Olivetol

The leaves of Grevillea robusta.

Preparation and evaluation of molecularly imprinted polymer of olivetol for solid phase extraction.[Pubmed:24063201]

Se Pu. 2013 Jun;31(6):587-95.

Molecularly imprinted polymer (MIP) was synthesized by bulk polymerization, using Olivetol as template molecule, methyl acrylic acid (MAA) as monomer, ethylene glycol dimethacrylate (EDMA) as crosslinker, toluene and dodecanol as solvents. The resulted MIP was characterized by the equilibrium binding experiments, scanning electron microscope (SEM) and Fourier transform infrared spectrometer (FTIR). The polymer was then applied to solid phase extraction (SPE) of Olivetol from spiked wheat bran samples. From the equilibrium binding experiments, it was showed that MIP had a better recognizability for the template molecule. Scatchard analysis showed that MIP had specific adsorption to Olivetol with two classes of binding sites. The high and low binding sites dissociation constants were 0.021 and 1.002 mmol/L. The corresponding maximum binding capacities were 18.74 and 135.9 micromol/g, respectively. Under the optimum condition of SPE, the recoveries of Olivetol on MIP cartridge were in the range of 97.8% - 98.8%. The relative standard deviations (RSDs) were 2.8% -4.2%. The linearity range was between 0.1 and 100 mg/L. The limit of detection (S/N = 3) was 0.062 mg/L. MIP cartridge showed stronger selectivity, higher recovery and purified the sample more drastically compared with non-imprinted polymer (NIP) cartridge and commercial poly (styrene/divinyl-benzene) (PLS) cartridge.

Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olivetol, orcinol and resorcinol.[Pubmed:9684980]

Free Radic Res. 1998 Apr;28(4):359-68.

Resorcinols (pentadecylresorcinol, Olivetol, orcinol and resorcinol) exhibit antioxidant properties in liposomal systems. Antioxidant potency depends on the length of the alkyl chain. Pentadecylresorcinol has been demonstrated to be the most active antioxidant, indicating significance of its alkyl chain in a lipid bilayer. Quantum DFT computations demonstrated that hydroxyl group attached to the ring is the first target for the hydrogen abstraction after formation of the radical. However, the carbons of the side chain could also participate in the antioxidant properties of the alkylresorcinols. Formation of the radical at the hydroxyl oxygen initiates changes in the electron density which destabilise the whole system and subsequently leads to oxidation of the ring. The detailed study of lipophilicity and electrostatic properties of resorcinols is discussed.

Biotransformation of olivetol by Syncephalastrum racemosum.[Pubmed:6512535]

J Nat Prod. 1984 Sep-Oct;47(5):828-34.

A study of the biotransformation of Olivetol by Syncephalastrum racemosum ATCC 18192 has led to the isolation of three metabolites, which were identified as 4'-hydroxy-Olivetol, 3-(3,5-dihydroxyphenyl)-1-propanol, and 3-(3,5-dihydroxyphenyl)-1-propanoic acid. The structures of the isolated metabolites were deduced by comparison of their spectral properties (pmr, cmr, ms) with those of Olivetol. The absolute configuration of 4'-hydroxy-Olivetol was determined to be R by the Horeau partial resolution method. Biotransformation of Olivetol therefore appears to occur by a subterminal oxidation process.

Olivetol is a naturally phenol found in lichens and produced by certain insects, acting as a competitive inhibitor of the cannabinoid receptors CB1 and CB2. Olivetol also inhibits CYP2C19 and CYP2D6 activity, with IC50s of 15.3 μM, 7.21 μM and Kis of 2.71 μM, 2.87 μM, respectively.

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