Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isolation of Compounds 1–6
2.2. Structural Elucidation of the Isolated Compounds 1–6
2.3. Evaluation of the Antioxidant Activity of Compounds 1–6
3. Materials and Methods
3.1. General Experimental Procedure and Plant Material
3.2. Extraction and Separation/Isolation of the Compounds
3.2.1. Ginkgopanoside (1)
3.2.2. (E)-Coniferin (2)
3.2.3. Syringin (3)
3.2.4. (E)-Ferulic Acid 4-O-β-D-Glucoside (4)
3.2.5. (E)-Sinapic Acid 4-O-β-D-Glucopyranoside (5)
3.2.6. (Z)-4-Coumaric Acid 4-O-β-d-Glucopyranoside (6)
3.3. Acid Hydrolysis and Absolute Configuration Determination of the Sugar Moieties of Compound 1
3.4. Absolute Configuration of the 1,2-Diol Functionalities in Compound 1
3.5. DPPH Radical-Scavenging Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Position | 1 | |
---|---|---|
δH (J in Hz) | δC | |
1 | 3.51, m; 3.62, dd (11.5, 4.0) | 64.8, CH2 |
2 | 3.94, m | 72.7, CH |
3 | 2.66, dd (14.0, 8.5); 2.84, dd (14.0, 5.0) | 38.3, CH2 |
1′ | 134.1, C | |
2′ | 7.01, d (1.5) | 113.8, CH |
3′ | 148.6, C | |
4′ | 143.8, C | |
5′ | 7.12, d (8.0) | 116.1, CH |
6′ | 6.88, dd (8.0, 1.5) | 122.1, CH |
3′-OCH3 | 3.87, s | 55.6, CH3 |
1′′ | 5.09, d (7.5) | 100.6, CH |
2′′ | 3.60, m | 72.8, CH |
3′′ | 3.51, m | 69.2, CH |
4′′ | 3.57, m | 76.2, CH |
5′′ | 3.58, m | 75.7, CH |
6′′ | 3.75, dd (12.5, 5.5); 3.90, dd (12.5, 2.0) | 60.3, CH2 |
Compound | IC50 (μM) a | Compound | IC50 (μM) a |
---|---|---|---|
1 | 32.75 ± 2.32 | 4 | 37.85 ± 5.10 |
1a | 5.23 ± 0.78 | 5 | 45.83 ± 1.90 |
2 | 36.51 ± 1.42 | 6 | >50 |
3 | 48.20 ± 3.08 | Ascorbic acid b | 2.54 ± 0.21 |
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Alishir, A.; Kim, K.H. Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside. Plants 2021, 10, 2702. https://doi.org/10.3390/plants10122702
Alishir A, Kim KH. Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside. Plants. 2021; 10(12):2702. https://doi.org/10.3390/plants10122702
Chicago/Turabian StyleAlishir, Akida, and Ki Hyun Kim. 2021. "Antioxidant Phenylpropanoid Glycosides from Ginkgo biloba Fruit and Identification of a New Phenylpropanoid Glycoside, Ginkgopanoside" Plants 10, no. 12: 2702. https://doi.org/10.3390/plants10122702