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J Nat Prod ; 83(8): 2456-2468, 2020 08 28.
Article in English | MEDLINE | ID: mdl-32786876

ABSTRACT

Phytochemical investigations of an extract of the aerial parts of Rydingia persica led to the isolation of 14 labdane-type diterpenoids, of which compounds 1-5, 8, and 12-14 turned out to be new natural products, while the remaining compounds were isolated for the first time from the genus Rydingia. Their structures were elucidated using 1D- and 2D-NMR and mass spectrometry, and their absolute configurations were determined by quantum chemical calculation methods. Furthermore, DP4+ NMR chemical shift probability calculations were performed for compounds 12-14, in order to elucidate the orientation of the ambiguous chiral center at C-15, prior to absolute configuration determination. The methanol extract of the aerial parts of R. persica along with subfractions obtained and selected isolated compounds were evaluated for their effects on inflammation-related factors such as nitrotyrosine formation, IL-6 release, and TNF-α release, along with tight-junction proteins claudin-1 and occludin expression in LPS-stimulated HaCaT cells. Occludin and claudin-1 are tight-junction proteins, which play a pivotal role in wound repair mechanisms. Overall, the subfractions and compounds isolated showed moderate to high activity, indicating that labdane-type diterpenoids contribute to the anti-inflammatory and wound-healing activity of R. persica.


Subject(s)
Diterpenes/chemistry , Diterpenes/pharmacology , Inflammation/prevention & control , Keratinocytes/drug effects , Leonurus/chemistry , Lipopolysaccharides/toxicity , Plant Components, Aerial/chemistry , Cells, Cultured , Diterpenes/isolation & purification , Humans , Inflammation/chemically induced , Inflammation Mediators/metabolism , Keratinocytes/metabolism , Spectrum Analysis/methods
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