Dimeric chalcones derivatives from  Myracrodruon urundeuva  act as cathepsin V inhibitors

Sarria, André Lucio Franceschini; Silva, Taynara Lopes; Oliveira, Juliana Magalhães de; Oliveira, Milene Aparecida Rodrigues de; Fernandes, João B.; Silva, Maria Fátima das Graças Fernandes da; Vieira, Paulo C.; Venâncio, Tiago; Filho, Elenilson G. Alves; Batista, João M.; Güido, Rafael Victório Carvalho

doi:10.1016/j.phytochem.2018.06.009

Cited by 11 publications

(9 citation statements)

References 37 publications

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“…This section was adapted from previously published methods 19,31 . All DFT simulations were carried using Gaussian 09 software 32 . Solvation in methanol was treated implicitly using the polarizable continuum model (PCM) in its integral equation formalism version (IEFPCM).…”

Section: Methodsmentioning

confidence: 99%

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Medina

Araújo

Batista

et al. 2019

Sci Rep

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A chemical study of the EtOAc extract of Nemania bipapillata (AT-05), an endophytic fungus isolated from the marine red alga Asparagopsis taxiformis - Falkenbergia stage, led to the isolation of five new botryane sesquiterpenes, including the diastereomeric pair (+)-(2 R ,4 S ,5 R ,8 S )-( 1 ) and (+)-(2 R ,4 R ,5 R ,8 S )-4-deacetyl-5-hydroxy-botryenalol ( 2 ), (+)-(2 R ,4 S ,5 R ,8 R )-4-deacetyl-botryenalol ( 3 ), one pair of diastereomeric botryane nor sesquiterpenes bearing an unprecedented degraded carbon skeleton, (+)-(2 R ,4 R ,8 R )-( 4 ) and (+)-(2 R ,4 S ,8 S )-( 5 ), which were named nemenonediol A and nemenonediol B, respectively, in addition to the known 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial ( 6 ). Their structures were elucidated using 1D and 2D NMR, HRESIMS and comparison with literature data of similar known compounds. The absolute configurations of 2 , 3 and 4 were deduced by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, while those of 1 and 5 were assigned from vibrational circular dichroism (VCD) data. Compound 4 weakly inhibited acetylcholinesterase, whereas compound 1 inhibited both acetylcholinesterase and butyrylcholinesterase. Compounds 1 , 3 , 5 and 6 were tested against two carcinoma cell lines (MCF-7 and HCT-116), but showed no significant citotoxicity at tested concentrations (IC 50 > 50 µM).

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Section: Methodsmentioning

confidence: 99%

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Medina

Araújo

Batista

et al. 2019

Sci Rep

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“…Later, Sarria et ▶ al. [33] revealed that dimeric chalcones strongly inhibited the enzymatic activity of cathepsin V. Urundeuvines D and E were the most active, with IC 50 values of 0.70 and 0.42 µM, respectively. Urundeuvine D is believed to be the most potent natural cathepsin V inhibitor yet studied.…”

Section: Resultsmentioning

confidence: 99%

“…An additional 9 extracts also partially inhibited the growth (determined by growth inhibition equal to or higher than 50 %) of any of the 8 bacteria, all from fungal cocultivation as well. Nine extracts (19,20,30,31,33,34,37,45, and 51) either totally or partially inhibited bacterial growth. In short, 60 positive results were observed (38 instances of total inhibition of bacterial growth and 22 of partial inhibition), all from cocultivation extracts.…”

Section: Resultsmentioning

confidence: 99%

“…Urundeuvine D is believed to be the most potent natural cathepsin V inhibitor yet studied. In the study by Sarria et al [33], the activities of 2 flavonoids (luteolin and 5,2′-dihydroxy-3-methoxy-6,7-(2′,2′-dimethylchromene)-8-(3′′,3′′-dimethylallylflavanone), with IC 50 values of 2.5 and 13.5 µM, respectively were discussed. Recently, Silva et al [34] determined the cathepsin V inhibition activity of 8-methoycoumestrol (IC 50 of 17.4 ± 1.0 µM) and a trans-p-coumaric acid ester derivative (94 % inhibition at 50 µg/ mL).…”

Section: Resultsmentioning

confidence: 99%

“…Cathepsin V inhibition was evaluated in vitro as previously described [32,33]. Briefly, the enzymatic activity was measured by the increase in fluorescence from the hydrolysis of the Z-FR-MCA substrate (Z-Phe-Arg-7-amido-4-methylcoumarin) by cathepsin V, releasing MCA.…”

Section: Bioassay Of Cathepsin V Inhibitionmentioning

confidence: 99%

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Liquid Fungal Cocultivation as a Strategy to Access Bioactive Metabolites

et al. 2020

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AbstractFungi are a rich source of bioactive compounds. Fungal cocultivation is a method of potentiating chemical interactions and, consequently, increasing bioactive molecule production. In this study, we evaluated the bactericidal, antiprotozoal, and cathepsin V inhibition activities of extracts from axenic cultures of 6 fungi (Fusarium guttiforme, Pestalotiopsis diospyri, Phoma caricae-papayae, Colletotrichum horii, Phytophthora palmivora, and C. gloeosporioides) that infest tropical fruits and 57 extracts obtained by their cocultivation. Our results reveal that fungal cocultivation enhances the biological activity of the samples, since all extracts that were active on Gram-positive bacteria, Gram-negative bacteria, Trypanosoma cruzi, and Leishmania infantum were obtained from cocultivation. Bacterial growth is either totally or partially inhibited by 46% of the extracts. Two extracts containing mainly fusaric and 9,10-dehydrofusaric acids were particularly active. The presence of the fungus F. guttiforme in co-cultures that give rise to extracts with the highest activities against L. infantum. An axenic culture gave rise to the most active extract for the inhibition of cathepsin V; however, other coculture extracts also exhibited activity toward this biological target. Therefore, the results of the biological activities indicate that fungal cocultivation increased the biological potential of samples, likely due to the hostile and competitive environment that pushes microorganisms to produce substances important for defense and allows access to metabolic routes then silenced in milder cultivation conditions.

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The impact of global climate change on the number and replacement of provisioning ecosystem services of Brazilian Cerrado plants

Ferreira

Parreira

Nabout

2021

Environ Monit Assess

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Dimeric chalcones derivatives from Myracrodruon urundeuva act as cathepsin V inhibitors

Cited by 11 publications

References 37 publications

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Liquid Fungal Cocultivation as a Strategy to Access Bioactive Metabolites

The impact of global climate change on the number and replacement of provisioning ecosystem services of Brazilian Cerrado plants

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