Umbelliferone

(redirected from 7-hydroxycoumarin)

Um`bel`lif´er`one


n.1.(Chem.) A tasteless white crystalline substance, C9H6O3, found in the bark of a certain plant (Daphne Mezereum), and also obtained by the distillation of certain gums from the Umbelliferæ, as galbanum, asafetida, etc. It is analogous to coumarin. Called also hydroxy-coumarin. Its strong fluorescence under ultraviolet light makes it useful in analytical biochemistry, as, for exmple, to detect phosphatase activity by hydrolysis of umbelliferyl phosphate.
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The intensity of 7-hydroxycoumarin fluorescence was measured at excitation and emission wavelengths of 338 and 458 nm, respectively.
Reversible binding of 7-hydroxycoumarin (7-HC) to bSULT1A1 is detected by enhanced ligand emission at 400 nm, and previous titrations suggested a Kd for 7-HC of 0.
On the basis of IR, NMR and mass spec data, this compound was shown to be umbelliferone ot 7-hydroxycoumarin.
The fluorescent metabolite 7-hydroxycoumarin was measured using a Perkin--Elmer spectrofluorimeter, excitation wavelength 370nm; emission wavelength 474 nm.
Antitumour-activities of coumarin, 7-hydroxycoumarin and its glucuronide in several human tumour cell lines.
Phenol sulfotransferase (SULT1A1) catalyses sulfuryl group transfer from 3'phosphoadenosine-5'-phosphosulafe (PAPS) to phenolic xenobiotics such as 7-hydroxycoumarin (7HC).
Nine compounds were studied: 4-hydroxybenzaldehyde, salicylaldehyde, acetanilide, 4-hydroxycoumarin, 7-hydroxycoumarin, indole-3, carboxaldehyde, salicylic acid, cinnamic acid and 2-hydroxy cinnamic acid.
These were 7-ethoxyresorufin and resorufin for CYP1A2; coumarin and 7-hydroxycoumarin for CYP2A6; 7-ethoxy-4-(trifluoromethyl) coumarin (EFC) and 7-hydroxy-4-(trifluoromethyl) coumarin (HFC) for CYP2B6; dibenzylfluorescein (DBF) and fluorescein for CYP2C8 and CYP2C19; 7-methoxy-4-(trifluoromethyl) coumarin (MFC) and HFC for CYP2C9 and CYP3A4; and 7-methoxy-4-(aminomethyl) coumarin (MAMC) and 7-hydroxy-4-(aminomethyi) coumarin (HAMC) for CYP2D6.
Fluorescence samples were quantified by a calibration curve with resorufin or 7-hydroxycoumarin standards, using 535 or 380 nm (excitation wavelength) and 585 or 460 nm (emission wavelength), respectively.
CYP2A6 is one of the genetically polymorphic enzymes, known to be expressed predominantly in the liver and to be an exclusive catalyst of a conversion of coumarin to 7-hydroxycoumarin (7-OHC; Oscarson 2001; Pelkonen et al.
In general, troxerutin reduces the concentration of all coumarin-metabolites in the perfusate and bile and changes the ratio of the main metabolites, coumarin: 3-hydroxycoumarin: 7-hydroxycoumarin.