Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Mazzeu, Bruna Fonseca; Felippe, Lidiane Gaspareto; Cotinguiba, Fernando; Kato, Massuo Jorge; Furlan, Maysa

doi:10.21577/0103-5053.20170225

Cited by 2 publications

(2 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2. Flavanones and prenylated benzoic acid derivatives [30,35,[41][42][43] have been reported from various Piper species. However, a compound having both of these moieties has not been reported.…”

Section: Resultsmentioning

confidence: 99%

Anti-trypanosomal screening of Salvadoran flora

et al. 2021

View full text Add to dashboard Cite

Chagas disease is caused by the protozoan parasite Trypanosoma cruzi, and in Central America, it is considered one of the four most infectious diseases. This study aimed to screen the anti-trypanosomal activity of plant species from Salvadoran flora. Plants were selected through literature search for plants ethnobotanically used for antiparasitic and Chagas disease symptomatology, and reported in Museo de Historia Natural de El Salvador (MUHNES) database. T. cruzi was incubated for 72 h with 2 different concentrations of methanolic extracts of 38 species, among which four species, Piper jacquemontianum, Piper lacunosum, Trichilia havanensis, and Peperomia pseudopereskiifolia, showed the activity (≤ 52.0% viability) at 100 µg/mL. Separation of the methanolic extract of aerial parts from Piper jacquemontianum afforded a new flavanone (4) and four known compounds, 2,2-dimethyl-6-carboxymethoxychroman-4-one (1), 2,2-dimethyl-6-carboxychroman-4-one (2), cardamomin (3), and pinocembrin (5), among which cardamomin exhibited the highest anti-trypanosomal activity (IC50 = 66 µM). Detailed analyses of the spectral data revealed that the new compound 4, named as jaqueflavanone A, was a derivative of pinocembrin having a prenylated benzoate moiety at the 8-position of the A ring. Graphic abstract

show abstract

Section: Resultsmentioning

confidence: 99%

Anti-trypanosomal screening of Salvadoran flora

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The chemical diversity of Piperaceae is commonly known, and phytochemical studies have led to the isolation of amides involved in important biological activities, including several examples that highlight the potential for the development of new antifungal, antitumor, and trypanocidal agents (Bosc et al, 2018;Silva et al, 2002;Valli et al, 2017;Vieira et al, 2018). In addition to aliphatic and aromatic piperamides (Alécio et al, 1998;Cotinguiba et al, 2009;Navickiene et al, 2000), several classes of compounds have been isolated from Piper species, including lignans (Felippe et al, 2008), polyketides (Cheng et al, 2003), piperolides (Lago et al, 2005), benzoic acid derivatives (Baldoqui et al, 1999;Morandim et al, 2005), kavalactones (Mazzeu et al, 2018), chromenes, and prenylated chromenes (Batista Júnior et al, 2008;Mota et al, 2009).…”

Section: Protocol For Obtaining Enzyme Source For Monitoring Of the A...mentioning

confidence: 99%

Amino acids L-phenylalanine and L-lysine involvement in trans and cis piperamides biosynthesis in two Piper species

et al. 2022

View full text Add to dashboard Cite

Several Piper species accumulate piperamides as secondary metabolites, and although they have relevant biological importance, many details of their biosynthetic pathways have not yet been described experimentally. Experiments involving enzymatic reactions and labeled precursor feeding were performed using the species Piper tuberculatum and Piper arboreum. The activities of the phenylalanine ammonia lyase (PAL) enzymes, which are involved in the general phenylpropanoid pathway, were monitored by the conversion of the amino acid L-phenylalanine to cinnamic acid. The activity of the 4-hydroxylase (C4H) enzyme was also observed in P. tuberculatum by converting cinnamic acid to p-coumaric acid. L-[UL-14C]-phenylalanine was fed into the leaves of P. tuberculatum and incorporated into piperine (1), 4,5-dihydropiperine (2), fagaramide (4), trans-piplartine (7), and dihydropiplartine (9). In P. arboreum, it was only incorporated into the piperamide 4,5-dihydropiperiline (3). L-[UL-14C]-lysine was successfully incorporated into the 4,5-dihydropiperine piperidine group (2), dihydropyridinone, and trans- (7) and cis-piplartine (8). These data corroborate the proposal of mixed biosynthetic origin of piperamides with the aromatic moiety originating from cinnamic acid (shikimic acid pathway) and key amide construction with amino acids as precursors.

show abstract

Kavalactones and Benzoic Acid Derivatives from Leaves of Piper fuligineum Kunth (Piperaceae)

Cited by 2 publications

References 24 publications

Anti-trypanosomal screening of Salvadoran flora

Anti-trypanosomal screening of Salvadoran flora

Amino acids L-phenylalanine and L-lysine involvement in trans and cis piperamides biosynthesis in two Piper species

Contact Info

Product

Resources

About