11-o-galloylbergenin and bergenin

The rhizomes of Astilbe rivularis, commonly known as 'Thulo Okhati' are widely used in Nepal as tonic for uterine and menstrual disorders. In our preliminary study, the 70% MeOH extract of the rhizomes showed potent antioxidant activity. Hence, present study was aimed for the isolation of potent antioxidant constituents. Bergenin (1), 11-O-galloylbergenin (2), (+)-catechin (3), (-)-catechin (4), (-)-afzelechin (5), (-)-epiafzelechin (6) and 2-(β-D-glucopyranosyloxy)-4-hydroxylbenzenacetonitrile (7) were isolated from the rhizomes. Structures of these compounds were elucidated on the basis of spectroscopic methods. All these isolated compounds were evaluated for their in vitro antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. 11-O-Galloylbergenin (2), (+)-catechin (3), (-)-catechin (4), (-)-afzelechin (5) and (-)-epiafzelechin (6) showed potent antioxidant activity.

Topics: Antioxidants; Benzopyrans; Biphenyl Compounds; Catechin; Drug Evaluation, Preclinical; Flavonoids; Gallic Acid; Magnetic Resonance Spectroscopy; Molecular Structure; Nepal; Phenols; Picrates; Plant Extracts; Rhizome; Saxifragaceae

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. The demonstrated biological potentials declared that compound 2 could be the better natural antioxidant and antiplasmodial candidate.

Topics: Antimalarials; Antioxidants; Benzopyrans; Gallic Acid; Magnetic Resonance Spectroscopy; Mallotus Plant; Molecular Docking Simulation; Parasitic Sensitivity Tests; Plant Extracts; Plasmodium falciparum

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.

Topics: Antioxidants; Benzopyrans; Gallic Acid; Inhibitory Concentration 50; Plant Components, Aerial; Plant Extracts; Saxifragaceae; Structure-Activity Relationship; Urease

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).

Topics: Antimalarials; Antioxidants; Benzopyrans; Gallic Acid; Plant Extracts; Plant Roots; Saxifragaceae

Bergenin (1), major bioactive compound isolated from methanolic extract of Mallotus philippinensis, displayed moderate AGE inhibition activity (IC(50)=186.73 μM). A series of derivatives of bergenin (3a-k) containing variety of aromatic acids were synthesized under mild conditions by modification of sugar part. Selective esterification of hydroxyl groups on the sugar part enhanced antiglycation potential of bergenin. Compounds 3j and 3k exhibited potent antiglycation activity with the IC(50) values of 60.75 and 12.28 μM, respectively.

Topics: Benzopyrans; Dose-Response Relationship, Drug; Glycation End Products, Advanced; Mallotus Plant; Molecular Structure; Stereoisomerism; Structure-Activity Relationship

To study the chemical constituents of Yao Medicine Cissus pteroclada.. The compounds were isolated and purified by column chromatography with silica gel, TLC and recrystallization. Their structures were elucidated on the basis of physicochemical properties and spectra analysis.. Six compounds were isolated and identified as beta-sitosterol (I), bergenin (II), 11-O-galloylbergenin (III), 11-O-(4-hydroxy benzoyl) bergenin (IV), gallic acid (V), daucosterol (VI).. Compounds III and NIV are obtained from the genus for the first time. All the compounds are isolated from this plant for the first time except the compound II.

Topics: Benzopyrans; Cissus; Gallic Acid; Molecular Structure; Plant Stems; Plants, Medicinal; Sitosterols; Spectrophotometry, Infrared; Spectrophotometry, Ultraviolet