Schistosomicidal Activity of Dihydrobenzofuran Neolignans

Dias, Herbert Júnior; Patrocinio, Andressa Barban do; Pagotti, Mariana Cintra; Fukui, Murilo J.; Rodrigues, Vanderlei; Magalhães, Lizandra G.; Crotti, Antônio Eduardo Miller

doi:10.1002/cbdv.201800134

Cited by 18 publications

(18 citation statements)

References 33 publications

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“…Access to b-5 models with S-S substitution patterns is not possible due to the lack of af ree 5-position on the aromatic ring. However, b-5 Type Cm odels with H-H substitutionp atterns have been accessed via the general methods b-5 Method 1a [108,109] and b-5 Method1b [110] using methyl p-hydroxycinnamate as starting material. The synthesis of mixed G-Sm odelsh as also been accomplished using, for example, b-5 Method1ba nd am ixture of methyl ferulate (21)a nd methyl sinapate.…”

Section: B-5 Type Model Compoundsmentioning

confidence: 99%

An Introduction to Model Compounds of Lignin Linking Motifs; Synthesis and Selection Considerations for Reactivity Studies

et al. 2020

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The development of fundamentally new valorization strategies for lignin plays a vital role in unlocking the true potential of lignocellulosic biomass as sustainable and economically compatible renewable carbon feedstock. In particular, new catalytic modification and depolymerization strategies are required. Progress in this field, past and future, relies for a large part on the application of synthetic model compounds that reduce the complexity of working with the lignin biopolymer. This aids the development of catalytic methodologies and in‐depth mechanistic studies and guides structural characterization studies in the lignin field. However, due to the volume of literature and the piecemeal publication of methodology, the choice of suitable lignin model compounds is far from straight forward, especially for those outside the field and lacking a background in organic synthesis. For example, in catalytic depolymerization studies, a balance between synthetic effort and fidelity compared to the actual lignin of interest needs to be found. In this Review, we provide a broad overview of the model compounds available to study the chemistry of the main native linking motifs typically found in lignins from woody biomass, the synthetic routes and effort required to access them, and discuss to what extent these represent actual lignin structures. This overview can aid researchers in their selection of the most suitable lignin model systems for the development of emerging lignin modification and depolymerization technologies, maximizing their chances of successfully developing novel lignin valorization strategies.

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Section: B-5 Type Model Compoundsmentioning

confidence: 99%

An Introduction to Model Compounds of Lignin Linking Motifs; Synthesis and Selection Considerations for Reactivity Studies

et al. 2020

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“…The DBNs investigated in this study were synthesized as reported previously . Briefly, the core structure of compounds 1 to 8 was obtained by oxidative coupling of coumaric ( a ), ferulic ( b ), and caffeic ( c ) methyl esters promoted by Ag 2 O in acetone/benzene (5:8) mixture.…”

Section: Methodsmentioning

confidence: 99%

“…Dihydrobenzofuran‐type neolignans (DBNs) and their correlated benzofuran‐type derivatives (BNs) are a group of NLs that display two phenylpropanoid units between positions 7‐O‐4′ and 8‐5′. Interest in DBN and BN skeletons stems from their wide spectrum of biological activities, such as trypanocidal, leishmanicidal, schistosomicidal, insecticidal, antioxidant, and anti‐inflammatory actions . The biological effects of synthetic and semisynthetic DBN derivatives have also been extensively investigated …”

Section: Introductionmentioning

confidence: 99%

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

et al. 2018

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We have investigated gas‐phase fragmentation reactions of protonated benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by accurate‐mass electrospray ionization tandem and multiple‐stage (MSn) mass spectrometry combined with thermochemical data estimated by Computational Chemistry. Most of the protonated compounds fragment into product ions B ([M + H–MeOH]+), C ([B–MeOH]+), D ([C–CO]+), and E ([D–CO]+) upon collision‐induced dissociation (CID). However, we identified a series of diagnostic ions and associated them with specific structural features. In the case of compounds displaying an acetoxy group at C‐4, product ion C produces diagnostic ions K ([C–C2H2O]+), L ([K–CO]+), and P ([L–CO]+). Formation of product ions H ([D–H2O]+) and M ([H–CO]+) is associated with the hydroxyl group at C‐3 and C‐3′, whereas product ions N ([D–MeOH]+) and O ([N–MeOH]+) indicate a methoxyl group at the same positions. Finally, product ions F ([A–C2H2O]+), Q ([A–C3H6O2]+), I ([A–C6H6O]+), and J ([I–MeOH]+) for DBNs and product ion G ([B–C2H2O]+) for BNs diagnose a saturated bond between C‐7′ and C‐8′. We used these structure‐fragmentation relationships in combination with deuterium exchange experiments, MSn data, and Computational Chemistry to elucidate the gas‐phase fragmentation pathways of these compounds. These results could help to elucidate DBN and BN metabolites in in vivo and in vitro studies on the basis of electrospray ionization ESI‐CID‐MS/MS data only.

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“…Figure 1) were synthesized as previously reported. 2,6,7,16 All the chemical structures were confirmed by NMR analysis (see Supporting Information).…”

mentioning

confidence: 89%

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

Dias¹,

Crevelin²,

Palaretti³

et al. 2020

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This study elucidates the gas-phase fragmentation pathways of a series of biologically active benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by means of electrospray ionization accurate-mass tandem and sequential mass spectrometry (ESI-MS/MS and ESI-MSn) and thermochemical data estimated by using Computational Chemistry and the B3LYP/6-31+G(d,p) model. In their deprotonated forms, these compounds produced more diagnostic product ions as compared to the corresponding protonated molecules. Moreover, a series of odd-electron product ions (radical anions) were detected, which has not been reported for protonated DBNs. Direct C2H3O2• elimination from the precursor ion (deprotonated molecule) only occurred for the BNs and can help to distinguish these compounds from the DBNs. Although the product ion [M‒CH3OH]‒ emerged in the spectrum of all the DBNs analyzed here, the mechanism through which this ion originates strongly depends on specific structural features, so that further [M‒CH3OH]‒ fragmentation generates important diagnostic product ions. Comparison between the ESI-MS/MS data of these compounds in the negative ion mode (deprotonated molecule) and in the positive ion mode (protonated molecule) revealed that the negative ion mode provides much more information (at least one diagnostic product ion emerged for all the analyzed compounds) and does not require the use of additives to produce the precursor ions (deprotonated molecules).

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Schistosomicidal Activity of Dihydrobenzofuran Neolignans

Cited by 18 publications

References 33 publications

An Introduction to Model Compounds of Lignin Linking Motifs; Synthesis and Selection Considerations for Reactivity Studies

An Introduction to Model Compounds of Lignin Linking Motifs; Synthesis and Selection Considerations for Reactivity Studies

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

Should We Think Positive or Negative About Dihydrobenzofuran Neolignans? an ESI-MS/MS Study

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