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

Biomolecules

Jakob Troppmair¹  Stefania Marzocco²  Mostafa Alilou³  Hermann Stuppner³  Stefan Schwaiger³  Hossein Batooli⁴ 

[1] Daniel-Swarovski Research Laboratory, Department of Visceral, Transplant and Thoracic Surgery, Innsbruck Medical University, Innrain 66, 6020 Innsbruck, Austria;Department of Pharmacy, University of Salerno, Via Giovanni Paolo II 132, I-84084 Fisciano, SA, Italy;Institute of Pharmacy, Pharmacognosy, Center for Molecular Biosciences (CMBI), University of Innsbruck, 6020 Innsbruck, Austria;Kashan Botanical Garden, Research Institute of Forests and Rangelands, Agricultural Research, Education and Extension Organization (AREEO), Tehran 193951113, Iran;

关键词: dionysia diapensifolia bioss;    anti-inflammatory;    macrophages;    phenolic compounds;    flavone;   

DOI  :  10.3390/biom10030438

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown