Cytotoxic activity of C-geranyl compounds from Paulownia tomentosa fruits.
The newly discovered 5,7-dihydroxy-6-geranylchromone ( 1) was isolated from PAULOWNIA TOMENTOSA fruit and subsequently characterized. The structure of the isolated compound was elucidated on the basis of extensive NMR experiments including HMQC, HMBC, COSY, and NOESY, as well as HR-MS, IR, and UV. The cytotoxicity of 1 was evaluated using a plant cell model represented by tobacco BY-2 cells. The other phytoconstituents ( 2 - 8) previously isolated from P. TOMENTOSA were similarly evaluated together with the known flavanones 10 and 11. The cytotoxicity (human erythro-leukaemia cell line K562) and activity on erythroid differentiation of compounds 2 - 9 and 12 and 13 have also been evaluated. Acteoside ( 2) was determined to be the most toxic of the compounds tested on BY-2 cells, diplacone ( 6) on the K562 cell line. Some aspects of the relationship between the flavanone skeleton substitution and the metabolic activation necessary for a toxic effect are discussed.
Smejkal
Karel
K
Department of Natural Drugs, University of Veterinary and Pharmaceutical Sciences Brno, Brno, Czech Republic. karel.mejkal@post.cz
Babula
Petr
P
Slapetová
Tereza
T
Brognara
Eleonora
E
Dall'acqua
Stefano
S
Zemlicka
Milan
M
Innocenti
Gabbriella
G
Cvacka
Josef
J
D002454:Cell Differentiation / Q000187:drug effects; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D041905:Erythroid Cells / Q000187:drug effects; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D005638:Fruit / Q000737:chemistry*; D006801:Humans; D020014:K562 Cells; D007928:Lethal Dose 50; D019684:Magnoliopsida / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D014026:Nicotiana / Q000166:cytology / Q000187:drug effects
C533645:5,7-dihydroxy-6-geranylchromone; D002867:Chromones; D044950:Flavanones; D010636:Phenols