Epiberberine, a natural protoberberine alkaloid, inhibits urease of Helicobacter pylori and jack bean: Susceptibility and mechanism

Tan, Lihua; Li, Cailan; Chen, Hanbin; Mo, Zhi-Zhun; Zhou, Jiangtao; Liu, Yuhong; Ma, Zhilin; Xu, Yuyao; Yang, Xiaobo; Xie, Jianhui; Su, Zi‐Ren

doi:10.1016/j.ejps.2017.02.004

Cited by 58 publications

(26 citation statements)

References 43 publications

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“…Our kinetic study using the Lineweaver–Burk plot revealed that coptisine administration resulted in mixed-type inhibition of HPU, which agreed with previous studies of coptisine-induced inhibition patterns in bacterial collagenase from Clostridium histolyticum and in porcine pancreatic elastase 57 , 62 . In contrast, coptisine non-competitively inhibited JBU, which was also the case in our earlier reports on Rhizoma Coptidis extract and the alkaloids epiberberine and palmatine 29 , 32 , 33 . These kinetic mechanism differences might arise from structural differences between HPU and JBU.…”

Section: Discussionsupporting

confidence: 86%

“…The in vitro assay indicated that coptisine inhibited both HPU and JBU in a dose-dependent manner. We previously found that epiberberine and palmatine inhibited urease activity in vitro more effectively than coptisine 32 , 33 . However, H. pylori both contains internal (intracellular) and secretes external (extracellular) ureases, and internal urease in particular is vital for acid neutralisation and H. pylori growth in acidic environments 63 .…”

Section: Discussionmentioning

confidence: 96%

“…Our previous studies have indeed indicated that Rhizoma Coptidis and its major active alkaloids, palmatine and epiberberine, exhibit excellent anti- H. pylori activity and/or inhibit urease, possibly by binding to the urease active site and decreasing the reactivity of active-site thiols in the vicinity of nickel ions 29 , 32 , 33 . However, berberine fails to show any inhibitory activity against urease 29 .…”

Section: Introductionmentioning

confidence: 97%

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Coptisine-induced inhibition ofHelicobacter pylori: elucidation of specific mechanisms by probing urease active site and its maturation process

Huang

Wong

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this study, we examined the anti-Helicobactor pylori effects of the main protoberberine-type alkaloids in Rhizoma Coptidis. Coptisine exerted varying antibacterial and bactericidal effects against three standard H. pylori strains and eleven clinical isolates, including four drug-resistant strains, with minimum inhibitory concentrations ranging from 25 to 50 μg/mL and minimal bactericidal concentrations ranging from 37.5 to 125 μg/mL. Coptisine’s anti-H. pylori effects derived from specific inhibition of urease in vivo. In vitro, coptisine inactivated urease in a concentration-dependent manner through slow-binding inhibition and involved binding to the urease active site sulfhydryl group. Coptisine inhibition of H. pylori urease (HPU) was mixed type, while inhibition of jack bean urease was non-competitive. Importantly, coptisine also inhibited HPU by binding to its nickel metallocentre. Besides, coptisine interfered with urease maturation by inhibiting activity of prototypical urease accessory protein UreG and formation of UreG dimers and by promoting dissociation of nickel from UreG dimers. These findings demonstrate that coptisine inhibits urease activity by targeting its active site and inhibiting its maturation, thereby effectively inhibiting H. pylori. Coptisine may thus be an effective anti-H. pylori agent.

