Oxyresveratrol


Overview

Oxyresveratrol functions as skin whitening/lightening agent by inhibiting the tyrosinase activity. It shows 30/35 times stronger inhibition than Kojic acid and 10/12 times stronger than Licorice Extract. Very strong antioxidant activity coupled with antiglycation and UV protection ability enable wrinkle free glowing skin.

Products : Oxyresveratrol

Chemical Name : 2,3’,4,5’, Tetrahydroxystilbene

CAS No : 29700 – 22 – 9

Molecular Formula : C14 H12 O4

Molecular Weight : 244.243 gm/mol

Physical Properties : Pale Yellow Amorphous Solid.

Solubility : Soluble in water, Methanol, Ethanol, Acetone, Propylene Glycol.

Chemical Reaction : Readily reduced Fehling's solution and Tollens reagent


Skin lightening potential


  • 1. Cell based Melanogenesis Inhibitory Assay:

    Intracellular melanin in B16F1 melanoma cell lines were treated with various concentrations of Oxyresveratrol over a period of 9 days. Melanocyte inducing hormone MSH was used to induce melanin in cell lines.

    Result : Oxyresveratrol showed a strong inhibitory activity on melanogenesis with IC50 of 1.2 micro gm/ml when compared with Kojic acid (IC50 40.1 micro gm/ ml) and resveratrol 54.6 micro gm/ ml. Oxyresveratrol showed a dose dependent inhibitory effect on L-tyrosinase Oxidation. Oxyresveratrol is an inhibitor of tyrosinase activity, but dos not suppress the synthesis of tyrosinase. The inhibitory activity is 32 fold more than Kojic acid.

  • Dose dependent inhibitory effects on mushroom tyrosinase by oxyresveratrol, resveratrol and kojic acid. : Samples shown are oxy (circle), resveratrol (rectangle)

    And kojic acid ( triangle) Effects on tyrosinase activity by samples as a function of concentration are represented as inhibition %, means + - S.E of three independent tests. [ Ref: J of biological chemistry 277, 18, 2002]

  • 2. In vivo evaluation of skin whitening activity of oxyresveratrol solution in volunteers :

    A protocol approved chemical study conducted involved sixty female volunteers. A solution of 0.25% oxyresveratrol (As A.L. Extract), 0.25% Licorice extract and 3% Kojic acid in propylene glycol were used. Application continued for 12 weeks and the melanin content measured at 2 weeks interval. The average percentage whitening increased with treatment duration,. 0.18% at 2 weeks to 2.78% at 12 weeks. The results with K.A and W.E during the same period were much lower.

    Whitening effect of Oxyresveratrol [ Artocarpus Lakoocha extract] in propylene Glycol in comparison with licorice extract and Kojic acid .Significantly different from control within group, P <0.05 by Student's T –test ( adapted from Tanguay et al )


  • 3. In vivo evaluation of lotion containing Oxyresveratrol:

    Another study with human volunteers applied a lotion of Oxyresveratrol prepared by oil in water emulsion and compared with a similar emulsion from Licorice extract . The results were very similar to that of the solution Oxyresveratrol was the most effective agent, giving the shortest onset of significant whitening effect after only 4 weeks of application, followed 3% KA and 0.25% In Extract. Effect also increased with time with maximum whitening observed at 12 weeks for oxyresveratrol.

    Whitening efficacy of Oxyresveratrol [ A lakoocha ] lotion in comparison with licorice lotion. Significantly different from control within group , P <0.05 by Student's T- test


  • 4. U.V.B. Protection Activity :

    Fibroblast cells were treated with varying concentration of Oxyresveratrol (A.L. Extract) and exposed to U.V. B dosage. Cells were then incubated and natural red staining technique was used to analyze cell viability. Percentage of U>V. protection was calculated by comparing cytotoxicity in exposed and unexposed cells.

    Oxyresveratrol showed 50% reduction in U.V.B induced cytotoxicity at concentration of 18 Mg/ml.


  • 5. Antioxidant potential as measured by ORAC Assay:

    ORAC assay is a measure of antioxidant capacity against free radicals. Different concentration of test sample (oxyresveratrol) were compared with standard compound ----------. The results obtained should a higher ORAC value for oxyresveratrol.


  • 6. Skin anti aging potential – Measured by anti glycation activity:

    Glycation is the reaction that occurs when the reducing portion of monosaccharides such as glucose or fructose ----------- to macromolecules of portion or lipid structure to form advanced glycation end products (AGE’s), AGE’s are related to the pathogenesis of skin aging. Oxyresveratrol exhibited anti glycation with IC50 value of 3.3 Mg/ml. Compared to aminoguanidine IC50 12.5 Mg/ml. The ---------- antiglycation activity contribute to skin anti aging in formulations.


  • 7. Irritation tests :

    Oxyresveratrol do not show skin irritation, Eye irritation, skin sensitization and acute oral toxicity for animals and human skin irritation.


