Isolation and Quantitative Analysis of BACE1 Inhibitory Compounds from <i>Cirsium maackii</i> Flower

Bhatarrai, Grishma; Seong, Su Hui; Jung, Hyun Ah; Choi, Jae Sue

doi:10.20307/nps.2019.25.4.326

Cited by 6 publications

(6 citation statements)

References 35 publications

(49 reference statements)

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“…The antibacterial activities including anti-H. pylori activity of emodin have been reported previously, ,, but the urease inhibitory activity and anti-H. pylori activity of the anthraquinone glycoside, chrysophanol-8- O- β- d -glucoside, were reported for the first time in this study.…”

Section: Resultsmentioning

confidence: 50%

“…Among the compounds, potent inhibitory activity was measured from emodin (1) and chrysophanol-8-O-β-D-glucoside (5). The antibacterial activities including anti-H. pylori activity of emodin have been reported previously, 24,27,28 but the urease inhibitory activity and anti-H. pylori activity of the anthraquinone glycoside, chrysophanol-8-O-β-D-glucoside, were reported for the first time in this study. Although the anti-H. pylori activity of R. acetosa extract was previously reported, 29 this is the first report on compounds isolated from this plant.…”

Section: Resultsmentioning

confidence: 51%

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Anti-Helicobacter pylori Activity of Six Major Compounds Isolated from Rumex acetosa

Kang,

Khalil,

Park

et al. 2023

ACS Omega

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Gastric problems are often caused by the well-known Helicobacter pylori (H. pylori) bacterium. One of the biggest obstacles to the treatment of H. pylori infections is increasing the antibiotic resistance. During our search for naturally derived anti-H. pylori compounds, six major compounds were isolated from the methylene chloride (CH 2 Cl 2 ) and ethyl acetate (EtOAc) fractions of Rumex acetosa that showed anti-H. pylori activity. Three anthraquinones and three anthraquinone glucosides were identified as the major chemical constituents of the CH 2 Cl 2 and EtOAc fractions, respectively. The chemical structures were identified to be emodin (1), chrysophanol (2), physcion (3), emodin-8-O-β-D-glucoside (4), chrysophanol-8-O-β-Dglucoside (5), and physcion-8-O-β-D-glucoside (6) by UV, 1 H NMR, 13 C NMR, and mass spectrometry. Anti-H. pylori activity, including the minimum inhibitory concentration (MIC) value of each compound, was evaluated against two H. pylori strains. All isolates exhibited anti-H. pylori activity with different potencies, with an MIC value ranging between 3.13 and 25 μM. However, some variations were found between the two strains. While compound 5 displayed the most potent antibacterial activity with an MIC 50 value of 8.60 μM and an MIC 90 value of 15.7 μM against H. pylori strain 51, compound 1 exhibited the most potent inhibitory activity against H. pylori strain 43504. The two compounds also showed moderate urease inhibitory activity, with compound 1 demonstrating activity higher than that of compound 5. Furthermore, a molecular docking study revealed the high binding ability of compounds 1 and 5 to the active site of H. pylori urease. The present study suggests that the six anthraquinones isolated from R. acetosa with the whole parts of this plant may be natural candidates for the treatment of H. pylori infection. Further studies are required to determine the exact mechanism of action and to evaluate safety issues in the human body.

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Section: Resultsmentioning

confidence: 50%

Section: Resultsmentioning

confidence: 51%

Anti-Helicobacter pylori Activity of Six Major Compounds Isolated from Rumex acetosa

Kang,

Khalil,

Park

et al. 2023

ACS Omega

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“…By comparing the spectroscopic data with those reported in the literature, the known compounds were identified as isorhamnetin- bis -3,7- O - β - d -glucuronide ( 2 ), kaempferol- bis -3,7- O - β - d -glucuronide ( 3 ), quercetin- bis -3,7- O - β - d -glucuronide ( 4 ) [ 26 , 27 ] quercetin-3- O - β - d -glucuronide ( 5 ) [ 28 ], kaempferol-3- O - β - d -glucuronide ( 6 ) [ 29 ], isorhamnetin-3- O - β - d -glucuronide ( 7 ) [ 30 ], quercetin-3- O - β - d -glucuronide-6″-methyl ester ( 8 ) [ 31 ], isoquercitrin ( 9 ) [ 32 ], tiliroside ( 10 ) [ 33 ], quercetin-3′- O - β - d -glucuronide ( 11 ) [ 34 ], apigenin-7- O - β - d -glucuronide ( 12 ) [ 35 ], luteolin-7- O - β - d -glucuronide ( 13 ) [ 35 ], ellagic acid ( 14 ) [ 36 ], and brevifolin carboxylic acid ( 15 ) [ 37 ].…”

