.2. DPPH Radical Scavenging Activity
3. Experimental Section
3.1. General
3.2. Materials
3.3. Extraction and Isolation
3.4. Methylation of Compound 1 Followed by Methanolysis
3.5. Determination of the Sugar Configuration of Compound 1
3.6. DPPH Radical Scavenging Activities of Compounds 1–23
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Position | δH (J in Hz) | δC |
---|---|---|
Glucose I | ||
H-1 | 6.03 (d, J = 8.0) | 94.2 |
H-2 | 5.48 (dd, J = 8.0, 9.5) | 72.4 |
H-3 | 5.63 (t, J = 9.5) | 73.9 |
H-4 | 5.09 (t, J = 9.5) | 71.7 |
H-5 | 4.41 (m) | 73.5 |
H-6 | 5.38 (m), 3.87 (br d, J = 12.5) | 63.9 |
Glucose II | ||
H-1 | 6.04 (d, J = 8.0) | 93.8 |
H-2 | 5.39 (dd, J = 8.0, 9.5) | 72.7 |
H-3 | 5.51 (t, J = 9.5) | 76.7 |
H-4 | 3.65 (t, J = 9.5) | 69.7 |
H-5 | 3.90 (m) | 76.9 |
H-6 | 4.68 (dd, J = 2.0, 12.5), 4.37 (dd, J = 7.0, 12.5) | 65.0 |
Compounds | EC50 (µM) |
---|---|
Trapadin A (1) | 3.14 |
Gallic acid (2) | 10.8 |
Methyl gallate (3) | 21.1 |
Vanillic acid (4) | >100 |
Brevifolincarboxylic acid (5) | 31.5 |
Ellagic acid (6) | 15.7 |
Urolithin A (7) | >100 |
Isourolithin A (8) | >100 |
Urolithin B (9) | >100 |
Urolithin M6 (10) | 23.3 |
1,2-Di-O-galloyl-β-d-glucose (11) | 12.5 |
1,6-Di-O-galloyl-β-d-glucose (12) | 12.3 |
1,2,3-Tri-O-galloyl-β-d-glucose (13) | 7.63 |
1,2,6-Tri-O-galloyl-β-d-glucose (14) | 7.79 |
1,2,3,6-Tetra-O-galloyl-β-d-glucose (15) | 6.55 |
1,2,3,4,6-Penta-O-galloyl-β-d-glucose (16) | 5.06 |
1,6-Di-O-galloyl-2-O-p-coumaroyl-β-d-glucose (17) | 12.0 |
1,6-Di-O-galloyl-2-O-caffeoyl-β-d-glucose (18) | 9.53 |
Tellimagrandin I (19) | 5.75 |
Tellimagrandin II (20) | 5.91 |
Cornusiin A (21) | 3.48 |
Rugosin D (22) | 3.91 |
(7′S,8′R)-Dihydrodehydrodiconiferyl alcohol-9′-O-β-d-glucose (23) | >100 |
Trolox | 26.1 |
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Uchikura, T.; Miura, Y.; Yoshimura, M.; Ito, H.; Amakura, Y. Identification of Antioxidative Hydrolyzable Tannins in Water Chestnut. Molecules 2023, 28, 6563. https://doi.org/10.3390/molecules28186563
Uchikura T, Miura Y, Yoshimura M, Ito H, Amakura Y. Identification of Antioxidative Hydrolyzable Tannins in Water Chestnut. Molecules. 2023; 28(18):6563. https://doi.org/10.3390/molecules28186563
Chicago/Turabian StyleUchikura, Takashi, Yuka Miura, Morio Yoshimura, Hideyuki Ito, and Yoshiaki Amakura. 2023. "Identification of Antioxidative Hydrolyzable Tannins in Water Chestnut" Molecules 28, no. 18: 6563. https://doi.org/10.3390/molecules28186563