Dimeric acylphloroglucinols from Hypericum austrobrasiliense exhibiting antinociceptive activity in mice

Bridi, Henrique; Ccana-Ccapatinta, Gari V.; Stolz, Eveline Dischkaln; Meirelles, Gabriela de Carvalho; Bordignon, Sérgio A. L.; Rates, Stela Maris Kuze; Poser, Gilsane Lino von

doi:10.1016/j.phytochem.2015.12.012

Cited by 13 publications

(12 citation statements)

References 18 publications

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“…Hypericum species belonging to Brathys and Trigynobrathys sections are an important source of dimeric acylphloroglucinols. Until now, 36 compounds were isolated from these species [1][2][3]9]. Hypericum denudatum afforded a new dimeric phloroglucinol, denudatin A (1), and three compounds that have already been described, hyperbrasilol A (3), uliginosin B (4), and isouliginosin B (5).…”

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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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“…The obtained extracts were submitted to chromatographic procedures as previously described to isolate the phloroglucinol derivatives austrobrasilol A ( 1 ), japonicin A ( 2 ), 6‐isobutyryl‐5,7‐dimethoxy‐2,2‐dimethyl‐benzopyran (HP1) ( 3 ), 7‐hydroxy‐6‐isobutyryl‐5‐methoxy‐2,2‐dimethyl‐benzopyran (HP2) ( 4 ) and 5‐hydroxy‐6‐isobutyryl‐7‐methoxy‐2,2‐dimethyl‐benzopyran (HP3) ( 5 ), isoaustrobrasilol B ( 6 ), uliginosin B ( 7 ), hyperbrasilol B ( 8 ), and austrobrasilol B ( 9 ) (Figure ). Isouliginosin B and isohyperbrasilol B were isolated from Peruvian Hypericum species as described elsewhere and kindly donated by MSc.…”

Section: Methodsmentioning

confidence: 99%

“…These well‐known effects are attributed to flavonoids, naphthodianthrones, such as hypericin, and especially to the monomeric acylphloroglucinols hyperforin and adhyperforin . A wide variety of phloroglucinols have been characterized in Hypericum species from southern Brazil with established antidepressant‐like and antinociceptive activities. In addition to these activities in central nervous system, studies have already demonstrated the antiparasitic activities of lipophilic Hypericum extracts and of isolated compounds in T. vaginalis and L. amazonensis …”

Section: Introductionmentioning

confidence: 99%

The anti‐Trichomonas vaginalis phloroglucinol derivative isoaustrobrasilol B modulates extracellular nucleotide hydrolysis

et al. 2017

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Trichomonas vaginalis causes trichomoniasis, a neglected sexually transmitted disease. Due to severe health consequences and treatment failure, new therapeutic alternatives are crucial. Phloroglucinols from southern Brazilian Hypericum species demonstrated anti-T. vaginalis and anti-Leishmania amazonensis activities. The modulation of biochemical pathways involved in the control of inflammatory response by ectonucleotidases, NTPDase, and ecto-5'-nucleotidase represents new targets for combating protozoa. This study investigated the activity of phloroglucinol derivatives of Hypericum species from southern Brazil against T. vaginalis as well as its ability on modulating parasite ectonucleotidases and, consequently, immune parameters through ATP and adenosine effects. Phloroglucinol derivatives screening revealed activity for isoaustrobrasilol B (IC 38 μm) with no hemolytic activity. Although the most active compound induced cytotoxicity against a mammalian cell lineage, the in vivo model evidenced absence of toxicity. Isoaustrobrasilol B significantly inhibited NTPDase and ecto-5'-nucleotidase activities, and the immune modulation attributed to extracellular nucleotide accumulation was evaluated. The production of ROS and IL-6 by T. vaginalis-stimulated neutrophils was not affected by the treatment. Conversely, IL-8 levels were significantly enhanced. The associative mechanism of trophozoites death and ectonucleotidases modulation by isoaustrobrasilol B may increase the susceptibility of T. vaginalis to host innate immune cell like neutrophils consequently, contributing to parasite clearance.

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“…90 : 10) were chromatographed with CPC (1 mm layer; SiO 2 GF 254 plates; 10 mL fractions) using gradient elution of hexane/AcOEt (100:0!80 : 20) as mobile phase, affording 19 subfractions (Subfrs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. From Subfrs.…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…[9 -11] Benzopyran HP1 and selancin A, isolated from these extracts, as well as the dimeric acylphloroglucinols uliginosin B, austrobrasilol A, austrobrasilol B, isoaustrobrasilol B and denudatin A demonstrated this activity, reducing the thermal pain after oral administration. [11][12][13][14][15] Considering the importance of the genus Hypericum as producer of biologically active compounds and the continuing search for novel phloroglucinol derivatives with potential antinociceptive activity, an effort was made to isolate and identify additional constituents of four Brazilian Hypericum species, aiming to determine the antinociceptive effect of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive Activity of Phloroglucinol Derivatives Isolated from Southern Brazilian Hypericum Species

Bridi

Stolz

Barros

et al. 2018

Chemistry & Biodiversity

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The south Brazilian Hypericum species have revealed the presence of a series of biologically active phloroglucinol derivatives. In this study, a mixture of japonicine A and an isomer with an unreported structure, named japonicine E, was isolated from the roots of H. polyanthemum. Additionally, uliginosin A from H. myrianthum, isouliginosin B from H. polyanthemum, hyperbrasilol B and isohyperbrasilol B from H. caprifoliatum and cariphenone A from H. carinatum were also isolated. The structures were elucidated using 1D- and 2D-NMR experiments and by comparison with previously reported data. The compounds japonicines A/E, uliginosin A, isouliginosin B, hyperbrasilol B and cariphenone A exhibited antinociceptive activity in the mice hot-plate test and did not induce motor impairment in the rotarod apparatus.

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Dimeric acylphloroglucinols from Hypericum austrobrasiliense exhibiting antinociceptive activity in mice

Cited by 13 publications

References 18 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

The anti‐Trichomonas vaginalis phloroglucinol derivative isoaustrobrasilol B modulates extracellular nucleotide hydrolysis

Antinociceptive Activity of Phloroglucinol Derivatives Isolated from Southern Brazilian Hypericum Species

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