Dihydro Oxyresveratrol
Products : Dihydro Oxyresveratrol
Chemical Name : 2.4.3'.5'-Tetrahydroxy-bibenzyl
CAS No : 24082-42-6
Molecular Formula : C14H14O4
Molecular Weight : 246.25900
Bio Activity : Tyrosinase inhibitor
Physical Properties : Brownish yellow Amorphous solid.
Solubility : Soluble in Water, Methanol, Ethanol and Acetone.
Chemical Reaction : Characteristic reactions of poly phenol.
Synonyms : Bibenzyl Tetrol-(2.4.3'.5'), 2.4.3'.5'-Tetrahydroxy-bibenzyl, Dihydroxy Resveratrol
A study conducted for the evaluation of the tyrosinase inhibitory activity of 2.4.3'.5'-Tetrahydroxy-bibenzyl using L- Dopa as substrate performed kojic acid was used as standard and compared its activity with oxyresveratrol. The IC50 values observed were 12.7, 133.4 and 1.6 muM respectively for Oxyresveratrol, kojic acid and Dihydro Oxyresveratrol.
Comparison of the IC50 Values shows that Dihydro Oxyresveratrol has about 8 times more inhibitory activity than the Parent compound, Oxyresveratrol.
The compound , oxyresveratrol and kojic acid inhibited the enzyme in a dose dependent manner Dihydroxy oxyresveratrol is an established noncompetitive inhibitor of tyrosinase. A comparative study of the two compounds on their Km values shows 5 fold higher affinity to the enzyme of Dihydro Oxyresveratrol than oxyresveratrol.
A comparative account of the cytotoxicity study establish the compound to be devoid of cytotoxicity to human cells such as KB, BC, NCI-H 187.
Tyrosinase inhibitory activity
A comparative study of Tyrosinase activity
| Compound IC50(muM) | % inhibition(at100muM) | IC50(muM) |
|---|---|---|
| Kojic acid 133.4 | 41.1 | 133.4 |
| Licorice extract | 71 | 62 |
| Oxyresveratrol 12.7 | 83.5 | 12.7 |
| Dihydro Oxyresveratrol 1.6 | 96.3 | 1.6 |
Graph 1
Dose dependent inhibitory effect on tyrosinase by Dihydro Oxyresveratrol, Oxyresveratrol and Kojic acid.
Samples shown are Oxyresveratrol (Circle), Tetra hydro oxy bibenzyl (triangle) and Kojic acid (diamond). Effects on tyrosinase activity by the samples as a function of concentration are represented as inhibition % , means ± S.E of three independent tests.
Graph 2
Kinetic studies conducted on Dihydro Oxyresveratrol in comparison with oxyresveratrol to measure the ability to inhibit mushroom tyrosinase with L'Dopa as substrate,.
Data were obtained as mean values of I/V, inverse of the increase of absorbance at the wave length 490 mm per minute (∆A490/ min) , with different concentrations of L Dopa as substrate. Inhibitors of the enzyme were tetrahydro bibenzyl with 2.4 Mm( triangle ∆) , 1.2 Mm ( circle O) and No bibenzyl ( circle O)
The observed Km value and V max establish the product as a non competitive inhibitor of tyrosinase on L Dopa. The Ki value obtained in the study establish the compound Dihydro Oxyresveratrol has 5 fold higher affinity to the enzyme than oxyresveratrol.
Specifications
| Properties | Specification |
|---|---|
| Colour and appearance | Brownish yellow amorphous solid. |
| Solubility | Freely soluble in Water, Methanol, Ethanol and Acetone |
| Water insoluble | Less than 0.5 % at 80C |
| Ash content | Less than 0.5% |
| Moisture content | Less than 1% |
| Heavy metals | Less than 20 ppm |
| Assay | By HPLC, Not less than 98% |
| Method of analysis | AOAC Official methods of analysis 1990 |
Reference
-
Bioorg Med Chem Lett. 2006 Nov 1;16(21):5650-3. Epub 2006 Aug 17Likhitwitayawuid K1, Sornsute A, Sritularak B, Ploypradith P, Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent.
click here.. -
International Journal of Cosmetic SciencesVolume 28, Issue 4 ,August 2006, Pages 269–276P. Tengamnuay, K. Pengrungruangwong, I. Pheansri, K. Likhitwitayawuid, Artocarpus lakoocha heartwood extract as a novel cosmetic ingredient: evaluation of the in vitro anti-tyrosinase and in vivo skin whitening activities
click here.. -
Current Science, Vol 94., No.1, January 2008Kittisak Likhiwitayuid .
Stilbenes with tyrosinase inhibitory activiry
-
Int. J. Mol. Sci. 2009, 10(6), 2440-2475Te-Sheng Chang An Updated Review of Tyrosinase Inhibitors
click here..
