| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H12O4 |
| Molecular Weight | 244.2427 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(O)=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1
InChI
InChIKey=PDHAOJSHSJQANO-OWOJBTEDSA-N
InChI=1S/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+
Hydroxyresveratrol (Oxyresveratrol) is a major active compound in the heartwood of Artocarpus lacucha. It was first isolated from the heartwood of Artocarpus lakoocha, and has also been found in various plants, including Smilax China, Morus alba, Varatrum nigrum, Scirpus maritinus, and Maclura pomifera. Oxyresveratrol, an aglycone of mulberroside A, has been produced by microbial biotransformation or enzymatic hydrolysis of a glycosylated stilbene mulberroside A, which is one of the major compounds of the roots of M. alba.
Oxyresveratrol plays an important role in anti-tyrosinase, antioxidant, anti-inflammatory, antiviral and neuroprotective properties. There are many A. lacucha commercial products available on the market for skin whitening and anti-aging effects. OxyResvenox™ is the registered trademark of Oxyresveratrol from Sabinsa. Oxyresveratrol is an analog of Resveratrol and is of synthetic origin. The hydroxystilbene compounds including oxyresveratrol and resveratrol showed the potent inhibitory effect on tyrosinase activity. Oxyresveratrol is also naturally present in Morus alba L., Morus bombycis. Oxyresveratrol exhibits a potent inhibitory effect on dopa oxidase activity of tyrosinase
which catalyzes rate-limiting steps of melanin biosynthesis. Oxyresveratrol showed superoxide scavenging effects with the IC50 values 3.81 ± 0.5 uM,
Oxyresveratrol exhibited a DPPH free radical scavenging effect (IC50 = 23.4 ± 1.5 uM).
Oxyresveratrol also showed hepatoprotective effects with EC50 values 32.3 ± 2.62 uM, on
tacrine-induced cytotoxicity in human liver-derived Hep G2 cells. Oxyresveratrol significantly inhibited LPS-evoked nuclear translocation of NF-kappaB and
cyclooxygenase-2 (COX-2) activity in RAW 264.7 cells.
The results suggest that the anti-inflammatory properties of oxyresveratrol might be
correlated with inhibition of the iNOS expression through down-regulation of NF-kappaB
binding activity and significant inhibition of COX-2 activity. Oxyresveratrol revealed a dose-dependent neuroprotective effect in an in vivo stroke model.
This may prove to be beneficial for a therapeutic strategy to limit brain injury in acute brain ischemia.
CNS Activity
Approval Year
PubMed
Patents
Sample Use Guides
Rats: Oxyresveratrol (10 or 20 mg/kg) significantly reduced the brain infarct volume by approximately 54% and 63%, respectively, when compared to vehicle-treated MCAO rats. Oxyresveratrol (2, 10, 20 and 30 mg/kg body weight in a total volume of 1 ml in 30% ethanol) or equal volumes
of the vehicle were administered intraperitoneally (i.p.) in
animals twice: at the time of occlusion and at the time
of reperfusion.
Route of Administration:
Intraperitoneal
SUBSTANCE RECORD
