Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity
Abstract In this work, the rapid and efficient preparation of isolated galloyl glucoside tautomer free radical inhibitors was investigated using Saxifraga tangutica as a raw material. Four highly polar galloyl glucoside tautomers, 3-O-galloyl-α-d-glucose ⇌ 3-O-galloyl-β-d-glucose (Fr2-1-1), 2-O-gall...
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2024-11-01
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| Online Access: | https://doi.org/10.1186/s13065-024-01330-z |
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| author | Yingying Tong Ming Chu Jia Zhou Qilan Wang Gang Li A. M. Abd El-Aty Jun Dang |
| author_facet | Yingying Tong Ming Chu Jia Zhou Qilan Wang Gang Li A. M. Abd El-Aty Jun Dang |
| author_sort | Yingying Tong |
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| description | Abstract In this work, the rapid and efficient preparation of isolated galloyl glucoside tautomer free radical inhibitors was investigated using Saxifraga tangutica as a raw material. Four highly polar galloyl glucoside tautomers, 3-O-galloyl-α-d-glucose ⇌ 3-O-galloyl-β-d-glucose (Fr2-1-1), 2-O-galloyl-α-d-glucose ⇌ 2-O-galloyl-β-d-glucose (Fr2-1-2/2-1-3), 1-O-galloyl-β-d-glucose (Fr2-2-1), and 6-O-galloyl-α-d-glucose ⇌ 6-O-galloyl-β-d-glucose (Fr2-3-1/Fr2-3-2), were obtained via two-step medium-pressure liquid chromatography (with solid loading instead of conventional liquid injection) and one-step high-performance chromatography coupled with on-line RPLC-DPPH techniques for targeted isolation. This separation integration technique not only increases sample intake and reduces time cost but also visualizes each step of targeted separation. All four compounds were isolated from the plant for the first time. In vitro antioxidant activity assays by DPPH (1,1‑diphenyl-2-picrylhydrazyl) revealed that Fr2-1-2/Fr2-1-3 (IC50: 5.52 ± 0.32 μM), Fr2-2-1 (IC50: 7.22 ± 0.57 μM), and Fr2-3–1/Fr2-3-2 (IC50: 7.36 ± 0.25 μM) had superior free radical scavenging abilities and that both were superior to that of quercetin (IC50: 18.61 ± 3.55 μM). Oxidative stress assays revealed that Fr2-1-2/Fr2-1-3 significantly inhibited oxidative stress damage in H2O2-induced HepG2 cells, decreased the level of ROS (P < 0.01) and protected hepatocytes. Combined with the current results, gallic acid showed greater antioxidant activity when H atoms were replaced at d-glucose –OH (C-2) than at the other three sites [–OH (C-1), –OH (C-6) and –OH (C-3)]. |
| format | Article |
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| institution | DOAJ |
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| publishDate | 2024-11-01 |
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| spelling | doaj-art-402d24a51d5d4678a6e2c268c8a423872025-08-20T02:49:59ZengBMCBMC Chemistry2661-801X2024-11-0118111210.1186/s13065-024-01330-zIsolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activityYingying Tong0Ming Chu1Jia Zhou2Qilan Wang3Gang Li4A. M. Abd El-Aty5Jun Dang6Qinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of SciencesCenter for Mitochondria and Healthy Aging, College of Life Sciences, Yantai UniversityQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of SciencesQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of SciencesCenter for Mitochondria and Healthy Aging, College of Life Sciences, Yantai UniversityDepartment of Pharmacology, Faculty of Veterinary Medicine, Cairo UniversityQinghai Provincial Key Laboratory of Tibetan Medicine Research, Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of SciencesAbstract In this work, the rapid and efficient preparation of isolated galloyl glucoside tautomer free radical inhibitors was investigated using Saxifraga tangutica as a raw material. Four highly polar galloyl glucoside tautomers, 3-O-galloyl-α-d-glucose ⇌ 3-O-galloyl-β-d-glucose (Fr2-1-1), 2-O-galloyl-α-d-glucose ⇌ 2-O-galloyl-β-d-glucose (Fr2-1-2/2-1-3), 1-O-galloyl-β-d-glucose (Fr2-2-1), and 6-O-galloyl-α-d-glucose ⇌ 6-O-galloyl-β-d-glucose (Fr2-3-1/Fr2-3-2), were obtained via two-step medium-pressure liquid chromatography (with solid loading instead of conventional liquid injection) and one-step high-performance chromatography coupled with on-line RPLC-DPPH techniques for targeted isolation. This separation integration technique not only increases sample intake and reduces time cost but also visualizes each step of targeted separation. All four compounds were isolated from the plant for the first time. In vitro antioxidant activity assays by DPPH (1,1‑diphenyl-2-picrylhydrazyl) revealed that Fr2-1-2/Fr2-1-3 (IC50: 5.52 ± 0.32 μM), Fr2-2-1 (IC50: 7.22 ± 0.57 μM), and Fr2-3–1/Fr2-3-2 (IC50: 7.36 ± 0.25 μM) had superior free radical scavenging abilities and that both were superior to that of quercetin (IC50: 18.61 ± 3.55 μM). Oxidative stress assays revealed that Fr2-1-2/Fr2-1-3 significantly inhibited oxidative stress damage in H2O2-induced HepG2 cells, decreased the level of ROS (P < 0.01) and protected hepatocytes. Combined with the current results, gallic acid showed greater antioxidant activity when H atoms were replaced at d-glucose –OH (C-2) than at the other three sites [–OH (C-1), –OH (C-6) and –OH (C-3)].https://doi.org/10.1186/s13065-024-01330-zSaxifraga tanguticaIsolationGalloyl glucoside tautomersAntioxidative activityHepG2 cellsStructure‒activity relationships |
| spellingShingle | Yingying Tong Ming Chu Jia Zhou Qilan Wang Gang Li A. M. Abd El-Aty Jun Dang Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity BMC Chemistry Saxifraga tangutica Isolation Galloyl glucoside tautomers Antioxidative activity HepG2 cells Structure‒activity relationships |
| title | Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| title_full | Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| title_fullStr | Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| title_full_unstemmed | Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| title_short | Isolation of highly polar galloyl glucoside tautomers from Saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| title_sort | isolation of highly polar galloyl glucoside tautomers from saxifraga tangutica through preparative chromatography and assessment of their in vitro antioxidant activity |
| topic | Saxifraga tangutica Isolation Galloyl glucoside tautomers Antioxidative activity HepG2 cells Structure‒activity relationships |
| url | https://doi.org/10.1186/s13065-024-01330-z |
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