Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of Compounds 1–7
2.2. The Antioxidant Activities of Compounds 1–7
3. Materials and Methods
3.1. General Experimental Procedure
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Acid Hydrolysis of Compound 4
3.5. Determination of Antioxidant Activity
3.5.1. DPPH Radical Scavenging Assay
3.5.2. ABTS Radical Scavenging Assay
3.6. Statistical Analyses
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
Abbreviations
1H-1H COSY | 1H-1H homonuclear chemical shift correlation spectroscopy |
ABTS | 2,2′-azino-bis (3-ethylbenzthiazoline-6-sulphonic acid) ammonium salt |
ANOVA | one-way analysis of variance |
CD3OD | methanol-d4 |
DPPH | 2,2-diphenyl-1-picrylhydrazyl |
EtOH | ethanol |
HSQC | heteronuclear single quantum coherence spectroscopy |
HMBC | heteronuclear multiple bond coherence spectroscopy |
HR-ESI-MS | high-resolution electrospray ionization mass spectroscopy |
IC50 | half inhibitory concentration |
IR | infrared absorption spectrum |
MeOH | methanol |
NMR | nuclear magnetic resonance |
IR | infrared absorption spectrum |
SD | standard deviation |
TLC | thin-layer chromatography |
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Position | 1 | 2 | 3 | |||
---|---|---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 134.0 | 134.1 | 133.2 | |||
2 | 116.3 | 6.63 d (2.1) | 116.3 | 6.65 br.s | 130.3 | 7.00 d (8.5) |
3 | 146.2 | 146.2 | 116.1 | 6.68 d (8.5) | ||
4 | 144.5 | 144.5 | 156.6 | |||
5 | 116.5 | 6.67 d (8.0) | 116.5 | 6.68 d (8.0) | 116.1 | 6.68 d (8.5) |
6 | 120.6 | 6.50 dd (8.0, 2.1) | 120.6 | 6.53 br.d (8.0) | 130.3 | 7.00 d (8.5) |
7 | 30.0 | 2.72 t (4.0) | 30.8 | 2.76 t (7.5) | 30.4 | 2.79 m |
8 | 46.3 | 2.72 t (4.0) | 42.6 | 2.85 t (7.5) | 42.6 | 2.79 m |
9 | 211.3 | 202.6 | 202.5 | |||
10 | 50.6 | 2.67 dd (15.9, 7.5) 2.43 dd (15.9, 5.2) | 132.8 | 6.16 d (15.7) | 132.8 | 6.11 dq (15.8, 1.6) |
11 | 74.6 | 3.78 dqd (7.5, 6.2, 5.2) | 145.2 | 6.94 dq (14.1, 6.8) | 145.2 | 6.89 dq (15.8, 6.8) |
12 | 19.4 | 1.13 d (6.2) | 18.4 | 1.19 d (7.0) | 18.4 | 1.86 dd (6.8, 1.7) |
-OCO3 | 56.8 | 3.27 s |
Position | 4 | 5 | 6 | 7 | ||||
---|---|---|---|---|---|---|---|---|
δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | δC | δH (J in Hz) | |
1 | 134.1 | 133.3 | 134.5 | 133.8 | ||||
2 | 116.3 | 6.64 d (2.0) | 130.3 | 7.02 d (8.0) | 130.3 | 7.03 d (8.5) | 130.3 | 7.01 d (8.0) |
3 | 146.1 | 116.1 | 6.70 d (8.0) | 116.7 | 6.70 d (8.5) | 116.1 | 6.69 d (8.0) | |
