C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-alpha Production

HANAKOVA, Z., J. HOSEK, Petr BABULA, Acqua S. DALL, Jiří VÁCLAVÍK a Karel ŠMEJKAL. C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-alpha Production. Journal of Natural Products. Washington: American Chemical Society, roč. 78, č. 4, s. 850-863. ISSN 0163-3864. doi:10.1021/acs.jnatprod.5b00005. 2015.

Základní údaje

• Originální název: C-Geranylated Flavanones from Paulownia tomentosa Fruits as Potential Anti-inflammatory Compounds Acting via Inhibition of TNF-alpha Production
• Autoři: HANAKOVA, Z., J. HOSEK, Petr BABULA, Acqua S. DALL, Jiří VÁCLAVÍK a Karel ŠMEJKAL.
• Vydání: Journal of Natural Products, Washington, American Chemical Society, 2015, 0163-3864.

Další údaje

• Originální jazyk: angličtina
• Typ výsledku: Článek v odborném periodiku
• Utajení: není předmětem státního či obchodního tajemství
• Impakt faktor: Impact factor: 3.662
• Organizační jednotka: Farmaceutická fakulta
• Doi: http://dx.doi.org/10.1021/acs.jnatprod.5b00005
• UT WoS: 000353665100033

Anotace

Eleven new C-geranylated flavonoids, tomentodiplacones L, M, and N (1, 2, 10), tomentodiplacol B (3), 3',4'-O-dimethyl-5'-hydroxydiplacone (4), mimulones F, G, and H (5, 6, 7), paulowniones A (8) and B (9), tomentone (11), and 3',4',5'-trimethoxyflavanone (12), together with 11 known flavonoids (13-23), were isolated from fruits of Paulownia tomentosa. The structures of the compounds isolated were determined by spectroscopic data interpretation. The ability of compounds 1-23, together with the nonprenylated flavanones eriodictyol (24) and naringenin (25), to reduce the production of the pro-inflammatory cytokine TNF-alpha in THP-1 cells after bacterial lipopolysaccharide stimulation was evaluated using an in vitro screening test. The preliminary structureactivity relationships of these derivatives were also studied, and the correlation of their TNF-alpha inhibitory activity with their lipophilicity was investigated. The mechanism of action of compounds with significant antiphlogistic potential (4, 7, 10, 14, 22) was investigated. These compounds reduced both the secretion of TNF-a and the level of its corresponding mRNA. Compounds 4, 7, 10, 14, and 22 inhibited the nuclear translocation of NF-kappa B, which controls the expression of TNF-alpha, by blocking the degradation of I kappa B.