Section: Resultsmentioning

confidence: 99%

Potentilloside A, a New Flavonol-bis-Glucuronide from the Leaves of Potentilla chinensis, Inhibits TNF-α-Induced ROS Generation and MMP-1 Secretion

Lee

Choi

Son

et al. 2022

Plants

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The major contributor to skin aging is UV radiation, which activates pro-inflammatory cytokines including TNF-α. TNF-α is involved in the acceleration of skin aging via ROS generation and MMP-1 secretion. In our preliminary study, a 30% EtOH extract from the leaves of Potentilla chinensis (LPCE) significantly inhibited TNF-α-induced ROS generation in human dermal fibroblasts (HDFs). Therefore, the objective of this study is to identify the active components in LPCE. A new flavonol-bis-glucuronide (potentilloside A, 1) and 14 known compounds (2–15) were isolated from an LPCE by repeated chromatography. The chemical structure of the new compound 1 was determined by analyzing its spectroscopic data (NMR and HRMS) and by acidic hydrolysis. Nine flavonols (2–9 and 11) and two flavone glycosides (12 and 13) from P. chinensis were reported for the first time in this study. Next, we evaluated the effects of the isolates (1–15) on TNF-α-induced ROS generation in HDFs. As a result, all compounds significantly inhibited ROS generation. Furthermore, LPCE and potentilloside A (1) remarkably suppressed MMP-1 secretion in HDFs stimulated by TNF-α. The data suggested that LPCE and potentilloside A (1) are worthy of further experiments for their potential as anti-skin aging agents.

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“…Lee et al [18] verified that the highest constituent from EtOAc fraction of CJM is cirsimaritin, following cirsimarin and hispidulin. In addition, apigenin and luteolin are major constituents in the EtOAc fraction of CJM flower [19]. In particular, we reported that pectolinarin from the EtOAc fraction of CJM has neuroprotective effects [20].…”

Section: Introductionmentioning

confidence: 88%

Cirsium japonicum var. Maackii Improves Cognitive Impairment under Amyloid Beta25-35-Induced Alzheimer’s Disease Model

Pang

Kim

Choi

et al. 2022

BioMed Research International

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Abnormal production and degradation of amyloid beta (Aβ) in the brain lead to oxidative stress and cognitive impairment in Alzheimer’s disease (AD). Cirsium japonicum var. maackii (CJM) is widely used as an herbal medicine and has antibacterial and anti-inflammatory properties. This study focused on the protective effect of the ethyl acetate fraction from CJM (ECJM) on Aβ25-35-induced control mice. In the T-maze and novel object recognition test, ECJM provided higher spatial memory and object recognition compared to Aβ25-35 treatment alone. In the Morris water maze test, ECJM-administered mice showed greater learning and memory abilities than Aβ25-35-induced control mice. Additionally, ECJM-administered mice experienced inhibited lipid peroxidation and nitric oxide production in a dose-dependent manner. The present study indicates that ECJM improves cognitive impairment by inhibiting oxidative stress in Aβ25-35-induced mice. Therefore, CJM may be useful for the treatment of AD and may be a potential material for functional foods.

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Isolation and Quantitative Analysis of BACE1 Inhibitory Compounds from Cirsium maackii Flower

Cited by 6 publications

References 35 publications

Anti-Helicobacter pylori Activity of Six Major Compounds Isolated from Rumex acetosa

Anti-Helicobacter pylori Activity of Six Major Compounds Isolated from Rumex acetosa

Potentilloside A, a New Flavonol-bis-Glucuronide from the Leaves of Potentilla chinensis, Inhibits TNF-α-Induced ROS Generation and MMP-1 Secretion

Cirsium japonicum var. Maackii Improves Cognitive Impairment under Amyloid Beta25-35-Induced Alzheimer’s Disease Model

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