A New Ferulic Acid Ester, a New Ellagic Acid Derivative, and Other Constituents from Pachycentria formosana: Effects on Neutrophil Pro‐Inflammatory Responses

Abstract

A new ferulic acid ester derivative, tetracosane-1,24-diyl di[(Z)-ferulate] (1), and a new ellagic acid derivative, 3,4 : 3',4'-bis(O,O-methylene)ellagic acid (2), have been isolated from leaves and twigs of Pachycentria formosana, together with eight known compounds. Their structures were determined by in-depth spectroscopic and mass-spectrometric analyses. Among the isolated compounds, oleanolic acid (6), ursolic acid acetate (7), and 3-epibetulinic acid (9) exhibited potent inhibition (IC(50) values ≤ 21.8 μM) of O₂(-) generation by human neutrophils in response to N-formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). In addition, oleanolic acid (6), 3-O-[(E)-feruloyl]ursolic acid (8), 3-epibetulinic acid (9), and lawsonic acid (10) also inhibited fMLP/CB-induced elastase release with IC(50) values ≤ 18.6 μM.

Biopharmaceutical Activities Related to Ellagic Acid, Chitosan, and Zein and Their Improvement by Association

“…(), EA at 25 μg/mL has shown 68% collagenase inhibition, in close agreement to our findings. EA metabolites were able to inhibit the release of elastase by human neutrophils (Cho et al., ). Thus, the antielastase and anticollagenase activities aforementioned would be other mechanisms to contribute for the skin and connective tissues repairing and represent a great potential for functional food, therapeutic, and cosmetic uses of EA.…”

Antagonism of human formyl peptide receptor 1 with natural compounds and their synthetic derivatives

“…Oleanolic (Table 1), ursolic, and betulinic acids are known triterpenes with anti-inflammatory and immunomodulatory properties [142]. Oleanolic acid has been reported to inhibit f MLF-induced responses, including O 2 −· and HNE production by neutrophils [143–146]. The activity of this triterpene on O 2 −· production was ~8-fold higher in neutrophils stimulated with f MLF compared to those stimulated with PMA [145].…”

“…We found that oleanolic acid has a relatively high inhibitory activity on Ca 2+ flux in f MLF-stimulated human neutrophils and FPR1 HL-60 cells without a direct agonist effect in these cells (Table 2), suggesting that this compound could be a true FPR1 antagonist. Epibetulinic acid (Table 1) isolated from Pachycentria formosana demonstrated similar inhibitory effects as oleanolic acid [143], and its derivative, betulinic acid, also inhibited f MLF-induced O 2 −· production by neutrophils. However, this triterpene did not affect f MLF-induced release of HNE [116], suggesting that it has an FPR1-independent mechanism of action.…”

Triterpenoids as Neutrophil Elastase Inhibitors

“…In two recent studies, the inhibitory effect of triterpenoids on elastase release from human neutrophils in response to N-formyl-Lmethionyl-L-leucyl-L-phenylalanine plus cytochalasin B (fMLP/CB) stimulation has been investigated. In the first study, oleanolic acid (14) and eight oleanolic acid-containing saponins (26)(27)(28)(29)(30)(31)(32)(33) isolated from the roots of Panax japonicus var. major were biologically evaluated [27].…”