Benefits of Oxyresveratrol

  1. High tyrosinase inhibition,.
  2. Strong inhibitory activity on Melanogenesis.
  3. Antioxidant and can act as skin anti aging compound.
  4. Significant U>V. protection

Clinical Trials and Observed Results

  1. The inhibitory effect on melanin symptom is about 35 more in Oxyresveratrol compared to Kojic acid and 10/12 times that of Licorice extract, which are the most common ingredients of skin whitening formulations.
  2. Oxyresveratrol showed the shortest onset significant whitening effect after 4 weeks, which Kojic acid should significant whitening after 6 weeks and Licorice extract in 10 weeks
  3. Whitening effect with oxyresveratrol continuously increased with treatment duration. Percentage whitening w2as 1% in 1 week , 1.5% in 2 weeks, 2.23% in 3 weeks and attained steady value of 2.78% after 12 weeks.
  4. Significant whitening effect with Kojic acid was observed after 6 weeks and the maximum observed was only 2.23% after 12 weeks. Effective whitening was still lower with Licorice Extract.
  5. The depigmenting effect of oxyresveratrol works through the reversible inhibitions of tyrosinase rather than the suppression of the expression and synthesis of tyrosinase enzyme.

Specifications

Properties Specification
Colour and appearance Pale yellow amorphous solid, absorb moisture on exposure to air
Solubility Freely soluble in Water, Methanol, Ethanol and Acetone
Water insoluble Less than 0.5 %
Ash content Less than 0.5%
Moisture content Less than 1%
Melting Point 203 – 206C
Heavy metals Less than 20 ppm
Assy By HPLC, Not less than 98%
Method of analysis AOAC Official methods of analysis 1990

Reference

  • International Journal of Cosmetic SciencesVolume 28, Issue 4 ,August 2006, Pages 269–276
    P. 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..

  • Cosmeceutical development of oxyresveratrol from Mahad
    Cosmeceutical development of oxyresveratrol from Mahad
    S Natakankitkul, N Chareonmuang, T Panyakhong, Thai . j .Pharam.Sci.Vol 38 , 2013
    click here..

  • Tropical Journal of Pharmaceutical Research February 2012; 11 (1): 69-74
    Prasit Suwannalert, Nasapon Povichit, Pranom Puchadapirom1 and Mutita Junking: -
    Anti-Aging Activity and Non-Toxic Dose of Phytooxyresveratrol from Artocarpus lakoocha Roxb
    click here..

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  • Biochemical and Biophysical Research Communications, Volume 243, Issue 3,
    Nam-Ho Shin, Shi Yong Ryu , Eun Ju Choi , Seh-Hoon Kang , IL-Moo Chang , Kyung Rak Min , Youngsoo Kim , Oxyresveratrol as the Potent Inhibitor on Dopa Oxidase Activity of Mushroom Tyrosinase
    24 February 1998, Pages 801-803

    click here..

  • The Journal of Biological Chemistry 277, 16340-16344.( 2002)
    Yeon Mi Kim, Jieun Yun, Chong-Kil Lee, Hwanghee Lee, Kyung Rak Min andYoungsoo Kim, Oxyresveratrol and Hydroxystilbene Compounds.INHIBITORY EFFECT ON TYROSINASE AND MECHANISM OF ACTION
    click here..

  • j. Cosmet. sci., 54, 133-142 (March/April 2003)
    KANG TAE LEE, KWANG SIK LEE, JI HEAN JEONG, BYOUNG KEE JO, MOON YOUNG HEO, and HYUN PYO KIM, Inhibitory effects of ramulus mori extracts on melanogenesis
    click here..

  • K Wachiranuntasin.
    Evaluation of stability, antioxidative and free radical scavenging activities of rtocar artocarpus lakoocha heartwood extract Bangkok: Chulalongkorn University, 2005

  • Biochemical an Bdiophysical Research CommunicationsVolume 307, Issue 4, 8 August 2003,
    Kenji Ohguchia,Toshiyuki Tanakab, Tadashi Kidoc,Kimiye Babac,Munekazu Iinumad, Kenji Matsumotoa, Yukihiro Akaoa,Yoshinori Nozawaa Effects of hydroxystilbene derivatives on tyrosinase activity, pages 861–863
    click here..

  • Pigment Cell and Melanoma Research , Volume 11, Issue 6,December 1998 , Pages 355–361
    TOMOHIRO YOKOTA,HIROYUKI NISHIO,YASUO KUBOTA,MASAKO MIZOGUCHI The Inhibitory Effect of Glabridin from Licorice Extracts on Melanogenesis and Inflammation
    click here..

  • JAASP, 2013, 2: 243-253
    V Teeranachaideekul, S Nithitanakool, T Junhunkit… Liposomes: A novel carrier system for Artocarpus lakoocha extract to improve skin whitening
    click here..

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