Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity

Takahashi, Hironobu; Kosaka, Masamiti; Watanabe, Yasutoshi; Nakade, Kousuke; Fukuyama, Yoshiyasu

doi:10.1016/s0968-0896(02)00666-1

Cited by 111 publications

(82 citation statements)

References 25 publications

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“…Bergenin has been widely used for the treatment of chronic bronchitis and has other effects such as antitussive, hepatoprotective, anti-infl ammatory, neuroprotective and weak anti-HIV activities [3][4][5][6] . Although bergenin has been used for more than 30 years, its poor oral bioavailability is still an obstacle to its further application [7] .…”

Section: Introductionmentioning

confidence: 99%

Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex

et al. 2009

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Aim: To prepare a bergenin-phospholipid complex (BPC) to increase oral bioavailability of the drug. Methods: In order to obtain the acceptable BPC, a spherical symmetric design-response surface methodology was used for process optimization. The infl uence of reaction medium, temperature, drug concentration and drug-to-phospholipid ratio on the combination percentage and content of bergenin in BPC were evaluated. BPC was then characterized by thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), ultra-violet (UV) spectroscopy, fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC) and X-ray powder diffraction. The physicochemical properties such as microscopic shape, particle size, zetapotential, solubility, crystalline form, and hygroscopicity were tested. The pharmacokinetic characteristics and bioavailability of BPC were investigated after oral administration in rats in comparison to bergenin and the physical mixture (bergenin and phospholipids). Results: BPC was successfully prepared under the optimum conditions [temperature=60 °C, drug concentration=80 g/L and drug-tophospholipids ratio=0.9 (w/w)]. The combination percentage was 100.00%±0.20%, and the content of bergenin in the complex was 45.98%±1.12%. Scanning electron microscopy and transmission electron microscopy of BPC showed spherical particles. The average particle size was 169.2±20.11 nm and the zeta-potential was −21.6±2.4 mV. The solubility of BPC in water and in n-octanol was effectively enhanced. The C max and AUC 0→∞ of BPC were increased, and the relative bioavailability was signifi cantly increased to 439% of bergenin. Conclusion: The BPC is a valuable delivery system to enhance the oral absorption of bergenin.

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Section: Introductionmentioning

confidence: 99%

Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex

et al. 2009

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“…As shown in Table 2, all bergenin analogues 2-10 exhibited a significant degree of β-secretase inhibition IC 50 values: 0.6-66.1 mM in in vitro BACE1 activity assays. In particular, 11-O-protocatechuoylbergenin 5 showed excellent inhibition of BACE1 with extremely high potency, and its IC 50 value was calculated as 0.6 mM. 11-O-Protocatechuoylbergenin 5 , having 2 OH groups at C-3 and C-4 , showed the strongest inhibitory activity among the bergenin analogues 2-10 .…”

Section: Dpph Radical Scavenging Activity Of Bergenin and Its Analogumentioning

confidence: 98%

“…The antioxidant activities of compounds 1-10 were evaluated by their EC 50 50 Effective Concentration in DPPH radical scavenging activity as shown in Figs. 3 and 4.…”

Section: Dpph Radical Scavenging Activity Of Bergenin and Its Analogumentioning

confidence: 99%

“…Therefore, ROS play key roles in the initiation and progression of many neurodegenerative diseases of the central nervous system such as Alzheimer s and Parkinson s disease 49 . In addition, a previous study showed that antioxidants such as flavonoid glycosides and a triterpene ester exert neuroprotective activity 50 . These findings indicate that the neuroprotective effects against AD might be mediated by reduced intracellular ROS generation.…”

Section: Figurementioning

confidence: 99%

“…These findings indicate that the neuroprotective effects against AD might be mediated by reduced intracellular ROS generation. Moreover, Takahashi et al showed that esterification of hydroxy groups at C11 of bergenin with various fatty acids enhanced antioxidant and neuroprotective activities 50 . Almost all bergenin analogues, in particular 11-Oprotocatechuoylbergenin 5 , possess stronger antioxidative properties than that of bergenin, a known antioxidant.…”

Section: Figurementioning

confidence: 99%

See 2 more Smart Citations

Structure-activity Relationships for Bergenin Analogues as ^|^beta;-Secretase (BACE1) Inhibitors

Kashima

Miyazawa

2013

J. Oleo Sci.

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Determination of bergenin in human plasma after oral administration by HPLC‐MS/MS method and its pharmacokinetic study

Wang

Wei

et al. 2008

Biomedical Chromatography

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A highly sensitive, simple and selective high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed and applied to the determination of bergenin concentration in human plasma. Bergenin and the internal standard (IS) thiamphenicol in plasma were extracted with ethyl acetate, separated on a C(18 )reversed-phase column, eluted with mobile phase of acetonitrile-water, ionized by negative ion pneumatically assisted electrospray and detected in the multi-reaction monitoring mode using precursor --> product ions of m/z 327.1 --> 192 for bergenin and 354 --> 185.1 for the IS, respectively. The linear range of the calibration curve for bergenin was 0.25-60 ng mL(-1), with the lowest limit of quantification of 0.25 ng mL(-1), and the intra/inter-day relative standard deviation (RSD) was less than 10%. The method is suitable for the determination of low bergenin concentration in human plasma after therapeutic oral doses, and has been first and successfully used for its pharmacokinetic studies in healthy Chinese volunteers.

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Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity

Cited by 111 publications

References 25 publications

Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex

Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex

Structure-activity Relationships for Bergenin Analogues as ^|^beta;-Secretase (BACE1) Inhibitors

Determination of bergenin in human plasma after oral administration by HPLC‐MS/MS method and its pharmacokinetic study

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