Overview
Products : Dihydro Oxyresveratrol
Chemical Name : 2.4.3'.5'-Tetrahydroxy-bibenzyl
CAS No : 24082-42-6
Molecular Formula : C14H14O4
Molecular Weight : 246.25900
Bio Activity : Tyrosinase inhibitor
Physical Properties : Brownish yellow Amorphous solid.
Solubility : Soluble in Water, Methanol, Ethanol and Acetone.
Chemical Reaction : Characteristic reactions of poly phenol.
Synonyms : Bibenzyl Tetrol-(2.4.3'.5'), 2.4.3'.5'-Tetrahydroxy-bibenzyl, Dihydroxy Resveratrol
A study conducted for the evaluation of the tyrosinase inhibitory activity of 2.4.3'.5'-Tetrahydroxy-bibenzyl using L- Dopa as substrate performed kojic acid was used as standard and compared its activity with oxyresveratrol. The IC50 values observed were 12.7, 133.4 and 1.6 muM respectively for Oxyresveratrol, kojic acid and Dihydro Oxyresveratrol.
Comparison of the IC50 Values shows that Dihydro Oxyresveratrol has about 8 times more inhibitory activity than the Parent compound, Oxyresveratrol.
The compound , oxyresveratrol and kojic acid inhibited the enzyme in a dose dependent manner Dihydroxy oxyresveratrol is an established noncompetitive inhibitor of tyrosinase. A comparative study of the two compounds on their Km values shows 5 fold higher affinity to the enzyme of Dihydro Oxyresveratrol than oxyresveratrol.
A comparative account of the cytotoxicity study establish the compound to be devoid of cytotoxicity to human cells such as KB, BC, NCI-H 187.
Tyrosinase inhibitory activity
A comparitive study of Thyrosinase activity
| Compound IC50(muM) | % inhibition(at100muM) | IC50(muM) |
|---|---|---|
| Kojic acid 133.4 | 41.1 | 133.4 |
| Licorice extract | ||
| Oxyresveratrol 12.7 | 83.5 | 12.7 |
| Dihydro Oxyresveratrol 1.6 | 96.3 | 1.6 |
Graph 1
Dose dependent inhibitory effect on tyrosinase by Dihydro Oxyresveratrol, Oxyresveratrol and Kojic acid.
Samples shown are Oxyresveratrol (Circle), Tetra hydro oxy bibenzyl (triangle) and Kojic acid (diamond). Effects on tyrosinase activity by the samples as a function of concentration are represented as inhibition % , means ± S.E of three independent tests.
Graph 2
Kinetic studies conducted on Dihydro Oxyresveratrol in comparison with oxyresveratrol to measure the ability to inhibit mushroom tyrosinase with L'Dopa as substrate,.
Data were obtained as mean values of I/V, inverse of the increase of absorbance at the wave length 490 mm per minute (∆A490/ min) , with different concentrations of L Dopa as substrate. Inhibitors of the enzyme were tetrahydro bibenzyl with 2.4 Mm( triangle ∆) , 1.2 Mm ( circle O) and No bibenzyl ( circle O)
The observed Km value and V max establish the product as a non competitive inhibitor of tyrosinase on L Dopa. The Ki value obtained in the study establish the compound Dihydro Oxyresveratrol has 5 fold higher affinity to the enzyme than oxyresveratrol.
Specification
| Properties | Specification |
|---|---|
| Colour and appearance | Brownish yellow amorphous solid. |
| Solubility | Freely soluble in Water, Methanol, Ethanol and Acetone |
| Water insoluble | Less than 0.5 % at 80C |
| Ash content | Less than 0.5% |
| Moisture content | Less than 1% |
| Heavy metals | Less than 20 ppm |
| Assy | By HPLC, Not less than 98% |
| Method of analysis | AOAC Official methods of analysis 1990 |
Reference
-
Bioorg Med Chem Lett. 2006 Nov 1;16(21):5650-3. Epub 2006 Aug 17.Likhitwitayawuid K1, Sornsute A, Sritularak B, Ploypradith P Chemical transformations of oxyresveratrol (trans-2,4,3',5'-tetrahydroxystilbene) into a potent tyrosinase inhibitor and a strong cytotoxic agent
click here.. -
International Journal of Pharmacology, 10: 44-54, 2014Li Xu, Chao Liu, Wei Xiang, Hu Chen, Xiaoli Qin and Xianzhi Huang Advances in the Study of Oxyresveratrol.
click here.. -
Current Science, Vol 94., No.1, January 2008Kittisak Likhiwitayuid Stilbenes with tyrosinase inhibitory activiry
-
Current Science, Vol 94., No.1, January 2008Kittisak Likhiwitayuid Stilbenes with tyrosinase inhibitory activiry