4 | 144.4 | 156.5 | 156.3 | 156.4 | ||||
5 | 116.5 | 6.67 d (8.0) | 116.1 | 6.70 d (8.0) | 116.7 | 6.70 d (8.5) | 116.1 | 6.69 d (8.0) |
6 | 120.5 | 6.52 dd (8.0, 2.0) | 130.3 | 7.02 d (8.0) | 130.3 | 7.03 d (8.5) | 130.3 | 7.01 d (8.0) |
7 | 30.0 | 2.72 m | 29.7 | 2.77 m | 32.0 | 2.62 m | 31.6 | 2.55 m |
8 | 46.2 | 2.80 m | 46.2 | 2.80 m | 40.8 | 1.71 m | 37.0 | 1.95 m 1.84 m |
9 | 211.9 | 211.9 | 70.1 | 3.74 tt (8.5, 4.3) | 73.3 | 5.08 m | ||
10 | 51.6 | 2.53 dd (15.9, 5.4) 2.83 dd (15.9, 7.4) | 51.5 | 2.53 dd (15.9, 5.4) 2.84 dd (15.9, 7.3) | 45.5 | 1.84 m, 1.58 m | 42.5 | 1.97 m 1.68 m |
11 | 72.4 | 4.34 m | 72.3 | 4.34 m | 74.3 | 4.10 m | 72.7 | 3.97 dq (7.8, 6.0) |
12 | 20.3 | 1.20 d (6.2) | 20.3 | 1.20 d (6.2 ) | 20.1 | 1.21 d (6.0) | 20.0 | 1.19 d (6.0) |
Glc-1′ | 102.4 | 4.34 d (7.8) | 102.3 | 4.34 d (7.7) | 102.3 | 4.36 d (7.8) | 101.8 | 4.32 d (7.7) |
Glc-2′ | 75.0 | 3.12 m | 75.0 | 3.12 dd (9.2, 7.8) | 75.1 | 3.15 dd (9.1, 7.8) | 75.1 | 3.14 dd (8.8, 7.7) |
Glc-3′ | 77.8 | 3.25 m | 77.8 | 3.25 m | 77.9 | 3.28 m | 77.8 | 3.25 m |
Glc-4′ | 71.7 | 3.26 m | 71.7 | 3.26 m | 71.7 | 3.28 m | 71.7 | 3.30 m |
Glc-5′ | 78.0 | 3.35 m | 78.0 | 3.36 m | 78.0 | 3.37 m | 78.0 | 3.34 m |
Glc-6′ | 62.9 | 3.65 dd (11.9, 5.3) 3.84 dd (11.9, 1.9) | 62.9 | 3.64 dd (11.9, 5.3) 3.84 dd (11.9, 1.9) | 62.9 | 3.67 dd (11.8, 5.5) 3.87 dd (11.8, 1.7) | 62.9 | 3.68 dd (11.8, 5.4) 3.79 dd (11.8, 2.3) |
C=O | 173.0 | |||||||
CH3 | 21.3 | 2.01 s |
Compound | IC50 (μM) | |
---|---|---|
DPPH | ABTS | |
1 | 48.66 ± 0.94 | 13.99 ± 2.53 b |
2 | 53.85 ± 1.17 | 13.11 ± 0.94 b |
3 | >100 | 28.85 ± 0.18 |
4 | 43.95 ± 1.91 | 28.44 ± 3.86 c |
5 | >100 | 33.04 ± 1.43 |
6 | >100 | 38.10 ± 3.94 |
7 | >100 | 27.03 ± 0.55 c |
L-ascorbic acid a | 30.41 ± 1.40 | 23.51 ± 0.44 |
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Huang, J.; Chen, D.; Liu, M.; Yu, Y.; Zhang, Y.; Huang, J. Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata. Molecules 2023, 28, 3928. https://doi.org/10.3390/molecules28093928
Huang J, Chen D, Liu M, Yu Y, Zhang Y, Huang J. Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata. Molecules. 2023; 28(9):3928. https://doi.org/10.3390/molecules28093928
Chicago/Turabian StyleHuang, Jiao, Donglin Chen, Mengying Liu, Yarui Yu, Yi Zhang, and Jing Huang. 2023. "Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata" Molecules 28, no. 9: 3928. https://doi.org/10.3390/molecules28093928