Unusual Secondary Metabolites of the Aerial Parts of Dionysia diapensifolia Bioss. (Primulaceae) and Their Anti-Inflammatory Activity

Abstract

The genus Dionysia, belonging to the Primulaceae family, encompasses more than 50 species worldwide with a center of diversity located in the arid Irano-Turanian mountains. In this study, a phytochemical investigation of the aerial parts of D. diapensifolia Bioss. led to the isolation of 24 phenolic compounds 1–7 and 9–25, and one sesquiterpenoid 8. Compound 1 was identified as new natural product, while isolation of 2 and 3, already known as synthetic products, from a natural source is reported for the first time in the present study. Isolation of compound 8 from a Dionysia species and indeed the whole Primulaceae family is reported for the first time too. Structure elucidation was performed by extensive spectroscopic analyses (1D-, 2D-NMR, and MS), and by comparison with reported literature data. Furthermore, DP4+ chemical shift probability calculations were performed to establish the relative configuration of compound 1. Additionally, subfractions obtained by liquid-liquid extraction of the methanolic extract of the plant, and subsequently the isolated new and selected known compounds 1–4, 6, 8–11 obtained from the diethyl ether subfraction were investigated for their inhibitory effect on NO release and iNOS and COX-2 expression in J774A.1 murine macrophages. The results showed a potential anti-inflammatory activity of the obtained subfractions, of which the diethyl ether subfraction was the most active one in inhibiting NO release and COX-2 expression (p < 0.001). Among the investigated isolated compounds, compound 4 significantly (p < 0.001) inhibited NO release and iNOS and COX-2 expression in a comparable manner like the used positive controls (L-NAME and indomethacin, respectively). Moreover, other isolated substances displayed moderate to high inhibitory activities, illustrating the potential anti-inflammatory activity of Dionysia diapensifolia.

Nor-abietane Diterpenoids fromPerovskia abrotanoidesRoots with Anti-inflammatory Potential

“…The secondary antibody was added in fixing solution, and cell fluorescence was evaluated using a fluorescence-activated cell sorting (FACSscan; Becton Dickinson, Milan, Italy) and elaborated with Cell Quest software (version 5; Becton Dickinson, Milan, Italy) as previously reported. 68 Data Analysis. Data are reported as mean ± standard error of the mean (SEM) values of at least three independent experiments, each in triplicate.…”

“…Anti-iNOS (BD Transduction Laboratories, Milan, Italy) antibody was then added for 30 min. The secondary antibody was added in fixing solution, and cell fluorescence was evaluated using a fluorescence-activated cell sorting (FACSscan; Becton Dickinson, Milan, Italy) and elaborated with Cell Quest software (version 5; Becton Dickinson, Milan, Italy) as previously reported …”

Flavone From Plants—Uncommonly Common? A Comprehensive Review

“…In this context, attention is drawn to co-occurring chalcone derivatives (Table 3), of which 2ʹß-dihydroxy chalcone (= (2Z )-3-hydroxy-1-(2-hydroxyphenyl)-3-phenyl-2-propen-1one) would be a likely candidate that could isomerize to unsubstituted flavanone, a compound detected in Dionysia diapensiifolia Boiss., albeit in trace amounts only. 48 This was the first report on the occurrence of flavanone in the Primula assemblage. Similarly, 2 ′ -hydroxy-2-methoxy chalcone (= (2E)-1-(2hydroxyphenyl)-3-(2-methoxyphenyl)-2-propen-1-one) could be a precursor of the corresponding 2ʹ-methoxy flavone, for which no intermediate flavanone was yet found.…”