Phenanthrenes from Orchidaceae and Their Biological Activities

Vasas, Andrea

doi:10.1007/978-3-030-11257-8_34-1

Cited by 1 publication

(1 citation statement)

References 195 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among them, Orchidaceae and Juncaceae are the most abundant sources of these specific metabolites. Phenanthrenes have chemotaxonomical significance since the presence of certain substituents in them are apparently restricted to certain families; e.g., almost all of the stilbene- and p -hydroxybenzyl-substituted compounds have been reported in Orchidaceae species, while vinyl substitution occurs only in Juncaceae phenanthrenes [ 9 , 10 ]. Moreover, phenanthrenes possess noteworthy pharmacological activities, such as antiproliferative, anti-inflammatory, and antimicrobial properties [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Unique Phenanthrenes from Juncus ensifolius and Their Antiproliferative and Synergistic Effects with the Conventional Anticancer Agent Doxorubicin against Human Cancer Cell Lines

et al. 2022

Self Cite

View full text Add to dashboard Cite

Phenanthrenes are the main special metabolites of Juncaceae species from phytochemical, pharmacological, and chemotaxonomical points of view. The present study focused on the isolation, structure determination, and pharmacological investigation of phenanthrenes from Juncus ensifolius. Nineteen compounds, including 17 phenanthrenes, were identified from the methanol extract of the plant. Thirteen compounds, namely, ensifolins A–M (1–13), were obtained for the first time from natural sources. Four phenanthrenes [2-hydroxy-1,7-dimethyl-5-vinyl-9,10-dihydrophenanthrene (14), juncuenin B (15), juncatrin B (16), and sylvaticin A (17)], 4-hydroxybenzaldehyde (18) and luteolin (19) were isolated for the first time from J. ensifolius. Ensifolins A (1) and B (2) are structurally unique phenanthrenes, considering that they are flavonoid- (1) or benzaldehyde-adducts (2). The antiproliferative activity of all isolated compounds against HeLa, COLO 205, and COLO 320 cancer cells and a non-tumor (MRC-5) cell line was tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay. The luteolin-substituted phenanthrene ensifolin A (1) proved to be the most active against all three cancer cell lines (IC50 values 3.9–12.7 μM) and showed good selectivity (SI = 4.95) in the case of COLO 205. The best selectivity was recorded for ensifolins D (4, SI > 5.15, HeLa), H (8, SI > 8.13, HeLa), and 17 (SI > 9.43, HeLa). The synergistic activity of the compounds with doxorubicin was also tested on HeLa cells, and ensifolins E (5) and H (8) exhibited very strong synergism (CI < 0.1). In conclusion, these phenanthrenes are worthy of further investigation.

show abstract

Section: Introductionmentioning

confidence: 99%