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Section: Discussionsupporting

confidence: 86%

Section: Discussionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 97%

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Coptisine-induced inhibition ofHelicobacter pylori: elucidation of specific mechanisms by probing urease active site and its maturation process

Huang

Wong

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…This alkaloid could be used in the treatment of diseases associated with ureolytic bacteria and could be further developed into a promising therapeutic approach for the treatment of urease-related diseases. 239 Meanwhile, berberine (161) and palmatine 166 Photodynamic therapy was discovered at the beginning of the last century and mostly used as a cancer therapy; however, it has emerged as a promising treatment alternative against infectious diseases. The oxoaporphine alkaloid isomoschatoline (129) had an absorption profile with bands at 600-700 nm, was positive for singlet oxygen production and exhibited photodynamic antimicrobial activity against both Gram-positive and Gram-negative bacteria and some Candida ssp.…”

Section: Antibacterial and Antifungal Activitiesmentioning

confidence: 99%

Biologically active isoquinoline alkaloids covering 2014–2018

Shang

Yang

Morris‐Natschke

et al. 2020

Medicinal Research Reviews

145

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Isoquinoline alkaloids, an important class of N-based heterocyclic compounds, have attracted considerable attention from researchers worldwide since the early 19th century. Over the past 200 years, many compounds from this class were isolated, and most of them and their analogs possess various bioactivities. In this review, we survey the updated literature on bioactive alkaloids and highlight research achievements of this alkaloid class during the period of 2014-2018. We reviewed over 400 molecules with a broad range of bioactivities, including antitumor, antidiabetic and its complications, antibacterial, antifungal, antiviral, antiparasitic, insecticidal, anti-inflammatory, antioxidant, neuroprotective, and other activities. This review should provide new indications or directions for the discovery of new and better drugs from the original naturally occurring isoquinoline alkaloids.

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“…[ 35 ] In addition, berberine could act as a urease inhibitors, which impairs the colonizing and virulent factor of H pylori . [ 36 ] The present study indicated berberine could substitute for bismuth in quadruple therapy with satisfactory eradication rates for treatment-naive patients. Accumulated evidence demonstrated that berberine can effectively inhibit and kill H pylori in vitro, even in multidrug resistant strains.…”

Section: Discussionmentioning

confidence: 62%

Berberine containing quadruple therapy for initial Helicobacter pylori eradication

Zhang

et al. 2017

Medicine

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Background:Due to increasing antimicrobial resistance, a bismuth-based quadruple regimen has been recommended as an alternative first-line therapy for Helicobacter pylori (H pylori) eradication. However, different results are varied greatly and the availability of bismuth was limited in some countries. We assessed the efficacy and safety of 14-day berberine-containing quadruple therapy as an alternative regimen for H pylori eradication.Methods:In a randomized, open-label, non-inferiority, phase IV trial between November 25, 2014, and October 15, 2015, 612 treatment-naive patients were randomly assigned to 14-day berberine-containing (n = 308) or 14-day bismuth-containing (n = 304) quadruple therapy. The primary outcomes were eradication rates determined by the 13C urea breath test (13C-UBT) 28 days after the end of treatment. The secondary outcomes were adverse events and compliance.Results:The baseline demographic data including age, gender, body mass index (BMI), general condition and severity score were not statistically different in both groups. The eradication rates in bismuth and berberine groups were 86.4% (266/308) and 90.1% (274/304) in intention-to-treat (ITT) analysis (P = .149), and 89.6% (266/297) and 91.3% (273/299) in per-protocol (PP) analysis (P = .470), respectively. No statistically significant difference was found in the overall incidence of adverse events between both groups (35.7% vs 28.6%, P = .060).Conclusions:Both regimens achieved the recommended efficacy for H pylori eradication. The berberine-containing quadruple regimen was not inferior to bismuth-containing quadruple regimen and can be recommended as an alternative regimen for H pylori eradication in the local region.

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Epiberberine, a natural protoberberine alkaloid, inhibits urease of Helicobacter pylori and jack bean: Susceptibility and mechanism

Cited by 58 publications

References 43 publications

Coptisine-induced inhibition ofHelicobacter pylori: elucidation of specific mechanisms by probing urease active site and its maturation process

Coptisine-induced inhibition ofHelicobacter pylori: elucidation of specific mechanisms by probing urease active site and its maturation process

Biologically active isoquinoline alkaloids covering 2014–2018

Berberine containing quadruple therapy for initial Helicobacter pylori eradication

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