Uliginosin B, a natural phloroglucinol derivative, presents a multimediated antinociceptive effect in mice

Stolz, Eveline Dischkaln; Hasse, Diego Rafael; Poser, Gilsane Lino von; Rates, Stela Maris Kuze

doi:10.1111/jphp.12307

Cited by 11 publications

(10 citation statements)

References 54 publications

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“…Five compounds isolated from Brazilian Hypericum species were already evaluated for their antinociceptive activity (uliginosin B, benzopyran HP1, austrobrasilol A, austrobrasilol B, and isoaustrobrasilol B) [3,10,13]. Uliginosin B and benzopyran HP1 promote their effects mediated by the activation of glutamatergic and opioid receptors, and by an opioid-like mechanism, respectively [10][11][12][13]. It is relevant to evaluate the antinociceptive effect of denudatin A (1) and selancin A (2) because these compounds present some different chemical features in relation to the previously tested phloroglucinol derivatives.…”

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confidence: 99%

“…To exclude that the behavior in the hot plate would be due to a sedative, muscle relaxant, or hypotensive actions, the motor performance of the mice treated with denudatin A (1) and selancin A (2) was evaluated in the rotarod apparatus. The analysis of the results (two-way RM ANOVA) demonstrated a main effect of the treatment and exposition session as well interaction between factors when considering the number of falls (▶ Recently, studies have demonstrated the antinociceptive activity of the dimeric acylphloroglucinols austrobrasilol A, austrobrasilol B, isoaustrobrasilol B [3], and especially, uliginosin B (4) [11][12][13]. The mechanism of action of uliginosin B seems to be due to the neuronal monoamine reuptake inhibition [8] with consequent activation of dopaminergic receptors and indirect stimulation of the opioid system [11].…”

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Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice

et al. 2017

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A new dimeric acylphloroglucinol, denudatin A (), was isolated from the flowering aerials parts of , along with the known phloroglucinols selancin A (), hyperbrasilol A (), uliginosin B (), and isouliginosin B (). The structure of was elucidated using 1D, 2D NMR, and MS experiments, and by comparison with previously reported data for dimeric acylphloroglucinols. Denudatin A () and selancin A () were administered orally to mice displaying antinociceptive activity in the hot plate test. The compounds did not induce motor impairment in the rotarod apparatus.

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Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice

et al. 2017

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“…Previous data showed that ULI (15 mg/kg, i.p.) produces antinociceptive effect in hot-plate test [ 3 , 5 , 6 ]. We now show that the pretreatment with DPCPX and ZM 241385, selective adenosine A 1 and A 2A receptor antagonists, respectively, completely prevented the antinociceptive effect of ULI in the mice hot-plate test.…”

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confidence: 99%

“…Uliginosin B (ULI) is a dimeric acylphloroglucinol consisting of filicinic acid and phloroglucinol moieties, which occurs in Hypericum species native to South America [ 1 ]. This molecular pattern has been proposed as a prototype to develop analgesic and antidepressant drugs [ 2 – 5 ].…”

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confidence: 99%

“…It is noteworthy that ULI deserves attention as a drug potentially useful to reduce the dose of morphine in clinical practice [ 6 ]. Its antinociceptive effect involves the activation of monoaminergic, glutamatergic, and opioid receptors, apparently without binding to these receptors [ 2 , 3 , 5 ]. Therefore, other molecular targets for ULI might be considered.…”

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Uliginosin B, a Possible New Analgesic Drug, Acts by Modulating the Adenosinergic System

Stolz

Costa

Medeiros

et al. 2016

Evidence-Based Complementary and Alternative Medicine

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Uliginosin B (ULI) is a natural acylphloroglucinol that has been proposed as a new molecular scaffold for developing analgesic and antidepressant drugs. Its effects seem to be due to its ability to increase monoamines in the synaptic cleft by inhibiting their neuronal uptake without binding to their respective transporters, but its exact mode of action is still unknown. Considering the importance of the purinergic system to pain transmission and its modulation by monoamines availability, the aim of this study was to investigate the involvement of adenosinergic signaling in antinociceptive effect of uliginosin B. The selective adenosine A1 receptor antagonist DPCPX and the selective A2A antagonist ZM 241385 prevented the effect of ULI in the hot-plate test in mice. Pretreatment with inhibitors of adenosine reuptake (dipyridamole) or adenosine deaminase (EHNA) did not affect the ULI effect. On the other hand, its effect was completely prevented by an inhibitor of ecto-5′-nucleotidase (AMPCP). This finding was confirmed ex vivo, whereby ULI treatment increased AMP and ATP hydrolysis in spinal cord and cerebral cortex synaptosomes, respectively. Altogether, these data indicate that activation of A1 and A2A receptors and the modulation of ecto-5′-nucleotidase activity contribute to the antinociceptive effect of ULI.

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Antidepressant Drug Discovery and Development: Mechanism and Drug Design Based on Small Molecules

Yao

Jiang

et al. 2022

Advanced Therapeutics

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Depression is one of the most prevalent mental diseases and a primary cause of disability worldwide with high incidence and high recurrence. The current deterioration of the COVID‐19 epidemic also pushes up the incidence of depression. Nevertheless, the currently available treatments remain inadequate response and limited efficacy. Therefore, discoveries of more potent and safer antidepressant drugs are urgently needed. In this review, the current potential physiological and pathological mechanisms of depression, and the clinical research progresses of candidate drugs as well as the recent advances in small‐molecule drug discovery for potential treatments of depression are systematically summarized. More importantly, the structure–activity relationships of compounds from different classes, the statistical analysis of the blood‐brain barrier permeability, the pharmacological targets, and the in vivo models are comprehensively discussed. Further insights on antidepressant drug discovery are also analyzed from multidimensional perspectives.

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Uliginosin B, a natural phloroglucinol derivative, presents a multimediated antinociceptive effect in mice

Abstract: These data confirm the contribution of monoaminergic neurotransmission as well as provide the first evidence of glutamatergic neurotransmission contribution to the uliginosin B effects.

Cited by 11 publications

References 54 publications

Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice

Denudatin A, a Dimeric Acylphloroglucinol from Hypericum denudatum Presents an Antinociceptive Effect in Mice

Uliginosin B, a Possible New Analgesic Drug, Acts by Modulating the Adenosinergic System

Antidepressant Drug Discovery and Development: Mechanism and Drug Design Based on Small Molecules

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