Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition

Kashima, Yusei; Yamaki, Hidehiko; Suzuki, Takuya; Miyazawa, Mitsuo

doi:10.3109/14756366.2012.719503

Cited by 7 publications

(2 citation statements)

References 40 publications

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“…Bergenin [31] did not possess α-glucosidase inhibitory activity (2.2 % inhibition at 100 µg/ml), in agreement with a previous report (Kashima et al, 2013). The two phytosteroidal compounds stigmast-4-en-3-one [341] and β-sitosterol [33] exhibited significant inhibitory effects (98.6 % and 40.6 % inhibition, respectively) in comparison with acarbose (21.9 % inhibition).…”

Section: Biological Activity Of Isolated Compoundssupporting

confidence: 84%

Phytochemicals with ?-glucosidase inhibitory activity from cissus javana, dendrobium christyanum, gastrochilus bellinus and huberantha jenkinsii

San

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Phytochemical investigations of Cissus javana DC., Dendrobium christyanum Rchb. f., Gastrochilus bellinus Rchb. f. Kuntze and Huberantha jenkinsii (Hook. f. & Thomson) Chaowasku led to the isolation of twenty-seven compounds, six of which were new naturally occurring compounds. From Cissus javana, three known compounds were isolated, including bergenin, stigmast-4-en-3-one, and ?-sitosterol. From Dendrobium christyanum, thirteen known compounds were identified, namely, n-eicosyl trans-ferulate, n-docosyl 4-hydroxy-trans-cinnamate, 4,5-dihydroxy-2-methoxy-9,10-dihydrophenanthrene, moscatilin, aloifol I, gigantol, batatasin III, dendrosinen B, coniferyl aldehyde, methyl haematommate, atraric acid, vanillin and diorcinolic acid. From Gastrochilus bellinus, four new compounds, comprising three phenanthropyrans and a phenanthrene derivative, were isolated and structurally characterized. From Huberantha jenkinsii, two new alkaloids of 8-oxoprotoberberine type were isolated along with five known compounds including mangiferin, allantoin, oxylopinine,�N-trans-feruloyl tyramine and N-trans-p-coumaroyl tyramine. The structures of these compounds were determined by UV, IR, MS and NMR spectroscopic methods, and comparison of the data with literature values. Methyl haematommate (IC50 18.7 ? 2.1 ?M), n-docosyl 4-hydroxy-trans-cinnamate (IC50 4.6 ? 0.2 ?M), N-trans-feruloyl tyramine (IC50 30.6 ? 2.9 ?M) and N-trans-p-coumaroyl tyramine (IC50�0.6 ? 0.1 ?M) showed potent ?-glucosidase inhibitory activity in comparison with the drug acarbose (IC50 724.7 ? 46 ?M). N-Docosyl 4-hydroxy-trans-cinnamate at 0.212 mM also displayed 31.6 ? 4.4 %. enhancement of glucose uptake in L6 cells. Mangiferin showed moderate ?-glucosidase inhibition (IC50 253.6 ? 14.2 ?M) and recognizable cellular glucose uptake stimulatory activity (208.1 ? 10.7% enhancement at a concentration of 0.237 mM) as compared with insulin (146.6 ? 35.8 % at a concentration of 500 nM).

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Section: Biological Activity Of Isolated Compoundssupporting

confidence: 84%

Phytochemicals with ?-glucosidase inhibitory activity from cissus javana, dendrobium christyanum, gastrochilus bellinus and huberantha jenkinsii

San

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“…Previously, it was reported that the derivatives of bergenin gave promising -glucosidase inhibition than bergenin. [113] To the best of our knowledge this is the first report of 11-O-acetyl bergenin as -glucosidase inhibitor.…”

Section: -Glucosidase Inhibitory Assay Of K Angustifolia Extracts An...mentioning

confidence: 85%

Antioxidant and antibacterial agents from parmotrema dilatatum (Vainio) hale, knema angustifolia (Roxb.) warb. and persicaria odorata lour

Devi

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In the search of antioxidant and antibacterial agents, the extracts and isolated compounds from lichen Parmotrema dilatatum, Knema angustifolia full name, Persicaria odorata and Mansonia gagei. were examined. Nine compounds were isolated from lichen P. dilatatum including (E)-2,4-dihydroxy-6-methyl-3-(3-oxobut-1-en-1-yl)benzoate (PD.1), hopane-16?,22-diol (PD.2), methyl orsellinate (PD.3), methyl haemmatomate (PD.4), methyl ?-orcinolcarboxylate (PD.5), 2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid (PD.6), atranol (PD.7), atranorin (PD.8) and lecanorin (PD.9). The dichloromethane and acetone fractions, and atranol (PD.7) gave excellent activities as antioxidants. While in tyrosinase activity the dichloromethane fraction and atranorin (PD.8) showed the highest inhibition. For ?-glucosidase inhibition activity, the methanol fraction and methyl haemmatommate (PD.4) revealed the highest activity. The extracts and major constituents from K. angustifolia, P. odorata and M. gagei were determined for their biological activities. Amongst plants K. angustifolia was showed potential activity in DPPH, ABTS, antibacterial, tyrosinase assay and anti ?-glucosidase assay. Meanwhile, quercetin isolated from K. angustifolia exhibited prospective antioxidants, anti-tyrosinase and anti-diabetic activities. MG1 and MG3 derivatives of mansonone G showed synergistic effect against S. aureus when combined with streptomycin. Mansonone G and all derivatives showed synergistic effect against S. aureus and S. mutans when combined with tetracycline.

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Research progress on antidiabetic activity of apigenin derivatives

et al. 2022

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Structure-activity relationships of bergenin derivatives effect on α-glucosidase inhibition

Cited by 7 publications

References 40 publications

Phytochemicals with ?-glucosidase inhibitory activity from cissus javana, dendrobium christyanum, gastrochilus bellinus and huberantha jenkinsii

Phytochemicals with ?-glucosidase inhibitory activity from cissus javana, dendrobium christyanum, gastrochilus bellinus and huberantha jenkinsii

Antioxidant and antibacterial agents from parmotrema dilatatum (Vainio) hale, knema angustifolia (Roxb.) warb. and persicaria odorata lour

Research progress on antidiabetic activity of apigenin derivatives

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