11-O-Galloylbergenin - CAS 82958-44-9
Catalog number: 82958-44-9
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11-O-Galloylbergenin is a natural phenolic found in some plant.
((2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-9-methoxy-6-oxo-2,3,4,4a,6,10b-hexahydropyrano[3,2-c]isochromen-2-yl)methyl 3,4,5-trihydroxybenzoate
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1.Antioxidant and Antiplasmodial Activities of Bergenin and 11-O-Galloylbergenin Isolated from Mallotus philippensis.
Khan H;Amin H;Ullah A;Saba S;Rafique J;Khan K;Ahmad N;Badshah SL Oxid Med Cell Longev. 2016;2016:1051925. doi: 10.1155/2016/1051925. Epub 2016 Feb 22.
Two important biologically active compounds were isolated from Mallotus philippensis. The isolated compounds were characterized using spectroanalytical techniques and found to be bergenin (1) and 11-O-galloylbergenin (2). The in vitro antioxidant and antiplasmodial activities of the isolated compounds were determined. For the antioxidant potential, three standard analytical protocols, namely, DPPH radical scavenging activity (RSA), reducing power assay (RPA), and total antioxidant capacity (TAC) assay, were adopted. The results showed that compound 2 was found to be more potent antioxidant as compared to 1. Fascinatingly, compound 2 displayed better EC50 results as compared to α-tocopherol while being comparable with ascorbic acid. The antiplasmodial assay data showed that both the compound exhibited good activity against chloroquine sensitive strain of Plasmodium falciparum (D10) and IC50 values were found to be less than 8 μM. The in silico molecular docking analyses were also performed for the determination of binding affinity of the isolated compounds using P. falciparum proteins PfLDH and Pfg27. The results showed that compound 2 has high docking score and binding affinity to both protein receptors as compared to compound 1.
2.Comparative antioxidant and antiplasmodial activities of 11-O-galloylbergenin and bergenin isolated from Bergenia ligulata.
Uddin G;Sadat A;Siddiqui BS Trop Biomed. 2014 Mar;31(1):143-8.
In the present study, the antioxidant and antiplasmodial activities of bergenin was compared with its natural derivative 11-O-galloylbergenin for the first time. Both compounds were isolated from Bergenia ligulata. 11-O-galloylbergenin was found to be very active in in-vitro antioxidant assay as compared to bergenin, which was found to be almost inactive. The EC50 values of 11-O-galloylbergenin were 7.45±0.2 μg/mL and 5.39±0.28 μg/mL in DPPH antioxidant assay and reducing power assay respectively, while IC50 value for antiplasmodial assay of both compounds were less than 2.5 μM. Interestingly, in the total antioxidant phosphomolybdate assay, 11-O-galloylbergenin was found more potent (CAHT: 940.04±115.30) as compared to α-tocopherol (CAHT: 552.4±27.91).
3.Structure activity relationship of bergenin, p-hydroxybenzoyl bergenin, 11-O-galloylbergenin as potent antioxidant and urease inhibitor isolated from Bergenia ligulata.
Sadat A;Uddin G;Alam M;Ahmad A;Siddiqui BS Nat Prod Res. 2015;29(24):2291-4. doi: 10.1080/14786419.2015.1004173. Epub 2015 Feb 12.
Ethanol extract of the aerial parts of Bergenia ligulata was subjected to solvent-solvent separation followed by various chromatographic techniques that lead to isolation of bergenine (1), p-hydroxybenzoyl bergenin (2), 11-O-galloylbergenin (3) and methyl gallate (4) as major constituents. Ethyl acetate fraction showed a dose-dependent urease inhibitory pattern with IC50 value of 54μg/mL. Structures of compounds 1 and 3 were established by XRD and 2, 4 by NMR. All these compounds were subjected to DPPH scavenging activity, reducing power assay and urease inhibitory activity. The EC50 7.45 ± 0.2 μg/mL and 5.39 ± 0.28 μg/mL values in terms of antioxidant and reducing power, respectively, were less for 3. Compounds 1-3 showed moderate to significant urease inhibitory potential with IC50 57.1 ± 0.7, IC50 48.4 ± 0.3 and 38.6 ± 1.5. Antioxidant activities and urease inhibitory potential were investigated and compound 3 was found to be the most active.
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