37622-54-1Relevant academic research and scientific papers
Metabolite profile of Nectandra oppositifolia Nees & Mart. And assessment of antitrypanosomal activity of bioactive compounds through efficiency analyses
Conserva, Geanne A. Alves,Quiros-Guerrero, Luis M.,Costa-Silva, Thais A.,Marcourt, Laurence,Pinto, Erika G.,Tempone, Andre G.,Fernandes, Jo?o Paulo S.,Wolfender, Jean-Luc,Queiroz, Emerson F.,Lago, Jo?o Henrique G.
, (2021/03/15)
EtOH extracts from the leaves and twigs of Nectandra oppositifolia Nees & Mart. shown activity against amastigote forms of Trypanosoma cruzi. These extracts were subjected to successive liquid-liquid partitioning to afford bioactive CH2Cl2 fractions. UHPL
Alkyl hydroxybenzoic acid derivatives that inhibit HIV-1 protease dimerization
Flausino Jr., O. A.,Dufau, L.,Reboud-Ravaux, M.,Regasini, L. O.,Petronio, M. S.,Silva, D. H. S.,Bolzani, V. S.,Rose, T.
, p. 4534 - 4540,7 (2012/12/12)
The therapeutic potential of gallic acid and its derivatives as anti-cancer, antimicrobial and antiviral agents is well known. We have examined the mechanism by which natural gallic acid and newly synthesized gallic acid alkyl esters and related protocatechuic acid alkyl esters inhibit HIV-1 protease to compare the influence of the aromatic ring substitutions on inhibition. We used Zhang-Poorman's kinetic analysis and fluorescent probe binding to demonstrate that several gallic and protecatechuic acid alkyl esters inhibited HIV-1 protease by preventing the dimerization of this obligate homodimeric aspartic protease rather than targeting the active site. The tri-hydroxy substituted benzoic moiety in gallates was more favorable than the di-substituted one in protocatechuates. In both series, the type of inhibition, its mechanism and the inhibitory efficiency dramatically depended on the length of the alkyl chain: no inhibition with alkyl chains less than 8 carbon atoms long. Molecular dynamics simulations corroborated the kinetic data and propose that gallic esters are intercalated between the two N- and C-monomer ends. They complete the β-sheet and disrupt the dimeric enzyme. The best gallic ester (14 carbon atoms, Kid of 320 nM) also inhibited the multi-mutated protease MDR-HM. These results will aid the rational design of future generations of non-peptide inhibitors of HIV-1 protease dimerization that inhibit multi-mutated proteases. Finally, our work suggests the wide use of gallic and protocatechuic alkyl esters to dissociate intermolecular β-sheets involved in protein-protein interactions.
Molecular design of multifunctional food additives: Antioxidative antifungal agents
Nihei, Ken-Ichi,Nihei, Atsuko,Kubo, Isao
, p. 5011 - 5020 (2007/10/03)
A series of alkyl 3,4-dihydroxybenzoates (protocatechuates) was synthesized, and their fungicidal activity against Saccharomyces cerevisiae was assayed using a 2-fold serial broth dilution method. Nonyl and octyl 3,4-dihydroxybenzoate were noted to be the most effective against this yeast with the minimum fungicidal concentration of 12.5 μg/mL each. The activity was found to correlate with the hydrophobic alkyl chain length. The time-kill curve study showed that nonyl 3,4-dihydroxybenzoate was fungicidal against S. cerevisiae at any growth stage and this activity was not influenced by pH values. The fungicidal activity of alkyl 3,4-dihydroxybenzoates was noted in combination with their ability to disrupt the native membrane-associated function nonspecifically as surface-active agents (surfactants) and to inhibit the respiratory electron transport. However, the primary fungicidal activity of nonyl 3,4-dihydroxybenzoate likely comes from its ability to act as a surfactant.
